JP2020535127A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020535127A5 JP2020535127A5 JP2020515942A JP2020515942A JP2020535127A5 JP 2020535127 A5 JP2020535127 A5 JP 2020535127A5 JP 2020515942 A JP2020515942 A JP 2020515942A JP 2020515942 A JP2020515942 A JP 2020515942A JP 2020535127 A5 JP2020535127 A5 JP 2020535127A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfonamide
- oxadiazole
- dimethylcyclopropyl
- alkyl
- pyridin
- 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
- -1 NR 7 R 8 Chemical group 0.000 claims 49
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 claims 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 claims 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- RHUCEFXXFYPRCA-VXGBXAGGSA-N 2-[(1S,3S)-2,2-dimethyl-3-(3-phenyl-1,2,4-oxadiazol-5-yl)cyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound C1=CC=CC=C1C=1N=C([C@H]2[C@H](C3=NC=C(S(=O)(=O)N)S3)C2(C)C)ON=1 RHUCEFXXFYPRCA-VXGBXAGGSA-N 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 229930194542 Keto Natural products 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000000468 ketone group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- ZURYJDDVGAOKKK-NXEZZACHSA-N 2-[(1R,2R)-2-(3-phenyl-1,2,4-oxadiazol-5-yl)cyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound C1(=CC=CC=C1)C1=NOC(=N1)[C@H]1[C@@H](C1)C=1SC(=CN=1)S(=O)(=O)N ZURYJDDVGAOKKK-NXEZZACHSA-N 0.000 claims 1
- RHUCEFXXFYPRCA-RYUDHWBXSA-N 2-[(1R,3R)-2,2-dimethyl-3-(3-phenyl-1,2,4-oxadiazol-5-yl)cyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound CC1(C)[C@@H]([C@H]1C1=NC=C(S1)S(N)(=O)=O)C1=NC(=NO1)C1=CC=CC=C1 RHUCEFXXFYPRCA-RYUDHWBXSA-N 0.000 claims 1
- HXBPPHLXYXHCAC-RKDXNWHRSA-N 2-[(1S,3S)-2,2-dimethyl-3-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)cyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound CC1([C@H]([C@@H]1C1=NC(=NO1)C(C)C)C=1SC(=CN=1)S(=O)(=O)N)C HXBPPHLXYXHCAC-RKDXNWHRSA-N 0.000 claims 1
- GNPKHWGYXFNRSK-VXGBXAGGSA-N 2-[(1S,3S)-3-(1,3-benzoxazol-2-yl)-2,2-dimethylcyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound O1C(=NC2=C1C=CC=C2)[C@@H]1C([C@H]1C=1SC(=CN=1)S(=O)(=O)N)(C)C GNPKHWGYXFNRSK-VXGBXAGGSA-N 0.000 claims 1
- XLPXQBROYKPTPZ-NXEZZACHSA-N 2-[(1S,3S)-3-(3-cyclobutyl-1,2,4-oxadiazol-5-yl)-2,2-dimethylcyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound C1(CCC1)C1=NOC(=N1)[C@@H]1C([C@H]1C=1SC(=CN=1)S(=O)(=O)N)(C)C XLPXQBROYKPTPZ-NXEZZACHSA-N 0.000 claims 1
- DZGGJEJBNFZMBV-RKDXNWHRSA-N 2-[(1S,3S)-3-[3-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-5-yl]-2,2-dimethylcyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound FC1(CC(C1)C1=NOC(=N1)[C@@H]1C([C@H]1C=1SC(=CN=1)S(=O)(=O)N)(C)C)F DZGGJEJBNFZMBV-RKDXNWHRSA-N 0.000 claims 1
- FWNBKMNABVPWPR-CHWSQXEVSA-N 2-[(1S,3S)-3-[3-(5-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]-2,2-dimethylcyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound ClC=1C=CC(=C(C=1)C1=NOC(=N1)[C@@H]1C([C@H]1C=1SC(=CN=1)S(=O)(=O)N)(C)C)OC FWNBKMNABVPWPR-CHWSQXEVSA-N 0.000 claims 1
- NXBOTBFWHAYCJM-GHMZBOCLSA-N 2-[(1S,3S)-3-[3-(5-fluoropyridin-3-yl)-1,2,4-oxadiazol-5-yl]-2,2-dimethylcyclopropyl]-1,3-thiazole-5-sulfonamide Chemical compound FC=1C=C(C=NC=1)C1=NOC(=N1)[C@@H]1C([C@H]1C=1SC(=CN=1)S(=O)(=O)N)(C)C NXBOTBFWHAYCJM-GHMZBOCLSA-N 0.000 claims 1
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- 102000010909 Monoamine Oxidase Human genes 0.000 claims 1
- 108010062431 Monoamine oxidase Proteins 0.000 claims 1
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims 1
- 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 claims 1
- 108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 claims 1
- 239000000164 antipsychotic agent Substances 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 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 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 229960004502 levodopa Drugs 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 1
- HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762560444P | 2017-09-19 | 2017-09-19 | |
| US62/560,444 | 2017-09-19 | ||
| PCT/US2018/050975 WO2019060210A1 (en) | 2017-09-19 | 2018-09-14 | HETEROARYLIC ALLOSTERIC MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020535127A JP2020535127A (ja) | 2020-12-03 |
| JP2020535127A5 true JP2020535127A5 (enExample) | 2021-10-21 |
| JP7221944B2 JP7221944B2 (ja) | 2023-02-14 |
Family
ID=65811090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020515942A Active JP7221944B2 (ja) | 2017-09-19 | 2018-09-14 | ニコチン性アセチルコリン受容体のヘテロアリールアロステリックモジュレーター |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11198687B2 (enExample) |
| EP (1) | EP3684357B1 (enExample) |
| JP (1) | JP7221944B2 (enExample) |
| CN (1) | CN111107846A (enExample) |
| CA (1) | CA3073212A1 (enExample) |
| WO (1) | WO2019060210A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11512092B2 (en) * | 2015-10-16 | 2022-11-29 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof |
| US11780848B2 (en) * | 2015-10-16 | 2023-10-10 | Abbvie Inc. | Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1- carboxamide and solid state forms thereof |
| US10357493B2 (en) | 2017-03-10 | 2019-07-23 | Selenity Therapeutics (Bermuda), Ltd. | Metalloenzyme inhibitor compounds |
| CN114727974A (zh) | 2019-07-30 | 2022-07-08 | 艾科尼佐治疗股份有限公司 | Hdac6抑制剂及其用途 |
| WO2022169985A1 (en) | 2021-02-03 | 2022-08-11 | Eikonizo Therapeutics, Inc. | Hdac6 inhibitors and uses thereof |
| AU2023250964A1 (en) | 2022-04-08 | 2024-11-07 | Eikonizo Therapeutics, Inc. | Oxadiazole hdac6 inhibitors and uses thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5585388A (en) * | 1995-04-07 | 1996-12-17 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acetylcholine receptors |
| WO2010122082A1 (en) | 2009-04-25 | 2010-10-28 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| AU2012212393B2 (en) | 2011-02-02 | 2015-06-11 | Bionomics Limited | Positive allosteric modulators of the alpha 7 nicotinic acetylcholine receptor and uses thereof. |
| EP2888229B1 (en) | 2012-08-01 | 2019-02-06 | Merck Sharp & Dohme Corp. | alpha7 NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS AND USES THEREOF |
| WO2015191799A1 (en) | 2014-06-13 | 2015-12-17 | Merck Sharp & Dohme Corp. | Alpha-7 nicotinic acetylcholine receptor modulators and uses thereof |
| US9840481B2 (en) * | 2016-03-22 | 2017-12-12 | Merck Sharp & Dohme Corp. | Allosteric modulators of nicotinic acetylcholine receptors |
-
2018
- 2018-09-14 WO PCT/US2018/050975 patent/WO2019060210A1/en not_active Ceased
- 2018-09-14 CA CA3073212A patent/CA3073212A1/en active Pending
- 2018-09-14 US US16/646,616 patent/US11198687B2/en active Active
- 2018-09-14 JP JP2020515942A patent/JP7221944B2/ja active Active
- 2018-09-14 EP EP18859614.2A patent/EP3684357B1/en active Active
- 2018-09-14 CN CN201880060672.8A patent/CN111107846A/zh active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20211960T1 (hr) | Alosterični modulatori nikotinskih acetilcolinskih receptora | |
| JP2017508766A5 (enExample) | ||
| JP2018536671A5 (enExample) | ||
| JP2008523041A5 (enExample) | ||
| JP2014525444A5 (enExample) | ||
| JP2017506237A5 (enExample) | ||
| JP2017512786A5 (enExample) | ||
| JP2010533158A5 (enExample) | ||
| JP2010513283A (ja) | 新規なオキサジアゾール化合物 | |
| JP2016523911A5 (enExample) | ||
| JP2009524670A5 (enExample) | ||
| JP2017538750A5 (enExample) | ||
| RU2017125520A (ru) | Соединения, ингибирующие parg | |
| JP2017537948A5 (enExample) | ||
| JP2008513514A5 (enExample) | ||
| JP2013517264A5 (enExample) | ||
| JP2014513122A5 (enExample) | ||
| RU2017121044A (ru) | Производные амидотиадиазола в качестве ингибиторов надфн-оксидазы | |
| JP2017512794A5 (enExample) | ||
| JP2013519680A5 (enExample) | ||
| JP2013519724A5 (enExample) | ||
| JP2010540462A5 (enExample) | ||
| JP2017509676A5 (enExample) | ||
| JP2018507234A5 (enExample) | ||
| JP2020512401A5 (enExample) |