AR076936A1 - Inhibidores de carbamato y urea de la 11 beta hidroxiesteroide deshidrogenasa 1 - Google Patents
Inhibidores de carbamato y urea de la 11 beta hidroxiesteroide deshidrogenasa 1Info
- Publication number
- AR076936A1 AR076936A1 ARP100101907A ARP100101907A AR076936A1 AR 076936 A1 AR076936 A1 AR 076936A1 AR P100101907 A ARP100101907 A AR P100101907A AR P100101907 A ARP100101907 A AR P100101907A AR 076936 A1 AR076936 A1 AR 076936A1
- Authority
- AR
- Argentina
- Prior art keywords
- optionally substituted
- heterocyclyl
- cycloalkyl
- alkyl
- heteroaryl
- Prior art date
Links
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title 1
- 101710088194 Dehydrogenase Proteins 0.000 title 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title 1
- 239000004202 carbamide Substances 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 9
- 125000000623 heterocyclic group Chemical group 0.000 abstract 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 5
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000003107 substituted aryl group Chemical group 0.000 abstract 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 2
- 229960000890 hydrocortisone Drugs 0.000 abstract 2
- 230000005764 inhibitory process Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 abstract 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 abstract 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229960004544 cortisone Drugs 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compuestos que son utiles para el tratamiento terapéutico de enfermedades asociadas con la modulacion o inhibicion de 11beta-HSD1 en mamíferos, también se refiere a composiciones farmacéuticas de los compuestos y a métodos para su uso en la reduccion o control de la produccion de cortisol en una célula o la inhibicion de la conversion de cortisona en cortisol en una célula. Reivindicacion 1: Un compuesto de formula 1 en la que Cy es bicicloalquilo C7-1) o tricicloalquilo C9-12, en el que 1-2 átomos de carbono están opcionalmente reemplazados con un heteroátomo seleccionado independientemente entre N y O, y que está opcionalmente sustituido con 1-3 grupos seleccionados independientemente entre halogeno, nitro, ciano, alquilo C1-3, haloalquilo C1-3, hidroxialquilo C1-3, OR4, haloalcoxi C1-3, N(R4)2, (CH2)xC(=NOH)NH2, (CH2)xNR4CON(R4)2, (CH2)xCON(R4)2, (CH2)xCO2R4, (CH2)xSO2N(R4)2, (CH2)xSO2R4, (CH2)xNR4COR4, (CH2)xNR4CO2R4, (CH2)xNR4SO2R4, (CH2)xOC(=O)N(R4)2, arilo opcionalmente sustituido, heteroarilo opcionalmente sustituido, heterociclilo opcionalmente sustituido y cicloalquilo opcionalmente sustituido, donde el arilo, heteroarilo, heterociclilo y cicloalquilo están opcionalmente sustituidos con uno a tres grupos representados por R7; B es arilo, heterociclilo o heteroarilo, cada uno opcionalmente sustituido con 1-4 grupos representados por R6; R3 es alquilo C1-8, alquenilo C2-8, alquinilo C2-8, cicloalquilalquilo C0-3, heterociclilalquilo C0-3, arilalquilo C0-3, heteroarilalquilo C0-3 o (CH2)xCO2R4, cada uno opcionalmente sustituido con 1-4 grupos seleccionados independientemente entre halogeno, nitro, ciano, alquilo C1-3, haloalquilo C1-3, haloalcoxi C1-3, hidroxialquilo C1-3, OR4, N(R4)2, (CH2)xC(=NOH)NH2, (CH2)xNR4CON(R4)2, (CH2)xCON(R4)2, (CH2)xCO2R4, (CH2)xSO2N(R4)2, (CH2)xSO2R4, (CH2)xNR4COR4, (CH2)xNR4CO2R4, (CH2)xNR4SO2R4, (CH2)xOC(=O)N(R4)2, (CH2)xOR4, (CH2)xO(CH2)xCO2R4, arilo opcionalmente sustituido, heteroarilo opcionalmente sustituido, heterociclilo opcionalmente sustituido y cicloalquilo opcionalmente sustituido, donde el arilo, heteroarilo, heterociclilo y cicloalquilo están opcionalmente sustituidos con uno a tres grupos representados por R7, donde el alquilo C1-8, alquenilo C2-8, alquinilo C2-8, cicloalquilo C3-8, heterociclilo, heteroarilo, cicloalquilalquilo C0-3, heterociclilalquilo C0-3, la porcion del alquilo arilalquilo C0-3 y heteroarilalquilo C0-3 están opcionalmente sustituidos adicionalmente con oxo; cada R4 es independientemente (a) hidrogeno; o (b) alquilo C1-10 o arilalquilo C0-3, cada uno opcionalmente sustituido con 1-4 grupos seleccionados entre halogeno, alcoxi C1-3, alquilo C1-3, haloalquilo C1-3, haloalcoxi C1-3, ciano y nitro; cada R6 se selecciona independientemente entre halogeno, nitro, ciano, alquilo C1-3, cicloalquilo C3-6, haloalquilo C1-3, hidroxialquilo C1-3, oxo, OR4, haloalcoxi C1-3, (CH2)xN(R4)2, (CH2)xC(=NOH)NH2, (CH2)xNR4CON(R4)2, (CH2)xCON(R4)2, (CH2)xCO2R4, (CH2)xSO2N(R4)2, (CH2)xSO2R4, (CH2)xNR4COR4, (CH2)xNR4CO2R4, (CH2)xNR4SO2R4, (CH2)xOC(=O)N(R4)2, (CH2)xOR4, (CH2)xO(CH2)xCO2R4, arilo opcionalmente sustituido, heteroarilo opcionalmente sustituido, heterociclilo opcionalmente sustituido y cicloalquilo opcionalmente sustituido, donde el arilo, heteroarilo, heterociclilo y cicloalquilo están opcionalmente sustituidos adicionalmente con uno a tres grupos representados por R7; R7 es halogeno, nitro, ciano, alquilo C1-3, haloalquilo C1-3, cicloalquilo C3-6, alcoxi C1-3, haloalcoxi C1-3, N(R4)2 o CON(R4)2, con la condicion de que R7 también incluya oxo cuando el heteroarilo, heterociclilo y cicloalquilo estén sustituidos con R7; x es 0, 1, 2 o 3; A' es un enlace, CH2, o -AO-, donde O está conectado a B; A es un enlace o CH2; m es 0 ,1, 2 0 3; y n es 1, 2 o 3; o una sal farmacéuticamente aceptable del mismo. Con la condicion de que el compuesto de formula 1 no es como en formula (2) o (3), o una sal farmacéuticamente aceptable del mismo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21759309P | 2009-06-02 | 2009-06-02 | |
| US26940609P | 2009-06-24 | 2009-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR076936A1 true AR076936A1 (es) | 2011-07-20 |
Family
ID=42315408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100101907A AR076936A1 (es) | 2009-06-02 | 2010-05-31 | Inhibidores de carbamato y urea de la 11 beta hidroxiesteroide deshidrogenasa 1 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9163012B2 (es) |
| EP (1) | EP2438043A1 (es) |
| JP (1) | JP5850459B2 (es) |
| AR (1) | AR076936A1 (es) |
| TW (1) | TW201103910A (es) |
| WO (1) | WO2010141424A1 (es) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR067673A1 (es) | 2007-07-26 | 2009-10-21 | Vitae Pharmaceuticals Inc | Derivados de 1,3 oxazinan - 2 - ona como inhibidores ciclicos de la 11 beta -hidroxiesteroide deshidrogenasa 1. composiciones farmaceuticas. |
| AR069207A1 (es) | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| US8440658B2 (en) | 2007-12-11 | 2013-05-14 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| JP5490020B2 (ja) | 2008-01-24 | 2014-05-14 | ヴァイティー ファーマシューティカルズ,インコーポレイテッド | 11β−ヒドロキシステロイドデヒドロゲナーゼ1の環状カルバゼート及びセミカルバジドインヒビター |
| WO2009102460A2 (en) | 2008-02-15 | 2009-08-20 | Vitae Pharmaceuticals, Inc. | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| MX2010011935A (es) | 2008-05-01 | 2011-05-19 | Vitae Pharmaceuticals Inc | Inhibidores ciclicos de 11 beta-hidroxiesteroide deshidrogenasa 1. |
| WO2009134387A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| NZ590495A (en) | 2008-07-25 | 2012-10-26 | Vitae Pharmaceuticals Inc | Dihydropyridin-phenyl-3-oxazinan-2-ones as inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| EP2324017B1 (en) | 2008-07-25 | 2014-12-31 | Boehringer Ingelheim International GmbH | INHIBITORS OF 11beta-HYDROXYSTEROID DEHYDROGENASE 1 |
| WO2010010150A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| JP5679997B2 (ja) | 2009-02-04 | 2015-03-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 11β−ヒドロキシステロイドデヒドロゲナーゼ1の環状阻害剤 |
| UA109255C2 (ru) | 2009-04-30 | 2015-08-10 | Берінгер Інгельхайм Інтернешнл Гмбх | Циклические ингибиторы 11бета-гидроксистероиддегидрогеназы 1 |
| AR076936A1 (es) | 2009-06-02 | 2011-07-20 | Vitae Pharmaceuticals Inc | Inhibidores de carbamato y urea de la 11 beta hidroxiesteroide deshidrogenasa 1 |
| ES2350077B1 (es) | 2009-06-04 | 2011-11-04 | Laboratorios Salvat, S.A. | Compuestos inhibidores de 11beta-hidroxiesteroide deshidrogenasa de tipo 1. |
| EP2440537A1 (en) | 2009-06-11 | 2012-04-18 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| WO2011056737A1 (en) | 2009-11-05 | 2011-05-12 | Boehringer Ingelheim International Gmbh | Novel chiral phosphorus ligands |
| US8648192B2 (en) | 2010-05-26 | 2014-02-11 | Boehringer Ingelheim International Gmbh | 2-oxo-1,2-dihydropyridin-4-ylboronic acid derivatives |
| WO2011159760A1 (en) | 2010-06-16 | 2011-12-22 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| EP2585444B1 (en) | 2010-06-25 | 2014-10-22 | Boehringer Ingelheim International GmbH | Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders |
| US8987273B2 (en) | 2010-07-28 | 2015-03-24 | Bayer Intellectual Property Gmbh | Substituted imidazo[1,2-B]pyridazines |
| EA201300522A1 (ru) | 2010-11-02 | 2013-11-29 | Бёрингер Ингельхайм Интернациональ Гмбх | Фармацевтические комбинации для лечения метаболических нарушений |
| WO2012136776A1 (en) | 2011-04-07 | 2012-10-11 | Bayer Intellectual Property Gmbh | Imidazopyridazines as akt kinase inhibitors |
| WO2014184272A2 (en) * | 2013-05-14 | 2014-11-20 | Medizinische Hochschule Hannover | Means and methods for treating cancer |
| EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
| CN115340481B (zh) * | 2022-08-08 | 2025-12-12 | 广州谷森制药有限公司 | 一种采用固载镍催化工业化生产氘代医药中间体的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5270302A (en) | 1988-12-21 | 1993-12-14 | Abbott Laboratories | Derivatives of tetrapeptides as CCK agonists |
| US5912114A (en) | 1997-09-12 | 1999-06-15 | Johnson & Johnson Medical, Inc. | Wound diagnosis by quantitating cortisol in wound fluids |
| TWI221102B (en) * | 2002-08-30 | 2004-09-21 | Sumitomo Heavy Industries | Laser material processing method and processing device |
| CN1744899A (zh) * | 2002-12-13 | 2006-03-08 | 史密丝克莱恩比彻姆公司 | 作为ccr5拮抗剂的哌啶衍生物 |
| CA2525124A1 (en) * | 2003-05-13 | 2004-11-25 | Schering Corporation | Bridged n-arylsulfonylpiperidines as gamma-secretase inhibitors |
| WO2008001817A1 (fr) * | 2006-06-27 | 2008-01-03 | Asahi Glass Company, Limited | composition À CRISTAUX LIQUIDES, élément optique à cristaux liquides, et procédé de fabrication d'ÉLÉMENT OPTIQUE À CRISTAUX LIQUIDES |
| WO2008024497A2 (en) | 2006-08-25 | 2008-02-28 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF 11β -HYDROXYSTEROID DEHYDROGENASE TYPE 1 |
| US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| WO2009001817A1 (ja) * | 2007-06-27 | 2008-12-31 | Taisho Pharmaceutical Co., Ltd. | 11β-HSD1阻害活性を有する化合物 |
| WO2009020140A1 (ja) * | 2007-08-06 | 2009-02-12 | Dainippon Sumitomo Pharma Co., Ltd. | アダマンチルウレア誘導体 |
| CA2702946A1 (en) * | 2007-10-16 | 2009-04-23 | Northeastern University | Monoacylglycerol lipase inhibitors for modulation of cannabinoid activity |
| TW200944526A (en) * | 2008-04-22 | 2009-11-01 | Vitae Pharmaceuticals Inc | Carbamate and urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| AR076936A1 (es) | 2009-06-02 | 2011-07-20 | Vitae Pharmaceuticals Inc | Inhibidores de carbamato y urea de la 11 beta hidroxiesteroide deshidrogenasa 1 |
-
2010
- 2010-05-31 AR ARP100101907A patent/AR076936A1/es unknown
- 2010-06-01 EP EP10722888A patent/EP2438043A1/en not_active Withdrawn
- 2010-06-01 US US12/791,592 patent/US9163012B2/en not_active Expired - Fee Related
- 2010-06-01 TW TW099117502A patent/TW201103910A/zh unknown
- 2010-06-01 WO PCT/US2010/036832 patent/WO2010141424A1/en not_active Ceased
- 2010-06-01 JP JP2012514033A patent/JP5850459B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20110053943A1 (en) | 2011-03-03 |
| JP2012528865A (ja) | 2012-11-15 |
| TW201103910A (en) | 2011-02-01 |
| US9163012B2 (en) | 2015-10-20 |
| WO2010141424A1 (en) | 2010-12-09 |
| EP2438043A1 (en) | 2012-04-11 |
| JP5850459B2 (ja) | 2016-02-03 |
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