NO874850L - Fremgangsmaate for fremstilling av benzotiadiazinforbindelser og farmasoeytisk akseptable salter derav. - Google Patents
Fremgangsmaate for fremstilling av benzotiadiazinforbindelser og farmasoeytisk akseptable salter derav.Info
- Publication number
- NO874850L NO874850L NO874850A NO874850A NO874850L NO 874850 L NO874850 L NO 874850L NO 874850 A NO874850 A NO 874850A NO 874850 A NO874850 A NO 874850A NO 874850 L NO874850 L NO 874850L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- nmr
- nujol
- dioxide
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 83
- 150000003839 salts Chemical class 0.000 title claims description 61
- 238000000034 method Methods 0.000 title claims description 41
- 238000002360 preparation method Methods 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 92
- -1 amino, carboxy Chemical group 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 71
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000003379 elimination reaction Methods 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- DAHOOCQZIXPFHL-SNVBAGLBSA-N (2r)-2-[[2-(4-chlorophenyl)-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoic acid Chemical compound C=1C(O[C@H](C)C(O)=O)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=C(Cl)C=C1 DAHOOCQZIXPFHL-SNVBAGLBSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 107
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 95
- 239000000203 mixture Substances 0.000 description 54
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 101150041968 CDC13 gene Proteins 0.000 description 15
- 239000002253 acid Chemical group 0.000 description 15
- 239000002585 base Substances 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 150000007529 inorganic bases Chemical class 0.000 description 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002411 adverse Effects 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- UJURMMNUSWYNNQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-hydroxy-4-methyl-1,1-dioxo-1$l^{6},2,4-benzothiadiazin-3-one Chemical compound O=S1(=O)C2=CC=C(O)C=C2N(C)C(=O)N1C1=CC=C(Cl)C=C1 UJURMMNUSWYNNQ-UHFFFAOYSA-N 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- DAHOOCQZIXPFHL-UHFFFAOYSA-N 2-[[2-(4-chlorophenyl)-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoic acid Chemical compound C=1C(OC(C)C(O)=O)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=C(Cl)C=C1 DAHOOCQZIXPFHL-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 229940125890 compound Ia Drugs 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CROPERLEGVRULM-LLVKDONJSA-N (2r)-2-[(2-cyclohexyl-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl)oxy]propanoic acid Chemical compound C=1C(O[C@H](C)C(O)=O)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1CCCCC1 CROPERLEGVRULM-LLVKDONJSA-N 0.000 description 3
- ALBBOGOWSQJHTN-LLVKDONJSA-N (2r)-2-[(4-methyl-1,1,3-trioxo-2-phenyl-1$l^{6},2,4-benzothiadiazin-6-yl)oxy]propanoic acid Chemical compound C=1C(O[C@H](C)C(O)=O)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=CC=C1 ALBBOGOWSQJHTN-LLVKDONJSA-N 0.000 description 3
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- WZNXINPPSAVBCY-UHFFFAOYSA-N cyclohexylmethyl 4-[6-(cyclohexylmethoxy)-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-2-yl]benzoate Chemical compound O=S1(=O)C2=CC=C(OCC3CCCCC3)C=C2N(C)C(=O)N1C(C=C1)=CC=C1C(=O)OCC1CCCCC1 WZNXINPPSAVBCY-UHFFFAOYSA-N 0.000 description 2
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- QWEABDLHBNFNID-CYBMUJFWSA-N ethyl (2r)-2-[(4-methyl-1,1,3-trioxo-2-phenyl-1$l^{6},2,4-benzothiadiazin-6-yl)oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=CC=C1 QWEABDLHBNFNID-CYBMUJFWSA-N 0.000 description 2
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- PPJQUJPHGVDTBG-GFCCVEGCSA-N ethyl (2r)-2-[[2-(2-chlorophenyl)-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=CC=C1Cl PPJQUJPHGVDTBG-GFCCVEGCSA-N 0.000 description 2
- XRPKQZGGKDQZNI-LLVKDONJSA-N ethyl (2r)-2-[[2-(3,4-dichlorophenyl)-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=C(Cl)C(Cl)=C1 XRPKQZGGKDQZNI-LLVKDONJSA-N 0.000 description 2
- KCPNSTDWENRZDQ-GFCCVEGCSA-N ethyl (2r)-2-[[2-(3-chlorophenyl)-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=CC(Cl)=C1 KCPNSTDWENRZDQ-GFCCVEGCSA-N 0.000 description 2
- FUVXVVZIHVYMIL-GFCCVEGCSA-N ethyl (2r)-2-[[2-(4-chlorophenyl)-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=C(Cl)C=C1 FUVXVVZIHVYMIL-GFCCVEGCSA-N 0.000 description 2
- YMHIFWVXNBRULR-GFCCVEGCSA-N ethyl (2r)-2-[[2-(4-fluorophenyl)-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=C(F)C=C1 YMHIFWVXNBRULR-GFCCVEGCSA-N 0.000 description 2
- FWWCKIMVGYQSEL-CQSZACIVSA-N ethyl (2r)-2-[[2-[4-(dimethylamino)phenyl]-4-methyl-1,1,3-trioxo-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=C(N(C)C)C=C1 FWWCKIMVGYQSEL-CQSZACIVSA-N 0.000 description 2
- CZZBBKQCBQKOPK-QGZVFWFLSA-N ethyl (2r)-2-[[4-methyl-1,1,3-trioxo-2-(4-phenoxyphenyl)-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C(C=C1)=CC=C1OC1=CC=CC=C1 CZZBBKQCBQKOPK-QGZVFWFLSA-N 0.000 description 2
- NUEJIADGGHGIDC-OAHLLOKOSA-N ethyl (2r)-2-[[4-methyl-1,1,3-trioxo-2-(4-propan-2-ylphenyl)-1$l^{6},2,4-benzothiadiazin-6-yl]oxy]propanoate Chemical compound C=1C(O[C@H](C)C(=O)OCC)=CC=C(S2(=O)=O)C=1N(C)C(=O)N2C1=CC=C(C(C)C)C=C1 NUEJIADGGHGIDC-OAHLLOKOSA-N 0.000 description 2
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
- RNUGYAMXCLOXGV-UHFFFAOYSA-N n-(2-chlorophenyl)-4-methoxy-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=CC=C1Cl RNUGYAMXCLOXGV-UHFFFAOYSA-N 0.000 description 1
- QGUCPGVDXVGCNF-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-4-methoxy-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 QGUCPGVDXVGCNF-UHFFFAOYSA-N 0.000 description 1
- UAKBINKARMLJCW-UHFFFAOYSA-N n-(3-chlorophenyl)-4-methoxy-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=CC(Cl)=C1 UAKBINKARMLJCW-UHFFFAOYSA-N 0.000 description 1
- KBSSANLETBADQA-UHFFFAOYSA-N n-(4-chlorophenyl)-2-nitro-4-(trifluoromethyl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 KBSSANLETBADQA-UHFFFAOYSA-N 0.000 description 1
- RTXJXTAEAXCKRI-UHFFFAOYSA-N n-(4-chlorophenyl)-2-nitro-4-propan-2-yloxybenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC(C)C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 RTXJXTAEAXCKRI-UHFFFAOYSA-N 0.000 description 1
- MNHIVKRGHVGPIJ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 MNHIVKRGHVGPIJ-UHFFFAOYSA-N 0.000 description 1
- SQTODWBROMJWLV-UHFFFAOYSA-N n-(4-chlorophenyl)-4-methyl-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 SQTODWBROMJWLV-UHFFFAOYSA-N 0.000 description 1
- AJQBJLKAQYXBJI-UHFFFAOYSA-N n-(4-fluorophenyl)-4-methoxy-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(F)C=C1 AJQBJLKAQYXBJI-UHFFFAOYSA-N 0.000 description 1
- HHUDOHSHCQWBCD-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-methoxy-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1S(=O)(=O)NCC1=CC=C(Cl)C=C1 HHUDOHSHCQWBCD-UHFFFAOYSA-N 0.000 description 1
- XUEZCVAFJIUWBY-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-1,1,3-trioxo-4h-1$l^{6},2,4-benzothiadiazin-6-yl]acetamide Chemical compound C=1C(NC(=O)C)=CC=C(S2(=O)=O)C=1NC(=O)N2C1=CC=C(Cl)C=C1 XUEZCVAFJIUWBY-UHFFFAOYSA-N 0.000 description 1
- DXZKIPATWVKBRQ-UHFFFAOYSA-N n-[3-amino-4-[(4-chlorophenyl)sulfamoyl]phenyl]acetamide Chemical compound NC1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 DXZKIPATWVKBRQ-UHFFFAOYSA-N 0.000 description 1
- WEOQHXKWINAXSQ-UHFFFAOYSA-N n-[4-(dimethylamino)phenyl]-4-methoxy-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(N(C)C)C=C1 WEOQHXKWINAXSQ-UHFFFAOYSA-N 0.000 description 1
- DINRKJYGQJEFSH-UHFFFAOYSA-N n-cyclohexyl-4-methoxy-2-nitrobenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1S(=O)(=O)NC1CCCCC1 DINRKJYGQJEFSH-UHFFFAOYSA-N 0.000 description 1
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N ornithyl group Chemical class N[C@@H](CCCN)C(=O)O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- ILFAMWTZLTUIFI-UHFFFAOYSA-N propan-2-yl 4-(4-methyl-1,1,3-trioxo-6-propan-2-yloxy-1$l^{6},2,4-benzothiadiazin-2-yl)butanoate Chemical compound CC(C)OC1=CC=C2S(=O)(=O)N(CCCC(=O)OC(C)C)C(=O)N(C)C2=C1 ILFAMWTZLTUIFI-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- 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
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868627857A GB8627857D0 (en) | 1986-11-21 | 1986-11-21 | Benzothiadiazine compounds |
| GB878714598A GB8714598D0 (en) | 1987-06-22 | 1987-06-22 | Benzothiadiazine compounds |
| GB878720659A GB8720659D0 (en) | 1987-09-02 | 1987-09-02 | Benzothiadiazine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO874850D0 NO874850D0 (no) | 1987-11-20 |
| NO874850L true NO874850L (no) | 1988-05-24 |
Family
ID=27263212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO874850A NO874850L (no) | 1986-11-21 | 1987-11-20 | Fremgangsmaate for fremstilling av benzotiadiazinforbindelser og farmasoeytisk akseptable salter derav. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4889851A (fi) |
| EP (1) | EP0268990A3 (fi) |
| JP (1) | JP2564860B2 (fi) |
| KR (1) | KR880006219A (fi) |
| CN (1) | CN87107990A (fi) |
| AU (1) | AU603842B2 (fi) |
| DK (1) | DK597387A (fi) |
| FI (1) | FI875086A (fi) |
| NO (1) | NO874850L (fi) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ223237A (en) * | 1987-01-22 | 1991-03-26 | Shiseido Co Ltd | Hair growth promoting agent and compositions |
| AU5883794A (en) * | 1993-01-20 | 1994-08-15 | A. Menarini Industrie Farmaceutiche Riunite S.R.L. | Diazepin derivatives and antiviral compositions |
| FR2710062B1 (fr) * | 1993-09-17 | 1995-12-01 | Rhone Poulenc Rorer Sa | Dérivés d'acide 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxyde-3-carboxylique, leur préparation et les médicaments les contenant. |
| US6008208A (en) | 1995-10-23 | 1999-12-28 | Osteoscreen, Inc. | Compositions and methods for treating bone deficit conditions |
| CZ115398A3 (cs) * | 1995-10-23 | 1998-12-16 | Zymogenetics, Inc. | Přípravky a způsoby pro léčbu deficitních stavů kostí |
| EP0973513A4 (en) * | 1996-10-23 | 2003-03-19 | Zymogenetics Inc | COMPOSITIONS AND METHODS FOR TREATING CONDITIONS ASSOCIATED WITH BONE DEFICIT |
| JP2002514192A (ja) * | 1996-11-13 | 2002-05-14 | セフアロン・インコーポレーテツド | ベンゾチアゾおよび関連の複素環基を含有するシステインおよびセリンプロテアーゼ阻害剤 |
| US5952328A (en) * | 1997-11-12 | 1999-09-14 | Cephalon, Inc. | Benzothiazo and related heterocyclic group-containing cysteine and serine protease inhibitors |
| EP1173223A2 (en) | 1999-04-30 | 2002-01-23 | Slil Biomedical Corporation | Conjugates as therapies for cancers and prostate diseases |
| CA2431709A1 (en) * | 2000-12-16 | 2002-06-20 | Aventis Pharma Deutschland Gmbh | Use of low molecular heparin for treating osteoarthritis |
| WO2003033455A1 (en) * | 2001-10-16 | 2003-04-24 | Slil Biomedical Corporation | Oligoamine compounds and derivatives thereof for cancer therapy |
| KR100787130B1 (ko) * | 2006-03-23 | 2007-12-21 | 한국화학연구원 | 신규의 치환된 1,1-다이옥소-벤조[1,2,4]티아디아진-3-온, 이의 제조방법 및 이를 포함하는 약학적 조성물 |
| UA100120C2 (en) * | 2007-04-03 | 2012-11-26 | Анадис Фармасьютикалз, Инк. | 5,6-dihydro-1h-pyridin-2-one compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287362A (en) * | 1966-11-22 | Substituted j-oxo-j,x-dihydro-l,z,x-benzo- thiadiazine i,i-dioxides and a method for their preparation | ||
| DE1067028B (fi) * | 1959-10-15 | |||
| US3296070A (en) * | 1967-01-03 | Method for the treatment of hypertension | ||
| US3267096A (en) * | 1965-02-24 | 1966-08-16 | Miles Lab | Derivatives of 2h, 4h-benzothiadiazine 1, 1-dioxide |
| FR5571M (fi) * | 1965-12-23 | 1967-11-27 | ||
| US3892738A (en) * | 1972-03-20 | 1975-07-01 | Merck & Co Inc | 7-Thiasubstituted-1,2,4-benzothiadiazine-1,1-dioxides and their salts |
| GB8524663D0 (en) * | 1985-10-07 | 1985-11-13 | Fujisawa Pharmaceutical Co | Quinazoline derivatives |
-
1987
- 1987-11-05 US US07/116,913 patent/US4889851A/en not_active Expired - Fee Related
- 1987-11-13 DK DK597387A patent/DK597387A/da not_active Application Discontinuation
- 1987-11-18 FI FI875086A patent/FI875086A/fi not_active IP Right Cessation
- 1987-11-18 EP EP87117019A patent/EP0268990A3/en not_active Withdrawn
- 1987-11-20 KR KR1019870013086A patent/KR880006219A/ko not_active Application Discontinuation
- 1987-11-20 JP JP62294588A patent/JP2564860B2/ja not_active Expired - Lifetime
- 1987-11-20 NO NO874850A patent/NO874850L/no unknown
- 1987-11-20 CN CN198787107990A patent/CN87107990A/zh active Pending
- 1987-11-20 AU AU81465/87A patent/AU603842B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU603842B2 (en) | 1990-11-29 |
| JP2564860B2 (ja) | 1996-12-18 |
| FI875086A0 (fi) | 1987-11-18 |
| FI875086A (fi) | 1988-05-22 |
| NO874850D0 (no) | 1987-11-20 |
| DK597387D0 (da) | 1987-11-13 |
| DK597387A (da) | 1988-05-22 |
| EP0268990A2 (en) | 1988-06-01 |
| AU8146587A (en) | 1988-05-26 |
| CN87107990A (zh) | 1988-06-01 |
| US4889851A (en) | 1989-12-26 |
| EP0268990A3 (en) | 1988-08-10 |
| JPS63183572A (ja) | 1988-07-28 |
| KR880006219A (ko) | 1988-07-22 |
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