TW201016691A - Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 - Google Patents
Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 Download PDFInfo
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- TW201016691A TW201016691A TW098124916A TW98124916A TW201016691A TW 201016691 A TW201016691 A TW 201016691A TW 098124916 A TW098124916 A TW 098124916A TW 98124916 A TW98124916 A TW 98124916A TW 201016691 A TW201016691 A TW 201016691A
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- Prior art keywords
- alkyl
- group
- alkoxy
- cycloalkyl
- cvc6
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- 239000003112 inhibitor Substances 0.000 title description 24
- 102100036506 11-beta-hydroxysteroid dehydrogenase 1 Human genes 0.000 title description 2
- 101710186107 11-beta-hydroxysteroid dehydrogenase 1 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 168
- 150000003839 salts Chemical class 0.000 claims abstract description 69
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 23
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 594
- -1 hydroxy, carboxy Chemical group 0.000 claims description 311
- 125000003545 alkoxy group Chemical group 0.000 claims description 284
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 140
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 133
- 125000003282 alkyl amino group Chemical group 0.000 claims description 97
- 229910052736 halogen Inorganic materials 0.000 claims description 92
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 90
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 89
- 150000002367 halogens Chemical class 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
- 125000005843 halogen group Chemical group 0.000 claims description 69
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 66
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 60
- 150000001412 amines Chemical class 0.000 claims description 52
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 50
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 50
- 239000011737 fluorine Substances 0.000 claims description 47
- 229910052731 fluorine Inorganic materials 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 46
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 46
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 40
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 40
- 239000000460 chlorine Chemical group 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 37
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 34
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 29
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 25
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 25
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 24
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 24
- 230000000694 effects Effects 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 239000007789 gas Substances 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 125000003277 amino group Chemical group 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 19
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 19
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 102200077464 rs398122966 Human genes 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 18
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000005145 cycloalkylaminosulfonyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 13
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 11
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
- 102220498322 HLA class II histocompatibility antigen, DR beta 3 chain_R40S_mutation Human genes 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
- 150000001924 cycloalkanes Chemical class 0.000 claims description 9
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- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 9
- 150000002602 lanthanoids Chemical class 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 8
- 150000002923 oximes Chemical class 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- ROPLCSFPUPWHGJ-UHFFFAOYSA-N hydroxycyanamide Chemical compound ONC#N ROPLCSFPUPWHGJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 5
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
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- 125000001769 aryl amino group Chemical group 0.000 claims description 4
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- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 4
- BUIMWOLDCCGZKZ-UHFFFAOYSA-N n-hydroxynitramide Chemical compound ON[N+]([O-])=O BUIMWOLDCCGZKZ-UHFFFAOYSA-N 0.000 claims description 4
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- 238000007363 ring formation reaction Methods 0.000 claims description 4
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- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical group [Mo] ZOKXTWBITQBERF-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
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- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 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
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Classifications
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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
- C07D413/02—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
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- 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
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| WO2010010150A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| CA2729998A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
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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 EP EP09780992.5A patent/EP2324017B1/en active Active
- 2009-07-23 TW TW098124916A patent/TW201016691A/zh unknown
- 2009-07-23 WO PCT/EP2009/059509 patent/WO2010010157A2/en not_active Ceased
- 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 |
|---|---|
| US20120108578A1 (en) | 2012-05-03 |
| AR072753A1 (es) | 2010-09-15 |
| JP2011529029A (ja) | 2011-12-01 |
| EP2324017B1 (en) | 2014-12-31 |
| US8846668B2 (en) | 2014-09-30 |
| EP2324017A2 (en) | 2011-05-25 |
| WO2010010157A2 (en) | 2010-01-28 |
| JP5777030B2 (ja) | 2015-09-09 |
| WO2010010157A3 (en) | 2010-04-01 |
| CA2729998A1 (en) | 2010-01-28 |
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