JP2013539789A5 - - Google Patents
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- Publication number
- JP2013539789A5 JP2013539789A5 JP2013533977A JP2013533977A JP2013539789A5 JP 2013539789 A5 JP2013539789 A5 JP 2013539789A5 JP 2013533977 A JP2013533977 A JP 2013533977A JP 2013533977 A JP2013533977 A JP 2013533977A JP 2013539789 A5 JP2013539789 A5 JP 2013539789A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carboxylic acid
- thiophene
- tetrahydrobenzo
- cycloalkyl
- 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 28
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 10
- -1 stereoisomer Chemical class 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- JDAMMUGFNLFYTD-UHFFFAOYSA-N 2-(benzenesulfonamido)-1-benzothiophene-3-carboxylic acid Chemical compound S1C2=CC=CC=C2C(C(=O)O)=C1NS(=O)(=O)C1=CC=CC=C1 JDAMMUGFNLFYTD-UHFFFAOYSA-N 0.000 claims 1
- SZZBTIDMQMDKLP-UHFFFAOYSA-N 2-(benzenesulfonamido)-1-methyl-4,5,6,7-tetrahydroindole-3-carboxylic acid Chemical compound CN1C=2CCCCC=2C(C(O)=O)=C1NS(=O)(=O)C1=CC=CC=C1 SZZBTIDMQMDKLP-UHFFFAOYSA-N 0.000 claims 1
- NMXSKHSYRYPTHD-UHFFFAOYSA-N 2-(benzenesulfonamido)-3,4-dihydro-2h-thieno[2,3-b]pyran-5-carboxylic acid Chemical compound C1CC=2C(C(=O)O)=CSC=2OC1NS(=O)(=O)C1=CC=CC=C1 NMXSKHSYRYPTHD-UHFFFAOYSA-N 0.000 claims 1
- UWCRPWYGSNLEGS-UHFFFAOYSA-N 2-(benzenesulfonamido)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound S1C=2CCCCC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=CC=C1 UWCRPWYGSNLEGS-UHFFFAOYSA-N 0.000 claims 1
- SRUSMXLWNMHZDJ-UHFFFAOYSA-N 2-(benzenesulfonamido)-4-methyl-5-phenylthiophene-3-carboxylic acid Chemical compound OC(=O)C=1C(C)=C(C=2C=CC=CC=2)SC=1NS(=O)(=O)C1=CC=CC=C1 SRUSMXLWNMHZDJ-UHFFFAOYSA-N 0.000 claims 1
- IJAGTJREJGBDSR-UHFFFAOYSA-N 2-(benzenesulfonamido)-5,5-dimethyl-6,7-dihydro-4h-1-benzothiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=2CC(C)(C)CCC=2SC=1NS(=O)(=O)C1=CC=CC=C1 IJAGTJREJGBDSR-UHFFFAOYSA-N 0.000 claims 1
- BRNNPTSZGQFWIE-UHFFFAOYSA-N 2-(benzenesulfonamido)-5,6-dihydro-4h-cyclopenta[b]thiophene-3-carboxylic acid Chemical compound S1C=2CCCC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=CC=C1 BRNNPTSZGQFWIE-UHFFFAOYSA-N 0.000 claims 1
- SLCSSQUGCNIAPB-UHFFFAOYSA-N 2-(benzenesulfonamido)-5,7-dihydro-4h-thieno[2,3-c]pyran-3-carboxylic acid Chemical compound S1C=2COCCC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=CC=C1 SLCSSQUGCNIAPB-UHFFFAOYSA-N 0.000 claims 1
- ZGGDNCRGMVLIHW-UHFFFAOYSA-N 2-(benzenesulfonamido)-5-ethyl-4-methylthiophene-3-carboxylic acid Chemical compound CC1=C(CC)SC(NS(=O)(=O)C=2C=CC=CC=2)=C1C(O)=O ZGGDNCRGMVLIHW-UHFFFAOYSA-N 0.000 claims 1
- RGASJVRJBXLDPF-UHFFFAOYSA-N 2-(benzenesulfonamido)-5-ethyl-4-propan-2-ylthiophene-3-carboxylic acid Chemical compound CC(C)C1=C(CC)SC(NS(=O)(=O)C=2C=CC=CC=2)=C1C(O)=O RGASJVRJBXLDPF-UHFFFAOYSA-N 0.000 claims 1
- PYUUNGQMZIAFGY-UHFFFAOYSA-N 2-(benzenesulfonamido)-5-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=2CC(C)CCC=2SC=1NS(=O)(=O)C1=CC=CC=C1 PYUUNGQMZIAFGY-UHFFFAOYSA-N 0.000 claims 1
- KCVZECLWSXSEIL-UHFFFAOYSA-N 2-(benzenesulfonamido)-5-phenylthiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=C(C=2C=CC=CC=2)SC=1NS(=O)(=O)C1=CC=CC=C1 KCVZECLWSXSEIL-UHFFFAOYSA-N 0.000 claims 1
- HKKYLULYVVFFNL-UHFFFAOYSA-N 2-(benzenesulfonamido)-6,6-dimethyl-5,7-dihydro-4h-1-benzothiophene-3-carboxylic acid Chemical compound C1C(C)(C)CCC(C=2C(O)=O)=C1SC=2NS(=O)(=O)C1=CC=CC=C1 HKKYLULYVVFFNL-UHFFFAOYSA-N 0.000 claims 1
- LVXBYZPEQCJIKC-UHFFFAOYSA-N 2-(benzenesulfonamido)-6,7-dihydro-4h-thieno[3,2-c]pyran-3-carboxylic acid Chemical compound S1C=2CCOCC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=CC=C1 LVXBYZPEQCJIKC-UHFFFAOYSA-N 0.000 claims 1
- BZZFRURPCXTVAR-UHFFFAOYSA-N 2-(benzenesulfonamido)-6-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound C1C(C)CCC(C=2C(O)=O)=C1SC=2NS(=O)(=O)C1=CC=CC=C1 BZZFRURPCXTVAR-UHFFFAOYSA-N 0.000 claims 1
- ODCAMXGPTSPUSO-UHFFFAOYSA-N 2-(cyclohexylsulfonylamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound S1C=2CCCCC=2C(C(=O)O)=C1NS(=O)(=O)C1CCCCC1 ODCAMXGPTSPUSO-UHFFFAOYSA-N 0.000 claims 1
- DIKASPZKNNUUMB-UHFFFAOYSA-N 2-[(2-chlorophenyl)sulfonylamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound S1C=2CCCCC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=CC=C1Cl DIKASPZKNNUUMB-UHFFFAOYSA-N 0.000 claims 1
- MILLGEPUKRKMDF-UHFFFAOYSA-N 2-[(2-methoxyphenyl)sulfonylamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound COC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)C(CCCC2)=C2S1 MILLGEPUKRKMDF-UHFFFAOYSA-N 0.000 claims 1
- MUWRWQCNEKKDJR-UHFFFAOYSA-N 2-[(2-methylphenyl)sulfonylamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)C(CCCC2)=C2S1 MUWRWQCNEKKDJR-UHFFFAOYSA-N 0.000 claims 1
- WTEVHUMNEVLMMN-UHFFFAOYSA-N 2-[(4-chlorophenyl)sulfonylamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound S1C=2CCCCC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 WTEVHUMNEVLMMN-UHFFFAOYSA-N 0.000 claims 1
- ITFLULGFSYSPAE-UHFFFAOYSA-N 2-[(4-fluorophenyl)sulfonylamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound S1C=2CCCCC=2C(C(=O)O)=C1NS(=O)(=O)C1=CC=C(F)C=C1 ITFLULGFSYSPAE-UHFFFAOYSA-N 0.000 claims 1
- SFJJCFSPGCWVAE-LUAWRHEFSA-N 2-[[2-[(z)-3-(diethylamino)prop-1-enyl]phenyl]sulfonylamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC=CC=C1S(=O)(=O)NC1=C(C(O)=O)C(CCCC2)=C2S1 SFJJCFSPGCWVAE-LUAWRHEFSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 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
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 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 |
|---|---|---|---|
| US39210810P | 2010-10-12 | 2010-10-12 | |
| US61/392,108 | 2010-10-12 | ||
| US42005010P | 2010-12-06 | 2010-12-06 | |
| US61/420,050 | 2010-12-06 | ||
| PCT/US2011/055987 WO2012051318A1 (en) | 2010-10-12 | 2011-10-12 | Sulphonamide compounds and methods of making and using same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013539789A JP2013539789A (ja) | 2013-10-28 |
| JP2013539789A5 true JP2013539789A5 (https=) | 2014-11-27 |
| JP5913333B2 JP5913333B2 (ja) | 2016-04-27 |
Family
ID=44903376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013533977A Active JP5913333B2 (ja) | 2010-10-12 | 2011-10-12 | スルホンアミド化合物、およびそれを製造し使用する方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9221787B2 (https=) |
| EP (1) | EP2627632A1 (https=) |
| JP (1) | JP5913333B2 (https=) |
| KR (1) | KR20140026330A (https=) |
| CN (1) | CN103370307B (https=) |
| AU (1) | AU2011316550A1 (https=) |
| BR (1) | BR112013008856A2 (https=) |
| CA (1) | CA2814413A1 (https=) |
| MX (1) | MX339201B (https=) |
| WO (1) | WO2012051318A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010065877A2 (en) | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Methods of treating an overweight or obese subject |
| US8642650B2 (en) | 2008-12-04 | 2014-02-04 | Zafgen, Inc. | Methods of treating an overweight or obese subject |
| WO2013055385A2 (en) | 2011-10-03 | 2013-04-18 | Zafgen Corporation | Methods of treating age related disorders |
| CA2777108A1 (en) | 2009-10-09 | 2011-04-14 | Zafgen Corporation | Sulphone compounds and methods of making and using same |
| US8815309B2 (en) | 2010-01-08 | 2014-08-26 | Zafgen, Inc. | Methods of treating a subject with benign prostate hyperplasia |
| BR112012016793A2 (pt) | 2010-01-08 | 2018-07-31 | Zafgen Corp | compostos tipo fumagilol e métodos de fazer e usar os mesmos |
| WO2011127304A2 (en) | 2010-04-07 | 2011-10-13 | Zafgen Corporation | Methods of treating an overweight subject |
| CN103249735B (zh) | 2010-07-22 | 2016-04-06 | 扎夫根股份有限公司 | 三环化合物及其制备和使用方法 |
| US9173865B2 (en) | 2010-11-29 | 2015-11-03 | Zafgen, Inc. | Treatment of obesity using non-daily administration of 6-O-(4-dimethylaminoethoxy) cinnamoyl fumagillol |
| MX344238B (es) | 2011-01-26 | 2016-12-07 | Zafgen Inc | Compuestos de tetrazol y métodos para preparar y usar los mismos. |
| EP2683706B1 (en) | 2011-03-08 | 2018-02-21 | Zafgen, Inc. | Oxaspiro [2.5]octane derivatives and analogs |
| EP2705036B1 (en) | 2011-05-06 | 2015-08-12 | Zafgen Inc. | Tricyclic sulfonamide compounds and methods of making and using same |
| CN103764641B (zh) | 2011-05-06 | 2016-10-26 | 扎夫根股份有限公司 | 部分饱和的三环化合物及其制备和使用方法 |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| MX2014008706A (es) | 2012-01-18 | 2015-03-05 | Zafgen Inc | Compuestos tricíclicos de sulfonamida y métodos para elaborarlos y usarlos. |
| JP2015509102A (ja) | 2012-01-18 | 2015-03-26 | ザフゲン，インコーポレイテッド | 三環式スルホン化合物並びにその作製および使用方法 |
| MX2014013599A (es) | 2012-05-08 | 2015-05-11 | Zafgen Inc | Tratamiento de la obesidad hipotalamica con inhibidores de metap2. |
| BR112014027981A2 (pt) | 2012-05-09 | 2017-06-27 | Zafgen Inc | compostos do tipo fumagilol e métodos de produção e utilização dos mesmos |
| MX2015005733A (es) | 2012-11-05 | 2016-02-10 | Zafgen Inc | Compuestos triciclicos para usarse en el tratamiento y/o control de obesidad. |
| AU2013337282A1 (en) | 2012-11-05 | 2015-05-21 | Zafgen, Inc. | Tricyclic compounds and methods of making and using same |
| NZ707773A (en) | 2012-11-05 | 2019-05-31 | Zafgen Inc | Methods of treating liver diseases |
| CN105228610A (zh) | 2013-03-14 | 2016-01-06 | 扎夫根股份有限公司 | 治疗肾疾病和其它病症的方法 |
| WO2015184214A1 (en) | 2014-05-30 | 2015-12-03 | Dow Corning Corporation | Process of synthesizing diisopropylaminw-disilanes |
| JPWO2016039403A1 (ja) * | 2014-09-11 | 2017-06-29 | 塩野義製薬株式会社 | 持続性ｈｉｖプロテアーゼ阻害剤 |
| 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 |
| AR105671A1 (es) | 2015-08-11 | 2017-10-25 | Zafgen Inc | Compuestos heterocíclicos de fumagillol y sus métodos de elaboración y uso |
| IT202100022172A1 (it) * | 2021-08-23 | 2023-02-23 | Natural Acad S R L | Composizione liquida medicale per somministrazione aerea |
| WO2023212095A1 (en) * | 2022-04-27 | 2023-11-02 | The Regents Of The University Of California | Molecules that enhance extracellular vesicle release |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6551611B2 (en) * | 1995-09-28 | 2003-04-22 | Schering Aktiengesellschaft | Hormone replacement therapy method |
| US7491718B2 (en) | 2002-10-08 | 2009-02-17 | Abbott Laboratories | Sulfonamides having antiangiogenic and anticancer activity |
| DE102007020492A1 (de) * | 2007-04-30 | 2008-11-06 | Grünenthal GmbH | Substituierte Sulfonamid-Derivate |
| EP2220065A2 (en) * | 2007-07-30 | 2010-08-25 | Encysive Pharmaceuticals, Inc. | Modulators of ccr9 receptor and methods of use thereof |
| EP2227466B1 (de) | 2007-11-30 | 2011-04-20 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte piperidine |
| US20120010290A1 (en) | 2008-12-04 | 2012-01-12 | Vath James E | Methods of Treating an Overweight or Obese Subject |
| CA2777108A1 (en) | 2009-10-09 | 2011-04-14 | Zafgen Corporation | Sulphone compounds and methods of making and using same |
| CN103249735B (zh) | 2010-07-22 | 2016-04-06 | 扎夫根股份有限公司 | 三环化合物及其制备和使用方法 |
| MX344238B (es) | 2011-01-26 | 2016-12-07 | Zafgen Inc | Compuestos de tetrazol y métodos para preparar y usar los mismos. |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| CN103764641B (zh) | 2011-05-06 | 2016-10-26 | 扎夫根股份有限公司 | 部分饱和的三环化合物及其制备和使用方法 |
| EP2705036B1 (en) | 2011-05-06 | 2015-08-12 | Zafgen Inc. | Tricyclic sulfonamide compounds and methods of making and using same |
-
2011
- 2011-10-12 US US13/878,958 patent/US9221787B2/en not_active Expired - Fee Related
- 2011-10-12 EP EP11773159.6A patent/EP2627632A1/en not_active Withdrawn
- 2011-10-12 AU AU2011316550A patent/AU2011316550A1/en not_active Abandoned
- 2011-10-12 MX MX2013004079A patent/MX339201B/es active IP Right Grant
- 2011-10-12 KR KR1020137012153A patent/KR20140026330A/ko not_active Withdrawn
- 2011-10-12 CA CA2814413A patent/CA2814413A1/en not_active Abandoned
- 2011-10-12 BR BR112013008856A patent/BR112013008856A2/pt not_active IP Right Cessation
- 2011-10-12 JP JP2013533977A patent/JP5913333B2/ja active Active
- 2011-10-12 CN CN201180059472.9A patent/CN103370307B/zh not_active Expired - Fee Related
- 2011-10-12 WO PCT/US2011/055987 patent/WO2012051318A1/en not_active Ceased
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