JP2005508352A - 新規ベンゾチアジン誘導体、その製造方法及びその使用方法 - Google Patents
新規ベンゾチアジン誘導体、その製造方法及びその使用方法 Download PDFInfo
- Publication number
- JP2005508352A JP2005508352A JP2003534405A JP2003534405A JP2005508352A JP 2005508352 A JP2005508352 A JP 2005508352A JP 2003534405 A JP2003534405 A JP 2003534405A JP 2003534405 A JP2003534405 A JP 2003534405A JP 2005508352 A JP2005508352 A JP 2005508352A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- sulfonyl
- benzo
- thiazine
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical class C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- -1 hydroxy, amino Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000002950 monocyclic group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 125000002837 carbocyclic group Chemical group 0.000 claims description 19
- 208000035475 disorder Diseases 0.000 claims description 19
- 201000006417 multiple sclerosis Diseases 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- 108090000078 AMPA Receptors Proteins 0.000 claims description 10
- 102000003678 AMPA Receptors Human genes 0.000 claims description 10
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- KQAGZLQCEURCKJ-UHFFFAOYSA-N 3-cyclopentyl-6-methyl-7-(4-methylpiperazin-1-yl)sulfonyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C1CN(C)CCN1S(=O)(=O)C(C(=C1)C)=CC2=C1CC(C1CCCC1)NS2(=O)=O KQAGZLQCEURCKJ-UHFFFAOYSA-N 0.000 claims description 8
- 208000026139 Memory disease Diseases 0.000 claims description 8
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
- 230000006735 deficit Effects 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 125000003003 spiro group Chemical group 0.000 claims description 7
- MESFXNGUDNODTJ-UHFFFAOYSA-N 2h-thiazine 1,1-dioxide Chemical compound O=S1(=O)NC=CC=C1 MESFXNGUDNODTJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 206010003805 Autism Diseases 0.000 claims description 4
- 208000020706 Autistic disease Diseases 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- 208000020358 Learning disease Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 4
- 230000000747 cardiac effect Effects 0.000 claims description 4
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- 201000003723 learning disability Diseases 0.000 claims description 4
- 206010027175 memory impairment Diseases 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 208000020016 psychiatric disease Diseases 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 3
- FEKTZBLJGQYRGO-UHFFFAOYSA-N 1-[(3-cyclopentyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2-benzothiazin-7-yl)sulfonyl]-n,n-dimethylpiperidin-4-amine Chemical compound C1CC(N(C)C)CCN1S(=O)(=O)C1=CC=C(CC(NS2(=O)=O)C3CCCC3)C2=C1 FEKTZBLJGQYRGO-UHFFFAOYSA-N 0.000 claims description 3
- NXNVXQVVROGKLQ-UHFFFAOYSA-N 1-[(3-cyclopentyl-6-methyl-1,1-dioxo-3,4-dihydro-2h-1$l^{6},2-benzothiazin-7-yl)sulfonyl]piperidin-4-ol Chemical compound CC1=CC=2CC(C3CCCC3)NS(=O)(=O)C=2C=C1S(=O)(=O)N1CCC(O)CC1 NXNVXQVVROGKLQ-UHFFFAOYSA-N 0.000 claims description 3
- OMTIEEKLZYEANQ-UHFFFAOYSA-N 3-cyclohexyl-7-(4-methylpiperazin-1-yl)sulfonyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(CC(NS2(=O)=O)C3CCCCC3)C2=C1 OMTIEEKLZYEANQ-UHFFFAOYSA-N 0.000 claims description 3
- IABGLVGRFSTTHD-UHFFFAOYSA-N 3-cyclohexyl-7-piperidin-1-ylsulfonyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C=1C=C2CC(C3CCCCC3)NS(=O)(=O)C2=CC=1S(=O)(=O)N1CCCCC1 IABGLVGRFSTTHD-UHFFFAOYSA-N 0.000 claims description 3
- HPONCVDFKJUAHI-UHFFFAOYSA-N 3-cyclopentyl-6-methyl-7-morpholin-4-ylsulfonyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound CC1=CC=2CC(C3CCCC3)NS(=O)(=O)C=2C=C1S(=O)(=O)N1CCOCC1 HPONCVDFKJUAHI-UHFFFAOYSA-N 0.000 claims description 3
- IUNMOUYVVPFXOJ-UHFFFAOYSA-N 3-cyclopentyl-6-methyl-7-piperidin-1-ylsulfonyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound CC1=CC=2CC(C3CCCC3)NS(=O)(=O)C=2C=C1S(=O)(=O)N1CCCCC1 IUNMOUYVVPFXOJ-UHFFFAOYSA-N 0.000 claims description 3
- QZBQVXXESPXFPZ-UHFFFAOYSA-N 3-cyclopentyl-7-(4-methylpiperazin-1-yl)sulfonyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(CC(NS2(=O)=O)C3CCCC3)C2=C1 QZBQVXXESPXFPZ-UHFFFAOYSA-N 0.000 claims description 3
- OFFUHSXGWXMEBR-UHFFFAOYSA-N 3-cyclopentyl-7-morpholin-4-ylsulfonyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C=1C=C2CC(C3CCCC3)NS(=O)(=O)C2=CC=1S(=O)(=O)N1CCOCC1 OFFUHSXGWXMEBR-UHFFFAOYSA-N 0.000 claims description 3
- DKONITGDYUPUBA-UHFFFAOYSA-N 3-cyclopentyl-7-piperidin-1-ylsulfonyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C=1C=C2CC(C3CCCC3)NS(=O)(=O)C2=CC=1S(=O)(=O)N1CCCCC1 DKONITGDYUPUBA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000000116 mitigating effect Effects 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 50
- 102000018899 Glutamate Receptors Human genes 0.000 abstract description 3
- 108010027915 Glutamate Receptors Proteins 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract description 3
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000004044 response Effects 0.000 description 20
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- 238000007429 general method Methods 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
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- 229960003692 gamma aminobutyric acid Drugs 0.000 description 7
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- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 6
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- DAAXYQZSKBPJOX-FQEVSTJZSA-N (2S)-2-amino-3-[4-[5-[3-(4-hydroxyphenyl)-4-methoxyphenyl]-1,2,4-oxadiazol-3-yl]phenyl]propanoic acid Chemical compound COC1=C(C=C(C=C1)C2=NC(=NO2)C3=CC=C(C=C3)C[C@@H](C(=O)O)N)C4=CC=C(C=C4)O DAAXYQZSKBPJOX-FQEVSTJZSA-N 0.000 description 5
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- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 4
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- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 4
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- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 4
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- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BZWKPZBXAMTXNQ-UHFFFAOYSA-N sulfurocyanidic acid Chemical compound OS(=O)(=O)C#N BZWKPZBXAMTXNQ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 1
- 229950010357 tetrodotoxin Drugs 0.000 description 1
- CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Substances ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical compound C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 description 1
- 229930004006 tropane Natural products 0.000 description 1
- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P25/24—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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Gynecology & Obstetrics (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200101498 | 2001-10-10 | ||
| PCT/DK2002/000654 WO2003031422A1 (en) | 2001-10-10 | 2002-10-02 | Novel benzothiazine derivatives, their preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005508352A true JP2005508352A (ja) | 2005-03-31 |
| JP2005508352A5 JP2005508352A5 (https=) | 2006-01-05 |
Family
ID=8160760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003534405A Withdrawn JP2005508352A (ja) | 2001-10-10 | 2002-10-02 | 新規ベンゾチアジン誘導体、その製造方法及びその使用方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7199118B2 (https=) |
| EP (1) | EP1436270A1 (https=) |
| JP (1) | JP2005508352A (https=) |
| CN (1) | CN1275951C (https=) |
| CA (1) | CA2458388A1 (https=) |
| MX (1) | MXPA04003297A (https=) |
| NZ (1) | NZ531511A (https=) |
| WO (1) | WO2003031422A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3547859B2 (ja) * | 1995-07-14 | 2004-07-28 | 愛知機械工業株式会社 | 2方向差動クラッチ |
| 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. |
| 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 |
| FR2933698A1 (fr) | 2008-07-09 | 2010-01-15 | Servier Lab | Nouveaux derives de benzothiadiazines cycloalkylees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2955107B1 (fr) * | 2010-01-08 | 2012-03-02 | Servier Lab | Nouveaux derives thiochromanes, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US9150591B2 (en) | 2010-08-10 | 2015-10-06 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| CR20220160A (es) | 2019-09-16 | 2022-06-16 | Takeda Pharmaceuticals Co | Derivados de piridazin-3(2h)-ona fusionados con azol |
| CN111393385B (zh) * | 2020-04-15 | 2022-01-18 | 华南理工大学 | 一种苯并噻嗪甲醛衍生物的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113075A (en) * | 1960-10-17 | 1963-12-03 | Merck & Co Inc | Heterocyclic compounds |
| DE1302858B (https=) * | 1962-09-21 | 1972-05-04 | ||
| FR1552763A (https=) * | 1963-11-08 | 1969-01-10 | ||
| FR3136M (fr) * | 1963-11-08 | 1965-02-15 | Merck & Co Inc | Nouveaux médicaments diurétiques. |
| CN1293665A (zh) * | 1998-02-18 | 2001-05-02 | 神经研究公司 | 新化合物及其用作阳性ampa受体调节剂 |
| DE10004572A1 (de) * | 2000-02-02 | 2001-08-09 | Boehringer Ingelheim Pharma | Neue positive allosterische AMPA-Rezeptor Modulatoren (PAARM), Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
-
2002
- 2002-10-02 MX MXPA04003297A patent/MXPA04003297A/es unknown
- 2002-10-02 CA CA002458388A patent/CA2458388A1/en not_active Abandoned
- 2002-10-02 EP EP02800544A patent/EP1436270A1/en not_active Withdrawn
- 2002-10-02 WO PCT/DK2002/000654 patent/WO2003031422A1/en not_active Ceased
- 2002-10-02 NZ NZ531511A patent/NZ531511A/en unknown
- 2002-10-02 US US10/489,640 patent/US7199118B2/en not_active Expired - Fee Related
- 2002-10-02 CN CNB028195248A patent/CN1275951C/zh not_active Expired - Fee Related
- 2002-10-02 JP JP2003534405A patent/JP2005508352A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003031422A1 (en) | 2003-04-17 |
| EP1436270A1 (en) | 2004-07-14 |
| CA2458388A1 (en) | 2003-04-17 |
| CN1564817A (zh) | 2005-01-12 |
| CN1275951C (zh) | 2006-09-20 |
| MXPA04003297A (es) | 2004-07-23 |
| US20040242571A1 (en) | 2004-12-02 |
| US7199118B2 (en) | 2007-04-03 |
| NZ531511A (en) | 2006-01-27 |
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