CA2685952C

CA2685952C - N- [6-amino-5- (phenyl) pyrazin-2-yl] -isoxazole-4-carboxamide derivatives and related compounds as nav1.8 channel modulators for the treatment of pain

N- [6-amino-5- (phenyl) pyrazin-2-yl] -isoxazole-4-carboxamide derivatives and related compounds as nav1.8 channel modulators for the treatment of pain Download PDF

Info

Publication number: CA2685952C
Authority: CA; Canada
Prior art keywords: amino; phenyl; pain; pyrazin; carboxamide
Prior art date: 2007-05-03
Legal status : Expired - Fee Related

Application number

CA2685952A

Other languages

English (en)

French (fr)

Other versions

CA2685952A1 (en

Inventor

Mark Ian Kemp

Current Assignee

Pfizer Ltd Great Britain

Original Assignee

Pfizer Ltd Great Britain

Priority date

2007-05-03

Filing date

2008-04-21

Publication date

2012-03-13

2008-04-21 Application filed by Pfizer Ltd Great Britain filed Critical Pfizer Ltd Great Britain

2008-11-13 Publication of CA2685952A1 publication Critical patent/CA2685952A1/en

2012-03-13 Application granted granted Critical

2012-03-13 Publication of CA2685952C publication Critical patent/CA2685952C/en

Status Expired - Fee Related legal-status Critical Current

2028-04-21 Anticipated expiration legal-status Critical

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 189
208000002193 Pain Diseases 0.000 title claims abstract description 80
238000011282 treatment Methods 0.000 title claims abstract description 19
LMSYLDQTOHNDAC-UHFFFAOYSA-N n-(6-amino-5-phenylpyrazin-2-yl)-1,2-oxazole-4-carboxamide Chemical class C=1N=C(C=2C=CC=CC=2)C(N)=NC=1NC(=O)C=1C=NOC=1 LMSYLDQTOHNDAC-UHFFFAOYSA-N 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 46
239000012453 solvate Substances 0.000 claims abstract description 30
-1 N-{6-Amino-5-[2-(trifluoromethoxy)phenyl]pyrazin-2-yl}-1-isopropyl-1H-pyrazole-carboxamide Chemical compound 0.000 claims description 37
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
201000010099 disease Diseases 0.000 claims description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 13
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
HYQNDXAIULPCIX-UHFFFAOYSA-N n-[6-amino-5-[5-chloro-2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-3-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC=C1C(=O)NC1=CN=C(C=2C(=CC=C(Cl)C=2)OC(F)(F)F)C(N)=N1 HYQNDXAIULPCIX-UHFFFAOYSA-N 0.000 claims description 2
NILPVXSKYCXTTM-UHFFFAOYSA-N n-[6-amino-5-[5-fluoro-2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-3-(trifluoromethyl)-1,2-oxazole-4-carboxamide Chemical compound C=1N=C(C=2C(=CC=C(F)C=2)OC(F)(F)F)C(N)=NC=1NC(=O)C1=CON=C1C(F)(F)F NILPVXSKYCXTTM-UHFFFAOYSA-N 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 6
241000124008 Mammalia Species 0.000 claims 2
239000013543 active substance Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
CEJKMICKPLFCPJ-UHFFFAOYSA-N n-[6-amino-5-[2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-2-ethylpyrazole-3-carboxamide Chemical compound CCN1N=CC=C1C(=O)NC1=CN=C(C=2C(=CC=CC=2)OC(F)(F)F)C(N)=N1 CEJKMICKPLFCPJ-UHFFFAOYSA-N 0.000 claims 1
IYGNIHHQJIPWBL-UHFFFAOYSA-N n-[6-amino-5-[2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-3-(methoxymethyl)-1,2-oxazole-4-carboxamide Chemical compound COCC1=NOC=C1C(=O)NC1=CN=C(C=2C(=CC=CC=2)OC(F)(F)F)C(N)=N1 IYGNIHHQJIPWBL-UHFFFAOYSA-N 0.000 claims 1
XLMSWOYFOPOIGI-UHFFFAOYSA-N n-[6-amino-5-[2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-3-(trifluoromethyl)-1,2-oxazole-4-carboxamide Chemical compound C=1N=C(C=2C(=CC=CC=2)OC(F)(F)F)C(N)=NC=1NC(=O)C1=CON=C1C(F)(F)F XLMSWOYFOPOIGI-UHFFFAOYSA-N 0.000 claims 1
FPEVBIZIYIUURP-UHFFFAOYSA-N n-[6-amino-5-[2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-3-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC=C1C(=O)NC1=CN=C(C=2C(=CC=CC=2)OC(F)(F)F)C(N)=N1 FPEVBIZIYIUURP-UHFFFAOYSA-N 0.000 claims 1
SZHKZPFWVWUNQO-UHFFFAOYSA-N n-[6-amino-5-[2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-5-(methoxymethyl)-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2N=C(N)C(=NC=2)C=2C(=CC=CC=2)OC(F)(F)F)=C1COC SZHKZPFWVWUNQO-UHFFFAOYSA-N 0.000 claims 1
KXUMBZHAWOLSKD-UHFFFAOYSA-N n-[6-amino-5-[2-(trifluoromethyl)phenyl]pyrazin-2-yl]-3-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC=C1C(=O)NC1=CN=C(C=2C(=CC=CC=2)C(F)(F)F)C(N)=N1 KXUMBZHAWOLSKD-UHFFFAOYSA-N 0.000 claims 1
UTHRQYLTFYBSPN-UHFFFAOYSA-N n-[6-amino-5-[5-chloro-2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-2-methylpyrazole-3-carboxamide Chemical compound CN1N=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(Cl)C=2)OC(F)(F)F)C(N)=N1 UTHRQYLTFYBSPN-UHFFFAOYSA-N 0.000 claims 1
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MXASHBCILUYQJY-UHFFFAOYSA-N n-[6-amino-5-[5-ethoxy-2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-2-methylpyrazole-3-carboxamide Chemical compound CCOC1=CC=C(OC(F)(F)F)C(C=2C(=NC(NC(=O)C=3N(N=CC=3)C)=CN=2)N)=C1 MXASHBCILUYQJY-UHFFFAOYSA-N 0.000 claims 1
MIPDTACEPTYIGK-UHFFFAOYSA-N n-[6-amino-5-[5-ethoxy-2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-3-methyl-1,2-oxazole-4-carboxamide Chemical compound CCOC1=CC=C(OC(F)(F)F)C(C=2C(=NC(NC(=O)C=3C(=NOC=3)C)=CN=2)N)=C1 MIPDTACEPTYIGK-UHFFFAOYSA-N 0.000 claims 1
HZAGYNWZXLPKOA-UHFFFAOYSA-N n-[6-amino-5-[5-fluoro-2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-2-methylpyrazole-3-carboxamide Chemical compound CN1N=CC=C1C(=O)NC1=CN=C(C=2C(=CC=C(F)C=2)OC(F)(F)F)C(N)=N1 HZAGYNWZXLPKOA-UHFFFAOYSA-N 0.000 claims 1
KVGZRUOOUZTLJL-UHFFFAOYSA-N n-[6-amino-5-[5-fluoro-2-(trifluoromethoxy)phenyl]pyrazin-2-yl]-3-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=NOC=C1C(=O)NC1=CN=C(C=2C(=CC=C(F)C=2)OC(F)(F)F)C(N)=N1 KVGZRUOOUZTLJL-UHFFFAOYSA-N 0.000 claims 1
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CKJKRXIOOOTHOP-UHFFFAOYSA-N n-[6-amino-5-[5-fluoro-2-(trifluoromethyl)phenyl]pyrazin-2-yl]-3-(trifluoromethyl)-1,2-oxazole-4-carboxamide Chemical compound C=1N=C(C=2C(=CC=C(F)C=2)C(F)(F)F)C(N)=NC=1NC(=O)C1=CON=C1C(F)(F)F CKJKRXIOOOTHOP-UHFFFAOYSA-N 0.000 claims 1
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