CS202007B2 - Method of producing aminoderivatives of 4-hydroxy-1,2-benzoisothiazole - Google Patents
Method of producing aminoderivatives of 4-hydroxy-1,2-benzoisothiazole Download PDFInfo
- Publication number
- CS202007B2 CS202007B2 CS78734A CS73478A CS202007B2 CS 202007 B2 CS202007 B2 CS 202007B2 CS 78734 A CS78734 A CS 78734A CS 73478 A CS73478 A CS 73478A CS 202007 B2 CS202007 B2 CS 202007B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- benzisothiazole
- hydroxy
- yloxy
- formula
- benzisothiazol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- VLSJPIWHDLNJOP-UHFFFAOYSA-N 1,2-benzothiazol-4-ol Chemical class OC1=CC=CC2=C1C=NS2 VLSJPIWHDLNJOP-UHFFFAOYSA-N 0.000 title description 8
- -1 their preparation Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 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 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- TYDIKDRXPYYLES-UHFFFAOYSA-N 1-(1,2-benzothiazol-4-yloxy)-3-(butan-2-ylamino)propan-2-ol Chemical compound CCC(C)NCC(O)COC1=CC=CC2=C1C=NS2 TYDIKDRXPYYLES-UHFFFAOYSA-N 0.000 claims description 3
- PQMLTCGZCDCYAH-UHFFFAOYSA-N 1-(1,2-benzothiazol-4-yloxy)-3-chloropropan-2-ol Chemical compound ClCC(O)COC1=CC=CC2=C1C=NS2 PQMLTCGZCDCYAH-UHFFFAOYSA-N 0.000 claims description 3
- LJAGOFREPKQXID-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1,2-benzothiazole Chemical compound C=1C=CC=2SN=CC=2C=1OCC1CO1 LJAGOFREPKQXID-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- JCMBRWFSEQUKDN-UHFFFAOYSA-N 1-(1,2-benzothiazol-4-yloxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=NS2 JCMBRWFSEQUKDN-UHFFFAOYSA-N 0.000 claims description 2
- KEOAVHVLEQAUMH-UHFFFAOYSA-N 1-(1,2-benzothiazol-4-yloxy)-3-(tert-butylamino)propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC2=C1C=NS2 KEOAVHVLEQAUMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 5
- 230000000747 cardiac effect Effects 0.000 abstract description 4
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 3
- 238000011321 prophylaxis Methods 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
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- 229940039009 isoproterenol Drugs 0.000 description 13
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000002585 base Substances 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000008298 dragée Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
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- 235000012222 talc Nutrition 0.000 description 6
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 3
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- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 3
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
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- 239000000284 extract Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2704794A DE2704794C3 (de) | 1977-02-05 | 1977-02-05 | Aminopropanolderivate des 4-Hydroxy-l^-benzisothiazols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS202007B2 true CS202007B2 (en) | 1980-12-31 |
Family
ID=6000408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS78734A CS202007B2 (en) | 1977-02-05 | 1978-02-03 | Method of producing aminoderivatives of 4-hydroxy-1,2-benzoisothiazole |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4168317A (de) |
| JP (1) | JPS5398962A (de) |
| AT (1) | AT360525B (de) |
| AU (1) | AU516500B2 (de) |
| BE (1) | BE863622A (de) |
| CA (1) | CA1103680A (de) |
| CH (1) | CH635086A5 (de) |
| CS (1) | CS202007B2 (de) |
| DD (1) | DD133948A5 (de) |
| DE (1) | DE2704794C3 (de) |
| DK (1) | DK145342C (de) |
| ES (1) | ES466627A1 (de) |
| FI (1) | FI780199A7 (de) |
| FR (1) | FR2379529A1 (de) |
| GB (1) | GB1595383A (de) |
| GR (1) | GR65963B (de) |
| HU (1) | HU175881B (de) |
| IE (1) | IE46322B1 (de) |
| IL (1) | IL53889A (de) |
| IT (1) | IT1104142B (de) |
| LU (1) | LU78999A1 (de) |
| NL (1) | NL7801106A (de) |
| NO (1) | NO147384C (de) |
| SE (1) | SE433848B (de) |
| SU (1) | SU697052A3 (de) |
| ZA (1) | ZA78652B (de) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1058822A (en) * | 1963-07-30 | 1967-02-15 | Ici Ltd | 3-amino-2-hydroxypropoxy heterocyclic derivatives |
| US3997548A (en) * | 1973-12-19 | 1976-12-14 | Gulf Research & Development Company | Hydroxy-2,1-benzisothiazoles |
-
1977
- 1977-02-05 DE DE2704794A patent/DE2704794C3/de not_active Expired
-
1978
- 1978-01-04 GR GR55098A patent/GR65963B/el unknown
- 1978-01-23 FI FI780199A patent/FI780199A7/fi not_active Application Discontinuation
- 1978-01-25 IL IL53889A patent/IL53889A/xx unknown
- 1978-01-27 GB GB3342/78A patent/GB1595383A/en not_active Expired
- 1978-01-27 AU AU32793/78A patent/AU516500B2/en not_active Expired
- 1978-01-30 US US05/873,546 patent/US4168317A/en not_active Expired - Lifetime
- 1978-01-31 NL NL7801106A patent/NL7801106A/xx not_active Application Discontinuation
- 1978-01-31 IE IE207/78A patent/IE46322B1/en unknown
- 1978-02-01 IT IT47866/78A patent/IT1104142B/it active
- 1978-02-03 SE SE7801303A patent/SE433848B/sv unknown
- 1978-02-03 CH CH122478A patent/CH635086A5/de not_active IP Right Cessation
- 1978-02-03 LU LU78999A patent/LU78999A1/de unknown
- 1978-02-03 BE BE184874A patent/BE863622A/xx not_active IP Right Cessation
- 1978-02-03 FR FR7803021A patent/FR2379529A1/fr active Granted
- 1978-02-03 DK DK50078A patent/DK145342C/da not_active IP Right Cessation
- 1978-02-03 NO NO780388A patent/NO147384C/no unknown
- 1978-02-03 AT AT75678A patent/AT360525B/de not_active IP Right Cessation
- 1978-02-03 HU HU78BA3627A patent/HU175881B/hu unknown
- 1978-02-03 SU SU782573149A patent/SU697052A3/ru active
- 1978-02-03 CS CS78734A patent/CS202007B2/cs unknown
- 1978-02-03 DD DD78203554A patent/DD133948A5/de unknown
- 1978-02-03 ZA ZA00780652A patent/ZA78652B/xx unknown
- 1978-02-03 CA CA296,200A patent/CA1103680A/en not_active Expired
- 1978-02-03 ES ES466627A patent/ES466627A1/es not_active Expired
- 1978-02-06 JP JP1156078A patent/JPS5398962A/ja active Pending
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