GB1390866A - Cycloalkanoyl-substituted pyrroles and pharmaceutical compo sitions containing them - Google Patents

Cycloalkanoyl-substituted pyrroles and pharmaceutical compo sitions containing them

Info

Publication number
GB1390866A
GB1390866A GB285473A GB285473A GB1390866A GB 1390866 A GB1390866 A GB 1390866A GB 285473 A GB285473 A GB 285473A GB 285473 A GB285473 A GB 285473A GB 1390866 A GB1390866 A GB 1390866A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
acetonitrile
methylpyrrole
expl
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
GB285473A
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.)
Janssen Pharmaceuticals Inc
Original Assignee
McNeilab Inc
McNeil Laboratories 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
Priority claimed from US00219864A external-priority patent/US3803171A/en
Priority claimed from US00219861A external-priority patent/US3803169A/en
Application filed by McNeilab Inc, McNeil Laboratories Inc filed Critical McNeilab Inc
Publication of GB1390866A publication Critical patent/GB1390866A/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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/337—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

Abstract

1390866 Cycloalkanoyl-substituted pyrroles McNEIL LABORATORIES Inc 19 Jan 1973 [21 Jan 1972 (2)] 2854/73 Heading C2C The invention comprises a 5-cycloalkanoylpyrrole of formula wherein R 4 is benzyl or n being an integer of 1 or 2; R is a hydrogen atom or a C 1-5 alkyl group; R 1 and R 2 are each a hydrogen atom or a methyl group; and R 3 is -COOH or a -COO (C 1-5 alkyl), provided that when said R 2 is a methyl group, the said R is a C 1-5 alkyl group. This compound may be prepared by (a) reacting a compound of formula R 4 COCI with a compound of formula wherein R<SP>1</SP> is a -COO (C 1-5 alkyl) group, in the presence of of a Lewis acid and a suitable solvent to obtain a compound of Formula IV or (b) subjecting a compound of Formula V, prepared according to method (a) to C-methylation according to standard techniques to yield a compound of formula or (c) (i) subjecting a compound of formula to conventional N-alkylation to prepare a compound of formula and optionally (ii) subjecting the compound prepared according to step (i) to conventional C-methylation to prepare a compound of formula and (iii) subjecting any of the aforementioned resultant compounds from steps (i) and (ii) to conventional hydrolysis to prepare a compound of formula or (d) esterifying a compound of formula with a lower alkanol by standard techniques to prepare a compound of formula in all the formulae referred to in steps (a) to (d), R, R 1 , R 2 , R 3 and R 4 are as defined above. The following intermediates are prepared in the examples: 5 - cylohexyl carbonyl - 1 -methylpyrrole - 2 - acetonitrile by the reaction of cyclohexylcarbonyl chloride with 1-methylpyrrole- 2-acetonitrile, Expl. (IA); 5-cyclopentylcarbonyl- 1 - methylpyrrole - 2 - acetonitrile Expl. (IB); 5 - cyclohexylcarbonyl - 1,α - dimethylpyrrole- 2-acetonitrile by the reaction of 5-cyclohexylcarbonyl - 1 - methylpyrrole - 2 - acetonitrile with CH 3 I, Expl. VI A: 5-cyclohexylcarbonyl- 1 - methylpyrrole - 2 - acetamide prepared by hydrolysing 5 - cyclohexylcarbonyl - 1 - methylpyrrole - 2 - acetonitrile, Expl. (VII); cyclohexanoyl-pyrrole-2-acetonitrile by the reaction of cyclohexanoyl chloride with pyrrole-2- acetonitrile, Expl. (IX); 5-cyclohexanoyl- 1 - ethylpyrrole - 2 - acetonitrile, Expl. (X); 1- methyl - 5 phenylacetylpyrrole - 2 - acetonitrile by the reaction of phenyl acetyl chloride with N- methylpyrrole - 2 -acetonitrile. The invention also comprises a pharmaceutical composition which contains as an active ingredient a compound according to the invention together with an inert diluent or carrier.
GB285473A 1972-01-21 1973-01-19 Cycloalkanoyl-substituted pyrroles and pharmaceutical compo sitions containing them Expired GB1390866A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US00219864A US3803171A (en) 1972-01-21 1972-01-21 5-phenylacetyl-pyrroles
US00219861A US3803169A (en) 1972-01-21 1972-01-21 Cycloalkanoyl-substituted pyrroles

Publications (1)

Publication Number Publication Date
GB1390866A true GB1390866A (en) 1975-04-16

Family

ID=26914338

Family Applications (1)

Application Number Title Priority Date Filing Date
GB285473A Expired GB1390866A (en) 1972-01-21 1973-01-19 Cycloalkanoyl-substituted pyrroles and pharmaceutical compo sitions containing them

Country Status (8)

Country Link
JP (1) JPS4880556A (en)
AT (1) AT326115B (en)
BE (1) BE794160A (en)
CA (1) CA996939A (en)
CH (1) CH587815A5 (en)
DE (1) DE2302671A1 (en)
FR (1) FR2183658B1 (en)
GB (1) GB1390866A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996010013A1 (en) * 1994-09-27 1996-04-04 Ono Pharmaceutical Co., Ltd. Five membered heterocyclic compounds
US5859042A (en) * 1995-09-27 1999-01-12 Ono Pharmaceutical Co., Ltd. Five membered heterocyclic compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2965915D1 (en) * 1979-08-13 1983-08-25 Mcneilab Inc Preparation of pyrrole-2-acetates

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996010013A1 (en) * 1994-09-27 1996-04-04 Ono Pharmaceutical Co., Ltd. Five membered heterocyclic compounds
US5859042A (en) * 1995-09-27 1999-01-12 Ono Pharmaceutical Co., Ltd. Five membered heterocyclic compounds

Also Published As

Publication number Publication date
DE2302671A1 (en) 1973-07-26
FR2183658A1 (en) 1973-12-21
AT326115B (en) 1975-11-25
BE794160A (en) 1973-07-17
FR2183658B1 (en) 1975-11-21
ATA47373A (en) 1975-02-15
JPS4880556A (en) 1973-10-29
CA996939A (en) 1976-09-14
CH587815A5 (en) 1977-05-13

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Legal Events

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