JP2013532660A5 - - Google Patents
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- Publication number
- JP2013532660A5 JP2013532660A5 JP2013520869A JP2013520869A JP2013532660A5 JP 2013532660 A5 JP2013532660 A5 JP 2013532660A5 JP 2013520869 A JP2013520869 A JP 2013520869A JP 2013520869 A JP2013520869 A JP 2013520869A JP 2013532660 A5 JP2013532660 A5 JP 2013532660A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- alkoxy
- optionally substituted
- hydrogen
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 100
- 125000003545 alkoxy group Chemical group 0.000 claims 44
- 229910052739 hydrogen Inorganic materials 0.000 claims 40
- 239000001257 hydrogen Substances 0.000 claims 40
- 229910052736 halogen Inorganic materials 0.000 claims 38
- 150000002367 halogens Chemical class 0.000 claims 38
- 125000001424 substituent group Chemical group 0.000 claims 36
- 150000002431 hydrogen Chemical class 0.000 claims 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 28
- 125000003342 alkenyl group Chemical group 0.000 claims 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims 26
- 125000000304 alkynyl group Chemical group 0.000 claims 24
- 125000000623 heterocyclic group Chemical group 0.000 claims 24
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 20
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- -1 stereoisomers Chemical class 0.000 claims 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 150000002148 esters Chemical class 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- DITZKPGGPGEQCE-UHFFFAOYSA-N azulene-5-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC=CC2=C1 DITZKPGGPGEQCE-UHFFFAOYSA-N 0.000 claims 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- ZMGWNKLTJQXNAB-UHFFFAOYSA-N 2h-chromene-6-carboxylic acid Chemical compound O1CC=CC2=CC(C(=O)O)=CC=C21 ZMGWNKLTJQXNAB-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- WSVSRNIYZVCNIY-UHFFFAOYSA-N 7-(benzenesulfonylmethyl)-4-methyl-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound C1=2C=COC=2C(C)OC(C=2C(O)=O)=C1C=CC=2CS(=O)(=O)C1=CC=CC=C1 WSVSRNIYZVCNIY-UHFFFAOYSA-N 0.000 claims 1
- ZTKSCKSNALMGMI-UHFFFAOYSA-N 7-(benzenesulfonylmethyl)-4-oxofuro[2,3-c]chromene-6-carboxylic acid Chemical compound C1=CC=2C=3C=COC=3C(=O)OC=2C(C(=O)O)=C1CS(=O)(=O)C1=CC=CC=C1 ZTKSCKSNALMGMI-UHFFFAOYSA-N 0.000 claims 1
- YATHIMWFGWBSIT-UHFFFAOYSA-N 7-(benzenesulfonylmethyl)-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound C1=CC=2C=3C=COC=3COC=2C(C(=O)O)=C1CS(=O)(=O)C1=CC=CC=C1 YATHIMWFGWBSIT-UHFFFAOYSA-N 0.000 claims 1
- DCYRGSMTVUUKSL-UHFFFAOYSA-N 7-(benzenesulfonylmethyl)furo[2,3-c]quinoline-6-carboxylic acid Chemical compound C1=CC2=C3C=COC3=CN=C2C(C(=O)O)=C1CS(=O)(=O)C1=CC=CC=C1 DCYRGSMTVUUKSL-UHFFFAOYSA-N 0.000 claims 1
- RFPRHKPCTLCDEC-AATRIKPKSA-N 7-[[2-[(e)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical class CCN(CC)C\C=C\C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OC=C2)CO2)C2=C1C(O)=O RFPRHKPCTLCDEC-AATRIKPKSA-N 0.000 claims 1
- RFPRHKPCTLCDEC-WAYWQWQTSA-N 7-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OC=C2)CO2)C2=C1C(O)=O RFPRHKPCTLCDEC-WAYWQWQTSA-N 0.000 claims 1
- CBJSPEGLDIAGBF-ARJAWSKDSA-N 7-[[2-[(z)-3-(ethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound CCNC\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OC=C2)CO2)C2=C1C(O)=O CBJSPEGLDIAGBF-ARJAWSKDSA-N 0.000 claims 1
- CNSPMLOZLHMVQX-UHFFFAOYSA-N 7-[[2-[3-(diethylamino)propyl]-4-fluorophenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound CCN(CC)CCCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OC=C2)CO2)C2=C1C(O)=O CNSPMLOZLHMVQX-UHFFFAOYSA-N 0.000 claims 1
- QNLSUCSABPHYKA-UHFFFAOYSA-N 7-[[2-[3-(diethylamino)propyl]-4-fluorophenyl]sulfonylamino]furo[2,3-c]quinoline-6-carboxylic acid Chemical compound CCN(CC)CCCC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OC=C2)C=N2)C2=C1C(O)=O QNLSUCSABPHYKA-UHFFFAOYSA-N 0.000 claims 1
- DWXHOVUMTHMVJK-UPHRSURJSA-N 7-[[4-fluoro-2-[(z)-3-(3-hydroxyazetidin-1-yl)prop-1-enyl]phenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound C1C(O)CN1C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OC=C2)CO2)C2=C1C(O)=O DWXHOVUMTHMVJK-UPHRSURJSA-N 0.000 claims 1
- TVRQUVMDOXDPBM-NLVOMGJBSA-N 7-[[4-fluoro-2-[(z)-3-[(3r)-3-hydroxypyrrolidin-1-yl]prop-1-enyl]phenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound C1[C@H](O)CCN1C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OC=C2)CO2)C2=C1C(O)=O TVRQUVMDOXDPBM-NLVOMGJBSA-N 0.000 claims 1
- TVRQUVMDOXDPBM-YYZONTRBSA-N 7-[[4-fluoro-2-[(z)-3-[(3s)-3-hydroxypyrrolidin-1-yl]prop-1-enyl]phenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound C1[C@@H](O)CCN1C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C2=C(OC=C2)CO2)C2=C1C(O)=O TVRQUVMDOXDPBM-YYZONTRBSA-N 0.000 claims 1
- ISTCDIQUYWIORV-UPHRSURJSA-N 7-[[4-fluoro-2-[(z)-3-morpholin-4-ylprop-1-enyl]phenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound C1=CC=2C=3C=COC=3COC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=C(F)C=C1\C=C/CN1CCOCC1 ISTCDIQUYWIORV-UPHRSURJSA-N 0.000 claims 1
- WTWWMQFXEKRNCA-ARJAWSKDSA-N 7-[[4-fluoro-2-[(z)-3-pyrrolidin-1-ylprop-1-enyl]phenyl]sulfonylamino]-4h-furo[2,3-c]chromene-6-carboxylic acid Chemical compound C1=CC=2C=3C=COC=3COC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=C(F)C=C1\C=C/CN1CCCC1 WTWWMQFXEKRNCA-ARJAWSKDSA-N 0.000 claims 1
- BRPFFWNUJBVZEB-UHFFFAOYSA-N 8-(benzenesulfonylmethyl)-4,5-dihydrofuro[2,3-d][1]benzoxepine-7-carboxylic acid Chemical compound C1=CC=2C=3C=COC=3CCOC=2C(C(=O)O)=C1CS(=O)(=O)C1=CC=CC=C1 BRPFFWNUJBVZEB-UHFFFAOYSA-N 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 102000002933 Thioredoxin Human genes 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
- 125000005553 heteroaryloxy 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
- 238000001990 intravenous administration Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 229940094937 thioredoxin Drugs 0.000 claims 1
- 108060008226 thioredoxin Proteins 0.000 claims 1
- 230000004580 weight loss Effects 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36665010P | 2010-07-22 | 2010-07-22 | |
| US61/366,650 | 2010-07-22 | ||
| US201161470093P | 2011-03-31 | 2011-03-31 | |
| US61/470,093 | 2011-03-31 | ||
| PCT/US2011/044864 WO2012012642A1 (en) | 2010-07-22 | 2011-07-21 | Tricyclic compounds and methds of making and using same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013532660A JP2013532660A (ja) | 2013-08-19 |
| JP2013532660A5 true JP2013532660A5 (enExample) | 2014-09-11 |
| JP5913310B2 JP5913310B2 (ja) | 2016-04-27 |
Family
ID=44504203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013520869A Active JP5913310B2 (ja) | 2010-07-22 | 2011-07-21 | 三環式化合物ならびにその作製および使用方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9266896B2 (enExample) |
| EP (1) | EP2595988B1 (enExample) |
| JP (1) | JP5913310B2 (enExample) |
| KR (1) | KR20130043207A (enExample) |
| CN (1) | CN103249735B (enExample) |
| AU (1) | AU2011281037B2 (enExample) |
| BR (1) | BR112013001613A2 (enExample) |
| CA (1) | CA2806221A1 (enExample) |
| MX (1) | MX2013000836A (enExample) |
| WO (1) | WO2012012642A1 (enExample) |
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| WO2011127304A2 (en) | 2010-04-07 | 2011-10-13 | Zafgen Corporation | Methods of treating an overweight subject |
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| MX339201B (es) | 2010-10-12 | 2016-05-13 | Zafgen Inc | Compuestos de sulfonamida y métodos para elaborarlos y usarlos. |
| 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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2011
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- 2011-07-21 EP EP11741370.8A patent/EP2595988B1/en active Active
- 2011-07-21 AU AU2011281037A patent/AU2011281037B2/en not_active Ceased
- 2011-07-21 CN CN201180045319.0A patent/CN103249735B/zh not_active Expired - Fee Related
- 2011-07-21 WO PCT/US2011/044864 patent/WO2012012642A1/en not_active Ceased
- 2011-07-21 JP JP2013520869A patent/JP5913310B2/ja active Active
- 2011-07-21 CA CA2806221A patent/CA2806221A1/en not_active Abandoned
- 2011-07-21 MX MX2013000836A patent/MX2013000836A/es active IP Right Grant
- 2011-07-21 KR KR1020137004371A patent/KR20130043207A/ko not_active Withdrawn
- 2011-07-21 US US13/811,453 patent/US9266896B2/en not_active Expired - Fee Related
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2016
- 2016-01-07 US US14/990,299 patent/US9839623B2/en not_active Expired - Fee Related
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