US4179567A
Expired / Lapsed
US
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2-Aryltropane compounds
Assignee: STWB Inc
•
Filing: 1978-04-10
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Granted: 1979-12-18
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Expires: 1998-04-10
Abstract
Abstract Compounds of the tropane (8-azabicyclo[3.2.1]octane) series having an aromatic substiutent in the 2-position and a carboalkoxy group in the 3-position are prepared by reacting a tropane-3-carboxylate having a double bond in the 2,3-position with an aryl Grignard reagent. Transformations of the substituent on nitrogen are subsequently effected. Compounds where the 3-carboalkoxy group is in the exo configuration possess hypoglycemic activity, and those where the 3-carboalkoxy group is in the endo configuration possess narcotic antagonist activity.
Inventors
- 👤 Robert L. Clarke
- 👤 Sol J. Daum
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 22:10
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
42 words
A compound of the formula: ##STR6## wherein: R is selected from the group consisting of: hydrogen, alkyl of 1-8 carbon atoms optionally interrupted by an oxygen atom, phenylalkyl where alkyl has 1-3 carbon atoms, cyclopropylmethyl, hydroxyalkyl of 2-4 carbon atoms, and 2.
Claim 2
Dependent Claim
42 words
A compound of the formula: ##STR6## wherein: R is selected from the group consisting of: hydrogen, alkyl of 1-8 carbon atoms optionally interrupted by an oxygen atom, phenylalkyl where alkyl has 1-3 carbon atoms, cyclopropylmethyl, hydroxyalkyl of 2-4 carbon atoms, and 2.
Claim 3
Dependent Claim
27 words
2-diethoxyethyl; Ar is selected from the group consisting of: phenyl, benzyl, 3-hydroxyphenyl, 3-methoxyphenyl, and 2-thienyl; and R' is hydrogen or alkyl of 1 to 3 carbon atoms;
Claim 4
Dependent Claim
27 words
2-diethoxyethyl; Ar is selected from the group consisting of: phenyl, benzyl, 3-hydroxyphenyl, 3-methoxyphenyl, and 2-thienyl; and R' is hydrogen or alkyl of 1 to 3 carbon atoms;
Claim 5
Dependent Claim
27 words
or a pharmaceutically acceptable acid-addition salt thereof. 2. A compound according to claim 1 wherein the COOR' group is in the exo configuration and Ar is phenyl.
Claim 6
Dependent Claim
29 words
A compound according to claim 1 wherein the COOR' group is in the exo configuration, R is methyl, R' is lower-alkyl of 1-3 carbon atoms and Ar is phenyl.
Claim 7
Dependent Claim
6 words
Methyl (exo,exo)-8-benzyl-2-phenyl-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 2.
Claim 8
Dependent Claim
6 words
Methyl (exo,exo)-2-phenyl-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 2.
Claim 9
Dependent Claim
6 words
Methyl (exo,exo)-8-cyclopropylmethyl-2-phenyl-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 2.
Claim 10
Dependent Claim
6 words
Methyl (exo,exo)-8-methyl-2-(3-methoxyphenyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 1.
Claim 11
Dependent Claim
6 words
Methyl (exo,exo)-8-methyl-2-benzyl-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 1.
Claim 12
Dependent Claim
6 words
(exo,exo)-8-Methyl-2-phenyl-8-azabicyclo[3.2.1]octane-3-carboxylic acid, according to claim 2.
Claim 13
Dependent Claim
19 words
A compound according to claim 1 wherein the COOR' group is in the exo configuration and Ar is 2-thienyl.
Claim 14
Dependent Claim
33 words
A compound according to claim 1 wherein the COOR' group is in the exo configuration, R is alkyl of 1-8 carbon atoms, R' is alkyl of 1-3 carbon atoms and Ar is 2-thienyl.
Claim 15
Dependent Claim
6 words
Methyl (exo,exo)-8-methyl-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 11.
Claim 16
Dependent Claim
6 words
Methyl (exo,exo)-8-(1-pentyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 11.
Claim 17
Dependent Claim
6 words
Methyl (exo,exo)-8-(1-heptyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 11.
Claim 18
Dependent Claim
6 words
Methyl (exo,exo)-8-[1-(2-ethylbutyl)]-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 11.
Claim 19
Dependent Claim
6 words
Ethyl (exo,exo)-8-(1-pentyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 11.
Claim 20
Dependent Claim
6 words
Methyl (exo,exo)-8-(2-propyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 11.
Claim 21
Dependent Claim
6 words
Methyl (exo,exo)-8-(1-butyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 11.
Claim 22
Dependent Claim
22 words
A compound according to claim 1 wherein the COOR' group is in the exo configuration, R is hydrogen and Ar is 2-thienyl.
Claim 23
Dependent Claim
6 words
Methyl (exo,exo)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 19.
Claim 24
Dependent Claim
6 words
(exo,exo)-2-(2-Thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid, according to claim 19.
Claim 25
Dependent Claim
6 words
Ethyl (exo,exo)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 19.
Claim 26
Dependent Claim
6 words
Methyl (exo,exo)-8-(2-hydroxyethyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 10.
Claim 27
Dependent Claim
6 words
Methyl (exo,exo)-8-(2-ethoxyethyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 10.
Claim 28
Dependent Claim
6 words
Methyl (exo,exo)-8-(2-phenylethyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 10.
Claim 29
Dependent Claim
6 words
Methyl (exo,exo)-8-(2,2-diethoxyethyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 10.
Claim 30
Dependent Claim
2 words
Methyl (exo,exo)-8-(2-cyanoethyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate.
Claim 31
Dependent Claim
2 words
Methyl (exo,exo)-8-(2-cyanoethyl)-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate.
Claim 32
Dependent Claim
2 words
Methyl (exo,exo)-3-methoxycarbonyl-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-8-acetate.
Claim 33
Dependent Claim
2 words
Methyl (exo,exo)-3-methoxycarbonyl-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-8-acetate.
Claim 34
Dependent Claim
2 words
Methyl (exo,exo)-8-tetrahydrofurfuryl-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate.
Claim 35
Dependent Claim
2 words
Methyl (exo,exo)-8-tetrahydrofurfuryl-2-(2-thienyl)-8-azabicyclo[3.2.1]octane-3-carboxylate.
Claim 36
Dependent Claim
2 words
Methyl (exo,exo)-8-methyl-2-(1H-2-pyrrolyl)-8-azabicyclo[3.2.1]octane-3-carboxylate.
Claim 37
Dependent Claim
2 words
Methyl (exo,exo)-8-methyl-2-(1H-2-pyrrolyl)-8-azabicyclo[3.2.1]octane-3-carboxylate.
Claim 38
Dependent Claim
19 words
A compound according to claim 1 wherein the COOR' group is in the endo configuration and Ar is phenyl.
Claim 39
Dependent Claim
6 words
Methyl (2-exo-3-endo)-8-methyl-2-phenyl-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 31.
Claim 40
Dependent Claim
6 words
Methyl (2-exo-3-endo)-2-phenyl-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 31.
Claim 41
Dependent Claim
6 words
Methyl (2-exo-3-endo)-2-phenyl-8-cyclopropylmethyl-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 31.
Claim 42
Dependent Claim
6 words
(2-exo-3-endo)-8-Methyl-2-phenyl-8-azabicyclo[3.2.1]octane-3-carboxylic acid, according to claim 31.
Claim 43
Dependent Claim
6 words
Methyl (2-exo-3-endo)-8-methyl-2-(3-methoxyphenyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 1.
Claim 44
Dependent Claim
6 words
Methyl (2-exo-3-endo)-8-methyl-2-benzyl-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 1.
Claim 45
Dependent Claim
6 words
Methyl (2-exo-3-endo)-8-methyl-2-(3-hydroxyphenyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 1.
Claim 46
Dependent Claim
6 words
Methyl (2-exo-3-endo)-2-(3-hydroxyphenyl)-8-azabicyclo[3.2.1]octane-3-carboxylate, according to claim 1.
Claim 47
Dependent Claim
36 words
A process for preparing a compound according to claim 1 which comprises reacting a compound of the formula ##STR7## with ArMgX, where X is chlorine, bromine or iodine in an inert organic solvent under anhydrous conditions.
Claim 48
Dependent Claim
12 words
A process according to claim 40 wherein R is methyl or benzyl.
Claim 49
Dependent Claim
49 words
A process for preparing a compound according to claim 1 where R is other than hydrogen which comprises reacting a compound according to claim 1 where R is hydrogen with RX, where X is chlorine, bromine or iodine, in an inert organic solvent in the presence of a base.
References Cited (Backward Citations)
US3073831A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-17 | 1983-06-18 | 1983-12-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-17 | 1987-06-18 | 1987-12-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-17 | 1991-06-18 | 1991-12-18 | $7700.00 | Window Closed / Lapsed |