JPWO2022009863A5 - - Google Patents
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- Publication number
- JPWO2022009863A5 JPWO2022009863A5 JP2022535331A JP2022535331A JPWO2022009863A5 JP WO2022009863 A5 JPWO2022009863 A5 JP WO2022009863A5 JP 2022535331 A JP2022535331 A JP 2022535331A JP 2022535331 A JP2022535331 A JP 2022535331A JP WO2022009863 A5 JPWO2022009863 A5 JP WO2022009863A5
- Authority
- JP
- Japan
- Prior art keywords
- alkoxy
- group
- cycloalkyl
- alkyl
- halogen
- 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.)
- Granted
Links
- 125000003545 alkoxy group Chemical group 0.000 claims 55
- 125000000217 alkyl group Chemical group 0.000 claims 51
- 125000001424 substituent group Chemical group 0.000 claims 43
- 229910052736 halogen Inorganic materials 0.000 claims 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 34
- 150000003839 salts Chemical class 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 27
- 235000019000 fluorine Nutrition 0.000 claims 22
- 229910052731 fluorine Inorganic materials 0.000 claims 20
- 239000011737 fluorine Substances 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- ZHTBYMQLXFJLJU-ZCFIWIBFSA-N (1R)-1-(1,2-benzoxazol-3-yl)ethanesulfonamide Chemical compound C[C@H](C1=NOC2=C1C=CC=C2)S(N)(=O)=O ZHTBYMQLXFJLJU-ZCFIWIBFSA-N 0.000 claims 8
- -1 2-(methoxycarbonyl)ethyl Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 7
- ZHTBYMQLXFJLJU-LURJTMIESA-N (1S)-1-(1,2-benzoxazol-3-yl)ethanesulfonamide Chemical compound C[C@@H](C1=NOC2=C1C=CC=C2)S(N)(=O)=O ZHTBYMQLXFJLJU-LURJTMIESA-N 0.000 claims 4
- ZHTBYMQLXFJLJU-UHFFFAOYSA-N 1-(1,2-benzoxazol-3-yl)ethanesulfonamide Chemical compound CC(C1=NOC2=CC=CC=C12)S(N)(=O)=O ZHTBYMQLXFJLJU-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- FHEGLMBNFCJNPX-UHFFFAOYSA-N 1-(1,2-benzoxazol-3-yl)cyclopropane-1-sulfonamide Chemical compound NS(C1(CC1)C1=NOC2=CC=CC=C12)(=O)=O FHEGLMBNFCJNPX-UHFFFAOYSA-N 0.000 claims 3
- YCMXREADMZLPSV-UHFFFAOYSA-N 2-(1,2-benzoxazol-3-yl)propane-2-sulfonamide Chemical compound CC(C)(C1=NOC2=C1C=CC=C2)S(N)(=O)=O YCMXREADMZLPSV-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- TYYLNWPZUCPEEB-UHFFFAOYSA-N 1,2-benzoxazol-3-yl(difluoro)methanesulfonamide Chemical compound NS(C(C1=NOC2=C1C=CC=C2)(F)F)(=O)=O TYYLNWPZUCPEEB-UHFFFAOYSA-N 0.000 claims 2
- PMDHGSUOYIDYMQ-UHFFFAOYSA-N 1,2-benzoxazol-3-yl(fluoro)methanesulfonamide Chemical compound NS(C(C1=NOC2=C1C=CC=C2)F)(=O)=O PMDHGSUOYIDYMQ-UHFFFAOYSA-N 0.000 claims 2
- RRMBFTGQLYDZHK-UHFFFAOYSA-N 1-(1,2-benzoxazol-3-yl)-1-fluoroethanesulfonamide Chemical compound CC(C1=NOC2=C1C=CC=C2)(F)S(N)(=O)=O RRMBFTGQLYDZHK-UHFFFAOYSA-N 0.000 claims 2
- 108090000604 Hydrolases Proteins 0.000 claims 2
- 102000004157 Hydrolases Human genes 0.000 claims 2
- 108090001060 Lipase Proteins 0.000 claims 2
- 239000004367 Lipase Substances 0.000 claims 2
- 102000004882 Lipase Human genes 0.000 claims 2
- 102000004316 Oxidoreductases Human genes 0.000 claims 2
- 108090000854 Oxidoreductases Proteins 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 235000019421 lipase Nutrition 0.000 claims 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- BKOAVHXSTFZICY-UHFFFAOYSA-N 1-(1,2-benzoxazol-3-yl)-2-methylpropane-1-sulfonamide Chemical compound CC(C)C(C1=NOC2=C1C=CC=C2)S(N)(=O)=O BKOAVHXSTFZICY-UHFFFAOYSA-N 0.000 claims 1
- VWYMVLOOXKNKLL-UHFFFAOYSA-N 1-(1,2-benzoxazol-3-yl)butane-1-sulfonamide Chemical compound CCCC(C1=NOC2=CC=CC=C12)S(N)(=O)=O VWYMVLOOXKNKLL-UHFFFAOYSA-N 0.000 claims 1
- VKDABBHGNIVCFZ-UHFFFAOYSA-N 1-(1,2-benzoxazol-3-yl)propane-1-sulfonamide Chemical compound CCC(C1=NOC2=CC=CC=C12)S(N)(=O)=O VKDABBHGNIVCFZ-UHFFFAOYSA-N 0.000 claims 1
- FMGYNNQFTHMFNZ-UHFFFAOYSA-N 1-(5-chloro-1,2-benzoxazol-3-yl)ethanesulfonamide Chemical compound CC(C1=NOC(C=C2)=C1C=C2Cl)S(N)(=O)=O FMGYNNQFTHMFNZ-UHFFFAOYSA-N 0.000 claims 1
- CEUSJVLQZCKLHZ-UHFFFAOYSA-N 1-(5-fluoro-1,2-benzoxazol-3-yl)ethanesulfonamide Chemical compound CC(C(C1=C2)=NOC1=CC=C2F)S(N)(=O)=O CEUSJVLQZCKLHZ-UHFFFAOYSA-N 0.000 claims 1
- TUXHCOBXHDRTQX-UHFFFAOYSA-N 1-(5-methoxy-1,2-benzoxazol-3-yl)ethanesulfonamide Chemical compound CC(C(C1=C2)=NOC1=CC=C2OC)S(N)(=O)=O TUXHCOBXHDRTQX-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 102000005751 Alcohol Oxidoreductases Human genes 0.000 claims 1
- 108010031132 Alcohol Oxidoreductases Proteins 0.000 claims 1
- 102000007698 Alcohol dehydrogenase Human genes 0.000 claims 1
- 108010021809 Alcohol dehydrogenase Proteins 0.000 claims 1
- 108700023418 Amidases Proteins 0.000 claims 1
- 108090000371 Esterases Proteins 0.000 claims 1
- 108091005804 Peptidases Proteins 0.000 claims 1
- 239000004365 Protease Substances 0.000 claims 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 1
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 claims 1
- 102000005922 amidase Human genes 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000005515 coenzyme Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical class [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020117236 | 2020-07-07 | ||
| JP2020117236 | 2020-07-07 | ||
| PCT/JP2021/025403 WO2022009863A1 (ja) | 2020-07-07 | 2021-07-06 | ベンゾイソキサゾール誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2022009863A1 JPWO2022009863A1 (https=) | 2022-01-13 |
| JPWO2022009863A5 true JPWO2022009863A5 (https=) | 2023-02-24 |
| JP7326624B2 JP7326624B2 (ja) | 2023-08-15 |
Family
ID=79553142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022535331A Active JP7326624B2 (ja) | 2020-07-07 | 2021-07-06 | ベンゾイソキサゾール誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US12534442B2 (https=) |
| EP (1) | EP4180090A4 (https=) |
| JP (1) | JP7326624B2 (https=) |
| KR (1) | KR20230035592A (https=) |
| CN (1) | CN115836058A (https=) |
| AU (1) | AU2021303974A1 (https=) |
| BR (1) | BR112022024340A2 (https=) |
| CA (1) | CA3183354A1 (https=) |
| MX (1) | MX2023000437A (https=) |
| TW (1) | TW202214580A (https=) |
| WO (1) | WO2022009863A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7324953B2 (ja) * | 2022-01-12 | 2023-08-10 | 住友ファーマ株式会社 | ベンゾイソキサゾール誘導体を含有する医薬組成物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6033114B2 (ja) | 1976-12-16 | 1985-08-01 | 大日本製薬株式会社 | １，２−ベンズイソキサゾ−ル誘導体 |
| US4172896A (en) | 1978-06-05 | 1979-10-30 | Dainippon Pharmaceutical Co., Ltd. | Methane-sulfonamide derivatives, the preparation thereof and composition comprising the same |
| JPH037226A (ja) * | 1989-03-24 | 1991-01-14 | Dainippon Pharmaceut Co Ltd | 虚血性脳障害治療薬 |
| TW253885B (https=) | 1992-12-15 | 1995-08-11 | Ishihara Sangyo Kaisha | |
| ES2244103T3 (es) * | 1997-12-26 | 2005-12-01 | Dainippon Pharmaceutical Co., Ltd. | Remedio para enfermedades neurodegenerativas. |
| WO2001019321A2 (en) | 1999-09-15 | 2001-03-22 | Elan Pharmaceuticals, Inc. | Methods for treating neuropathic pain using hetreoarylmethanesulfonamides |
| HK1252796A1 (en) | 2015-09-30 | 2019-06-06 | National University Corporation Nagoya University | Therapeutic agent and/or prophylactic agent for peripheral nerve disorder or spinal injury |
| CN106810507B (zh) | 2017-01-23 | 2019-06-21 | 珠海市海瑞德生物科技有限公司 | 一种唑尼沙胺的绿色环保合成方法 |
-
2021
- 2021-07-06 AU AU2021303974A patent/AU2021303974A1/en active Pending
- 2021-07-06 KR KR1020237003716A patent/KR20230035592A/ko active Pending
- 2021-07-06 TW TW110124806A patent/TW202214580A/zh unknown
- 2021-07-06 CA CA3183354A patent/CA3183354A1/en active Pending
- 2021-07-06 BR BR112022024340A patent/BR112022024340A2/pt unknown
- 2021-07-06 JP JP2022535331A patent/JP7326624B2/ja active Active
- 2021-07-06 WO PCT/JP2021/025403 patent/WO2022009863A1/ja not_active Ceased
- 2021-07-06 US US17/623,527 patent/US12534442B2/en active Active
- 2021-07-06 EP EP21837914.7A patent/EP4180090A4/en active Pending
- 2021-07-06 CN CN202180048407.XA patent/CN115836058A/zh active Pending
- 2021-07-06 MX MX2023000437A patent/MX2023000437A/es unknown
-
2022
- 2022-03-22 US US17/701,539 patent/US11535599B2/en active Active
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