FR2215210A1 - Thioamides - as gastric acid secretion inhibitors - Google Patents

Thioamides - as gastric acid secretion inhibitors

Info

Publication number
FR2215210A1
FR2215210A1 FR7301428A FR7301428A FR2215210A1 FR 2215210 A1 FR2215210 A1 FR 2215210A1 FR 7301428 A FR7301428 A FR 7301428A FR 7301428 A FR7301428 A FR 7301428A FR 2215210 A1 FR2215210 A1 FR 2215210A1
Authority
FR
France
Prior art keywords
alkyl
morpholino
pyrrolidino
piperidino
methyl
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
FR7301428A
Other languages
French (fr)
Other versions
FR2215210B1 (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.)
Smith Kline and French Laboratories Ltd
GlaxoSmithKline LLC
Original Assignee
Smith Kline and French Laboratories Ltd
GlaxoSmithKline LLC
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 Smith Kline and French Laboratories Ltd, GlaxoSmithKline LLC filed Critical Smith Kline and French Laboratories Ltd
Priority to FR7301428A priority Critical patent/FR2215210A1/en
Publication of FR2215210A1 publication Critical patent/FR2215210A1/en
Application granted granted Critical
Publication of FR2215210B1 publication Critical patent/FR2215210B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/59—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with at least one of the bonds being to sulfur

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Cpds. (I): (where R1 is 2-pyridyl, 2- or 4-pyrimidyl, 2-pyrazinyl, 2-pyrrolyl, 2-quinolyl, or 2- or 4-thiazolyl; and (a) R2 is H, alkyl, alkenyl, Ph or PhCH2 and R3 is dialkylamino-, N-alkyl-N-phenyl-amino, pyrrolidino-piperidino-, morpholino- or N-alkyl-piperazino, methylamino; (b) R2 is H, alkyl, alkenyl or Ph opt. substd. by halogen. Alkyl or alkoxy and R3 is (3-6C)-cycloalkylamino or (3-6C)-cycloalkylmethylamino; (c) R2 is (CH2)m NR4R5, m = 0 or 1, and R4 and R5 are alkyl or NR4R5 is piperidino, pyrrolidino, or N-alkylpiperazino and R3 is NH-(CH2)n (3-6C)-cycloalkyl or NR6R7; R6 and R7 are H or alkyl; n is 0 or 1, (d) R2 is (CH2)mOR8, m is 0, 1 or 2, R8 is alkyl, allyl or cyclopropanemethyl and R3 is PhNH, NH(CH2)n (3-6C)-cycloalkyl or NR9R10 and R9 and R10 is H or alkyl, and n is 0 or 1; (e) R2 is H, alkyl, alkenyl, alkoxy, allyloxy, cyclopropanemethoxy, Ph, PhCH2 or (CH2)n NR11R12; n is 0 or 1 and R11 and R12 are alkyl or NR11R12 is piperidino, pyrrolidino, morpholino or N-alkyl-(2 of 2) piperazino and R3 is NHR13. R 13 is allyl or propargyl opt. substd. by Me or Et. The whole residue contg. 3-6C; (f) is morpholino-methyl and R3 is NH-(CH2)n-(3-6C)-cycloalkyl or NR14R15; R14 and R15 are H or alkyl; n is 0 or 1; (g) R2 is (CH2)mR16; m is 0 or 1 and R16 is dialkylamino, N-alkyl-N-phenylamino, piperidino; pyrrolidino, morpholino or N-alkylpiperazino and R3 is NHCH2R16) are prepd. by modification of R1R2CSNH2 reaction of R1R2CH2 with an isothiocyanate or ClCSN (alkyl)2 in the presence of LiBu of LiPh or reaction of R1CHO with an amine and an alkali metal cyanide to give an amino-nitrile then reaction with H2S or an ammonium polysulphide or P2S5. Thus 3-methyl-N-morpholino-methyl-2-(2-pyridyl) thiobutanamide is prepd. from morpholine. HCHO and 3-methyl-2-(2-pyridyl)thiobutanamide.
FR7301428A 1973-01-16 1973-01-16 Thioamides - as gastric acid secretion inhibitors Granted FR2215210A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7301428A FR2215210A1 (en) 1973-01-16 1973-01-16 Thioamides - as gastric acid secretion inhibitors

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7301428A FR2215210A1 (en) 1973-01-16 1973-01-16 Thioamides - as gastric acid secretion inhibitors

Publications (2)

Publication Number Publication Date
FR2215210A1 true FR2215210A1 (en) 1974-08-23
FR2215210B1 FR2215210B1 (en) 1976-10-08

Family

ID=9113370

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7301428A Granted FR2215210A1 (en) 1973-01-16 1973-01-16 Thioamides - as gastric acid secretion inhibitors

Country Status (1)

Country Link
FR (1) FR2215210A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0223512A2 (en) * 1985-11-08 1987-05-27 Suntory Limited 2-Pyridylacetic acid derivative, preparation process thereof and pharmaceutical composition containing the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0223512A2 (en) * 1985-11-08 1987-05-27 Suntory Limited 2-Pyridylacetic acid derivative, preparation process thereof and pharmaceutical composition containing the same
EP0223512A3 (en) * 1985-11-08 1988-08-31 Suntory Limited 2-pyridylacetic acid derivative, preparation process thereof and pharmaceutical composition containing the same
US4843083A (en) * 1985-11-08 1989-06-27 Suntory Limited 2-pyridylacetic acid derivative, and pharmaceutical composition containing the same and method of treating a peptic ulcer

Also Published As

Publication number Publication date
FR2215210B1 (en) 1976-10-08

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Legal Events

Date Code Title Description
ST Notification of lapse