CA2016501A1 - Substituted pyrrole compounds and their applications in pharmacy - Google Patents

Substituted pyrrole compounds and their applications in pharmacy

Info

Publication number
CA2016501A1
CA2016501A1 CA002016501A CA2016501A CA2016501A1 CA 2016501 A1 CA2016501 A1 CA 2016501A1 CA 002016501 A CA002016501 A CA 002016501A CA 2016501 A CA2016501 A CA 2016501A CA 2016501 A1 CA2016501 A1 CA 2016501A1
Authority
CA
Canada
Prior art keywords
group
alkyl
denotes
compounds
substituted
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
CA002016501A
Other languages
French (fr)
Other versions
CA2016501C (en
Inventor
Ludwig Steindl
Matthias Lehr
Gerd Dannhardt
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.)
Merckle GmbH
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2016501A1 publication Critical patent/CA2016501A1/en
Application granted granted Critical
Publication of CA2016501C publication Critical patent/CA2016501C/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C07D207/323—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Abstract

The invention concerns substituted pyrrole compounds and their applications in pharmacy. The compounds of the invention are potent inhibitors of lipoxygenase and cyclo-oxygenase and therefore are suitable to treat the set of rheumatic illnesses and to prevent allergically induced ailments.
The compounds have the general formula:
CA002016501A 1989-05-11 1990-05-10 Substituted pyrrole compounds and their applications in pharmacy Expired - Lifetime CA2016501C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3915450A DE3915450A1 (en) 1989-05-11 1989-05-11 SUBSTITUTED PYRROL COMPOUNDS AND THEIR USE IN PHARMACY
DEP3915450.5 1989-05-11

Publications (2)

Publication Number Publication Date
CA2016501A1 true CA2016501A1 (en) 1990-11-11
CA2016501C CA2016501C (en) 2001-10-09

Family

ID=6380477

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002016501A Expired - Lifetime CA2016501C (en) 1989-05-11 1990-05-10 Substituted pyrrole compounds and their applications in pharmacy

Country Status (13)

Country Link
EP (1) EP0397175B1 (en)
JP (1) JP2796876B2 (en)
KR (1) KR0173455B1 (en)
AR (1) AR246256A1 (en)
AT (1) ATE98246T1 (en)
AU (1) AU637098B2 (en)
CA (1) CA2016501C (en)
DD (1) DD294260A5 (en)
DE (2) DE3915450A1 (en)
DK (1) DK0397175T3 (en)
ES (1) ES2062160T3 (en)
FI (1) FI95258C (en)
NO (1) NO174892C (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK0679157T3 (en) * 1993-01-15 1998-07-27 Searle & Co Novel 3,4-diarylthiophenes and analogs thereof for use as anti-inflammatory agents
US6492413B2 (en) 1993-01-15 2002-12-10 G.D. Searle & Co. 3.4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents
US5474995A (en) * 1993-06-24 1995-12-12 Merck Frosst Canada, Inc. Phenyl heterocycles as cox-2 inhibitors
DE4338770A1 (en) * 1993-11-12 1995-05-18 Matthias Dr Lehr Indole-2-alkanoic acids and their derivatives as inhibitors of phospholipase A¶2¶
DE4419247A1 (en) * 1994-06-01 1995-12-07 Merckle Gmbh New pyrrolizine keto-acid, keto-ester and carboxamide derivs.
DE4419246A1 (en) * 1994-06-01 1995-12-07 Merckle Gmbh New hetero-aryl substd. pyrrolizine derivs.
DE4419315A1 (en) * 1994-06-01 1995-12-07 Merckle Gmbh New hetero- and oxo-pyrrolizine derivs.
KR100482268B1 (en) * 1996-08-01 2005-04-14 메르클레 게엠베하 Acylpyrroldicarboxylic acids and acylindoldicarboxylic acids and their derivatives and inhibitors of the cytosolic phospholipase a2
EP1252164B1 (en) * 2000-01-28 2004-03-24 Merckle Gmbh Method for producing 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizine-5-yl acetic acid
DE10004157A1 (en) * 2000-02-01 2001-08-02 Merckle Gmbh Chem Pharm Fabrik New pyridyl- or pyrimidinyl-substituted bicyclic pyrrole derivatives, are cyclokine release inhibitors useful for treating immune system-related disorders, e.g. cancer, multiple sclerosis or arthritis
KR20020007836A (en) * 2000-07-19 2002-01-29 신덕호 Golf ball
DE10141285A1 (en) 2001-08-23 2003-03-27 Merckle Gmbh Process for the preparation of 6- (4-chlorophenyl) -2,2-dimethyl-7-phnyl-2,3-dihydro-1H-pyrrolizin-5-yl-acetic acid
DE102005012971A1 (en) 2005-03-21 2006-09-28 Merckle Gmbh Polymorphic form of 6- (4-chlorophenyl) -2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl-acetic acid

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1156473A (en) * 1965-04-30 1969-06-25 Firmenich & Cie Thiazole Alcohols
AU429651B2 (en) * 1968-08-08 1972-11-01 Commonwealth Scientific And Industrial Research Organization Antiviral 6, 7 dihydro 5h pyrrolizines and related compounds
DE2062984A1 (en) * 1970-12-21 1972-06-22 Messerschmitt, Thilo, 8094 Reitmehring; Dobeneck, Henning von, 8021 Icking 2-unsubstd-5-formyl-pyrrole prepn - by catalytic hydrogenation of 2-halo-5-formyl-pyrroles
DE2261965A1 (en) * 1971-12-23 1973-06-28 Continental Pharma DERIVATIVES OF PYRROE ACETIC ACID AND ITS SALTS AND OF PYRROL ACETONITRILE, PROCESS FOR THE PREPARATION OF THESE COMPOUNDS, PHARMACEUTICAL PRODUCTS CONTAINING THESE COMPOUNDS AND USES OF THESE COMPOUNDS AND PRODUCTS
JPS5217074B2 (en) * 1972-04-25 1977-05-13
JPS6011899B2 (en) * 1978-12-27 1985-03-28 財団法人相模中央化学研究所 Method for producing pyrrole acetic acid derivative
JPS5687558A (en) * 1979-11-27 1981-07-16 Mcneilab Inc Manufacture of pyrrolee22acetic acids
US4284562A (en) * 1979-11-27 1981-08-18 Mcneilab, Inc. Process for preparing pyrrole-2-acetic acids
JPS56100784A (en) * 1980-01-16 1981-08-12 Yoshitomi Pharmaceut Ind Ltd Indolizine derivative
US4327221A (en) * 1980-10-15 1982-04-27 American Home Products Corporation 2-Substituted-3-hydroxythiazolo(2,3-8)-thiazolium salts and mesoionic didehydro derivatives thereof
WO1982002044A1 (en) * 1980-12-15 1982-06-24 Corp Ethyl Preparation of pyrrole esters
EP0091181B1 (en) * 1982-02-25 1986-12-17 Beecham Group Plc Aroyl pyrrolizine compounds, process for their preparation and pharmaceutical compositions containing them
FR2539417A1 (en) * 1983-01-13 1984-07-20 Rhone Poulenc Sante NEW PYRROLO-1, 2 HETEROCYCLES, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM
FR2557111B1 (en) * 1983-12-21 1986-04-11 Rhone Poulenc Sante NOVEL ORTHO-CONDENSES OF PYRROLE, THEIR PREPARATION AND THE MEDICINAL PRODUCTS CONTAINING THEM
IL78834A (en) * 1985-05-23 1992-07-15 Smithkline Beckman Corp 2,3-dihydro-5-(1,4-dihydropyridin-4-yl)-6-phenylimidazo(2,1-b)thiazoles and 6,7-dihydro-3-(1,4-dihydropyridin-4-yl)-2-phenyl-5h-imidazo(2,1-b)(1,3)thiazines and their use as intermediates in a process for preparing the corresponding pyridyl-substituted imidazo(2,1-b)thiazoles and 5h-imidazo(2,1-b)(1,3)thiazines
FR2601016B1 (en) * 1986-07-04 1988-10-07 Rhone Poulenc Sante NOVEL 1H, 3H-PYRROLO (1,2-C) THIAZOLE DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR2617484B1 (en) * 1987-07-02 1989-10-20 Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF ACID (PYRIDYL-3) -3 1H-3H-PYRROLO (1,2-C) THIAZOLECARBOXYLIQUE-7 DEXTROGYRE

Also Published As

Publication number Publication date
DE3915450A1 (en) 1990-11-15
FI95258B (en) 1995-09-29
DD294260A5 (en) 1991-09-26
EP0397175A1 (en) 1990-11-14
FI95258C (en) 1996-01-10
NO902084L (en) 1990-11-12
EP0397175B1 (en) 1993-12-08
ES2062160T3 (en) 1994-12-16
DE59003753D1 (en) 1994-01-20
NO174892B (en) 1994-04-18
DK0397175T3 (en) 1994-02-14
FI902316A0 (en) 1990-05-09
KR0173455B1 (en) 1999-02-01
NO902084D0 (en) 1990-05-10
ATE98246T1 (en) 1993-12-15
NO174892C (en) 1994-07-27
JPH035455A (en) 1991-01-11
CA2016501C (en) 2001-10-09
JP2796876B2 (en) 1998-09-10
AR246256A1 (en) 1994-07-29
KR900018103A (en) 1990-12-20
AU5480090A (en) 1990-11-15
AU637098B2 (en) 1993-05-20

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Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed
MKEC Expiry (correction)

Effective date: 20121202