GB1267600A - 3-aroyl-pyrrolidines - Google Patents

3-aroyl-pyrrolidines

Info

Publication number
GB1267600A
GB1267600A GB30872/69A GB3087269A GB1267600A GB 1267600 A GB1267600 A GB 1267600A GB 30872/69 A GB30872/69 A GB 30872/69A GB 3087269 A GB3087269 A GB 3087269A GB 1267600 A GB1267600 A GB 1267600A
Authority
GB
United Kingdom
Prior art keywords
aroylpyrrolidine
reacting
aroyl
carbethoxy
denotes
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
GB30872/69A
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.)
AH Robins Co Inc
Original Assignee
AH Robins Co Inc
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 AH Robins Co Inc filed Critical AH Robins Co Inc
Publication of GB1267600A publication Critical patent/GB1267600A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms

Landscapes

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

Abstract

1,267,600. 3 - Aroyl - pyrrolidines. A. H. ROBINS CO. Inc. 18 June, 1969 [20 June, 1968], No. 30872/69. Heading C2C. Novel compounds of the formula where R denotes H, aryl, aryloxy, ethoxy, aroyl, C 3-9 cycloalkyl, carbethoxy or #-alkoxyalkyl, R<SP>1</SP> denotes H, F, Cl, Br, C 1-8 alkoxy, CF 3 or C 1-8 alkyl, Y denotes -CH 2 -, n is 0, 1, 2 or 3, and acid addition salts thereof, may be obtained (1) by reacting a 1-R<SP>11</SP>-3-cyanopyrrolidine with an arylmagnesium halide to give a 1-R<SP>11</SP>-3- aroylpyrrolidine (where R<SP>11</SP> is C 1-8 alkyl, C 3-9 cycloalkyl aryl or phenyl-C 1-8 alkyl; (2) by reacting a 1-benzoyl-3-aroylpyrrolidine with CNBr to form a 1-cyano-3-aroyl pyrrolidine and reacting the latter with cone. HCl to form a 3-aroylpyrrolidine and optionally substituting the latter at the 1-position by reaction with a compound X-Y n -R (where X is halogen); (3) by reacting an #-dialkylamino propiophenone with aziridine to form an #-aziridinylpropiophenone treating with ethyl chlorocarbonate to form an #-[N-carbethoxy-N-(2-chloroethyl)- amino] propiophenone reacting the latter with NaNH 2 to form a 1-carbethoxy-3-aroylpyrrolidine and optionally hydrolysing this under acid conditions to a 3-aroylpyrrolidine. Pharmaceutical compositions, useful as hypocholesterolemic agents, comprise compounds of the above formula, or their non-toxic acid addition salts, together with a pharmaceutically acceptable carrier, in the form of liquids, tablets or capsules.
GB30872/69A 1968-06-20 1969-06-18 3-aroyl-pyrrolidines Expired GB1267600A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US73841468A 1968-06-20 1968-06-20

Publications (1)

Publication Number Publication Date
GB1267600A true GB1267600A (en) 1972-03-22

Family

ID=24967910

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30872/69A Expired GB1267600A (en) 1968-06-20 1969-06-18 3-aroyl-pyrrolidines

Country Status (6)

Country Link
US (1) US3489769A (en)
JP (1) JPS4830635B1 (en)
CA (1) CA974528A (en)
DE (1) DE1931027A1 (en)
FR (1) FR2011338B1 (en)
GB (1) GB1267600A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE792042A (en) * 1971-11-30 1973-05-29 Ciba Geigy PROCESS FOR THE PREPARATION OF NEW ALCENYLENE-AMINES SUBSTITUTED IN 3
US4551540A (en) * 1983-01-17 1985-11-05 Borg-Warner Chemicals, Inc. Substituted 2,5-dimethylpyrroles
US4551539A (en) * 1983-01-17 1985-11-05 Borg-Warner Chemicals, Inc. Substituted 2,5-dimethylpyrroles
US5198449A (en) * 1990-04-27 1993-03-30 A. H. Robins Company Incorporated N-substituted alpha-arylazacycloalkylmethanamines and their use as cardiovascular agents
JP2023523300A (en) 2020-04-30 2023-06-02 イドーシア ファーマシューティカルズ リミテッド Azetidin-3-ylmethanol Derivatives as CCR6 Receptor Modulators
WO2023057548A1 (en) 2021-10-07 2023-04-13 Idorsia Pharmaceuticals Ltd Ccr6 receptor modulators
TW202325278A (en) 2021-10-26 2023-07-01 瑞士商愛杜西亞製藥有限公司 Ccr6 receptor modulators
AR127486A1 (en) 2021-10-28 2024-01-31 Idorsia Pharmaceuticals Ltd CCR6 RECEIVER MODULATORS

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3318908A (en) * 1962-06-18 1967-05-09 Robins Co Inc A H 3-cyanopyrrolidines
BE715405A (en) * 1966-10-06 1968-11-18

Also Published As

Publication number Publication date
FR2011338B1 (en) 1973-01-12
JPS4830635B1 (en) 1973-09-21
US3489769A (en) 1970-01-13
FR2011338A1 (en) 1970-02-27
DE1931027A1 (en) 1970-03-12
CA974528A (en) 1975-09-16

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