NO327425B1 - Vannopploselige fenylpyridazinderivater medisiner inneholdende disse, samt anvendelse av disse for fremstilling av medikamenter for behandling av sykdom - Google Patents

Vannopploselige fenylpyridazinderivater medisiner inneholdende disse, samt anvendelse av disse for fremstilling av medikamenter for behandling av sykdom Download PDF

Info

Publication number: NO327425B1
Authority: NO; Norway
Prior art keywords: pyridazin; fluoro; methyl; isobutyl; methoxyphenyl
Prior art date: 2001-09-26

Application number

NO20041250A

Other languages

English (en)

Norwegian (no)

Other versions

NO20041250L (no

Inventor

Hiromichi Shigyo

Seiichi Sato

Yoshinori Kyotani

Tomoyuki Koshi

Takahiro Kitamura

Hideo Yoshizaki

Kyoko Yasuoka

Shunji Takemura

Junko Totsuka

Original Assignee

Kowa Co

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.)

2001-09-26

Filing date

2004-03-25

Publication date

2009-06-29

2004-03-25 Application filed by Kowa Co filed Critical Kowa Co

2004-03-25 Publication of NO20041250L publication Critical patent/NO20041250L/no

2009-06-29 Publication of NO327425B1 publication Critical patent/NO327425B1/no

Links

239000003814 drug Substances 0.000 title claims description 25
238000004519 manufacturing process Methods 0.000 title claims description 24
201000010099 disease Diseases 0.000 title claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 8
229940079593 drug Drugs 0.000 title claims description 7
XWSSUYOEOWLFEI-UHFFFAOYSA-N 3-phenylpyridazine Chemical class C1=CC=CC=C1C1=CC=CN=N1 XWSSUYOEOWLFEI-UHFFFAOYSA-N 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 423
238000002360 preparation method Methods 0.000 claims description 379
-1 halocinnamyl Chemical group 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
239000000825 pharmaceutical preparation Substances 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
229940124597 therapeutic agent Drugs 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
208000023589 ischemic disease Diseases 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
230000003449 preventive effect Effects 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
208000026278 immune system disease Diseases 0.000 claims description 6
208000027866 inflammatory disease Diseases 0.000 claims description 6
230000002757 inflammatory effect Effects 0.000 claims description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
208000001132 Osteoporosis Diseases 0.000 claims description 5
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 5
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 4
HJIWEYIBBQNBFX-UHFFFAOYSA-N 2-(cyclopentylmethyl)-6-(3-fluoro-4-methoxyphenyl)-4-[(4-methylpiperazin-1-yl)methyl]pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CCCC2)C(=O)C(CN2CCN(C)CC2)=C1 HJIWEYIBBQNBFX-UHFFFAOYSA-N 0.000 claims description 4
VBWWARWXUAUFMR-UHFFFAOYSA-N 2-(cyclopropylmethyl)-4-[(4-methylpiperazin-1-yl)methyl]-6-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=NN(CC2CC2)C(=O)C(CN2CCN(C)CC2)=C1 VBWWARWXUAUFMR-UHFFFAOYSA-N 0.000 claims description 4
JADJVJRMAGEXNX-UHFFFAOYSA-N 2-(cyclopropylmethyl)-6-(3-fluoro-4-methoxyphenyl)-4-(3-piperazin-1-ylpropyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CC2)C(=O)C(CCCN2CCNCC2)=C1 JADJVJRMAGEXNX-UHFFFAOYSA-N 0.000 claims description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
YBQKTAMBYSYZAX-UHFFFAOYSA-N 4-(aminomethyl)-2-[(4-chlorophenyl)methyl]-6-(3-fluoro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC=2C=CC(Cl)=CC=2)C(=O)C(CN)=C1 YBQKTAMBYSYZAX-UHFFFAOYSA-N 0.000 claims description 4
DFZGCZVYWUFZSV-UHFFFAOYSA-N 6-(3-fluoro-4-methoxyphenyl)-2-[(4-fluorophenyl)methyl]-4-(piperazin-1-ylmethyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC=2C=CC(F)=CC=2)C(=O)C(CN2CCNCC2)=C1 DFZGCZVYWUFZSV-UHFFFAOYSA-N 0.000 claims description 4
QQJJWXCZSWJHHN-UHFFFAOYSA-N 6-(4-fluoro-3-methylphenyl)-4-[(4-methylpiperazin-1-yl)methyl]-2-(2-methylpropyl)pyridazin-3-one Chemical compound O=C1N(CC(C)C)N=C(C=2C=C(C)C(F)=CC=2)C=C1CN1CCN(C)CC1 QQJJWXCZSWJHHN-UHFFFAOYSA-N 0.000 claims description 4
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125000001072 heteroaryl group Chemical group 0.000 claims description 4
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230000000638 stimulation Effects 0.000 claims description 4
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
DFCJKEFPAQGMCA-UHFFFAOYSA-N 2-(2-methylpropyl)-6-(4-methylsulfanylphenyl)-4-[(prop-2-ynylamino)methyl]pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=NN(CC(C)C)C(=O)C(CNCC#C)=C1 DFCJKEFPAQGMCA-UHFFFAOYSA-N 0.000 claims description 3
BMRYHNWKEVKQBE-UHFFFAOYSA-N 2-(cyclopropylmethyl)-4-[(dimethylamino)methyl]-6-(3-fluoro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CC2)C(=O)C(CN(C)C)=C1 BMRYHNWKEVKQBE-UHFFFAOYSA-N 0.000 claims description 3
LKYKTBNADASYCG-UHFFFAOYSA-N 2-(cyclopropylmethyl)-6-(3-fluoro-4-methoxyphenyl)-4-(piperazin-1-ylmethyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CC2)C(=O)C(CN2CCNCC2)=C1 LKYKTBNADASYCG-UHFFFAOYSA-N 0.000 claims description 3
IOMVBHXILIULFR-UHFFFAOYSA-N 2-[(3,4-difluorophenyl)methyl]-6-(3-fluoro-4-methoxyphenyl)-4-[(4-methylpiperazin-1-yl)methyl]pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC=2C=C(F)C(F)=CC=2)C(=O)C(CN2CCN(C)CC2)=C1 IOMVBHXILIULFR-UHFFFAOYSA-N 0.000 claims description 3
NNEQUEWHDAVFDK-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-4-[(dimethylamino)methyl]-6-(3-fluoro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC=2C=CC(Cl)=CC=2)C(=O)C(CN(C)C)=C1 NNEQUEWHDAVFDK-UHFFFAOYSA-N 0.000 claims description 3
WWCVLHYZFUEAFT-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)prop-2-enyl]-6-(3-fluoro-4-methoxyphenyl)-4-[(4-methylpiperazin-1-yl)methyl]pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC=CC=2C=CC(Cl)=CC=2)C(=O)C(CN2CCN(C)CC2)=C1 WWCVLHYZFUEAFT-UHFFFAOYSA-N 0.000 claims description 3
DHPFWWUKJNRDNZ-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)prop-2-enyl]-6-(4-fluoro-3-methylphenyl)-4-[(4-methylpiperazin-1-yl)methyl]pyridazin-3-one Chemical compound C1CN(C)CCN1CC(C1=O)=CC(C=2C=C(C)C(F)=CC=2)=NN1CC=CC1=CC=C(Cl)C=C1 DHPFWWUKJNRDNZ-UHFFFAOYSA-N 0.000 claims description 3
FXJLDAAIVGSIHA-UHFFFAOYSA-N 4-(3-aminopropyl)-2-(cyclopropylmethyl)-6-(3-fluoro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CC2)C(=O)C(CCCN)=C1 FXJLDAAIVGSIHA-UHFFFAOYSA-N 0.000 claims description 3
KQBSCLSOGLWZES-UHFFFAOYSA-N 4-(aminomethyl)-2-(cyclopentylmethyl)-6-(3-fluoro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CCCC2)C(=O)C(CN)=C1 KQBSCLSOGLWZES-UHFFFAOYSA-N 0.000 claims description 3
RSUNCOOVWVTXTF-UHFFFAOYSA-N 4-(aminomethyl)-2-(cyclopropylmethyl)-6-(3-fluoro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CC2)C(=O)C(CN)=C1 RSUNCOOVWVTXTF-UHFFFAOYSA-N 0.000 claims description 3
OIZHFKZXZJUOEH-UHFFFAOYSA-N 4-(aminomethyl)-6-(3-fluoro-4-methoxyphenyl)-2-[(4-fluorophenyl)methyl]pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC=2C=CC(F)=CC=2)C(=O)C(CN)=C1 OIZHFKZXZJUOEH-UHFFFAOYSA-N 0.000 claims description 3
ZQTJWQQGVDLPHB-UHFFFAOYSA-N 4-(aminomethyl)-6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CCCC=2C=CC(F)=CC=2)C(=O)C(CN)=C1 ZQTJWQQGVDLPHB-UHFFFAOYSA-N 0.000 claims description 3
KFGVZDKURJMNRN-UHFFFAOYSA-N 4-[(4-benzylpiperazin-1-yl)methyl]-2-(cyclopropylmethyl)-6-(3-fluoro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CC2)C(=O)C(CN2CCN(CC=3C=CC=CC=3)CC2)=C1 KFGVZDKURJMNRN-UHFFFAOYSA-N 0.000 claims description 3
ZLVIBLRKIZPTBC-UHFFFAOYSA-N 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-4-(piperazin-1-ylmethyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CCCC=2C=CC(F)=CC=2)C(=O)C(CN2CCNCC2)=C1 ZLVIBLRKIZPTBC-UHFFFAOYSA-N 0.000 claims description 3
HFFMRENNDVYABX-UHFFFAOYSA-N 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-4-[(4-methylpiperazin-1-yl)methyl]pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CCCC=2C=CC(F)=CC=2)C(=O)C(CN2CCN(C)CC2)=C1 HFFMRENNDVYABX-UHFFFAOYSA-N 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
JJJPKKYRGVTAAJ-UHFFFAOYSA-N 2-(cyclopentylmethyl)-4-[(dimethylamino)methyl]-6-(3-fluoro-4-methoxyphenyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CCCC2)C(=O)C(CN(C)C)=C1 JJJPKKYRGVTAAJ-UHFFFAOYSA-N 0.000 claims description 2
HDDOMRKBLRSHGZ-UHFFFAOYSA-N 2-(cyclopentylmethyl)-6-(3-fluoro-4-methoxyphenyl)-4-(piperazin-1-ylmethyl)pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CCCC2)C(=O)C(CN2CCNCC2)=C1 HDDOMRKBLRSHGZ-UHFFFAOYSA-N 0.000 claims description 2
SCYTZLQSLILSLD-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)prop-2-enyl]-6-(3-fluoro-4-methoxyphenyl)-4-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC=CC=2C=CC(Cl)=CC=2)C(=O)C(CN2CCN(CCO)CC2)=C1 SCYTZLQSLILSLD-UHFFFAOYSA-N 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
OKPPIJQFTOWNKH-UHFFFAOYSA-N 4-(diethylaminomethyl)-6-(4-methylphenyl)-2-(2-methylpropyl)pyridazin-3-one Chemical compound CC(C)CN1C(=O)C(CN(CC)CC)=CC(C=2C=CC(C)=CC=2)=N1 OKPPIJQFTOWNKH-UHFFFAOYSA-N 0.000 claims description 2
XXXDOUOTMIJJCN-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-2-(2-methylpropyl)-6-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound C1=CC(SC)=CC=C1C1=NN(CC(C)C)C(=O)C(CN(C)C)=C1 XXXDOUOTMIJJCN-UHFFFAOYSA-N 0.000 claims description 2
KGAVMVHGAWPNAX-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]pyridazin-3-one Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CCCC=2C=CC(F)=CC=2)C(=O)C(CN(C)C)=C1 KGAVMVHGAWPNAX-UHFFFAOYSA-N 0.000 claims description 2
NUSNPWXFTKDJBU-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-6-(3-fluoro-4-methylphenyl)-2-(2-methylpropyl)pyridazin-3-one Chemical compound C1=C(CN(C)C)C(=O)N(CC(C)C)N=C1C1=CC=C(C)C(F)=C1 NUSNPWXFTKDJBU-UHFFFAOYSA-N 0.000 claims description 2
KSAYFOOKNPXMNL-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-6-(4-fluoro-3-methylphenyl)-2-(2-methylpropyl)pyridazin-3-one Chemical compound C1=C(CN(C)C)C(=O)N(CC(C)C)N=C1C1=CC=C(F)C(C)=C1 KSAYFOOKNPXMNL-UHFFFAOYSA-N 0.000 claims description 2
125000005915 C6-C14 aryl group Chemical group 0.000 claims description 2
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
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125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
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150000002431 hydrogen Chemical class 0.000 claims 4
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125000006277 halobenzyl group Chemical group 0.000 claims 1
230000034803 positive regulation of interleukin-10 production Effects 0.000 claims 1
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238000002844 melting Methods 0.000 description 186
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 162
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
PDNPWQDBPWSMIL-UHFFFAOYSA-N methyl 2-(2-methylpropyl)-3-oxo-6-(4-phenylphenyl)pyridazine-4-carboxylate Chemical compound CC(C)CN1C(=O)C(C(=O)OC)=CC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 PDNPWQDBPWSMIL-UHFFFAOYSA-N 0.000 description 2
BECKFPICQFLCHB-UHFFFAOYSA-N methyl 2-(2-methylpropyl)-3-oxo-6-[4-(trifluoromethyl)phenyl]pyridazine-4-carboxylate Chemical compound CC(C)CN1C(=O)C(C(=O)OC)=CC(C=2C=CC(=CC=2)C(F)(F)F)=N1 BECKFPICQFLCHB-UHFFFAOYSA-N 0.000 description 2
LZOOHFYZYUOLLO-UHFFFAOYSA-N methyl 2-(2-methylpropyl)-3-oxo-6-phenylpyridazine-4-carboxylate Chemical compound CC(C)CN1C(=O)C(C(=O)OC)=CC(C=2C=CC=CC=2)=N1 LZOOHFYZYUOLLO-UHFFFAOYSA-N 0.000 description 2
VDEMUDPMUZUWLF-UHFFFAOYSA-N methyl 2-(cyclopentylmethyl)-6-(3-fluoro-4-methoxyphenyl)-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(F)C(OC)=CC=2)=NN1CC1CCCC1 VDEMUDPMUZUWLF-UHFFFAOYSA-N 0.000 description 2
ZGNREBSPCFZQJN-UHFFFAOYSA-N methyl 2-[(3,4-difluorophenyl)methyl]-6-(3-fluoro-4-methoxyphenyl)-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(F)C(OC)=CC=2)=NN1CC1=CC=C(F)C(F)=C1 ZGNREBSPCFZQJN-UHFFFAOYSA-N 0.000 description 2
OLCOJZLMJYZZHJ-UHFFFAOYSA-N methyl 2-[3-(4-chlorophenyl)prop-2-enyl]-6-(3-fluoro-4-methoxyphenyl)-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(F)C(OC)=CC=2)=NN1CC=CC1=CC=C(Cl)C=C1 OLCOJZLMJYZZHJ-UHFFFAOYSA-N 0.000 description 2
SLKSAXVFACCTKM-UHFFFAOYSA-N methyl 2-[3-(4-chlorophenyl)prop-2-enyl]-6-(4-fluoro-3-methylphenyl)-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(C)C(F)=CC=2)=NN1CC=CC1=CC=C(Cl)C=C1 SLKSAXVFACCTKM-UHFFFAOYSA-N 0.000 description 2
TZXWQJGTZRIIMM-UHFFFAOYSA-N methyl 2-benzyl-6-(4-fluoro-3-methylphenyl)-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(C)C(F)=CC=2)=NN1CC1=CC=CC=C1 TZXWQJGTZRIIMM-UHFFFAOYSA-N 0.000 description 2
GQBXJIGTYUSMAE-UHFFFAOYSA-N methyl 3-(2,4-difluorophenyl)-6-oxo-1h-pyridazine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OC)=CC(C=2C(=CC(F)=CC=2)F)=N1 GQBXJIGTYUSMAE-UHFFFAOYSA-N 0.000 description 2
XLMHADUSBWEXQY-UHFFFAOYSA-N methyl 3-(3,4-difluorophenyl)-6-oxo-1h-pyridazine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OC)=CC(C=2C=C(F)C(F)=CC=2)=N1 XLMHADUSBWEXQY-UHFFFAOYSA-N 0.000 description 2
TUCBXWRVKGGVCN-UHFFFAOYSA-N methyl 3-(4-fluoro-3-methylphenyl)-6-oxo-1h-pyridazine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OC)=CC(C=2C=C(C)C(F)=CC=2)=N1 TUCBXWRVKGGVCN-UHFFFAOYSA-N 0.000 description 2
SMPBBHSBUSHJMA-UHFFFAOYSA-N methyl 6-(2,4-difluorophenyl)-2-(2-methylpropyl)-3-oxopyridazine-4-carboxylate Chemical compound CC(C)CN1C(=O)C(C(=O)OC)=CC(C=2C(=CC(F)=CC=2)F)=N1 SMPBBHSBUSHJMA-UHFFFAOYSA-N 0.000 description 2
QJJHAFFIJDXIIY-UHFFFAOYSA-N methyl 6-(3,4-difluorophenyl)-2-(2-methylpropyl)-3-oxopyridazine-4-carboxylate Chemical compound CC(C)CN1C(=O)C(C(=O)OC)=CC(C=2C=C(F)C(F)=CC=2)=N1 QJJHAFFIJDXIIY-UHFFFAOYSA-N 0.000 description 2
XEMOLGKUHFRIRN-UHFFFAOYSA-N methyl 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(F)C(OC)=CC=2)=NN1CCCC1=CC=C(F)C=C1 XEMOLGKUHFRIRN-UHFFFAOYSA-N 0.000 description 2
MYLKHTLZOONBJT-UHFFFAOYSA-N methyl 6-(3-fluoro-4-methylphenyl)-2-(2-methylpropyl)-3-oxopyridazine-4-carboxylate Chemical compound CC(C)CN1C(=O)C(C(=O)OC)=CC(C=2C=C(F)C(C)=CC=2)=N1 MYLKHTLZOONBJT-UHFFFAOYSA-N 0.000 description 2
ZGURIZVZJWFHNN-UHFFFAOYSA-N methyl 6-(4-fluoro-3-methylphenyl)-2-(2-methylpropyl)-3-oxopyridazine-4-carboxylate Chemical compound CC(C)CN1C(=O)C(C(=O)OC)=CC(C=2C=C(C)C(F)=CC=2)=N1 ZGURIZVZJWFHNN-UHFFFAOYSA-N 0.000 description 2
CRMQOAPICXGYIA-UHFFFAOYSA-N methyl 6-(4-fluoro-3-methylphenyl)-3-oxo-2-(3-phenylprop-2-enyl)pyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(C)C(F)=CC=2)=NN1CC=CC1=CC=CC=C1 CRMQOAPICXGYIA-UHFFFAOYSA-N 0.000 description 2
SLFKAGALTMUXFG-UHFFFAOYSA-N methyl 6-(4-methylphenyl)-2-(2-methylpropyl)-3-oxopyridazine-4-carboxylate Chemical compound CC(C)CN1C(=O)C(C(=O)OC)=CC(C=2C=CC(C)=CC=2)=N1 SLFKAGALTMUXFG-UHFFFAOYSA-N 0.000 description 2
CJTLVRMQAJDQPF-UHFFFAOYSA-N methyl 6-oxo-3-(4-phenylphenyl)-1h-pyridazine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OC)=CC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 CJTLVRMQAJDQPF-UHFFFAOYSA-N 0.000 description 2
SKWDNHUXUNZDTL-UHFFFAOYSA-N methyl 6-oxo-3-[4-(trifluoromethyl)phenyl]-1h-pyridazine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OC)=CC(C=2C=CC(=CC=2)C(F)(F)F)=N1 SKWDNHUXUNZDTL-UHFFFAOYSA-N 0.000 description 2
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BJCLHTLPXWRGRO-UHFFFAOYSA-N methyl 2-(cyclopropylmethyl)-6-(4-methylsulfanylphenyl)-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=CC(SC)=CC=2)=NN1CC1CC1 BJCLHTLPXWRGRO-UHFFFAOYSA-N 0.000 description 1
FAIKLSWWBVYYIP-UHFFFAOYSA-N methyl 2-[(4-chlorophenyl)methyl]-6-(3-fluoro-4-methoxyphenyl)-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(F)C(OC)=CC=2)=NN1CC1=CC=C(Cl)C=C1 FAIKLSWWBVYYIP-UHFFFAOYSA-N 0.000 description 1
VWUBXBHXKFMBOS-UHFFFAOYSA-N methyl 3-(4-fluoro-3-methylphenyl)-6-oxopyridazine-1-carboxylate Chemical compound C1=CC(=O)N(C(=O)OC)N=C1C1=CC=C(F)C(C)=C1 VWUBXBHXKFMBOS-UHFFFAOYSA-N 0.000 description 1
UWMNHFFOBFCZOJ-UHFFFAOYSA-N methyl 3-(4-methylphenyl)-6-oxo-1h-pyridazine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OC)=CC(C=2C=CC(C)=CC=2)=N1 UWMNHFFOBFCZOJ-UHFFFAOYSA-N 0.000 description 1
DYEVRNTWNLEAIB-UHFFFAOYSA-N methyl 3-(4-methylsulfanylphenyl)-6-oxo-1h-pyridazine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OC)=CC(C=2C=CC(SC)=CC=2)=N1 DYEVRNTWNLEAIB-UHFFFAOYSA-N 0.000 description 1
HXSNRWBFFONORJ-UHFFFAOYSA-N methyl 6-(3-fluoro-4-methoxyphenyl)-2-[(4-fluorophenyl)methyl]-3-oxopyridazine-4-carboxylate Chemical compound O=C1C(C(=O)OC)=CC(C=2C=C(F)C(OC)=CC=2)=NN1CC1=CC=C(F)C=C1 HXSNRWBFFONORJ-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
229960000965 nimesulide Drugs 0.000 description 1
HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000009290 primary effect Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
239000008213 purified water Substances 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
150000003445 sucroses Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960003676 tenidap Drugs 0.000 description 1
LXIKEPCNDFVJKC-QXMHVHEDSA-N tenidap Chemical compound C12=CC(Cl)=CC=C2N(C(=O)N)C(=O)\C1=C(/O)C1=CC=CS1 LXIKEPCNDFVJKC-QXMHVHEDSA-N 0.000 description 1
KCDDHVZZHLRACM-UHFFFAOYSA-N tert-butyl 4-[5-methyl-2-(2-methylpropyl)-6-(4-methylsulfanylphenyl)-3-oxopyridazin-4-yl]piperazine-1-carboxylate Chemical compound C1=CC(SC)=CC=C1C1=NN(CC(C)C)C(=O)C(N2CCN(CC2)C(=O)OC(C)(C)C)=C1C KCDDHVZZHLRACM-UHFFFAOYSA-N 0.000 description 1
RPBOQCQNVBGYKV-UHFFFAOYSA-N tert-butyl 4-[[2-(2-methylpropyl)-3-oxo-6-(4-phenylphenyl)pyridazin-4-yl]methyl]piperazine-1-carboxylate Chemical compound O=C1N(CC(C)C)N=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1CN1CCN(C(=O)OC(C)(C)C)CC1 RPBOQCQNVBGYKV-UHFFFAOYSA-N 0.000 description 1
FJEMZNWWHONVBB-UHFFFAOYSA-N tert-butyl 4-[[2-(cyclopentylmethyl)-6-(3-fluoro-4-methoxyphenyl)-3-oxopyridazin-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CC2CCCC2)C(=O)C(CN2CCN(CC2)C(=O)OC(C)(C)C)=C1 FJEMZNWWHONVBB-UHFFFAOYSA-N 0.000 description 1
YNLLFGZYQSTQIM-UHFFFAOYSA-N tert-butyl 4-[[6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-3-oxopyridazin-4-yl]methyl]piperazine-1-carboxylate Chemical compound C1=C(F)C(OC)=CC=C1C1=NN(CCCC=2C=CC(F)=CC=2)C(=O)C(CN2CCN(CC2)C(=O)OC(C)(C)C)=C1 YNLLFGZYQSTQIM-UHFFFAOYSA-N 0.000 description 1
LQDWWTYJERWXJA-UHFFFAOYSA-N tert-butyl 4-[[6-(4-fluoro-3-methylphenyl)-2-(2-methylpropyl)-3-oxopyridazin-4-yl]methyl]piperazine-1-carboxylate Chemical compound O=C1N(CC(C)C)N=C(C=2C=C(C)C(F)=CC=2)C=C1CN1CCN(C(=O)OC(C)(C)C)CC1 LQDWWTYJERWXJA-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Rheumatology (AREA)
Epidemiology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Vascular Medicine (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

NO20041250A 2001-09-26 2004-03-25 Vannopploselige fenylpyridazinderivater medisiner inneholdende disse, samt anvendelse av disse for fremstilling av medikamenter for behandling av sykdom NO327425B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US32456901P	2001-09-26	2001-09-26
PCT/JP2002/009863 WO2003027077A1 (en)	2001-09-26	2002-09-25	Water-soluble phenylpyridazine derivatives and drugs containing the same

Publications (2)

Publication Number	Publication Date
NO20041250L NO20041250L (no)	2004-03-25
NO327425B1 true NO327425B1 (no)	2009-06-29

Family

ID=23264178

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20041250A NO327425B1 (no)	2001-09-26	2004-03-25	Vannopploselige fenylpyridazinderivater medisiner inneholdende disse, samt anvendelse av disse for fremstilling av medikamenter for behandling av sykdom

Country Status (16)

Country	Link
US (2)	US6869954B2 (pl)
EP (1)	EP1431293B1 (pl)
JP (1)	JP4280165B2 (pl)
KR (1)	KR20040039377A (pl)
CN (1)	CN1304379C (pl)
AT (1)	ATE512139T1 (pl)
AU (1)	AU2002332286B2 (pl)
BR (1)	BR0212848A (pl)
CA (1)	CA2461806A1 (pl)
HU (1)	HUP0402149A3 (pl)
MX (1)	MXPA04002939A (pl)
NO (1)	NO327425B1 (pl)
NZ (1)	NZ531982A (pl)
PL (1)	PL368340A1 (pl)
RU (1)	RU2302413C2 (pl)
WO (1)	WO2003027077A1 (pl)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1602655A4 (en) *	2003-03-07	2010-06-09	Kowa Co	benzofuran
BRPI0408359A (pt) *	2003-03-18	2006-03-21	Kowa Co	derivados de fenilpiridazina solúveis em água e medicamentos contendo os mesmos
WO2021124346A1 (en) *	2019-12-18	2021-06-24	Abida /	Novel 4-(6-oxo-3-substituted phenylpyridazin-1(6 h)-yl)benzaldehydes of pharmaceutical interest
GB202311227D0 (en) *	2023-07-21	2023-09-06	Almac Discovery Ltd	Pharmaceutical compounds

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4404203A (en) *	1981-05-14	1983-09-13	Warner-Lambert Company	Substituted 6-phenyl-3(2H)-pyridazinones useful as cardiotonic agents
DE4134467A1 (de) *	1991-10-18	1993-04-22	Thomae Gmbh Dr K	Heterobiarylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
CA2283399C (en) *	1997-03-14	2006-02-21	Merck Frosst Canada & Co.	Pyridazinones as inhibitors of cyclooxygenase-2
EP2017266A1 (en) *	1997-11-19	2009-01-21	Kowa Co., Ltd.	Pyridazine derivatives and medicines containing the same as effective ingredients
TWI241295B (en) *	1998-03-02	2005-10-11	Kowa Co	Pyridazine derivative and medicine containing the same as effect component
JP2000247959A (ja)	1999-02-26	2000-09-12	Kowa Co	ピリダジン−３−オン誘導体及びこれを含有する医薬
US6664256B1 (en)	2000-07-10	2003-12-16	Kowa Co., Ltd.	Phenylpyridazine compounds and medicines containing the same
CA2742411A1 (en) *	2000-09-18	2002-03-21	Eisai R&D Management Co., Ltd.	Pyridazinone and triazinone compounds and use thereof as pharmaceutical preparations
US6861428B2 (en)	2001-09-26	2005-03-01	Kowa Co., Ltd.	Water-soluble phenylpyridazine compounds and compositions containing the same

2002
- 2002-09-25 AU AU2002332286A patent/AU2002332286B2/en not_active Ceased
- 2002-09-25 US US10/253,523 patent/US6869954B2/en not_active Expired - Fee Related
- 2002-09-25 JP JP2003530668A patent/JP4280165B2/ja not_active Expired - Lifetime
- 2002-09-25 MX MXPA04002939A patent/MXPA04002939A/es active IP Right Grant
- 2002-09-25 CN CNB02818940XA patent/CN1304379C/zh not_active Expired - Fee Related
- 2002-09-25 WO PCT/JP2002/009863 patent/WO2003027077A1/ja not_active Ceased
- 2002-09-25 BR BR0212848-9A patent/BR0212848A/pt not_active IP Right Cessation
- 2002-09-25 KR KR10-2004-7003995A patent/KR20040039377A/ko not_active Ceased
- 2002-09-25 CA CA002461806A patent/CA2461806A1/en not_active Abandoned
- 2002-09-25 RU RU2004112532/04A patent/RU2302413C2/ru not_active IP Right Cessation
- 2002-09-25 PL PL02368340A patent/PL368340A1/pl not_active Application Discontinuation
- 2002-09-25 NZ NZ531982A patent/NZ531982A/en not_active IP Right Cessation
- 2002-09-25 AT AT02768055T patent/ATE512139T1/de not_active IP Right Cessation
- 2002-09-25 HU HU0402149A patent/HUP0402149A3/hu unknown
- 2002-09-25 EP EP02768055A patent/EP1431293B1/en not_active Expired - Lifetime
2004
- 2004-03-25 NO NO20041250A patent/NO327425B1/no not_active IP Right Cessation
- 2004-10-12 US US10/960,993 patent/US7087606B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
MXPA04002939A (es)	2004-06-18
AU2002332286B2 (en)	2007-10-18
HUP0402149A3 (en)	2005-08-29
US20050085480A1 (en)	2005-04-21
NZ531982A (en)	2005-08-26
PL368340A1 (pl)	2005-03-21
US6869954B2 (en)	2005-03-22
HUP0402149A2 (hu)	2005-02-28
WO2003027077A1 (en)	2003-04-03
ATE512139T1 (de)	2011-06-15
US7087606B2 (en)	2006-08-08
BR0212848A (pt)	2004-08-17
EP1431293A4 (en)	2004-12-22
CA2461806A1 (en)	2003-04-03
EP1431293B1 (en)	2011-06-08
EP1431293A1 (en)	2004-06-23
CN1304379C (zh)	2007-03-14
US20030119838A1 (en)	2003-06-26
RU2302413C2 (ru)	2007-07-10
NO20041250L (no)	2004-03-25
HK1070068A1 (en)	2005-06-10
JPWO2003027077A1 (ja)	2005-01-06
CN1558903A (zh)	2004-12-29
KR20040039377A (ko)	2004-05-10
JP4280165B2 (ja)	2009-06-17
RU2004112532A (ru)	2005-03-27

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Date	Code	Title	Description
2011-05-09	MM1K	Lapsed by not paying the annual fees

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