JP2010504280A5 - - Google Patents

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Publication number: JP2010504280A5
Authority: JP; Japan
Prior art keywords: substituted; unsubstituted; chloro; triazol; benzenesulfonamide
Prior art date: 2007-07-10
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.): Granted

Application number

JP2009520761A

Other languages

English (en)

Japanese (ja)

Other versions

JP5320291B2 (ja

JP2010504280A (ja

Filing date

2007-07-10

Publication date

2012-02-16

2007-07-10 Application filed filed Critical

2007-07-10 Priority claimed from PCT/US2007/015786 external-priority patent/WO2008008375A2/en

2010-02-12 Publication of JP2010504280A publication Critical patent/JP2010504280A/ja

2012-02-16 Publication of JP2010504280A5 publication Critical patent/JP2010504280A5/ja

2013-10-23 Application granted granted Critical

2013-10-23 Publication of JP5320291B2 publication Critical patent/JP5320291B2/ja

Status Active legal-status Critical Current

2027-07-10 Anticipated expiration legal-status Critical

Links

-1 T-Butyl Chemical group 0.000 claims 35
150000001875 compounds Chemical class 0.000 claims 28
125000000217 alkyl group Chemical group 0.000 claims 23
229910052739 hydrogen Inorganic materials 0.000 claims 22
239000001257 hydrogen Substances 0.000 claims 22
150000003839 salts Chemical class 0.000 claims 20
150000002431 hydrogen Chemical class 0.000 claims 19
125000003342 alkenyl group Chemical group 0.000 claims 18
125000000304 alkynyl group Chemical group 0.000 claims 18
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 17
125000003118 aryl group Chemical group 0.000 claims 16
125000000623 heterocyclic group Chemical group 0.000 claims 16
229910052736 halogen Inorganic materials 0.000 claims 13
150000002367 halogens Chemical class 0.000 claims 13
125000004429 atom Chemical group 0.000 claims 10
239000008194 pharmaceutical composition Substances 0.000 claims 10
125000004093 cyano group Chemical group *C#N 0.000 claims 5
201000010099 disease Diseases 0.000 claims 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
150000001408 amides Chemical class 0.000 claims 4
230000001404 mediated effect Effects 0.000 claims 4
102100022718 Atypical chemokine receptor 2 Human genes 0.000 claims 3
102100031151 C-C chemokine receptor type 2 Human genes 0.000 claims 3
101710149815 C-C chemokine receptor type 2 Proteins 0.000 claims 3
101000678892 Homo sapiens Atypical chemokine receptor 2 Proteins 0.000 claims 3
101000716070 Homo sapiens C-C chemokine receptor type 9 Proteins 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
SJCDBQHCQSIZHN-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxamide Chemical compound NC(=O)N1NNC=C1 SJCDBQHCQSIZHN-UHFFFAOYSA-N 0.000 claims 2
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 2
230000001105 regulatory effect Effects 0.000 claims 2
125000003107 substituted aryl group Chemical group 0.000 claims 2
XQQNPZZMXRJVDN-UHFFFAOYSA-N 3,4-dichloro-n-[5-chloro-2-[4-(1h-pyrazol-5-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]benzenesulfonamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=CN1C=1C=CNN=1 XQQNPZZMXRJVDN-UHFFFAOYSA-N 0.000 claims 1
FZFLWOHYWMSSFG-UHFFFAOYSA-N 4-chloro-n-[5-chloro-2-[4-(4-methyl-1h-pyrazol-5-yl)-1,2,4-triazol-3-yl]pyridin-3-yl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound CC1=CNN=C1N1C(C=2C(=CC(Cl)=CN=2)NS(=O)(=O)C=2C=C(C(Cl)=CC=2)C(F)(F)F)=NN=C1 FZFLWOHYWMSSFG-UHFFFAOYSA-N 0.000 claims 1
JELORYBSSKXTKS-UHFFFAOYSA-N 5-[3-[(4-tert-butylphenyl)sulfonylamino]-5-chloropyridin-2-yl]-n,n-dimethyl-4-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)N(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 JELORYBSSKXTKS-UHFFFAOYSA-N 0.000 claims 1
HMCRGZKZGJIKHJ-UHFFFAOYSA-N 5-[3-[(4-tert-butylphenyl)sulfonylamino]-5-chloropyridin-2-yl]-n-methyl-4-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)NC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 HMCRGZKZGJIKHJ-UHFFFAOYSA-N 0.000 claims 1
KPBBXPDMTLDHTE-UHFFFAOYSA-N 5-[3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]-5-methylpyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C=1C=C(Cl)C(C(F)(F)F)=CC=1S(=O)(=O)NC1=CC(C)=CN=C1C1=NN=C(C(N)=O)N1C=1C=CON=1 KPBBXPDMTLDHTE-UHFFFAOYSA-N 0.000 claims 1
QHAFGHWVHRRHSV-UHFFFAOYSA-N 5-[3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]-5-methylpyridin-2-yl]-4-phenyl-1,2,4-triazole-3-carboxamide Chemical compound C=1C=C(Cl)C(C(F)(F)F)=CC=1S(=O)(=O)NC1=CC(C)=CN=C1C1=NN=C(C(N)=O)N1C1=CC=CC=C1 QHAFGHWVHRRHSV-UHFFFAOYSA-N 0.000 claims 1
NUOLRQJDNCPPQU-UHFFFAOYSA-N 5-[5-chloro-3-[(3,4-dichlorophenyl)sulfonylamino]pyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)N)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 NUOLRQJDNCPPQU-UHFFFAOYSA-N 0.000 claims 1
CWEXICJJEOCLLQ-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)N)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 CWEXICJJEOCLLQ-UHFFFAOYSA-N 0.000 claims 1
SAIRUSJXGAIIKQ-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-(1,2-oxazol-3-yl)-n-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)NC(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 SAIRUSJXGAIIKQ-UHFFFAOYSA-N 0.000 claims 1
QDTKHLLJQIJDAD-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound CC(C)N1C(C(N)=O)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 QDTKHLLJQIJDAD-UHFFFAOYSA-N 0.000 claims 1
MYDSZQFQVRXQPG-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-n,n-dimethyl-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)N(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 MYDSZQFQVRXQPG-UHFFFAOYSA-N 0.000 claims 1
BTFFJIJPEWHEEM-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-n,n-dimethyl-4-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound CC(C)N1C(C(=O)N(C)C)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 BTFFJIJPEWHEEM-UHFFFAOYSA-N 0.000 claims 1
DDTYMWFASCHUPO-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-n-ethyl-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)NCC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 DDTYMWFASCHUPO-UHFFFAOYSA-N 0.000 claims 1
GUNCDSYWZPBVIR-UHFFFAOYSA-N 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-n-ethyl-n-methyl-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=CON=C1N1C(C(=O)N(C)CC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 GUNCDSYWZPBVIR-UHFFFAOYSA-N 0.000 claims 1
ZOPRRQNFZVBNDG-UHFFFAOYSA-N 5-[5-chloro-3-[[4-methyl-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=C(C(N)=O)N1C1=NOC=C1 ZOPRRQNFZVBNDG-UHFFFAOYSA-N 0.000 claims 1
201000001320 Atherosclerosis Diseases 0.000 claims 1
PYJQQZKGTZDDHZ-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)NC=1C(=NC=C(C=1)C)C1=NN=CN1C1CNCC1 Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC=1C(=NC=C(C=1)C)C1=NN=CN1C1CNCC1 PYJQQZKGTZDDHZ-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
208000009329 Graft vs Host Disease Diseases 0.000 claims 1
201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
206010063725 Idiopathic pneumonia syndrome Diseases 0.000 claims 1
208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 claims 1
BKAKNTTWTRQBBK-UHFFFAOYSA-N O=C(C1=NN=C(C(C=C2)=NC=C2Cl)N1C1=NOC=C1)N1CCOCC1 Chemical compound O=C(C1=NN=C(C(C=C2)=NC=C2Cl)N1C1=NOC=C1)N1CCOCC1 BKAKNTTWTRQBBK-UHFFFAOYSA-N 0.000 claims 1
208000008589 Obesity Diseases 0.000 claims 1
208000002193 Pain Diseases 0.000 claims 1
206010052779 Transplant rejections Diseases 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
230000001760 anti-analgesic effect Effects 0.000 claims 1
230000003110 anti-inflammatory effect Effects 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
125000002837 carbocyclic group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
206010012601 diabetes mellitus Diseases 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
VXHXALJHPTYTDH-UHFFFAOYSA-N ethyl 5-[3-[(4-tert-butylphenyl)sulfonylamino]-5-chloropyridin-2-yl]-4-propan-2-yl-1,2,4-triazole-3-carboxylate Chemical compound CC(C)N1C(C(=O)OCC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 VXHXALJHPTYTDH-UHFFFAOYSA-N 0.000 claims 1
LWNVJYPBMIIDOF-UHFFFAOYSA-N ethyl 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-(1,2-oxazol-3-yl)-1,2,4-triazole-3-carboxylate Chemical compound C1=CON=C1N1C(C(=O)OCC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 LWNVJYPBMIIDOF-UHFFFAOYSA-N 0.000 claims 1
PWQMLLBKSFCCRB-UHFFFAOYSA-N ethyl 5-[5-chloro-3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]-4-propan-2-yl-1,2,4-triazole-3-carboxylate Chemical compound CC(C)N1C(C(=O)OCC)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 PWQMLLBKSFCCRB-UHFFFAOYSA-N 0.000 claims 1
208000024908 graft versus host disease Diseases 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 claims 1
208000007915 ichthyosis prematurity syndrome Diseases 0.000 claims 1
208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
201000006417 multiple sclerosis Diseases 0.000 claims 1
JTDBSXSLPVDHRS-UHFFFAOYSA-N n-[2-(5-amino-4-propan-2-yl-1,2,4-triazol-3-yl)-5-chloropyridin-3-yl]-4-chloro-3-(trifluoromethyl)benzenesulfonamide Chemical compound CC(C)N1C(N)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 JTDBSXSLPVDHRS-UHFFFAOYSA-N 0.000 claims 1
BLTWVOMRRFJFON-UHFFFAOYSA-N n-[2-(5-amino-4-propan-2-yl-1,2,4-triazol-3-yl)-5-chloropyridin-3-yl]-4-tert-butylbenzenesulfonamide Chemical compound CC(C)N1C(N)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 BLTWVOMRRFJFON-UHFFFAOYSA-N 0.000 claims 1
ZHABSIKVUSRSKW-UHFFFAOYSA-N n-[2-[4-(4-bromo-1h-pyrazol-5-yl)-1,2,4-triazol-3-yl]-5-chloropyridin-3-yl]-3,4-dichlorobenzenesulfonamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=CN1C1=NNC=C1Br ZHABSIKVUSRSKW-UHFFFAOYSA-N 0.000 claims 1
IUCAQAZBATXHQF-UHFFFAOYSA-N n-[2-[5-bromo-4-(1,2-oxazol-3-yl)-1,2,4-triazol-3-yl]-5-chloropyridin-3-yl]-4-chloro-3-(trifluoromethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=NC=C(Cl)C=2)C=2N(C(Br)=NN=2)C2=NOC=C2)=C1 IUCAQAZBATXHQF-UHFFFAOYSA-N 0.000 claims 1
WLIXWPBIQOBJGW-UHFFFAOYSA-N n-[2-[5-bromo-4-(4-bromo-1h-pyrazol-5-yl)-1,2,4-triazol-3-yl]-5-chloropyridin-3-yl]-3,4-dichlorobenzenesulfonamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1S(=O)(=O)NC1=CC(Cl)=CN=C1C1=NN=C(Br)N1C1=NNC=C1Br WLIXWPBIQOBJGW-UHFFFAOYSA-N 0.000 claims 1
MCUNGNKSMZSFRI-UHFFFAOYSA-N n-[5-[3-[(4-tert-butylphenyl)sulfonylamino]-5-chloropyridin-2-yl]-4-propan-2-yl-1,2,4-triazol-3-yl]acetamide Chemical compound CC(C)N1C(NC(C)=O)=NN=C1C1=NC=C(Cl)C=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 MCUNGNKSMZSFRI-UHFFFAOYSA-N 0.000 claims 1
201000001119 neuropathy Diseases 0.000 claims 1
230000007823 neuropathy Effects 0.000 claims 1
235000020824 obesity Nutrition 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
208000033808 peripheral neuropathy Diseases 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
208000005069 pulmonary fibrosis Diseases 0.000 claims 1
201000002793 renal fibrosis Diseases 0.000 claims 1
208000037803 restenosis Diseases 0.000 claims 1
206010039073 rheumatoid arthritis Diseases 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
229940124530 sulfonamide Drugs 0.000 claims 1
230000000699 topical effect Effects 0.000 claims 1

JP2009520761A 2006-07-14 2007-07-10 トリアゾリルピリジルベンゼンスルホンアミド類 Active JP5320291B2 (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US83104206P	2006-07-14	2006-07-14
US60/831,042		2006-07-14
US94585407P	2007-06-22	2007-06-22
US60/945,854		2007-06-22
PCT/US2007/015786 WO2008008375A2 (en)	2006-07-14	2007-07-10	Triazolyl pyridyl benzenesulfonamides as ccr2 or ccr9 modulators for the treatment of inflammation

Publications (3)

Publication Number	Publication Date
JP2010504280A JP2010504280A (ja)	2010-02-12
JP2010504280A5 true JP2010504280A5 (2)	2012-02-16
JP5320291B2 JP5320291B2 (ja)	2013-10-23

Family

ID=38670575

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2009520761A Active JP5320291B2 (ja)	2006-07-14	2007-07-10	トリアゾリルピリジルベンゼンスルホンアミド類

Country Status (10)

Country	Link
US (2)	US7683176B2 (2)
EP (1)	EP2049515B1 (2)
JP (1)	JP5320291B2 (2)
CN (1)	CN101511800B (2)
AT (1)	ATE496905T1 (2)
AU (1)	AU2007272972B2 (2)
CA (1)	CA2657670C (2)
DE (1)	DE602007012261D1 (2)
ES (2)	ES2360741T3 (2)
WO (1)	WO2008008375A2 (2)

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