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FR2273532A1 - Alpha-aminoalkyl 2-thienylacetonitrile derivs - spasmolytics and vasodilators more active than papaverine - Google Patents

Alpha-aminoalkyl 2-thienylacetonitrile derivs - spasmolytics and vasodilators more active than papaverine

Info

Publication number
FR2273532A1
FR2273532A1 FR7419476A FR7419476A FR2273532A1 FR 2273532 A1 FR2273532 A1 FR 2273532A1 FR 7419476 A FR7419476 A FR 7419476A FR 7419476 A FR7419476 A FR 7419476A FR 2273532 A1 FR2273532 A1 FR 2273532A1
Authority
FR
France
Prior art keywords
alkyl
opt
esp
halo
thienylacetonitrile
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
FR7419476A
Other languages
French (fr)
Other versions
FR2273532B1 (en
Inventor
Henri Pierre Victor Tron
Don Pierre Rene Luc Giudicelli
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.)
Synthelabo SA
Original Assignee
Synthelabo SA
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 Synthelabo SA filed Critical Synthelabo SA
Priority to FR7419476A priority Critical patent/FR2273532A1/en
Priority to BE157061A priority patent/BE829913A/en
Priority to ES438290A priority patent/ES438290A1/en
Priority to DE19752525319 priority patent/DE2525319A1/en
Priority to JP6902275A priority patent/JPS51125070A/en
Publication of FR2273532A1 publication Critical patent/FR2273532A1/en
Application granted granted Critical
Publication of FR2273532B1 publication Critical patent/FR2273532B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Thiophene derivs. of formula (I) in racemic or optically active forms and their pharmaceutically acceptable acid addition salts are new: (R1= H or benzoyl opt. substd. by 1-3 halo esp. F; R2 = H or 1-6C alkyl, alkenyl or alkynyl, opt. substd. by halo, esp. Cl, COOH, alkoxycarbonyl (1-3C alkyl) or amino) the amino substits. being esp. N-bound 5-6 membered N-hetero-cycles, or R2 is benzyl or alpha-hydroxybenzyl; R3 and R4 are 1-6C alkyl, phenyl (1-3C) alkyl or NR3R4 is a 5-7 membered heterocycle opt. contg. further O, S or N atoms and 1-3 CH3 or C2H5 substits.; n = 2-3; cpds. where R1=H; R2 = sec. butyl; NR3R4 = pyrrolidino, piperidino or morpholino are excluded). They are prepd. eg. by reacting 2-thienylacetonitrile with XCnH2nNR3R4 (X = halo) then opt. replacement of R2 = H. (I) are useful in human and veterinary medicine as spasmolytics and vasolidators. The LD50 (mouse) is: p.o. 160-600 mg/kg; i.p. 75-300 mg/kg; i.v. 23-25 mg/kg; and in vitro spasmolytic activity (isolated guinea pig ileum) is 1.7-5 times that of papaverine hydrochloride. Usual oral dose is 10 mg-1 g/day.
FR7419476A 1974-06-06 1974-06-06 Alpha-aminoalkyl 2-thienylacetonitrile derivs - spasmolytics and vasodilators more active than papaverine Granted FR2273532A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
FR7419476A FR2273532A1 (en) 1974-06-06 1974-06-06 Alpha-aminoalkyl 2-thienylacetonitrile derivs - spasmolytics and vasodilators more active than papaverine
BE157061A BE829913A (en) 1974-06-06 1975-06-05 NEW DERIVATIVES OF THIENYL-2-ACETONITRILE
ES438290A ES438290A1 (en) 1974-06-06 1975-06-06 Production of 22 thienylacetonitrile derivatives
DE19752525319 DE2525319A1 (en) 1974-06-06 1975-06-06 Alpha-aminoalkyl 2-thienylacetonitrile derivs - spasmolytics and vasodilators more active than papaverine
JP6902275A JPS51125070A (en) 1974-06-06 1975-06-06 Production of 22 thienylacetonitrile derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7419476A FR2273532A1 (en) 1974-06-06 1974-06-06 Alpha-aminoalkyl 2-thienylacetonitrile derivs - spasmolytics and vasodilators more active than papaverine

Publications (2)

Publication Number Publication Date
FR2273532A1 true FR2273532A1 (en) 1976-01-02
FR2273532B1 FR2273532B1 (en) 1978-06-30

Family

ID=9139682

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7419476A Granted FR2273532A1 (en) 1974-06-06 1974-06-06 Alpha-aminoalkyl 2-thienylacetonitrile derivs - spasmolytics and vasodilators more active than papaverine

Country Status (2)

Country Link
BE (1) BE829913A (en)
FR (1) FR2273532A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4783537A (en) * 1985-11-13 1988-11-08 Pennwalt Corporation α-(aminoalkyl)-arylacetic acid derivatives
US4847301A (en) * 1985-11-13 1989-07-11 Pennwalt Corporation Methods of use of α-(aminoalkyl)-arylacetic acid derivatives
EP0330940A2 (en) * 1988-02-27 1989-09-06 Roche Diagnostics GmbH Trisubstituted amines, process for their preparation and pharmaceutical preparations containing these compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4783537A (en) * 1985-11-13 1988-11-08 Pennwalt Corporation α-(aminoalkyl)-arylacetic acid derivatives
US4847301A (en) * 1985-11-13 1989-07-11 Pennwalt Corporation Methods of use of α-(aminoalkyl)-arylacetic acid derivatives
EP0330940A2 (en) * 1988-02-27 1989-09-06 Roche Diagnostics GmbH Trisubstituted amines, process for their preparation and pharmaceutical preparations containing these compounds
EP0330940A3 (en) * 1988-02-27 1990-10-31 Roche Diagnostics GmbH Trisubstituted amines, process for their preparation and pharmaceutical preparations containing these compounds

Also Published As

Publication number Publication date
BE829913A (en) 1975-12-05
FR2273532B1 (en) 1978-06-30

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