JP7291782B2 - 3-[5-アミノ-4-(3-シアノベンゾイル)-ピラゾール化合物の調製のための合成方法 - Google Patents
3-[5-アミノ-4-(3-シアノベンゾイル)-ピラゾール化合物の調製のための合成方法 Download PDFInfo
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- JP7291782B2 JP7291782B2 JP2021516883A JP2021516883A JP7291782B2 JP 7291782 B2 JP7291782 B2 JP 7291782B2 JP 2021516883 A JP2021516883 A JP 2021516883A JP 2021516883 A JP2021516883 A JP 2021516883A JP 7291782 B2 JP7291782 B2 JP 7291782B2
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- DSGOECBBNQENSY-UHFFFAOYSA-N 3-[5-amino-4-(3-cyanobenzoyl)pyrazol-1-yl]-4-methylbenzoic acid Chemical compound NC1=C(C=NN1C=1C=C(C(=O)O)C=CC=1C)C(C1=CC(=CC=C1)C#N)=O DSGOECBBNQENSY-UHFFFAOYSA-N 0.000 description 5
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- XKFIFYROMAAUDL-UHFFFAOYSA-N 3-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N XKFIFYROMAAUDL-UHFFFAOYSA-N 0.000 description 3
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- 231100000583 toxicological profile Toxicity 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
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- 238000002955 isolation Methods 0.000 description 2
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
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- 125000003944 tolyl group Chemical group 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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- SGJBIFUEFLWXJY-UHFFFAOYSA-N 1-(dibutoxymethoxy)butane Chemical compound CCCCOC(OCCCC)OCCCC SGJBIFUEFLWXJY-UHFFFAOYSA-N 0.000 description 1
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- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
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- 238000003109 Karl Fischer titration Methods 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- AZFNGPAYDKGCRB-XCPIVNJJSA-M [(1s,2s)-2-amino-1,2-diphenylethyl]-(4-methylphenyl)sulfonylazanide;chlororuthenium(1+);1-methyl-4-propan-2-ylbenzene Chemical compound [Ru+]Cl.CC(C)C1=CC=C(C)C=C1.C1=CC(C)=CC=C1S(=O)(=O)[N-][C@@H](C=1C=CC=CC=1)[C@@H](N)C1=CC=CC=C1 AZFNGPAYDKGCRB-XCPIVNJJSA-M 0.000 description 1
- BVQHHUQLZPXYAQ-UHFFFAOYSA-N acetyl butanoate Chemical compound CCCC(=O)OC(C)=O BVQHHUQLZPXYAQ-UHFFFAOYSA-N 0.000 description 1
- KLUDQUOLAFVLOL-UHFFFAOYSA-N acetyl propanoate Chemical compound CCC(=O)OC(C)=O KLUDQUOLAFVLOL-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
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- LVGQIQHJMRUCRM-UHFFFAOYSA-L calcium bisulfite Chemical compound [Ca+2].OS([O-])=O.OS([O-])=O LVGQIQHJMRUCRM-UHFFFAOYSA-L 0.000 description 1
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- BBLSYMNDKUHQAG-UHFFFAOYSA-L dilithium;sulfite Chemical compound [Li+].[Li+].[O-]S([O-])=O BBLSYMNDKUHQAG-UHFFFAOYSA-L 0.000 description 1
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- 238000012851 eutrophication Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- IDNHOWMYUQKKTI-UHFFFAOYSA-M lithium nitrite Chemical compound [Li+].[O-]N=O IDNHOWMYUQKKTI-UHFFFAOYSA-M 0.000 description 1
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- JESHZQPNPCJVNG-UHFFFAOYSA-L magnesium;sulfite Chemical compound [Mg+2].[O-]S([O-])=O JESHZQPNPCJVNG-UHFFFAOYSA-L 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RAFRTSDUWORDLA-UHFFFAOYSA-N phenyl 3-chloropropanoate Chemical compound ClCCC(=O)OC1=CC=CC=C1 RAFRTSDUWORDLA-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
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- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- KAOQVXHBVNKNHA-UHFFFAOYSA-N propyl nitrite Chemical compound CCCON=O KAOQVXHBVNKNHA-UHFFFAOYSA-N 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 238000006257 total synthesis reaction Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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Images
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
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/10—Hydrazines
- C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1815695.0 | 2018-09-26 | ||
| GBGB1815695.0A GB201815695D0 (en) | 2018-09-26 | 2018-09-26 | Synthetic method |
| PCT/GB2019/052718 WO2020065323A1 (en) | 2018-09-26 | 2019-09-26 | Synthetic method for the preparation of a 3-[5-amino-4-(3-cyanobenzoyl)-pyrazol compound |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022502400A JP2022502400A (ja) | 2022-01-11 |
| JP2022502400A5 JP2022502400A5 (https=) | 2022-12-14 |
| JP7291782B2 true JP7291782B2 (ja) | 2023-06-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021516883A Active JP7291782B2 (ja) | 2018-09-26 | 2019-09-26 | 3-[5-アミノ-4-(3-シアノベンゾイル)-ピラゾール化合物の調製のための合成方法 |
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| Country | Link |
|---|---|
| US (1) | US11649213B2 (https=) |
| EP (1) | EP3856721B1 (https=) |
| JP (1) | JP7291782B2 (https=) |
| KR (1) | KR102711257B1 (https=) |
| CN (1) | CN112839928B (https=) |
| AU (1) | AU2019350525B2 (https=) |
| CA (1) | CA3112993A1 (https=) |
| DK (1) | DK3856721T3 (https=) |
| ES (1) | ES2943289T3 (https=) |
| GB (1) | GB201815695D0 (https=) |
| IL (1) | IL281636B2 (https=) |
| WO (1) | WO2020065323A1 (https=) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007521278A (ja) | 2003-06-26 | 2007-08-02 | ノバルティス アクチエンゲゼルシャフト | 5員ヘテロ環を基礎とするp38キナーゼ阻害剤 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1809386A1 (de) | 1968-11-16 | 1970-06-11 | Bayer Ag | Verfahren zur Herstellung von 1,5-disubstituierten 4-Cyanopyrazolen |
| US4686221A (en) * | 1985-10-01 | 1987-08-11 | Kanebo, Ltd. | Quinolinecarboxylic acid compounds and antimicrobial agent containing the same |
| US6005109A (en) * | 1997-10-30 | 1999-12-21 | Pflizer Inc. | Pyrazoles and pyrazolopyrimidines having CRF antagonistic activity |
| US6103900A (en) * | 1992-12-17 | 2000-08-15 | Pfizer Inc | Pyrazoles and pyrazolopyrimidines having CRF antagonistic activity |
| FR2732967B1 (fr) | 1995-04-11 | 1997-07-04 | Sanofi Sa | 1-phenylpyrazole-3-carboxamides substitues, actifs sur la neurotensine, leur preparation, les compositions pharmaceutiques en contenant |
| GB9608435D0 (en) * | 1996-04-24 | 1996-06-26 | Celltech Therapeutics Ltd | Chemical compounds |
| HRP20000724A2 (en) * | 1998-05-05 | 2001-06-30 | Hoffmann La Roche | Pyrazole derivatives as p-38 map kinase inhibitors |
| WO2005007632A1 (en) | 2003-07-18 | 2005-01-27 | Pharmacia Corporation | Substituted pyridazinones as inhibitors of p38 |
| US7485657B2 (en) | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| ATE510836T1 (de) | 2006-01-19 | 2011-06-15 | Matrix Lab Ltd | Umwandlung eines aromatischen diazoniumsalzes in ein arylhydrazin |
| AU2008281594A1 (en) | 2007-08-02 | 2009-02-05 | Generics [Uk] Limited | Novel process |
| WO2009088025A1 (ja) | 2008-01-10 | 2009-07-16 | Hokko Chemical Industry Co., Ltd. | フェニルトリアゾリノン類の製造法 |
| JP5602387B2 (ja) | 2008-05-02 | 2014-10-08 | キヤノン株式会社 | インクジェット用インク、インクジェット記録方法、インクカートリッジ、記録ユニット、及びインクジェット記録装置 |
| CN102964270B (zh) | 2012-11-21 | 2015-01-07 | 合肥星宇化学有限责任公司 | 一种亚硫酸钠还原重氮盐合成肼的方法 |
| WO2018059533A1 (zh) | 2016-09-29 | 2018-04-05 | 南京明德新药研发股份有限公司 | p38αMAPK激酶抑制剂及其制备方法和应用 |
-
2018
- 2018-09-26 GB GBGB1815695.0A patent/GB201815695D0/en not_active Ceased
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2019
- 2019-09-26 CN CN201980063294.3A patent/CN112839928B/zh active Active
- 2019-09-26 WO PCT/GB2019/052718 patent/WO2020065323A1/en not_active Ceased
- 2019-09-26 KR KR1020217008904A patent/KR102711257B1/ko active Active
- 2019-09-26 EP EP19780305.9A patent/EP3856721B1/en active Active
- 2019-09-26 IL IL281636A patent/IL281636B2/en unknown
- 2019-09-26 ES ES19780305T patent/ES2943289T3/es active Active
- 2019-09-26 US US17/279,553 patent/US11649213B2/en active Active
- 2019-09-26 CA CA3112993A patent/CA3112993A1/en active Pending
- 2019-09-26 JP JP2021516883A patent/JP7291782B2/ja active Active
- 2019-09-26 DK DK19780305.9T patent/DK3856721T3/da active
- 2019-09-26 AU AU2019350525A patent/AU2019350525B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007521278A (ja) | 2003-06-26 | 2007-08-02 | ノバルティス アクチエンゲゼルシャフト | 5員ヘテロ環を基礎とするp38キナーゼ阻害剤 |
Non-Patent Citations (1)
| Title |
|---|
| ARKIVOC,2017年,part ii,pp.446-456 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020065323A1 (en) | 2020-04-02 |
| CN112839928B (zh) | 2024-04-30 |
| KR102711257B1 (ko) | 2024-09-30 |
| US20210395207A1 (en) | 2021-12-23 |
| JP2022502400A (ja) | 2022-01-11 |
| EP3856721A1 (en) | 2021-08-04 |
| DK3856721T3 (da) | 2023-04-24 |
| US11649213B2 (en) | 2023-05-16 |
| EP3856721B1 (en) | 2023-03-29 |
| IL281636B2 (en) | 2024-08-01 |
| AU2019350525A1 (en) | 2021-04-15 |
| CN112839928A (zh) | 2021-05-25 |
| AU2019350525B2 (en) | 2024-05-02 |
| IL281636B1 (en) | 2024-04-01 |
| KR20210069044A (ko) | 2021-06-10 |
| IL281636A (en) | 2021-05-31 |
| CA3112993A1 (en) | 2020-04-02 |
| GB201815695D0 (en) | 2018-11-07 |
| ES2943289T3 (es) | 2023-06-12 |
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