ES2921020T3 - Compuestos de indol sustituidos con [1,2,4]triazolo[4,3-a]piridinilo - Google Patents
Compuestos de indol sustituidos con [1,2,4]triazolo[4,3-a]piridinilo Download PDFInfo
- Publication number
- ES2921020T3 ES2921020T3 ES18759464T ES18759464T ES2921020T3 ES 2921020 T3 ES2921020 T3 ES 2921020T3 ES 18759464 T ES18759464 T ES 18759464T ES 18759464 T ES18759464 T ES 18759464T ES 2921020 T3 ES2921020 T3 ES 2921020T3
- Authority
- ES
- Spain
- Prior art keywords
- triazolo
- indol
- isopropyl
- piperidin
- pyridine
- 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 [1,2,4]triazolo[4,3-a]pyridinyl-substituted indole compounds Chemical class 0.000 title claims description 122
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 96
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 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 18
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 17
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 17
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 201000006417 multiple sclerosis Diseases 0.000 claims description 13
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
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- 125000003566 oxetanyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
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- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
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Classifications
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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
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762541331P | 2017-08-04 | 2017-08-04 | |
| PCT/US2018/045080 WO2019028301A1 (en) | 2017-08-04 | 2018-08-03 | INDOLE COMPOUNDS SUBSTITUTED WITH [1,2,4] TRIAZOLO [4,3-A] PYRIDINYL |
Publications (1)
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| CN110997670B (zh) | 2017-08-04 | 2022-11-01 | 百时美施贵宝公司 | [1,2,4]三唑并[4,3-a]吡啶基取代的吲哚化合物 |
| EA202091474A1 (ru) | 2017-12-19 | 2020-11-18 | Бристол-Маерс Сквибб Компани | Замещенные индольные соединения, применимые в качестве ингибиторов tlr |
| WO2019155042A1 (en) | 2018-02-12 | 2019-08-15 | F. Hoffmann-La Roche Ag | Novel sulfone compounds and derivatives for the treatment and prophylaxis of virus infection |
| US12157746B2 (en) | 2018-06-05 | 2024-12-03 | Hoffmann-La Roche Inc. | 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 |
| US11952363B2 (en) | 2018-07-23 | 2024-04-09 | Hoffmann-La Roche Inc. | Piperazine compounds for the treatment of autoimmune disease |
| 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 |
| EP3847170B1 (en) | 2018-09-06 | 2022-06-22 | F. Hoffmann-La Roche AG | Novel cyclic amidine compounds for the treatment of autoimmune disease |
| WO2020048596A1 (en) | 2018-09-06 | 2020-03-12 | F. Hoffmann-La Roche Ag | Novel pyrazolopyridine compounds for the treatment of autoimmune disease |
| CN114599652B (zh) | 2019-10-31 | 2024-07-12 | 豪夫迈·罗氏有限公司 | 用于治疗自身免疫性疾病的氢吡嗪并[1,2-d][1,4]二氮杂䓬化合物 |
| EP4061816A1 (en) | 2019-11-19 | 2022-09-28 | F. Hoffmann-La Roche AG | Hydro-1h-pyrrolo[1,2-a]pyrazine compounds for the treatment of autoimmune disease |
| EP4061821B1 (en) | 2019-11-20 | 2025-08-06 | F. Hoffmann-La Roche AG | Spiro(isobenzofuranazetidine) compounds for the treatment of autoimmune disease |
| EP4200297B1 (en) | 2020-08-19 | 2026-05-13 | 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 |
| US12492188B2 (en) | 2020-08-19 | 2025-12-09 | Bristol-Myers Squibb Company | 1H-benzo[D]imidazole derivatives as TLR9 inhibitors for the treatment of fibrosis |
| CN116783202A (zh) * | 2021-02-09 | 2023-09-19 | 吉利德科学公司 | 噻吩并吡咯化合物 |
| US11661431B2 (en) | 2021-04-16 | 2023-05-30 | Gilead Sciences, Inc. | Thienopyrrole compounds |
| TW202440078A (zh) | 2021-09-10 | 2024-10-16 | 美商基利科學股份有限公司 | 噻吩并吡咯化合物 |
| 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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| FR2926556B1 (fr) | 2008-01-22 | 2010-02-19 | Sanofi Aventis | Derives de carboxamides n-azabicycliques, leur preparation et leur application en therapeutique |
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| TW201609693A (zh) * | 2014-01-03 | 2016-03-16 | 必治妥美雅史谷比公司 | 雜芳基取代之菸鹼醯胺化合物 |
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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 |
| CN109715617B (zh) * | 2016-07-30 | 2022-04-19 | 百时美施贵宝公司 | 作为tlr7、tlr8或tlr9抑制剂的二甲氧基苯基取代的吲哚化合物 |
| ES2902504T3 (es) * | 2016-09-09 | 2022-03-28 | Bristol Myers Squibb Co | Compuestos de indol sustituidos con piridilo |
| SG11201901672RA (en) * | 2016-09-16 | 2019-03-28 | Nordic Nanovector Asa | Treatment of non-hodgkin lymphoma using lilotomab and 177lu-lilotomab satetraxetan |
| CN110997670B (zh) | 2017-08-04 | 2022-11-01 | 百时美施贵宝公司 | [1,2,4]三唑并[4,3-a]吡啶基取代的吲哚化合物 |
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