TW200418803A - Anilinopyrazole derivatives useful for the treatment of diabetes - Google Patents

Info

Publication number

TW200418803A

TW200418803A TW092133242A TW92133242A TW200418803A TW 200418803 A TW200418803 A TW 200418803A TW 092133242 A TW092133242 A TW 092133242A TW 92133242 A TW92133242 A TW 92133242A TW 200418803 A TW200418803 A TW 200418803A

Authority

TW

Taiwan

Prior art keywords

group

crc6

alkyl

alkoxy

optionally substituted

Prior art date

2002-11-27

Links

• Espacenet
• Global Dossier
• Discuss

• 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 46
• 238000011282 treatment Methods 0.000 title claims description 27
• CMAOIURPBUCSJE-UHFFFAOYSA-N n-phenyl-1h-pyrazol-5-amine Chemical class C=1C=CC=CC=1NC=1C=CNN=1 CMAOIURPBUCSJE-UHFFFAOYSA-N 0.000 title abstract 2
• 238000000034 method Methods 0.000 claims abstract description 77
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• -1 10-alkylthio Chemical group 0.000 claims description 357
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 252
• 150000001875 compounds Chemical class 0.000 claims description 178
• 125000000217 alkyl group Chemical group 0.000 claims description 140
• 125000003545 alkoxy group Chemical group 0.000 claims description 126
• 239000002253 acid Substances 0.000 claims description 97
• 239000000203 mixture Substances 0.000 claims description 96
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 77
• 125000001424 substituent group Chemical group 0.000 claims description 68
• 239000005711 Benzoic acid Substances 0.000 claims description 61
• 235000010233 benzoic acid Nutrition 0.000 claims description 60
• 125000003277 amino group Chemical group 0.000 claims description 55
• 125000005843 halogen group Chemical group 0.000 claims description 53
• 230000002079 cooperative effect Effects 0.000 claims description 51
• 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 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 43
• 150000001412 amines Chemical class 0.000 claims description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 38
• 239000003814 drug Substances 0.000 claims description 37
• 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 35
• 125000004414 alkyl thio group Chemical group 0.000 claims description 33
• XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 claims description 30
• 229940079593 drug Drugs 0.000 claims description 30
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 30
• 239000008103 glucose Substances 0.000 claims description 30
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 28
• 238000005859 coupling reaction Methods 0.000 claims description 28
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
• 229940125396 insulin Drugs 0.000 claims description 24
• 102000004877 Insulin Human genes 0.000 claims description 23
• 108090001061 Insulin Proteins 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 20
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 10
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 10
• 239000000883 anti-obesity agent Substances 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 239000007789 gas Substances 0.000 claims description 9
• 229940122355 Insulin sensitizer Drugs 0.000 claims description 8
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 8
• 210000004369 blood Anatomy 0.000 claims description 8
• 239000008280 blood Substances 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 230000003914 insulin secretion Effects 0.000 claims description 8
• 239000008177 pharmaceutical agent Substances 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 7
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 6
• PUFWGUZSDHANBX-UHFFFAOYSA-N 1-phenyl-9h-fluorene Chemical compound C=12CC3=CC=CC=C3C2=CC=CC=1C1=CC=CC=C1 PUFWGUZSDHANBX-UHFFFAOYSA-N 0.000 claims description 6
• 229940122199 Insulin secretagogue Drugs 0.000 claims description 6
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 210000004185 liver Anatomy 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 5
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 5
• 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 5
• 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims description 5
• 230000008878 coupling Effects 0.000 claims description 5
• 238000010168 coupling process Methods 0.000 claims description 5
• 150000002632 lipids Chemical class 0.000 claims description 5
• 238000007639 printing Methods 0.000 claims description 5
• 229960002101 secretin Drugs 0.000 claims description 5
• 125000003944 tolyl group Chemical group 0.000 claims description 5
• 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 4
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 4
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 4
• 102100037505 Secretin Human genes 0.000 claims description 4
• 108010086019 Secretin Proteins 0.000 claims description 4
• WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• BNYHRGTXRPWASY-UHFFFAOYSA-N nonylsulfonylurea Chemical compound CCCCCCCCCS(=O)(=O)NC(N)=O BNYHRGTXRPWASY-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 229920000642 polymer Polymers 0.000 claims description 4
• OWMZNFCDEHGFEP-NFBCVYDUSA-N secretin human Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(N)=O)[C@@H](C)O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)C1=CC=CC=C1 OWMZNFCDEHGFEP-NFBCVYDUSA-N 0.000 claims description 4
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 3
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• 229940100389 Sulfonylurea Drugs 0.000 claims description 3
• 230000002159 abnormal effect Effects 0.000 claims description 3
• 230000005856 abnormality Effects 0.000 claims description 3
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
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• 230000000670 limiting effect Effects 0.000 claims description 3
• 125000006178 methyl benzyl group Chemical group 0.000 claims description 3
• 235000001968 nicotinic acid Nutrition 0.000 claims description 3
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• 150000003254 radicals Chemical class 0.000 claims description 3
• 230000000580 secretagogue effect Effects 0.000 claims description 3
• YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 208000011580 syndromic disease Diseases 0.000 claims description 3
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
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• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
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• VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 2
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• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 2
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• OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
• DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1