MX2007002050A

MX2007002050A - Compuestos de triazolopiridina.

Compuestos de triazolopiridina.

Info

Publication number: MX2007002050A
Authority: MX; Mexico
Prior art keywords: alkyl; triazolo; crc6; difluorophenyl; group
Prior art date: 2004-08-18

Application number

MX2007002050A

Other languages

English (en)

Spanish (es)

Inventor

Shaun Raj Selness

Li Xing

Paul V Rucker

Kevin De Wayne Jerome

John Edward Baldus

Original Assignee

Pharmacia & Upjohn Co Llc

Priority date

2004-08-18

Filing date

2005-08-08

Publication date

2007-03-29

2005-08-08 Application filed by Pharmacia & Upjohn Co Llc filed Critical Pharmacia & Upjohn Co Llc

2007-03-29 Publication of MX2007002050A publication Critical patent/MX2007002050A/es

Links

150000008523 triazolopyridines Chemical class 0.000 title abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 192
102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims abstract description 43
108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 43
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
-1 C-alkyl C6 Chemical group 0.000 claims description 200
125000000217 alkyl group Chemical group 0.000 claims description 68
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 67
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 54
125000001424 substituent group Chemical group 0.000 claims description 52
125000000623 heterocyclic group Chemical group 0.000 claims description 44
125000005843 halogen group Chemical group 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 39
125000000753 cycloalkyl group Chemical group 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
125000001072 heteroaryl group Chemical group 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
230000001404 mediated effect Effects 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 22
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 18
125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 17
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 17
229940095102 methyl benzoate Drugs 0.000 claims description 17
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 10
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
206010003246 arthritis Diseases 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
208000027866 inflammatory disease Diseases 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
YVKDKDPVFHFMDD-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfanyl-3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridine;hydrochloride Chemical compound Cl.C=1N2C(C(C)C)=NN=C2C=CC=1SC1=CC=C(F)C=C1F YVKDKDPVFHFMDD-UHFFFAOYSA-N 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 5
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
125000004950 trifluoroalkyl group Chemical group 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
JCWUBCGUZQIECK-UHFFFAOYSA-N 6-[(2,4-difluorophenyl)methyl]-3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1CC1=CC=C(F)C=C1F JCWUBCGUZQIECK-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
NUFGSMMBYKSSTF-UHFFFAOYSA-N 4-[6-[(2,4-difluorophenyl)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN=C2N1C=C(CC=1C(=CC(F)=CC=1)F)C=C2 NUFGSMMBYKSSTF-UHFFFAOYSA-N 0.000 claims description 3
DPIYTCQGFANXRZ-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfanyl-3-(2-methylpent-4-en-2-yl)-[1,2,4]triazolo[4,3-a]pyridine;hydrochloride Chemical compound Cl.C=1N2C(C(C)(CC=C)C)=NN=C2C=CC=1SC1=CC=C(F)C=C1F DPIYTCQGFANXRZ-UHFFFAOYSA-N 0.000 claims description 3
HHRGFPNZQLCRDG-UHFFFAOYSA-N 6-[(2,4-difluorophenyl)methyl]-3-(4-ethenylphenyl)-[1,2,4]triazolo[4,3-a]pyridine Chemical compound FC1=CC(F)=CC=C1CC1=CN2C(C=3C=CC(C=C)=CC=3)=NN=C2C=C1 HHRGFPNZQLCRDG-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
DPODWJFRTOTOTG-UHFFFAOYSA-N 3-propan-2-yl-6-(2,4,6-trichlorophenyl)sulfanyl-[1,2,4]triazolo[4,3-a]pyridine;hydrochloride Chemical compound Cl.C=1N2C(C(C)C)=NN=C2C=CC=1SC1=C(Cl)C=C(Cl)C=C1Cl DPODWJFRTOTOTG-UHFFFAOYSA-N 0.000 claims description 2
GUCIUZDOCMFAAG-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfanyl-3-(1-methylcyclopropyl)-[1,2,4]triazolo[4,3-a]pyridine;hydrochloride Chemical compound Cl.N=1N=C2C=CC(SC=3C(=CC(F)=CC=3)F)=CN2C=1C1(C)CC1 GUCIUZDOCMFAAG-UHFFFAOYSA-N 0.000 claims description 2
BGCAUSDTMWKUSC-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfanyl-3-(4-ethenyl-2-methylphenyl)-[1,2,4]triazolo[4,3-a]pyridine;hydrochloride Chemical compound Cl.CC1=CC(C=C)=CC=C1C1=NN=C2N1C=C(SC=1C(=CC(F)=CC=1)F)C=C2 BGCAUSDTMWKUSC-UHFFFAOYSA-N 0.000 claims description 2
MDAARQAVHVGFFW-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1S(=O)(=O)C1=CC=C(F)C=C1F MDAARQAVHVGFFW-UHFFFAOYSA-N 0.000 claims description 2
QSKACMDRLHDMNM-UHFFFAOYSA-N 6-[(2-fluorophenyl)methyl]-3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1CC1=CC=CC=C1F QSKACMDRLHDMNM-UHFFFAOYSA-N 0.000 claims description 2
OVPBTTOQTOXACP-UHFFFAOYSA-N 6-[(3-fluorophenyl)methyl]-3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1CC1=CC=CC(F)=C1 OVPBTTOQTOXACP-UHFFFAOYSA-N 0.000 claims description 2
XBMYTUROAAOLKV-UHFFFAOYSA-N 6-[(4-fluorophenyl)methyl]-3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1CC1=CC=C(F)C=C1 XBMYTUROAAOLKV-UHFFFAOYSA-N 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000002346 iodo group Chemical group I* 0.000 claims description 2
DUOWALCMAPFRMM-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfinyl-3-propan-2-yl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1S(=O)C1=CC=C(F)C=C1F DUOWALCMAPFRMM-UHFFFAOYSA-N 0.000 claims 1
AYPKFZUTFKDPBV-UHFFFAOYSA-N FC1=CC(=C(C=C1)SC1=CC=CC=2N1C(=NN2)C(C)C)C(F)(F)F Chemical compound FC1=CC(=C(C=C1)SC1=CC=CC=2N1C(=NN2)C(C)C)C(F)(F)F AYPKFZUTFKDPBV-UHFFFAOYSA-N 0.000 claims 1
150000003973 alkyl amines Chemical class 0.000 claims 1
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
238000000034 method Methods 0.000 abstract description 76
102100040247 Tumor necrosis factor Human genes 0.000 abstract description 47
239000000203 mixture Substances 0.000 abstract description 41
101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 abstract description 36
230000000694 effects Effects 0.000 abstract description 29
239000000543 intermediate Substances 0.000 abstract description 23
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 abstract description 4
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229910001868 water Inorganic materials 0.000 description 137
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 131
239000007787 solid Substances 0.000 description 128
238000006243 chemical reaction Methods 0.000 description 124
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
239000000243 solution Substances 0.000 description 110
238000002360 preparation method Methods 0.000 description 81
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
238000005160 1H NMR spectroscopy Methods 0.000 description 73
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238000001514 detection method Methods 0.000 description 58
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235000019198 oils Nutrition 0.000 description 38
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
239000012267 brine Substances 0.000 description 33
229960004132 diethyl ether Drugs 0.000 description 33
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238000006467 substitution reaction Methods 0.000 description 30
229910052736 halogen Inorganic materials 0.000 description 28
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239000000377 silicon dioxide Substances 0.000 description 24
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150000002367 halogens Chemical class 0.000 description 19
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102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 18
125000004432 carbon atom Chemical group C* 0.000 description 17
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
108010037462 Cyclooxygenase 2 Proteins 0.000 description 16
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
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