JPS60116677A - ベンゾチアゼピン誘導体の製造法 - Google Patents
ベンゾチアゼピン誘導体の製造法Info
- Publication number
- JPS60116677A JPS60116677A JP22657083A JP22657083A JPS60116677A JP S60116677 A JPS60116677 A JP S60116677A JP 22657083 A JP22657083 A JP 22657083A JP 22657083 A JP22657083 A JP 22657083A JP S60116677 A JPS60116677 A JP S60116677A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- reaction
- formula
- dimethylaminoethyl
- aminothiophenol
- 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.)
- Granted
Links
- 150000007657 benzothiazepines Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 8
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 6
- 239000000010 aprotic solvent Substances 0.000 abstract description 5
- -1 counterdepressant Substances 0.000 abstract description 5
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract description 5
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 239000003218 coronary vasodilator agent Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 229940125725 tranquilizer Drugs 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- 239000012345 acetylating agent Substances 0.000 description 3
- 229940085242 benzothiazepine derivative selective calcium channel blockers with direct cardiac effects Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- AOPNPZIOVIPWMF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-oxopropanoic acid Chemical compound COC1=CC=C(CC(=O)C(O)=O)C=C1 AOPNPZIOVIPWMF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000003431 oxalo group Chemical group 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910020676 Co—N Inorganic materials 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WJGAPUXHSQQWQF-UHFFFAOYSA-N acetic acid;hydrochloride Chemical compound Cl.CC(O)=O WJGAPUXHSQQWQF-UHFFFAOYSA-N 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22657083A JPS60116677A (ja) | 1983-11-30 | 1983-11-30 | ベンゾチアゼピン誘導体の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22657083A JPS60116677A (ja) | 1983-11-30 | 1983-11-30 | ベンゾチアゼピン誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60116677A true JPS60116677A (ja) | 1985-06-24 |
| JPH0527629B2 JPH0527629B2 (enrdf_load_stackoverflow) | 1993-04-21 |
Family
ID=16847232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22657083A Granted JPS60116677A (ja) | 1983-11-30 | 1983-11-30 | ベンゾチアゼピン誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60116677A (enrdf_load_stackoverflow) |
-
1983
- 1983-11-30 JP JP22657083A patent/JPS60116677A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0527629B2 (enrdf_load_stackoverflow) | 1993-04-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0651718B2 (ja) | アザステロイドに１，２二重結合を導入する方法 | |
| EP0478558A1 (en) | An improved process for the preparation of substituted isoflavone derivatives. | |
| JPH01104095A (ja) | アンドロスタ−１，４−ジエン−３，１７−ジオンのメチレン誘導体の製造方法 | |
| HU206200B (en) | Process for producing compounds comprising condensed quinoline ring system | |
| IE46769B1 (en) | Process for the production of urea derivatives | |
| JPH02215750A (ja) | ２，６−ジクロロフェニルアミノベンゼン酢酸誘導体及びジフェニルアミン誘導体の製造方法。 | |
| JPS60116677A (ja) | ベンゾチアゼピン誘導体の製造法 | |
| CS253742B2 (en) | Process for preparing beta-carbolines | |
| JPS5940840B2 (ja) | アンドロスタン系の新規なジエン誘導体の製造法 | |
| US3478028A (en) | 4-substituted-1-hydroxylaminophthalazines | |
| HU183495B (en) | Process for producing 17-alpha-hydroxy- and 17a-alpha-hydroxy-d-homo-ethiocarboxylic acids | |
| US4614824A (en) | Novel apovincaminic acid derivatives | |
| CA1125762A (en) | Dihydronicotinic acid derivatives and process for the preparation thereof | |
| JPH01131194A (ja) | プレグナノ［１７α，１６α−ｄ］オキサゾリン誘導体の製造法 | |
| HU192999B (en) | Process for producing tricyclie thiadiazinon derivatives | |
| KR0133056B1 (ko) | 1, 5-벤조티아제핀 유도체의 제조방법 | |
| JPS603383B2 (ja) | ６−クロロ−α−メチル−カルバゾ−ル−２−酢酸の製造方法 | |
| JPS6078973A (ja) | １，５−ベンゾチアゼピン誘導体の製法 | |
| JPS5916878A (ja) | ２，４−ジヒドロキシ−３−アセチルキノリン類の製造方法 | |
| SU328572A1 (ru) | СПОСОБ ПОЛУЧЕНИЯ АМИДОВ ИЛИ ПЕПТИДОВ N-АЦИЛ-а-АМИНОКИСЛОТЫ | |
| CA2056129C (en) | Process for preparing 1,5-benzothiazepine derivative | |
| JPS5888400A (ja) | 新規コレスタン誘導体 | |
| JPS6345675B2 (enrdf_load_stackoverflow) | ||
| JPS60246384A (ja) | クロモン−８−カルポキサミド誘導体 | |
| JPH05202013A (ja) | １，５−ベンゾチアゼピン誘導体の製法 |