UA78743C2 - Benzothia(dia)zine derivatives and their use as ampa modulators - Google Patents
Benzothia(dia)zine derivatives and their use as ampa modulators Download PDFInfo
- Publication number
- UA78743C2 UA78743C2 UA20040706010A UA20040706010A UA78743C2 UA 78743 C2 UA78743 C2 UA 78743C2 UA 20040706010 A UA20040706010 A UA 20040706010A UA 20040706010 A UA20040706010 A UA 20040706010A UA 78743 C2 UA78743 C2 UA 78743C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- group
- compound
- branched
- linear
- Prior art date
Links
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
- 125000005843 halogen group Chemical group 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 230000009471 action Effects 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 230000006870 function Effects 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- -1 cyano, nitro, amino Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- STAGFIQRUHLMNO-UHFFFAOYSA-N (1,1-dioxo-3,4-dihydro-2h-1$l^{6},2-benzothiazin-7-yl) benzoate Chemical compound C=1C=C2CCNS(=O)(=O)C2=CC=1OC(=O)C1=CC=CC=C1 STAGFIQRUHLMNO-UHFFFAOYSA-N 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 150000002901 organomagnesium compounds Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 4
- 230000004770 neurodegeneration Effects 0.000 abstract description 4
- 208000015122 neurodegenerative disease Diseases 0.000 abstract description 4
- 208000019901 Anxiety disease Diseases 0.000 abstract description 2
- 201000011240 Frontotemporal dementia Diseases 0.000 abstract description 2
- 208000023105 Huntington disease Diseases 0.000 abstract description 2
- 208000026139 Memory disease Diseases 0.000 abstract description 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 abstract description 2
- 230000001154 acute effect Effects 0.000 abstract description 2
- 230000036506 anxiety Effects 0.000 abstract description 2
- 206010015037 epilepsy Diseases 0.000 abstract description 2
- 208000028867 ischemia Diseases 0.000 abstract description 2
- 201000000980 schizophrenia Diseases 0.000 abstract description 2
- 208000011580 syndromic disease Diseases 0.000 abstract description 2
- 208000020358 Learning disease Diseases 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 201000003723 learning disability Diseases 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- CSHJCESYHRWFCE-UHFFFAOYSA-N 2-amino-3-hydroxy-2-(5-methyl-1,2-oxazol-4-yl)propanoic acid Chemical compound CC=1ON=CC=1C(N)(CO)C(O)=O CSHJCESYHRWFCE-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004452 microanalysis Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 238000006480 benzoylation reaction Methods 0.000 description 5
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 230000000694 effects Effects 0.000 description 3
- 230000002964 excitative effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 210000000287 oocyte Anatomy 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- UQCJQCAZEDTPMI-UHFFFAOYSA-N (3-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-7-yl) benzoate Chemical compound C1=C2S(=O)(=O)NC(C)NC2=CC=C1OC(=O)C1=CC=CC=C1 UQCJQCAZEDTPMI-UHFFFAOYSA-N 0.000 description 2
- QJAFHQBDVJTCCZ-UHFFFAOYSA-N 1,1-dioxo-3,4-dihydro-2h-1$l^{6},2-benzothiazin-7-ol Chemical compound C1CNS(=O)(=O)C2=CC(O)=CC=C21 QJAFHQBDVJTCCZ-UHFFFAOYSA-N 0.000 description 2
- DSUQOTGCKDGCEZ-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonamide Chemical compound COC1=CC=C(N)C(S(N)(=O)=O)=C1 DSUQOTGCKDGCEZ-UHFFFAOYSA-N 0.000 description 2
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 2
- SRQFXWLSYFCBAT-UHFFFAOYSA-N 4-methyl-1,1-dioxo-2,3-dihydro-1$l^{6},2,4-benzothiadiazin-7-ol Chemical compound OC1=CC=C2N(C)CNS(=O)(=O)C2=C1 SRQFXWLSYFCBAT-UHFFFAOYSA-N 0.000 description 2
- 102000003678 AMPA Receptors Human genes 0.000 description 2
- 108090000078 AMPA Receptors Proteins 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 2
- 150000007658 benzothiadiazines Chemical class 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ZGSKSJWHFQPPJV-UHFFFAOYSA-N (3-cyclohexyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-7-yl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C=C1S(=O)(=O)N2)=CC=C1NC2C1CCCCC1 ZGSKSJWHFQPPJV-UHFFFAOYSA-N 0.000 description 1
- QXJAQQRUKDDWHH-UHFFFAOYSA-N (4-ethyl-1,1-dioxo-2,3-dihydro-1$l^{6},2,4-benzothiadiazin-7-yl) benzoate Chemical compound C=1C=C2N(CC)CNS(=O)(=O)C2=CC=1OC(=O)C1=CC=CC=C1 QXJAQQRUKDDWHH-UHFFFAOYSA-N 0.000 description 1
- VSRJRAZMEADIAP-UHFFFAOYSA-N (4-methyl-1,1-dioxo-2,3-dihydro-1$l^{6},2,4-benzothiadiazin-7-yl) benzoate Chemical compound C=1C=C2N(C)CNS(=O)(=O)C2=CC=1OC(=O)C1=CC=CC=C1 VSRJRAZMEADIAP-UHFFFAOYSA-N 0.000 description 1
- OMYGMZMFNVIPGR-UHFFFAOYSA-N 1-(4-hydroxy-7-methoxy-1,1-dioxo-1$l^{6},2-benzothiazin-2-yl)ethanone Chemical compound OC1=CN(C(C)=O)S(=O)(=O)C2=CC(OC)=CC=C21 OMYGMZMFNVIPGR-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- APUOZNXQGNMMKK-UHFFFAOYSA-N 3-cyclohexyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-7-ol Chemical compound N1S(=O)(=O)C2=CC(O)=CC=C2NC1C1CCCCC1 APUOZNXQGNMMKK-UHFFFAOYSA-N 0.000 description 1
- TYKLZUNULHEUNU-UHFFFAOYSA-N 3-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazin-7-ol Chemical compound C1=C(O)C=C2S(=O)(=O)NC(C)NC2=C1 TYKLZUNULHEUNU-UHFFFAOYSA-N 0.000 description 1
- DVFCOPLTCYOVKD-UHFFFAOYSA-N 4-ethyl-1,1-dioxo-2,3-dihydro-1$l^{6},2,4-benzothiadiazin-7-ol Chemical compound OC1=CC=C2N(CC)CNS(=O)(=O)C2=C1 DVFCOPLTCYOVKD-UHFFFAOYSA-N 0.000 description 1
- UCVYUTDVIPPNQT-UHFFFAOYSA-N 6-methoxy-1,1-dioxo-2-(2-oxopropyl)-1,2-benzothiazol-3-one Chemical compound COC1=CC=C2C(=O)N(CC(C)=O)S(=O)(=O)C2=C1 UCVYUTDVIPPNQT-UHFFFAOYSA-N 0.000 description 1
- UQZPSUOFYXAZEC-UHFFFAOYSA-N 7-methoxy-1,1-dioxo-2,3-dihydro-1$l^{6},2-benzothiazin-4-one Chemical compound O=C1CNS(=O)(=O)C2=CC(OC)=CC=C21 UQZPSUOFYXAZEC-UHFFFAOYSA-N 0.000 description 1
- HDYAEDZBGNRWQI-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C1CNS(=O)(=O)C2=CC(OC)=CC=C21 HDYAEDZBGNRWQI-UHFFFAOYSA-N 0.000 description 1
- XNDRKPLRZJKQOC-UHFFFAOYSA-N 7-methoxy-3-methyl-3,4-dihydro-2h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound N1C(C)NS(=O)(=O)C2=CC(OC)=CC=C21 XNDRKPLRZJKQOC-UHFFFAOYSA-N 0.000 description 1
- NQLOMTSUVHLJIC-UHFFFAOYSA-N 7-methoxy-4-methyl-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound CN1C=NS(=O)(=O)C2=CC(OC)=CC=C21 NQLOMTSUVHLJIC-UHFFFAOYSA-N 0.000 description 1
- NMODAGHLFPNMTC-UHFFFAOYSA-N 7-methoxy-4-methyl-2,3-dihydro-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound CN1CNS(=O)(=O)C2=CC(OC)=CC=C21 NMODAGHLFPNMTC-UHFFFAOYSA-N 0.000 description 1
- FOGLAAJMVBSRKU-UHFFFAOYSA-N 7-methoxy-4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical compound N1C=NS(=O)(=O)C2=CC(OC)=CC=C21 FOGLAAJMVBSRKU-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical compound Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- ZXNRTKGTQJPIJK-UHFFFAOYSA-N aniracetam Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(=O)CCC1 ZXNRTKGTQJPIJK-UHFFFAOYSA-N 0.000 description 1
- 229960000793 aniracetam Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000002461 excitatory amino acid Effects 0.000 description 1
- 239000003257 excitatory amino acid Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HVTICUPFWKNHNG-BJUDXGSMSA-N iodoethane Chemical group [11CH3]CI HVTICUPFWKNHNG-BJUDXGSMSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000008587 neuronal excitability Effects 0.000 description 1
- 230000007996 neuronal plasticity Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 239000008196 pharmacological composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000024587 synaptic transmission, glutamatergic Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- 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
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0116622A FR2833950B1 (fr) | 2001-12-21 | 2001-12-21 | Nouveaux derives de benzothiazine et de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2002/004484 WO2003053947A1 (fr) | 2001-12-21 | 2002-12-20 | Derives de benzothia(dia)zine et leur utilisation comme modulateurs ampa |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA78743C2 true UA78743C2 (en) | 2007-04-25 |
Family
ID=8870810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040706010A UA78743C2 (en) | 2001-12-21 | 2002-12-20 | Benzothia(dia)zine derivatives and their use as ampa modulators |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US7250411B2 (es) |
| EP (1) | EP1456189B1 (es) |
| JP (1) | JP2005517668A (es) |
| KR (1) | KR100606606B1 (es) |
| CN (1) | CN1606550A (es) |
| AR (1) | AR038029A1 (es) |
| AT (1) | ATE366245T1 (es) |
| AU (1) | AU2002365017B2 (es) |
| BR (1) | BR0215145A (es) |
| CA (1) | CA2471057A1 (es) |
| DE (1) | DE60221041T2 (es) |
| DK (1) | DK1456189T3 (es) |
| EA (1) | EA007271B1 (es) |
| ES (1) | ES2289182T3 (es) |
| FR (1) | FR2833950B1 (es) |
| GE (1) | GEP20063758B (es) |
| HU (1) | HUP0402584A2 (es) |
| MA (1) | MA27089A1 (es) |
| MX (1) | MXPA04005838A (es) |
| NO (1) | NO20042684L (es) |
| NZ (1) | NZ533330A (es) |
| PL (1) | PL369767A1 (es) |
| PT (1) | PT1456189E (es) |
| UA (1) | UA78743C2 (es) |
| WO (1) | WO2003053947A1 (es) |
| ZA (1) | ZA200404296B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2856065B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2856064B1 (fr) * | 2003-06-13 | 2005-08-19 | Servier Lab | Nouveaux derives de benzothiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2865474B1 (fr) * | 2004-01-26 | 2008-06-13 | Servier Lab | Nouveaux derives de benzothiazines fluorees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2877342B1 (fr) * | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2877338B1 (fr) * | 2004-11-03 | 2007-01-26 | Servier Lab | Nouveaux derives de benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2879201B1 (fr) * | 2004-12-10 | 2007-02-16 | Servier Lab | Nouveaux derives de benzothiazine et benzothiadiazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB0724625D0 (en) * | 2007-12-18 | 2008-01-30 | Glaxo Group Ltd | Novel compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07505411A (ja) * | 1992-04-15 | 1995-06-15 | ローン−プーラン・ロレ・ソシエテ・アノニム | ３，４−ジヒドロ−１ｈ−１，２，４−ベンゾチアジアジン−１，１−ジオキシド−２−カルボン酸誘導体，それらの製造およびそれらを含有する医学的生成物 |
| WO1998012185A1 (en) * | 1996-09-17 | 1998-03-26 | The Regents Of The University Of California | Benzothiadiazide derivatives and their use as allosteric up-modulators of the ampa receptor |
| PL342843A1 (en) * | 1998-02-18 | 2001-07-16 | Neurosearch As | Novel compounds and their use as positive ampa receptor modulators |
| FR2801587B1 (fr) * | 1999-11-30 | 2002-01-11 | Adir | Nouveaux derives de benzothiadiazines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2001
- 2001-12-21 FR FR0116622A patent/FR2833950B1/fr not_active Expired - Fee Related
-
2002
- 2002-12-18 AR ARP020104933A patent/AR038029A1/es unknown
- 2002-12-20 GE GE5644A patent/GEP20063758B/en unknown
- 2002-12-20 MX MXPA04005838A patent/MXPA04005838A/es active IP Right Grant
- 2002-12-20 CA CA002471057A patent/CA2471057A1/fr not_active Abandoned
- 2002-12-20 DE DE60221041T patent/DE60221041T2/de not_active Expired - Fee Related
- 2002-12-20 PL PL02369767A patent/PL369767A1/xx not_active Application Discontinuation
- 2002-12-20 EP EP02805407A patent/EP1456189B1/fr not_active Expired - Lifetime
- 2002-12-20 AT AT02805407T patent/ATE366245T1/de not_active IP Right Cessation
- 2002-12-20 ES ES02805407T patent/ES2289182T3/es not_active Expired - Lifetime
- 2002-12-20 NZ NZ533330A patent/NZ533330A/en unknown
- 2002-12-20 KR KR1020047009303A patent/KR100606606B1/ko not_active IP Right Cessation
- 2002-12-20 WO PCT/FR2002/004484 patent/WO2003053947A1/fr active IP Right Grant
- 2002-12-20 CN CNA028258142A patent/CN1606550A/zh active Pending
- 2002-12-20 PT PT02805407T patent/PT1456189E/pt unknown
- 2002-12-20 DK DK02805407T patent/DK1456189T3/da active
- 2002-12-20 AU AU2002365017A patent/AU2002365017B2/en not_active Ceased
- 2002-12-20 EA EA200400756A patent/EA007271B1/ru not_active IP Right Cessation
- 2002-12-20 US US10/499,082 patent/US7250411B2/en not_active Expired - Fee Related
- 2002-12-20 UA UA20040706010A patent/UA78743C2/uk unknown
- 2002-12-20 BR BR0215145-6A patent/BR0215145A/pt not_active IP Right Cessation
- 2002-12-20 JP JP2003554663A patent/JP2005517668A/ja active Pending
- 2002-12-20 HU HU0402584A patent/HUP0402584A2/hu unknown
-
2004
- 2004-06-01 ZA ZA200404296A patent/ZA200404296B/en unknown
- 2004-06-04 MA MA27718A patent/MA27089A1/fr unknown
- 2004-06-25 NO NO20042684A patent/NO20042684L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60221041T2 (de) | 2008-04-10 |
| FR2833950B1 (fr) | 2005-12-16 |
| US7250411B2 (en) | 2007-07-31 |
| GEP20063758B (en) | 2006-02-27 |
| AR038029A1 (es) | 2004-12-22 |
| CA2471057A1 (fr) | 2003-07-03 |
| AU2002365017B2 (en) | 2007-12-13 |
| EP1456189B1 (fr) | 2007-07-04 |
| DE60221041D1 (de) | 2007-08-16 |
| ZA200404296B (en) | 2005-06-01 |
| ATE366245T1 (de) | 2007-07-15 |
| DK1456189T3 (da) | 2007-11-05 |
| JP2005517668A (ja) | 2005-06-16 |
| FR2833950A1 (fr) | 2003-06-27 |
| EA007271B1 (ru) | 2006-08-25 |
| EA200400756A1 (ru) | 2004-10-28 |
| BR0215145A (pt) | 2004-10-19 |
| PT1456189E (pt) | 2007-09-20 |
| CN1606550A (zh) | 2005-04-13 |
| NO20042684L (no) | 2004-06-25 |
| EP1456189A1 (fr) | 2004-09-15 |
| PL369767A1 (en) | 2005-05-02 |
| WO2003053947A1 (fr) | 2003-07-03 |
| KR100606606B1 (ko) | 2006-08-01 |
| MA27089A1 (fr) | 2004-12-20 |
| MXPA04005838A (es) | 2004-09-10 |
| ES2289182T3 (es) | 2008-02-01 |
| KR20040065276A (ko) | 2004-07-21 |
| NZ533330A (en) | 2006-05-26 |
| HUP0402584A2 (hu) | 2005-04-28 |
| US20050014744A1 (en) | 2005-01-20 |
| AU2002365017A1 (en) | 2003-07-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2703051A1 (fr) | Nouvelles pyridothiadiazines, leurs procédés de préparation, et les compositions pharmaceutiques qui les contiennent. | |
| KR100818431B1 (ko) | 벤조티아디아진 화합물, 이를 제조하는 방법 및 이를함유하는 약제 조성물 | |
| UA78743C2 (en) | Benzothia(dia)zine derivatives and their use as ampa modulators | |
| UA77737C2 (en) | Benzothiazine and benzothiadizine derivatives, a process for preparation thereof and pharmaceutical composition containing them | |
| AU2004236005B2 (en) | Thiadiazine derivatives and use thereof as positive AMPA receptor modulators | |
| AU2009202704B2 (en) | New cycloalkylated benzothiadiazines, a process for their preparation and pharmaceutical compositions containing them | |
| KR100586683B1 (ko) | 벤조티아진 및 벤조티아디아진 화합물, 이들의 제조방법및 이들을 함유하는 약제 조성물 | |
| AU2005200311A1 (en) | New fluorinated benzothiadiazone compounds, a process for their preparation and pharmaceutical compositions containing them | |
| EA004682B1 (ru) | Бензотиадиазиновые соединения, способ их получения и содержащие их фармацевтические композиции | |
| UA78742C2 (en) | Benzothiazine and benzothiadiazine derivatives, method for preparing same and pharmaceutical composition containing thereof | |
| UA82183C2 (uk) | Похідні бензотіазину і бензотіадіазину, спосіб їх одержання і фармацевтична композиція, яка їх містить | |
| NZ543359A (en) | Benzothiadiazine compounds, a process for their preparation and pharmaceutical compositions containing them | |
| UA82182C2 (uk) | Похідні бензотіазину і бензотіадіазину, спосіб їх одержання і фармацевтична композиція, яка їх містить |