NO332420B1 - EP4 reseptor antagonister, andvendelse derav og farmasoytisk sammensetning inneholdende en slik forbindelse - Google Patents

EP4 reseptor antagonister, andvendelse derav og farmasoytisk sammensetning inneholdende en slik forbindelse Download PDF

Info

Publication number: NO332420B1
Authority: NO; Norway
Prior art keywords: methyl; furan; biphenyl; yloxymethyl; carboxylic acid
Prior art date: 2003-01-29

Application number

NO20053971A

Other languages

English (en)

Norwegian (no)

Other versions

NO20053971L (no

NO20053971D0 (no

Inventor

Alexander William Oxford

Neil Victor Harris

Keith Alfred James Stuttle

David Edward Clark

Kenneth Lyle Clark

Robert Alexander Coleman

Ricard Jon Davies

Gary Fenton

Georg Hynd

Christoper Gregory Newton

Jonathan Mark Sutton

Original Assignee

Asterand Uk Ltd

Priority date (The priority date 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 date listed.)

2003-01-29

Filing date

2005-08-25

Publication date

2012-09-17

2003-01-29 Priority claimed from GBGB0302094.8A external-priority patent/GB0302094D0/en

2005-08-25 Application filed by Asterand Uk Ltd filed Critical Asterand Uk Ltd

2005-08-25 Publication of NO20053971D0 publication Critical patent/NO20053971D0/no

2005-10-31 Publication of NO20053971L publication Critical patent/NO20053971L/no

2012-09-17 Publication of NO332420B1 publication Critical patent/NO332420B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 302
101150109738 Ptger4 gene Proteins 0.000 title claims description 10
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
239000002464 receptor antagonist Substances 0.000 title description 2
229940044551 receptor antagonist Drugs 0.000 title description 2
125000000217 alkyl group Chemical group 0.000 claims abstract description 52
125000003118 aryl group Chemical group 0.000 claims abstract description 45
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
125000002947 alkylene group Chemical group 0.000 claims abstract description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
239000001301 oxygen Substances 0.000 claims abstract description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 109
-1 3,5-Dimethyl-isoxazole-4-sulfonic acid [4-(4-difluoromethoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonyl]-amide Chemical compound 0.000 claims description 47
238000011282 treatment Methods 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 33
239000012453 solvate Substances 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 17
BRDLIFYQXFHZGL-UHFFFAOYSA-N 4-[[4-(4-methoxyphenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(O)=O)=C1 BRDLIFYQXFHZGL-UHFFFAOYSA-N 0.000 claims description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
208000002193 Pain Diseases 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
FHJBBZVBYBBOGN-UHFFFAOYSA-N 2-[5-methyl-4-[(4-phenylphenoxy)methyl]furan-2-yl]acetic acid Chemical compound O1C(CC(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C FHJBBZVBYBBOGN-UHFFFAOYSA-N 0.000 claims description 12
RMTSDFUOCODELU-UHFFFAOYSA-N 4-[[4-[4-(difluoromethoxy)phenyl]anilino]methyl]-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(CNC=2C=CC(=CC=2)C=2C=CC(OC(F)F)=CC=2)=C1C RMTSDFUOCODELU-UHFFFAOYSA-N 0.000 claims description 12
BKQUHGLCXLYUOD-UHFFFAOYSA-N 4-[[6-(4-methoxyphenyl)pyridin-3-yl]oxymethyl]-5-methylfuran-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(N=C1)=CC=C1OCC1=C(C)OC(C(O)=O)=C1 BKQUHGLCXLYUOD-UHFFFAOYSA-N 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
OWOSQIZIJWIJDC-UHFFFAOYSA-N 4-[[4-(5-methoxypyridin-2-yl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound N1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(O)=O)=C1 OWOSQIZIJWIJDC-UHFFFAOYSA-N 0.000 claims description 11
RVKMFHAPJHKOPR-UHFFFAOYSA-N n-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]-4-[[4-(4-methoxyphenyl)phenoxy]methyl]-5-methylfuran-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C2=C(ON=C2C)C)=C1 RVKMFHAPJHKOPR-UHFFFAOYSA-N 0.000 claims description 11
ABTXGUXSQCQMRR-UHFFFAOYSA-N 3-[5-methyl-4-[(4-phenylphenoxy)methyl]furan-2-yl]prop-2-enoic acid Chemical compound O1C(C=CC(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C ABTXGUXSQCQMRR-UHFFFAOYSA-N 0.000 claims description 10
XTILGJZDJAXWKZ-UHFFFAOYSA-N 3-[5-methyl-4-[(4-phenylphenoxy)methyl]furan-2-yl]propanoic acid Chemical compound O1C(CCC(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C XTILGJZDJAXWKZ-UHFFFAOYSA-N 0.000 claims description 10
FSFIRHNNEWIFSK-UHFFFAOYSA-N 4-[(4-phenylphenoxy)methyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 FSFIRHNNEWIFSK-UHFFFAOYSA-N 0.000 claims description 10
BCLCKUBMZHFDBT-UHFFFAOYSA-N 4-[[4-(2-methoxyphenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound COC1=CC=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(O)=O)=C1 BCLCKUBMZHFDBT-UHFFFAOYSA-N 0.000 claims description 10
VZELWYRDTOXTNN-UHFFFAOYSA-N 4-[[4-(4-methoxyphenyl)phenyl]carbamoyl]-5-methylfuran-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1NC(=O)C1=C(C)OC(C(O)=O)=C1 VZELWYRDTOXTNN-UHFFFAOYSA-N 0.000 claims description 10
MYWGMSWBVBETON-UHFFFAOYSA-N 4-[[4-[4-(difluoromethoxy)phenyl]phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=CC(OC(F)F)=CC=2)=C1C MYWGMSWBVBETON-UHFFFAOYSA-N 0.000 claims description 10
ONHNTLBCTOQTPL-UHFFFAOYSA-N 4-[[4-[4-(difluoromethoxy)phenyl]phenyl]sulfanylmethyl]-5-methyl-n-(2-methylphenyl)sulfonylfuran-2-carboxamide Chemical compound CC=1OC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=1CSC(C=C1)=CC=C1C1=CC=C(OC(F)F)C=C1 ONHNTLBCTOQTPL-UHFFFAOYSA-N 0.000 claims description 10
YMYMCMAUHIMLMI-UHFFFAOYSA-N 5-methyl-4-[(4-phenylanilino)methyl]furan-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(CNC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C YMYMCMAUHIMLMI-UHFFFAOYSA-N 0.000 claims description 10
LSFGCPPREOXRNU-UHFFFAOYSA-N 5-methyl-4-[(4-pyrimidin-2-ylphenoxy)methyl]furan-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2N=CC=CN=2)=C1C LSFGCPPREOXRNU-UHFFFAOYSA-N 0.000 claims description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
CRTKRSLMVFAIDS-UHFFFAOYSA-N n-(benzenesulfonyl)-3-[4-[[4-(4-methoxyphenyl)phenoxy]methyl]-5-methylfuran-2-yl]propanamide Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(CCC(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1 CRTKRSLMVFAIDS-UHFFFAOYSA-N 0.000 claims description 10
VQNRDXZKQLENCR-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[[4-(5-methoxypyridin-2-yl)phenoxy]methyl]-5-methylfuran-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1 VQNRDXZKQLENCR-UHFFFAOYSA-N 0.000 claims description 10
XCTUOFVEOWKSFZ-UHFFFAOYSA-N 3-[4-[[4-(4-methoxyphenyl)phenoxy]methyl]-5-methylfuran-2-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(CCC(O)=O)=C1 XCTUOFVEOWKSFZ-UHFFFAOYSA-N 0.000 claims description 9
NLZYTUVWUDMOHY-UHFFFAOYSA-N 4-[(4-phenylphenoxy)methyl]-5-propan-2-ylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C(C)C NLZYTUVWUDMOHY-UHFFFAOYSA-N 0.000 claims description 9
IYCFMYBIPRJSRP-UHFFFAOYSA-N 4-[[4-(1,3-benzodioxol-5-yl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=C3OCOC3=CC=2)=C1C IYCFMYBIPRJSRP-UHFFFAOYSA-N 0.000 claims description 9
RQFLBCGPZIEAJO-UHFFFAOYSA-N 4-[[4-(2,4-dimethoxyphenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(O)=O)=C1 RQFLBCGPZIEAJO-UHFFFAOYSA-N 0.000 claims description 9
GOCHWJSSFHCQHS-UHFFFAOYSA-N 4-[[4-(2,4-dimethoxyphenyl)phenoxy]methyl]-n-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]-5-methylfuran-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C2=C(ON=C2C)C)=C1 GOCHWJSSFHCQHS-UHFFFAOYSA-N 0.000 claims description 9
KGCMYWHVGMFMKH-UHFFFAOYSA-N 4-[[4-(4-acetylphenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound C1=CC(C(=O)C)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(O)=O)=C1 KGCMYWHVGMFMKH-UHFFFAOYSA-N 0.000 claims description 9
VUABMARFQLVILH-UHFFFAOYSA-N 4-[[4-(4-cyanophenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=CC(=CC=2)C#N)=C1C VUABMARFQLVILH-UHFFFAOYSA-N 0.000 claims description 9
DNNOVUYCIAFXLX-UHFFFAOYSA-N 4-[[4-(4-fluorophenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=CC(F)=CC=2)=C1C DNNOVUYCIAFXLX-UHFFFAOYSA-N 0.000 claims description 9
IXDVRRPNWPOPGV-UHFFFAOYSA-N 4-[[4-(5-methoxypyridin-2-yl)phenoxy]methyl]-5-methyl-n-(2-methylphenyl)sulfonylfuran-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=C1 IXDVRRPNWPOPGV-UHFFFAOYSA-N 0.000 claims description 9
AKDYETVPYDYEJE-UHFFFAOYSA-N 4-[[4-[4-(difluoromethoxy)phenyl]-n-methylanilino]methyl]-5-methylfuran-2-carboxylic acid Chemical compound C=1C=C(C=2C=CC(OC(F)F)=CC=2)C=CC=1N(C)CC=1C=C(C(O)=O)OC=1C AKDYETVPYDYEJE-UHFFFAOYSA-N 0.000 claims description 9
CHBRWBFWESIPKH-UHFFFAOYSA-N 5-methyl-4-[(4-phenylphenoxy)methyl]furan-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C CHBRWBFWESIPKH-UHFFFAOYSA-N 0.000 claims description 9
LAJVLLVBVGOGGD-UHFFFAOYSA-N 5-methyl-4-[2-(4-phenylphenoxy)ethyl]furan-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(CCOC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C LAJVLLVBVGOGGD-UHFFFAOYSA-N 0.000 claims description 9
USXGJSKJTPMMFQ-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[[4-(2-methoxyphenyl)phenoxy]methyl]-5-methylfuran-2-carboxamide Chemical compound COC1=CC=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1 USXGJSKJTPMMFQ-UHFFFAOYSA-N 0.000 claims description 9
MZQCUGJFZQRFIQ-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[[4-(4-methoxy-2-methylphenyl)phenoxy]methyl]-5-methylfuran-2-carboxamide Chemical compound CC1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1 MZQCUGJFZQRFIQ-UHFFFAOYSA-N 0.000 claims description 9
KQRPAOHVFDJWCE-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[[4-[4-(difluoromethoxy)phenyl]phenoxy]methyl]-5-methylfuran-2-carboxamide Chemical compound CC=1OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=1COC(C=C1)=CC=C1C1=CC=C(OC(F)F)C=C1 KQRPAOHVFDJWCE-UHFFFAOYSA-N 0.000 claims description 9
VLJJNADNXAIQND-UHFFFAOYSA-N n-(benzenesulfonyl)-5-methyl-4-[(4-phenylanilino)methyl]furan-2-carboxamide Chemical compound CC=1OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=1CNC(C=C1)=CC=C1C1=CC=CC=C1 VLJJNADNXAIQND-UHFFFAOYSA-N 0.000 claims description 9
MEPGWBZFXHBQKO-UHFFFAOYSA-N n-[4-[[4-(4-methoxyphenyl)phenoxy]methyl]-5-methylfuran-2-yl]sulfonyl-3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(S(=O)(=O)NC(=O)C2=C(ON=C2C)C)=C1 MEPGWBZFXHBQKO-UHFFFAOYSA-N 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
FXADEKCQQFLIQJ-UHFFFAOYSA-N 4-(dibenzofuran-3-yloxymethyl)-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1C FXADEKCQQFLIQJ-UHFFFAOYSA-N 0.000 claims description 8
YHSGPMXRAKQRKU-UHFFFAOYSA-N 4-[[4-[4-(difluoromethoxy)phenyl]phenyl]sulfonylmethyl]-5-methyl-n-(2-methylphenyl)sulfonylfuran-2-carboxamide Chemical compound CC=1OC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=1CS(=O)(=O)C(C=C1)=CC=C1C1=CC=C(OC(F)F)C=C1 YHSGPMXRAKQRKU-UHFFFAOYSA-N 0.000 claims description 8
NXWIJWSRSXTFMF-UHFFFAOYSA-N 5-[5-methyl-4-[(4-phenylphenoxy)methyl]furan-2-yl]-2h-tetrazole Chemical compound CC=1OC(C=2NN=NN=2)=CC=1COC(C=C1)=CC=C1C1=CC=CC=C1 NXWIJWSRSXTFMF-UHFFFAOYSA-N 0.000 claims description 8
208000019695 Migraine disease Diseases 0.000 claims description 8
SFXMLZOEQADXTC-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[[4-(2,4-dimethoxyphenyl)phenoxy]methyl]-5-methylfuran-2-carboxamide Chemical compound COC1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1 SFXMLZOEQADXTC-UHFFFAOYSA-N 0.000 claims description 8
CPIQUZVUMUJGMK-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[[4-[4-(difluoromethoxy)phenyl]anilino]methyl]-5-methylfuran-2-carboxamide Chemical compound CC=1OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=1CNC(C=C1)=CC=C1C1=CC=C(OC(F)F)C=C1 CPIQUZVUMUJGMK-UHFFFAOYSA-N 0.000 claims description 8
JKWWDKBIZDWTNI-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[[4-[4-(difluoromethoxy)phenyl]phenyl]sulfanylmethyl]-5-methylfuran-2-carboxamide Chemical compound CC=1OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=1CSC(C=C1)=CC=C1C1=CC=C(OC(F)F)C=C1 JKWWDKBIZDWTNI-UHFFFAOYSA-N 0.000 claims description 8
IWVUQIQXYATGRI-UHFFFAOYSA-N n-(benzenesulfonyl)-5-methyl-4-[(4-phenylphenoxy)methyl]furan-2-carboxamide Chemical compound CC=1OC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=1COC(C=C1)=CC=C1C1=CC=CC=C1 IWVUQIQXYATGRI-UHFFFAOYSA-N 0.000 claims description 8
SOKVOUSZWKKAAR-UHFFFAOYSA-N n-[(3,5-dimethyl-1,2-oxazol-4-yl)sulfonyl]-4-[[4-(5-methoxypyridin-2-yl)phenoxy]methyl]-5-methylfuran-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C2=C(ON=C2C)C)=C1 SOKVOUSZWKKAAR-UHFFFAOYSA-N 0.000 claims description 8
LRJOPXQHUOXWQW-UHFFFAOYSA-N n-[5-methyl-4-[(4-phenylphenoxy)methyl]furan-2-yl]sulfonylbenzamide Chemical compound CC=1OC(S(=O)(=O)NC(=O)C=2C=CC=CC=2)=CC=1COC(C=C1)=CC=C1C1=CC=CC=C1 LRJOPXQHUOXWQW-UHFFFAOYSA-N 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
SDICSXJDWBLHCI-UHFFFAOYSA-N 3-[4-[[4-(4-methoxyphenyl)phenoxy]methyl]-5-methylfuran-2-yl]prop-2-enoic acid Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C=CC(O)=O)=C1 SDICSXJDWBLHCI-UHFFFAOYSA-N 0.000 claims description 7
UNZLOYVZNRUPOG-UHFFFAOYSA-N 4-(2-dibenzofuran-3-yloxyethyl)-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(CCOC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1C UNZLOYVZNRUPOG-UHFFFAOYSA-N 0.000 claims description 7
WSTIRVWKSKMDEU-UHFFFAOYSA-N 4-(dibenzofuran-2-yloxymethyl)-5-(trifluoromethyl)furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(COC=2C=C3C4=CC=CC=C4OC3=CC=2)=C1C(F)(F)F WSTIRVWKSKMDEU-UHFFFAOYSA-N 0.000 claims description 7
YHPFYNGJQAIWIT-UHFFFAOYSA-N 4-(dibenzofuran-3-yloxymethyl)-5-(trifluoromethyl)furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(COC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1C(F)(F)F YHPFYNGJQAIWIT-UHFFFAOYSA-N 0.000 claims description 7
KOZKJWLTFYDLDN-UHFFFAOYSA-N 4-(dibenzofuran-3-yloxymethyl)-5-propan-2-ylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1C(C)C KOZKJWLTFYDLDN-UHFFFAOYSA-N 0.000 claims description 7
GPQXTYPIAATNTD-UHFFFAOYSA-N 4-(dibenzofuran-3-yloxymethyl)furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(COC=2C=C3C(C4=CC=CC=C4O3)=CC=2)=C1 GPQXTYPIAATNTD-UHFFFAOYSA-N 0.000 claims description 7
SAGWNXBYZYNMDZ-UHFFFAOYSA-N 4-[(4-phenylphenoxy)methyl]-5-(trifluoromethyl)furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C(F)(F)F SAGWNXBYZYNMDZ-UHFFFAOYSA-N 0.000 claims description 7
MZLPLOJRZCNDFZ-UHFFFAOYSA-N 4-[[4-(3-acetylphenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound CC(=O)C1=CC=CC(C=2C=CC(OCC3=C(OC(=C3)C(O)=O)C)=CC=2)=C1 MZLPLOJRZCNDFZ-UHFFFAOYSA-N 0.000 claims description 7
BMYOANQCCJLBKM-UHFFFAOYSA-N 4-[[4-(3-fluorophenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=C(F)C=CC=2)=C1C BMYOANQCCJLBKM-UHFFFAOYSA-N 0.000 claims description 7
WEGNZVCDZITRCA-UHFFFAOYSA-N 4-[[4-(3-hydroxyphenyl)phenoxy]methyl]-5-methylfuran-2-carboxylic acid Chemical compound O1C(C(O)=O)=CC(COC=2C=CC(=CC=2)C=2C=C(O)C=CC=2)=C1C WEGNZVCDZITRCA-UHFFFAOYSA-N 0.000 claims description 7
VYXQCSUVFBNYJQ-UHFFFAOYSA-N 4-[[4-(4-cyanophenyl)phenoxy]methyl]-5-(trifluoromethyl)furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(COC=2C=CC(=CC=2)C=2C=CC(=CC=2)C#N)=C1C(F)(F)F VYXQCSUVFBNYJQ-UHFFFAOYSA-N 0.000 claims description 7
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KGQKMYLTSFYZTJ-UHFFFAOYSA-N ethyl 2-[5-methyl-4-[tri(propan-2-yl)silyloxymethyl]furan-2-yl]acetate Chemical compound CCOC(=O)CC1=CC(CO[Si](C(C)C)(C(C)C)C(C)C)=C(C)O1 KGQKMYLTSFYZTJ-UHFFFAOYSA-N 0.000 description 5
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NSDZBJZUEQHRGN-UHFFFAOYSA-N 5-methyl-4-[(4-phenylphenoxy)methyl]furan-2-carbonitrile Chemical compound O1C(C#N)=CC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C NSDZBJZUEQHRGN-UHFFFAOYSA-N 0.000 description 4
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GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical group 0.000 description 4
150000001409 amidines Chemical class 0.000 description 4
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239000002585 base Substances 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
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IVNWAJAIVNETRU-UHFFFAOYSA-N ethyl 2-propan-2-ylfuran-3-carboxylate Chemical compound CCOC(=O)C=1C=COC=1C(C)C IVNWAJAIVNETRU-UHFFFAOYSA-N 0.000 description 4
MTYKLXQBRLMRJU-UHFFFAOYSA-N ethyl 3-[5-methyl-4-[tri(propan-2-yl)silyloxymethyl]furan-2-yl]propanoate Chemical compound CCOC(=O)CCC1=CC(CO[Si](C(C)C)(C(C)C)C(C)C)=C(C)O1 MTYKLXQBRLMRJU-UHFFFAOYSA-N 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
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150000002500 ions Chemical class 0.000 description 4
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LEAGJMFHDIHCEI-UHFFFAOYSA-N methyl 4-[(6-iodopyridin-3-yl)oxymethyl]-5-methylfuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(COC=2C=NC(I)=CC=2)=C1C LEAGJMFHDIHCEI-UHFFFAOYSA-N 0.000 description 4
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125000004433 nitrogen atom Chemical group N* 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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NO20053971A 2003-01-29 2005-08-25 EP4 reseptor antagonister, andvendelse derav og farmasoytisk sammensetning inneholdende en slik forbindelse NO332420B1 (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GBGB0302094.8A GB0302094D0 (en)	2003-01-29	2003-01-29	EP4 receptor antagonists
US44387203P	2003-01-31	2003-01-31
US50952103P	2003-10-09	2003-10-09
PCT/GB2004/000347 WO2004067524A1 (en)	2003-01-29	2004-01-29	Ep4 receptor antagonists

Publications (3)

Publication Number	Publication Date
NO20053971D0 NO20053971D0 (no)	2005-08-25
NO20053971L NO20053971L (no)	2005-10-31
NO332420B1 true NO332420B1 (no)	2012-09-17

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NO20053971A NO332420B1 (no)	2003-01-29	2005-08-25	EP4 reseptor antagonister, andvendelse derav og farmasoytisk sammensetning inneholdende en slik forbindelse

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EP (1)	EP1603893B1 (de)
JP (1)	JP5015586B2 (de)
KR (1)	KR101094003B1 (de)
CN (1)	CN100408570C (de)
AT (1)	ATE396182T1 (de)
AU (1)	AU2004207675B2 (de)
CA (1)	CA2514220C (de)
DE (1)	DE602004013938D1 (de)
DK (1)	DK1603893T3 (de)
ES (1)	ES2308139T3 (de)
NO (1)	NO332420B1 (de)
PT (1)	PT1603893E (de)
WO (1)	WO2004067524A1 (de)

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US7524870B2 (en) *	2004-12-03	2009-04-28	Hoffmann-La Roche Inc.	Biaryloxymethylarenecarboxylic acids as glycogen synthase activators
GB0507298D0 (en)	2005-04-11	2005-05-18	Novartis Ag	Organic compounds
UY30121A1 (es)	2006-02-03	2007-08-31	Glaxo Group Ltd	Nuevos compuestos
AU2007331471C1 (en)	2006-12-15	2013-07-25	Glaxo Group Limited	Benzamide derivatives as EP4 receptor agonists
GB0721611D0 (en)	2007-11-02	2007-12-12	Glaxo Group Ltd	Novel compounds
CN101367783A (zh)	2008-10-10	2009-02-18	中国科学技术大学	5-羟甲基糠醛的制备方法
WO2011003300A1 (zh)	2009-07-09	2011-01-13	中国科学技术大学	羟甲基糠醛的制备方法
EP2392323A4 (de)	2009-01-30	2012-09-26	Univ Kyoto	Progressionshemmer für prostatakrebs und verfahren zur progressionshemmung
US9457084B2 (en) *	2010-02-22	2016-10-04	Raqualia Pharma Inc.	Use of EP4 receptor antagonists in the treatment of IL-23 mediated diseases
JP5996532B2 (ja)	2010-07-15	2016-09-21	バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒＩｎｔｅｌｌｅｃｔｕａｌＰｒｏｐｅｒｔｙＧｍｂＨ	有害生物防除剤としての新規複素環式化合物
CN102718734A (zh) *	2012-05-31	2012-10-10	中国科学技术大学	一种4-羟甲基糠酸和2,4-呋喃二甲酸的制备方法
UA115576C2 (uk)	2012-12-06	2017-11-27	Байєр Фарма Акцієнгезелльшафт	Похідні бензимідазолу як антагоністи ер4
US10391086B2 (en)	2013-03-19	2019-08-27	Askat Inc.	Use of EP4 receptor antagonists in the treatment of cartilage disease
CA2907049C (en)	2013-03-19	2021-08-10	Askat Inc.	Use of ep4 receptor antagonists in the treatment of cartilage disease
TW201607943A (zh)	2013-12-19	2016-03-01	拜耳製藥公司	作為ｅｐ４配體之新穎苯并咪唑衍生物
CR20180323A (es)	2015-11-20	2018-08-06	Idorsia Pharmaceuticals Ltd	Derivados de indol n-sustituídos como moduladores de los receptores de pge2
WO2018162562A1 (en)	2017-03-10	2018-09-13	Bayer Pharma Aktiengesellschaft	Use of an ep4 antagonist for the treatment of inflammatory pain
US11839613B2 (en)	2017-05-18	2023-12-12	Idorsia Pharmaceuticals Ltd	Pyrimidine derivatives as PGE2 receptor modulators
TWI768043B (zh)	2017-05-18	2022-06-21	瑞士商愛杜西亞製藥有限公司	N-取代吲哚衍生物
PE20191814A1 (es)	2017-05-18	2019-12-27	Idorsia Pharmaceuticals Ltd	Derivados de pirimidina como moduladores del receptor de pge2
TW201900179A (zh)	2017-05-18	2019-01-01	瑞士商愛杜西亞製藥有限公司	作為pge2受體調節劑之苯并呋喃及苯并噻吩衍生物
KR102612140B1 (ko)	2017-05-18	2023-12-08	이도르시아 파마슈티컬스 리미티드	피리미딘 유도체
WO2019038156A1 (en)	2017-08-22	2019-02-28	Bayer Pharma Aktiengesellschaft	USE OF AN EP4 ANTAGONIST FOR THE TREATMENT OF ARTHRITIS
US20230390303A1 (en)	2020-11-13	2023-12-07	Ono Pharmaceutical Co., Ltd.	Cancer treatment by combination of ep4 antagonist and immune checkpoint inhibitor

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PT1369419E (pt) *	2001-03-12	2007-08-16	Ono Pharmaceutical Co	Composto de n-fenilarilsulfonamida, fármaco contendo o composto como ingrediente activo, produtos intermédios para a produção do composto e processos para a produção do composto
US6825198B2 (en) *	2001-06-21	2004-11-30	Pfizer Inc	5-HT receptor ligands and uses thereof

2004
- 2004-01-29 DE DE602004013938T patent/DE602004013938D1/de not_active Expired - Lifetime
- 2004-01-29 ES ES04706221T patent/ES2308139T3/es not_active Expired - Lifetime
- 2004-01-29 PT PT04706221T patent/PT1603893E/pt unknown
- 2004-01-29 DK DK04706221T patent/DK1603893T3/da active
- 2004-01-29 AU AU2004207675A patent/AU2004207675B2/en not_active Ceased
- 2004-01-29 AT AT04706221T patent/ATE396182T1/de active
- 2004-01-29 KR KR1020057014131A patent/KR101094003B1/ko not_active Expired - Fee Related
- 2004-01-29 CA CA2514220A patent/CA2514220C/en not_active Expired - Fee Related
- 2004-01-29 EP EP04706221A patent/EP1603893B1/de not_active Expired - Lifetime
- 2004-01-29 WO PCT/GB2004/000347 patent/WO2004067524A1/en not_active Ceased
- 2004-01-29 CN CNB200480007457XA patent/CN100408570C/zh not_active Expired - Fee Related
- 2004-01-29 JP JP2006502209A patent/JP5015586B2/ja not_active Expired - Fee Related
2005
- 2005-08-25 NO NO20053971A patent/NO332420B1/no not_active IP Right Cessation

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CA2514220C (en)	2012-02-28
CN100408570C (zh)	2008-08-06
NO20053971L (no)	2005-10-31
DK1603893T3 (da)	2008-09-08
AU2004207675B2 (en)	2010-05-20
EP1603893B1 (de)	2008-05-21
ES2308139T3 (es)	2008-12-01
PT1603893E (pt)	2008-08-21
KR101094003B1 (ko)	2011-12-15
CA2514220A1 (en)	2004-08-12
JP5015586B2 (ja)	2012-08-29
AU2004207675A1 (en)	2004-08-12
WO2004067524A1 (en)	2004-08-12
CN1761657A (zh)	2006-04-19
DE602004013938D1 (de)	2008-07-03
ATE396182T1 (de)	2008-06-15
NO20053971D0 (no)	2005-08-25
EP1603893A1 (de)	2005-12-14
JP2006516600A (ja)	2006-07-06
KR20050097966A (ko)	2005-10-10

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2013-03-04	CHAD	Change of the owner's name or address (par. 44 patent law, par. patentforskriften)	Owner name: ASTERAND UK ACQUISITION LTD, GB
2013-08-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO332420B1 (no)	2012-09-17	EP4 reseptor antagonister, andvendelse derav og farmasoytisk sammensetning inneholdende en slik forbindelse
JP5583694B2 (ja)	2014-09-03	Ｃｂ２受容体を調節するピロリジン化合物
ES2376668T3 (es)	2012-03-15	Derivado de imidazol.
JP5756800B2 (ja)	2015-07-29	Ｃｂ２受容体を調節するアゼチジン２−カルボキサミド誘導体
JP5749162B2 (ja)	2015-07-15	Ｃｂ２受容体を調節するスルホン化合物
CA2731196A1 (en)	2010-01-21	Benzazepine derivatives and their use as hstamine h3 antagonists
JP2011520884A (ja)	2011-07-21	Ｃｂ２受容体を変調するスルホン化合物
CN102164917A (zh)	2011-08-24	选择性调节cb2受体的磺酰基化合物
JP2011503080A (ja)	2011-01-27	Ｃｂ２受容体を調節する化合物
AU2004281225B2 (en)	2010-11-18	Furan derivatives as EP4 receptor antagonists
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