JP2018522929A5 - - Google Patents
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- JP2018522929A5 JP2018522929A5 JP2018507023A JP2018507023A JP2018522929A5 JP 2018522929 A5 JP2018522929 A5 JP 2018522929A5 JP 2018507023 A JP2018507023 A JP 2018507023A JP 2018507023 A JP2018507023 A JP 2018507023A JP 2018522929 A5 JP2018522929 A5 JP 2018522929A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxaspiro
- methoxy
- carboxylate
- octane
- 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.)
- Withdrawn
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- -1 cyano, hydroxyl Chemical group 0.000 claims 125
- 125000000217 alkyl group Chemical group 0.000 claims 55
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 13
- 125000004269 oxiran-2-yl group Chemical group [H]C1([H])OC1([H])* 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000002619 bicyclic group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 125000000304 alkynyl group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 238000001990 intravenous administration Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 238000007920 subcutaneous administration Methods 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims 1
- WYCKMHZYHOJRAU-UHFFFAOYSA-N 3-(azetidin-3-yl)-1,1-dioxo-1,4-thiazinane-4-carboxylic acid Chemical compound C1CS(=O)(=O)CC(N1C(=O)O)C2CNC2 WYCKMHZYHOJRAU-UHFFFAOYSA-N 0.000 claims 1
- 241000282326 Felis catus Species 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 102000002933 Thioredoxin Human genes 0.000 claims 1
- RVAGWUOXLQRFMX-KBZWHEKBSA-N [(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] 3-[2-(diethylamino)ethyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C(C)N(CCC1(CN(C1)C(=O)O[C@H]1[C@H]([C@@H]([C@@]2(CO2)CC1)[C@]1(O[C@@H]1CC=C(C)C)C)OC)O)CC RVAGWUOXLQRFMX-KBZWHEKBSA-N 0.000 claims 1
- VALHXFSMKXJNKS-RYGARLMKSA-N [(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl] 3-[3-(diethylamino)propyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C(C)N(CCCC1(CN(C1)C(=O)O[C@H]1[C@H]([C@@H]([C@@]2(CO2)CC1)[C@]1(O[C@@H]1CC=C(C)C)C)OC)O)CC VALHXFSMKXJNKS-RYGARLMKSA-N 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- MOHUSCGYTXUGCG-UHFFFAOYSA-N azetidin-3-yl 4-(2,2-difluoroethyl)piperazine-1-carboxylate Chemical compound FC(F)CN1CCN(CC1)C(=O)OC1CNC1 MOHUSCGYTXUGCG-UHFFFAOYSA-N 0.000 claims 1
- KXFIATKHODRPOS-UHFFFAOYSA-N azetidin-3-yl 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1CNC1 KXFIATKHODRPOS-UHFFFAOYSA-N 0.000 claims 1
- WHKQMKGNVOKTSO-UHFFFAOYSA-N azetidin-3-yl morpholine-4-carboxylate Chemical compound C1COCCN1C(=O)OC1CNC1 WHKQMKGNVOKTSO-UHFFFAOYSA-N 0.000 claims 1
- LJGRJKAFORAQOU-UHFFFAOYSA-N azetidine-1-carbonyl azetidine-1-carboxylate Chemical compound C1CCN1C(=O)OC(=O)N1CCC1 LJGRJKAFORAQOU-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 229940094937 thioredoxin Drugs 0.000 claims 1
- 108060008226 thioredoxin Proteins 0.000 claims 1
- 230000004584 weight gain Effects 0.000 claims 1
- 235000019786 weight gain Nutrition 0.000 claims 1
- 230000004580 weight loss Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562203742P | 2015-08-11 | 2015-08-11 | |
| US62/203,742 | 2015-08-11 | ||
| PCT/US2016/046511 WO2017027684A1 (en) | 2015-08-11 | 2016-08-11 | Fumagillol heterocyclic compounds and methods of making and using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018522929A JP2018522929A (ja) | 2018-08-16 |
| JP2018522929A5 true JP2018522929A5 (pt-PT) | 2019-08-29 |
Family
ID=56799580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018507023A Withdrawn JP2018522929A (ja) | 2015-08-11 | 2016-08-11 | フマギロール複素環化合物ならびにその作製および使用方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (5) | US20180230137A1 (pt-PT) |
| EP (1) | EP3334728A1 (pt-PT) |
| JP (1) | JP2018522929A (pt-PT) |
| KR (1) | KR20180035907A (pt-PT) |
| CN (1) | CN108026085A (pt-PT) |
| AR (1) | AR105671A1 (pt-PT) |
| AU (1) | AU2016306558A1 (pt-PT) |
| CA (1) | CA2995366A1 (pt-PT) |
| EA (1) | EA201890449A1 (pt-PT) |
| IL (1) | IL257443A (pt-PT) |
| MA (1) | MA42612A (pt-PT) |
| MX (1) | MX2018001733A (pt-PT) |
| PH (1) | PH12018500315A1 (pt-PT) |
| TW (1) | TW201718550A (pt-PT) |
| WO (1) | WO2017027684A1 (pt-PT) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013169860A1 (en) | 2012-05-09 | 2013-11-14 | Zafgen, Inc. | Fumigillol type compounds and methods of making and using same |
| AR105671A1 (es) * | 2015-08-11 | 2017-10-25 | Zafgen Inc | Compuestos heterocíclicos de fumagillol y sus métodos de elaboración y uso |
| CN106432255A (zh) | 2015-08-11 | 2017-02-22 | 扎夫根公司 | 烟曲霉素醇螺环化合物和制备和使用其的方法 |
| WO2018148638A1 (en) * | 2017-02-10 | 2018-08-16 | Zafgen, Inc. | Pharmaceutical compositions of metap-2 inhibitors |
| WO2019118612A1 (en) * | 2017-12-12 | 2019-06-20 | Zafgen, Inc. | Targeting compounds |
| WO2019173505A1 (en) * | 2018-03-06 | 2019-09-12 | Zafgen, Inc. | Methods of treating disorders related to glycemic control |
| CN109180551A (zh) * | 2018-07-17 | 2019-01-11 | 宜春学院 | 一种四元氮杂环中间体的制备方法 |
| JP2022512826A (ja) | 2018-10-26 | 2022-02-07 | シンデブルックス，インコーポレイティド | ＭｅｔＡＰ２阻害剤のバイオマーカーとその応用 |
| CN111606836B (zh) * | 2020-06-12 | 2021-01-15 | 上海馨远医药科技有限公司 | 一种R-N-Boc-3-吡咯烷乙酸的制备方法 |
| GB202011996D0 (en) | 2020-07-31 | 2020-09-16 | Adorx Therapeutics Ltd | Antagonist compounds |
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| JP2013543899A (ja) | 2010-11-29 | 2013-12-09 | ザフゲン，インコーポレイテッド | ６−ｏ−（４−ジメチルアミノエトキシ）シンナモイルフマギロールの非連日投与を用いた肥満の治療 |
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-
2016
- 2016-08-10 AR ARP160102461A patent/AR105671A1/es unknown
- 2016-08-11 CA CA2995366A patent/CA2995366A1/en not_active Abandoned
- 2016-08-11 JP JP2018507023A patent/JP2018522929A/ja not_active Withdrawn
- 2016-08-11 KR KR1020187006637A patent/KR20180035907A/ko unknown
- 2016-08-11 US US15/752,000 patent/US20180230137A1/en not_active Abandoned
- 2016-08-11 MA MA042612A patent/MA42612A/fr unknown
- 2016-08-11 TW TW105125677A patent/TW201718550A/zh unknown
- 2016-08-11 MX MX2018001733A patent/MX2018001733A/es unknown
- 2016-08-11 EA EA201890449A patent/EA201890449A1/ru unknown
- 2016-08-11 EP EP16756874.0A patent/EP3334728A1/en not_active Withdrawn
- 2016-08-11 AU AU2016306558A patent/AU2016306558A1/en not_active Abandoned
- 2016-08-11 WO PCT/US2016/046511 patent/WO2017027684A1/en active Application Filing
- 2016-08-11 CN CN201680054518.0A patent/CN108026085A/zh active Pending
- 2016-11-17 US US15/354,834 patent/US9682965B2/en not_active Expired - Fee Related
-
2017
- 2017-05-16 US US15/596,512 patent/US10023561B2/en not_active Expired - Fee Related
-
2018
- 2018-02-08 IL IL257443A patent/IL257443A/en unknown
- 2018-02-12 PH PH12018500315A patent/PH12018500315A1/en unknown
- 2018-11-20 US US16/196,458 patent/US20190084969A1/en not_active Abandoned
- 2018-11-20 US US16/196,448 patent/US20190084968A1/en not_active Abandoned
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