IE35377L - Pyrazole derivatives - Google Patents
Pyrazole derivativesInfo
- Publication number
- IE35377L IE35377L IE701175A IE117570A IE35377L IE 35377 L IE35377 L IE 35377L IE 701175 A IE701175 A IE 701175A IE 117570 A IE117570 A IE 117570A IE 35377 L IE35377 L IE 35377L
- Authority
- IE
- Ireland
- Prior art keywords
- hydrolysing
- reacting
- alkyl
- dimethyl
- compound
- Prior art date
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
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- 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]
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 true IE35377L (en) | 1971-03-12 |
IE35377B1 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)
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)
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 |
-
0
- BE BE755924D patent/BE755924A/en not_active IP Right Cessation
-
1969
- 1969-09-12 DE DE1946370A patent/DE1946370C3/en not_active Expired
-
1970
- 1970-08-28 CH CH346073A patent/CH583707A5/xx not_active IP Right Cessation
- 1970-08-28 CH CH1290470A patent/CH587251A5/xx not_active IP Right Cessation
- 1970-09-09 GB GB4314770A patent/GB1307005A/en not_active Expired
- 1970-09-10 CA CA092,873A patent/CA959838A/en not_active Expired
- 1970-09-10 SE SE7012345A patent/SE385212B/en unknown
- 1970-09-10 IE IE1175/70A patent/IE35377B1/en unknown
- 1970-09-10 NL NL7013384A patent/NL7013384A/xx unknown
- 1970-09-11 JP JP45079421A patent/JPS5133906B1/ja active Pending
- 1970-09-11 FR FR7033102A patent/FR2070689B1/fr not_active Expired
- 1970-09-11 AT AT826170A patent/AT304534B/en not_active IP Right Cessation
- 1970-09-11 ZA ZA706215A patent/ZA706215B/en unknown
- 1970-09-11 AT AT188472A patent/AT313274B/en active
-
1974
- 1974-06-05 JP JP6298874A patent/JPS5339435B1/ja active Pending
-
1978
- 1978-05-04 HK HK235/78A patent/HK23578A/en unknown
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 |
IE35377B1 (en) | 1976-02-04 |
CA959838A (en) | 1974-12-24 |
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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