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GB1554076A - 5-(2-furoyl)-5-(2-thenoyl)-5-(3-furoyl)-and 5-(3-thenoyl)-1,2-dihydro-3h-pyrrolo(1,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof - Google Patents

5-(2-furoyl)-5-(2-thenoyl)-5-(3-furoyl)-and 5-(3-thenoyl)-1,2-dihydro-3h-pyrrolo(1,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof

Info

Publication number
GB1554076A
GB1554076A GB28923/77A GB2892377A GB1554076A GB 1554076 A GB1554076 A GB 1554076A GB 28923/77 A GB28923/77 A GB 28923/77A GB 2892377 A GB2892377 A GB 2892377A GB 1554076 A GB1554076 A GB 1554076A
Authority
GB
United Kingdom
Prior art keywords
thenoyl
furoyl
carboxylic acid
pyrrolo
pyrrole
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
GB28923/77A
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.)
Syntex USA LLC
Original Assignee
Syntex USA LLC
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 US05/771,283 external-priority patent/US4087539A/en
Application filed by Syntex USA LLC filed Critical Syntex USA LLC
Publication of GB1554076A publication Critical patent/GB1554076A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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]
    • 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
    • C07D207/34—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—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)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Carboxylic acid esters of the formula <IMAGE> are prepared by condensation of a compound of the formula <IMAGE> with an amide of the formula <IMAGE> In the formulae, X represents oxygen or sulphur, R represents hydrogen or C1-C4-alkyl, R<1> represents hydrogen, methyl, chlorine or bromine and R<2> represents C1-C4-alkyl. Hydrolysis of the carboxylic acid esters results in the corresponding carboxylic acids and their salts. The compounds are novel and exhibit an anti inflammatory, analgesic and antipyretic action. They are suitable in particular for treating inflammations, pain and febrile conditions.
GB28923/77A 1976-07-14 1977-07-11 5-(2-furoyl)-5-(2-thenoyl)-5-(3-furoyl)-and 5-(3-thenoyl)-1,2-dihydro-3h-pyrrolo(1,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof Expired GB1554076A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70485776A 1976-07-14 1976-07-14
US05/771,283 US4087539A (en) 1976-07-14 1977-02-23 5-(2-Furoyl)-, 5-(2-thenoyl)-, 5-(3-furoyl)- and 5-(3-thenoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof

Publications (1)

Publication Number Publication Date
GB1554076A true GB1554076A (en) 1979-10-17

Family

ID=27107392

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28923/77A Expired GB1554076A (en) 1976-07-14 1977-07-11 5-(2-furoyl)-5-(2-thenoyl)-5-(3-furoyl)-and 5-(3-thenoyl)-1,2-dihydro-3h-pyrrolo(1,2-a)pyrrole-1-carboxylic acid derivatives and process for the production thereof

Country Status (26)

Country Link
JP (1) JPS539789A (en)
AR (1) AR218631A1 (en)
AU (1) AU513385B2 (en)
CA (1) CA1100140A (en)
CH (2) CH651045A5 (en)
CS (1) CS208724B2 (en)
DE (1) DE2731662A1 (en)
DK (1) DK152652C (en)
ES (2) ES460705A1 (en)
FI (1) FI63407C (en)
FR (1) FR2361396A1 (en)
GB (1) GB1554076A (en)
GR (1) GR61607B (en)
HK (1) HK17581A (en)
IE (1) IE45302B1 (en)
IL (1) IL52492A (en)
IT (1) IT1117314B (en)
MY (1) MY8100371A (en)
NL (1) NL7707652A (en)
NO (1) NO147563C (en)
NZ (1) NZ184611A (en)
PL (1) PL111408B1 (en)
PT (1) PT66779B (en)
SE (1) SE434644B (en)
SU (2) SU664566A3 (en)
YU (2) YU43156B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4097579A (en) * 1977-03-31 1978-06-27 Syntex (U.S.A.) Inc. 5-(2-Pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid derivatives and process for the production thereof
US4140698A (en) * 1977-07-25 1979-02-20 Syntex (Usa) Inc. 1,2-Dihydro-3H-pyrrolo[1,2-a]pyrrole-1-nitriles
US4353829A (en) * 1980-11-21 1982-10-12 Syntex (U.S.A.) Inc. Process for 5-aroylation of 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic esters
JPS5910589A (en) * 1982-06-10 1984-01-20 メルク　エンド　カムパニー　インコーポレーテツド Antiinflammatory and analgesic novel 5-(pyrrol-2-oyl)-1,2-dihydro-3h-pyrrolo(1,2-a) pyrrole derivative
US4511724A (en) * 1982-06-10 1985-04-16 Merck & Co., Inc. 5-(Pyrrol-2-oyl)-1,2-dihydro-3H-pyrrolo [1,2-a]pyrrole derivatives as anti-inflammatory and analgesic agents
HU198927B (en) * 1987-01-14 1989-12-28 Richter Gedeon Vegyeszet Process for producing 1-/substituted aminomethyl/-octa-hydroindolo-(2,3-a)quinolizine derivatives, pharmaceutically applicable acid addition salts thereof, as well as pharmaceutical compositions comprising same
US4874871A (en) * 1987-03-25 1989-10-17 Syntex (U.S.A.) Inc. Process for preparing (+)-2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and related compounds

Also Published As

Publication number Publication date
MY8100371A (en) 1981-12-31
YU43157B (en) 1989-04-30
NL7707652A (en) 1978-01-17
AR218631A1 (en) 1980-06-30
JPS539789A (en) 1978-01-28
DK152652C (en) 1988-09-12
JPS6254110B2 (en) 1987-11-13
AU2697677A (en) 1979-01-18
FI772154A7 (en) 1978-01-15
PT66779A (en) 1977-08-01
FR2361396A1 (en) 1978-03-10
IL52492A0 (en) 1977-10-31
YU43156B (en) 1989-04-30
FR2361396B1 (en) 1981-11-27
IE45302L (en) 1978-01-14
SU664566A3 (en) 1979-05-25
NO772493L (en) 1978-01-17
SE434644B (en) 1984-08-06
NO147563B (en) 1983-01-24
DK152652B (en) 1988-04-05
AU513385B2 (en) 1980-11-27
DK307677A (en) 1978-01-15
CS208724B2 (en) 1981-09-15
CH644861A5 (en) 1984-08-31
ES460705A1 (en) 1979-10-01
IE45302B1 (en) 1982-07-28
PT66779B (en) 1978-12-18
PL199602A1 (en) 1979-01-29
DE2731662A1 (en) 1978-01-19
CH651045A5 (en) 1985-08-30
YU47683A (en) 1984-04-30
PL111408B1 (en) 1980-08-30
CA1100140A (en) 1981-04-28
SU793400A3 (en) 1980-12-30
FI63407C (en) 1983-06-10
FI63407B (en) 1983-02-28
SE7708142L (en) 1978-01-15
YU47583A (en) 1984-06-30
DE2731662C2 (en) 1989-11-09
NZ184611A (en) 1979-03-28
IL52492A (en) 1981-06-29
NO147563C (en) 1983-05-18
ES470213A1 (en) 1979-09-16
IT1117314B (en) 1986-02-17
HK17581A (en) 1981-05-08
GR61607B (en) 1978-12-02

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
704A Declaration that licence is not available as of right for an excepted use (par. 4a/1977)
PCNP Patent ceased through non-payment of renewal fee