CH500221A - Verfahren zur Herstellung von N-disubstituierten 3-Amino-1,2-benzisothiazol-Derivaten - Google Patents
Verfahren zur Herstellung von N-disubstituierten 3-Amino-1,2-benzisothiazol-DerivatenInfo
- Publication number
- CH500221A CH500221A CH1168268A CH1168268A CH500221A CH 500221 A CH500221 A CH 500221A CH 1168268 A CH1168268 A CH 1168268A CH 1168268 A CH1168268 A CH 1168268A CH 500221 A CH500221 A CH 500221A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzisothiazole
- amino
- alkyl
- radicals
- disubstd
- Prior art date
Links
- 230000001857 anti-mycotic effect Effects 0.000 title abstract description 4
- 239000002543 antimycotic Substances 0.000 title abstract description 4
- -1 araliphatic Chemical group 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- WIJQCPIRWXSWQG-UHFFFAOYSA-N 1,2-benzothiazol-3-amine Chemical class C1=CC=C2C(N)=NSC2=C1 WIJQCPIRWXSWQG-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000012435 aralkylating agent Substances 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 4
- 241001045770 Trichophyton mentagrophytes Species 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 4
- CPYSWRYVSINXMC-UHFFFAOYSA-N n-ethyl-1,2-benzothiazol-3-amine Chemical compound C1=CC=C2C(NCC)=NSC2=C1 CPYSWRYVSINXMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BCPVKLRBQLRWDQ-UHFFFAOYSA-N 3-chloro-1,2-benzothiazole Chemical compound C1=CC=C2C(Cl)=NSC2=C1 BCPVKLRBQLRWDQ-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- BYVLTADRKHJIGJ-UHFFFAOYSA-N CCC1=CC(=CC=C1)CNC2=NSC3=CC=CC=C32 Chemical compound CCC1=CC(=CC=C1)CNC2=NSC3=CC=CC=C32 BYVLTADRKHJIGJ-UHFFFAOYSA-N 0.000 description 1
- XPLUMBGIILESCI-UHFFFAOYSA-N CCC1CCCC(C1)NC2=NSC3=CC=CC=C32 Chemical compound CCC1CCCC(C1)NC2=NSC3=CC=CC=C32 XPLUMBGIILESCI-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- MPXAMQWYYGMRGG-UHFFFAOYSA-N N,N-dibutyl-1,2-benzothiazol-3-amine Chemical compound C(CCC)N(C1=NSC2=C1C=CC=C2)CCCC MPXAMQWYYGMRGG-UHFFFAOYSA-N 0.000 description 1
- AXEPVTNANVZKQI-UHFFFAOYSA-N N,N-dimethyl-1,2-benzothiazol-3-amine Chemical compound CN(C1=NSC2=C1C=CC=C2)C AXEPVTNANVZKQI-UHFFFAOYSA-N 0.000 description 1
- WDCGQSFCBYBMCH-UHFFFAOYSA-N N-ethyl-3-methyl-1,2-benzothiazol-4-amine Chemical compound CC1=NSC2=C1C(=CC=C2)NCC WDCGQSFCBYBMCH-UHFFFAOYSA-N 0.000 description 1
- 241001507677 Penicillium commune Species 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- TVKLAMQDPUVOLS-UHFFFAOYSA-N n,n-diethyl-1,2-benzothiazol-3-amine Chemical compound C1=CC=C2C(N(CC)CC)=NSC2=C1 TVKLAMQDPUVOLS-UHFFFAOYSA-N 0.000 description 1
- NAFVOUXQZLUILW-UHFFFAOYSA-N n,n-dipropyl-1,2-benzothiazol-3-amine Chemical compound C1=CC=C2C(N(CCC)CCC)=NSC2=C1 NAFVOUXQZLUILW-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0053456 | 1967-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH500221A true CH500221A (de) | 1970-12-15 |
Family
ID=7106326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1168268A CH500221A (de) | 1967-09-09 | 1968-08-05 | Verfahren zur Herstellung von N-disubstituierten 3-Amino-1,2-benzisothiazol-Derivaten |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4538613B1 (es) |
| AT (1) | AT279609B (es) |
| CH (1) | CH500221A (es) |
| DE (1) | DE1670920A1 (es) |
| ES (1) | ES357965A1 (es) |
| NL (1) | NL6812660A (es) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0778271A3 (de) * | 1995-12-08 | 2000-03-22 | F. Hoffmann-La Roche Ag | Aminoalkyl-substituierte benzo-heterocyclische Verbindungen |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3343091A1 (de) * | 1983-11-29 | 1985-06-05 | Bayer Ag, 5090 Leverkusen | Verwendung von 3-amino-1,2-benzisothiazolen als mikrobizide zum schutz technischer materialien |
| WO2003087072A1 (en) * | 2002-03-29 | 2003-10-23 | Mochida Pharmaceutical Co., Ltd. | Therapeutic agent for endothelial disorder |
| EP2003975B1 (en) | 2006-03-31 | 2009-11-18 | Basf Se | 3-amino-1,2-benzisothiazole compounds for combating animal pest |
| ATE549325T1 (de) | 2007-01-26 | 2012-03-15 | Basf Se | 3-amino-1,2-benzisothiazol-verbindungen zur bekämpfung von tierpest ii |
-
1967
- 1967-09-09 DE DE19671670920 patent/DE1670920A1/de active Pending
-
1968
- 1968-08-05 CH CH1168268A patent/CH500221A/de not_active IP Right Cessation
- 1968-09-05 NL NL6812660A patent/NL6812660A/xx unknown
- 1968-09-09 ES ES357965A patent/ES357965A1/es not_active Expired
- 1968-09-09 JP JP6459468A patent/JPS4538613B1/ja active Pending
- 1968-09-09 AT AT875668A patent/AT279609B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0778271A3 (de) * | 1995-12-08 | 2000-03-22 | F. Hoffmann-La Roche Ag | Aminoalkyl-substituierte benzo-heterocyclische Verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6812660A (es) | 1969-03-11 |
| DE1670920A1 (de) | 1971-04-01 |
| JPS4538613B1 (es) | 1970-12-05 |
| AT279609B (de) | 1970-03-10 |
| ES357965A1 (es) | 1970-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |