GB1209326A - The preparation of 3-methyl-5-pyrazole carboxylic acid amides - Google Patents
The preparation of 3-methyl-5-pyrazole carboxylic acid amidesInfo
- Publication number
- GB1209326A GB1209326A GB42957/67A GB4295767A GB1209326A GB 1209326 A GB1209326 A GB 1209326A GB 42957/67 A GB42957/67 A GB 42957/67A GB 4295767 A GB4295767 A GB 4295767A GB 1209326 A GB1209326 A GB 1209326A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- acid amides
- amine
- sept
- ammonia
- 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
Links
- WRKWQCNJAZPEKK-UHFFFAOYSA-N 5-methyl-1h-pyrazole-3-carboxamide Chemical class CC=1C=C(C(N)=O)NN=1 WRKWQCNJAZPEKK-UHFFFAOYSA-N 0.000 title abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- -1 piperidono Chemical group 0.000 abstract 2
- 150000003141 primary amines Chemical class 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- OYQVQWIASIXXRT-UHFFFAOYSA-N ethyl 2,4-dioxopentanoate Chemical compound CCOC(=O)C(=O)CC(C)=O OYQVQWIASIXXRT-UHFFFAOYSA-N 0.000 abstract 1
- BOTXQJAHRCGJEG-UHFFFAOYSA-N ethyl 5-methyl-1h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C)NN=1 BOTXQJAHRCGJEG-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,209,326. 3-Methyl-5-pyrazolecarboxylic acid amides. CARTER WALLACE Inc. 21 Sept., 1967 [27 Sept., 1966], No. 42957/67. Heading C2C. [Also in Division A5] 3 - Methyl - 5 - pyrazolecarboxylic acid amides of the formula wherein R is NH 2 or a radical of a substituted o<SP>r</SP> unsubstituted primary or secondary amine (the compounds in which R in the above formula represents morpholino, piperidono, benzylamino and p-chlorobenzylamino being novel) are prepared by treating ethyl acetopyruvate, dissolved in glacial acetic acid, with hydrazine hydrate, cooling to cause ethyl 3-methyl-5- pyrazole carboxylate to precipitate, reacting said ester with ammonia or primary or secondary amine in stoichiometrically equivalent proportions in an aqueous alcoholic solution, in an excess of the amine, or in aqueous solution containing an excess of the amine or ammonia, flreuxing for 4 to 15 hours and collecting the precipitated amide. Reference has been directed by the Comptroller to Specification 1,048,104.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2213566A IT1053661B (en) | 1966-09-27 | 1966-09-27 | AMID OF ACID 3 5 METHYL 5 3 PYRAZOL CARBOXYLIC |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1209326A true GB1209326A (en) | 1970-10-21 |
Family
ID=11192002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42957/67A Expired GB1209326A (en) | 1966-09-27 | 1967-09-21 | The preparation of 3-methyl-5-pyrazole carboxylic acid amides |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE704290A (en) |
| CH (1) | CH479588A (en) |
| DE (1) | DE1670466A1 (en) |
| ES (1) | ES345849A1 (en) |
| FR (1) | FR7254M (en) |
| GB (1) | GB1209326A (en) |
| IT (1) | IT1053661B (en) |
| NL (1) | NL6713145A (en) |
| SE (1) | SE333147B (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005077909A1 (en) * | 2004-02-17 | 2005-08-25 | Laboratorios Dr. Esteve S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| EP1637522A1 (en) * | 2004-09-16 | 2006-03-22 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| EP1743889A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | Sustituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| EP1746090A1 (en) * | 2005-07-15 | 2007-01-24 | Laboratorios del Dr. Esteve S.A. | Sustituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| WO2007009702A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| WO2007009706A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| EP1950202A1 (en) * | 2007-01-24 | 2008-07-30 | Laboratorios del Dr. Esteve S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments with ACAT inhibition activity |
| US7524868B2 (en) | 2004-02-17 | 2009-04-28 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| US7659408B2 (en) * | 2003-08-07 | 2010-02-09 | Merck Sharp & Dhome Corp. | Pyrazole carboxamides as inhibitors of 11-β-hydroxysteroid dehydrogenase-1 |
| US7897589B2 (en) | 2005-07-15 | 2011-03-01 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| US7968582B2 (en) | 2005-07-15 | 2011-06-28 | Laborotorios Del Dr. Esteve, S.A. | 5(S)-substituted pyrazoline compounds, their preparation and use as medicaments |
| US7994200B2 (en) | 2005-07-15 | 2011-08-09 | Laboratorios Del Dr. Esteve, S.A. | Cycloalkane-substituted pyrazoline derivatives, their preparation and use as medicaments |
| US7998996B2 (en) | 2004-02-17 | 2011-08-16 | Laboratorios Del Dr. Esteve S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495195A (en) * | 1982-11-01 | 1985-01-22 | Eli Lilly And Company | Xanthine oxidase inhibiting 3(5)-phenyl-substituted-5(3)-pyrazole-carboxylic acid derivatives, compositions, and methods of use |
-
1966
- 1966-09-27 IT IT2213566A patent/IT1053661B/en active
-
1967
- 1967-09-20 DE DE19671670466 patent/DE1670466A1/en active Pending
- 1967-09-21 GB GB42957/67A patent/GB1209326A/en not_active Expired
- 1967-09-25 CH CH1335167A patent/CH479588A/en not_active IP Right Cessation
- 1967-09-26 BE BE704290D patent/BE704290A/xx unknown
- 1967-09-26 ES ES345849A patent/ES345849A1/en not_active Expired
- 1967-09-27 SE SE1328867A patent/SE333147B/en unknown
- 1967-09-27 NL NL6713145A patent/NL6713145A/xx unknown
- 1967-12-26 FR FR133764A patent/FR7254M/fr not_active Expired
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7659408B2 (en) * | 2003-08-07 | 2010-02-09 | Merck Sharp & Dhome Corp. | Pyrazole carboxamides as inhibitors of 11-β-hydroxysteroid dehydrogenase-1 |
| JP2007522252A (en) * | 2004-02-17 | 2007-08-09 | ラボラトリオス・デル・ドクトル・エステベ・ソシエダッド・アノニマ | Substituted pyrazoline compounds, their preparation and their use as pharmaceuticals |
| US7998996B2 (en) | 2004-02-17 | 2011-08-16 | Laboratorios Del Dr. Esteve S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| WO2005077909A1 (en) * | 2004-02-17 | 2005-08-25 | Laboratorios Dr. Esteve S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| US7524868B2 (en) | 2004-02-17 | 2009-04-28 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1637522A1 (en) * | 2004-09-16 | 2006-03-22 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds for reducing triglycerides in blood |
| WO2007009702A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| WO2007009706A3 (en) * | 2005-07-15 | 2007-04-19 | Esteve Labor Dr | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| WO2007009702A3 (en) * | 2005-07-15 | 2007-04-05 | Esteve Labor Dr | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| WO2007009706A2 (en) * | 2005-07-15 | 2007-01-25 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| EP1746090A1 (en) * | 2005-07-15 | 2007-01-24 | Laboratorios del Dr. Esteve S.A. | Sustituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| US7897589B2 (en) | 2005-07-15 | 2011-03-01 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| US7968582B2 (en) | 2005-07-15 | 2011-06-28 | Laborotorios Del Dr. Esteve, S.A. | 5(S)-substituted pyrazoline compounds, their preparation and use as medicaments |
| US7994200B2 (en) | 2005-07-15 | 2011-08-09 | Laboratorios Del Dr. Esteve, S.A. | Cycloalkane-substituted pyrazoline derivatives, their preparation and use as medicaments |
| EP1743889A1 (en) * | 2005-07-15 | 2007-01-17 | Laboratorios del Dr. Esteve S.A. | Sustituted pyrazoline compounds, having predetermined stereochemistry, for reducing triglycerides in blood |
| US8106085B2 (en) | 2005-07-15 | 2012-01-31 | Laboratorios Del Dr. Esteve, S.A. | Indoline-substituted pyrazoline derivatives, their preparation and use as medicaments |
| US8207156B2 (en) | 2005-07-15 | 2012-06-26 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| EP1950202A1 (en) * | 2007-01-24 | 2008-07-30 | Laboratorios del Dr. Esteve S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments with ACAT inhibition activity |
Also Published As
| Publication number | Publication date |
|---|---|
| FR7254M (en) | 1969-09-08 |
| DE1670466A1 (en) | 1972-01-27 |
| ES345849A1 (en) | 1968-11-16 |
| NL6713145A (en) | 1968-03-28 |
| BE704290A (en) | 1968-02-01 |
| CH479588A (en) | 1969-10-15 |
| SE333147B (en) | 1971-03-08 |
| IT1053661B (en) | 1981-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |