JP7046827B2 - イミダゾ［１，５－ａ］ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 - Google Patents
イミダゾ［１，５－ａ］ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 Download PDFInfo
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- JP7046827B2 JP7046827B2 JP2018552716A JP2018552716A JP7046827B2 JP 7046827 B2 JP7046827 B2 JP 7046827B2 JP 2018552716 A JP2018552716 A JP 2018552716A JP 2018552716 A JP2018552716 A JP 2018552716A JP 7046827 B2 JP7046827 B2 JP 7046827B2
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- cycloalkyl
- alkyl
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- 238000011282 treatment Methods 0.000 title claims description 27
- HYQUTQMHYJEWLG-UHFFFAOYSA-N N=1C=2N(C=CC=1C(=O)N)C=NC=2 Chemical class N=1C=2N(C=CC=1C(=O)N)C=NC=2 HYQUTQMHYJEWLG-UHFFFAOYSA-N 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims description 369
- 125000000217 alkyl group Chemical group 0.000 claims description 180
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 154
- 125000003545 alkoxy group Chemical group 0.000 claims description 128
- 229910052736 halogen Inorganic materials 0.000 claims description 96
- 150000002367 halogens Chemical class 0.000 claims description 93
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 81
- 125000000623 heterocyclic group Chemical group 0.000 claims description 75
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 66
- 125000001424 substituent group Chemical group 0.000 claims description 61
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 48
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 42
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
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- 208000001089 Multiple system atrophy Diseases 0.000 claims description 16
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 15
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- 125000004452 carbocyclyl group Chemical group 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 125000002971 oxazolyl group Chemical group 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 10
- 206010012289 Dementia Diseases 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
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- 238000006467 substitution reaction Methods 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 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 8
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- 206010015037 epilepsy Diseases 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 7
- 208000024714 major depressive disease Diseases 0.000 claims description 7
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- 208000026292 Cystic Kidney disease Diseases 0.000 claims description 6
- 206010030348 Open-Angle Glaucoma Diseases 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
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- 201000009273 Endometriosis Diseases 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 2
- 208000034189 Sclerosis Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- -1 2-methyl- 3-Butyl Chemical group 0.000 description 570
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 457
- 239000007787 solid Substances 0.000 description 370
- 238000007429 general method Methods 0.000 description 336
- 238000005481 NMR spectroscopy Methods 0.000 description 224
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- 239000000203 mixture Substances 0.000 description 170
- 239000000243 solution Substances 0.000 description 122
- 230000002829 reductive effect Effects 0.000 description 109
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 239000000706 filtrate Substances 0.000 description 59
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 55
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- 239000011734 sodium Substances 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- QCCCRRJRLITNMB-UHFFFAOYSA-N 2-chloro-4-ethyl-5-methyl-1H-imidazole Chemical compound C(C)C1=C(N=C(N1)Cl)C QCCCRRJRLITNMB-UHFFFAOYSA-N 0.000 description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 238000000034 method Methods 0.000 description 38
- 238000010898 silica gel chromatography Methods 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000003921 oil Substances 0.000 description 32
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- 125000003636 chemical group Chemical group 0.000 description 30
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- 150000002460 imidazoles Chemical class 0.000 description 27
- 229920006395 saturated elastomer Polymers 0.000 description 27
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 26
- 235000019439 ethyl acetate Nutrition 0.000 description 26
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 150000001408 amides Chemical class 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 239000004698 Polyethylene Substances 0.000 description 23
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical class NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
- 239000003814 drug Substances 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- IXCXVGWKYIDNOS-BYPYZUCNSA-N (1s)-1-cyclopropylethanamine Chemical compound C[C@H](N)C1CC1 IXCXVGWKYIDNOS-BYPYZUCNSA-N 0.000 description 19
- OOXIEUXBOSSXJM-UHFFFAOYSA-N 2-cyclopropylpropan-2-amine Chemical compound CC(C)(N)C1CC1 OOXIEUXBOSSXJM-UHFFFAOYSA-N 0.000 description 18
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- NJMORFFDAXJHHM-UHFFFAOYSA-N ethyl 4-amino-1h-imidazole-5-carboxylate Chemical compound CCOC(=O)C=1NC=NC=1N NJMORFFDAXJHHM-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 238000010168 coupling process Methods 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- FITMUOODICYTRA-UHFFFAOYSA-N 2-chloro-5-methyl-1h-imidazole Chemical compound CC1=CN=C(Cl)N1 FITMUOODICYTRA-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
- 230000008878 coupling Effects 0.000 description 14
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- WGYUEZQGJJLCKF-UHFFFAOYSA-N 3-(5-methyl-1h-imidazol-2-yl)pyridine Chemical compound N1C(C)=CN=C1C1=CC=CN=C1 WGYUEZQGJJLCKF-UHFFFAOYSA-N 0.000 description 12
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- VTLYNMLFFMGINP-UHFFFAOYSA-N 2-chloro-4,5-diethyl-1H-imidazole Chemical compound C(C)C1=C(N=C(N1)Cl)CC VTLYNMLFFMGINP-UHFFFAOYSA-N 0.000 description 11
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- WXRSEUXBXNDCKE-UHFFFAOYSA-N imidazo[1,5-a]pyrimidine-8-carboxylic acid Chemical compound C1=CC=NC2=C(C(=O)O)N=CN21 WXRSEUXBXNDCKE-UHFFFAOYSA-N 0.000 description 10
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- ZTUJDPKOHPKRMO-UHFFFAOYSA-N hydron;2,2,2-trifluoroethanamine;chloride Chemical compound Cl.NCC(F)(F)F ZTUJDPKOHPKRMO-UHFFFAOYSA-N 0.000 description 7
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- PODROGPCZGDXQX-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-1H-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC(Cl)=C1 PODROGPCZGDXQX-UHFFFAOYSA-N 0.000 description 5
- QMPGOIRXGZLJFV-UHFFFAOYSA-N 2-(3-methoxyphenyl)-5-methyl-1h-imidazole Chemical compound COC1=CC=CC(C=2NC(C)=CN=2)=C1 QMPGOIRXGZLJFV-UHFFFAOYSA-N 0.000 description 5
- CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 5
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 5
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- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- 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
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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
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| KR102662215B1 (ko) | 2014-11-06 | 2024-05-02 | 비알 - 알&디 인베스트먼츠, 에스.에이. | 치환된 피라졸로(1,5-a)피리미딘 및 의학적 장애의 치료에서의 그의 용도 |
| WO2016073891A1 (en) | 2014-11-06 | 2016-05-12 | Lysosomal Therapeutics Inc. | Substituted pyrrolo[1,2-a]pyrimidines and their use in the treatment of medical disorders |
| US20170333435A1 (en) | 2014-11-06 | 2017-11-23 | Lysosomal Therapeutics Inc. | Substituted imidazo[1,5-a]pyrimidines and their use in the treatment of medical disorders |
| US11192892B2 (en) | 2016-04-06 | 2021-12-07 | Bial—R&D Investments, S.A. | Substituted pyrazolo[1,5-a]pyrimidines for the treatment of medical disorders |
| JP7034935B2 (ja) | 2016-04-06 | 2022-03-14 | リソソーマル・セラピューティクス・インコーポレイテッド | ピロロ［１，２－ａ］ピリミジニルカルボキサミド化合物および医学的障害の処置におけるその使用 |
| WO2017176961A1 (en) | 2016-04-06 | 2017-10-12 | Lysosomal Therapeutics Inc. | Imidazo [1,5-a]pyrimidinyl carboxamide compounds and their use in the treatment of medical disorders |
| WO2017192930A1 (en) | 2016-05-05 | 2017-11-09 | Lysosomal Therapeutics Inc. | SUBSTITUTED IMIDAZO[1,2-b]PYRIDAZINES, SUBSTITUTED IMIDAZO[1,5-b]PYRIDAZINES, RELATED COMPOUNDS, AND THEIR USE IN THE TREATMENT OF MEDICAL DISORDERS |
| US11345698B2 (en) | 2016-05-05 | 2022-05-31 | Bial—R&D Investments, S.A. | Substituted imidazo[1,2-a]pyridines, substituted imidazo[1,2-a]pyrazines, related compounds, and their use in the treatment of medical disorders |
| CN116283995B (zh) * | 2022-09-08 | 2023-12-29 | 华中科技大学同济医学院附属同济医院 | 一种脂酰辅酶a合成酶短链家族成员3的激动剂及其应用 |
| CN116514665B (zh) * | 2023-05-09 | 2025-01-28 | 南京优氟医药科技有限公司 | 一种(r)-2,2,2-三氟-1-苯乙胺盐酸盐的制备方法 |
| WO2025146216A1 (zh) * | 2024-01-05 | 2025-07-10 | 成都赜灵生物医药科技有限公司 | 六并五氮杂环酰胺类化合物及其用途 |
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| US20210309661A1 (en) | 2021-10-07 |
| EP3440083A1 (en) | 2019-02-13 |
| EP3440083A4 (en) | 2019-09-18 |
| US10787454B2 (en) | 2020-09-29 |
| US9920061B2 (en) | 2018-03-20 |
| WO2017176961A1 (en) | 2017-10-12 |
| US20170349599A1 (en) | 2017-12-07 |
| MX2018012208A (es) | 2019-03-28 |
| CA3020305A1 (en) | 2017-10-12 |
| JP2019510794A (ja) | 2019-04-18 |
| US11453675B2 (en) | 2022-09-27 |
| US20190119283A1 (en) | 2019-04-25 |
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