KR20100132999A

KR20100132999A - 스테아로일 ＣｏＡ 불포화 효소 억제제로서 사용하기 위한 트리아졸로피리디논 유도체

스테아로일 ＣｏＡ 불포화 효소 억제제로서 사용하기 위한 트리아졸로피리디논 유도체 Download PDF

Info

Publication number: KR20100132999A
Authority: KR; South Korea
Prior art keywords: optionally substituted; compound; alkyl; dihydro; oxo
Prior art date: 2008-04-04
Legal status : Withdrawn

Application number

KR1020107024841A

Other languages

English (en)

Korean (ko)

Inventor

드미트리 콜툰

제프 자블록키

Original Assignee

길리애드 사이언시즈, 인코포레이티드

Priority date

2008-04-04

Filing date

2009-04-03

Publication date

2010-12-20

2009-04-03 Application filed by 길리애드 사이언시즈, 인코포레이티드 filed Critical 길리애드 사이언시즈, 인코포레이티드

2010-12-20 Publication of KR20100132999A publication Critical patent/KR20100132999A/ko

Status Withdrawn legal-status Critical Current

Links

239000003112 inhibitor Substances 0.000 title claims abstract description 12
LJRXNXBFJXXRNQ-UHFFFAOYSA-N 2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical class C1=CC=CN2C(=O)NN=C21 LJRXNXBFJXXRNQ-UHFFFAOYSA-N 0.000 title abstract description 3
125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 115
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 63
201000010099 disease Diseases 0.000 claims abstract description 52
208000008589 Obesity Diseases 0.000 claims abstract description 14
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 14
235000020824 obesity Nutrition 0.000 claims abstract description 14
SIARJEKBADXQJG-LFZQUHGESA-N stearoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 SIARJEKBADXQJG-LFZQUHGESA-N 0.000 claims abstract description 14
238000011282 treatment Methods 0.000 claims abstract description 13
102000004190 Enzymes Human genes 0.000 claims abstract description 11
108090000790 Enzymes Proteins 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims description 94
-1 4-chloro-3- (trifluoromethyl) benzyl Chemical group 0.000 claims description 85
125000001072 heteroaryl group Chemical group 0.000 claims description 56
125000001424 substituent group Chemical group 0.000 claims description 54
125000003545 alkoxy group Chemical group 0.000 claims description 31
229910052736 halogen Inorganic materials 0.000 claims description 29
150000002367 halogens Chemical class 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
125000003342 alkenyl group Chemical group 0.000 claims description 25
125000002947 alkylene group Chemical group 0.000 claims description 25
125000000753 cycloalkyl group Chemical group 0.000 claims description 23
125000000304 alkynyl group Chemical group 0.000 claims description 22
150000002431 hydrogen Chemical class 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
125000000547 substituted alkyl group Chemical group 0.000 claims description 11
208000032928 Dyslipidaemia Diseases 0.000 claims description 9
208000017170 Lipid metabolism disease Diseases 0.000 claims description 9
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
206010028980 Neoplasm Diseases 0.000 claims description 8
201000011510 cancer Diseases 0.000 claims description 8
230000001225 therapeutic effect Effects 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
DDDARTXFGYJQFS-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid Chemical compound O=C1N2C=C(C(=O)O)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 DDDARTXFGYJQFS-UHFFFAOYSA-N 0.000 claims description 6
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 6
206010022489 Insulin Resistance Diseases 0.000 claims description 6
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 6
208000006011 Stroke Diseases 0.000 claims description 5
239000002532 enzyme inhibitor Substances 0.000 claims description 5
239000008103 glucose Substances 0.000 claims description 5
JSCHCUAUVSTTPV-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]-n-(2-hydroxyethyl)-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound O=C1N2C=C(C(=O)NCCO)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 JSCHCUAUVSTTPV-UHFFFAOYSA-N 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
JDRORHFKYOKHML-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]-n-hexyl-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound O=C1N2C=C(C(=O)NCCCCCC)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 JDRORHFKYOKHML-UHFFFAOYSA-N 0.000 claims description 3
QLZBPKABEYQQMV-UHFFFAOYSA-N 2-[3-(2,5-dichlorophenoxy)propyl]-n-(2-hydroxyethyl)-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound O=C1N2C=C(C(=O)NCCO)C=CC2=NN1CCCOC1=CC(Cl)=CC=C1Cl QLZBPKABEYQQMV-UHFFFAOYSA-N 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
208000002249 Diabetes Complications Diseases 0.000 claims description 3
206010012655 Diabetic complications Diseases 0.000 claims description 3
102000004877 Insulin Human genes 0.000 claims description 3
108090001061 Insulin Proteins 0.000 claims description 3
208000032382 Ischaemic stroke Diseases 0.000 claims description 3
208000017442 Retinal disease Diseases 0.000 claims description 3
206010038923 Retinopathy Diseases 0.000 claims description 3
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
208000026106 cerebrovascular disease Diseases 0.000 claims description 3
208000029078 coronary artery disease Diseases 0.000 claims description 3
229940125532 enzyme inhibitor Drugs 0.000 claims description 3
RGMNKANICOKRFW-UHFFFAOYSA-N ethyl 2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate Chemical compound O=C1N2C=C(C(=O)OCC)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 RGMNKANICOKRFW-UHFFFAOYSA-N 0.000 claims description 3
208000019622 heart disease Diseases 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229940125396 insulin Drugs 0.000 claims description 3
230000000302 ischemic effect Effects 0.000 claims description 3
QRBKGBJKWUCYRX-UHFFFAOYSA-N n-[2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-2,3-dihydroxypropanamide Chemical compound O=C1N2C=C(NC(=O)C(O)CO)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 QRBKGBJKWUCYRX-UHFFFAOYSA-N 0.000 claims description 3
KOZNWTGOMQFSMO-UHFFFAOYSA-N n-[2-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-2-hydroxyacetamide Chemical compound O=C1N2C=C(NC(=O)CO)C=CC2=NN1CC1=CC=C(Cl)C(C(F)(F)F)=C1 KOZNWTGOMQFSMO-UHFFFAOYSA-N 0.000 claims description 3
239000000651 prodrug Substances 0.000 claims description 3
229940002612 prodrug Drugs 0.000 claims description 3
230000002829 reductive effect Effects 0.000 claims description 3
AGMAOISHIAVAQT-UHFFFAOYSA-N butyl n-[2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-6-yl]carbamate Chemical compound O=C1N2C=C(NC(=O)OCCCC)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 AGMAOISHIAVAQT-UHFFFAOYSA-N 0.000 claims description 2
HCEBEAXUZILJMF-UHFFFAOYSA-N tert-butyl n-[2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-6-yl]carbamate Chemical compound O=C1N2C=C(NC(=O)OC(C)(C)C)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 HCEBEAXUZILJMF-UHFFFAOYSA-N 0.000 claims description 2
230000001052 transient effect Effects 0.000 claims description 2
208000015669 capillary disease Diseases 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
QSJOHKPAPMCPSV-LBPRGKRZSA-N n-butyl-2-[(1s)-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound C1([C@H](C)N2N=C3C=CC(=CN3C2=O)C(=O)NCCCC)=CC=C(F)C(C(F)(F)F)=C1 QSJOHKPAPMCPSV-LBPRGKRZSA-N 0.000 claims 1
230000001404 mediated effect Effects 0.000 abstract description 12
208000001145 Metabolic Syndrome Diseases 0.000 abstract description 9
201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 abstract description 8
150000002632 lipids Chemical class 0.000 abstract description 8
208000024172 Cardiovascular disease Diseases 0.000 abstract description 6
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238000011321 prophylaxis Methods 0.000 abstract 1
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108010087894 Fatty acid desaturases Proteins 0.000 description 54
102100028897 Stearoyl-CoA desaturase Human genes 0.000 description 53
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
125000000623 heterocyclic group Chemical group 0.000 description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
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125000004181 carboxyalkyl group Chemical group 0.000 description 22
125000004093 cyano group Chemical group *C#N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
150000001412 amines Chemical class 0.000 description 18
125000004432 carbon atom Chemical group C* 0.000 description 18
230000000694 effects Effects 0.000 description 18
125000000392 cycloalkenyl group Chemical group 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
235000014113 dietary fatty acids Nutrition 0.000 description 15
239000000194 fatty acid Substances 0.000 description 15
229930195729 fatty acid Natural products 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
208000035475 disorder Diseases 0.000 description 11
239000000243 solution Substances 0.000 description 11
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
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125000004442 acylamino group Chemical group 0.000 description 9
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125000005110 aryl thio group Chemical group 0.000 description 9
125000004104 aryloxy group Chemical group 0.000 description 9
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125000000468 ketone group Chemical group 0.000 description 9
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125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
150000003573 thiols Chemical class 0.000 description 9
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 9
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HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 8
125000005368 heteroarylthio group Chemical group 0.000 description 8
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125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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125000005843 halogen group Chemical group 0.000 description 7
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
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YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 4
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