US4493846A
Expired / Lapsed
US
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Bicyclooctane derivatives
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1981-03-13
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Granted: 1985-01-15
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Expires: 2001-03-13
Abstract
Abstract A compound of the formula ##STR1## wherein X 1 is a free or esterified carboxyl group, a hydroxymethyl group, a cyano group, a group of the formula: ##STR2## (R a and R b are each independently a hydrogen atom, a C 1 -C 4 alkyl group, a C 3 -C 7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C 1 -C 4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7-membered saturated heterocyclic group) or a group of the formula: ##STR3## (R a and R b are each as defined above), Y is an ethylene group or a vinylene group, R 1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R 2 is a hydrogen atom or R 1 and R 2 , when taken together, means a single linkage to form a double bond between the carbon atoms which they are linked, R 3 is a hydroxyl group or a protected hydroxyl group, R 4 is a hydrogen atom or a C 1 -C 4 alkyl group, R 5 is a hydrogen atom, a C 3 -C 8 alkenyl group, a C 3 -C 8 alkynyl group, a C 1 -C 8 alkyl group, a C 3 -C 7 cycloalkyl group or a group of the formula: --(CH 2 ) n --B (n is 1 or 2 and B is a C 1 -C 4 alkoxyl group, a C 3 -C 7 cycloalkyl group, or a phenyl or phenoxy group optionally substituted with a halogen atom, a C 1 -C 4 alkyl group, a trifluoromethyl group or a C 1 -C 4 alkoxyl group), A is a group of either one of the formulae: ##STR4## (R 6 and R 7 are each independently a hydrogen atom or a C 1 -C 4 alkyl group) and ##STR5## m 1 is 1 or 2 and m 2 is 0, 1 or 2, and the non-toxic pharmaceutically acceptable salts threreof. Said compounds have strong anti-ulcerogenic activity and are useful in treatment of gastraintestinal ulcer.
Inventors
- 👤 Keiichi Ono
- 👤 Akihiko Sugie
- 👤 Hajime Kawakami
- 👤 Shunsuke Sami
- 👤 Atsuyuki Kojima
- 👤 Junki Katsube
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 12:24
CPC Classifications
C; C07; C07C; C07C255/00; C07C29/00; C07C29/09; C07C29/095; C07C29/128; C07C29/1285; C07C35/00; C07C35/22; C07C35/23; C07C35/32; C07C405/00; C07C405/005; C07C405/0075; C07C405/0083; C07C43/00; C07C43/02; C07C43/18; C07C43/196; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/30; C07D211/32; C07B; C07B2200/00; C07B2200/07; C07B2200/09; C07C2602/00; C07C2602/02; C07C2602/14; C07C2602/24
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
263 words
A compound of the formula ##STR30## wherein X 1 is COOH, C 1 -C 4 alkoxycarbonyl, phenoxycarbonyl, phenylalkyloxycarbonyl, (C 1 -C 4 alkoxy)methoxycarbonyl, (C 2 -C 5 alkanoyloxy)methoxycarbonyl, (C 3 -C 7 cycloalkyloxy)carbonyl, phenylcarbonylmethoxycarbonyl, or (hydroxy C 1 -C 4 alkoxy)carbonyl, Y is ethylene or vinylene, R 1 is --H, --OH, --OC 1 -C 4 alkanoyl, --O--benzoyl, or --O--(C 1 -C 4 alkoxy)alkyl, R 2 is H or R 1 or R 2 , when taken together, are a single linkage forming a double bond between the carbon atoms to which they are linked, R 3 is OH, --OC 1 -C 4 alkanoyl, --O--benzoyl, or --O(C 1 -C 4 alkoxy)alkyl, R 4 is H or C 1 -C 4 alkyl, R 5 is H, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl or a group of the formula --(CH 2 ) n --B where n is 1 or 2 and B is C 1 -C 4 alkoxy, C 3 -C 7 cycloalkyl, phenyl, phenoxy, phenyl substituted with any of a halogen atom, C 1 -C 4 alkyl, CF 3 , or C 1 -C 4 alkoxy; or phenoxy substituted with any of a halogen atom, C 1 -C 4 alkyl, CF 3 , or C 1 -C 4 alkoxy; A is ##STR31## wherein R 6 and R 7 are each independently H or C 1 -C 4 alkyl; m 1 is 1 or 2, and m 2 is 0, 1 or 2, and an effective, anti-ulcerogenic non-toxic pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
263 words
A compound of the formula ##STR30## wherein X 1 is COOH, C 1 -C 4 alkoxycarbonyl, phenoxycarbonyl, phenylalkyloxycarbonyl, (C 1 -C 4 alkoxy)methoxycarbonyl, (C 2 -C 5 alkanoyloxy)methoxycarbonyl, (C 3 -C 7 cycloalkyloxy)carbonyl, phenylcarbonylmethoxycarbonyl, or (hydroxy C 1 -C 4 alkoxy)carbonyl, Y is ethylene or vinylene, R 1 is --H, --OH, --OC 1 -C 4 alkanoyl, --O--benzoyl, or --O--(C 1 -C 4 alkoxy)alkyl, R 2 is H or R 1 or R 2 , when taken together, are a single linkage forming a double bond between the carbon atoms to which they are linked, R 3 is OH, --OC 1 -C 4 alkanoyl, --O--benzoyl, or --O(C 1 -C 4 alkoxy)alkyl, R 4 is H or C 1 -C 4 alkyl, R 5 is H, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl or a group of the formula --(CH 2 ) n --B where n is 1 or 2 and B is C 1 -C 4 alkoxy, C 3 -C 7 cycloalkyl, phenyl, phenoxy, phenyl substituted with any of a halogen atom, C 1 -C 4 alkyl, CF 3 , or C 1 -C 4 alkoxy; or phenoxy substituted with any of a halogen atom, C 1 -C 4 alkyl, CF 3 , or C 1 -C 4 alkoxy; A is ##STR31## wherein R 6 and R 7 are each independently H or C 1 -C 4 alkyl; m 1 is 1 or 2, and m 2 is 0, 1 or 2, and an effective, anti-ulcerogenic non-toxic pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
39 words
A compound of the formula ##STR32## wherein X 1 , Y, R 1 , R 2 , R 3 , R 4 and R 5 are each as defined in claim 1, and their non-toxic pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
23 words
A compound of the formula ##STR33## wherein X 1 , Y, R 4 and R 5 are each as defined in claim 1.
Claim 5
Dependent Claim
12 words
The compound according to claim 3, wherein Y is a vinylene group.
Claim 6
Dependent Claim
17 words
The compound according to claim 3, wherein R 5 is a C 1 -C 8 alkyl group.
Claim 7
Dependent Claim
45 words
The compound according to claim 3, wherein R 5 is a group of the formula: --CH 2 --D--G, wherein D is an oxygen atom or a single bond, and G is a phenyl group optionally substituted with halogen, C 1 -C 4 alkyl or trifluoromethyl.
Claim 8
Dependent Claim
7 words
2β-(3'α-hydroxy-trans-1'-octenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 9
Dependent Claim
7 words
2β-(3'α-hydroxy-trans-1'-octenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 10
Dependent Claim
7 words
2β-(3'α-hydroxy-trans-1'-octenyl)-3α-hydroxy-7α-(o-carboxybenzyloxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 11
Dependent Claim
7 words
2β-(3'α-hydroxy-trans-1'-octenyl)-3α-hydroxy-7α-(o-carboxybenzyloxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 12
Dependent Claim
7 words
2β-(3'α-hydroxy-4',4'-dimethyl-trans-1'-octenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 13
Dependent Claim
7 words
2β-(3'α-hydroxy-4',4'-dimethyl-trans-1'-octenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 14
Dependent Claim
7 words
2β-(3'α-hydroxy-3'β-methyl-trans-1'-octenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 15
Dependent Claim
7 words
2β-(3'α-hydroxy-3'β-methyl-trans-1'-octenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 16
Dependent Claim
7 words
2β-(3'α-hydroxy-octyl)-3.alpha.-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 17
Dependent Claim
7 words
2β-(3'α-hydroxy-octyl)-3.alpha.-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 18
Dependent Claim
7 words
2β-[4'-(p-fluorophenoxy)-3'.alpha.-hydroxy-trans-1'-butenyl]-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 19
Dependent Claim
7 words
2β-[4'-(p-fluorophenoxy)-3'.alpha.-hydroxy-trans-1'-butenyl]-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 20
Dependent Claim
7 words
2β-[4'-(p-fluorophenoxy)-3'α-hydroxy-butyl]-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 21
Dependent Claim
7 words
2β-[4'-(p-fluorophenoxy)-3'α-hydroxy-butyl]-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 22
Dependent Claim
7 words
2β-(4'-phenoxy-3'α-hydroxy-trans-1'-butenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 23
Dependent Claim
7 words
2β-(4'-phenoxy-3'α-hydroxy-trans-1'-butenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 24
Dependent Claim
7 words
2β-(4'-phenyl-3'α-hydroxy-1'-butenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 25
Dependent Claim
7 words
2β-(4'-phenyl-3'α-hydroxy-1'-butenyl)-3α-hydroxy-7α-(3"-carboxypropoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 26
Dependent Claim
7 words
2β-(3'α-hydroxy-trans-1'-octenyl)-3α-hydroxy-7α-(3"-carboxy-trans-2"-propenoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 27
Dependent Claim
7 words
2β-(3'α-hydroxy-trans-1'-octenyl)-3α-hydroxy-7α-(3"-carboxy-trans-2"-propenoxy)cis-bicyclo[3,3,0]octane, and its stereoisomers (3'β and/or 7β).
Claim 28
Dependent Claim
19 words
A pharmaceutically acceptable salt of a compound as claimed in claim 1, wherein X 1 is a carboxyl group.
Claim 29
Dependent Claim
52 words
The compound according to claim 4, wherein X 1 is COOH, C 1 -C 4 alkoxycarbonyl, phenoxycarbonyl, phenylalkyloxycarbonyl, (C 1 -C 4 alkoxy)methoxycarbonyl, (C 2 -C 5 alkanoyloxy)methoxycarbonyl, (C 3 -C 7 cycloalkyloxy)carbonyl, phenylcarbonylmethoxycarbonyl, or (hydroxy C 1 -C 4 alkoxy)carbonyl, and R 5 is a C 1 -C 8 alkyl group.
Claim 30
Dependent Claim
85 words
The compound according to claim 4, wherein X 1 is COOH, C 1 -C 4 alkoxycarbonyl, phenoxycarbonyl, phenylalkyloxycarbonyl, (C 1 -C 4 alkoxy)methoxycarbonyl, (C 2 -C 5 alkanoyloxy)methoxycarbonyl, (C 3 -C 7 cycloalkyloxy)carbonyl, phenylcarbonylmethoxycarbonyl, or (hydroxy C 1 -C 4 alkoxy)carbonyl, and R 5 is a group of the formula --CH 2 --D--G where D is an oxygen atom or a single bond, and G is a phenyl group optionally substituted with halogen, C 1 -C 4 alkyl, trifluoromethyl, or C 1 -C 4 alkoxyl.
Claim 31
Dependent Claim
26 words
A pharmaceutical composition for the treatment of ulcers comprising an anti-ulcerogenic effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier or diluent.
References Cited (Backward Citations)
US4096337A
Cited
GB2017699A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-01-15 | 1988-07-16 | 1989-01-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-01-15 | 1992-07-16 | 1993-01-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-01-15 | 1996-07-16 | 1997-01-15 | $7700.00 | Window Closed / Lapsed |