JP2008505975A5 - - Google Patents

Info

Publication number

JP2008505975A5

JP2008505975A5 JP2007521571A JP2007521571A JP2008505975A5 JP 2008505975 A5 JP2008505975 A5 JP 2008505975A5 JP 2007521571 A JP2007521571 A JP 2007521571A JP 2007521571 A JP2007521571 A JP 2007521571A JP 2008505975 A5 JP2008505975 A5 JP 2008505975A5

Authority

JP

Japan

Prior art keywords

group

alkyl group

alkyl

independently

cycloalkyl

Prior art date

2005-07-12

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.)

Withdrawn

Links

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• 150000001875 compounds Chemical class 0.000 claims description 261
• -1 tautomers Substances 0.000 claims description 230
• 125000000217 alkyl group Chemical group 0.000 claims description 225
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 147
• 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims description 106
• 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims description 105
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 103
• 125000000623 heterocyclic group Chemical group 0.000 claims description 103
• 239000000203 mixture Substances 0.000 claims description 85
• 239000003112 inhibitor Substances 0.000 claims description 81
• 125000003342 alkenyl group Chemical group 0.000 claims description 76
• 125000000304 alkynyl group Chemical group 0.000 claims description 75
• 125000003118 aryl group Chemical group 0.000 claims description 75
• 238000000034 method Methods 0.000 claims description 65
• 239000003814 drug Substances 0.000 claims description 64
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 60
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims description 47
• 238000011282 treatment Methods 0.000 claims description 47
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
• 229910052717 sulfur Inorganic materials 0.000 claims description 42
• 229940079593 drug Drugs 0.000 claims description 41
• 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 40
• 208000024891 symptom Diseases 0.000 claims description 39
• 125000004043 oxo group Chemical group O=* 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 34
• 125000003277 amino group Chemical group 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
• 239000003795 chemical substances by application Substances 0.000 claims description 29
• 102100036968 Dipeptidyl peptidase 8 Human genes 0.000 claims description 28
• 101710087011 Dipeptidyl peptidase 8 Proteins 0.000 claims description 27
• 239000000556 agonist Substances 0.000 claims description 27
• 229940044601 receptor agonist Drugs 0.000 claims description 27
• 239000000018 receptor agonist Substances 0.000 claims description 27
• 239000003472 antidiabetic agent Substances 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 238000009472 formulation Methods 0.000 claims description 24
• OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims description 24
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 23
• 239000000883 anti-obesity agent Substances 0.000 claims description 23
• 229940125710 antiobesity agent Drugs 0.000 claims description 23
• 125000002837 carbocyclic group Chemical group 0.000 claims description 23
• 230000000694 effects Effects 0.000 claims description 23
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 21
• 102100031939 Erythropoietin Human genes 0.000 claims description 20
• 102000004877 Insulin Human genes 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 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 20
• 201000010099 disease Diseases 0.000 claims description 20
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• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 20
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• 238000002360 preparation method Methods 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 208000008589 Obesity Diseases 0.000 claims description 18
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 18
• 235000020824 obesity Nutrition 0.000 claims description 18
• 125000006239 protecting group Chemical group 0.000 claims description 18
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 17
• 102100036969 Dipeptidyl peptidase 9 Human genes 0.000 claims description 17
• 101710087005 Dipeptidyl peptidase 9 Proteins 0.000 claims description 17
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 101800000224 Glucagon-like peptide 1 Proteins 0.000 claims description 16
• 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 claims description 16
• 102100040918 Pro-glucagon Human genes 0.000 claims description 16
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 15
• 150000002632 lipids Chemical class 0.000 claims description 15
• 229940002612 prodrug Drugs 0.000 claims description 15
• 239000000651 prodrug Substances 0.000 claims description 15
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 14
• 102000023984 PPAR alpha Human genes 0.000 claims description 14
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
• 229940125708 antidiabetic agent Drugs 0.000 claims description 14
• 230000001404 mediated effect Effects 0.000 claims description 14
• 229940100389 Sulfonylurea Drugs 0.000 claims description 13
• 229910052740 iodine Inorganic materials 0.000 claims description 13
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
• 239000012453 solvate Substances 0.000 claims description 13
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims description 12
• 102400000326 Glucagon-like peptide 2 Human genes 0.000 claims description 12
• 101800000221 Glucagon-like peptide 2 Proteins 0.000 claims description 12
• 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 claims description 12
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 12
• 102000002808 Pituitary adenylate cyclase-activating polypeptide Human genes 0.000 claims description 12
• 108010004684 Pituitary adenylate cyclase-activating polypeptide Proteins 0.000 claims description 12
• 230000015572 biosynthetic process Effects 0.000 claims description 12
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
• TWSALRJGPBVBQU-PKQQPRCHSA-N glucagon-like peptide 2 Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(O)=O)[C@@H](C)CC)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=CC=C1 TWSALRJGPBVBQU-PKQQPRCHSA-N 0.000 claims description 12
• 230000002401 inhibitory effect Effects 0.000 claims description 12
• 206010022489 Insulin Resistance Diseases 0.000 claims description 11
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 11
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 11
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 239000000194 fatty acid Substances 0.000 claims description 11
• 229930195729 fatty acid Natural products 0.000 claims description 11
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 11
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 10
• 229940127003 anti-diabetic drug Drugs 0.000 claims description 10
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• 125000001041 indolyl group Chemical group 0.000 claims description 10
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• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical group FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 9
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 9
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 9
• 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 claims description 9
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• 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims description 9
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
• 235000012000 cholesterol Nutrition 0.000 claims description 9
• 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 description 9
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• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 9
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• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
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• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims description 8
• YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 8
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
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• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 8
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• DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims description 8
• HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 8
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• 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 claims description 7
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• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 7
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• 102100032879 Glucagon-like peptide 2 receptor Human genes 0.000 claims description 6
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• KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 claims description 6
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• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
• 239000000048 adrenergic agonist Substances 0.000 claims description 6
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