EA037953B1 - N-замещенные индольные производные в качестве антагонистов pge2 рецепторов - Google Patents
N-замещенные индольные производные в качестве антагонистов pge2 рецепторов Download PDFInfo
- Publication number
- EA037953B1 EA037953B1 EA201891179A EA201891179A EA037953B1 EA 037953 B1 EA037953 B1 EA 037953B1 EA 201891179 A EA201891179 A EA 201891179A EA 201891179 A EA201891179 A EA 201891179A EA 037953 B1 EA037953 B1 EA 037953B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- pyrimidin
- fluoro
- ethylamino
- methoxy
- methylindol
- Prior art date
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- -1 N-substituted indole Chemical class 0.000 title claims description 1357
- 102000008866 Prostaglandin E receptors Human genes 0.000 title description 6
- 108010088540 Prostaglandin E receptors Proteins 0.000 title description 6
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 229940044551 receptor antagonist Drugs 0.000 title description 3
- 239000002464 receptor antagonist Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 239000003814 drug Substances 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 368
- 229910052739 hydrogen Inorganic materials 0.000 claims description 309
- 239000001257 hydrogen Substances 0.000 claims description 309
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 248
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 169
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 134
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 134
- 125000001424 substituent group Chemical group 0.000 claims description 125
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 113
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 100
- 229910052731 fluorine Inorganic materials 0.000 claims description 96
- 239000011737 fluorine Substances 0.000 claims description 96
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 88
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- 239000000460 chlorine Substances 0.000 claims description 83
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 77
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 77
- 229910052717 sulfur Inorganic materials 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 70
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims description 68
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 64
- 229910052736 halogen Inorganic materials 0.000 claims description 64
- 150000002367 halogens Chemical class 0.000 claims description 64
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 62
- 229910052801 chlorine Inorganic materials 0.000 claims description 62
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
- 150000002431 hydrogen Chemical class 0.000 claims description 60
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 52
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 48
- 239000011593 sulfur Substances 0.000 claims description 48
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 44
- 125000005842 heteroatom Chemical group 0.000 claims description 43
- 102100024450 Prostaglandin E2 receptor EP4 subtype Human genes 0.000 claims description 40
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 36
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 30
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 27
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
- 125000004434 sulfur atom Chemical group 0.000 claims description 27
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- 125000000335 thiazolyl group Chemical group 0.000 claims description 24
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 20
- 101150109738 Ptger4 gene Proteins 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000001041 indolyl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 15
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 13
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 13
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 13
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 12
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
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- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 11
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 238000001959 radiotherapy Methods 0.000 claims description 11
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 9
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- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
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- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- UIRRBSPUIYGBOF-UHFFFAOYSA-N 5-[6-[2-(2-cyano-7-fluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound C(#N)C=1N(C2=C(C=CC(=C2C=1)OC)F)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC UIRRBSPUIYGBOF-UHFFFAOYSA-N 0.000 claims description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
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- 230000004770 neurodegeneration Effects 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- CTQPPUPWHLGKOB-UHFFFAOYSA-N 4h-oxadiazol-5-one Chemical compound O=C1CN=NO1 CTQPPUPWHLGKOB-UHFFFAOYSA-N 0.000 claims description 6
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
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- GWEYPKZLUHKSPZ-UHFFFAOYSA-N 1-[2-[[6-(2-cyclopropylpyridin-4-yl)pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound C1(CC1)C1=NC=CC(=C1)C1=CC(=NC=N1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N GWEYPKZLUHKSPZ-UHFFFAOYSA-N 0.000 claims description 2
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- MOMJSYQKXSMPEF-UHFFFAOYSA-N 2-(ethylamino)-4-[6-[2-(6-fluoro-2,4-dimethylindol-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)NC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=C(C=C12)F)C)C MOMJSYQKXSMPEF-UHFFFAOYSA-N 0.000 claims description 2
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- 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| EP2015077269 | 2015-11-20 | ||
| PCT/EP2016/078028 WO2017085198A1 (en) | 2015-11-20 | 2016-11-17 | N-substituted indole derivatives as pge2 receptor modulators |
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| CN117105827A (zh) | 2017-03-27 | 2023-11-24 | 魁北克电力公司 | 用于电解质组合物中或用作电极添加剂的盐 |
| AR111808A1 (es) | 2017-05-18 | 2019-08-21 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores del receptor de pge2 |
| US11325899B2 (en) | 2017-05-18 | 2022-05-10 | Idorsia Pharmaceuticals Ltd | Benzofurane and benzothiophene derivatives as PGE2 receptor modulators |
| EA201992676A1 (ru) | 2017-05-18 | 2020-05-06 | Идорсия Фармасьютиклз Лтд | Фенильные производные в качестве модуляторов pge2 рецепторов |
| KR102612140B1 (ko) | 2017-05-18 | 2023-12-08 | 이도르시아 파마슈티컬스 리미티드 | 피리미딘 유도체 |
| CN109678780A (zh) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | 一种制备3-烷基吲哚衍生物的方法 |
| WO2019100062A1 (en) | 2017-11-20 | 2019-05-23 | Ichan School Of Medicine At Mount Sinai | Kinase inhibitor compounds and compositions and methods of use |
| JP2021510153A (ja) | 2018-01-05 | 2021-04-15 | アイカーン スクール オブ メディシン アット マウント サイナイ | 膵臓ベータ細胞の増殖を増加させる方法、治療方法、および組成物 |
| ES3038913T3 (en) | 2018-03-20 | 2025-10-15 | Icahn School Med Mount Sinai | Beta-carboline derivatives as dyrk1a inhibitors for the treatment of e.g. diabetes |
| CA3124353A1 (en) * | 2018-12-31 | 2020-07-09 | Icahn School Of Medicine At Mount Sinai | Kinase inhibitor compounds and compositions and methods of use |
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| MX2022005359A (es) | 2019-11-04 | 2022-06-02 | Revolution Medicines Inc | Inhibidores de ras. |
| IL301298A (en) | 2020-09-15 | 2023-05-01 | Revolution Medicines Inc | Indole derivatives as RAS inhibitors in cancer therapy |
| JP7816164B2 (ja) | 2020-11-13 | 2026-02-18 | 小野薬品工業株式会社 | Ｅｐ４拮抗薬と免疫チェックポイント阻害物質との併用によるがん治療 |
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| CN117567461A (zh) * | 2023-10-13 | 2024-02-20 | 佛山奕安赛医药科技有限公司 | 一种维利西呱中间体的制备方法 |
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