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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| MX2023013147A (es) * | 2021-05-07 | 2023-11-28 | Merck Sharp & Dohme Llc | Aril 3-oxopiperazin carboxamidas y heteroaril 3-oxopiperazin carboxamidas como inhibidores de nav1.8. |
| JP2025513452A (ja) | 2022-04-22 | 2025-04-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | 疼痛の治療のためのヘテロアリール化合物 |
| UY40234A (es) | 2022-04-22 | 2023-11-15 | Vertex Pharma | Compuestos heteroarilo para el tratamiento del dolor |
| AU2023257313A1 (en) | 2022-04-22 | 2024-10-31 | Vertex Pharmaceuticals Incorporated | Heteroaryl compounds for the treatment of pain |
| GEAP202516634A (en) | 2022-04-22 | 2025-02-25 | Vertex Pharma | Heteroaryl compounds for the treatment of pain |
| AU2023391870A1 (en) | 2022-12-06 | 2025-06-05 | Vertex Pharmaceuticals Incorporated | Process for the synthesis of substituted tetrahydrofuran modulators of sodium channels |
| TW202523312A (zh) * | 2023-10-16 | 2025-06-16 | 美商克洛諾斯生技有限公司 | 離胺酸乙醯基轉移酶抑制劑 |
| 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 |
| 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 |
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| JPS52122392A (en) * | 1976-04-07 | 1977-10-14 | Sangyo Kagaku Kenkyu Kyokai | Novel antibacterials |
| EP1723129A1 (en) * | 2003-12-18 | 2006-11-22 | Cv Therapeutics, Inc. | 1-akan-2-ol substituted piperazine and piperidine compounds |
| CN101883760A (zh) | 2007-10-11 | 2010-11-10 | 沃泰克斯药物股份有限公司 | 用作电压-门控钠通道抑制剂的杂芳基酰胺类 |
| CA2702101A1 (en) | 2007-10-11 | 2009-04-16 | Vertex Pharmaceuticals Incorporated | Aryl amides useful as inhibitors of voltage-gated sodium channels |
| AU2008310661A1 (en) | 2007-10-11 | 2009-04-16 | Vertex Pharmaceuticals Incorporated | 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 |
| AU2014212431B2 (en) | 2013-01-31 | 2018-04-05 | Vertex Pharmaceuticals Incorporated | Amides as modulators of sodium channels |
| KR102295748B1 (ko) | 2013-01-31 | 2021-09-01 | 버텍스 파마슈티칼스 인코포레이티드 | 나트륨 채널의 조절제로서의 피리돈 아미드 |
| CN105073738B (zh) | 2013-01-31 | 2018-01-05 | 沃泰克斯药物股份有限公司 | 作为钠通道调节剂的喹啉及喹喔啉酰胺类 |
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| LT3080134T (lt) | 2013-12-13 | 2018-11-12 | Vertex Pharmaceuticals Incorporated | Piridono amidų provaistai, naudotini kaip natrio kanalų moduliatoriai |
| 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 |
| KR101844984B1 (ko) | 2016-05-31 | 2018-04-03 | 한림대학교 산학협력단 | 5원 헤테로사이클릭 유도체, 이의 제조방법 및 이를 포함하는 약제학적 조성물 |
| US11358977B2 (en) | 2017-05-16 | 2022-06-14 | Vertex Pharmaceuticals Incorporated | Deuterated pyridone amides and prodrugs thereof as modulators of sodium channels |
| SG11202000230VA (en) | 2017-07-11 | 2020-02-27 | Vertex Pharma | Carboxamides as modulators of sodium channels |
| AU2018371216B2 (en) * | 2017-11-23 | 2024-09-19 | Oslo University Hospital Hf | Treatment of tachycardia |
| WO2019226931A1 (en) * | 2018-05-25 | 2019-11-28 | VenatoRx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| WO2020092187A1 (en) * | 2018-11-02 | 2020-05-07 | Merck Sharp & Dohme Corp. | 2-amino-n-phenyl-nicotinamides as nav1.8 inhibitors |
| EP3873893A1 (en) * | 2018-11-02 | 2021-09-08 | Merck Sharp & Dohme Corp. | 2-amino-n-heteroaryl-nicotinamides as nav1.8 inhibitors |
| US20230114728A1 (en) * | 2019-11-26 | 2023-04-13 | VenatoRx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| BR112022024476A2 (pt) * | 2020-06-17 | 2022-12-27 | Merck Sharp & Dohme Llc | 5-oxopirrolidino-3-carboxamidas como inibidores de nav1.8 |
| GEP20257750B (en) * | 2020-06-17 | 2025-03-25 | Merck Sharp & Dohme Llc | 2-oxoimidazolidine-4-carboxamides as nav1.8 inhibitors |
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