GB1337315A - 5-aminopyrazole derivatives - Google Patents

5-aminopyrazole derivatives

Info

Publication number
GB1337315A
GB1337315A GB3428671A GB3428671A GB1337315A GB 1337315 A GB1337315 A GB 1337315A GB 3428671 A GB3428671 A GB 3428671A GB 3428671 A GB3428671 A GB 3428671A GB 1337315 A GB1337315 A GB 1337315A
Authority
GB
United Kingdom
Prior art keywords
compounds
meo
halide
alkyl
formula
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
GB3428671A
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.)
Welfide Corp
Original Assignee
Welfide Corp
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 JP11095270A external-priority patent/JPS4920780B1/ja
Priority claimed from JP12908370A external-priority patent/JPS4915263B1/ja
Priority claimed from JP12908270A external-priority patent/JPS4915262B1/ja
Priority claimed from JP12908170A external-priority patent/JPS4921138B1/ja
Priority claimed from JP1809471A external-priority patent/JPS5417739B1/ja
Priority claimed from JP1809671A external-priority patent/JPS5417740B1/ja
Application filed by Welfide Corp filed Critical Welfide Corp
Publication of GB1337315A publication Critical patent/GB1337315A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1337315 Aminopyrazole derivatives YOSHITOMI PHARMACEUTICAL INDUSTRIES Ltd 21 July 1971 [30 July 1970 11 Dec 1970 23 Dec 1970 (3) 27 March 1971 (2) 12 April 1971] 34286/71 Heading C2C The invention comprises compounds of formula and their pharmaceutically acceptable acid addition salts, wherein Y is NH, O or NOH; R<SP>1</SP> is C 1-3 alkyl or allyl; R<SP>2</SP>, R<SP>3</SP> are each H, C 1-3 alkyl, allyl, benzyl, EtO 2 C, HCO, MeCO or EtCO, or NR<SP>2</SP>R<SP>3</SP> is pyrrolidino, piperidino, morpholino, 4 - methylpiperazino, 4 - methylhomopiperazino, or 4(2 - hydroxyethyl)- piperazino, or R<SP>1</SP>-R<SP>2</SP> is CH 2 CH 2 ; R<SP>4</SP> is H, Me or Et; and X<SP>1</SP>, X<SP>2</SP> are each H, halogen, CF 3 , Me or MeO, but excluding the compounds where Y is O, R<SP>1</SP> is C 1-3 alkyl, R<SP>2</SP> is H, R<SP>3</SP> is H or Me, R<SP>4</SP> is Me or Et and X<SP>1</SP>X<SP>2</SP>C 6 H 3 is Ph, YC 6 H 4 (Y=F, Cl, Br, CF 3 , Me or MeO) or 2,3-Cl(MeO)C 6 H 3 . These compounds may be prepared by reacting (1) a 5-amino-4-cyano-1- R<SP>1</SP> - 3 - R<SP>4</SP> - pyrazole with (possibly substituted) LiPh or PhMg-halide, and optionally hydrolysing the resulting imine to the ketone; (2) X<SP>1</SP>X<SP>2</SP>C 6 H 3 COCH(COR<SP>4</SP>)-halide with (3) a pyrazolooxazine of formula where R<SP>5</SP> is H, Me or Et with (possibly substituted) LiPh or PhMg-halide, and optionally hydrolysing the 5-NHCOR<SP>5</SP> group to -NH 2 ; (4) a compound I (R<SP>2</SP>-R<SP>3</SP>=H) with R<SP>5</SP>CO 2 H or a functional derivative thereof; (5) the ketone I (Y=O) with NH 2 OH to give the oxime I (Y=NOH); (6) a corresponding 5-Z-pyrazole (Y=O) where Z is halogen or C 1-4 alkylthio with R<SP>2</SP>R<SP>3</SP>NH. Therapeutic compositions having analgesic, anti-inflammatory and muscle-relaxant activity comprise compounds of Formula I, which may be administered orally or parenterally.
GB3428671A 1970-07-30 1971-07-21 5-aminopyrazole derivatives Expired GB1337315A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP6707470 1970-07-30
JP11095270A JPS4920780B1 (en) 1970-12-11 1970-12-11
JP12908370A JPS4915263B1 (en) 1970-12-23 1970-12-23
JP12908270A JPS4915262B1 (en) 1970-12-23 1970-12-23
JP12908170A JPS4921138B1 (en) 1970-12-23 1970-12-23
JP1809471A JPS5417739B1 (en) 1971-03-27 1971-03-27
JP1809671A JPS5417740B1 (en) 1971-03-27 1971-03-27
JP2321571 1971-04-12

Publications (1)

Publication Number Publication Date
GB1337315A true GB1337315A (en) 1973-11-14

Family

ID=27571839

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3428671A Expired GB1337315A (en) 1970-07-30 1971-07-21 5-aminopyrazole derivatives

Country Status (2)

Country Link
CA (1) CA992964A (en)
GB (1) GB1337315A (en)

Also Published As

Publication number Publication date
CA992964A (en) 1976-07-13

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee