GB1384022A - Hexamethylene-imine derivatives and their preparation - Google Patents

Hexamethylene-imine derivatives and their preparation

Info

Publication number
GB1384022A
GB1384022A GB1316173A GB1316173A GB1384022A GB 1384022 A GB1384022 A GB 1384022A GB 1316173 A GB1316173 A GB 1316173A GB 1316173 A GB1316173 A GB 1316173A GB 1384022 A GB1384022 A GB 1384022A
Authority
GB
United Kingdom
Prior art keywords
general formula
condensing
acid
group
pharmaceutically acceptable
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.)
Expired
Application number
GB1316173A
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.)
Laboratoires Innothera SAS
Original Assignee
Laboratoires Innothera SAS
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 Laboratoires Innothera SAS filed Critical Laboratoires Innothera SAS
Publication of GB1384022A publication Critical patent/GB1384022A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C07D307/54—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
    • 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
    • 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
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/60—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)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

1384022 Hexamethyleneimines INNOTHERA 19 March 1973 [30 March 1972] 13161/73 Heading C2C Novel hexamethyleneimines of the general formula wherein R is a hydrogen atom or methyl or ethyl group, n is 0, 1, 2 or 3 and A is or R 1 R 2 CHCONH-, in which each of R 1 and R 2 is a straight or branched chain saturated C 1-6 aliphatic, allyl, cyclopentyl, cyclohexyl, cyclohexenyl, benzyl, halobenzyl, phenyl, halophenyl, methylphenyl, ethylphenyl, heterocyclyl or heterocyclylmethyl group, provided that when A is R 1 R 2 CHCOO- and one of R 1 and R 2 is a 3-thienyl group, the other is not a cyclopentyl, cyclohexyl, phenyl, halophenyl, methylphenyl or ethylphenyl group, including racemates and optical isomers, and quaternary ammonium pharmaceutically acceptable acid addition salts and derivatives thereof are prepared by condensing an acid of the general formula R 1 R 2 CHCOOH or a reactive functional derivative thereof with a hexamethyleneimine of the general formula wherein B is a halogen atom or hydroxyl or amino group. Acids of the second general formula above are prepared (a) by condensing mandelic acid, which may be substituted, with an appropriate benzene derivative in the presence of stannic chloride, (b) by condensing (by a malonic synthesis), optionally substituted ethyl phenylmalonate with benzyl chloride, which may be substituted, 2-chloromethylfuran or 2- or 3- chloromethyl-thiophene, followed by saponification and decarboxylation of the resulting malonic acid ester and (c) by reducing a glycollic acid of the general formula R 1 R 2 C(OH)COOH, obtained by condensing an appropriate glyoxylic acid with a Grignard reagent. Pharmaceutical compositions having spasmolytic and vasodilating activity comprise, as active ingredient, a hexamethyleneimine of the first general formula above or a pharmaceutically acceptable acid addition salt or quartenary ammonium derivative thereof, in association with a pharmaceutically acceptable carrier.
GB1316173A 1972-03-20 1973-03-19 Hexamethylene-imine derivatives and their preparation Expired GB1384022A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7209639A FR2176473B1 (en) 1972-03-20 1972-03-20

Publications (1)

Publication Number Publication Date
GB1384022A true GB1384022A (en) 1974-02-12

Family

ID=9095472

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1316173A Expired GB1384022A (en) 1972-03-20 1973-03-19 Hexamethylene-imine derivatives and their preparation

Country Status (5)

Country Link
JP (1) JPS5320039B2 (en)
CA (1) CA1010862A (en)
DE (1) DE2313338C3 (en)
FR (1) FR2176473B1 (en)
GB (1) GB1384022A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4377592A (en) 1979-10-23 1983-03-22 Innothera Antiarrhythmic activity of cetiedil
EP1426360A1 (en) * 2001-09-12 2004-06-09 Kaken Pharmaceutical Co., Ltd. 2-phenyl-3-heteroarylpropionic acid derivative or salt thereof and medicine containing the same

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5151164A (en) * 1974-10-30 1976-05-06 Nippon Kentetsu Co Ltd JIDOSENTAKUKI
FR2333501A2 (en) 1975-12-03 1977-07-01 Science Union & Cie NEW ACETAMIDES SUBSTITUTED THEIR METHODS OF OBTAINING AND THE PHARMACEUTICAL COMPOSITIONS BY CONTAINING
JPS52113572A (en) * 1976-03-19 1977-09-22 Sanyo Electric Co Ltd Controlling device for washing machine
FR2666509B1 (en) * 1990-09-12 1994-11-25 Adir USE OF N- (1-HEXAHYDROAZEPINYLALKYL) ACETAMIDES IN THE PREPARATION OF MEDICINES FOR THE TREATMENT OF CHOLINERGIC TRANSMISSION DISORDERS.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4377592A (en) 1979-10-23 1983-03-22 Innothera Antiarrhythmic activity of cetiedil
EP1426360A1 (en) * 2001-09-12 2004-06-09 Kaken Pharmaceutical Co., Ltd. 2-phenyl-3-heteroarylpropionic acid derivative or salt thereof and medicine containing the same
EP1426360A4 (en) * 2001-09-12 2006-04-12 Kaken Pharma Co Ltd 2-phenyl-3-heteroarylpropionic acid derivative or salt thereof and medicine containing the same

Also Published As

Publication number Publication date
DE2313338C3 (en) 1981-04-09
JPS495985A (en) 1974-01-19
DE2313338B2 (en) 1980-06-26
FR2176473A1 (en) 1973-11-02
CA1010862A (en) 1977-05-24
DE2313338A1 (en) 1973-10-04
JPS5320039B2 (en) 1978-06-24
FR2176473B1 (en) 1975-03-14

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Legal Events

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PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee