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US4692531A Expired / Lapsed US ⏱️ 0.0 years remaining

Substituted 3,4-diamino-1,2,5-thiadiazoles having histamine H2 -receptor antagonist activity

Assignee: Bristol Myers Co
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Filing: 1986-09-25
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Granted: 1987-09-08
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Expires: 2006-09-25
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Abstract

Abstract Histamine H 2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R 1 are as defined herein, and their nontoxic pharmaceutically acceptable salts are novel anti-ulcer agents which are prepared by ring closure of a substituted ethanediimidamide of the formula ##STR2##

Inventors

  • 👤 Aldo A. Algieri
  • 👤 Ronnie R. Crenshaw

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 14:57
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/10; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/38; C07D277/44; C07D277/48; C07D417/00; C07D417/02; C07D417/12

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 229 words
A compound of the formula ##STR35## wherein R 1 is hydrogen, (lower)alkyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, allyl, propargyl, ##STR36## in which q is 1 or 2, R 2 and R 3 each are independently hydrogen, (lower)alkyl, (lower)alkoxy or halogen, and, when R 2 is hydrogen, R 3 also may be trifluoromethyl, or R 2 or R 3 , taken together, may be methlenedioxy, and R 4 is hydrogen, (lower)alkyl or (lower)alkoxy: m is an integer of from 0 to 2 inclusive; n is an integer of from 2 to 5 inclusive; Z is oxygen, sulfur or methylene; and A is a imidazole, thiazole, thiadiazole, oxazole, oxadiazole or pyrimidine; provided that A may contain one or two substituents, the first substituent being selected from ##STR37## or --CH 2 NR 6 R 7 and the second substituent selected from (lower)alkyl, halogen or (lower)alkoxy; R 5 is hydrogen, branched or unbranched (lower)alkyl, (lower)cycloalkyl, or (lower)cycloalkyl(lower)alkyl, in which R 5 may optionally contain one or more halogen atoms selected from fluorine, chlorine and bromine, provided that there is no halogen substituent on the carbon atom directly attached to the nitrogen atom; R 6 and R 7 each are independently hydrogen or (lower)alkyl, or, R 6 and R 7 , taken together with the nitrogen to which they are attached, may be pyrrolidino, methylpyrrolidino, piperidino, methylpiperidino, homopiperidino or heptamethyleneimino, and a nontoxic pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim 229 words
A compound of the formula ##STR35## wherein R 1 is hydrogen, (lower)alkyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, allyl, propargyl, ##STR36## in which q is 1 or 2, R 2 and R 3 each are independently hydrogen, (lower)alkyl, (lower)alkoxy or halogen, and, when R 2 is hydrogen, R 3 also may be trifluoromethyl, or R 2 or R 3 , taken together, may be methlenedioxy, and R 4 is hydrogen, (lower)alkyl or (lower)alkoxy: m is an integer of from 0 to 2 inclusive; n is an integer of from 2 to 5 inclusive; Z is oxygen, sulfur or methylene; and A is a imidazole, thiazole, thiadiazole, oxazole, oxadiazole or pyrimidine; provided that A may contain one or two substituents, the first substituent being selected from ##STR37## or --CH 2 NR 6 R 7 and the second substituent selected from (lower)alkyl, halogen or (lower)alkoxy; R 5 is hydrogen, branched or unbranched (lower)alkyl, (lower)cycloalkyl, or (lower)cycloalkyl(lower)alkyl, in which R 5 may optionally contain one or more halogen atoms selected from fluorine, chlorine and bromine, provided that there is no halogen substituent on the carbon atom directly attached to the nitrogen atom; R 6 and R 7 each are independently hydrogen or (lower)alkyl, or, R 6 and R 7 , taken together with the nitrogen to which they are attached, may be pyrrolidino, methylpyrrolidino, piperidino, methylpiperidino, homopiperidino or heptamethyleneimino, and a nontoxic pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim 94 words
A compound of claim 1 having the formula ##STR38## wherein R 1 is hydrogen, (lower)alkyl, allyl or propargyl, m is 0 or 1, n is 2 or 3, Z is oxygen, sulfur or methylene and A is imidazole, thiazole, thiadiazole, oxazole, oxadiazole or pyrimidine; provided that A is substituted by ##STR39## in which R 5 is hydrogen, or branched or unbranched (lower)alkyl group optionally substituted by one or more halogen atoms, provided that there is no halogen atom on the carbon atom attached to the nitrogen atom; or a nontoxic pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim 88 words
A compound of claim 1 having the formula ##STR40## wherein R 1 is hydrogen or (lower)alkyl, m is 0 or 1, n is 2 or 3, Z is oxygen, sulfur or methylene and A is thiazole or pyrimidine; provided that A is substituted by ##STR41## in which R 5 is hydrogen, or branched or unbranched (lower)alkyl group optionally substituted by one or more halogen atoms, provided that there is no halogen atom on the carbon atom attached to the nitrogen atom; or a nontoxic pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim 58 words
A compound of claim 1 having the formula ##STR42## wherein R 1 is hydrogen or (lower)alkyl, and R 5 is hydrogen, or branched on unbranched (lower)alkyl group optionally substituted by one or more halogen atoms, provided that there is no halogen atom on the carbon atom attached to the nitrogen atom; or a nontoxic pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim 8 words
N-{2-[(2-Guanidinothiazol-4-yl)methylthio]ethyl{ethanediimidamide, or a nontoxic pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim 8 words
N-{2-[(2-Guanidinothiazol-4-yl)methylthio]ethyl{ethanediimidamide, or a nontoxic pharmaceutically acceptable salt thereof.

References Cited (Backward Citations)

US4374248A Cited
EP0040696A2 Cited
EP0045155A1 Cited
EP0060730A2 Cited
EP0065823A1 Cited
US4440933A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-09-07 1991-03-09 1991-09-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-09-07 1995-03-09 1995-09-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-09-07 1999-03-09 1999-09-08 $7700.00 Window Closed / Lapsed

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