NO318623B1 - Prostaglandin-endoperoksid-H-syntase-biosynteseinhibitorer - Google Patents

Info

Publication number

NO318623B1

NO318623B1 NO20012061A NO20012061A NO318623B1 NO 318623 B1 NO318623 B1 NO 318623B1 NO 20012061 A NO20012061 A NO 20012061A NO 20012061 A NO20012061 A NO 20012061A NO 318623 B1 NO318623 B1 NO 318623B1

Authority

NO

Norway

Prior art keywords

hydroxy

phenyl

methyl

pyridazinone

methylsulfonyl

Prior art date

1998-10-27

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• 150000003180 prostaglandins Chemical class 0.000 title claims description 30
• 150000001875 compounds Chemical class 0.000 claims abstract description 206
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims abstract description 12
• 206010061218 Inflammation Diseases 0.000 claims abstract description 9
• 230000004054 inflammatory process Effects 0.000 claims abstract description 9
• -1 2-hydroxy-2-methyl-propyloxy Chemical group 0.000 claims description 77
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 67
• 230000015572 biosynthetic process Effects 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• QPTNEZSIWLUDPF-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(2-hydroxy-2-methylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 QPTNEZSIWLUDPF-UHFFFAOYSA-N 0.000 claims description 18
• 159000000000 sodium salts Chemical class 0.000 claims description 18
• 239000000651 prodrug Substances 0.000 claims description 17
• 229940002612 prodrug Drugs 0.000 claims description 17
• 150000002148 esters Chemical class 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• XNTLXAUHLBBEKP-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 XNTLXAUHLBBEKP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• GAJBVUJFSOJZDQ-UHFFFAOYSA-N n-[4-[1-(3,4-difluorophenyl)-5-(2-hydroxy-2-methylpropoxy)-6-oxopyridazin-4-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(OCC(C)(C)O)C(=O)N(C=2C=C(F)C(F)=CC=2)N=C1 GAJBVUJFSOJZDQ-UHFFFAOYSA-N 0.000 claims description 7
• KTEVYFCRLSIJNM-UHFFFAOYSA-N n-[4-[1-(3-chloro-4-fluorophenyl)-5-(2-hydroxy-2-methylpropoxy)-6-oxopyridazin-4-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(OCC(C)(C)O)C(=O)N(C=2C=C(Cl)C(F)=CC=2)N=C1 KTEVYFCRLSIJNM-UHFFFAOYSA-N 0.000 claims description 7
• WZRCQBJHCFBYLB-UHFFFAOYSA-N n-[4-[1-(3-chlorophenyl)-5-(2-hydroxy-2-methylpropoxy)-6-oxopyridazin-4-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(OCC(C)(C)O)C(=O)N(C=2C=C(Cl)C=CC=2)N=C1 WZRCQBJHCFBYLB-UHFFFAOYSA-N 0.000 claims description 7
• YGZJJTHSQQJERI-UHFFFAOYSA-N n-[4-[1-(4-fluorophenyl)-5-(3-hydroxy-3-methylbutoxy)-6-oxopyridazin-4-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(OCCC(C)(C)O)C(=O)N(C=2C=CC(F)=CC=2)N=C1 YGZJJTHSQQJERI-UHFFFAOYSA-N 0.000 claims description 7
• GASRXVWUCPPQCN-UHFFFAOYSA-N n-[4-[5-(2-hydroxy-2-methylpropoxy)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(OCC(C)(C)O)C(=O)N(CC(F)(F)F)N=C1 GASRXVWUCPPQCN-UHFFFAOYSA-N 0.000 claims description 7
• GWFWRSOKMBUJAV-UHFFFAOYSA-N n-[4-[5-(3-hydroxy-2,2-dimethylpropoxy)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(OCC(C)(C)CO)C(=O)N(CC(F)(F)F)N=C1 GWFWRSOKMBUJAV-UHFFFAOYSA-N 0.000 claims description 7
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
• FCVOIISBMQGTOB-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 FCVOIISBMQGTOB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• YELGVOXMDKPKTD-UHFFFAOYSA-N 4-[1-(3,4-difluorophenyl)-5-(2-hydroxy-2-methylpropoxy)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 YELGVOXMDKPKTD-UHFFFAOYSA-N 0.000 claims description 4
• RTBZTMBBTZKEEF-UHFFFAOYSA-N 4-[1-(3-chloro-4-fluorophenyl)-5-(2-hydroxy-2-methylpropoxy)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 RTBZTMBBTZKEEF-UHFFFAOYSA-N 0.000 claims description 4
• VJCMXNBWIGYWIX-UHFFFAOYSA-N 4-[1-(3-chlorophenyl)-5-(2-hydroxy-2-methylpropoxy)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 VJCMXNBWIGYWIX-UHFFFAOYSA-N 0.000 claims description 4
• KDYMPGNVZWLCSS-UHFFFAOYSA-N 4-[1-(4-fluorophenyl)-5-(3-hydroxy-3-methylbutoxy)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=C(F)C=C1 KDYMPGNVZWLCSS-UHFFFAOYSA-N 0.000 claims description 4
• CHEGDWJQDOBZAA-UHFFFAOYSA-N 4-[5-(2-hydroxy-2-methylpropoxy)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OCC(C)(O)C)=C1C1=CC=C(S(N)(=O)=O)C=C1 CHEGDWJQDOBZAA-UHFFFAOYSA-N 0.000 claims description 4
• DZKMJRYEUVLBJB-UHFFFAOYSA-N 4-[5-(3-hydroxy-2,2-dimethylpropoxy)-6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-4-yl]benzenesulfonamide Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OCC(C)(CO)C)=C1C1=CC=C(S(N)(=O)=O)C=C1 DZKMJRYEUVLBJB-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• 208000002193 Pain Diseases 0.000 claims description 4
• 206010037660 Pyrexia Diseases 0.000 claims description 4
• 239000002168 alkylating agent Substances 0.000 claims description 4
• 229940100198 alkylating agent Drugs 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• DIRNSUWKRHPEFO-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-hydroxy-2,2-dimethylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 DIRNSUWKRHPEFO-UHFFFAOYSA-N 0.000 claims description 3
• GEJQAJWDKJZYTC-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(4-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 GEJQAJWDKJZYTC-UHFFFAOYSA-N 0.000 claims description 3
• QRQYHOCFOAOHBK-HXUWFJFHSA-N 2-(3,4-difluorophenyl)-4-[(2s)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 QRQYHOCFOAOHBK-HXUWFJFHSA-N 0.000 claims description 3
• KDJWTTCLGKFONX-ZDUSSCGKSA-N 2-(3,4-difluorophenyl)-4-[(2s)-3-hydroxy-2-methylpropoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@H](CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 KDJWTTCLGKFONX-ZDUSSCGKSA-N 0.000 claims description 3
• COULPBUETDYWQE-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(2-hydroxy-2-methylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 COULPBUETDYWQE-UHFFFAOYSA-N 0.000 claims description 3
• YMUYUABGNBZLOM-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(3-hydroxy-2,2-dimethylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 YMUYUABGNBZLOM-UHFFFAOYSA-N 0.000 claims description 3
• OQBDNDYDMWPBPJ-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 OQBDNDYDMWPBPJ-UHFFFAOYSA-N 0.000 claims description 3
• UORNLBNMIVTEFR-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(3-hydroxy-2,2-dimethylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 UORNLBNMIVTEFR-UHFFFAOYSA-N 0.000 claims description 3
• NURAWQHKVMNZEZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(3-hydroxy-2,2-dimethylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 NURAWQHKVMNZEZ-UHFFFAOYSA-N 0.000 claims description 3
• PORJADFRTDGOOL-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C=C1 PORJADFRTDGOOL-UHFFFAOYSA-N 0.000 claims description 3
• YAYLFJDUWAVLET-UHFFFAOYSA-N 4-(3-hydroxy-2,2-dimethylpropoxy)-5-(4-methylsulfonylphenyl)-2-(2,2,2-trifluoroethyl)pyridazin-3-one Chemical compound C1=NN(CC(F)(F)F)C(=O)C(OCC(C)(CO)C)=C1C1=CC=C(S(C)(=O)=O)C=C1 YAYLFJDUWAVLET-UHFFFAOYSA-N 0.000 claims description 3
• CDUVGFOEOPBRPY-UHFFFAOYSA-N 4-[1-(3,4-difluorophenyl)-5-(3-hydroxy-3-methylbutoxy)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 CDUVGFOEOPBRPY-UHFFFAOYSA-N 0.000 claims description 3
• YVOPYQGKIKLXNH-UHFFFAOYSA-N 4-[1-(3-chloro-4-fluorophenyl)-5-(3-hydroxy-3-methylbutoxy)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 YVOPYQGKIKLXNH-UHFFFAOYSA-N 0.000 claims description 3
• QPVOENXMJUXILD-UHFFFAOYSA-N 4-[1-(3-chlorophenyl)-5-(3-hydroxy-3-methylbutoxy)-6-oxopyridazin-4-yl]benzenesulfonamide Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(N)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 QPVOENXMJUXILD-UHFFFAOYSA-N 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 230000000269 nucleophilic effect Effects 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• LYVAPTCVRNVGCG-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-4-(2-hydroxy-2-methylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(Cl)C(Cl)=C1 LYVAPTCVRNVGCG-UHFFFAOYSA-N 0.000 claims description 2
• KNJRLSSPFGSWMD-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(Cl)C(Cl)=C1 KNJRLSSPFGSWMD-UHFFFAOYSA-N 0.000 claims description 2
• HZRPOYBVCKGWTB-FQEVSTJZSA-N 2-(3,4-dichlorophenyl)-4-[(2r)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(Cl)C(Cl)=C1 HZRPOYBVCKGWTB-FQEVSTJZSA-N 0.000 claims description 2
• HZRPOYBVCKGWTB-HXUWFJFHSA-N 2-(3,4-dichlorophenyl)-4-[(2s)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(Cl)C(Cl)=C1 HZRPOYBVCKGWTB-HXUWFJFHSA-N 0.000 claims description 2
• QRQYHOCFOAOHBK-FQEVSTJZSA-N 2-(3,4-difluorophenyl)-4-[(2r)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 QRQYHOCFOAOHBK-FQEVSTJZSA-N 0.000 claims description 2
• KDJWTTCLGKFONX-CYBMUJFWSA-N 2-(3,4-difluorophenyl)-4-[(2r)-3-hydroxy-2-methylpropoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@@H](CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 KDJWTTCLGKFONX-CYBMUJFWSA-N 0.000 claims description 2
• NHGUNUSJGXLYSW-FQEVSTJZSA-N 2-(3-bromo-4-fluorophenyl)-4-[(2r)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Br)=C1 NHGUNUSJGXLYSW-FQEVSTJZSA-N 0.000 claims description 2
• NHGUNUSJGXLYSW-HXUWFJFHSA-N 2-(3-bromo-4-fluorophenyl)-4-[(2s)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Br)=C1 NHGUNUSJGXLYSW-HXUWFJFHSA-N 0.000 claims description 2
• ULTNUHJTUQZSQK-FQEVSTJZSA-N 2-(3-bromophenyl)-4-[(2r)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Br)=C1 ULTNUHJTUQZSQK-FQEVSTJZSA-N 0.000 claims description 2
• ULTNUHJTUQZSQK-HXUWFJFHSA-N 2-(3-bromophenyl)-4-[(2s)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Br)=C1 ULTNUHJTUQZSQK-HXUWFJFHSA-N 0.000 claims description 2
• DINDDYJFKBPWMN-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-4-(4-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 DINDDYJFKBPWMN-UHFFFAOYSA-N 0.000 claims description 2
• CUGVVHOBDSRYOF-FQEVSTJZSA-N 2-(3-chloro-4-fluorophenyl)-4-[(2r)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 CUGVVHOBDSRYOF-FQEVSTJZSA-N 0.000 claims description 2
• BCXSVWURMHPDHK-CYBMUJFWSA-N 2-(3-chloro-4-fluorophenyl)-4-[(2r)-3-hydroxy-2-methylpropoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@@H](CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 BCXSVWURMHPDHK-CYBMUJFWSA-N 0.000 claims description 2
• CUGVVHOBDSRYOF-HXUWFJFHSA-N 2-(3-chloro-4-fluorophenyl)-4-[(2s)-2-hydroxy-3-methylbutoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@@H](O)C(C)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 CUGVVHOBDSRYOF-HXUWFJFHSA-N 0.000 claims description 2
• BCXSVWURMHPDHK-ZDUSSCGKSA-N 2-(3-chloro-4-fluorophenyl)-4-[(2s)-3-hydroxy-2-methylpropoxy]-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OC[C@H](CO)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(Cl)=C1 BCXSVWURMHPDHK-ZDUSSCGKSA-N 0.000 claims description 2
• GOJYFBBKSWPGBJ-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(2-hydroxy-2-methylpropoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=CC(Cl)=C1 GOJYFBBKSWPGBJ-UHFFFAOYSA-N 0.000 claims description 2
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