RU2015156142A - Бисульфат ингибитора янус-киназы (jak) и способ его получения - Google Patents
Бисульфат ингибитора янус-киназы (jak) и способ его получения Download PDFInfo
- Publication number
- RU2015156142A RU2015156142A RU2015156142A RU2015156142A RU2015156142A RU 2015156142 A RU2015156142 A RU 2015156142A RU 2015156142 A RU2015156142 A RU 2015156142A RU 2015156142 A RU2015156142 A RU 2015156142A RU 2015156142 A RU2015156142 A RU 2015156142A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- bisulfate
- hexahydrocyclopenta
- thiadiazol
- pyrrolo
- Prior art date
Links
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 229940122245 Janus kinase inhibitor Drugs 0.000 title 1
- -1 3-methoxy-1,2,4-thiadiazol-5-yl Chemical group 0.000 claims 5
- ODYDEDBPRBMSKE-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrole-2-carboxamide Chemical compound C1CCC2CN(C(=O)N)CC21 ODYDEDBPRBMSKE-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000005755 formation reaction Methods 0.000 claims 2
- 239000012046 mixed solvent Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (10)
1. Бисульфат (3aR,5s,6aS)-N-(3-метоксил-1,2,4-тиадиазол-5-ил)-5-(метил(7Н-пирроло[2,3-d]пиримидин-4-ил)амино)гексагидроциклопента[с]пиррол-2(1Н)-карбоксамида формулы (I),
2. Бисульфат (3aR,5s,6aS)-N-(3-метоксил-1,2,4-тиадиазол-5-ил)-5-(метил(7Н-пирроло[2,3-d]пиримидин-4-ил)амино)гексагидроциклопента[с]пиррол-2(1Н)-карбоксамида формулы (I) по п. 1, где стехиометрическое отношение соединения формулы (IV) к серной кислоте составляет 1:1,
3. Способ получения бисульфата (3aR,5s,6aS)-N-(3-метоксил-1,2,4-тиадиазол-5-ил)-5-(метил(7Н-пирроло[2,3-d]пиримидин-4-ил)амино)гексагидроциклопента[с]пиррол-2(1Н)-карбоксамида формулы (I) по п. 1, включающий стадию реакции образования соли соединения формулы (IV) и серной кислоты,
4. Способ получения по п. 3, где реакцию образования соли проводят в растворителе, а растворитель представляет собой смешанный растворитель из галогеналканов и спиртов, имеющих количество атомов углерода, меньшее или равное 3, предпочтительно смешанный растворитель из дихлорметана и метанола.
5. Способ получения по п. 4, где температура реакции при реакции образования соли составляет от 10 до 30°C, а время реакции предпочтительно составляет от 0,5 до 4 часов.
6. Фармацевтическая композиция, содержащая бисульфат (3aR,5s,6aS)-N-(3-метоксил-1,2,4-тиадиазол-5-ил)-5-(метил(7Н-пирроло[2,3-d]пиримидин-4-ил)амино)гексагидроциклопента[с]пиррол-2(1Н)-карбоксамида формулы (I) по п. 1 и фармацевтически приемлемый носитель.
7. Применение бисульфата (3aR,5s,6aS)-N-(3-метоксил-1,2,4-тиадиазол-5-ил)-5-(метил(7Н-пирроло[2,3-d]пиримидин-4-ил)амино)гексагидроциклопента[с]пиррол-2(1Н)-карбоксамида формулы (I) по п. 1 или фармацевтической композиции по п. 6 при получении лекарственного средства для лечения ревматизма и ревматоидного артрита.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310227683.X | 2013-06-07 | ||
| CN201310227683 | 2013-06-07 | ||
| PCT/CN2014/076794 WO2014194741A1 (zh) | 2013-06-07 | 2014-05-05 | 一种jak激酶抑制剂的硫酸氢盐及其制备方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2015156142A true RU2015156142A (ru) | 2017-07-17 |
| RU2015156142A3 RU2015156142A3 (ru) | 2018-03-19 |
| RU2665680C2 RU2665680C2 (ru) | 2018-09-04 |
Family
ID=52007520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015156142A RU2665680C2 (ru) | 2013-06-07 | 2014-05-05 | Бисульфат ингибитора янус-киназы (jak) и способ его получения |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9422300B2 (ru) |
| EP (1) | EP3006445B1 (ru) |
| JP (1) | JP6323885B2 (ru) |
| KR (1) | KR102275326B1 (ru) |
| CN (1) | CN104470927B (ru) |
| AU (1) | AU2014277506B2 (ru) |
| BR (1) | BR112015029463B1 (ru) |
| CA (1) | CA2913194C (ru) |
| ES (1) | ES2655074T3 (ru) |
| HK (1) | HK1206026A1 (ru) |
| HU (1) | HUE036533T2 (ru) |
| MX (1) | MX2015016513A (ru) |
| PT (1) | PT3006445T (ru) |
| RU (1) | RU2665680C2 (ru) |
| TW (1) | TWI641609B (ru) |
| WO (1) | WO2014194741A1 (ru) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566327A (zh) * | 2014-10-09 | 2016-05-11 | 江苏恒瑞医药股份有限公司 | 一种jak激酶抑制剂的硫酸氢盐的i型结晶及其制备方法 |
| KR102522895B1 (ko) * | 2014-11-05 | 2023-04-17 | 지앙수 헨그루이 파마슈티컬스 컴퍼니 리미티드 | Jak 키나아제 억제제 바이설페이트의 결정형 및 이의 제조방법 |
| WO2017140254A1 (zh) | 2016-02-19 | 2017-08-24 | 江苏恒瑞医药股份有限公司 | 一种含有jak激酶抑制剂或其可药用盐的药物组合物 |
| CA3040981A1 (en) | 2016-11-23 | 2018-05-31 | Bing Liu | Preparation method for and intermediate of pyrrolo six-membered heteroaromatic ring derivative |
| TW201827436A (zh) * | 2017-01-20 | 2018-08-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 一種ｊａｋ激酶抑制劑的硫酸氫鹽的晶型及其製備方法 |
| US11241378B2 (en) | 2017-11-20 | 2022-02-08 | Jiangsu Hengrui Medicine Co., Ltd. | Pharmaceutical JAK kinase inhibitor and diethylene glycol composition for topical administration and preparation method therefor |
| CA3118488A1 (en) * | 2018-11-05 | 2020-05-14 | Avista Pharma Solutions, Inc. | Chemical compounds |
| CN111205290B (zh) * | 2018-11-22 | 2021-10-08 | 江苏恒瑞医药股份有限公司 | 一种jak激酶抑制剂的结晶形式及其制备方法 |
| CN111440127B (zh) * | 2019-01-17 | 2022-07-26 | 青岛农业大学 | 一种噻唑酰胺类化合物及其制备和应用 |
| WO2021043850A1 (en) * | 2019-09-05 | 2021-03-11 | Universität Bern | Tricyclic janus kinase (jak) inhibitors and their use in the treatment of autoimmune diseases |
| CN113698404B (zh) * | 2020-05-21 | 2023-06-16 | 江苏恒瑞医药股份有限公司 | 一种低溶剂残留的六氢环戊并[c]吡咯-2(1H)-甲酰胺化合物及其制备方法 |
| IL300006A (en) | 2020-07-28 | 2023-03-01 | Arcutis Biotherapeutics Inc | A formulation for external use containing a JAK inhibitor and Orat-4 |
| JP2023550363A (ja) | 2020-11-17 | 2023-12-01 | アーキュティス・バイオセラピューティクス・インコーポレーテッド | 深部皮膚薬物送達のための組成物および方法 |
| CN112457272B (zh) * | 2020-12-02 | 2022-04-19 | 上海再启生物技术有限公司 | (3-甲氧基-1,2,4-噻二唑-5-氨基)甲酸苯酯的制备方法 |
| WO2023114832A1 (en) | 2021-12-15 | 2023-06-22 | Arcutis Biotherapeutics, Inc. | Stable formulations of shr0302 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DZ3359A1 (fr) * | 2000-06-26 | 2002-01-03 | Pfizer Prod Inc | DÉRIVÉS DE PYRROLO [2,3-d] PYRIMIDINE UTILES COMME AGENTS IMMUNOSUPPRESSEURS |
| GB0307856D0 (en) | 2003-04-04 | 2003-05-14 | Novartis Ag | Organic compounds |
| US7745462B2 (en) * | 2003-04-04 | 2010-06-29 | Novartis Ag | Quinoline-2-one derivatives for the treatment of airways diseases |
| RU2434871C2 (ru) * | 2005-02-03 | 2011-11-27 | Вертекс Фармасьютикалз Инкорпорейтед | Пирролопиримидины, применимые в качестве ингибиторов протеинкиназы |
| AU2011213198B2 (en) * | 2010-02-05 | 2014-04-24 | Zoetis Llc | Pyrrolo [ 2,3-d] pyrimidine urea compounds as JAK inhibitors |
| EP2721025B1 (en) * | 2011-06-16 | 2015-11-25 | Boehringer Ingelheim International Gmbh | New selective ccr2 antagonists |
| SI2796460T1 (sl) * | 2011-12-21 | 2018-10-30 | Jiangsu Hengrui Medicine Co. Ltd | Pirolni šestčlenski derivat heteroarilnega obroča, postopek priprave zanj in medicinske uporabe le-tega |
-
2014
- 2014-05-05 JP JP2016517135A patent/JP6323885B2/ja active Active
- 2014-05-05 CA CA2913194A patent/CA2913194C/en active Active
- 2014-05-05 MX MX2015016513A patent/MX2015016513A/es active IP Right Grant
- 2014-05-05 AU AU2014277506A patent/AU2014277506B2/en active Active
- 2014-05-05 US US14/895,117 patent/US9422300B2/en active Active
- 2014-05-05 EP EP14807030.3A patent/EP3006445B1/en active Active
- 2014-05-05 CN CN201480001854.XA patent/CN104470927B/zh active Active
- 2014-05-05 WO PCT/CN2014/076794 patent/WO2014194741A1/zh active Application Filing
- 2014-05-05 RU RU2015156142A patent/RU2665680C2/ru active
- 2014-05-05 HU HUE14807030A patent/HUE036533T2/hu unknown
- 2014-05-05 ES ES14807030.3T patent/ES2655074T3/es active Active
- 2014-05-05 PT PT148070303T patent/PT3006445T/pt unknown
- 2014-05-05 BR BR112015029463-4A patent/BR112015029463B1/pt active IP Right Grant
- 2014-05-05 KR KR1020157035615A patent/KR102275326B1/ko active IP Right Grant
- 2014-05-14 TW TW103116955A patent/TWI641609B/zh active
-
2015
- 2015-07-13 HK HK15106673.4A patent/HK1206026A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT3006445T (pt) | 2018-01-09 |
| RU2015156142A3 (ru) | 2018-03-19 |
| KR20160032021A (ko) | 2016-03-23 |
| WO2014194741A1 (zh) | 2014-12-11 |
| TWI641609B (zh) | 2018-11-21 |
| EP3006445B1 (en) | 2017-11-15 |
| BR112015029463B1 (pt) | 2023-01-10 |
| AU2014277506A1 (en) | 2016-01-21 |
| JP2016520134A (ja) | 2016-07-11 |
| MX2015016513A (es) | 2016-04-15 |
| JP6323885B2 (ja) | 2018-05-16 |
| KR102275326B1 (ko) | 2021-07-12 |
| ES2655074T3 (es) | 2018-02-16 |
| EP3006445A4 (en) | 2016-11-23 |
| RU2665680C2 (ru) | 2018-09-04 |
| US20160102098A1 (en) | 2016-04-14 |
| CA2913194A1 (en) | 2014-12-11 |
| HUE036533T2 (hu) | 2018-07-30 |
| US9422300B2 (en) | 2016-08-23 |
| TW201514180A (zh) | 2015-04-16 |
| CN104470927A (zh) | 2015-03-25 |
| AU2014277506B2 (en) | 2017-08-31 |
| BR112015029463A2 (pt) | 2017-07-25 |
| CA2913194C (en) | 2021-03-02 |
| EP3006445A1 (en) | 2016-04-13 |
| HK1206026A1 (zh) | 2015-12-31 |
| CN104470927B (zh) | 2016-05-04 |
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