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GB1427945A - Aminopyrrole derivatives - Google Patents

Aminopyrrole derivatives

Info

Publication number
GB1427945A
GB1427945A GB3979073A GB3979073A GB1427945A GB 1427945 A GB1427945 A GB 1427945A GB 3979073 A GB3979073 A GB 3979073A GB 3979073 A GB3979073 A GB 3979073A GB 1427945 A GB1427945 A GB 1427945A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
alkyl
hydrogen
carbo
carbamyl
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
GB3979073A
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.)
Gruppo Lepetit SpA
Original Assignee
Gruppo Lepetit SpA
Lepetit SpA
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 Gruppo Lepetit SpA, Lepetit SpA filed Critical Gruppo Lepetit SpA
Priority to GB3979073A priority Critical patent/GB1427945A/en
Priority to ZA00744754A priority patent/ZA744754B/en
Priority to IL45368A priority patent/IL45368A/en
Priority to YU2141/74A priority patent/YU36926B/en
Priority to NO742862A priority patent/NO143845C/en
Priority to IE1672/74A priority patent/IE40290B1/en
Priority to AU72210/74A priority patent/AU481957B2/en
Priority to DE2462967A priority patent/DE2462967C2/en
Priority to DD180545A priority patent/DD113756A5/xx
Priority to DE2462963A priority patent/DE2462963C2/en
Priority to DE2439284A priority patent/DE2439284C2/en
Priority to DE2462966A priority patent/DE2462966C2/en
Priority to RO79830A priority patent/RO72882B/en
Priority to RO7491734A priority patent/RO70534A/en
Priority to RO7491735A priority patent/RO70535A/en
Priority to LU70764A priority patent/LU70764A1/xx
Priority to IN1864/CAL/1974A priority patent/IN140329B/en
Priority to NL7411092A priority patent/NL7411092A/en
Priority to CA207,472A priority patent/CA1050556A/en
Priority to JP9600974A priority patent/JPS5328914B2/ja
Priority to HULE754A priority patent/HU169728B/hu
Priority to CH1142674A priority patent/CH605741A5/xx
Priority to SU742055571A priority patent/SU843738A3/en
Priority to SE7410636A priority patent/SE394429B/en
Priority to FI2462/74A priority patent/FI61879C/en
Priority to DK445974A priority patent/DK156391C/en
Priority to PL1974189700A priority patent/PL96806B1/en
Priority to CS745833A priority patent/CS188201B2/en
Priority to BE147818A priority patent/BE819088A/en
Priority to PL1974173617A priority patent/PL95235B1/pl
Priority to ES429446A priority patent/ES429446A1/en
Priority to AT684774A priority patent/AT336600B/en
Priority to FR7428894A priority patent/FR2241308B1/fr
Priority to AR255253A priority patent/AR210246A1/en
Publication of GB1427945A publication Critical patent/GB1427945A/en
Priority to AR263503A priority patent/AR210133A1/en
Priority to AR263502A priority patent/AR210132A1/en
Priority to ES449426A priority patent/ES449426A1/en
Priority to ES449425A priority patent/ES449425A1/en
Priority to US05/750,759 priority patent/US4140696A/en
Priority to US05/960,384 priority patent/US4198502A/en
Priority to US05/960,385 priority patent/US4211708A/en
Priority to US05/960,387 priority patent/US4212806A/en
Priority to US05/960,386 priority patent/US4211709A/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
    • C07D207/34—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
    • C07D207/36—Oxygen or sulfur atoms
    • 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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Rheumatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pain & Pain Management (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)

Abstract

1427945 Derivatives of 3-aminopyrrole GRUPPO LEPETIT SpA 25 July 1974 [22 Aug 1973] 39790/73 Heading C2C The invention comprises compounds of formula and their salts with pharmaceutically acceptable acids, wherein R is hydrogen, (C 1-4 )alkyl, benzyl or halo-substituted benzyl; R 1 is hydrogen, (C 1-4 )alkyl, phenyl or phenyl carrying one to three substituents chosen from (C 1-4 )alkyl, (C 1-4 )alkoxy, benzyloxy, fluoro, chloro, bromo, hydroxy and nitro; R 2 is hydrogen, (C 1-4 )alkyl, formyl, (C 2-4 )aliphatic acyl, benzoyl, carbo- (C 1-4 )alkoxy -(C 2-4 )aliphatic acyl, carbamyl, phenylcarbamyl, thiocarbamyl, phenylthiocarbamyl, benzoylthiocarbamyl, carboxyphenyl, benzenesulphonyl, (C 1-4 )alkylsulphonyl, toluenesulphonyl or phenacylsulphonyl; R 3 is hydrogen or (C 1-4 )alkyl or R 2 and R 3 together are (C 2-4 )alkylidene, benzylidene or halo-substituted benzylidene; R 4 is (C 2-4 )- aliphatic acyl, benzoyl, benzoyl carrying one to three substituents chosen from fluoro, chloro, bromo and (C 1-4 )alkoxy, carbo(C 1-4 )alkoxy, carboxy, carbamyl, methylcarbamyl or phenylcarbamyl and R 5 is hydrogen, (C 1-4 )alkyl, carbo(C 1-4 )alkoxy, carbo (C 1-4 )alkoxy-methyl, trifluoromethyl, carboxy, carbamyl or carbazoyl or R 4 and R 5 together are -CO-(CH 2 ) n -, wherein the carbonyl group is connected to the carbon atom of the pyrrole ring which bears the substituent R 4 and n is 2, 3 or 4, provided that when R 1 =R 5 =Me and R=H, then one of R 2 , R 3 #H and R 4 #CO 2 Et. These compounds are prepared (when R=R 2 =R 3 =H) by reacting RNH-CHR 1 -CN with either R 2 COCH 2 R 4 or R 5 C # CR 4 and cyclizing the thus formed inter-- mediate of formula the products may then be reacted further if desired to convert the 3-NH 2 groups or other functional groups present to different substituent groups and/or replace the 1-H atom by R(#H). Therapeutic compositions having anti-inflammatory antipyretic and analgesic activity, C.N.S. depressant activity, and in some cases sedative and myorelaxing activity, comprise compounds of the above formula, and may be administered orally, parenterally or rectally.
GB3979073A 1973-08-22 1973-08-22 Aminopyrrole derivatives Expired GB1427945A (en)

Priority Applications (43)

Application Number Priority Date Filing Date Title
GB3979073A GB1427945A (en) 1973-08-22 1973-08-22 Aminopyrrole derivatives
ZA00744754A ZA744754B (en) 1973-08-22 1974-07-27 New aminopyrrole derivator
IL45368A IL45368A (en) 1973-08-22 1974-07-29 Aminopyrrole derivatives
YU2141/74A YU36926B (en) 1973-08-22 1974-08-01 Process for obtaining new aminopyrrol derivatives
NO742862A NO143845C (en) 1973-08-22 1974-08-08 ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVITIES 3-AMINO-PYRROLLER DERIVATIVES
IE1672/74A IE40290B1 (en) 1973-08-22 1974-08-08 Wew aminopyrrole derivatives
AU72210/74A AU481957B2 (en) 1973-08-22 1974-08-12 New aminopyrrole derivatives
DE2462967A DE2462967C2 (en) 1973-08-22 1974-08-16 Derivatives of 3-amino-5-methyl-2-phenyl-pyrrole, their salts and pharmaceutical preparations containing them
DD180545A DD113756A5 (en) 1973-08-22 1974-08-16
DE2462963A DE2462963C2 (en) 1973-08-22 1974-08-16 Derivatives of 2-phenyl-3-aminopyrrole, their salts and pharmaceutical preparation containing them
DE2439284A DE2439284C2 (en) 1973-08-22 1974-08-16 2-Phenyl-3-amino-4-acetyl-5-methylpyrrole, its salts and pharmaceutical preparation containing these compounds
DE2462966A DE2462966C2 (en) 1973-08-22 1974-08-16 Derivatives of 3-amino-4-acetyl-5-methylpyrrole and pharmaceutical preparations containing them
RO79830A RO72882B (en) 1973-08-22 1974-08-19 Process for preparing substituted pyrrole
RO7491734A RO70534A (en) 1973-08-22 1974-08-19 PROCESS FOR PREPARATION OF 3-AMINOPYROL DERIVATIVES
RO7491735A RO70535A (en) 1973-08-22 1974-08-19 PROCESS FOR PREPARATION OF 3-AMINOPYROL DERIVATIVES
LU70764A LU70764A1 (en) 1973-08-22 1974-08-20
IN1864/CAL/1974A IN140329B (en) 1973-08-22 1974-08-20
NL7411092A NL7411092A (en) 1973-08-22 1974-08-20 PROCESS FOR THE PREPARATION OF AMINOPYRROOL DERIVATIVES.
CH1142674A CH605741A5 (en) 1973-08-22 1974-08-21
JP9600974A JPS5328914B2 (en) 1973-08-22 1974-08-21
HULE754A HU169728B (en) 1973-08-22 1974-08-21
CA207,472A CA1050556A (en) 1973-08-22 1974-08-21 Aminopyrrole derivatives
SU742055571A SU843738A3 (en) 1973-08-22 1974-08-21 Method of preparing derivatives of aminopyrrole or its salts
SE7410636A SE394429B (en) 1973-08-22 1974-08-21 PROCEDURE FOR THE PREPARATION OF AMINOPYR ROLE DERIVATIVES WITH THERAPEUTIC EFFECT
FI2462/74A FI61879C (en) 1973-08-22 1974-08-21 ANALOGIFICATE FARMS FOR FRAMSTAELLNING AV NYA THERAPEUTIC EFFECTIVE AMINOPYRROLDERIVAT
DK445974A DK156391C (en) 1973-08-22 1974-08-21 ANALOGY PROCEDURE FOR PREPARING 3-AMINOPYR ROLLER DERIVATIVES
AT684774A AT336600B (en) 1973-08-22 1974-08-22 Process for the preparation of new aminopyrrole derivatives and their salts
CS745833A CS188201B2 (en) 1973-08-22 1974-08-22 Method of producing novel derivatives of amino pyrrole
BE147818A BE819088A (en) 1973-08-22 1974-08-22 NEW AMINOPYRROLE DERIVATIVES AND THEIR PREPARATION
PL1974173617A PL95235B1 (en) 1973-08-22 1974-08-22
ES429446A ES429446A1 (en) 1973-08-22 1974-08-22 PROCEDURE TO PREPARE AMINOPYRROL DERIVATIVES.
PL1974189700A PL96806B1 (en) 1973-08-22 1974-08-22 METHOD OF MAKING NEW DERIVATIVES OF AMINOPIROL
FR7428894A FR2241308B1 (en) 1973-08-22 1974-08-22
AR255253A AR210246A1 (en) 1973-08-22 1974-08-27 PROCEDURE TO PREPARE NEW 2-, 4-AND5-SUBSTITUTED DERIVATIVES OF 3-AMINOPYRROL
AR263502A AR210132A1 (en) 1973-08-22 1976-06-03 PROCEDURE FOR PREPARING NEW 3-AMINO-4-ACETYL-5-METHYL-PIRROL DERIVATIVES
AR263503A AR210133A1 (en) 1973-08-22 1976-06-03 PROCEDURE FOR PREPARING NEW DERIVATIVES OF 3-AMINO-5-METHYL-PIRROL
ES449426A ES449426A1 (en) 1973-08-22 1976-07-01 PROCEDURE TO PREPARE AMINOPYRROL DERIVATIVES.
ES449425A ES449425A1 (en) 1973-08-22 1976-07-01 Aminopyrrole derivatives
US05/750,759 US4140696A (en) 1973-08-22 1976-12-15 Aminopyrrole derivatives
US05/960,384 US4198502A (en) 1973-08-22 1978-11-13 Aminopyrrole derivatives
US05/960,385 US4211708A (en) 1973-08-22 1978-11-13 Aminopyrrole derivatives
US05/960,387 US4212806A (en) 1973-08-22 1978-11-13 Aminopyrrole derivatives
US05/960,386 US4211709A (en) 1973-08-22 1978-11-13 Aminopyrrole derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3979073A GB1427945A (en) 1973-08-22 1973-08-22 Aminopyrrole derivatives

Publications (1)

Publication Number Publication Date
GB1427945A true GB1427945A (en) 1976-03-10

Family

ID=10411528

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3979073A Expired GB1427945A (en) 1973-08-22 1973-08-22 Aminopyrrole derivatives

Country Status (27)

Country Link
JP (1) JPS5328914B2 (en)
AR (3) AR210246A1 (en)
AT (1) AT336600B (en)
BE (1) BE819088A (en)
CA (1) CA1050556A (en)
CH (1) CH605741A5 (en)
CS (1) CS188201B2 (en)
DD (1) DD113756A5 (en)
DE (4) DE2462963C2 (en)
DK (1) DK156391C (en)
ES (3) ES429446A1 (en)
FI (1) FI61879C (en)
FR (1) FR2241308B1 (en)
GB (1) GB1427945A (en)
HU (1) HU169728B (en)
IE (1) IE40290B1 (en)
IL (1) IL45368A (en)
IN (1) IN140329B (en)
LU (1) LU70764A1 (en)
NL (1) NL7411092A (en)
NO (1) NO143845C (en)
PL (2) PL96806B1 (en)
RO (3) RO72882B (en)
SE (1) SE394429B (en)
SU (1) SU843738A3 (en)
YU (1) YU36926B (en)
ZA (1) ZA744754B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1492663A (en) * 1975-02-20 1977-11-23 Lepetit Spa 4-amino-3-pyrrole carboxamides
GB1548398A (en) * 1975-06-05 1979-07-11 Lilly Industries Ltd Acylamino pyrroles furans and thiophenes
DE3212591A1 (en) * 1982-04-03 1983-10-13 Gödecke AG, 1000 Berlin 2-PYRROLIN-3-CARBONITRIL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THE SAME
JPH0216740U (en) * 1988-07-21 1990-02-02
DE59009489D1 (en) * 1989-03-28 1995-09-14 Ciba Geigy Ag Substituted aminopyrroles as stabilizers, chlorine-containing polymers.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1148909A (en) * 1965-04-19 1969-04-16 Sumitomo Chemical Co Process for production of novel phenylhydrazone and phenylhydrazine derivatives
GB1187903A (en) * 1967-09-29 1970-04-15 Sumitomo Chemical Co Glucuronides of 3-Indolylaliphatic Acid Derivatives and Processes for Producing them

Also Published As

Publication number Publication date
ES449426A1 (en) 1977-07-01
AR210246A1 (en) 1977-07-15
ES429446A1 (en) 1977-02-16
DE2462966C2 (en) 1983-12-29
YU214174A (en) 1982-06-18
LU70764A1 (en) 1975-01-02
SE394429B (en) 1977-06-27
YU36926B (en) 1984-08-31
SE7410636L (en) 1975-02-24
PL96806B1 (en) 1978-01-31
CH605741A5 (en) 1978-10-13
DK156391C (en) 1990-01-08
FI61879B (en) 1982-06-30
IN140329B (en) 1976-10-16
NO143845C (en) 1981-04-22
RO72882B (en) 1987-02-28
DE2462967C2 (en) 1982-12-02
DD113756A5 (en) 1975-06-20
JPS5328914B2 (en) 1978-08-17
AR210132A1 (en) 1977-06-30
AU7221074A (en) 1976-02-12
PL95235B1 (en) 1977-09-30
CA1050556A (en) 1979-03-13
NO742862L (en) 1975-03-24
FR2241308B1 (en) 1977-09-09
DK445974A (en) 1975-04-28
IL45368A0 (en) 1974-10-22
DK156391B (en) 1989-08-14
RO72882A (en) 1987-02-27
FI246274A7 (en) 1975-02-23
ATA684774A (en) 1976-09-15
CS188201B2 (en) 1979-02-28
IE40290L (en) 1975-02-22
DE2439284A1 (en) 1975-03-06
FI61879C (en) 1982-10-11
BE819088A (en) 1974-12-16
RO70534A (en) 1981-07-30
SU843738A3 (en) 1981-06-30
IL45368A (en) 1977-10-31
NO143845B (en) 1981-01-12
HU169728B (en) 1977-02-28
ZA744754B (en) 1975-08-27
NL7411092A (en) 1975-02-25
RO70535A (en) 1981-08-17
DE2439284C2 (en) 1982-07-29
JPS5070356A (en) 1975-06-11
FR2241308A1 (en) 1975-03-21
ES449425A1 (en) 1977-07-01
DE2462963C2 (en) 1982-12-02
IE40290B1 (en) 1979-04-25
AR210133A1 (en) 1977-06-30
AT336600B (en) 1977-05-10

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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

Effective date: 19920725