US4062967A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Bis-guanidino-alkane compounds
Assignee: Smith Kline & French Laboratories Ltd
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Filing: 1976-04-20
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Granted: 1977-12-13
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Expires: 1996-04-20
Abstract
Abstract The compounds are C2-C8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N''-disubstituted guanidino), N-(N'-substituted thioureido), N-(nitromethylene amidino) or S-(N-substituted isothioureido)groups. Two compounds of the invention are 1,3-bis[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)isothioureido]p ropane. The compounds of this invention are inhibitors of H-2 histamine receptors.
Inventors
- 👤 Graham John Durant
- 👤 Charon Robin Ganellin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 19:32
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
162 words
A compound of the formula: ##STR18## wherein R 1 and R 2 , which may be the same or different, each represent a grouping of the structure: Het -- (CH.sub.2).sub.m Z -- (CH.sub.2).sub.n -- wherein Het is imidazole which is attached at a ring carbon and which is optionally substituted by lower alkyl or halogen; Z is sulphur or a methylene group; m is 0, 1 or 2; n is 2 or 3 and the sum of m and n is 3, 4 or when Y is other than hydroxyl, 2; X 1 and X 2 , which may be the same or different, are each NY wherein Y is hydroxy, cyano, CONH 2 or SO 2 R 3 or one of X 1 and X 2 is NH or N-lower alkyl; R 3 is lower alkyl, phenyl, tolyl, trifluoromethyl or amino; W is NH; and q is an integer from 2 to 8; or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
162 words
A compound of the formula: ##STR18## wherein R 1 and R 2 , which may be the same or different, each represent a grouping of the structure: Het -- (CH.sub.2).sub.m Z -- (CH.sub.2).sub.n -- wherein Het is imidazole which is attached at a ring carbon and which is optionally substituted by lower alkyl or halogen; Z is sulphur or a methylene group; m is 0, 1 or 2; n is 2 or 3 and the sum of m and n is 3, 4 or when Y is other than hydroxyl, 2; X 1 and X 2 , which may be the same or different, are each NY wherein Y is hydroxy, cyano, CONH 2 or SO 2 R 3 or one of X 1 and X 2 is NH or N-lower alkyl; R 3 is lower alkyl, phenyl, tolyl, trifluoromethyl or amino; W is NH; and q is an integer from 2 to 8; or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
31 words
A compound according to claim 1 wherein X 1 and X 2 , which may be the same or different, are each NY and wherein y is defined in claim 1.
Claim 4
Dependent Claim
15 words
A compound according to claim 1 wherein R 1 and R 2 are the same.
Claim 5
Dependent Claim
17 words
A compound according to claim 1 wherein Z is sulphur m is 1 and n is 2.
Claim 6
Dependent Claim
17 words
A compound according to claim 1 wherein Het is imidazole or imidazole substituted by methyl or halogen.
Claim 7
Dependent Claim
15 words
A compound according to claim 1 wherein X 1 and X 2 are the same.
Claim 8
Dependent Claim
15 words
A compound according to claim 6 wherein X 1 and X 2 are both NCN.
Claim 9
Dependent Claim
13 words
A compound according to claim 1 wherein q is from 2 to 4.
Claim 10
Dependent Claim
10 words
A compound according to claim 8 wheren q is 3.
Claim 11
Dependent Claim
10 words
A compound according to claim 1, said compound being 1,3-bis-[N'-cyano-N"-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane.
Claim 12
Dependent Claim
51 words
A pharmaceutical composition to inhibit H-2 histamine receptors, said H-2 histamine receptors being those histamine receptors which are not inhibited by mepyramine but are inhibited by burimamide, comprising, in an effective amount to inhibit H-2 histamine receptors, a compound of claim 1 in combination with a pharmaceutically acceptable diluent or carrier.
Claim 13
Dependent Claim
56 words
A method of inhibiting H-2 histamine receptors, said H-2 histamine receptors being those histamine receptors which are not inhibited by mepyramine but are inhibited by burimamide, which comprises administering to an animal in need of inhibition of said H-2 histamine receptors in an effective amount to inhibit said H-2 histamine receptors a compound of claim 1.
References Cited (Backward Citations)
US3932443A
Cited
BE816850A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-12 | 1981-06-13 | 1981-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-12 | 1985-06-13 | 1985-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-12 | 1989-06-13 | 1989-12-13 | $7700.00 | Window Closed / Lapsed |