CA2574279A1

CA2574279A1 - Heterocyclic compounds as pharmaceutical agents

Heterocyclic compounds as pharmaceutical agents Download PDF

Info

Publication number: CA2574279A1
Authority: CA; Canada
Prior art keywords: optionally substituted; substituted; heterocyclyl; heteroaryl; aryl
Prior art date: 2004-08-10
Legal status : Abandoned

Application number

CA002574279A

Other languages

English (en)

French (fr)

Inventor

Richard Martin

Brenton Todd Flatt

Jeffrey Dean Kahl

Current Assignee

Exelixis Inc

Original Assignee

Individual

Priority date

2004-08-10

Filing date

2005-08-09

Publication date

2006-02-23

2005-08-09 Application filed by Individual filed Critical Individual

2006-02-23 Publication of CA2574279A1 publication Critical patent/CA2574279A1/en

Status Abandoned legal-status Critical Current

Links

150000002391 heterocyclic compounds Chemical class 0.000 title description 3
239000008177 pharmaceutical agent Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 189
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 99
239000000203 mixture Substances 0.000 claims abstract description 97
238000000034 method Methods 0.000 claims abstract description 74
230000000694 effects Effects 0.000 claims abstract description 62
201000010099 disease Diseases 0.000 claims abstract description 51
208000035475 disorder Diseases 0.000 claims abstract description 48
208000024891 symptom Diseases 0.000 claims abstract description 26
125000001072 heteroaryl group Chemical group 0.000 claims description 263
125000000623 heterocyclic group Chemical group 0.000 claims description 263
125000003710 aryl alkyl group Chemical group 0.000 claims description 233
125000004475 heteroaralkyl group Chemical group 0.000 claims description 226
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 211
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 211
125000005843 halogen group Chemical group 0.000 claims description 190
125000000217 alkyl group Chemical group 0.000 claims description 186
125000004093 cyano group Chemical group *C#N 0.000 claims description 184
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 182
125000002577 pseudohalo group Chemical group 0.000 claims description 175
125000003118 aryl group Chemical group 0.000 claims description 174
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 172
125000001424 substituent group Chemical group 0.000 claims description 162
125000000753 cycloalkyl group Chemical group 0.000 claims description 161
125000001188 haloalkyl group Chemical group 0.000 claims description 148
229910052739 hydrogen Inorganic materials 0.000 claims description 96
239000001257 hydrogen Substances 0.000 claims description 96
108020005497 Nuclear hormone receptor Proteins 0.000 claims description 89
125000003107 substituted aryl group Chemical group 0.000 claims description 89
108020004017 nuclear receptors Proteins 0.000 claims description 87
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 82
125000000547 substituted alkyl group Chemical group 0.000 claims description 71
-1 heterycyclylalkyl Chemical group 0.000 claims description 68
125000005017 substituted alkenyl group Chemical group 0.000 claims description 64
125000003342 alkenyl group Chemical group 0.000 claims description 62
125000000304 alkynyl group Chemical group 0.000 claims description 58
125000004426 substituted alkynyl group Chemical group 0.000 claims description 57
102100038495 Bile acid receptor Human genes 0.000 claims description 50
101000603876 Homo sapiens Bile acid receptor Proteins 0.000 claims description 48
150000002431 hydrogen Chemical class 0.000 claims description 48
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 claims description 42
229910052757 nitrogen Inorganic materials 0.000 claims description 31
125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000002947 alkylene group Chemical group 0.000 claims description 21
229940107161 cholesterol Drugs 0.000 claims description 21
239000000556 agonist Substances 0.000 claims description 20
229910052717 sulfur Inorganic materials 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
239000003937 drug carrier Substances 0.000 claims description 17
239000005557 antagonist Substances 0.000 claims description 16
206010012601 diabetes mellitus Diseases 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 15
208000031226 Hyperlipidaemia Diseases 0.000 claims description 14
235000012000 cholesterol Nutrition 0.000 claims description 13
102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 12
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 12
125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 12
201000001320 Atherosclerosis Diseases 0.000 claims description 11
230000015572 biosynthetic process Effects 0.000 claims description 10
230000004060 metabolic process Effects 0.000 claims description 10
208000035150 Hypercholesterolemia Diseases 0.000 claims description 9
208000006575 hypertriglyceridemia Diseases 0.000 claims description 9
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
206010008635 Cholestasis Diseases 0.000 claims description 8
238000010521 absorption reaction Methods 0.000 claims description 8
239000003613 bile acid Substances 0.000 claims description 8
230000007870 cholestasis Effects 0.000 claims description 8
231100000359 cholestasis Toxicity 0.000 claims description 8
201000001421 hyperglycemia Diseases 0.000 claims description 8
208000032928 Dyslipidaemia Diseases 0.000 claims description 7
208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
206010049287 Lipodystrophy acquired Diseases 0.000 claims description 7
208000008589 Obesity Diseases 0.000 claims description 7
208000006132 lipodystrophy Diseases 0.000 claims description 7
235000020824 obesity Nutrition 0.000 claims description 7
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 6
239000012190 activator Substances 0.000 claims description 6
230000015556 catabolic process Effects 0.000 claims description 6
238000003786 synthesis reaction Methods 0.000 claims description 6
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 5
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230000029142 excretion Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
229930003427 Vitamin E Natural products 0.000 claims description 3
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 3
102000006255 nuclear receptors Human genes 0.000 claims description 3
235000019165 vitamin E Nutrition 0.000 claims description 3
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HLSDYWFUKOZJTE-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-(2,3-dihydroindol-1-ylmethylidene)-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN1C2=CC=CC=C2CC1 HLSDYWFUKOZJTE-UHFFFAOYSA-N 0.000 claims description 2
UYOKDJNIHORDNT-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-(2-phenylethyl)-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C1N(CC=2C=CC=CC=2)C(=O)C(CCC=2C=CC=CC=2)S1 UYOKDJNIHORDNT-UHFFFAOYSA-N 0.000 claims description 2
QRMFPGOYLMAMMW-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-(dimethylaminomethylidene)-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C1N(CC=2C=CC=CC=2)C(=O)C(=CN(C)C)S1 QRMFPGOYLMAMMW-UHFFFAOYSA-N 0.000 claims description 2
PZCIROBDGVLEIL-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-(furan-2-ylmethylidene)-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CC1=CC=CO1 PZCIROBDGVLEIL-UHFFFAOYSA-N 0.000 claims description 2
PDXNFKUZVGOMRC-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[(3-methoxy-n-methylanilino)methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)C1=CC=CC(OC)=C1 PDXNFKUZVGOMRC-UHFFFAOYSA-N 0.000 claims description 2
ZWQHCOQRXKFJGB-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[(4-methylpiperazin-1-yl)methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN1CCN(C)CC1 ZWQHCOQRXKFJGB-UHFFFAOYSA-N 0.000 claims description 2
VZGIJCXVUUINRV-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[(n-methylanilino)methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)C1=CC=CC=C1 VZGIJCXVUUINRV-UHFFFAOYSA-N 0.000 claims description 2
KNPWYRGLLCQAQC-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[[3-(dimethylamino)propyl-methylamino]methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C1N(CC=2C=CC=CC=2)C(=O)C(=CN(C)CCCN(C)C)S1 KNPWYRGLLCQAQC-UHFFFAOYSA-N 0.000 claims description 2
XABCMNNTHFJDCF-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[[4-(2-methoxyethoxy)-n-methylanilino]methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)C1=CC=C(OCCOC)C=C1 XABCMNNTHFJDCF-UHFFFAOYSA-N 0.000 claims description 2
BZXKLXUWHZDDTA-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[[benzyl(methyl)amino]methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)CC1=CC=CC=C1 BZXKLXUWHZDDTA-UHFFFAOYSA-N 0.000 claims description 2
GMUCPXKPCHHGMW-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-[[methyl(2-phenylethyl)amino]methylidene]-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)CCC1=CC=CC=C1 GMUCPXKPCHHGMW-UHFFFAOYSA-N 0.000 claims description 2
FTTCNMOCBHYESC-UHFFFAOYSA-N 2-[5-acetyl-2-(ethylamino)phenyl]imino-3-benzyl-5-phenacyl-1,3-thiazolidin-4-one Chemical compound CCNC1=CC=C(C(C)=O)C=C1N=C1N(CC=2C=CC=CC=2)C(=O)C(CC(=O)C=2C=CC=CC=2)S1 FTTCNMOCBHYESC-UHFFFAOYSA-N 0.000 claims description 2
HKFQHSDEEUNRTI-UHFFFAOYSA-N 3-[[3-benzyl-5-(2,3-dihydroindol-1-ylmethylidene)-4-oxo-1,3-thiazolidin-2-ylidene]amino]-4-(ethylamino)benzonitrile Chemical compound CCNC1=CC=C(C#N)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN1C2=CC=CC=C2CC1 HKFQHSDEEUNRTI-UHFFFAOYSA-N 0.000 claims description 2
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VOGNACRDQCXWGA-UHFFFAOYSA-N 3-[[3-benzyl-5-[(2-methoxy-n-methylanilino)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]-4-(ethylamino)benzonitrile Chemical compound CCNC1=CC=C(C#N)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)C1=CC=CC=C1OC VOGNACRDQCXWGA-UHFFFAOYSA-N 0.000 claims description 2
FRRBVAOXYDQYKI-UHFFFAOYSA-N 3-[[3-benzyl-5-[(4-methoxyanilino)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]-4-(ethylamino)benzonitrile Chemical compound CCNC1=CC=C(C#N)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CNC1=CC=C(OC)C=C1 FRRBVAOXYDQYKI-UHFFFAOYSA-N 0.000 claims description 2
MHGFLCUKXSCYJV-UHFFFAOYSA-N 3-[[3-benzyl-5-[(n-methylanilino)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]-4-(ethylamino)benzonitrile Chemical compound CCNC1=CC=C(C#N)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)C1=CC=CC=C1 MHGFLCUKXSCYJV-UHFFFAOYSA-N 0.000 claims description 2
DXNSGASFGISSOY-UHFFFAOYSA-N 3-[[3-benzyl-5-[[benzyl(methyl)amino]methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]amino]-4-(ethylamino)benzonitrile Chemical compound CCNC1=CC=C(C#N)C=C1N=C(S1)N(CC=2C=CC=CC=2)C(=O)C1=CN(C)CC1=CC=CC=C1 DXNSGASFGISSOY-UHFFFAOYSA-N 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
NQQMUAALTMRXKD-UHFFFAOYSA-N n-[4-[[5-(2,3-dihydroindol-1-ylmethylidene)-3-(furan-2-ylmethyl)-4-oxo-1,3-thiazolidin-2-ylidene]amino]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1N=C(S1)N(CC=2OC=CC=2)C(=O)C1=CN1C2=CC=CC=C2CC1 NQQMUAALTMRXKD-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000003112 inhibitor Substances 0.000 claims 15
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 14
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 12
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DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 3
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