JP2024038267A5 - - Google Patents
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- JP2024038267A5 JP2024038267A5 JP2024000646A JP2024000646A JP2024038267A5 JP 2024038267 A5 JP2024038267 A5 JP 2024038267A5 JP 2024000646 A JP2024000646 A JP 2024000646A JP 2024000646 A JP2024000646 A JP 2024000646A JP 2024038267 A5 JP2024038267 A5 JP 2024038267A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- carboxamide
- oxopiperazine
- chloro
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 182
- 125000001424 substituent group Chemical group 0.000 claims 85
- 125000000753 cycloalkyl group Chemical group 0.000 claims 70
- 229910052739 hydrogen Inorganic materials 0.000 claims 70
- 239000001257 hydrogen Substances 0.000 claims 70
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 60
- 229910052736 halogen Inorganic materials 0.000 claims 58
- 150000002367 halogens Chemical class 0.000 claims 58
- 125000000304 alkynyl group Chemical group 0.000 claims 43
- 125000003342 alkenyl group Chemical group 0.000 claims 41
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 28
- 150000003839 salts Chemical class 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 16
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 16
- 229910052805 deuterium Inorganic materials 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 14
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 12
- 208000035475 disorder Diseases 0.000 claims 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 10
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims 8
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 8
- 208000027520 Somatoform disease Diseases 0.000 claims 6
- MKCBRYIXFFGIKN-UHFFFAOYSA-N bicyclo[1.1.1]pentane Chemical compound C1C2CC1C2 MKCBRYIXFFGIKN-UHFFFAOYSA-N 0.000 claims 6
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 claims 6
- JAPMJSVZDUYFKL-UHFFFAOYSA-N bicyclo[3.1.0]hexane Chemical compound C1CCC2CC21 JAPMJSVZDUYFKL-UHFFFAOYSA-N 0.000 claims 6
- LPCWKMYWISGVSK-UHFFFAOYSA-N bicyclo[3.2.1]octane Chemical compound C1C2CCC1CCC2 LPCWKMYWISGVSK-UHFFFAOYSA-N 0.000 claims 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 6
- 208000027753 pain disease Diseases 0.000 claims 6
- OGNAOIGAPPSUMG-UHFFFAOYSA-N spiro[2.2]pentane Chemical compound C1CC11CC1 OGNAOIGAPPSUMG-UHFFFAOYSA-N 0.000 claims 6
- FYGUBWKMMCWIKB-UHFFFAOYSA-N spiro[2.3]hexane Chemical compound C1CC11CCC1 FYGUBWKMMCWIKB-UHFFFAOYSA-N 0.000 claims 6
- FOEYMRPOKBCNCR-UHFFFAOYSA-N spiro[2.5]octane Chemical compound C1CC11CCCCC1 FOEYMRPOKBCNCR-UHFFFAOYSA-N 0.000 claims 6
- LBJQKYPPYSCCBH-UHFFFAOYSA-N spiro[3.3]heptane Chemical compound C1CCC21CCC2 LBJQKYPPYSCCBH-UHFFFAOYSA-N 0.000 claims 6
- 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 5
- 208000003251 Pruritus Diseases 0.000 claims 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 4
- 125000005217 alkenylheteroaryl group Chemical group 0.000 claims 4
- 125000005025 alkynylaryl group Chemical group 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
- 150000003557 thiazoles Chemical class 0.000 claims 4
- LAZLMPFKMYEUQC-PRFIWBCESA-N C[C@H](C(NCC1)=O)N1C(N[C@@H]([C@H](C1)C[C@@H]1C(F)(F)F)C(C=C1)=NC(C(F)(F)F)=C1Cl)=O Chemical compound C[C@H](C(NCC1)=O)N1C(N[C@@H]([C@H](C1)C[C@@H]1C(F)(F)F)C(C=C1)=NC(C(F)(F)F)=C1Cl)=O LAZLMPFKMYEUQC-PRFIWBCESA-N 0.000 claims 2
- REGVIHGWFHKBFF-MSFDSXBXSA-N C[C@H](C(NCC1)=O)N1C(N[C@@H]([C@H](C1)C[C@@H]1C(F)(F)F)C(C=CC(F)=C1Cl)=C1F)=O Chemical compound C[C@H](C(NCC1)=O)N1C(N[C@@H]([C@H](C1)C[C@@H]1C(F)(F)F)C(C=CC(F)=C1Cl)=C1F)=O REGVIHGWFHKBFF-MSFDSXBXSA-N 0.000 claims 2
- XNBHHZMLFHBMJD-MWRCMHLZSA-N C[C@H](C(NCC1)=O)N1C(N[C@@H]([C@H](CC1)CO[C@@H]1C(F)(F)F)C(C=CC(F)=C1Cl)=C1F)=O Chemical compound C[C@H](C(NCC1)=O)N1C(N[C@@H]([C@H](CC1)CO[C@@H]1C(F)(F)F)C(C=CC(F)=C1Cl)=C1F)=O XNBHHZMLFHBMJD-MWRCMHLZSA-N 0.000 claims 2
- LAZLMPFKMYEUQC-VWMGYNLJSA-N C[C@H](C(NCC1)=O)N1C(N[C@H]([C@H](C1)C[C@@H]1C(F)(F)F)C(C=C1)=NC(C(F)(F)F)=C1Cl)=O Chemical compound C[C@H](C(NCC1)=O)N1C(N[C@H]([C@H](C1)C[C@@H]1C(F)(F)F)C(C=C1)=NC(C(F)(F)F)=C1Cl)=O LAZLMPFKMYEUQC-VWMGYNLJSA-N 0.000 claims 2
- 206010011224 Cough Diseases 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- FKCCIPFBCVEZGL-UTEYVOQOSA-N O=C(N[C@@H]([C@H](C1)C[C@@H]1C(F)(F)F)C(C=CC(F)=C1Cl)=C1F)N(CCN1)CC1=O Chemical compound O=C(N[C@@H]([C@H](C1)C[C@@H]1C(F)(F)F)C(C=CC(F)=C1Cl)=C1F)N(CCN1)CC1=O FKCCIPFBCVEZGL-UTEYVOQOSA-N 0.000 claims 2
- HYGXNUDBNTXDSV-SUYBPPKGSA-N O=C(N[C@H]([C@H](CC1)CC[C@@H]1C(F)(F)F)C(C=C1)=CC=C1Cl)N(CCN1)CC1=O Chemical compound O=C(N[C@H]([C@H](CC1)CC[C@@H]1C(F)(F)F)C(C=C1)=CC=C1Cl)N(CCN1)CC1=O HYGXNUDBNTXDSV-SUYBPPKGSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- REGVIHGWFHKBFF-VYWCNIQISA-N [2H]C([2H])(C([2H])([2H])N([C@@H]1C)C(N[C@@H]([C@H](C2)C[C@@H]2C(F)(F)F)C(C=CC(F)=C2Cl)=C2F)=O)NC1=O Chemical compound [2H]C([2H])(C([2H])([2H])N([C@@H]1C)C(N[C@@H]([C@H](C2)C[C@@H]2C(F)(F)F)C(C=CC(F)=C2Cl)=C2F)=O)NC1=O REGVIHGWFHKBFF-VYWCNIQISA-N 0.000 claims 2
- REGVIHGWFHKBFF-VIWBBKFRSA-N [2H]C([2H])(C([2H])([2H])N([C@H]1C)C(N[C@@H]([C@H](C2)C[C@@H]2C(F)(F)F)C(C=CC(F)=C2Cl)=C2F)=O)NC1=O Chemical compound [2H]C([2H])(C([2H])([2H])N([C@H]1C)C(N[C@@H]([C@H](C2)C[C@@H]2C(F)(F)F)C(C=CC(F)=C2Cl)=C2F)=O)NC1=O REGVIHGWFHKBFF-VIWBBKFRSA-N 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 208000005298 acute pain Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 2
- -1 (2R)-N-((S)-(3-chloro-2,4-difluorophenyl)(6,6-difluorospiro[3.3]heptan-2-yl)methyl)-2-methyl-3-oxopiperazine-1-carboxamide Chemical compound 0.000 claims 1
- BRDDCXBGXYZTNS-INIZCTEOSA-N CC(C)(C1)CC1[C@@H](C(C=CC(F)=C1Cl)=C1F)NC(N(CCN1)CC1=O)=O Chemical compound CC(C)(C1)CC1[C@@H](C(C=CC(F)=C1Cl)=C1F)NC(N(CCN1)CC1=O)=O BRDDCXBGXYZTNS-INIZCTEOSA-N 0.000 claims 1
- BRDDCXBGXYZTNS-MRXNPFEDSA-N CC(C)(C1)CC1[C@H](C(C=CC(F)=C1Cl)=C1F)NC(N(CCN1)CC1=O)=O Chemical compound CC(C)(C1)CC1[C@H](C(C=CC(F)=C1Cl)=C1F)NC(N(CCN1)CC1=O)=O BRDDCXBGXYZTNS-MRXNPFEDSA-N 0.000 claims 1
- XHBYLKIDSCGNMY-SANLESKHSA-N C[C@H](C(NCC1)=O)N1C(N[C@@H](C(C1)(C2)CC12C(F)(F)F)C(C=C1)=CC(Cl)=C1F)=O Chemical compound C[C@H](C(NCC1)=O)N1C(N[C@@H](C(C1)(C2)CC12C(F)(F)F)C(C=C1)=CC(Cl)=C1F)=O XHBYLKIDSCGNMY-SANLESKHSA-N 0.000 claims 1
- WGRYWEDPPPNVDQ-LMXJLVQFSA-N C[C@H](C(NCC1)=O)N1C(N[C@@H](C(C1)(C2)CC12C(F)(F)F)C(C=CC(F)=C1Cl)=C1F)=O Chemical compound C[C@H](C(NCC1)=O)N1C(N[C@@H](C(C1)(C2)CC12C(F)(F)F)C(C=CC(F)=C1Cl)=C1F)=O WGRYWEDPPPNVDQ-LMXJLVQFSA-N 0.000 claims 1
- BAADRDJKNQWSRZ-CLAHSXSESA-N C[C@H](C(NCC1)=O)N1C(N[C@@H](C(C1)CC1(F)F)C(C=CC(F)=C1Cl)=C1F)=O Chemical compound C[C@H](C(NCC1)=O)N1C(N[C@@H](C(C1)CC1(F)F)C(C=CC(F)=C1Cl)=C1F)=O BAADRDJKNQWSRZ-CLAHSXSESA-N 0.000 claims 1
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| AU2022270061B2 (en) * | 2021-05-07 | 2026-02-19 | Merck Sharp & Dohme Llc | Aryl 3-oxopiperazine carboxamides and heteroaryl 3-oxopiperazine carboxamides as nav1.8 inhibitors |
| CA3257285A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | HETEROARYL COMPOUNDS FOR PAIN RELIEF |
| CA3256248A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | HETEROARYL COMPOUNDS FOR PAIN RELIEF |
| US20230382910A1 (en) | 2022-04-22 | 2023-11-30 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| WO2023205463A1 (en) | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| WO2024123815A1 (en) | 2022-12-06 | 2024-06-13 | Vertex Pharmaceuticals Incorporated | Process for the synthesis of substituted tetrahydrofuran modulators of sodium channels |
| WO2025085564A1 (en) * | 2023-10-16 | 2025-04-24 | Kronos Bio, Inc. | Lysine acetyltransferase inhibitors |
| CN117645533B (zh) * | 2023-10-20 | 2024-10-11 | 泰州精英化成医药科技有限公司 | 一种4-(三氟甲基)环己酮的合成方法 |
| WO2025090516A1 (en) | 2023-10-23 | 2025-05-01 | Vertex Pharmaceuticals Incorporated | Methods of preparing compounds for treating pain and solid forms thereof |
| WO2025090511A1 (en) | 2023-10-23 | 2025-05-01 | Vertex Pharmaceuticals Incorporated | Methods of preparing modulators of sodium channels and solid forms of the same for treating pain |
| WO2025090480A1 (en) | 2023-10-23 | 2025-05-01 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| WO2025090465A1 (en) | 2023-10-23 | 2025-05-01 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| CN117567323A (zh) * | 2023-10-30 | 2024-02-20 | 湖北泰盛化工有限公司 | 一种(s)-4-氯-2-((甲氧基羰基)氨基)丁酸乙酯的制备方法 |
| US20250186419A1 (en) | 2023-12-07 | 2025-06-12 | Vertex Pharmaceuticals Incorporated | Dosing regimens for treating pain |
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| WO2026013449A2 (en) | 2024-07-11 | 2026-01-15 | Sea4Us - Biotecnologia E Recursos Marinhos, Sa | Oxazolidone-derived compounds and their use in the treatment of chronic and acute pain |
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| JPS52122392A (en) * | 1976-04-07 | 1977-10-14 | Sangyo Kagaku Kenkyu Kyokai | Novel antibacterials |
| WO2005061470A1 (en) * | 2003-12-18 | 2005-07-07 | Cv Therapeutics, Inc. | 1-akan-2-ol substituted piperazine and piperidine compounds |
| KR20100075631A (ko) | 2007-10-11 | 2010-07-02 | 버텍스 파마슈티칼스 인코포레이티드 | 전압개폐 나트륨 채널의 억제제로서 유용한 아릴 아미드 |
| WO2009049181A1 (en) | 2007-10-11 | 2009-04-16 | Vertex Pharmaceuticals Incorporated | Amides useful as inhibitors of voltage-gated sodium channels |
| AU2008310660A1 (en) | 2007-10-11 | 2009-04-16 | Vertex Pharmaceuticals Incorporated | Heteroaryl amides useful as inhibitors of voltage-gated sodium channels |
| WO2011026240A1 (en) * | 2009-09-04 | 2011-03-10 | Zalicus Pharmaceuticals Ltd. | Oxopiperazine derivatives for the treatment of pain and epilepsy |
| US8889863B2 (en) * | 2010-07-16 | 2014-11-18 | Vanderbilt University | Stereoselective methods, catalysts and intermediates for the synthesis of (−)-Nutlin-3 and related compounds |
| RS56015B1 (sr) | 2013-01-31 | 2017-09-29 | Vertex Pharma | Piridon amidi kao modulatori natrijumovih kanala |
| CA2898653C (en) | 2013-01-31 | 2021-09-28 | Vertex Pharmaceuticals Incorporated | Amides as modulators of sodium channels |
| RU2683788C2 (ru) | 2013-01-31 | 2019-04-02 | Вертекс Фармасьютикалз Инкорпорейтед | Амиды хинолина и хиназолина, полезные в качестве модуляторов натриевых каналов |
| UA119147C2 (uk) | 2013-07-19 | 2019-05-10 | Вертекс Фармасьютікалз Інкорпорейтед | Сульфонаміди як модулятори натрієвих каналів |
| CA2931550C (en) | 2013-12-13 | 2023-09-26 | Vertex Pharmaceuticals Incorporated | Prodrugs of pyridone amides useful as modulators of sodium channels |
| JP2017114764A (ja) * | 2014-04-25 | 2017-06-29 | 武田薬品工業株式会社 | 片頭痛治療剤 |
| WO2015184383A1 (en) * | 2014-05-29 | 2015-12-03 | St. Jude Children's Research Hospital | Aryl-substituted imidazoles and methods of making and using same |
| WO2017209322A1 (ko) | 2016-05-31 | 2017-12-07 | 한림대학교 산학협력단 | 5원 헤테로사이클릭 유도체, 이의 제조방법 및 이를 포함하는 약제학적 조성물 |
| EP3625214B1 (en) | 2017-05-16 | 2022-07-06 | Vertex Pharmaceuticals Incorporated | Deuterated pyridone amides and prodrugs thereof as modulators of sodium channels |
| AU2018300150A1 (en) | 2017-07-11 | 2020-01-30 | Vertex Pharmaceuticals Incorporated | Carboxamides as modulators of sodium channels |
| AU2018371216B2 (en) * | 2017-11-23 | 2024-09-19 | Oslo University Hospital Hf | Treatment of tachycardia |
| EP3802551A4 (en) * | 2018-05-25 | 2022-03-02 | Venatorx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| JP7288051B2 (ja) | 2018-11-02 | 2023-06-06 | メルク・シャープ・アンド・ドーム・エルエルシー | Ｎａｖ１．８阻害薬としての２－アミノ－Ｎ－ヘテロアリール－ニコチンアミド類 |
| US12344595B2 (en) * | 2018-11-02 | 2025-07-01 | Merck Sharp & Dohme Llc | 2-amino-n-phenyl-nicotinamides as NAV1.8 inhibitors |
| US20230114728A1 (en) * | 2019-11-26 | 2023-04-13 | VenatoRx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| US11802122B2 (en) * | 2020-06-17 | 2023-10-31 | Merck Sharp & Dohme Llc | 2-oxoimidazolidine-4-carboxamides as NAv1.8 inhibitors |
| CN115697327A (zh) * | 2020-06-17 | 2023-02-03 | 默沙东有限责任公司 | 作为nav1.8抑制剂的5-氧代-吡咯烷-3-甲酰胺 |
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