CH639660A5 - 1,5-benzothiazepin-verbindungen und verfahren zu ihrer herstellung. - Google Patents
1,5-benzothiazepin-verbindungen und verfahren zu ihrer herstellung. Download PDFInfo
- Publication number
- CH639660A5 CH639660A5 CH142479A CH142479A CH639660A5 CH 639660 A5 CH639660 A5 CH 639660A5 CH 142479 A CH142479 A CH 142479A CH 142479 A CH142479 A CH 142479A CH 639660 A5 CH639660 A5 CH 639660A5
- Authority
- CH
- Switzerland
- Prior art keywords
- cis
- dihydro
- mixture
- methyl
- melting point
- Prior art date
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- KJFRSZASZNLCDF-UHFFFAOYSA-N 1,5-benzothiazepine Chemical class S1C=CC=NC2=CC=CC=C12 KJFRSZASZNLCDF-UHFFFAOYSA-N 0.000 title description 11
- 238000000034 method Methods 0.000 title description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 36
- -1 hydroxyethyl group Chemical group 0.000 description 34
- 238000002844 melting Methods 0.000 description 34
- 230000008018 melting Effects 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 31
- 238000000921 elemental analysis Methods 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000013078 crystal Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 238000000354 decomposition reaction Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 230000000694 effects Effects 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000012280 lithium aluminium hydride Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- BHKULYKFSYZBQR-UHFFFAOYSA-M 2-ethoxycarbonyl-3-phenylprop-2-enoate Chemical compound CCOC(=O)C(C([O-])=O)=CC1=CC=CC=C1 BHKULYKFSYZBQR-UHFFFAOYSA-M 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
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- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 4
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
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- 229940126062 Compound A Drugs 0.000 description 3
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- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 239000003054 catalyst Substances 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
- 230000002496 gastric effect Effects 0.000 description 3
- 229940102396 methyl bromide Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- YGOYABDTPZVXLE-XLIONFOSSA-N (2r,3s)-3-[(4-methylpiperazin-1-yl)methyl]-2-phenyl-3,5-dihydro-2h-1,5-benzothiazepin-4-one Chemical compound C1CN(C)CCN1C[C@H]1C(=O)NC2=CC=CC=C2S[C@H]1C1=CC=CC=C1 YGOYABDTPZVXLE-XLIONFOSSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- IFASZVAJKOMRBY-UHFFFAOYSA-N 3-(hydroxymethyl)-2-phenyl-3,5-dihydro-2h-1,5-benzothiazepin-4-one Chemical compound S1C2=CC=CC=C2NC(=O)C(CO)C1C1=CC=CC=C1 IFASZVAJKOMRBY-UHFFFAOYSA-N 0.000 description 1
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- BVABFIZTUSTDDW-UHFFFAOYSA-N 5h-1,2-benzothiazepin-4-one Chemical compound S1N=CC(=O)CC2=CC=CC=C21 BVABFIZTUSTDDW-UHFFFAOYSA-N 0.000 description 1
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- 235000011090 malic acid Nutrition 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1580078A JPS5840954B2 (ja) | 1978-02-14 | 1978-02-14 | １，５↓−ベンゾチアゼピン誘導体およびその塩類 |
| JP1741478A JPS5840955B2 (ja) | 1978-02-17 | 1978-02-17 | ２，３↓−ジヒドロ↓−１，５↓−ベンゾチアゼピン誘導体 |
| JP9299878A JPS5519249A (en) | 1978-07-29 | 1978-07-29 | Optically active 1,5-benzothiazepine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH639660A5 true CH639660A5 (de) | 1983-11-30 |
Family
ID=27281143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH142479A CH639660A5 (de) | 1978-02-14 | 1979-02-14 | 1,5-benzothiazepin-verbindungen und verfahren zu ihrer herstellung. |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA1114818A (enrdf_load_stackoverflow) |
| CH (1) | CH639660A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2905637C3 (enrdf_load_stackoverflow) |
| ES (1) | ES477709A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2416890A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2017080B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477464A (en) * | 1983-02-10 | 1984-10-16 | Ciba-Geigy Corporation | Hetero-benzazepine derivatives and their pharmaceutical use |
| US4694002A (en) * | 1986-08-21 | 1987-09-15 | E. R. Squibb & Sons, Inc. | Benzothiazepine derivatives |
| JP2871811B2 (ja) * | 1990-02-28 | 1999-03-17 | サントリー株式会社 | 縮合７員環系化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3089872A (en) * | 1961-03-31 | 1963-05-14 | Olin Mathieson | Benzothiazine and benzothiazepine compounds |
-
1979
- 1979-02-12 GB GB7904882A patent/GB2017080B/en not_active Expired
- 1979-02-13 CA CA321,396A patent/CA1114818A/en not_active Expired
- 1979-02-14 ES ES477709A patent/ES477709A1/es not_active Expired
- 1979-02-14 DE DE19792905637 patent/DE2905637C3/de not_active Expired
- 1979-02-14 FR FR7903753A patent/FR2416890A1/fr active Granted
- 1979-02-14 CH CH142479A patent/CH639660A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2416890B1 (enrdf_load_stackoverflow) | 1981-11-13 |
| GB2017080B (en) | 1982-07-21 |
| DE2905637B2 (enrdf_load_stackoverflow) | 1980-07-03 |
| CA1114818A (en) | 1981-12-22 |
| DE2905637C3 (de) | 1981-05-21 |
| FR2416890A1 (fr) | 1979-09-07 |
| GB2017080A (en) | 1979-10-03 |
| DE2905637A1 (de) | 1979-08-16 |
| ES477709A1 (es) | 1979-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |