GB2023133A - Heterocyclic derivatives - Google Patents

Heterocyclic derivatives

Info

Publication number
GB2023133A
GB2023133A GB7913730A GB7913730A GB2023133A GB 2023133 A GB2023133 A GB 2023133A GB 7913730 A GB7913730 A GB 7913730A GB 7913730 A GB7913730 A GB 7913730A GB 2023133 A GB2023133 A GB 2023133A
Authority
GB
United Kingdom
Prior art keywords
alkyl
aralkyl
alkenyl
alkoxy
hydroxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
GB7913730A
Other versions
GB2023133B (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Glaxo Group Ltd
Original Assignee
Glaxo Group Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd
Priority to IE846/79A priority Critical patent/IE48750B1/en
Publication of GB2023133A publication Critical patent/GB2023133A/en
Application granted granted Critical
Publication of GB2023133B publication Critical patent/GB2023133B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms

Abstract

The invention relates to compounds of the general formula (I> <IMAGE> and physiologically acceptable salts, hydrates and bioprecursors thereof, in which R1 and R2, each represent hydrogen, C1-10 alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, trifluoroalkyl or alkyl substituted by hydroxy, alkoxy, amino, alkylamino, dialkylamino or cycloalkyl, or R1 and R2 may together with the nitrogen atom to which they are attached form a 5 to 10 membered alicyclic heterocyclic ring; Alk represents a straight or branched alkylene chain of 1 to 6 carbon atoms; Q represents a furan or thiophen ring in which incorporation into the rest of the molecule is through bonds at the 2- and 5-positions, or a benzene ring in which incorporation into the rest of the molecule is through bonds at the 1- and 3- or 1- and 4-positions; R7 represents halogen or C1-4 alkyl which may be substituted by hydroxy or C1-4 alkoxy; X represents -CH2-, -O- or -S- <IMAGE> where R6 represents hydrogen or methyl; n represents zero, 1 or 2; m represents 2, 3 or 4; R3 represents hydrogen, alkyl, alkenyl, aralkyl, hydroxyalkyl having at least two carbon atoms, alkoxyalkyl or aryl; and R4 and R5, each represent hydrogen, alkyl, alkyl substituted by hydroxy or C1-3 alkoxy, alkenyl, aralkyl or heteroaralkyl or R4 and R5 may together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain another heteroatom, or the group <IMAGE> or R4 and R5 taken together may represent the group =CR8R9 where R8 represents aryl or heteroaryl and R9 represents hydrogen or alkyl. The compounds show pharmacological activity as selective histamine H2-antagonists.
GB7913730A 1978-04-26 1979-04-19 Heterocyclic derivatives Expired GB2023133B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
IE846/79A IE48750B1 (en) 1978-04-26 1979-08-08 Heterocyclic derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1646878 1978-04-26

Publications (2)

Publication Number Publication Date
GB2023133A true GB2023133A (en) 1979-12-28
GB2023133B GB2023133B (en) 1982-09-08

Family

ID=10077887

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7913730A Expired GB2023133B (en) 1978-04-26 1979-04-19 Heterocyclic derivatives

Country Status (5)

Country Link
JP (1) JPS54160391A (en)
KR (1) KR840000420B1 (en)
BE (1) BE875846A (en)
GB (1) GB2023133B (en)
ZA (1) ZA792021B (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0067436A2 (en) * 1981-06-15 1982-12-22 Merck & Co. Inc. Diamino isothiazole -1-oxides and -1,1-dioxides as gastric secretion inhibitors
EP0070097A1 (en) * 1981-06-11 1983-01-19 Glaxo Group Limited 1,2,4-Triazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing them
EP0113782A1 (en) * 1982-07-21 1984-07-25 Rorer International (Overseas) Inc. Bicyclic nitrogen heterocyclic ethers and thioethers, and their pharmaceutical uses
EP0120585A1 (en) * 1983-02-22 1984-10-03 American Home Products Corporation Fused heterocyclic compounds
US4481199A (en) * 1980-08-27 1984-11-06 Glaxo Group Limited 1,2,4-Triazole-3-amine and 1,2,4 triazole-3,5-diamine compounds and their pharmaceutical use
US4539316A (en) * 1981-05-18 1985-09-03 Bristol-Myers Company Pyridine derivatives of 1,2-diaminocyclobutene-3,4-diones
US4546188A (en) * 1981-05-18 1985-10-08 Bristol-Myers Company Substituted 1,2-diaminocyclobutene-3,4-diones
US4670448A (en) * 1980-02-28 1987-06-02 Glaxo Group Limited Triazole amine compounds, their pharmaceutical compositions and method of use
US4772622A (en) * 1983-03-25 1988-09-20 Merck & Co., Inc. 3,5-diamino-1,2,4-oxidiazoles as gastric secretion inhibitors
US4927968A (en) * 1987-05-14 1990-05-22 Bristol-Myers Company Chemical intermediates and process

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA801151B (en) * 1979-03-02 1981-02-25 Glaxo Group Ltd Heterocyclic derivatives
US4338453A (en) 1980-09-17 1982-07-06 The Upjohn Company Aminoalkyl-1,2,4-triazoles
US4395553A (en) 1981-05-18 1983-07-26 Bristol-Myers Company Chemical compounds
US4390701A (en) 1981-05-18 1983-06-28 Bristol-Myers Company 1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione
US4495193A (en) * 1982-12-30 1985-01-22 Biomeasure, Inc. Imidazole compounds which reduce gastric acid secretion
US4565815A (en) * 1982-12-30 1986-01-21 Biomeasure, Inc. Pyrazolo[1,5-a]-1,3,5-triazines
US4567191A (en) * 1983-06-07 1986-01-28 Merck & Co., Inc. Amino-phenyl-thiadiazoledioxides as gastric secretion inhibitors
HU193253B (en) * 1985-01-29 1987-08-28 Egyt Gyogyszervegyeszeti Gyar Process for preparing 3,5-diamino-1,2,4-triazole derivatives

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4670448A (en) * 1980-02-28 1987-06-02 Glaxo Group Limited Triazole amine compounds, their pharmaceutical compositions and method of use
US4481199A (en) * 1980-08-27 1984-11-06 Glaxo Group Limited 1,2,4-Triazole-3-amine and 1,2,4 triazole-3,5-diamine compounds and their pharmaceutical use
US4539316A (en) * 1981-05-18 1985-09-03 Bristol-Myers Company Pyridine derivatives of 1,2-diaminocyclobutene-3,4-diones
US4546188A (en) * 1981-05-18 1985-10-08 Bristol-Myers Company Substituted 1,2-diaminocyclobutene-3,4-diones
EP0070097A1 (en) * 1981-06-11 1983-01-19 Glaxo Group Limited 1,2,4-Triazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing them
EP0067436A2 (en) * 1981-06-15 1982-12-22 Merck & Co. Inc. Diamino isothiazole -1-oxides and -1,1-dioxides as gastric secretion inhibitors
EP0067436A3 (en) * 1981-06-15 1983-01-19 Merck & Co. Inc. Diamino isothiazole -1-oxides and -1,1-dioxides as gastric secretion inhibitors
EP0113782A1 (en) * 1982-07-21 1984-07-25 Rorer International (Overseas) Inc. Bicyclic nitrogen heterocyclic ethers and thioethers, and their pharmaceutical uses
EP0113782A4 (en) * 1982-07-21 1986-03-18 Rorer Internat Overseas Inc Bicyclic nitrogen heterocyclic ethers and thioethers, and their pharmaceutical uses.
EP0120585A1 (en) * 1983-02-22 1984-10-03 American Home Products Corporation Fused heterocyclic compounds
US4772622A (en) * 1983-03-25 1988-09-20 Merck & Co., Inc. 3,5-diamino-1,2,4-oxidiazoles as gastric secretion inhibitors
US4927968A (en) * 1987-05-14 1990-05-22 Bristol-Myers Company Chemical intermediates and process

Also Published As

Publication number Publication date
KR840000420B1 (en) 1984-04-02
JPH0351708B2 (en) 1991-08-07
JPS54160391A (en) 1979-12-19
KR830000694A (en) 1983-04-18
GB2023133B (en) 1982-09-08
BE875846A (en) 1979-10-25
ZA792021B (en) 1980-06-25

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee