JP2008504276A5 - - Google Patents
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- JP2008504276A5 JP2008504276A5 JP2007518278A JP2007518278A JP2008504276A5 JP 2008504276 A5 JP2008504276 A5 JP 2008504276A5 JP 2007518278 A JP2007518278 A JP 2007518278A JP 2007518278 A JP2007518278 A JP 2007518278A JP 2008504276 A5 JP2008504276 A5 JP 2008504276A5
- Authority
- JP
- Japan
- Prior art keywords
- cycloalkyl
- alkyl
- heterocycloalkyl
- aryl
- heteroaryl
- 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.)
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- 125000000753 cycloalkyl group Chemical group 0.000 claims 166
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 163
- 125000000217 alkyl group Chemical group 0.000 claims 138
- 125000003118 aryl group Chemical group 0.000 claims 117
- 125000001072 heteroaryl group Chemical group 0.000 claims 106
- 125000005843 halogen group Chemical group 0.000 claims 87
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 77
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 76
- 229910052799 carbon Inorganic materials 0.000 claims 75
- 125000003545 alkoxy group Chemical group 0.000 claims 62
- 229910052739 hydrogen Inorganic materials 0.000 claims 53
- 125000005466 alkylenyl group Chemical group 0.000 claims 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 45
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 44
- 125000003282 alkyl amino group Chemical group 0.000 claims 44
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 44
- -1 1,2,3,4-tetrahydro-naphthyl Chemical group 0.000 claims 43
- 125000004663 dialkyl amino group Chemical group 0.000 claims 43
- 125000004429 atom Chemical group 0.000 claims 41
- 125000003710 aryl alkyl group Chemical group 0.000 claims 39
- 150000001875 compounds Chemical class 0.000 claims 39
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 38
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 31
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 29
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 26
- 125000004432 carbon atom Chemical group C* 0.000 claims 25
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- 229910052760 oxygen Inorganic materials 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 15
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 14
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 14
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 239000000651 prodrug Substances 0.000 claims 7
- 229940002612 prodrug Drugs 0.000 claims 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 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 claims 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- NRLSCXYPMWSVRJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexyl-n-cyclopropylcyclopropane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C(=O)N(C2CC2)C2CCCCC2)CC1 NRLSCXYPMWSVRJ-UHFFFAOYSA-N 0.000 claims 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229960000890 hydrocortisone Drugs 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004344 phenylpropyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- OUYATPNZYSCUTE-UHFFFAOYSA-N 1-(2-chloro-4-fluorophenyl)sulfanyl-n-cyclohexylcyclopropane-1-carboxamide Chemical compound ClC1=CC(F)=CC=C1SC1(C(=O)NC2CCCCC2)CC1 OUYATPNZYSCUTE-UHFFFAOYSA-N 0.000 claims 1
- PXCRXJGDXUJZGT-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)sulfanyl-n-cyclohexylcyclopropane-1-carboxamide Chemical compound C1=C(Cl)C(F)=CC=C1SC1(C(=O)NC2CCCCC2)CC1 PXCRXJGDXUJZGT-UHFFFAOYSA-N 0.000 claims 1
- NXSAJNOPKSFUAG-GUYCJALGSA-N 1-(4-chlorophenyl)-n-[(1r,2s)-1-hydroxy-1-phenylpropan-2-yl]cyclopropane-1-carboxamide Chemical compound N([C@@H](C)[C@H](O)C=1C=CC=CC=1)C(=O)C1(C=2C=CC(Cl)=CC=2)CC1 NXSAJNOPKSFUAG-GUYCJALGSA-N 0.000 claims 1
- QYAIONJQKZMPAR-DLBZAZTESA-N 1-(4-chlorophenyl)-n-[(1r,2s)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]cyclopropane-1-carboxamide Chemical compound N([C@@H]1C2=CC=CC=C2C[C@@H]1O)C(=O)C1(C=2C=CC(Cl)=CC=2)CC1 QYAIONJQKZMPAR-DLBZAZTESA-N 0.000 claims 1
- NXSAJNOPKSFUAG-CXAGYDPISA-N 1-(4-chlorophenyl)-n-[(1s,2r)-1-hydroxy-1-phenylpropan-2-yl]cyclopropane-1-carboxamide Chemical compound N([C@H](C)[C@@H](O)C=1C=CC=CC=1)C(=O)C1(C=2C=CC(Cl)=CC=2)CC1 NXSAJNOPKSFUAG-CXAGYDPISA-N 0.000 claims 1
- RFOXIWXCIBKDHL-IRXDYDNUSA-N 1-(4-chlorophenyl)-n-[(1s,2s)-1,3-dihydroxy-1-phenylpropan-2-yl]cyclopropane-1-carboxamide Chemical compound N([C@@H](CO)[C@@H](O)C=1C=CC=CC=1)C(=O)C1(C=2C=CC(Cl)=CC=2)CC1 RFOXIWXCIBKDHL-IRXDYDNUSA-N 0.000 claims 1
- BJXCOVPVWLXTLP-ROUUACIJSA-N 1-(4-chlorophenyl)-n-[(1s,2s)-1-hydroxy-3-methoxy-1-phenylpropan-2-yl]cyclopropane-1-carboxamide Chemical compound N([C@@H](COC)[C@@H](O)C=1C=CC=CC=1)C(=O)C1(C=2C=CC(Cl)=CC=2)CC1 BJXCOVPVWLXTLP-ROUUACIJSA-N 0.000 claims 1
- ZZOJWHVCJSGPNE-MRXNPFEDSA-N 1-(4-chlorophenyl)-n-[(2r)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]cyclopropane-1-carboxamide Chemical compound C([C@H](CO)NC(=O)C1(CC1)C=1C=CC(Cl)=CC=1)C1=CC=C(O)C=C1 ZZOJWHVCJSGPNE-MRXNPFEDSA-N 0.000 claims 1
- VKWCIMWHVDSTFX-ZDUSSCGKSA-N 1-(4-chlorophenyl)-n-[(2r)-1-hydroxy-3-methylbutan-2-yl]cyclopropane-1-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)N[C@@H](CO)C(C)C)CC1 VKWCIMWHVDSTFX-ZDUSSCGKSA-N 0.000 claims 1
- SCLZMPSRNDBNPC-CQSZACIVSA-N 1-(4-chlorophenyl)-n-[(2r)-1-hydroxy-4-methylpentan-2-yl]cyclopropane-1-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)N[C@@H](CO)CC(C)C)CC1 SCLZMPSRNDBNPC-CQSZACIVSA-N 0.000 claims 1
- RSJLSDSANODJRX-KRWDZBQOSA-N 1-(4-chlorophenyl)-n-[(2s)-1-cyclohexyl-3-hydroxypropan-2-yl]cyclopropane-1-carboxamide Chemical compound C([C@@H](CO)NC(=O)C1(CC1)C=1C=CC(Cl)=CC=1)C1CCCCC1 RSJLSDSANODJRX-KRWDZBQOSA-N 0.000 claims 1
- KENHMWLUSFIOCC-KRWDZBQOSA-N 1-(4-chlorophenyl)-n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]cyclopropane-1-carboxamide Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)CO)C(=O)C1(C=2C=CC(Cl)=CC=2)CC1 KENHMWLUSFIOCC-KRWDZBQOSA-N 0.000 claims 1
- MLCMNKUIRROHKO-SFHVURJKSA-N 1-(4-chlorophenyl)-n-[(2s)-1-hydroxy-3-phenylmethoxypropan-2-yl]cyclopropane-1-carboxamide Chemical compound C([C@H](CO)NC(=O)C1(CC1)C=1C=CC(Cl)=CC=1)OCC1=CC=CC=C1 MLCMNKUIRROHKO-SFHVURJKSA-N 0.000 claims 1
- SCLZMPSRNDBNPC-AWEZNQCLSA-N 1-(4-chlorophenyl)-n-[(2s)-1-hydroxy-4-methylpentan-2-yl]cyclopropane-1-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)N[C@H](CO)CC(C)C)CC1 SCLZMPSRNDBNPC-AWEZNQCLSA-N 0.000 claims 1
- BNWAVTWSLGBASW-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-[1-(hydroxymethyl)cyclopentyl]cyclopropane-1-carboxamide Chemical compound C1CC1(C=1C=CC(Cl)=CC=1)C(=O)NC1(CO)CCCC1 BNWAVTWSLGBASW-UHFFFAOYSA-N 0.000 claims 1
- IHGRZRKBWONUPU-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexylcyclopropane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C(=O)NC2CCCCC2)CC1 IHGRZRKBWONUPU-UHFFFAOYSA-N 0.000 claims 1
- FBWCHFNYEDPHQF-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclopentyl-n-cyclopropylcyclopropane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C(=O)N(C2CC2)C2CCCC2)CC1 FBWCHFNYEDPHQF-UHFFFAOYSA-N 0.000 claims 1
- VOHYLPCJNUVTDG-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanyl-n-cyclohexyl-n-cyclopropylcyclopropane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1SC1(C(=O)N(C2CC2)C2CCCCC2)CC1 VOHYLPCJNUVTDG-UHFFFAOYSA-N 0.000 claims 1
- MYAPGVBIWBWCCQ-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanyl-n-cyclohexylcyclopropane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1SC1(C(=O)NC2CCCCC2)CC1 MYAPGVBIWBWCCQ-UHFFFAOYSA-N 0.000 claims 1
- OJIIYPKFCHWNDV-UHFFFAOYSA-N 1-[(4-chlorophenyl)methoxy]-n-cyclohexyl-n-cyclopropylcyclopropane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1COC1(C(=O)N(C2CC2)C2CCCCC2)CC1 OJIIYPKFCHWNDV-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- SFUUXQNRXIVXSA-UHFFFAOYSA-N 5-[3-fluoro-4-[1-[(4-hydroxy-4-methylcyclohexyl)carbamoyl]cyclopropyl]phenyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=CC=C(C2(CC2)C(=O)NC2CCC(C)(O)CC2)C(F)=C1 SFUUXQNRXIVXSA-UHFFFAOYSA-N 0.000 claims 1
- BWKXKSUWTPHVKM-UHFFFAOYSA-N 5-[4-[1-(cycloheptylcarbamoyl)cyclopropyl]-3-fluorophenyl]-n-ethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CC=C1C1=CC=C(C2(CC2)C(=O)NC2CCCCCC2)C(F)=C1 BWKXKSUWTPHVKM-UHFFFAOYSA-N 0.000 claims 1
- YYNGPVSYOZCYCI-UHFFFAOYSA-N 5-[4-[1-(cyclohexylcarbamoyl)cyclopropyl]-3-fluorophenyl]-n-ethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CC=C1C1=CC=C(C2(CC2)C(=O)NC2CCCCC2)C(F)=C1 YYNGPVSYOZCYCI-UHFFFAOYSA-N 0.000 claims 1
- IQBAAVAHWBVREO-UHFFFAOYSA-N 5-[4-[1-[cyclohexyl(methyl)carbamoyl]cyclopropyl]-3-fluorophenyl]-n-ethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CC=C1C1=CC=C(C2(CC2)C(=O)N(C)C2CCCCC2)C(F)=C1 IQBAAVAHWBVREO-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- MJMGSEHEWTYEKI-IYARVYRRSA-N C1=NC(C(=O)NC)=CC=C1C1=CC=C(C2(CC2)C(=O)N(C)[C@@H]2CC[C@@H](O)CC2)C(F)=C1 Chemical compound C1=NC(C(=O)NC)=CC=C1C1=CC=C(C2(CC2)C(=O)N(C)[C@@H]2CC[C@@H](O)CC2)C(F)=C1 MJMGSEHEWTYEKI-IYARVYRRSA-N 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 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 claims 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 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010070901 Diabetic dyslipidaemia Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 1
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 229960002478 aldosterone Drugs 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 229960004544 cortisone Drugs 0.000 claims 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- QHPJGXZQAOFTON-HZPDHXFCSA-N ethyl (1r,2r)-2-[[1-(4-chlorophenyl)cyclopropanecarbonyl]amino]cyclohexane-1-carboxylate Chemical compound CCOC(=O)[C@@H]1CCCC[C@H]1NC(=O)C1(C=2C=CC(Cl)=CC=2)CC1 QHPJGXZQAOFTON-HZPDHXFCSA-N 0.000 claims 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- IPCZZFBQEBOFBP-UHFFFAOYSA-N n-(1-acetylpiperidin-4-yl)-1-(4-chlorophenyl)-n-cyclopropylcyclopropane-1-carboxamide Chemical compound C1CN(C(=O)C)CCC1N(C(=O)C1(CC1)C=1C=CC(Cl)=CC=1)C1CC1 IPCZZFBQEBOFBP-UHFFFAOYSA-N 0.000 claims 1
- RLXYIFGXEREDJK-DLBZAZTESA-N n-[(1r,2s)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-1-phenylsulfanylcyclopropane-1-carboxamide Chemical compound N([C@@H]1C2=CC=CC=C2C[C@@H]1O)C(=O)C1(SC=2C=CC=CC=2)CC1 RLXYIFGXEREDJK-DLBZAZTESA-N 0.000 claims 1
- FTYYBOZBIGQPTQ-INIZCTEOSA-N n-[(2s)-1-hydroxy-3-(1h-indol-3-yl)propan-2-yl]-1-phenylsulfanylcyclopropane-1-carboxamide Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)CO)C(=O)C1(SC=2C=CC=CC=2)CC1 FTYYBOZBIGQPTQ-INIZCTEOSA-N 0.000 claims 1
- HSAKVFPHMDNCQB-UHFFFAOYSA-N n-[1-(3-chloro-2-methylphenyl)sulfonylpiperidin-3-yl]-1-phenylcyclopropane-1-carboxamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)N1CC(NC(=O)C2(CC2)C=2C=CC=CC=2)CCC1 HSAKVFPHMDNCQB-UHFFFAOYSA-N 0.000 claims 1
- HKYDGIIWVLWMCO-UHFFFAOYSA-N n-cyclohexyl-1-cyclohexylsulfonyl-n-cyclopropylcyclopropane-1-carboxamide Chemical compound C1CC1(S(=O)(=O)C1CCCCC1)C(=O)N(C1CCCCC1)C1CC1 HKYDGIIWVLWMCO-UHFFFAOYSA-N 0.000 claims 1
- UKFXGXJABCCUTK-UHFFFAOYSA-N n-cyclopentyl-n-cyclopropyl-1-phenylcyclopropane-1-carboxamide Chemical compound C1CC1(C=1C=CC=CC=1)C(=O)N(C1CCCC1)C1CC1 UKFXGXJABCCUTK-UHFFFAOYSA-N 0.000 claims 1
- KXUZZARZIOOPPQ-UHFFFAOYSA-N n-cyclopropyl-n-(cyclopropylmethyl)-1-phenylcyclopropane-1-carboxamide Chemical compound C1CC1(C=1C=CC=CC=1)C(=O)N(C1CC1)CC1CC1 KXUZZARZIOOPPQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000008816 organ damage Effects 0.000 claims 1
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- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- FWNFEUHPLDXASU-UHFFFAOYSA-N tert-butyl 4-[[1-(4-chlorophenyl)cyclopropanecarbonyl]-cyclopropylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N(C(=O)C1(CC1)C=1C=CC(Cl)=CC=1)C1CC1 FWNFEUHPLDXASU-UHFFFAOYSA-N 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 0 *C(*)(C(N(*)*)=O)I* Chemical compound *C(*)(C(N(*)*)=O)I* 0.000 description 10
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| US20100222316A1 (en) | 2004-04-29 | 2010-09-02 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| TWI350168B (en) | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| WO2006002361A2 (en) * | 2004-06-24 | 2006-01-05 | Incyte Corporation | 2-methylpropanamides and their use as pharmaceuticals |
| BRPI0512535A (pt) * | 2004-06-24 | 2008-03-25 | Incyte Corp | compostos de piperidinas n-substituìdas, suas composições e métodos de modulações |
| CA2589565A1 (en) * | 2004-06-24 | 2006-01-05 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| CA2569507A1 (en) * | 2004-06-24 | 2006-02-02 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| CA2571258A1 (en) * | 2004-06-24 | 2006-01-05 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| AU2005273986A1 (en) * | 2004-08-10 | 2006-02-23 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
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| US8110581B2 (en) | 2004-11-10 | 2012-02-07 | Incyte Corporation | Lactam compounds and their use as pharmaceuticals |
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| US20090192198A1 (en) | 2005-01-05 | 2009-07-30 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US8198331B2 (en) | 2005-01-05 | 2012-06-12 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
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-
2005
- 2005-06-23 US US11/159,862 patent/US20050288338A1/en not_active Abandoned
- 2005-06-23 EP EP05763383A patent/EP1773780A4/en not_active Withdrawn
- 2005-06-23 WO PCT/US2005/022308 patent/WO2006012227A2/en not_active Ceased
- 2005-06-23 JP JP2007518278A patent/JP2008504276A/ja not_active Withdrawn
- 2005-06-23 CA CA002570694A patent/CA2570694A1/en not_active Abandoned
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