JP2001515893A5 - - Google Patents
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- Publication number
- JP2001515893A5 JP2001515893A5 JP2000510724A JP2000510724A JP2001515893A5 JP 2001515893 A5 JP2001515893 A5 JP 2001515893A5 JP 2000510724 A JP2000510724 A JP 2000510724A JP 2000510724 A JP2000510724 A JP 2000510724A JP 2001515893 A5 JP2001515893 A5 JP 2001515893A5
- Authority
- JP
- Japan
- Prior art keywords
- benzo
- phenyl
- thiazine
- dioxo
- dihydro
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 description 57
- -1 aryl zinc bromide Chemical compound 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- BNNNRTHFDVJELR-UHFFFAOYSA-N 2h-thiazine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CSN1 BNNNRTHFDVJELR-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 210000003038 endothelium Anatomy 0.000 description 3
- 210000001105 femoral artery Anatomy 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 210000001147 pulmonary artery Anatomy 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 229940102001 zinc bromide Drugs 0.000 description 3
- DIXQNPMNNNHBJM-UHFFFAOYSA-N 2-(2-benzylphenyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound C=1C=2OCOC=2C(OC)=CC=1C(C1=CC=CC=C1S1(=O)=O)=C(C(O)=O)N1C1=CC=CC=C1CC1=CC=CC=C1 DIXQNPMNNNHBJM-UHFFFAOYSA-N 0.000 description 2
- FNFVXWQEIZDWFQ-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(3,5-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound COC1=CC(OC)=CC(C=2C3=CC=CC=C3S(=O)(=O)N(C=3C(=CC=CC=3)Br)C=2C(O)=O)=C1 FNFVXWQEIZDWFQ-UHFFFAOYSA-N 0.000 description 2
- BEXSXXLLFTXMTM-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound C=1C=2OCOC=2C(OC)=CC=1C(C1=CC=CC=C1S1(=O)=O)=C(C(O)=O)N1C1=CC=CC=C1Br BEXSXXLLFTXMTM-UHFFFAOYSA-N 0.000 description 2
- IISCGVRQYYMFRH-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(3,5-dimethoxyphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound COC1=CC(OC)=CC(C=2C3=CC=CC=C3S(=O)(=O)N(C=3C(=CC=CC=3)Cl)C=2C(O)=O)=C1 IISCGVRQYYMFRH-UHFFFAOYSA-N 0.000 description 2
- AMQWLQQHYSWEKW-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound C=1C=2OCOC=2C(OC)=CC=1C(C1=CC=CC=C1S1(=O)=O)=C(C(O)=O)N1C1=CC=CC=C1Cl AMQWLQQHYSWEKW-UHFFFAOYSA-N 0.000 description 2
- TZKOBJCQNUBVFU-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-1,1-dioxo-2-(2-propan-2-ylphenyl)-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound CC(C)C1=CC=CC=C1N1S(=O)(=O)C2=CC=CC=C2C(C=2C=C3OCOC3=CC=2)=C1C(O)=O TZKOBJCQNUBVFU-UHFFFAOYSA-N 0.000 description 2
- JPLQUTNXYCOLMJ-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-1,1-dioxo-2-(2-propylphenyl)-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound CCCC1=CC=CC=C1N1S(=O)(=O)C2=CC=CC=C2C(C=2C=C3OCOC3=CC=2)=C1C(O)=O JPLQUTNXYCOLMJ-UHFFFAOYSA-N 0.000 description 2
- OCXPJPDSHYADDP-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-1,1-dioxo-2-(2-pyrrol-1-ylphenyl)-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(C=2C=C3OCOC3=CC=2)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1N1C=CC=C1 OCXPJPDSHYADDP-UHFFFAOYSA-N 0.000 description 2
- FTMWYVPNIARZOL-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-1,1-dioxo-2-[2-(trifluoromethyl)phenyl]-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(C=2C=C3OCOC3=CC=2)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1C(F)(F)F FTMWYVPNIARZOL-UHFFFAOYSA-N 0.000 description 2
- WSMUYLAUHRRHKC-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2,3-dichlorophenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(C=2C=C3OCOC3=CC=2)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC(Cl)=C1Cl WSMUYLAUHRRHKC-UHFFFAOYSA-N 0.000 description 2
- FWCQSVCEKBXIPV-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2,4-dichlorophenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(C=2C=C3OCOC3=CC=2)C2=CC=CC=C2S(=O)(=O)N1C1=CC=C(Cl)C=C1Cl FWCQSVCEKBXIPV-UHFFFAOYSA-N 0.000 description 2
- SWOWNAALUBWJMY-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2,6-dimethylphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound CC1=CC=CC(C)=C1N1S(=O)(=O)C2=CC=CC=C2C(C=2C=C3OCOC3=CC=2)=C1C(O)=O SWOWNAALUBWJMY-UHFFFAOYSA-N 0.000 description 2
- DZRKBTOLNPQETC-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2-butylphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound CCCCC1=CC=CC=C1N1S(=O)(=O)C2=CC=CC=C2C(C=2C=C3OCOC3=CC=2)=C1C(O)=O DZRKBTOLNPQETC-UHFFFAOYSA-N 0.000 description 2
- BRLVMBSIWOVEPW-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2-chloro-4-methoxyphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound ClC1=CC(OC)=CC=C1N1S(=O)(=O)C2=CC=CC=C2C(C=2C=C3OCOC3=CC=2)=C1C(O)=O BRLVMBSIWOVEPW-UHFFFAOYSA-N 0.000 description 2
- KNBXCNUDTCRKBB-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2-ethylphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound CCC1=CC=CC=C1N1S(=O)(=O)C2=CC=CC=C2C(C=2C=C3OCOC3=CC=2)=C1C(O)=O KNBXCNUDTCRKBB-UHFFFAOYSA-N 0.000 description 2
- ANZRAEROGOTRGG-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2-fluorophenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(C=2C=C3OCOC3=CC=2)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1F ANZRAEROGOTRGG-UHFFFAOYSA-N 0.000 description 2
- KSHBAROYLRSNSR-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(C=2C=C3OCOC3=CC=2)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1O KSHBAROYLRSNSR-UHFFFAOYSA-N 0.000 description 2
- ZZTANUUBVUXDBR-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(3-chloro-2-methylphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound CC1=C(Cl)C=CC=C1N1S(=O)(=O)C2=CC=CC=C2C(C=2C=C3OCOC3=CC=2)=C1C(O)=O ZZTANUUBVUXDBR-UHFFFAOYSA-N 0.000 description 2
- UVZUDXPQKIVQQH-UHFFFAOYSA-N 4-(3,5-dimethoxyphenyl)-1,1-dioxo-2-[2-(trifluoromethyl)phenyl]-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound COC1=CC(OC)=CC(C=2C3=CC=CC=C3S(=O)(=O)N(C=3C(=CC=CC=3)C(F)(F)F)C=2C(O)=O)=C1 UVZUDXPQKIVQQH-UHFFFAOYSA-N 0.000 description 2
- QKWAXELVVACFSW-UHFFFAOYSA-N 4-(7-methoxy-1,3-benzodioxol-5-yl)-1,1-dioxo-2-[2-(trifluoromethyl)phenyl]-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound C=1C=2OCOC=2C(OC)=CC=1C(C1=CC=CC=C1S1(=O)=O)=C(C(O)=O)N1C1=CC=CC=C1C(F)(F)F QKWAXELVVACFSW-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 206010047139 Vasoconstriction Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052736 halogen Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- OBVZSUMIYCNREA-UHFFFAOYSA-M sodium;2-(2,6-dimethylphenyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound [Na+].C=1C=2OCOC=2C(OC)=CC=1C(C1=CC=CC=C1S1(=O)=O)=C(C([O-])=O)N1C1=C(C)C=CC=C1C OBVZSUMIYCNREA-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 210000000689 upper leg Anatomy 0.000 description 2
- 230000025033 vasoconstriction Effects 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- YVSFMGPSNBYSKS-UHFFFAOYSA-N 2-(2-bromophenyl)-4-hydroxy-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(O)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1Br YVSFMGPSNBYSKS-UHFFFAOYSA-N 0.000 description 1
- JBUHRZPSPVCNEK-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-hydroxy-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(O)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1Cl JBUHRZPSPVCNEK-UHFFFAOYSA-N 0.000 description 1
- HPNDLPIDCCRPQW-UHFFFAOYSA-N 2-(6-chloro-1,3-benzodioxol-5-yl)-4-hydroxy-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(O)C2=CC=CC=C2S(=O)(=O)N1C(C(=C1)Cl)=CC2=C1OCO2 HPNDLPIDCCRPQW-UHFFFAOYSA-N 0.000 description 1
- YMRUIRRQMVWHTM-UHFFFAOYSA-N 3-bromo-5-(2-hydroxyethyl)phenol Chemical compound OCCC1=CC(O)=CC(Br)=C1 YMRUIRRQMVWHTM-UHFFFAOYSA-N 0.000 description 1
- DCHMSSPUFCVFEF-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-2-(2-benzylphenyl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylic acid Chemical compound OC(=O)C1=C(C=2C=C3OCOC3=CC=2)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1CC1=CC=CC=C1 DCHMSSPUFCVFEF-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
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- LOFRBHZYZCIOJO-UHFFFAOYSA-N 7-methoxy-1,3-benzodioxole-5-carbaldehyde Chemical compound COC1=CC(C=O)=CC2=C1OCO2 LOFRBHZYZCIOJO-UHFFFAOYSA-N 0.000 description 1
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- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
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- 206010028980 Neoplasm Diseases 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
- 208000006906 Vascular Ring Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
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- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
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- AXVBHTJOOOGJHO-UHFFFAOYSA-N methyl 2-[(2-methoxy-2-oxoethyl)-(2-propylphenyl)sulfamoyl]benzoate Chemical compound CCCC1=CC=CC=C1N(CC(=O)OC)S(=O)(=O)C1=CC=CC=C1C(=O)OC AXVBHTJOOOGJHO-UHFFFAOYSA-N 0.000 description 1
- STLOMWCRUIROQT-UHFFFAOYSA-N methyl 2-[(2-propylphenyl)sulfamoyl]benzoate Chemical compound CCCC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1C(=O)OC STLOMWCRUIROQT-UHFFFAOYSA-N 0.000 description 1
- QVNAUWXKTOKOGD-UHFFFAOYSA-N methyl 2h-thiazine-3-carboxylate Chemical compound COC(=O)C1=CC=CSN1 QVNAUWXKTOKOGD-UHFFFAOYSA-N 0.000 description 1
- FLDNYTCEDRUCEE-UHFFFAOYSA-N methyl 4-hydroxy-1,1-dioxo-2-(2-propylphenyl)-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound CCCC1=CC=CC=C1N1S(=O)(=O)C2=CC=CC=C2C(O)=C1C(=O)OC FLDNYTCEDRUCEE-UHFFFAOYSA-N 0.000 description 1
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 201000011461 pre-eclampsia Diseases 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PYWBTFHUCPUVCJ-UHFFFAOYSA-M sodium;2-(2-bromophenyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound [Na+].C=1C=2OCOC=2C(OC)=CC=1C(C1=CC=CC=C1S1(=O)=O)=C(C([O-])=O)N1C1=CC=CC=C1Br PYWBTFHUCPUVCJ-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- SUOANRQHLMPIPV-UHFFFAOYSA-N tert-butyl 2-(2-bromophenyl)-4-hydroxy-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound CC(C)(C)OC(=O)C1=C(O)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1Br SUOANRQHLMPIPV-UHFFFAOYSA-N 0.000 description 1
- IQFZCCCFDPHKPJ-UHFFFAOYSA-N tert-butyl 2-(2-chlorophenyl)-4-hydroxy-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound CC(C)(C)OC(=O)C1=C(O)C2=CC=CC=C2S(=O)(=O)N1C1=CC=CC=C1Cl IQFZCCCFDPHKPJ-UHFFFAOYSA-N 0.000 description 1
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| US5811197P | 1997-09-05 | 1997-09-05 | |
| US60/058,111 | 1997-09-05 | ||
| US9232698P | 1998-07-09 | 1998-07-09 | |
| US60/092,326 | 1998-07-09 | ||
| PCT/US1998/016856 WO1999012916A1 (en) | 1997-09-05 | 1998-08-13 | Certain benzothiazine dioxide endothelin antagonists and processes for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001515893A JP2001515893A (ja) | 2001-09-25 |
| JP2001515893A5 true JP2001515893A5 (https=) | 2006-02-16 |
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| JP2000510724A Abandoned JP2001515893A (ja) | 1997-09-05 | 1998-08-13 | 特定のベンゾチアジンジオキシドエンドセリンアンタゴニスト類およびその製造方法 |
Country Status (24)
| Country | Link |
|---|---|
| US (5) | US6265399B1 (https=) |
| EP (1) | EP1009743B1 (https=) |
| JP (1) | JP2001515893A (https=) |
| KR (1) | KR20010023686A (https=) |
| AR (1) | AR017056A1 (https=) |
| AT (1) | ATE270281T1 (https=) |
| AU (1) | AU759169B2 (https=) |
| BR (1) | BR9812431A (https=) |
| CA (1) | CA2296358A1 (https=) |
| CO (1) | CO4970725A1 (https=) |
| DE (1) | DE69824863T2 (https=) |
| ES (1) | ES2221191T3 (https=) |
| HU (1) | HUP0003689A3 (https=) |
| IL (1) | IL134057A0 (https=) |
| IS (1) | IS5356A (https=) |
| MY (1) | MY116277A (https=) |
| NO (1) | NO20001078L (https=) |
| NZ (1) | NZ502670A (https=) |
| PE (1) | PE116699A1 (https=) |
| PL (1) | PL338983A1 (https=) |
| PT (1) | PT1009743E (https=) |
| TW (1) | TW508355B (https=) |
| UY (1) | UY25168A1 (https=) |
| WO (1) | WO1999012916A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU759169B2 (en) | 1997-09-05 | 2003-04-10 | Warner-Lambert Company | Certain benzothiazine dioxide endothelin antagonists and processes for their preparation |
| EP1288199A4 (en) | 2000-04-28 | 2005-10-12 | Shionogi & Co | INHIBITORS OF MMP-12 |
| WO2001091736A2 (en) * | 2000-05-31 | 2001-12-06 | Warner-Lambert Company | Combinations of an endothelin receptor antagonist and an antiepileptic compound having pain alleviating properties or analgesic |
| US20020115661A1 (en) * | 2000-12-07 | 2002-08-22 | Keller Laurence Harvey | Method for treating chronic obstructive pulmonary disease |
| CN1882327A (zh) | 2003-11-19 | 2006-12-20 | 症变治疗公司 | 含磷的新的拟甲状腺素药 |
| FR2874011B1 (fr) * | 2004-08-03 | 2007-06-15 | Sanofi Synthelabo | Derives de sulfonamides, leur preparation et leur application en therapeutique |
| DE102008026894A1 (de) * | 2008-06-05 | 2009-12-10 | Evonik Degussa Gmbh | Ink Jet Tinte |
| CA2969756A1 (en) * | 2014-12-05 | 2016-06-09 | Aquinnah Pharmaceuticals, Inc. | Sulfonamide derivatives, compositions and methods of use in the treatment of neurodegenerative diseases |
| CN108727176B (zh) * | 2018-07-26 | 2021-05-18 | 荆楚理工学院 | 一种制备5-卤-2,3-二羟基苯甲醛的方法 |
| CN113214299A (zh) * | 2021-03-01 | 2021-08-06 | 重庆西南制药二厂有限责任公司 | γ-联苯双酯中间体及合成方法及γ-联苯双酯合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960856A (en) * | 1975-06-20 | 1976-06-01 | Warner-Lambert Company | Process for the preparation of 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide |
| IN159273B (https=) * | 1981-10-05 | 1987-04-25 | Pfizer | |
| JPH0495057A (ja) * | 1990-08-08 | 1992-03-27 | Taisho Pharmaceut Co Ltd | Ｎ―置換スルホンアニリド化合物 |
| AU675870B2 (en) * | 1993-08-18 | 1997-02-20 | Msd K.K. | Endothelin antagonistic heteroaromatic ring-fused cyclopentene derivatives |
| US5389620A (en) | 1993-08-18 | 1995-02-14 | Banyu Pharmaceutical Co., Ltd. | Endothelin antagonistic heteroaromatic ring-fused cyclopentene derivatives |
| CA2156849A1 (en) | 1993-12-24 | 1995-07-06 | Akira Mizuno | Benzothiazine derivative |
| JPH0912562A (ja) | 1995-06-22 | 1997-01-14 | Suntory Ltd | 置換ベンゾチアジン誘導体 |
| US5482960A (en) | 1994-11-14 | 1996-01-09 | Warner-Lambert Company | Nonpeptide endothelin antagonists |
| US5599811A (en) * | 1995-02-21 | 1997-02-04 | Warner-Lambert Company | Benzothiazine dioxides as endothelin antagonists |
| CA2190708A1 (en) | 1995-12-08 | 1997-06-09 | Johannes Aebi | Aminoalkyl substituted benzo-heterocyclic compounds |
| AU759169B2 (en) | 1997-09-05 | 2003-04-10 | Warner-Lambert Company | Certain benzothiazine dioxide endothelin antagonists and processes for their preparation |
-
1998
- 1998-08-13 AU AU90196/98A patent/AU759169B2/en not_active Ceased
- 1998-08-13 WO PCT/US1998/016856 patent/WO1999012916A1/en not_active Ceased
- 1998-08-13 KR KR1020007002339A patent/KR20010023686A/ko not_active Withdrawn
- 1998-08-13 EP EP98942061A patent/EP1009743B1/en not_active Expired - Lifetime
- 1998-08-13 NZ NZ502670A patent/NZ502670A/xx unknown
- 1998-08-13 ES ES98942061T patent/ES2221191T3/es not_active Expired - Lifetime
- 1998-08-13 JP JP2000510724A patent/JP2001515893A/ja not_active Abandoned
- 1998-08-13 HU HU0003689A patent/HUP0003689A3/hu unknown
- 1998-08-13 AT AT98942061T patent/ATE270281T1/de not_active IP Right Cessation
- 1998-08-13 CA CA002296358A patent/CA2296358A1/en not_active Abandoned
- 1998-08-13 PT PT98942061T patent/PT1009743E/pt unknown
- 1998-08-13 PL PL98338983A patent/PL338983A1/xx unknown
- 1998-08-13 IL IL13405798A patent/IL134057A0/xx unknown
- 1998-08-13 BR BR9812431-5A patent/BR9812431A/pt not_active Application Discontinuation
- 1998-08-13 US US09/445,504 patent/US6265399B1/en not_active Expired - Fee Related
- 1998-08-13 DE DE69824863T patent/DE69824863T2/de not_active Expired - Fee Related
- 1998-09-03 MY MYPI98004024A patent/MY116277A/en unknown
- 1998-09-04 PE PE1998000822A patent/PE116699A1/es not_active Application Discontinuation
- 1998-09-04 UY UY25168A patent/UY25168A1/es not_active IP Right Cessation
- 1998-09-04 AR ARP980104414A patent/AR017056A1/es unknown
- 1998-09-04 CO CO98050781A patent/CO4970725A1/es unknown
- 1998-10-28 TW TW087114760A patent/TW508355B/zh not_active IP Right Cessation
-
2000
- 2000-01-21 IS IS5356A patent/IS5356A/is unknown
- 2000-03-02 NO NO20001078A patent/NO20001078L/no unknown
- 2000-08-07 US US09/633,720 patent/US6252070B1/en not_active Expired - Fee Related
-
2001
- 2001-03-27 US US09/818,394 patent/US6440962B2/en not_active Expired - Fee Related
- 2001-12-05 US US10/006,589 patent/US6545150B2/en not_active Expired - Fee Related
-
2002
- 2002-06-03 US US10/161,569 patent/US20030073684A1/en not_active Abandoned
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