CA3085937A1 - Diazaindole compounds - Google Patents
Diazaindole compounds Download PDFInfo
- Publication number
- CA3085937A1 CA3085937A1 CA3085937A CA3085937A CA3085937A1 CA 3085937 A1 CA3085937 A1 CA 3085937A1 CA 3085937 A CA3085937 A CA 3085937A CA 3085937 A CA3085937 A CA 3085937A CA 3085937 A1 CA3085937 A1 CA 3085937A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- pyrrolo
- nrx
- piperidinyl
- pyridinyl
- 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.)
- Pending
Links
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 22
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 14
- -1 diazaspiro[4.5]decanonyl Chemical group 0.000 claims description 477
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 181
- 125000000217 alkyl group Chemical group 0.000 claims description 166
- 125000003386 piperidinyl group Chemical group 0.000 claims description 123
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 113
- 125000004076 pyridyl group Chemical group 0.000 claims description 99
- 125000002757 morpholinyl group Chemical group 0.000 claims description 95
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 92
- 125000004193 piperazinyl group Chemical group 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 70
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 65
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 60
- 125000002393 azetidinyl group Chemical group 0.000 claims description 56
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 54
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 45
- 201000006417 multiple sclerosis Diseases 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 125000005959 diazepanyl group Chemical group 0.000 claims description 42
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 41
- 125000003566 oxetanyl group Chemical group 0.000 claims description 38
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 35
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 34
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000002883 imidazolyl group Chemical group 0.000 claims description 26
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 22
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 108010011222 cyclo(Arg-Pro) Proteins 0.000 claims description 19
- 125000001425 triazolyl group Chemical group 0.000 claims description 19
- 125000003725 azepanyl group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 18
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
- 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 17
- VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 125000003944 tolyl group Chemical group 0.000 claims description 15
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000000335 thiazolyl group Chemical group 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 7
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 5
- AQWOIRBQLOOZGX-UHFFFAOYSA-N triazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=NN21 AQWOIRBQLOOZGX-UHFFFAOYSA-N 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- PZKFSRWSQOQYNR-UHFFFAOYSA-N 5-methyl-1h-1,2,4-triazole Chemical compound CC1=NC=NN1 PZKFSRWSQOQYNR-UHFFFAOYSA-N 0.000 claims description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 3
- 208000037976 chronic inflammation Diseases 0.000 claims description 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 3
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 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 2
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 241001645982 Crax Species 0.000 claims 3
- SWAOUIZDHXCDEB-UHFFFAOYSA-N 2-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=C(C)N=C21 SWAOUIZDHXCDEB-UHFFFAOYSA-N 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
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- 201000008827 tuberculosis Diseases 0.000 description 1
- 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
- 238000010626 work up procedure Methods 0.000 description 1
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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
- A61K31/4985—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
- A61K31/495—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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines 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
- A61K31/495—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
-
- 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (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)
- 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 |
|---|---|---|---|
| US201762607941P | 2017-12-20 | 2017-12-20 | |
| US62/607,941 | 2017-12-20 | ||
| PCT/US2018/066108 WO2019126083A1 (en) | 2017-12-20 | 2018-12-18 | Diazaindole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3085937A1 true CA3085937A1 (en) | 2019-06-27 |
Family
ID=65003573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3085937A Pending CA3085937A1 (en) | 2017-12-20 | 2018-12-18 | Diazaindole compounds |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US11299501B2 (https=) |
| EP (1) | EP3728264B1 (https=) |
| JP (1) | JP7382938B2 (https=) |
| KR (1) | KR102722182B1 (https=) |
| CN (1) | CN111511744B (https=) |
| AU (1) | AU2018390544A1 (https=) |
| BR (1) | BR112020012002A2 (https=) |
| CA (1) | CA3085937A1 (https=) |
| EA (1) | EA202091530A1 (https=) |
| ES (1) | ES2904773T3 (https=) |
| IL (1) | IL275505A (https=) |
| MX (1) | MX2020006014A (https=) |
| SG (1) | SG11202005733QA (https=) |
| WO (1) | WO2019126083A1 (https=) |
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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 |
| KR102730859B1 (ko) * | 2017-12-20 | 2024-11-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 및 헤테로아릴 치환된 인돌 화합물 |
| EP3728218B1 (en) * | 2017-12-20 | 2021-12-01 | Bristol-Myers Squibb Company | Amino indole compounds useful as tlr inhibitors |
| JP7328977B2 (ja) | 2018-02-12 | 2023-08-17 | エフ． ホフマン－ラ ロシュ アーゲー | ウイルス感染の処置および予防のための新規のスルホン化合物および誘導体 |
| EP3802539B1 (en) | 2018-06-05 | 2023-09-20 | F. Hoffmann-La Roche AG | Tetrahydro-1h-pyrazino[2,1-a]isoindolylquinoline compounds for the treatment of autoimmune disease |
| EP3807270B1 (en) | 2018-06-12 | 2023-09-13 | F. Hoffmann-La Roche AG | Novel heteroaryl heterocyclyl compounds for the treatment of autoimmune disease |
| 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 |
| EP3847169A1 (en) | 2018-09-04 | 2021-07-14 | F. Hoffmann-La Roche AG | Benzothiazole compounds for the treatment of autoimmune diseases |
| US11548884B2 (en) | 2018-09-06 | 2023-01-10 | Hoffmann-La Roche Inc. | Cyclic amidine compounds for the treatment of autoimmune disease |
| EP3847173B1 (en) | 2018-09-06 | 2023-04-12 | F. Hoffmann-La Roche AG | Novel pyrazolopyridine compounds for the treatment of autoimmune disease |
| WO2021084022A1 (en) | 2019-10-31 | 2021-05-06 | F. Hoffmann-La Roche Ag | Hydropyrazino[1,2-d][1,4]diazepine compounds for the treatment of autoimmune disease |
| CN114728976B (zh) | 2019-11-19 | 2024-08-16 | 豪夫迈·罗氏有限公司 | 用于治疗自身免疫性疾病的氢-1H-吡咯并[1,2-a]吡嗪化合物 |
| WO2021099406A1 (en) | 2019-11-20 | 2021-05-27 | F. Hoffmann-La Roche Ag | Spiro(isobenzofuranazetidine) compounds for the treatment of autoimmune disease |
| CN116075510A (zh) | 2020-08-19 | 2023-05-05 | 百时美施贵宝公司 | 1H-苯并[d]咪唑衍生物作为TLR9抑制剂用于治疗纤维化 |
| AU2021328575A1 (en) | 2020-08-19 | 2023-03-16 | Bristol-Myers Squibb Company | Imidazo(1,2-a)pyridine and (1,2,4)triazolo(1,5-a)pyridine derivatives as TLR9 inhibitors for the treatment of fibrosis |
| WO2022040267A1 (en) | 2020-08-19 | 2022-02-24 | Bristol-Myers Squibb Company | 1h-pyrrolo[3,2-c]pyridine and 1h-pyrrolo[2,3-c]pyridine derivatives as tlr9 inhibitors for the treatment of fibrosis |
| WO2022166920A1 (zh) * | 2021-02-08 | 2022-08-11 | 杭州中美华东制药有限公司 | 一种吡咯并哒嗪类化合物及其制备方法和用途 |
| CN116783202A (zh) * | 2021-02-09 | 2023-09-19 | 吉利德科学公司 | 噻吩并吡咯化合物 |
| CR20230478A (es) | 2021-04-16 | 2023-11-30 | Gilead Sciences Inc | Compuestos de tienopirrol. |
| KR20240056747A (ko) | 2021-09-10 | 2024-04-30 | 길리애드 사이언시즈, 인코포레이티드 | 티에노피롤 화합물 |
| MX2024009441A (es) * | 2022-02-18 | 2024-08-14 | Bristol Myers Squibb Co | Compuestos de imidazopiridinilo sustituidos utiles como inhibidores del receptor tipo toll 9 (tlr9). |
| 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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| DE102006033109A1 (de) | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
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| JP6223563B2 (ja) | 2013-10-14 | 2017-11-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 選択的に置換されたキノリン化合物 |
| CN105992766A (zh) | 2013-12-13 | 2016-10-05 | 武田药品工业株式会社 | 作为tlr抑制剂的吡咯并[3,2-c]吡啶衍生物 |
| HUE054672T2 (hu) | 2014-08-15 | 2021-09-28 | Chia Tai Tianqing Pharmaceutical Group Co Ltd | TLR7 agonistaként alkalmazott pirrolopirimidin vegyületek |
| EP3398948A3 (en) | 2014-08-22 | 2018-12-05 | Janus Biotherapeutics, Inc. | 2,4,6,7-tetrasubstituted pteridine compounds and methods of synthesis and use thereof |
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| BR112019001270A2 (pt) | 2016-07-30 | 2019-04-30 | Bristol-Myers Squibb Company | compostos indol substituídos com dimetoxifenila como inibidores de tlr7, tlr8 ou tlr9 |
| JP7028861B2 (ja) | 2016-09-09 | 2022-03-02 | ブリストル－マイヤーズ スクイブ カンパニー | ピリジル置換のインドール化合物 |
| JP7265554B2 (ja) | 2017-11-14 | 2023-04-26 | ブリストル－マイヤーズ スクイブ カンパニー | 置換インドール化合物 |
| EA202091484A1 (ru) | 2017-12-18 | 2021-03-25 | Бристол-Маерс Сквибб Компани | 4-азаиндольные соединения |
| JP7304352B2 (ja) | 2017-12-19 | 2023-07-06 | ブリストル－マイヤーズ スクイブ カンパニー | ６－アザインドール化合物 |
-
2018
- 2018-12-18 SG SG11202005733QA patent/SG11202005733QA/en unknown
- 2018-12-18 EP EP18830674.0A patent/EP3728264B1/en active Active
- 2018-12-18 EA EA202091530A patent/EA202091530A1/ru unknown
- 2018-12-18 BR BR112020012002-2A patent/BR112020012002A2/pt not_active Application Discontinuation
- 2018-12-18 CN CN201880082762.7A patent/CN111511744B/zh active Active
- 2018-12-18 WO PCT/US2018/066108 patent/WO2019126083A1/en not_active Ceased
- 2018-12-18 CA CA3085937A patent/CA3085937A1/en active Pending
- 2018-12-18 KR KR1020207020851A patent/KR102722182B1/ko active Active
- 2018-12-18 US US16/955,108 patent/US11299501B2/en active Active
- 2018-12-18 AU AU2018390544A patent/AU2018390544A1/en not_active Abandoned
- 2018-12-18 MX MX2020006014A patent/MX2020006014A/es unknown
- 2018-12-18 JP JP2020534861A patent/JP7382938B2/ja active Active
- 2018-12-18 ES ES18830674T patent/ES2904773T3/es active Active
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2020
- 2020-06-18 IL IL275505A patent/IL275505A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP7382938B2 (ja) | 2023-11-17 |
| BR112020012002A2 (pt) | 2020-11-17 |
| KR20200100760A (ko) | 2020-08-26 |
| EP3728264A1 (en) | 2020-10-28 |
| WO2019126083A1 (en) | 2019-06-27 |
| MX2020006014A (es) | 2020-08-17 |
| EP3728264B1 (en) | 2021-12-01 |
| ES2904773T3 (es) | 2022-04-06 |
| CN111511744B (zh) | 2023-09-22 |
| US11299501B2 (en) | 2022-04-12 |
| SG11202005733QA (en) | 2020-07-29 |
| KR102722182B1 (ko) | 2024-10-24 |
| JP2021506941A (ja) | 2021-02-22 |
| US20200308195A1 (en) | 2020-10-01 |
| CN111511744A (zh) | 2020-08-07 |
| IL275505A (en) | 2020-08-31 |
| AU2018390544A1 (en) | 2020-08-06 |
| EA202091530A1 (ru) | 2020-09-14 |
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