IE35377B1 - Improvements in or relating to pyrazole derivatives - Google Patents

Improvements in or relating to pyrazole derivatives

Info

Publication number
IE35377B1
IE35377B1 IE1175/70A IE117570A IE35377B1 IE 35377 B1 IE35377 B1 IE 35377B1 IE 1175/70 A IE1175/70 A IE 1175/70A IE 117570 A IE117570 A IE 117570A IE 35377 B1 IE35377 B1 IE 35377B1
Authority
IE
Ireland
Prior art keywords
hydrolysing
reacting
alkyl
dimethyl
compound
Prior art date
Application number
IE1175/70A
Other versions
IE35377L (en
Original Assignee
Byk Gulden Lomberg Chem Fab
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 Byk Gulden Lomberg Chem Fab filed Critical Byk Gulden Lomberg Chem Fab
Publication of IE35377L publication Critical patent/IE35377L/en
Publication of IE35377B1 publication Critical patent/IE35377B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1307005 Derivatives of pyrazole-4-acetic acid BYK GULDEN LOMBERG CHEMISCHE FABRIK GmbH 9 Sept 1970 [12 Sept 1969] 43147/70 Heading C2C The invention comprises compounds of formula and their salts with pharmacologically compatible bases, wherein R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP> are each H, an (up to C 7 ) aliphatic or cycloaliphatic hydrocarbon radical, or an (up to C 12 ) optionally substituted (otherwise than by NO 2 ) aryl or heteroaryl group, or R<SP>1</SP> is benzyl (optionally halogen- or C 1-4 alkoxy-substituted), provided that when R 2 is H, R 3 may not be H or Me; R<SP>4</SP> is H, C 1-3 alkyl or C 3-6 cycloalkyl; and A is,CO 2 H, CO 2 R<SP>5</SP>, CONR<SP>6</SP>R<SP>7</SP>, CN or C(:NOH)OH, where R<SP>5</SP> is C 1-4 alkyl, benzyl, Ph or 2-HO 2 CC 6 H 4 , and R<SP>6</SP>, R<SP>7</SP> are each H or C 1-4 alkyl, or NR<SP>6</SP>R<SP>7</SP> is pyrrolidino, piperidino or morpholino. The following preparative methods are exemplified: (1) reacting R<SP>2</SP>CMe NNHR<SP>1</SP> with reaction product and hydrolysing the compound thus formed (or alternatively first forming from the initial product the N,N.dimethyl-4-pyrazolyl. methyleneiminium perchlorate, and hydrolysing this) to give the corresponding 4-formylpyrazole, reducing the latter to the 4-hydroxymethylpyrazole, converting this via the 4-chloromethylpyrazole to the 4-cyanomethyl compound and optionally hydrolysing this to the acid; (2) reacting the diketo ester with R<SP>1</SP>NHNH 2 ; (3) reacting an alkyl-3-acyl-4- dialkylamino - 3 - butenoate with R<SP>1</SP>NHNH 2 ; (4) interconversion of acids, esters, nitriles, and amides, by known methods; (5) reacting the corresponding acid chloride with HNR<SP>6</SP>R<SP>7</SP> or with NH 2 OH; (6) reacting a compound where R<SP>1</SP> =Na, with R<SP>1</SP>-halide (R<SP>1</SP>#H), (7:) hydrolysing (e.g.) 3,5 - dimethyl - 1 - phenyl - 4 - pyrazolethioacetmorpholide to the corresponding acid; (8) hydrolysing (e.g.) ethyl 3,5-dimethyl-1- phenyl - 4 - pyrazoleacetimidate to the corresponding acetate. Therapeutic compositions for oral, parenteral or rectal administration comprise compounds of the above formula, which have antiphlogistic, analgesic and antipyretic properties. [GB1307005A]
IE1175/70A 1969-09-12 1970-09-10 Improvements in or relating to pyrazole derivatives IE35377B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1946370A DE1946370C3 (en) 1969-09-12 1969-09-12 Substituted pyrazole-4-acetic acids, processes for their preparation and pharmaceuticals containing them

Publications (2)

Publication Number Publication Date
IE35377L IE35377L (en) 1971-03-12
IE35377B1 true IE35377B1 (en) 1976-02-04

Family

ID=5745381

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1175/70A IE35377B1 (en) 1969-09-12 1970-09-10 Improvements in or relating to pyrazole derivatives

Country Status (13)

Country Link
JP (2) JPS5133906B1 (en)
AT (2) AT304534B (en)
BE (1) BE755924A (en)
CA (1) CA959838A (en)
CH (2) CH583707A5 (en)
DE (1) DE1946370C3 (en)
FR (1) FR2070689B1 (en)
GB (1) GB1307005A (en)
HK (1) HK23578A (en)
IE (1) IE35377B1 (en)
NL (1) NL7013384A (en)
SE (1) SE385212B (en)
ZA (1) ZA706215B (en)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4146721A (en) * 1969-09-12 1979-03-27 Byk Gulden Lomberg Chemische Fabrik Gmbh Pyrazol-4-acetic acid compounds
GB1373212A (en) * 1970-12-07 1974-11-06 Wyeth John & Brother Ltd Pyrazole compounds
US3984431A (en) * 1972-03-15 1976-10-05 Claude Gueremy Derivatives of pyrazole-5-acetic acid
US4042702A (en) 1973-08-16 1977-08-16 Byk Gulden Lomberg Chemische Fabrik Gmbh Halogen pyrazole derivatives, a method for producing these halogen pyrazole derivatives, medicaments containing and methods of using them
DK115374A (en) 1974-03-04 1975-11-03 Byk Gulden Lomberg Chem Fab
DE2633992A1 (en) * 1975-08-08 1978-02-09 Schering Ag Antiinflammatory (1,4)-diphenyl-(3)-alkyl-carboxy-pyrazole - prepd. by treating corresp. (3)-halide with a cyanide, and opt. hydrolysing or reducing
DE2536003C2 (en) * 1975-08-08 1985-11-14 Schering AG, 1000 Berlin und 4709 Bergkamen Pyrazole derivatives, their preparation and pharmaceutical derivatives containing them
DE2906252A1 (en) * 1979-02-19 1980-08-28 Merck Patent Gmbh PYRAZOLE DERIVATIVES, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND METHOD FOR THE PRODUCTION THEREOF
US4826868A (en) * 1986-05-29 1989-05-02 Ortho Pharmaceutical Corporation 1,5-Diaryl-3-substituted pyrazoles pharmaceutical compositions and use
JPS63307841A (en) * 1987-05-29 1988-12-15 オーソ・フアーマシユーチカル・コーポレーシヨン Manufacture of 1,5-disubstituted pyrazoles
AU611437B2 (en) * 1987-05-29 1991-06-13 Ortho Pharmaceutical Corporation Pharmacologically active 2- and 3-substituted (1',5'-diaryl-3-pyrazolyl)-n-hydroxypropanamides and method for synthesizing the same
US5466823A (en) 1993-11-30 1995-11-14 G.D. Searle & Co. Substituted pyrazolyl benzenesulfonamides
DE10152005A1 (en) * 2001-10-22 2003-04-30 Bayer Cropscience Ag Pyrazolyl substituted heterocycles
DE10331675A1 (en) 2003-07-14 2005-02-10 Bayer Cropscience Ag Hetaryl-substituted pyrazolidinedione derivatives
EP2135865A1 (en) 2008-06-17 2009-12-23 Bayer CropScience AG Substituted 1-(diazinyl)pyrazol-4-yl acetic acids, method for their production and their use as herbicides and plant growth regulators
EP2194052A1 (en) 2008-12-06 2010-06-09 Bayer CropScience AG Substituted 1.(1-thiazolyl)- and 1-(isothiazolyl)pyrazol-4-yl acetic acids, method for their production and their use as herbicides and plant growth regulators
WO2011073098A1 (en) 2009-12-15 2011-06-23 Bayer Cropscience Ag 1-(heteroaryl)-pyrazol-4-yl-acetic acids, method for the production thereof, and the use thereof as herbicides and plant growth regulators

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1182412A (en) * 1956-08-03 1959-06-25 Geigy Ag J R Novel heterocyclic carboxylic acids of the pyrazole series and their esters and salts and the preparation of these compounds

Also Published As

Publication number Publication date
DE1946370B2 (en) 1978-11-09
DE1946370C3 (en) 1979-07-26
BE755924A (en) 1971-02-15
FR2070689B1 (en) 1974-08-30
CA959838A (en) 1974-12-24
IE35377L (en) 1971-03-12
AT313274B (en) 1974-02-11
GB1307005A (en) 1973-02-14
SE385212B (en) 1976-06-14
NL7013384A (en) 1971-03-16
HK23578A (en) 1978-05-12
JPS5133906B1 (en) 1976-09-22
JPS5339435B1 (en) 1978-10-21
CH583707A5 (en) 1977-01-14
ZA706215B (en) 1971-05-27
FR2070689A1 (en) 1971-09-17
AT304534B (en) 1973-01-10
CH587251A5 (en) 1977-04-29
DE1946370A1 (en) 1971-04-22

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