Patent US4024260A successfully refreshed from Google Patents.
US4024260A
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Ethylene derivatives
Assignee: Smith Kline & French Laboratories Ltd
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Filing: 1975-11-11
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Granted: 1977-05-17
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Expires: 1995-11-11
Abstract
Abstract The compounds are ethylene derivatives which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A compound of this invention is 1-nitro-2-methylamino-2-[2-((4-methyl-5-imidazolyl)methylthio)-ethylam ino[ethylene.
Inventors
- 👤 Graham John Durant
- 👤 John Colin Emmett
- 👤 Charon Robin Ganellin
- 👤 Hunter Douglas Prain
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 10:19
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/02; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/32; C07D249/00; C07D249/02; C07D249/08; C07D261/00; C07D261/02; C07D261/06; C07D261/08; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/08; C07D285/12; C07D285/125; C07D285/135
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
134 words
A pharmaceutical composition to inhibit H-2 histamine receptors comprising a pharmaceutical carrier and in an effective amount to inhibit said receptors a heterocyclic compound of the formula: ##STR8## wherein X and Y, which may be the same or different, are hydrogen, nitro, cyano or SO 2 Ar but are not both hydrogen; R is hydrogen, lower alkyl or Het(CH 2 ) m Z(CH 2 ) n ; Z is sulphur; m is 0, 1 or 2 and n is 2 or 3, provided that the sum of m and n is 3 or 4; Het is a pyridine ring which ring is optionally substituted by lower alkyl, hydroxyl, halogen or amino; and Ar is an aryl group such as phenyl optionally substituted by halogen or methyl or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
134 words
A pharmaceutical composition to inhibit H-2 histamine receptors comprising a pharmaceutical carrier and in an effective amount to inhibit said receptors a heterocyclic compound of the formula: ##STR8## wherein X and Y, which may be the same or different, are hydrogen, nitro, cyano or SO 2 Ar but are not both hydrogen; R is hydrogen, lower alkyl or Het(CH 2 ) m Z(CH 2 ) n ; Z is sulphur; m is 0, 1 or 2 and n is 2 or 3, provided that the sum of m and n is 3 or 4; Het is a pyridine ring which ring is optionally substituted by lower alkyl, hydroxyl, halogen or amino; and Ar is an aryl group such as phenyl optionally substituted by halogen or methyl or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
22 words
A pharmaceutical composition of claim 1 wherein X and Y are hydrogen, nitro or cyano; and R is hydrogen or lower alkyl.
Claim 4
Dependent Claim
26 words
A pharmaceutical composition of claim 1 wherein R is methyl or Het CH 2 SCH 2 CH 2 ; m is 1 and n is 2.
Claim 5
Dependent Claim
20 words
A pharmaceutical composition of claim 1 wherein Het is pyridine and is optionally substituted by methyl, hydroxy, halogen or amino.
Claim 6
Dependent Claim
14 words
A pharmaceutical composition of claim 1 wherein X is nitro and Y is hydrogen.
Claim 7
Dependent Claim
13 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is 1-nitro-2-methylamino-2-[2-((3-chloro-2-pyridyl)methylthio)ethylamino]ethylene.
Claim 8
Dependent Claim
13 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is 1-nitro-2-methylamino-2-[2-((3-bromo-2-pyridyl)methylthio)ethylamino]ethylene.
Claim 9
Dependent Claim
13 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is 1-nitro-2,2-bis-[2-((3-bromo-2-pyridyl)methylthio)ethylamino]ethylene.
Claim 10
Dependent Claim
25 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is present in an amount of from about 50 mg to about 250 mg.
Claim 11
Independent Claim
137 words
A method of inhibiting H-2 histamine receptors which comprises administering to an animal in need thereof in an effective amount to inhibit said receptors a heterocyclic compound of the formula: ##STR9## wherein X and Y, which may be the same or different, are hydrogen, nitro, cyano or SO 2 Ar but are not both hydrogen; R is hydrogen, lower alkyl or Het(CH 2 ) m Z(CH 2 ) n ; Z is sulphur; m is 0, 1 or 2 and n is 2 or 3, provided that the sum of m and n is 3 or 4; Het is a pyridine ring which ring is optionally substituted by lower alkyl, hydroxyl, halogen or amino; and Ar is an aryl group such as phenyl optionally substituted by halogen or methyl or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Independent Claim
137 words
A method of inhibiting H-2 histamine receptors which comprises administering to an animal in need thereof in an effective amount to inhibit said receptors a heterocyclic compound of the formula: ##STR9## wherein X and Y, which may be the same or different, are hydrogen, nitro, cyano or SO 2 Ar but are not both hydrogen; R is hydrogen, lower alkyl or Het(CH 2 ) m Z(CH 2 ) n ; Z is sulphur; m is 0, 1 or 2 and n is 2 or 3, provided that the sum of m and n is 3 or 4; Het is a pyridine ring which ring is optionally substituted by lower alkyl, hydroxyl, halogen or amino; and Ar is an aryl group such as phenyl optionally substituted by halogen or methyl or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Dependent Claim
22 words
A method of claim 10 in which X and Y are hydrogen, nitro or cyano; and R is hydrogen or lower alkyl.
Claim 14
Dependent Claim
12 words
A method of claim 10 in which the heterocylic compound is 1-nitro-2-methylamino-2-[2-((3-chloro-2-pyridyl)-methylthio)ethylamino]ethylene.
Claim 15
Dependent Claim
12 words
A method of claim 10 in which the heterocylic compound is 1-nitro-2-methylamino-2-[2-((3-bromo-2-pyridyl)-methylthio)ethylamino]ethylene.
Claim 16
Dependent Claim
12 words
A method of claim 10 in which the heterocyclic compound is 1-nitro-2,2-bis-[2-((3-bromo-2-pyridyl)methylthio)-ethylamino]ethylene.
Claim 17
Dependent Claim
25 words
A method of claim 10 in which the heterocylic compound is administered in a daily dosage of from about 150 mg to about 750 mg.
Claim 18
Independent Claim
139 words
A method of inhibiting gastric acid secretion which comprises administering internally to an animal in need thereof in an effective amount to inhibit gastric acid secretion a heterocyclic compound of the formula: ##STR10## wherein X and Y, which may be the same or different, are hydrogen, nitro, cyano or SO 2 Ar but are not both hydrogen; R is hydrogen, lower alkyl or Het(CH 2 ) m Z(CH 2 ) n ; Z is sulphur; m is 0, 1 or 2 and n is 2 or 3, provided that the sum of m and n is 3 or 4; Het is a pyridine ring which ring is optionally substituted by lower alkyl, hydroxyl, halogen or amino; and Ar is an aryl group such as phenyl optionally substituted by halogen or methyl or a pharmaceutically acceptable acid addition salt thereof.
Claim 19
Independent Claim
139 words
A method of inhibiting gastric acid secretion which comprises administering internally to an animal in need thereof in an effective amount to inhibit gastric acid secretion a heterocyclic compound of the formula: ##STR10## wherein X and Y, which may be the same or different, are hydrogen, nitro, cyano or SO 2 Ar but are not both hydrogen; R is hydrogen, lower alkyl or Het(CH 2 ) m Z(CH 2 ) n ; Z is sulphur; m is 0, 1 or 2 and n is 2 or 3, provided that the sum of m and n is 3 or 4; Het is a pyridine ring which ring is optionally substituted by lower alkyl, hydroxyl, halogen or amino; and Ar is an aryl group such as phenyl optionally substituted by halogen or methyl 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) | 1980-05-16 | 1980-11-15 | 1981-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-16 | 1984-11-15 | 1985-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-16 | 1988-11-15 | 1989-05-17 | $7700.00 | Window Closed / Lapsed |