CA3085761A1 - Triazole n-linked carbamoylcyclohexyl acids as lpa antagonists - Google Patents
Triazole n-linked carbamoylcyclohexyl acids as lpa antagonists Download PDFInfo
- Publication number
- CA3085761A1 CA3085761A1 CA3085761A CA3085761A CA3085761A1 CA 3085761 A1 CA3085761 A1 CA 3085761A1 CA 3085761 A CA3085761 A CA 3085761A CA 3085761 A CA3085761 A CA 3085761A CA 3085761 A1 CA3085761 A1 CA 3085761A1
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- CA
- Canada
- Prior art keywords
- pyridin
- pyrrolo
- triazolo
- isopropy1
- fluoro
- 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.)
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- -1 carbamoylcyclohexyl acids Chemical class 0.000 title claims description 623
- 239000002253 acid Substances 0.000 title description 2
- 239000005557 antagonist Substances 0.000 title 1
- 150000003852 triazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 188
- 150000003839 salts Chemical class 0.000 claims abstract description 49
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 561
- 125000000217 alkyl group Chemical group 0.000 claims description 231
- 125000003386 piperidinyl group Chemical group 0.000 claims description 201
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 173
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 163
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 162
- 229910052757 nitrogen Inorganic materials 0.000 claims description 152
- 125000002757 morpholinyl group Chemical group 0.000 claims description 146
- 125000004076 pyridyl group Chemical group 0.000 claims description 146
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 136
- 125000004193 piperazinyl group Chemical group 0.000 claims description 133
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 132
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 129
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 124
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 120
- 201000006417 multiple sclerosis Diseases 0.000 claims description 111
- 125000001424 substituent group Chemical group 0.000 claims description 96
- 125000002393 azetidinyl group Chemical group 0.000 claims description 91
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 71
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 68
- 125000003566 oxetanyl group Chemical group 0.000 claims description 68
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 67
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 65
- 229910052801 chlorine Inorganic materials 0.000 claims description 63
- 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 61
- 125000005959 diazepanyl group Chemical group 0.000 claims description 60
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 57
- 229910052731 fluorine Inorganic materials 0.000 claims description 57
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 55
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 49
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 125000002883 imidazolyl group Chemical group 0.000 claims description 40
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 39
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 38
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 35
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 29
- VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims description 28
- 125000001425 triazolyl group Chemical group 0.000 claims description 27
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
- 125000003725 azepanyl group Chemical group 0.000 claims description 25
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
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- 125000004122 cyclic group Chemical group 0.000 claims description 19
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
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- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 12
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- 125000001041 indolyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 10
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
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- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 7
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
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- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000009772 tissue formation Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 230000010472 type I IFN response Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/04—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
- A61K31/435—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
- A61K31/437—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 five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762607507P | 2017-12-19 | 2017-12-19 | |
| US62/607,507 | 2017-12-19 | ||
| PCT/US2018/066107 WO2019126082A1 (en) | 2017-12-19 | 2018-12-18 | 6-azaindole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3085761A1 true CA3085761A1 (en) | 2019-06-27 |
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| EP (1) | EP3728253B1 (enExample) |
| JP (1) | JP7304352B2 (enExample) |
| KR (1) | KR102742181B1 (enExample) |
| CN (1) | CN111699185B (enExample) |
| AU (1) | AU2018390543A1 (enExample) |
| BR (1) | BR112020011788A2 (enExample) |
| CA (1) | CA3085761A1 (enExample) |
| EA (1) | EA202091508A1 (enExample) |
| ES (1) | ES2977657T3 (enExample) |
| IL (1) | IL275365A (enExample) |
| MX (1) | MX2020005873A (enExample) |
| SG (1) | SG11202005704RA (enExample) |
| WO (1) | WO2019126082A1 (enExample) |
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| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| BR112020011984A2 (pt) * | 2017-12-20 | 2020-11-17 | Bristol-Myers Squibb Company | compostos de amino indol úteis como inibidores de tlr |
| BR112020012002A2 (pt) * | 2017-12-20 | 2020-11-17 | Bristol-Myers Squibb Company | compostos diazaindol |
| ES2965182T3 (es) * | 2017-12-20 | 2024-04-11 | Bristol Myers Squibb Co | Compuestos de indol sustituidos con arilo y heteroarilo |
| EP3752505B1 (en) | 2018-02-12 | 2023-01-11 | F. Hoffmann-La Roche AG | Novel sulfone compounds and derivatives for the treatment and prophylaxis of virus infection |
| SG11202011137SA (en) | 2018-06-05 | 2020-12-30 | Hoffmann La Roche | Tetrahydro-1 h-pyrazino[2,1 -ajisoindolylquinoline compounds for the treatment of autoimmune disease |
| JP7434186B2 (ja) | 2018-06-12 | 2024-02-20 | エフ． ホフマン－ラ ロシュ アーゲー | 自己免疫疾患の処置のための新規のヘテロアリールヘテロシクリル化合物 |
| CN112584903B (zh) | 2018-07-23 | 2025-12-23 | 豪夫迈·罗氏有限公司 | 用于自身免疫性疾病治疗的哌嗪化合物 |
| CN112638908A (zh) | 2018-09-04 | 2021-04-09 | 豪夫迈·罗氏有限公司 | 用于治疗自身免疫性疾病的苯并噻唑类化合物 |
| CN112654618A (zh) | 2018-09-06 | 2021-04-13 | 豪夫迈·罗氏有限公司 | 用于治疗自身免疫性疾病的新型环脒化合物 |
| WO2020048596A1 (en) | 2018-09-06 | 2020-03-12 | F. Hoffmann-La Roche Ag | Novel pyrazolopyridine compounds for the treatment of autoimmune disease |
| GB201913752D0 (en) | 2019-09-24 | 2019-11-06 | Syngenta Crop Protection Ag | Herbicidal compounds |
| GB201914277D0 (en) | 2019-10-03 | 2019-11-20 | Syngenta Crop Protection Ag | Herbicidal compounds |
| EP4051387B1 (en) | 2019-10-31 | 2025-02-19 | F. Hoffmann-La Roche AG | Hydropyrazino[1,2-d][1,4]diazepine compounds for the treatment of autoimmune disease |
| WO2021099284A1 (en) | 2019-11-19 | 2021-05-27 | F. Hoffmann-La Roche Ag | Hydro-1h-pyrrolo[1,2-a]pyrazine compounds for the treatment of autoimmune disease |
| US12421252B2 (en) | 2019-11-20 | 2025-09-23 | Hoffmann-La Roche Inc. | Spiro (isobenzofuranazetidine) compounds for the treatment of autoimmune disease |
| GB201917898D0 (en) | 2019-12-06 | 2020-01-22 | Syngenta Crop Protection Ag | Herbicidal compounds |
| JP7462772B2 (ja) | 2020-08-13 | 2024-04-05 | エルジー エナジー ソリューション リミテッド | 改善された電極リード接続構造を有するバッテリーモジュール、それを含むバッテリーパック及び自動車 |
| CA3189873A1 (en) | 2020-08-19 | 2022-02-24 | David S. Yoon | 1h-benzo[d]imidazole derivatives as tlr9 inhibitors for the treatment of fibrosis |
| IL300696A (en) * | 2020-08-19 | 2023-04-01 | Bristol Myers Squibb Co | ALTERNATIVE HETEROARYL COMPOUNDS ARE USEFUL AS TLR9 INHIBITORS |
| KR20230053644A (ko) | 2020-08-19 | 2023-04-21 | 브리스톨-마이어스 스큅 컴퍼니 | 섬유증의 치료를 위한 tlr9 억제제로서의 이미다조[1,2-a]피리딘 및 [1,2,4]트리아졸로[1,5-a]피리딘 유도체 |
| JP2023538608A (ja) * | 2020-08-19 | 2023-09-08 | ブリストル－マイヤーズ スクイブ カンパニー | 線維症の処置のためのｔｌｒ９阻害剤阻害剤としての１ｈ－ピロロ［３，２－ｃ］ピリジンおよび１ｈ－ピロロ［２，３－ｃ］ピリジン誘導体 |
| KR20230104781A (ko) | 2020-10-05 | 2023-07-10 | 인라이븐 테라퓨틱스, 인크. | Bcr-abl 티로신 키나아제의 억제를 위한 5- 및 6-아자인돌 화합물 |
| CN116783202A (zh) * | 2021-02-09 | 2023-09-19 | 吉利德科学公司 | 噻吩并吡咯化合物 |
| TWI861488B (zh) | 2021-04-16 | 2024-11-11 | 美商基利科學股份有限公司 | 噻吩并吡咯化合物 |
| AU2022341114A1 (en) | 2021-09-10 | 2024-02-29 | Gilead Sciences, Inc. | Thienopyrrole compounds |
| CN114591339B (zh) * | 2022-05-10 | 2022-08-02 | 上海维申医药有限公司 | 一类Toll样受体抑制剂及其制备和应用 |
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| US5468757A (en) * | 1994-01-31 | 1995-11-21 | Eli Lilly And Company | 6-azaindole thromboxane synthase inhibitors |
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| BR0014843A (pt) | 1999-10-19 | 2002-06-11 | Merck & Co Inc | Composto, composição farmacêutica, métodos para tratar ou prevenir o câncer em um mamìfero, uma doença em que a angiogênese está implicada, a vascularização retinal, a retinipatia diabética, a degeneração macular relacionada com a idade, doença inflamatória, uma doença ou condição dependente de tirosina quinase e, patologias relacionadas com o osso, processo para fabricar uma composição farmacêutica, e, método para reduzir ou impedir o dano de tecido que segue um evento isquêmico |
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| US20090099179A1 (en) | 2006-04-04 | 2009-04-16 | Myriad Genetics, Incorporated | Compounds for diseases and disorders |
| DE102006033109A1 (de) | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
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| FR2930249B1 (fr) | 2008-04-21 | 2010-05-14 | Sanofi Aventis | Nouveaux derives de 3-aminoalkyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique. |
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| TR201809739T4 (tr) | 2009-07-16 | 2018-07-23 | Mallinckrodt Llc | Toll benzeri reseptör 9 antagonistleri olarak (+)-morfinanlar ve bunların terapötik amaçlı kullanımları. |
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| DE102011111400A1 (de) * | 2011-08-23 | 2013-02-28 | Merck Patent Gmbh | Bicyclische heteroaromatische Verbindungen |
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| EP3080124A1 (en) | 2013-12-13 | 2016-10-19 | Takeda Pharmaceutical Company Limited | Pyrrolo[3,2-c]pyridine derivatives as tlr inhibitors |
| BR112017002811B1 (pt) * | 2014-08-15 | 2022-09-06 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Compostos de pirrolopirimidina usados como agonista de tlr7 e seu uso, composição farmacêutica e kit |
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| US10071079B2 (en) * | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| AU2017307208B2 (en) | 2016-07-30 | 2021-01-21 | Bristol-Myers Squibb Company | Dimethoxyphenyl substituted indole compounds as TLR7, TLR8 or TLR9 inhibitors |
| EP3510024B1 (en) | 2016-09-09 | 2021-11-17 | Bristol-Myers Squibb Company | Pyridyl substituted indole compounds |
| WO2019126113A1 (en) * | 2017-12-19 | 2019-06-27 | Bristol-Myers Squibb Company | Substituted indole compounds useful as tlr inhibitors |
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- 2018-12-18 MX MX2020005873A patent/MX2020005873A/es unknown
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- 2018-12-18 BR BR112020011788-9A patent/BR112020011788A2/pt not_active Application Discontinuation
- 2018-12-18 KR KR1020207020877A patent/KR102742181B1/ko active Active
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- 2018-12-18 SG SG11202005704RA patent/SG11202005704RA/en unknown
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2020
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2022
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| SG11202005704RA (en) | 2020-07-29 |
| KR20200101956A (ko) | 2020-08-28 |
| IL275365A (en) | 2020-07-30 |
| JP7304352B2 (ja) | 2023-07-06 |
| AU2018390543A1 (en) | 2020-08-06 |
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| US20200385382A1 (en) | 2020-12-10 |
| WO2019126082A1 (en) | 2019-06-27 |
| US20220348576A1 (en) | 2022-11-03 |
| CN111699185A (zh) | 2020-09-22 |
| US11912703B2 (en) | 2024-02-27 |
| MX2020005873A (es) | 2020-08-13 |
| US11427580B2 (en) | 2022-08-30 |
| EA202091508A1 (ru) | 2020-09-14 |
| CN111699185B (zh) | 2023-06-27 |
| ES2977657T3 (es) | 2024-08-28 |
| KR102742181B1 (ko) | 2024-12-11 |
| EP3728253A1 (en) | 2020-10-28 |
| BR112020011788A2 (pt) | 2020-11-24 |
| JP2021507912A (ja) | 2021-02-25 |
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