CA2729998A1 - Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 - Google Patents
Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 Download PDFInfo
- Publication number
- CA2729998A1 CA2729998A1 CA2729998A CA2729998A CA2729998A1 CA 2729998 A1 CA2729998 A1 CA 2729998A1 CA 2729998 A CA2729998 A CA 2729998A CA 2729998 A CA2729998 A CA 2729998A CA 2729998 A1 CA2729998 A1 CA 2729998A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- halo
- cycloalkyl
- alkoxy
- hydroxy
- 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.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title description 26
- 102100036506 11-beta-hydroxysteroid dehydrogenase 1 Human genes 0.000 title 1
- 101710186107 11-beta-hydroxysteroid dehydrogenase 1 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 197
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 241000124008 Mammalia Species 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 372
- 125000005843 halogen group Chemical group 0.000 claims description 354
- -1 cyano, hydroxy, amino Chemical group 0.000 claims description 261
- 125000003545 alkoxy group Chemical group 0.000 claims description 210
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 176
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 149
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 123
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 97
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 89
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 84
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 76
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 73
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 70
- 125000003282 alkyl amino group Chemical group 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 66
- 125000004043 oxo group Chemical group O=* 0.000 claims description 64
- 239000000460 chlorine Substances 0.000 claims description 61
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 60
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 59
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 57
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 56
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 56
- 239000011737 fluorine Substances 0.000 claims description 56
- 229910052731 fluorine Inorganic materials 0.000 claims description 56
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 50
- 125000001188 haloalkyl group Chemical group 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 50
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 48
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 47
- 229910052801 chlorine Inorganic materials 0.000 claims description 47
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 125000003386 piperidinyl group Chemical group 0.000 claims description 43
- 125000004414 alkyl thio group Chemical group 0.000 claims description 37
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 37
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 32
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 32
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 30
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 29
- 125000005145 cycloalkylaminosulfonyl group Chemical group 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 230000000694 effects Effects 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 22
- 125000003368 amide group Chemical class 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 20
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 20
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 18
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 15
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 14
- 125000005148 cycloalkylalkanesulfinyl group Chemical group 0.000 claims description 14
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 13
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 230000014509 gene expression Effects 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Chemical group 0.000 claims description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000005479 oxodihydropyridyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 32
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 15
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 10
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 2
- 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 description 53
- 238000006243 chemical reaction Methods 0.000 abstract description 30
- 229960000890 hydrocortisone Drugs 0.000 abstract description 26
- 230000005764 inhibitory process Effects 0.000 abstract description 20
- 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 description 8
- 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 description 8
- 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 description 7
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- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000001225 therapeutic effect Effects 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 description 113
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- 239000000243 solution Substances 0.000 description 99
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 238000001819 mass spectrum Methods 0.000 description 80
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 67
- 229910001868 water Inorganic materials 0.000 description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 239000000543 intermediate Substances 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 35
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- 230000035897 transcription Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- A61P5/46—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of glucocorticosteroids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13593308P | 2008-07-25 | 2008-07-25 | |
| US61/135,933 | 2008-07-25 | ||
| US20676709P | 2009-02-04 | 2009-02-04 | |
| US61/206,767 | 2009-02-04 | ||
| PCT/EP2009/059509 WO2010010157A2 (en) | 2008-07-25 | 2009-07-23 | INHIBITORS OF 11beta-HYDROXYSTEROID DEHYDROGENASE 1 |
Publications (1)
| Publication Number | Publication Date |
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| CA2729998A1 true CA2729998A1 (en) | 2010-01-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CA2729998A Abandoned CA2729998A1 (en) | 2008-07-25 | 2009-07-23 | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8846668B2 (enExample) |
| EP (1) | EP2324017B1 (enExample) |
| JP (1) | JP5777030B2 (enExample) |
| AR (1) | AR072753A1 (enExample) |
| CA (1) | CA2729998A1 (enExample) |
| TW (1) | TW201016691A (enExample) |
| WO (1) | WO2010010157A2 (enExample) |
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| WO2008106128A2 (en) | 2007-02-26 | 2008-09-04 | Vitae Pharmaceuticals, Inc. | CYCLIC UREA AND CARBAMATE INHIBITORS OF 11β -HYDROXYSTEROID DEHYDROGENASE 1 |
| ATE554078T1 (de) | 2007-07-26 | 2012-05-15 | Vitae Pharmaceuticals Inc | Synthese von 11-beta-hydroxysteroid-dehydrogenase-1-hemmern |
| AR069207A1 (es) | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| CA2704628C (en) | 2007-11-16 | 2016-11-29 | Boehringer Ingelheim International Gmbh | Aryl- and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
| EP2229368A1 (en) | 2007-12-11 | 2010-09-22 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| TW200934490A (en) | 2008-01-07 | 2009-08-16 | Vitae Pharmaceuticals Inc | Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1 |
| EP2252601B1 (en) * | 2008-01-24 | 2012-12-19 | Vitae Pharmaceuticals, Inc. | Cyclic carbazate and semicarbazide inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5730021B2 (ja) | 2008-02-15 | 2015-06-03 | 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の阻害剤としてのシクロアルキルラクタム誘導体 |
| WO2009134387A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| NZ588954A (en) | 2008-05-01 | 2012-08-31 | Vitae Pharmaceuticals Inc | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2009134392A1 (en) | 2008-05-01 | 2009-11-05 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CL2009001151A1 (es) | 2008-05-13 | 2010-08-13 | Boehringer Ingelheim Int | Compuestos derivados de acidos carbociclicos aliciclicos de benzomorfanos, procedimiento de preparacion, composicion farmaceutica, utiles para tratar enfermedades influenciadas por la inhibicion de la enzima 11beta-hidroxiesteroide deshidrogenasa, como trastornos metabolicos. |
| JP5390610B2 (ja) * | 2008-07-25 | 2014-01-15 | 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型の阻害剤の合成 |
| PL2324018T3 (pl) | 2008-07-25 | 2014-02-28 | Boehringer Ingelheim Int | Cykliczne inhibitory dehydrogenazy 11 beta-hydroksysteroidowej typu 1 |
| CA2729998A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| CA2738453C (en) | 2008-10-23 | 2017-07-04 | Boehringer Ingelheim International Gmbh | Urea derivatives of substituted nortropanes, medicaments containing such compounds and their use |
| EP2393807B1 (en) | 2009-02-04 | 2013-08-14 | Boehringer Ingelheim International GmbH | Cyclic inhibitors of 11 -hydroxysteroid dehydrogenase 1 |
| UA109255C2 (ru) | 2009-04-30 | 2015-08-10 | Берінгер Інгельхайм Інтернешнл Гмбх | Циклические ингибиторы 11бета-гидроксистероиддегидрогеназы 1 |
| KR20120061771A (ko) * | 2009-04-30 | 2012-06-13 | 비타이 파마슈티컬즈, 인코포레이티드 | 11베타-하이드록시스테로이드 탈수소효소 1의 고리형 억제제 |
| TW201040167A (en) * | 2009-04-30 | 2010-11-16 | Boehringer Ingelheim Int | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5670440B2 (ja) | 2009-06-02 | 2015-02-18 | 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 |
| WO2011011123A1 (en) | 2009-06-11 | 2011-01-27 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 based on the 1,3 -oxazinan- 2 -one structure |
| JP5749263B2 (ja) | 2009-07-01 | 2015-07-15 | 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の環状インヒビター |
| WO2011056737A1 (en) | 2009-11-05 | 2011-05-12 | Boehringer Ingelheim International Gmbh | Novel chiral phosphorus ligands |
| UY33001A (es) | 2009-11-06 | 2011-05-31 | Boehringer Ingelheim Int | Derivados arilo y heteroarilcarbonilo de hexahidroindenopiridina y octahidrobenzoquinolina |
| EP2576570A1 (en) | 2010-05-26 | 2013-04-10 | Boehringer Ingelheim International GmbH | 2-oxo-1,2-dihydropyridin-4-ylboronic acid derivatives |
| EP2582698B1 (en) | 2010-06-16 | 2016-09-14 | Vitae Pharmaceuticals, Inc. | Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| WO2011161128A1 (en) | 2010-06-25 | 2011-12-29 | Boehringer Ingelheim International Gmbh | Azaspirohexanones as inhibitors of 11-beta-hsd1 for the treatment of metabolic disorders |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| KR20130137628A (ko) | 2010-11-02 | 2013-12-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 대사 장애를 치료하기 위한 약제학적 병용물 |
| TWI537258B (zh) | 2010-11-05 | 2016-06-11 | 百靈佳殷格翰國際股份有限公司 | 六氫茚并吡啶及八氫苯并喹啉之芳基－及雜環芳基羰基衍生物 |
| EP2704573A4 (en) * | 2011-05-03 | 2014-10-15 | Merck Sharp & Dohme | AMINOMETHYL biaryl BENZOTRIAZOL DERIVATIVES |
| WO2013025664A1 (en) | 2011-08-17 | 2013-02-21 | Boehringer Ingelheim International Gmbh | Indenopyridine derivatives |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| CN103342700B (zh) * | 2012-01-19 | 2016-04-20 | 通化济达医药有限公司 | 11β-羟基类固醇脱氢酶1型抑制剂 |
| CN104788384A (zh) * | 2015-03-31 | 2015-07-22 | 山东友帮生化科技有限公司 | 一种3-羟基-6-氯哒嗪的合成方法 |
| EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
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| SU511005A3 (ru) | 1973-10-27 | 1976-04-15 | К.Х.Берингер Зон., (Фирма) | Способ получени (метоксиметилфурилметил)6,7-бензоморфанов или морфинанов |
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-
2009
- 2009-07-23 CA CA2729998A patent/CA2729998A1/en not_active Abandoned
- 2009-07-23 JP JP2011519178A patent/JP5777030B2/ja active Active
- 2009-07-23 WO PCT/EP2009/059509 patent/WO2010010157A2/en not_active Ceased
- 2009-07-23 TW TW098124916A patent/TW201016691A/zh unknown
- 2009-07-23 EP EP09780992.5A patent/EP2324017B1/en active Active
- 2009-07-23 US US13/054,954 patent/US8846668B2/en active Active
- 2009-07-24 AR ARP090102841A patent/AR072753A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8846668B2 (en) | 2014-09-30 |
| WO2010010157A3 (en) | 2010-04-01 |
| AR072753A1 (es) | 2010-09-15 |
| WO2010010157A2 (en) | 2010-01-28 |
| EP2324017A2 (en) | 2011-05-25 |
| TW201016691A (en) | 2010-05-01 |
| JP2011529029A (ja) | 2011-12-01 |
| EP2324017B1 (en) | 2014-12-31 |
| JP5777030B2 (ja) | 2015-09-09 |
| US20120108578A1 (en) | 2012-05-03 |
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