JP2019537577A5 - - Google Patents
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- JP2019537577A5 JP2019537577A5 JP2019522385A JP2019522385A JP2019537577A5 JP 2019537577 A5 JP2019537577 A5 JP 2019537577A5 JP 2019522385 A JP2019522385 A JP 2019522385A JP 2019522385 A JP2019522385 A JP 2019522385A JP 2019537577 A5 JP2019537577 A5 JP 2019537577A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazole
- oxazole
- carboxamide
- ethoxycyclohexyl
- pyridin
- 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.)
- Granted
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- -1 heteroaliphatic Chemical group 0.000 claims description 134
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- VAELWSLNTRVXQS-UHFFFAOYSA-N 1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC=N1 VAELWSLNTRVXQS-UHFFFAOYSA-N 0.000 claims description 44
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022175223A JP7379640B2 (ja) | 2016-10-26 | 2022-11-01 | Irak阻害剤としての使用のためのオキサゾール誘導体およびその調製のための方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662413217P | 2016-10-26 | 2016-10-26 | |
| US62/413,217 | 2016-10-26 | ||
| PCT/US2017/058339 WO2018089199A1 (en) | 2016-10-26 | 2017-10-25 | Oxazole derivatives for use as irak inhibitors and method for their preparation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022175223A Division JP7379640B2 (ja) | 2016-10-26 | 2022-11-01 | Irak阻害剤としての使用のためのオキサゾール誘導体およびその調製のための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019537577A JP2019537577A (ja) | 2019-12-26 |
| JP2019537577A5 true JP2019537577A5 (https=) | 2020-12-03 |
| JP7170634B2 JP7170634B2 (ja) | 2022-11-14 |
Family
ID=60302473
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019522385A Active JP7170634B2 (ja) | 2016-10-26 | 2017-10-25 | Irak阻害剤としての使用のためのオキサゾール誘導体およびその調製のための方法 |
| JP2022175223A Active JP7379640B2 (ja) | 2016-10-26 | 2022-11-01 | Irak阻害剤としての使用のためのオキサゾール誘導体およびその調製のための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022175223A Active JP7379640B2 (ja) | 2016-10-26 | 2022-11-01 | Irak阻害剤としての使用のためのオキサゾール誘導体およびその調製のための方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US10370367B2 (https=) |
| EP (1) | EP3532470B1 (https=) |
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| ES (1) | ES2939232T3 (https=) |
| PT (1) | PT3532470T (https=) |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862375B (zh) * | 2018-08-27 | 2022-10-25 | 深圳铂立健医药有限公司 | 吡唑化合物及其药物组合物和应用 |
| BR112022001418A2 (pt) * | 2019-08-08 | 2022-06-07 | Rigel Pharmaceuticals Inc | Compostos e método para tratar a síndrome de liberação de citocinas |
| CN121159524A (zh) * | 2019-08-30 | 2025-12-19 | 里格尔药品股份有限公司 | 吡唑化合物,其配制品以及使用所述化合物和/或配制品的方法 |
| JP2025513716A (ja) * | 2022-03-23 | 2025-04-30 | ライジェル・ファーマシューティカルズ・インコーポレイテッド | Irak阻害剤としてのピリミド-2-イル-ピラゾール化合物 |
| CN121270516A (zh) * | 2024-07-03 | 2026-01-06 | 科辉智药(深圳)新药研究中心有限公司 | 一种irak抑制剂化合物的晶型及其制备方法和应用 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4921475A (en) | 1983-08-18 | 1990-05-01 | Drug Delivery Systems Inc. | Transdermal drug patch with microtubes |
| US5087240A (en) | 1983-08-18 | 1992-02-11 | Drug Delivery Systems Inc. | Transdermal drug patch with conductive fibers |
| US4738851A (en) | 1985-09-27 | 1988-04-19 | University Of Iowa Research Foundation, Inc. | Controlled release ophthalmic gel formulation |
| US5163899A (en) | 1987-03-20 | 1992-11-17 | Drug Delivery Systems Inc. | Transdermal drug delivery system |
| US5312325A (en) | 1987-05-28 | 1994-05-17 | Drug Delivery Systems Inc | Pulsating transdermal drug delivery system |
| GB8804164D0 (en) | 1988-02-23 | 1988-03-23 | Tucker J M | Bandage for administering physiologically active compound |
| US4882150A (en) | 1988-06-03 | 1989-11-21 | Kaufman Herbert E | Drug delivery system |
| US5008110A (en) | 1988-11-10 | 1991-04-16 | The Procter & Gamble Company | Storage-stable transdermal patch |
| US5088977A (en) | 1988-12-21 | 1992-02-18 | Drug Delivery Systems Inc. | Electrical transdermal drug applicator with counteractor and method of drug delivery |
| US5521222A (en) | 1989-09-28 | 1996-05-28 | Alcon Laboratories, Inc. | Topical ophthalmic pharmaceutical vehicles |
| EP0431519B1 (en) | 1989-12-04 | 1994-06-15 | G.D. Searle & Co. | System for transdermal albuterol administration |
| US5077033A (en) | 1990-08-07 | 1991-12-31 | Mediventures Inc. | Ophthalmic drug delivery with thermo-irreversible gels of polxoxyalkylene polymer and ionic polysaccharide |
| ATE141502T1 (de) | 1991-01-15 | 1996-09-15 | Alcon Lab Inc | Verwendung von karrageenan in topischen ophthalmologischen zusammensetzungen |
| US5352456A (en) | 1991-10-10 | 1994-10-04 | Cygnus Therapeutic Systems | Device for administering drug transdermally which provides an initial pulse of drug |
| DE69228827T2 (de) | 1991-12-18 | 1999-10-21 | Minnesota Mining And Mfg. Co., Saint Paul | Mehrschichtige sperrstrukturen |
| EP0553769B1 (de) | 1992-01-29 | 1996-01-03 | FRANZ VÖLKL GmbH & CO. SKI UND TENNIS SPORTARTIKELFABRIK KG | Ballspielschläger, insbesondere Tennisschläger |
| IL114193A (en) | 1994-06-20 | 2000-02-29 | Teva Pharma | Ophthalmic pharmaceutical compositions based on sodium alginate |
| ES2094688B1 (es) | 1994-08-08 | 1997-08-01 | Cusi Lab | Manoemulsion del tipo de aceite en agua, util como vehiculo oftalmico y procedimiento para su preparacion. |
| IT1283911B1 (it) | 1996-02-05 | 1998-05-07 | Farmigea Spa | Soluzioni oftalmiche viscosizzate con polisaccaridi della gomma di tamarindo |
| US5800807A (en) | 1997-01-29 | 1998-09-01 | Bausch & Lomb Incorporated | Ophthalmic compositions including glycerin and propylene glycol |
| US6261547B1 (en) | 1998-04-07 | 2001-07-17 | Alcon Manufacturing, Ltd. | Gelling ophthalmic compositions containing xanthan gum |
| US6197934B1 (en) | 1998-05-22 | 2001-03-06 | Collagenesis, Inc. | Compound delivery using rapidly dissolving collagen film |
| US20100160324A1 (en) | 2004-12-30 | 2010-06-24 | Astex Therapeutics Limited | Pyrazole derivatives as that modulate the activity of cdk, gsk and aurora kinases |
| JP2012254939A (ja) | 2009-10-07 | 2012-12-27 | Astellas Pharma Inc | オキサゾール化合物 |
| CA2964982C (en) | 2014-11-20 | 2022-07-05 | Merck Patent Gmbh | Heteroaryl compounds as irak inhibitors and uses thereof |
| EA039043B1 (ru) * | 2015-04-22 | 2021-11-25 | Райджел Фармасьютикалз, Инк. | Пиразольные соединения и способ получения и применения данных соединений |
| JP2019196309A (ja) * | 2016-09-15 | 2019-11-14 | 武田薬品工業株式会社 | 複素環化合物 |
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2017
- 2017-10-25 CN CN201780080581.6A patent/CN110099899B/zh active Active
- 2017-10-25 PT PT177974953T patent/PT3532470T/pt unknown
- 2017-10-25 US US15/793,770 patent/US10370367B2/en active Active
- 2017-10-25 DK DK17797495.3T patent/DK3532470T3/da active
- 2017-10-25 ES ES17797495T patent/ES2939232T3/es active Active
- 2017-10-25 CA CA3041587A patent/CA3041587A1/en active Pending
- 2017-10-25 WO PCT/US2017/058339 patent/WO2018089199A1/en not_active Ceased
- 2017-10-25 JP JP2019522385A patent/JP7170634B2/ja active Active
- 2017-10-25 EP EP17797495.3A patent/EP3532470B1/en active Active
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- 2022-11-01 JP JP2022175223A patent/JP7379640B2/ja active Active
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