JPS6043345B2 - フェノチアジン誘導体及びそれらの製造方法 - Google Patents
フェノチアジン誘導体及びそれらの製造方法Info
- Publication number
- JPS6043345B2 JPS6043345B2 JP55044086A JP4408680A JPS6043345B2 JP S6043345 B2 JPS6043345 B2 JP S6043345B2 JP 55044086 A JP55044086 A JP 55044086A JP 4408680 A JP4408680 A JP 4408680A JP S6043345 B2 JPS6043345 B2 JP S6043345B2
- Authority
- JP
- Japan
- Prior art keywords
- tables
- formulas
- formula
- phenothiazine
- chemical formulas
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 25
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 title claims description 5
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 17
- 150000002990 phenothiazines Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 229950000688 phenothiazine Drugs 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- -1 ethanesulfonate Chemical class 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 229960002690 fluphenazine Drugs 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001263 acyl chlorides Chemical class 0.000 description 7
- OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- VIQCGTZFEYDQMR-UHFFFAOYSA-N fluphenazine decanoate Chemical compound C1CN(CCOC(=O)CCCCCCCCC)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 VIQCGTZFEYDQMR-UHFFFAOYSA-N 0.000 description 4
- 229960001374 fluphenazine decanoate Drugs 0.000 description 4
- 239000008159 sesame oil Substances 0.000 description 4
- 235000011803 sesame oil Nutrition 0.000 description 4
- KTZYBQFUJLPFMF-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)-2-methylpropanoyl chloride Chemical compound CC1=CC(C)=CC(OC(C)(C)C(Cl)=O)=C1 KTZYBQFUJLPFMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- OBTBTAXSGBQRGI-UHFFFAOYSA-N 2-(2,6-dichlorophenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=C(Cl)C=CC=C1Cl OBTBTAXSGBQRGI-UHFFFAOYSA-N 0.000 description 2
- SXWGTMNDGSAUON-UHFFFAOYSA-N 2-(3,5-dimethylphenoxy)-2-methylpropanoic acid Chemical class CC1=CC(C)=CC(OC(C)(C)C(O)=O)=C1 SXWGTMNDGSAUON-UHFFFAOYSA-N 0.000 description 2
- NAABUGJBFBVHMI-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)-2-methylpropanoyl chloride Chemical compound CC(C)(C)C1=CC=C(OC(C)(C)C(Cl)=O)C=C1 NAABUGJBFBVHMI-UHFFFAOYSA-N 0.000 description 2
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
- 229960004046 apomorphine Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000006742 locomotor activity Effects 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
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ZAWKYPLLOTZOCX-UHFFFAOYSA-N 2,3-dimethyl-2-naphthalen-1-yloxybutanoic acid Chemical compound C1=CC=C2C(OC(C)(C(C)C)C(O)=O)=CC=CC2=C1 ZAWKYPLLOTZOCX-UHFFFAOYSA-N 0.000 description 1
- WYFSUSLTCPKAEY-UHFFFAOYSA-N 2,3-dimethyl-2-phenoxybutanoic acid Chemical compound CC(C)C(C)(C(O)=O)OC1=CC=CC=C1 WYFSUSLTCPKAEY-UHFFFAOYSA-N 0.000 description 1
- IHAQERCVADRQLM-UHFFFAOYSA-N 2-(2,3-dichlorophenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC(Cl)=C1Cl IHAQERCVADRQLM-UHFFFAOYSA-N 0.000 description 1
- JXYZSUYTZSGVQE-UHFFFAOYSA-N 2-(2,3-dichlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=CC(Cl)=C1Cl JXYZSUYTZSGVQE-UHFFFAOYSA-N 0.000 description 1
- UHNQBMHNYDFJKX-UHFFFAOYSA-N 2-(2,5-dimethylphenoxy)-2-methylpropanoic acid Chemical compound CC1=CC=C(C)C(OC(C)(C)C(O)=O)=C1 UHNQBMHNYDFJKX-UHFFFAOYSA-N 0.000 description 1
- NKOLBXHNFWSMHI-UHFFFAOYSA-N 2-(2,5-dimethylphenoxy)-2-methylpropanoyl chloride Chemical compound CC1=CC=C(C)C(OC(C)(C)C(Cl)=O)=C1 NKOLBXHNFWSMHI-UHFFFAOYSA-N 0.000 description 1
- KMJGWRUNLSTING-UHFFFAOYSA-N 2-(2,6-dichlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=C(Cl)C=CC=C1Cl KMJGWRUNLSTING-UHFFFAOYSA-N 0.000 description 1
- KPYUGMQZJXMMOM-UHFFFAOYSA-N 2-(2,6-dimethylphenoxy)-2-methylpropanoic acid Chemical compound CC1=CC=CC(C)=C1OC(C)(C)C(O)=O KPYUGMQZJXMMOM-UHFFFAOYSA-N 0.000 description 1
- UXDMCAHPVYEHKH-UHFFFAOYSA-N 2-(2,6-dimethylphenoxy)-2-methylpropanoyl chloride Chemical compound CC1=CC=CC(C)=C1OC(C)(C)C(Cl)=O UXDMCAHPVYEHKH-UHFFFAOYSA-N 0.000 description 1
- OODRWLGKUBMFLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OODRWLGKUBMFLZ-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N 2-(6-methoxy-2-naphthalenyl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- UODROGXCIVAQDJ-UHFFFAOYSA-N 2-(6-methoxynaphthalen-2-yl)propanoyl chloride Chemical compound C1=C(C(C)C(Cl)=O)C=CC2=CC(OC)=CC=C21 UODROGXCIVAQDJ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RZDVBMXTYNFTJD-UHFFFAOYSA-N 2-methyl-2-(2,4,6-trimethylphenoxy)propanoic acid Chemical compound CC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 RZDVBMXTYNFTJD-UHFFFAOYSA-N 0.000 description 1
- ZGQMZVWPCVHENS-UHFFFAOYSA-N 2-methyl-2-(4-nitrophenoxy)propanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C([N+]([O-])=O)C=C1 ZGQMZVWPCVHENS-UHFFFAOYSA-N 0.000 description 1
- FEQKLTOBQAFPHM-UHFFFAOYSA-N 2-methyl-2-(4-nitrophenoxy)propanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C([N+]([O-])=O)C=C1 FEQKLTOBQAFPHM-UHFFFAOYSA-N 0.000 description 1
- DZCPSVQCXLAEKZ-UHFFFAOYSA-N 2-methyl-2-naphthalen-1-yloxypropanoyl chloride Chemical compound C1=CC=C2C(OC(C)(C)C(Cl)=O)=CC=CC2=C1 DZCPSVQCXLAEKZ-UHFFFAOYSA-N 0.000 description 1
- RVAWSQIHNATWNO-UHFFFAOYSA-N 2-methyl-2-naphthalen-2-yloxypropanoic acid Chemical compound C1=CC=CC2=CC(OC(C)(C)C(O)=O)=CC=C21 RVAWSQIHNATWNO-UHFFFAOYSA-N 0.000 description 1
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 1
- WWIJGHHDQFJHQW-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=CC=C1 WWIJGHHDQFJHQW-UHFFFAOYSA-N 0.000 description 1
- QORUPYXZMNXIAS-UHFFFAOYSA-N 3,3-dichloro-2-methyl-2-phenoxypropanoic acid Chemical compound ClC(Cl)C(C(O)=O)(C)OC1=CC=CC=C1 QORUPYXZMNXIAS-UHFFFAOYSA-N 0.000 description 1
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 1
- SCWBSTVOWDDYHH-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol;4-aminophenol Chemical compound NC1=CC=C(O)C=C1.NC1=CC(Cl)=C(O)C(Cl)=C1 SCWBSTVOWDDYHH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- MEPKRIDFXPYSMP-UHFFFAOYSA-N CCC(C(=O)O)(C)OC1=CC=CC2=CC=CC=C12 Chemical compound CCC(C(=O)O)(C)OC1=CC=CC2=CC=CC=C12 MEPKRIDFXPYSMP-UHFFFAOYSA-N 0.000 description 1
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- 208000009132 Catalepsy Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
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- 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
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- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FRXPDEZCWCPLIH-UHFFFAOYSA-N naphthalen-1-yl propanoate Chemical class C1=CC=C2C(OC(=O)CC)=CC=CC2=C1 FRXPDEZCWCPLIH-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000001508 neuroinhibitory effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
- C07D279/24—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom
- C07D279/28—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom with hydrocarbon radicals, substituted by amino radicals, attached to the ring nitrogen atom with other substituents attached to the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P25/18—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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1422 | 1979-04-06 | ||
| HU79GO1442A HU179190B (en) | 1979-04-06 | 1979-04-06 | Process for preparing new phenthiazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55153776A JPS55153776A (en) | 1980-11-29 |
| JPS6043345B2 true JPS6043345B2 (ja) | 1985-09-27 |
Family
ID=10996889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55044086A Expired JPS6043345B2 (ja) | 1979-04-06 | 1980-04-05 | フェノチアジン誘導体及びそれらの製造方法 |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS6043345B2 (cs) |
| AT (1) | AT375355B (cs) |
| BE (1) | BE882535A (cs) |
| CA (1) | CA1128940A (cs) |
| CH (1) | CH643843A5 (cs) |
| CS (1) | CS214704B2 (cs) |
| DD (1) | DD150060A5 (cs) |
| DE (1) | DE3013502C2 (cs) |
| ES (1) | ES490315A0 (cs) |
| FR (1) | FR2453164A1 (cs) |
| GB (1) | GB2047694B (cs) |
| HU (1) | HU179190B (cs) |
| IT (1) | IT1148812B (cs) |
| PL (1) | PL127329B1 (cs) |
| SU (1) | SU925250A3 (cs) |
| YU (1) | YU42663B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0568560U (ja) * | 1991-11-05 | 1993-09-17 | 理照 大島 | 握力強化用具 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4471116A (en) * | 1982-07-28 | 1984-09-11 | Hoffmann-La Roche Inc. | Substituted (10H-phenothiazin-10-L)-propyl-1-piperazines |
| JP3932785B2 (ja) | 1999-08-25 | 2007-06-20 | 株式会社村田製作所 | 圧電体の製造方法 |
| RU2167157C1 (ru) * | 2000-02-11 | 2001-05-20 | Государственный научный центр РФ "НИОПИК" | Способ получения 2-трифторметил-10-(3-хлорпропил)-фенотиазина |
| US20060111346A1 (en) * | 2004-11-23 | 2006-05-25 | Fazix Corporation. | Methods of modulating high-density lipoprotein cholesterol levels and pharmaceutical formulations for the same |
| PL444423A1 (pl) | 2023-04-15 | 2024-10-21 | Ml System Spółka Akcyjna | Sposób wytwarzania laminarnej warstwowej płyty fotowoltaicznej i laminarna warstwowa płyta fotowoltaiczna wytworzona tym sposobem |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL277672A (cs) * | 1961-04-26 |
-
1979
- 1979-04-06 HU HU79GO1442A patent/HU179190B/hu not_active IP Right Cessation
-
1980
- 1980-03-31 BE BE1/9766A patent/BE882535A/fr not_active IP Right Cessation
- 1980-03-31 GB GB8010794A patent/GB2047694B/en not_active Expired
- 1980-04-01 FR FR8007313A patent/FR2453164A1/fr active Granted
- 1980-04-03 CH CH266180A patent/CH643843A5/de not_active IP Right Cessation
- 1980-04-03 DD DD80220206A patent/DD150060A5/de not_active IP Right Cessation
- 1980-04-03 CA CA349,181A patent/CA1128940A/en not_active Expired
- 1980-04-03 AT AT0184080A patent/AT375355B/de not_active IP Right Cessation
- 1980-04-04 CS CS802359A patent/CS214704B2/cs unknown
- 1980-04-04 YU YU933/80A patent/YU42663B/xx unknown
- 1980-04-04 IT IT21186/80A patent/IT1148812B/it active
- 1980-04-04 PL PL1980223267A patent/PL127329B1/pl unknown
- 1980-04-04 SU SU802903447A patent/SU925250A3/ru active
- 1980-04-05 JP JP55044086A patent/JPS6043345B2/ja not_active Expired
- 1980-04-07 ES ES490315A patent/ES490315A0/es active Granted
- 1980-04-08 DE DE3013502A patent/DE3013502C2/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0568560U (ja) * | 1991-11-05 | 1993-09-17 | 理照 大島 | 握力強化用具 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8103077A1 (es) | 1981-02-16 |
| FR2453164A1 (fr) | 1980-10-31 |
| CA1128940A (en) | 1982-08-03 |
| GB2047694B (en) | 1983-02-02 |
| AT375355B (de) | 1984-07-25 |
| DE3013502A1 (de) | 1980-10-16 |
| CH643843A5 (de) | 1984-06-29 |
| JPS55153776A (en) | 1980-11-29 |
| GB2047694A (en) | 1980-12-03 |
| YU42663B (en) | 1988-10-31 |
| DD150060A5 (de) | 1981-08-12 |
| SU925250A3 (ru) | 1982-04-30 |
| ATA184080A (de) | 1983-12-15 |
| IT1148812B (it) | 1986-12-03 |
| YU93380A (en) | 1983-01-21 |
| IT8021186A0 (it) | 1980-04-04 |
| DE3013502C2 (de) | 1985-02-07 |
| ES490315A0 (es) | 1981-02-16 |
| CS214704B2 (en) | 1982-05-28 |
| PL223267A1 (cs) | 1981-01-30 |
| HU179190B (en) | 1982-09-28 |
| FR2453164B1 (cs) | 1983-04-15 |
| BE882535A (fr) | 1980-09-30 |
| PL127329B1 (en) | 1983-10-31 |
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