US4737493A
Expired / Lapsed
US
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7-((substituted)amino)-8-((substituted)carbonyl)-methylamino)-1-oxaspiro(4,5)decanes as analgesic agents
Assignee: Warner Lambert Co LLC
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Filing: 1986-06-09
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Granted: 1988-04-12
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Expires: 2006-06-09
Abstract
Abstract Substituted phenoxy-, 1-, and 2-naphthalenyloxy-, indenyl-, indolyl-, benzofuranyl-, and benzo[b]thiofuranylcarboxamides of 7,8-(substituted-diamino)-1-oxaspiro[4.5]decanes are useful as analgesic agents. A method of making the compounds, pharmaceutical compositions employing the compounds, and a method of alleviating pain in warm-blooded animals are also disclosed.
Inventors
- 👤 David C. Horwell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 08:58
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/12; A; A61; A61P; A61P25/00; A61P25/04; C07D307/00; C07D307/94; C07D409/00; C07D409/02; C07D409/12
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
235 words
A compound having the structure ##STR17## wherein n is an integer of from one to six; either of X or Y is oxygen and the other is --CH 2 --; R 1 is selected from ##STR18## where R 4 and R 5 are independently hydrogen, fluorine, chlorine, bromine, nitro, trifluoromethyl, alkyl of from one to six carbon atoms, alkoxy of from one to six carbon atoms, or aryl; ##STR19## where R 6 is hydrogen, fluorine, chlorine, alkyl of from one to six carbon atoms, or aryl; Z is --CH 2 --, --O--, --S--, or --NR 7 -- where R 7 is hydrogen, alkanoyl of from two to six carbon atoms, or alkyl of from one to six carbon atoms; ##STR20## where R 8 and R 9 are independently hydrogen, fluorine, chlorine, bromine , alkyl of from one to six carbon atoms, or alkoxy of from one to four carbon atoms; or ##STR21## where R 8 and R 9 are as defined above; R 2 is methyl and R 3 is hydrogen; alkyl of from one to six carbon atoms,; ##STR22## --CH 2 --CH═CH 2 , --CH 2 C.tbd.CH; ##STR23## where R 10 is alkyl of from one to four carbon atoms; or where R 2 and R 3 when taken together with the nitrogen atom to which they are attached, form a pyrrolidinyl, piperidinyl, or hexahydro-1H-azepinyl ring; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
235 words
A compound having the structure ##STR17## wherein n is an integer of from one to six; either of X or Y is oxygen and the other is --CH 2 --; R 1 is selected from ##STR18## where R 4 and R 5 are independently hydrogen, fluorine, chlorine, bromine, nitro, trifluoromethyl, alkyl of from one to six carbon atoms, alkoxy of from one to six carbon atoms, or aryl; ##STR19## where R 6 is hydrogen, fluorine, chlorine, alkyl of from one to six carbon atoms, or aryl; Z is --CH 2 --, --O--, --S--, or --NR 7 -- where R 7 is hydrogen, alkanoyl of from two to six carbon atoms, or alkyl of from one to six carbon atoms; ##STR20## where R 8 and R 9 are independently hydrogen, fluorine, chlorine, bromine , alkyl of from one to six carbon atoms, or alkoxy of from one to four carbon atoms; or ##STR21## where R 8 and R 9 are as defined above; R 2 is methyl and R 3 is hydrogen; alkyl of from one to six carbon atoms,; ##STR22## --CH 2 --CH═CH 2 , --CH 2 C.tbd.CH; ##STR23## where R 10 is alkyl of from one to four carbon atoms; or where R 2 and R 3 when taken together with the nitrogen atom to which they are attached, form a pyrrolidinyl, piperidinyl, or hexahydro-1H-azepinyl ring; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
11 words
A compound as defined in claim 1 wherein n is one.
Claim 4
Dependent Claim
28 words
A compound as defined in claim 1 wherein R 2 and R 3 taken together with the nitrogen atom to which they are attached form a pyrrolidinyl ring.
Claim 5
Dependent Claim
22 words
A compound as defined in claim 1 wherein R 1 is ##STR24## where R 4 and R 5 are as defined therein.
Claim 6
Dependent Claim
18 words
A compound as defined by claim 1 wherein ##STR25## where R 6 and Z are as defined therein.
Claim 7
Dependent Claim
13 words
A compound as defined by claim 5 wherein Z is --CH 2 --.
Claim 8
Dependent Claim
11 words
A compound as defined by claim 5 wherein Z is oxygen.
Claim 9
Dependent Claim
11 words
A compound as defined by claim 5 wherein Z is sulfur.
Claim 10
Dependent Claim
20 words
A compound as defined by claim 5 wherein Z is --NR 7 -- where R 7 is as defined therein.
Claim 11
Dependent Claim
22 words
A compound as defined by claim 1 wherein R 1 is ##STR26## where R 8 and R 9 are as defined therein.
Claim 12
Dependent Claim
11 words
A compound as defined by claim 4 having the name N-methyl-N-[7-(methyl-2-propynylamino)-1-oxaspiro[4.5]dec-8-yl]phenoxyacetamide.
Claim 13
Dependent Claim
11 words
A compound as defined by claim 7 having the name N-[7-[(cyclopropylmethyl)methylamino]-1-oxaspiro[4.5]dec-8-yl]-N,2-dimethylbenzo[b]furan-3-acetamide.
Claim 14
Dependent Claim
11 words
A compound as defined by claim 9 having the name N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-1H-indole-3-acetamide.
Claim 15
Dependent Claim
11 words
A compound as defined by claim 4 having the name N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-2-(3-nitrophenoxy)acetamide.
Claim 16
Dependent Claim
11 words
A compound as defined by claim 4 having the name N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-2-(3-trifluoromethylphenoxy)acetamide.
Claim 17
Dependent Claim
11 words
A compound as defined by claim 7 having the name N-methyl-N-[7[(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-2-bemzo[b]furanacetamide.
Claim 18
Dependent Claim
11 words
A compound as defined by claim 7 having the name N-methyl-N-[7[(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-3-bemzo[b]furanacetamide.
Claim 19
Dependent Claim
11 words
A compound as defined by claim 7 having the name N-methyl-N-[7[(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]-4-bemzo[b]furanacetamide.
Claim 20
Dependent Claim
11 words
A compound as defined by claim 6 having the name N-methyl-N-[7-(methyl-2-propenylamino)-1-oxaspiro[4.5]dec-8-yl]-1H-indene-3-acetamide.
Claim 21
Dependent Claim
11 words
A compound as defined by claim 4 having the name 2-(4-fluorophenoxy)-N-methyl-N-[7-[methyl-(2-phenylethyl)amino]-1-oxaspiro[4.5]dec-8-yl]acetamide.
Claim 22
Dependent Claim
11 words
A compound as defined by claim 4 having the name 2-(3,4-dichlorophenoxy)-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]acetamide.
Claim 23
Dependent Claim
11 words
A compound as defined by claim 4 having the name 2-(2,6-dichlorophenoxy)-N-methyl-N-[7-(-1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]acetamide.
Claim 24
Dependent Claim
11 words
A compound as defined by claim 4 having the name 2-(3,5-dichlorophenoxy)-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]acetamide.
Claim 25
Dependent Claim
11 words
A compound as defined by claim 6 having the name N-methyl-N-[7-(1-pyrrolodinyl)-1-oxaspiro[4.5]dec-8-yl]-3-indeneacetamide.
Claim 26
Dependent Claim
11 words
A compound as defined by claim 9 having the name N-[7-(dimethylamino)-1-oxaspiro-[4.5]dec-8-yl]-N-methyl-1H-indole-3-acetamide.
Claim 27
Dependent Claim
11 words
A compound as defined by claim 4 having the name 2-(4-fluorophenoxy)-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]acetamide.
Claim 28
Dependent Claim
11 words
A compound as defined by claim 10 having the name N-methyl-2-(1-naphthalenyloxy)-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]acetamide.
Claim 29
Dependent Claim
38 words
A method of alleviating pain in a warm-blooded animal comprising administering to said animal in need of such treatment an analgesically effective amount of a compound as defined by claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 30
Dependent Claim
11 words
A compound as defined by claim 10 having the name N-methyl-N-[7-[methyl[2-(2-thienyl)ethyl]amino]-1-oxaspiro[4.5]dec-8-yl]-2-(1-naphthalenyloxy)acetamide.
Claim 31
Dependent Claim
31 words
A pharmaceutical composition useful for treating pain in a warm-blooded animal comprising an analgesically effective amount of a compound as defined by claim 1 in combination with a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
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US4145435A
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US4212878A
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US4359476A
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US4360531A
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US4438130A
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-04-12 | 1991-10-12 | 1992-04-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-04-12 | 1995-10-12 | 1996-04-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-04-12 | 1999-10-12 | 2000-04-12 | $7700.00 | Window Closed / Lapsed |