TW202016111A - 用於治療自體免疫疾病之新穎四氫-1H-吡并[2,1-a]異吲哚基喹啉化合物 - Google Patents
用於治療自體免疫疾病之新穎四氫-1H-吡并[2,1-a]異吲哚基喹啉化合物 Download PDFInfo
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- TW202016111A TW202016111A TW108119369A TW108119369A TW202016111A TW 202016111 A TW202016111 A TW 202016111A TW 108119369 A TW108119369 A TW 108119369A TW 108119369 A TW108119369 A TW 108119369A TW 202016111 A TW202016111 A TW 202016111A
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- Prior art keywords
- methyl
- tetrahydro
- carbonitrile
- amino
- isoindol
- Prior art date
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- 208000023275 Autoimmune disease Diseases 0.000 title description 3
- ZDBNKQXDFFQZGN-UHFFFAOYSA-N 1-quinolin-2-yl-1,2,3,4,6,10b-hexahydropyrazino[2,1-a]isoindole Chemical class C1(NCCN2C1C1=CC=CC=C1C2)C1=NC2=CC=CC=C2C=C1 ZDBNKQXDFFQZGN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 328
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 28
- -1 1,4-diazacycloheptanyl Chemical group 0.000 claims description 395
- CIIFKVFOVFJZDM-UHFFFAOYSA-N quinoline-8-carbonitrile Chemical compound C1=CN=C2C(C#N)=CC=CC2=C1 CIIFKVFOVFJZDM-UHFFFAOYSA-N 0.000 claims description 345
- 125000000217 alkyl group Chemical group 0.000 claims description 187
- 238000002360 preparation method Methods 0.000 claims description 172
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 102
- 125000003545 alkoxy group Chemical group 0.000 claims description 68
- 150000001412 amines Chemical class 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- KIDIJBYYGAEULX-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-7-carbonitrile Chemical compound N#CC1=CC=CC2=CC=NN12 KIDIJBYYGAEULX-UHFFFAOYSA-N 0.000 claims description 54
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 54
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 34
- 229910052805 deuterium Inorganic materials 0.000 claims description 31
- 125000003277 amino group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 102000008235 Toll-Like Receptor 9 Human genes 0.000 claims description 28
- 108010060818 Toll-Like Receptor 9 Proteins 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 27
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 claims description 25
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims description 25
- 102100033110 Toll-like receptor 8 Human genes 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 20
- 239000002585 base Substances 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 19
- 241000009298 Trigla lyra Species 0.000 claims description 18
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 16
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 16
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 15
- 150000004820 halides Chemical class 0.000 claims description 15
- 125000003386 piperidinyl group Chemical group 0.000 claims description 14
- 239000005557 antagonist Substances 0.000 claims description 13
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 12
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- MXFYYFVVIIWKFE-UHFFFAOYSA-N dicyclohexyl-[2-[2,6-di(propan-2-yloxy)phenyl]phenyl]phosphane Chemical group CC(C)OC1=CC=CC(OC(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 MXFYYFVVIIWKFE-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 208000005777 Lupus Nephritis Diseases 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 150000003973 alkyl amines Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000005576 amination reaction Methods 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- JPPREFOETTUXDK-UHFFFAOYSA-N 1h-1,3-diazepine Chemical group N1C=CC=CN=C1 JPPREFOETTUXDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 3
- UQPXYEYBUROSJF-UHFFFAOYSA-N 1,6-diazaspiro[3.3]heptane Chemical compound N1CCC11CNC1 UQPXYEYBUROSJF-UHFFFAOYSA-N 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- PFJOTFSIBVZGPK-UHFFFAOYSA-N 1-ethyl-2-methylhydrazine Chemical compound CCNNC PFJOTFSIBVZGPK-UHFFFAOYSA-N 0.000 claims description 2
- UXFJONFKCHAVRY-UHFFFAOYSA-N 1-hydroxy-1,4-diazepane Chemical compound ON1CCCNCC1 UXFJONFKCHAVRY-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5386—1,4-Oxazines, e.g. morpholine spiro-condensed or forming part of bridged ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- 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
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- 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
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- 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
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- 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
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D498/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US12503471B2 (en) | 2019-11-19 | 2025-12-23 | Hoffmann-La Roche Inc. | Triazatricycle compounds for the treatment of autoimmune disease |
| JP2023502087A (ja) | 2019-11-19 | 2023-01-20 | 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ヒドロ－１Ｈ－ピロロ［１，２－ａ］ピラジン化合物 |
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| TW202214632A (zh) * | 2020-07-27 | 2022-04-16 | 大陸商江蘇恆瑞醫藥股份有限公司 | 吲哚稠環類衍生物、其製備方法及其在醫藥上的應用 |
| CN114057759B (zh) * | 2020-08-07 | 2023-05-16 | 江苏恒瑞医药股份有限公司 | 稠合四环类衍生物、其制备方法及其在医药上的应用 |
| CN116490506B (zh) * | 2020-11-26 | 2024-12-13 | 江苏恒瑞医药股份有限公司 | 稠合三环化合物、其制备方法及其在医药上的应用 |
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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 |
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| KR102519535B1 (ko) | 2016-09-09 | 2023-04-06 | 브리스톨-마이어스 스큅 컴퍼니 | 피리딜 치환된 인돌 화합물 |
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| CN110997656B (zh) | 2017-08-04 | 2023-04-14 | 百时美施贵宝公司 | 用作tlr7/8/9抑制剂的取代的吲哚化合物 |
| FI3692040T3 (fi) | 2017-10-05 | 2023-03-29 | Glaxosmithkline Ip Dev Ltd | Kemiallisia yhdisteitä |
| CN111448190B (zh) | 2017-11-14 | 2023-09-26 | 百时美施贵宝公司 | 取代的吲哚化合物 |
| BR112020011668A2 (pt) | 2017-12-15 | 2020-11-17 | Bristol-Myers Squibb Company | compostos de éter de indol substituído |
| FI3728252T3 (fi) | 2017-12-18 | 2023-10-18 | Bristol Myers Squibb Co | 4-atsaindoliyhdisteitä |
| WO2019126082A1 (en) | 2017-12-19 | 2019-06-27 | Bristol-Myers Squibb Company | 6-azaindole compounds |
| CN111511729A (zh) | 2017-12-19 | 2020-08-07 | 默克专利股份公司 | Tlr7/8拮抗剂及其用途 |
| JP7313354B2 (ja) | 2017-12-19 | 2023-07-24 | ブリストル－マイヤーズ スクイブ カンパニー | Ｔｌｒ阻害剤として有用なアミド置換されたインドール化合物 |
| BR112020012084A2 (pt) | 2017-12-19 | 2020-11-24 | Bristol-Myers Squibb Company | compostos de indol substituído úteis como inibidores de tlr |
| US11299501B2 (en) | 2017-12-20 | 2022-04-12 | Bristol-Myers Squibb Company | Diazaindole compounds |
| BR112020011984A2 (pt) | 2017-12-20 | 2020-11-17 | Bristol-Myers Squibb Company | compostos de amino indol úteis como inibidores de tlr |
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| JP2021507889A (ja) | 2017-12-22 | 2021-02-25 | ノバルティス アーゲー | ピラゾロピペリジン誘導体の新規な使用 |
| JP7407740B2 (ja) | 2018-05-18 | 2024-01-04 | ノバルティス アーゲー | Ｔｌｒ７／ｔｌｒ８阻害剤の結晶形態 |
| WO2019236710A1 (en) | 2018-06-05 | 2019-12-12 | Praxis Biotech LLC | Inhibitors of integrated stress response pathway |
| TWI825144B (zh) | 2018-08-10 | 2023-12-11 | 美商思達利醫藥公司 | 第二型轉麩醯胺酸酶(tg2)抑制劑 |
| WO2021094301A1 (en) | 2019-11-12 | 2021-05-20 | F. Hoffmann-La Roche Ag | Hydropyrazino[1,2-b]isoquinoline compounds for the treatment of autoimmune disease |
| US12503471B2 (en) | 2019-11-19 | 2025-12-23 | Hoffmann-La Roche Inc. | Triazatricycle compounds for the treatment of autoimmune disease |
| BR112022009856A2 (pt) | 2019-11-26 | 2022-08-02 | Hoffmann La Roche | Compostos de 1,8-naftiridin-2-ona para o tratamento de doença autoimune |
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2019
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- 2019-06-03 JP JP2020567772A patent/JP7374130B2/ja active Active
- 2019-06-03 US US16/972,556 patent/US12157746B2/en active Active
- 2019-06-03 PE PE2020001875A patent/PE20210131A1/es unknown
- 2019-06-03 BR BR112020024782-0A patent/BR112020024782A2/pt not_active Application Discontinuation
- 2019-06-03 SG SG11202011137SA patent/SG11202011137SA/en unknown
- 2019-06-03 CA CA3098291A patent/CA3098291A1/en active Pending
- 2019-06-03 EP EP19729220.4A patent/EP3802539B1/en active Active
- 2019-06-03 WO PCT/EP2019/064323 patent/WO2019233941A1/en not_active Ceased
- 2019-06-03 CR CR20200584A patent/CR20200584A/es unknown
- 2019-06-03 AU AU2019280728A patent/AU2019280728A1/en not_active Abandoned
- 2019-06-03 CN CN201980035182.7A patent/CN112204028B/zh active Active
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- 2019-06-03 MA MA052747A patent/MA52747A/fr unknown
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2020
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- 2020-12-01 IL IL279144A patent/IL279144A/en unknown
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| CA3098291A1 (en) | 2019-12-12 |
| CO2020014677A2 (es) | 2020-12-10 |
| AU2019280728A1 (en) | 2020-11-12 |
| BR112020024782A2 (pt) | 2021-03-02 |
| CL2020003065A1 (es) | 2021-04-30 |
| EP3802539C0 (en) | 2023-09-20 |
| WO2019233941A1 (en) | 2019-12-12 |
| KR20210018818A (ko) | 2021-02-18 |
| CN112204028A (zh) | 2021-01-08 |
| EP3802539A1 (en) | 2021-04-14 |
| IL279144A (en) | 2021-01-31 |
| MA52747A (fr) | 2021-04-14 |
| EP3802539B1 (en) | 2023-09-20 |
| MX2020012827A (es) | 2021-02-15 |
| CR20200584A (es) | 2021-01-18 |
| PH12020552092A1 (en) | 2021-05-31 |
| CN112204028B (zh) | 2023-12-29 |
| JP2021527041A (ja) | 2021-10-11 |
| SG11202011137SA (en) | 2020-12-30 |
| JP7374130B2 (ja) | 2023-11-06 |
| PE20210131A1 (es) | 2021-01-19 |
| US20210371432A1 (en) | 2021-12-02 |
| US12157746B2 (en) | 2024-12-03 |
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