Patent US2805087A successfully refreshed from Google Patents.
Patent US4584303A successfully refreshed from Google Patents.
US4584303A
Expired / Lapsed
US
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N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds
Assignee: Anaquest Inc
•
Filing: 1985-03-01
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Granted: 1986-04-22
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Expires: 2005-03-01
Abstract
Abstract Compounds are disclosed of the formula <IMAGE> optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is defined in the disclosure.
Inventors
- 👤 Bao-Shan Huang
- 👤 Ross C. Terrell
- 👤 Kirsten H. Deutsche
- 👤 Linas V. Kudzma
- 👤 Nhora L. Lalinde
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 09:38
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C07D211/60; C07D211/62; C07D211/66; C07D405/00; C07D405/02; C07D405/12; C07D405/14; C07D409/00; C07D409/02; C07D409/04; C07D409/12; C07D409/14; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 144
Claim 1
Independent Claim
208 words
A compound of the formula ##STR25## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof; R 1 is a group of the formula ##STR26## wherein R 5 is selected from lower-alkyl, lower-cycloalkyl, halogenated lower-alkyl, phenyl, or phenyl lower-alkyl, and wherein each R 6 is independently selected from hydrogen, lower-cycloalkyl or lower-alkyl; R 2 is selcted from the group consisting of phenyl-lower-alkyl, lower-alkyl, lower-alkenyl, lower-alkynyl, halogenated lower-alkyl, (lower-cycloakyl)-lower-alkyl, (cyclopentyl)-lower-alkyl, thienyl lower-alkyl, thiazolyl lower-alkyl which can be substitued in the 4-position with a methyl group, (4,5-dihydro-5-oxo-1H-tetrazol-1-yl) lower-alkyl which can be substitued in the 4-position with a group selected from lower-alkyl, lower-cycloalkyl, phenyl or phenyl lower-alkyl, and substitued phenyl lower-alkyl in which the substituents on the phenyl ring are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio or combinations thereof; R 3 is selected from a group consisting of hydrogen, methoxymethyl, and a carboxylate radical represented by the formula ##STR27## wherein R 10 is selected from the group consisting of lower-alkyl, phenyl-lower-alkyl, lower-alkoxy-lower-alkyl, and phenyloxy-lower-alkyl; and R 4 is selected from hydrogen or methyl.
Claim 2
Dependent Claim
208 words
A compound of the formula ##STR25## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof; R 1 is a group of the formula ##STR26## wherein R 5 is selected from lower-alkyl, lower-cycloalkyl, halogenated lower-alkyl, phenyl, or phenyl lower-alkyl, and wherein each R 6 is independently selected from hydrogen, lower-cycloalkyl or lower-alkyl; R 2 is selcted from the group consisting of phenyl-lower-alkyl, lower-alkyl, lower-alkenyl, lower-alkynyl, halogenated lower-alkyl, (lower-cycloakyl)-lower-alkyl, (cyclopentyl)-lower-alkyl, thienyl lower-alkyl, thiazolyl lower-alkyl which can be substitued in the 4-position with a methyl group, (4,5-dihydro-5-oxo-1H-tetrazol-1-yl) lower-alkyl which can be substitued in the 4-position with a group selected from lower-alkyl, lower-cycloalkyl, phenyl or phenyl lower-alkyl, and substitued phenyl lower-alkyl in which the substituents on the phenyl ring are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio or combinations thereof; R 3 is selected from a group consisting of hydrogen, methoxymethyl, and a carboxylate radical represented by the formula ##STR27## wherein R 10 is selected from the group consisting of lower-alkyl, phenyl-lower-alkyl, lower-alkoxy-lower-alkyl, and phenyloxy-lower-alkyl; and R 4 is selected from hydrogen or methyl.
Claim 3
Dependent Claim
182 words
A compound of the formula ##STR28## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof; R 1 is a group of the formula ##STR29## wherein R 5 is lower-alkyl, or lower-cycloalkyl, and wherein each R 6 is independently selected from hydrogen, lower-alkyl or lower-cycloalkyl; R 2 is a group of the formula ##STR30## wherein each R 7 and R 8 are independently selected from hydrogen, phenyl or lower-alkyl, wherein R 9 is selected from the group consisting of phenyl, thienyl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl substitued in the 4-position by a group selected from lower-alkyl, phenyl-lower-alkyl or phenyl, and substituted phenyl in which the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof, and wherein n is an integer of from 0 to 7; R 3 is selected from a group consisting of hydrogen, methoxy-methyl, and a carboxylate radical represented by the formula ##STR31## wherein R 10 is selected from lower-alkyl, phenyl-lower-alkyl or lower-alkoxy-lower-alkyl.
Claim 4
Dependent Claim
182 words
A compound of the formula ##STR28## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof; R 1 is a group of the formula ##STR29## wherein R 5 is lower-alkyl, or lower-cycloalkyl, and wherein each R 6 is independently selected from hydrogen, lower-alkyl or lower-cycloalkyl; R 2 is a group of the formula ##STR30## wherein each R 7 and R 8 are independently selected from hydrogen, phenyl or lower-alkyl, wherein R 9 is selected from the group consisting of phenyl, thienyl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl substitued in the 4-position by a group selected from lower-alkyl, phenyl-lower-alkyl or phenyl, and substituted phenyl in which the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof, and wherein n is an integer of from 0 to 7; R 3 is selected from a group consisting of hydrogen, methoxy-methyl, and a carboxylate radical represented by the formula ##STR31## wherein R 10 is selected from lower-alkyl, phenyl-lower-alkyl or lower-alkoxy-lower-alkyl.
Claim 5
Dependent Claim
96 words
A compound of the formula ##STR32## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl or 2-substituted phenyl wherein said 2-substituent is selected from halogen, lower-alkoxy or lower-alkyl; R 1 is selected from the group consisting of methoxymethyl, 1-methoxyethyl, thienyl and furanyl; R 2 is selected from the group consisting of benzyl, 2-phenylethyl, 2-(2-fluorophenyl)-ethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, 2-(3-thienyl)-ethyl, 2-(2-thienyl)ethyl, 2-(4-methylthiazol-5-yl)ethyl, 2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl, and 2-methyl-1-propyl; R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group; and R 4 is selected from hydrogen or methyl.
Claim 6
Dependent Claim
96 words
A compound of the formula ##STR32## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl or 2-substituted phenyl wherein said 2-substituent is selected from halogen, lower-alkoxy or lower-alkyl; R 1 is selected from the group consisting of methoxymethyl, 1-methoxyethyl, thienyl and furanyl; R 2 is selected from the group consisting of benzyl, 2-phenylethyl, 2-(2-fluorophenyl)-ethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, 2-(3-thienyl)-ethyl, 2-(2-thienyl)ethyl, 2-(4-methylthiazol-5-yl)ethyl, 2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl, and 2-methyl-1-propyl; R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group; and R 4 is selected from hydrogen or methyl.
Claim 7
Dependent Claim
61 words
A compound of the formula ##STR33## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl; R 1 is methoxymethyl or furanyl; R 2 is selected from the group consisting of 2-phenylethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, and 2-(2-thienyl)ethyl; and R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group.
Claim 8
Dependent Claim
61 words
A compound of the formula ##STR33## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl; R 1 is methoxymethyl or furanyl; R 2 is selected from the group consisting of 2-phenylethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, and 2-(2-thienyl)ethyl; and R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group.
Claim 9
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-[2-(2-thienyl)ethyl]-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 10
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-[2-(2-thienyl)ethyl]-4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-(2-phenylethyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-(2-phenylethyl)-4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-[2-(2-thienyl)ethyl]-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 14
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-(2-phenylethyl)-4-(N-phenyl-2-furoylamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 15
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-(2-phenylethyl)-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 16
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-(2-phenylethyl)-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 17
Dependent Claim
17 words
A compound according to claim 4, which comprises 1-(2-phenyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 18
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 19
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)-2-methoxypropionamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 20
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)-3-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 21
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(1-phenyl-2-propyl)-4-[N-(2-methoxyphenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(3-thienyl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 23
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(4-methylthiazol-5-yl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 24
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(2-fluorophenyl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 25
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(1-phenyl-2-propyl)-4-(N-phenyl-methoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 26
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-benzyl-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 27
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(2-methyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 28
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(3-thienyl)ethyl]-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 29
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(3-phenyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 30
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 31
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-furoylamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 32
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 33
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 34
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-methoxyphenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 35
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 36
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 37
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 38
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 39
Dependent Claim
17 words
A compound according to claim 3, which comprises trans-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 40
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 41
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-methoxypropionamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 42
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-methoxyphenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 43
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 44
Dependent Claim
17 words
A compound according to claim 5, which comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-chlorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 45
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 46
Dependent Claim
17 words
A compound according to claim 3, which comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 47
Dependent Claim
17 words
A compound according to claim 3, which comprises trans-1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 48
Dependent Claim
17 words
A compound according to claim 3, which comprises 1-(2-phenylethyl)-4-[N-(2-methoxyphenyl)-2-methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 49
Dependent Claim
222 words
An analgesic composition comprising a non-toxic pharmaceutically acceptable carrier and an analgesically effective amount of a compound of the formula ##STR34## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof; R 1 is a group of the formula ##STR35## wherein R 5 is selected from lower-alkyl, lower-cycloalkyl, halogenated lower-alkyl, phenyl, or phenyl lower-alkyl, and wherein each R 6 is independently selected from hydrogen, lower-cycloalkyl or lower-alkyl; R 2 is selected from the group consisting of phenyl-lower alkyl, lower-alkyl, lower-alkenyl, lower-alknynyl, halogenated lower-alkyl, (lower-cycloalkyl)-lower-alkyl, (cyclopentyl)-lower-alkyl, thienyl lower-alkyl, thiazolyl lower-alkyl which can be substituted in the 4-position with a methyl group, (4,5-dihydro-5-oxo-1H-tetrazol-1-yl)lower-alkyl which can be substituted in the 4-position with a group selected from lower-alkyl, lower-cycloalkyl, phenyl or phenyl-lower-alkyl, and substituted phenyl lower-alkyl in which the substituents on the phenyl ring are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio or combinations thereof; R 3 is selected from a group consisting of hydrogen, methoxymethyl, and a carboxylate radical represented by the formula ##STR36## wherein R 10 is selected from the group consisting of lower-alkyl, phenyl-lower-alkyl, lower-alkoxy-lower-alkyl, and phenyloxy-lower-alkyl; and R 4 is selected from hydrogen or methyl.
Claim 50
Dependent Claim
222 words
An analgesic composition comprising a non-toxic pharmaceutically acceptable carrier and an analgesically effective amount of a compound of the formula ##STR34## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof; R 1 is a group of the formula ##STR35## wherein R 5 is selected from lower-alkyl, lower-cycloalkyl, halogenated lower-alkyl, phenyl, or phenyl lower-alkyl, and wherein each R 6 is independently selected from hydrogen, lower-cycloalkyl or lower-alkyl; R 2 is selected from the group consisting of phenyl-lower alkyl, lower-alkyl, lower-alkenyl, lower-alknynyl, halogenated lower-alkyl, (lower-cycloalkyl)-lower-alkyl, (cyclopentyl)-lower-alkyl, thienyl lower-alkyl, thiazolyl lower-alkyl which can be substituted in the 4-position with a methyl group, (4,5-dihydro-5-oxo-1H-tetrazol-1-yl)lower-alkyl which can be substituted in the 4-position with a group selected from lower-alkyl, lower-cycloalkyl, phenyl or phenyl-lower-alkyl, and substituted phenyl lower-alkyl in which the substituents on the phenyl ring are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio or combinations thereof; R 3 is selected from a group consisting of hydrogen, methoxymethyl, and a carboxylate radical represented by the formula ##STR36## wherein R 10 is selected from the group consisting of lower-alkyl, phenyl-lower-alkyl, lower-alkoxy-lower-alkyl, and phenyloxy-lower-alkyl; and R 4 is selected from hydrogen or methyl.
Claim 51
Dependent Claim
195 words
An analgesic composition comprising a non-toxic pharmaceutically acceptable carrier and an analgesically effective amount of a compound of the formula ##STR37## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof; R 1 a group of the formula wherein R 5 is lower-alkyl, or lower-cycloalkyl, and wherein each R 6 is independently selected from hydrogen, lower-alkyl or lower-cycloalkyl; R 2 is a group of the formula ##STR38## wherein each R 7 and R 8 are independently selected from hydrogen, phenyl, or lower-alkyl, wherein R 9 is selected from the group consisting of phenyl, thienyl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl substituted in the 4-position by a group selected from lower-alkyl, phenyl-lower-alkyl or phenyl, and substituted phenyl in which the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof, and wherein n is an integer of from 0 to 7; R 3 is selected from a group consisting of hydrogen, methoxy-methyl, and a carboxylate radical represented by the formula ##STR39## wherein R 10 is selected from lower-alkyl, phenyl-lower-alkyl or lower-alkoxy-lower-alkyl.
Claim 52
Dependent Claim
195 words
An analgesic composition comprising a non-toxic pharmaceutically acceptable carrier and an analgesically effective amount of a compound of the formula ##STR37## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof; R 1 a group of the formula wherein R 5 is lower-alkyl, or lower-cycloalkyl, and wherein each R 6 is independently selected from hydrogen, lower-alkyl or lower-cycloalkyl; R 2 is a group of the formula ##STR38## wherein each R 7 and R 8 are independently selected from hydrogen, phenyl, or lower-alkyl, wherein R 9 is selected from the group consisting of phenyl, thienyl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl substituted in the 4-position by a group selected from lower-alkyl, phenyl-lower-alkyl or phenyl, and substituted phenyl in which the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof, and wherein n is an integer of from 0 to 7; R 3 is selected from a group consisting of hydrogen, methoxy-methyl, and a carboxylate radical represented by the formula ##STR39## wherein R 10 is selected from lower-alkyl, phenyl-lower-alkyl or lower-alkoxy-lower-alkyl.
Claim 53
Dependent Claim
111 words
An analgesic composition comprising a nontoxic pharmaceutically acceptable carrier and an analgesically effective amount of a compound of the formula ##STR40## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl or 2-substituted phenyl wherein said 2-substituent is selected from halogen, lower-alkoxy or lower-alkyl; R 1 is selected from the group consisting of methoxymethyl, 1-methoxyethyl, thienyl and furanyl; R 2 is selected from the group consisting of benzyl, 2-phenylethyl, 2-(2-fluorophenyl)-ethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, 2-(3-thienyl)-ethyl, 2-(2-thienyl)ethyl, 2-(4-methylthiazol-5-yl)ethyl, 2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl, and 2-methyl-1-propyl; R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group; and R 4 is selected from hydrogen or methyl.
Claim 54
Dependent Claim
111 words
An analgesic composition comprising a nontoxic pharmaceutically acceptable carrier and an analgesically effective amount of a compound of the formula ##STR40## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl or 2-substituted phenyl wherein said 2-substituent is selected from halogen, lower-alkoxy or lower-alkyl; R 1 is selected from the group consisting of methoxymethyl, 1-methoxyethyl, thienyl and furanyl; R 2 is selected from the group consisting of benzyl, 2-phenylethyl, 2-(2-fluorophenyl)-ethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, 2-(3-thienyl)-ethyl, 2-(2-thienyl)ethyl, 2-(4-methylthiazol-5-yl)ethyl, 2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl, and 2-methyl-1-propyl; R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group; and R 4 is selected from hydrogen or methyl.
Claim 55
Dependent Claim
76 words
An analgesic composition comprising a nontoxic pharmaceutically acceptable carrier and an analgesically effective amount of a compound of the formula ##STR41## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl; R 1 is methoxymethyl or furanyl; R 2 is selected from the group consisting of 2-phenylethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, and 2-(2-thienyl)ethyl; and R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group.
Claim 56
Dependent Claim
76 words
An analgesic composition comprising a nontoxic pharmaceutically acceptable carrier and an analgesically effective amount of a compound of the formula ##STR41## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl; R 1 is methoxymethyl or furanyl; R 2 is selected from the group consisting of 2-phenylethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, and 2-(2-thienyl)ethyl; and R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group.
Claim 57
Dependent Claim
20 words
An analgesic composition according to claim 48, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 58
Dependent Claim
20 words
An analgesic composition according to claim 48, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 59
Dependent Claim
20 words
An analgesic composition according to claim 48, wherein said compound comprises 1-(2-phenylethyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 60
Dependent Claim
20 words
An analgesic composition according to claim 48, wheren said compound comprises 1-(2-phenylethyl)-4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 61
Dependent Claim
20 words
An analgesic composition according to claim 48, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 62
Dependent Claim
20 words
An analgesic composition according to claim 48, wherein said compound comprises 1-(2-phenylethyl)-4-(N-phenyl-2-furoylamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 63
Dependent Claim
20 words
An analgesic composition according to claim 48, wherein said compound comprises 1-(2-phenylethyl)-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 64
Dependent Claim
20 words
An analgesic composition according to claim 48, wherein said compound comprises 1-(2-phenylethyl)-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 65
Dependent Claim
20 words
An analgesic composition according to claim 48, wherein said compound comprises 1-(2-phenyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 66
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 67
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)-2-methoxypropionamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 68
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)-3-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 69
Dependent Claim
18 words
An analgesic composition according to claim 47, which comprises 1-(1-phenyl-2-propyl)-4-[N-(2-methoxyphenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 70
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-[2-(3-thienyl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 71
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-[2-(4-methylthiazol-5-yl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 72
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-[2-(2-fluorophenyl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 73
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-(1-phenyl-2-propyl)-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 74
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-benzyl-4-methoxycarbonyl-4-(N-phenyl-methoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 75
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-(2-methyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 76
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-[2-(3-thienyl)ethyl]-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 77
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-(3-phenyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyactamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 78
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 79
Dependent Claim
20 words
An analgesic composition accordiing to claim 47, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-furoylamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 80
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 81
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 82
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-methoxyphenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 83
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 84
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 85
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 86
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 87
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises trans-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 88
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 89
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-methoxypropionamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 90
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-methoxyphenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 91
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 92
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-chlorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 93
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 94
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 95
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises trans-1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 96
Dependent Claim
20 words
An analgesic composition according to claim 47, wherein said compound comprises 1-(2-phenylethyl)-4-[N-(2-methoxyphenyl)-2-methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 97
Independent Claim
226 words
A method for providing analgesia in a mammal comprising adminstering to such a mammal an analgesically effective amount of a compound of the formula ##STR42## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof; R 1 is a group of the formula ##STR43## wherein R 5 is selected from lower-alkyl, lower-cycloalkyl, halogenated lower-alkyl, phenyl, or phenyl lower-alkyl, and wherein each R 6 is independently selected from hydrogen, lower-cycloalkyl or lower-alkyl; R 2 is selected from the group consisting of phenyl-lower-alkyl, lower-alkyl, lower-alkenyl, lower-alkynyl, halogenated lower-alkyl, (lower-cycloalkyl)-lower-alkyl, (cyclopentyl)-lower-alkyl, thienyl lower-alkyl, thiazolyl lower-alkyl which can be substitued in the 4-position with a methyl group, (4,5-dihydro-5-oxo-1H-tetrazol-1-yl) lower-alkyl which can be substitued in the 4-position with a group selected from lower-alkyl, lower-cycloalkyl, phenyl or phenyl-lower-alkyl, and substitued phenyl lower-alkyl in which the substituents on the phenyl ring are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio or combinations thereof; R 3 is selected from a group consisting of hydrogen, methoxymethyl, and a carboxylate radical represented by the formula ##STR44## wherein R 10 is selected from the group consisting of lower-alkyl, phenyl-lower-alkyl, lower-alkoxy-lower-alkyl, and phenyloxyl-lower-alkyl; and R 4 is selected from hydrogen or methyl.
Claim 98
Independent Claim
226 words
A method for providing analgesia in a mammal comprising adminstering to such a mammal an analgesically effective amount of a compound of the formula ##STR42## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof; R 1 is a group of the formula ##STR43## wherein R 5 is selected from lower-alkyl, lower-cycloalkyl, halogenated lower-alkyl, phenyl, or phenyl lower-alkyl, and wherein each R 6 is independently selected from hydrogen, lower-cycloalkyl or lower-alkyl; R 2 is selected from the group consisting of phenyl-lower-alkyl, lower-alkyl, lower-alkenyl, lower-alkynyl, halogenated lower-alkyl, (lower-cycloalkyl)-lower-alkyl, (cyclopentyl)-lower-alkyl, thienyl lower-alkyl, thiazolyl lower-alkyl which can be substitued in the 4-position with a methyl group, (4,5-dihydro-5-oxo-1H-tetrazol-1-yl) lower-alkyl which can be substitued in the 4-position with a group selected from lower-alkyl, lower-cycloalkyl, phenyl or phenyl-lower-alkyl, and substitued phenyl lower-alkyl in which the substituents on the phenyl ring are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio or combinations thereof; R 3 is selected from a group consisting of hydrogen, methoxymethyl, and a carboxylate radical represented by the formula ##STR44## wherein R 10 is selected from the group consisting of lower-alkyl, phenyl-lower-alkyl, lower-alkoxy-lower-alkyl, and phenyloxyl-lower-alkyl; and R 4 is selected from hydrogen or methyl.
Claim 99
Independent Claim
206 words
A method for providing analgesia in a mammal comprising adminstering to such a mammal an analgesically effective amount of a compound of the formula ##STR45## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof; R 1 is a group of the formula ##STR46## wherein R 5 is lower-alkyl, or lower-cycloalkyl, and wherein each R 6 is independently selected from hydrogen, lower-alkyl or lower-cycloalkyl; R 2 is a group of the formula ##STR47## wherein each R 7 and R 8 are independently selected from hydrogen, phenyl, or lower-alkyl, wherein R 9 is selected from the group consisting of phenyl, thienyl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl substituted in the 4-position by a group selected from lower-alkyl, phenyl-lower-alkyl or phenyl, and substituted phenyl in which the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof, and wherein n is an integer of from 0 to 7; R 3 is selected from a group consisting of hydrogen, methoxy-methyl, and a carboxylate radical represented by the formula ##STR48## wherein R 10 is selected from lower-alkyl, phenyl-lower-alkyl or lower-alkoxy-lower-alkyl.
Claim 100
Independent Claim
206 words
A method for providing analgesia in a mammal comprising adminstering to such a mammal an analgesically effective amount of a compound of the formula ##STR45## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is selected from the group consisting of phenyl and substituted phenyl wherein the substituents are selected from halogen, cyano, lower-alkoxy, lower-alkyl, lower-alkylenedioxy, halogenated lower-alkyl, lower-alkylthio, or combinations thereof; R 1 is a group of the formula ##STR46## wherein R 5 is lower-alkyl, or lower-cycloalkyl, and wherein each R 6 is independently selected from hydrogen, lower-alkyl or lower-cycloalkyl; R 2 is a group of the formula ##STR47## wherein each R 7 and R 8 are independently selected from hydrogen, phenyl, or lower-alkyl, wherein R 9 is selected from the group consisting of phenyl, thienyl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl, 4,5-dihydro-5-oxo-1H-tetrazol-1-yl substituted in the 4-position by a group selected from lower-alkyl, phenyl-lower-alkyl or phenyl, and substituted phenyl in which the substituents are selected from halogen, lower-alkoxy, lower-alkyl, or combinations thereof, and wherein n is an integer of from 0 to 7; R 3 is selected from a group consisting of hydrogen, methoxy-methyl, and a carboxylate radical represented by the formula ##STR48## wherein R 10 is selected from lower-alkyl, phenyl-lower-alkyl or lower-alkoxy-lower-alkyl.
Claim 101
Independent Claim
115 words
A method for providing analgesia in a mammal comprising administering to such a mammal an analgesically effective amount of a compound of the formula ##STR49## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl or 2-substituted phenyl wherein said 2-substituent is selected from halogen, lower-alkoxy or lower-alkyl; R 1 is selected from the group consisting of methoxymethyl, 1-methoxyethyl, thienyl and furanyl; R 2 is selected from the group consisting of benzyl, 2-phenylethyl, 2-(2-fluorophenyl)-ethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, 2-(3-thienyl)-ethyl, 2-(2-thienyl)ethyl, 2-(4-methylthiazol-5-yl)ethyl, 2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl, and 2-methyl-1-propyl; R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group; and R 4 is selected from hydrogen or methyl.
Claim 102
Independent Claim
115 words
A method for providing analgesia in a mammal comprising administering to such a mammal an analgesically effective amount of a compound of the formula ##STR49## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl or 2-substituted phenyl wherein said 2-substituent is selected from halogen, lower-alkoxy or lower-alkyl; R 1 is selected from the group consisting of methoxymethyl, 1-methoxyethyl, thienyl and furanyl; R 2 is selected from the group consisting of benzyl, 2-phenylethyl, 2-(2-fluorophenyl)-ethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, 2-(3-thienyl)-ethyl, 2-(2-thienyl)ethyl, 2-(4-methylthiazol-5-yl)ethyl, 2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl, and 2-methyl-1-propyl; R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group; and R 4 is selected from hydrogen or methyl.
Claim 103
Independent Claim
80 words
A method for providing analgesia in a mammal comprising administering to such a mammal an analgesically effective amount of a compound of the formula ##STR50## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl; R 1 is methoxymethyl or furanyl; R 2 is selected from the group consisting of 2-phenylethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, and 2-(2-thienyl)ethyl; and R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group.
Claim 104
Independent Claim
80 words
A method for providing analgesia in a mammal comprising administering to such a mammal an analgesically effective amount of a compound of the formula ##STR50## optically active isomeric forms thereof, and/or pharmaceutically acceptable acid addition salts thereof, in which formula: R is phenyl; R 1 is methoxymethyl or furanyl; R 2 is selected from the group consisting of 2-phenylethyl, 1-phenyl-2-propyl, 2-phenyl-1-propyl, and 2-(2-thienyl)ethyl; and R 3 is selected from the group consisting of hydrogen, methoxymethyl and a methyl carboxylate group.
Claim 105
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 106
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 107
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-(2-phenylethyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 108
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-(2-phenylethyl)-4-methoxymethyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 109
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 110
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-(2-phenylethyl)-4-(N-phenyl-2-furoylamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 111
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-(2-phenylethyl)-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 112
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-(2-phenylethyl)-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 113
Dependent Claim
19 words
A method according to claim 92, wherein said compound comprises 1-(2-phenyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 114
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 115
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)-2-methoxypropionamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 116
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(2-phenylethyl)-4-[N-(2-fluorophenyl)-3-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 117
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(1-phenyl-2-propyl)-4-[N-(2-methoxyphenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 118
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(3-thienyl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 119
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(4-methylthiazol-5-yl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 120
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(2-fluorophenyl)ethyl]-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 121
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(1-phenyl-2-propyl)-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 122
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-benzyl-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 123
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(2-methyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 124
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(3-thienyl)ethyl]-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 125
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(3-phenyl-1-propyl)-4-methoxycarbonyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 126
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 127
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-furoylamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 128
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 129
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 130
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-methoxyphenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 131
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 132
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenylmethoxyacetamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 133
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-(N-phenyl-2-methoxypropionamido)piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 134
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 135
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises trans-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 136
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 137
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-methoxypropionamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 138
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-methoxyphenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 139
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 140
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-chlorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 141
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-[2-(2-thienyl)ethyl]-3-methyl-4-[N-(2-fluorophenyl)-2-furoylamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 142
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises cis-1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 143
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises trans-1-(2-phenylethyl)-3-methyl-4-[N-(2-fluorophenyl)methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 144
Dependent Claim
19 words
A method according to claim 91, wherein said compound comprises 1-(2-phenylethyl)-4-[N-(2-methoxyphenyl)-2-methoxyacetamido]piperidine or a pharmaceutically acceptable acid addition salt thereof.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-04-21 | 1989-10-21 | 1990-04-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-04-21 | 1993-10-21 | 1994-04-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-04-21 | 1997-10-21 | 1998-04-22 | $7700.00 | Window Closed / Lapsed |