CA2962321A1 - Naphthyridine derivatives as alpha v beta 6 integrin antagonists for the treatment of e.g. fibrotic diseases - Google Patents
Naphthyridine derivatives as alpha v beta 6 integrin antagonists for the treatment of e.g. fibrotic diseases Download PDFInfo
- Publication number
- CA2962321A1 CA2962321A1 CA2962321A CA2962321A CA2962321A1 CA 2962321 A1 CA2962321 A1 CA 2962321A1 CA 2962321 A CA2962321 A CA 2962321A CA 2962321 A CA2962321 A CA 2962321A CA 2962321 A1 CA2962321 A1 CA 2962321A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- pyrazol
- mmol
- pharmaceutically acceptable
- compound
- 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.)
- Abandoned
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 41
- 201000010099 disease Diseases 0.000 title claims description 35
- 238000011282 treatment Methods 0.000 title claims description 31
- 230000003176 fibrotic effect Effects 0.000 title claims description 11
- 239000005557 antagonist Substances 0.000 title description 25
- 108010021309 integrin beta6 Proteins 0.000 title 1
- 150000005054 naphthyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 216
- -1 di-substituted pyrazole Chemical class 0.000 claims abstract description 116
- 150000003839 salts Chemical class 0.000 claims abstract description 89
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 5
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- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
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| PCT/EP2015/071782 WO2016046230A1 (en) | 2014-09-26 | 2015-09-22 | Naphthyridine derivatives as alpha v beta 6 integrin antagonists for the treatment of e.g. fibrotic diseases |
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| KR20180125960A (ko) | 2016-03-15 | 2018-11-26 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 동물 해충을 방제하기 위한 치환된 술포닐 아미드 |
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| CN110167935B (zh) | 2016-11-08 | 2022-05-27 | 百时美施贵宝公司 | 作为αV整合素抑制剂的3-经取代的丙酸 |
| RS61453B1 (sr) * | 2016-11-08 | 2021-03-31 | Bristol Myers Squibb Co | Amidi pirola kao inhibitori alfa v integrina |
| US10851098B2 (en) | 2016-11-08 | 2020-12-01 | Bristol-Myers Squibb Company | Azole amides and amines as alpha v integrin inhibitors |
| BR112019009129A2 (pt) * | 2016-11-08 | 2019-07-16 | Bristol-Myers Squibb Company | compostos mono e espirocíclicos contendo ciclobutano e azetidina como inibidores de alfa v integrina |
| KR102506327B1 (ko) | 2016-11-08 | 2023-03-03 | 브리스톨-마이어스 스큅 컴퍼니 | αV 인테그린 길항제로서의 인다졸 유도체 |
| USRE50554E1 (en) | 2016-12-23 | 2025-08-26 | Pliant Therapeutics, Inc. | Amino acid compounds and methods of use |
| KR102605460B1 (ko) | 2017-02-28 | 2023-11-22 | 모픽 테라퓨틱, 인코포레이티드 | αvβ6 인테그린 억제제 |
| MA52117A (fr) | 2017-02-28 | 2022-04-06 | Morphic Therapeutic Inc | Inhibiteurs de l'intégrine (alpha-v) (bêta-6) |
| US11292802B2 (en) | 2017-11-07 | 2022-04-05 | Bristol-Myers Squibb Company | Substituted tetrahydropyrrolo[1,2-a]pyrazines as alpha v integrin inhibitors |
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| WO2023170680A1 (en) | 2022-03-08 | 2023-09-14 | Equashield Medical Ltd | Fluid transfer station in a robotic pharmaceutical preparation system |
| KR20250120424A (ko) | 2022-12-14 | 2025-08-08 | 알닐람 파마슈티칼스 인코포레이티드 | 간외 전달을 위한 알파-v 베타-6(αvβ6) 인테그린 리간드 |
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| US6932865B2 (en) | 2003-04-11 | 2005-08-23 | Lockheed Martin Corporation | System and method of making single-crystal structures through free-form fabrication techniques |
| PL2139882T3 (pl) | 2007-03-23 | 2014-05-30 | Amgen Inc | 3-podstawione pochodne chinoliny lub chinoksaliny i ich zastosowanie jako inhibitorów 3-kinazy fosfatydyloinozytolu (pi3k) |
| US8563566B2 (en) * | 2007-08-01 | 2013-10-22 | Valeant Pharmaceuticals International | Naphthyridine derivatives as potassium channel modulators |
| EP2211615A4 (en) | 2007-10-22 | 2010-10-13 | Glaxosmithkline Llc | PYRIDOSULFONAMIDE DERIVATIVES AS PI3 KINASE INHIBITORS |
| WO2011111880A1 (ko) | 2010-03-08 | 2011-09-15 | 주식회사 메디젠텍 | 세포핵에서 세포질로의 ｇｓｋ３의 이동을 억제하는 화합물을 함유하는 세포핵에서 세포질로의 gsk3 이동에 의해 발생되는 질환의 치료 또는 예방용 약학적 조성물 |
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| WO2015048819A1 (en) | 2013-09-30 | 2015-04-02 | The Regents Of The University Of California | Anti-alphavbeta1 integrin compounds and methods |
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| WO2016134223A2 (en) | 2015-02-19 | 2016-08-25 | Scifluor Life Sciences, Inc. | Fluorinated tetrahydronaphthyridinyl nonanoic acid derivatives and uses thereof |
| US10214522B2 (en) | 2015-03-10 | 2019-02-26 | The Regents Of The University Of California | Anti-alphavbeta1 integrin inhibitors and methods of use |
| GB201604589D0 (en) | 2016-03-18 | 2016-05-04 | Glaxosmithkline Ip Dev Ltd | Chemical compound |
| GB201604681D0 (en) | 2016-03-21 | 2016-05-04 | Glaxosmithkline Ip Dev Ltd | Chemical Compounds |
| GB201604680D0 (en) | 2016-03-21 | 2016-05-04 | Glaxosmithkline Ip Dev Ltd | Chemical Compounds |
-
2014
- 2014-09-26 GB GBGB1417094.8A patent/GB201417094D0/en not_active Ceased
-
2015
- 2015-09-22 CN CN201580052204.2A patent/CN107074851B/zh not_active Expired - Fee Related
- 2015-09-22 ES ES15767478T patent/ES2811119T3/es active Active
- 2015-09-22 AU AU2015320863A patent/AU2015320863B2/en not_active Ceased
- 2015-09-22 JP JP2017516367A patent/JP6657196B2/ja not_active Expired - Fee Related
- 2015-09-22 RU RU2017114355A patent/RU2692775C2/ru not_active IP Right Cessation
- 2015-09-22 KR KR1020177007736A patent/KR20170053638A/ko not_active Withdrawn
- 2015-09-22 EP EP15767478.9A patent/EP3197894B1/en active Active
- 2015-09-22 US US15/514,416 patent/US10144733B2/en not_active Expired - Fee Related
- 2015-09-22 WO PCT/EP2015/071782 patent/WO2016046230A1/en not_active Ceased
- 2015-09-22 BR BR112017006242A patent/BR112017006242A2/pt not_active Application Discontinuation
- 2015-09-22 CA CA2962321A patent/CA2962321A1/en not_active Abandoned
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2018
- 2018-10-19 US US16/165,506 patent/US10513517B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB201417094D0 (en) | 2014-11-12 |
| RU2017114355A (ru) | 2018-10-29 |
| US20190048005A1 (en) | 2019-02-14 |
| CN107074851B (zh) | 2020-01-10 |
| ES2811119T3 (es) | 2021-03-10 |
| US10144733B2 (en) | 2018-12-04 |
| KR20170053638A (ko) | 2017-05-16 |
| JP6657196B2 (ja) | 2020-03-04 |
| EP3197894B1 (en) | 2020-06-03 |
| BR112017006242A2 (pt) | 2017-12-12 |
| US20170291899A1 (en) | 2017-10-12 |
| AU2015320863B2 (en) | 2018-09-06 |
| RU2692775C2 (ru) | 2019-06-27 |
| US10513517B2 (en) | 2019-12-24 |
| CN107074851A (zh) | 2017-08-18 |
| EP3197894A1 (en) | 2017-08-02 |
| JP2017528504A (ja) | 2017-09-28 |
| AU2015320863A1 (en) | 2017-03-09 |
| RU2017114355A3 (cg-RX-API-DMAC7.html) | 2019-01-14 |
| WO2016046230A1 (en) | 2016-03-31 |
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