NO332434B1 - Iminoazolinonvinylkondensert benzenderivat, fremstilling og anvendelse derav, samt sammensetning omfattende nevnte forbindelse - Google Patents

Info

Publication number

NO332434B1

NO332434B1 NO20060573A NO20060573A NO332434B1 NO 332434 B1 NO332434 B1 NO 332434B1 NO 20060573 A NO20060573 A NO 20060573A NO 20060573 A NO20060573 A NO 20060573A NO 332434 B1 NO332434 B1 NO 332434B1

Authority

NO

Norway

Prior art keywords

dioxol

benzo

ylmethylene

oxothiazolidin

ylidene

Prior art date

2003-07-28

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• 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 41
• 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 30
• 150000001875 compounds Chemical class 0.000 title claims description 81
• 238000002360 preparation method Methods 0.000 title claims description 40
• 239000000203 mixture Substances 0.000 title description 23
• 238000011282 treatment Methods 0.000 claims abstract description 14
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• 230000004770 neurodegeneration Effects 0.000 claims abstract description 9
• 238000002054 transplantation Methods 0.000 claims abstract description 9
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 8
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• 208000017169 kidney disease Diseases 0.000 claims abstract description 7
• 210000004072 lung Anatomy 0.000 claims abstract description 4
• -1 pyrazolesulfonyl Chemical group 0.000 claims description 74
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 230000004913 activation Effects 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 201000010099 disease Diseases 0.000 claims description 10
• 210000000056 organ Anatomy 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 210000000265 leukocyte Anatomy 0.000 claims description 8
• JEKRDQAYXNWAID-UHFFFAOYSA-N methyl 3-[[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]sulfamoyl]thiophene-2-carboxylate Chemical compound S1C=CC(S(=O)(=O)N=C2SC(C(=O)N2)=CC=2C=C3OCOC3=CC=2)=C1C(=O)OC JEKRDQAYXNWAID-UHFFFAOYSA-N 0.000 claims description 8
• XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 7
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• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• MMBHBLSMTJBNKF-UHFFFAOYSA-N 2-(propylamino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=NCCC)NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 MMBHBLSMTJBNKF-UHFFFAOYSA-N 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
• AIMKWBLBSPOZKY-UHFFFAOYSA-N 2-(benzylamino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3C=CC=NC3=CC=2)C(=O)NC1=NCC1=CC=CC=C1 AIMKWBLBSPOZKY-UHFFFAOYSA-N 0.000 claims description 5
• UWQFOXZSBUBKSV-UHFFFAOYSA-N 2-chloro-n-[4-oxo-5-(quinolin-6-ylmethylidene)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound ClC1=CC=CC=C1S(=O)(=O)N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 UWQFOXZSBUBKSV-UHFFFAOYSA-N 0.000 claims description 5
• XLTOVGVXNCHRFM-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-ylmethylidene)-2-(benzylamino)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3OCOC3=CC=2)C(=O)NC1=NCC1=CC=CC=C1 XLTOVGVXNCHRFM-UHFFFAOYSA-N 0.000 claims description 5
• HKXWBEAUCOSJCH-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-ylmethylidene)-2-(methoxyamino)-1,3-thiazol-4-one Chemical compound S1C(=NOC)NC(=O)C1=CC1=CC=C(OCO2)C2=C1 HKXWBEAUCOSJCH-UHFFFAOYSA-N 0.000 claims description 5
• DUBLVXRZFIWEFC-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-ylmethylidene)-2-(propylamino)-1,3-thiazol-4-one Chemical compound S1C(=NCCC)NC(=O)C1=CC1=CC=C(OCO2)C2=C1 DUBLVXRZFIWEFC-UHFFFAOYSA-N 0.000 claims description 5
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• QCTBGFQBMMDJLF-UHFFFAOYSA-N n-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]-2-phenylbenzenesulfonamide Chemical compound S1C(=CC=2C=C3OCOC3=CC=2)C(=O)NC1=NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 QCTBGFQBMMDJLF-UHFFFAOYSA-N 0.000 claims description 5
• VXBFQAVZFIDHJK-UHFFFAOYSA-N n-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]-3-chlorobenzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)N=C2SC(C(=O)N2)=CC=2C=C3OCOC3=CC=2)=C1 VXBFQAVZFIDHJK-UHFFFAOYSA-N 0.000 claims description 5
• YYCNZCPCSMORHD-UHFFFAOYSA-N n-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]-5-chloro-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)N=C(NC1=O)SC1=CC1=CC=C(OCO2)C2=C1 YYCNZCPCSMORHD-UHFFFAOYSA-N 0.000 claims description 5
• DHCASRIDNXOVFX-UHFFFAOYSA-N n-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]-6-chloropyridine-3-sulfonamide Chemical compound C1=NC(Cl)=CC=C1S(=O)(=O)N=C(NC1=O)SC1=CC1=CC=C(OCO2)C2=C1 DHCASRIDNXOVFX-UHFFFAOYSA-N 0.000 claims description 5
• KYQHPPNKNYJKFN-UHFFFAOYSA-N n-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]pyridine-3-sulfonamide Chemical compound S1C(=CC=2C=C3OCOC3=CC=2)C(=O)NC1=NS(=O)(=O)C1=CC=CN=C1 KYQHPPNKNYJKFN-UHFFFAOYSA-N 0.000 claims description 5
• LEZJMPUADMKMRT-UHFFFAOYSA-N 3-[[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]sulfamoyl]thiophene-2-carboxylic acid Chemical compound S1C=CC(S(=O)(=O)N=C2SC(C(=O)N2)=CC=2C=C3OCOC3=CC=2)=C1C(=O)O LEZJMPUADMKMRT-UHFFFAOYSA-N 0.000 claims description 4
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• HLCPRFODELCNCT-UHFFFAOYSA-N n-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]ethanesulfonamide Chemical compound S1C(=NS(=O)(=O)CC)NC(=O)C1=CC1=CC=C(OCO2)C2=C1 HLCPRFODELCNCT-UHFFFAOYSA-N 0.000 claims description 4
• IXKLRTMVDYDFKY-UHFFFAOYSA-N n-[5-(1,3-benzodioxol-5-ylmethylidene)-4-oxo-1,3-thiazol-2-yl]quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)N=C3NC(C(S3)=CC=3C=C4OCOC4=CC=3)=O)=CC=CC2=C1 IXKLRTMVDYDFKY-UHFFFAOYSA-N 0.000 claims description 4
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