DE1545844A1 - Verfahren zur Herstellung von N-substituierten 3-Aminobenzisothiazolen - Google Patents
Verfahren zur Herstellung von N-substituierten 3-AminobenzisothiazolenInfo
- Publication number
- DE1545844A1 DE1545844A1 DE19651545844 DE1545844A DE1545844A1 DE 1545844 A1 DE1545844 A1 DE 1545844A1 DE 19651545844 DE19651545844 DE 19651545844 DE 1545844 A DE1545844 A DE 1545844A DE 1545844 A1 DE1545844 A1 DE 1545844A1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- imino
- colorless
- alkyl
- halogen
- 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.)
- Withdrawn
Links
- -1 N-substituted 3-aminobenzisothiazoles Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- DMBUEUDLZHIAPD-UHFFFAOYSA-N 1-imino-1,2-benzothiazole Chemical compound N=S1N=CC2=C1C=CC=C2 DMBUEUDLZHIAPD-UHFFFAOYSA-N 0.000 description 1
- GFSWDFXIFKVJMS-UHFFFAOYSA-N 2-ethyl-1,2-benzothiazol-3-imine Chemical compound C(C)N1SC2=C(C1=N)C=CC=C2 GFSWDFXIFKVJMS-UHFFFAOYSA-N 0.000 description 1
- XQIHHPAETCQZAT-UHFFFAOYSA-N 2-methyl-1,2-benzothiazol-3-imine Chemical compound CN1SC2=C(C1=N)C=CC=C2 XQIHHPAETCQZAT-UHFFFAOYSA-N 0.000 description 1
- DFVKYFSTFSLMOY-UHFFFAOYSA-M 3-chloro-2-methyl-1,2-benzothiazol-2-ium;chloride Chemical compound [Cl-].C1=CC=C2C(Cl)=[N+](C)SC2=C1 DFVKYFSTFSLMOY-UHFFFAOYSA-M 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- AJQLEJAVGARHGQ-UHFFFAOYSA-N dithiosalicylic acid Chemical class OC1=CC=CC=C1C(S)=S AJQLEJAVGARHGQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00151929A US3790587A (en) | 1965-07-29 | 1971-06-10 | Antimycotic benzisothiazoline derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0046742 | 1965-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1545844A1 true DE1545844A1 (de) | 1969-12-18 |
Family
ID=7101207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651545844 Withdrawn DE1545844A1 (de) | 1965-07-29 | 1965-07-29 | Verfahren zur Herstellung von N-substituierten 3-Aminobenzisothiazolen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE684739A (enrdf_load_stackoverflow) |
| CH (1) | CH484181A (enrdf_load_stackoverflow) |
| CY (1) | CY541A (enrdf_load_stackoverflow) |
| DE (1) | DE1545844A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1088550A (enrdf_load_stackoverflow) |
| IL (1) | IL26178A (enrdf_load_stackoverflow) |
| NL (1) | NL6610677A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670967B2 (de) * | 1967-12-27 | 1977-10-13 | Bayer Ag, 5090 Leverkusen | 3-imino-1,2-benzisothiazolin-salze und verfahren zu ihrer herstellung |
| US6376530B1 (en) * | 1999-05-10 | 2002-04-23 | Merck & Co., Inc. | Cyclic amidines useful as NMDA NR2B antagonists |
-
1965
- 1965-07-29 DE DE19651545844 patent/DE1545844A1/de not_active Withdrawn
-
1966
- 1966-07-19 IL IL2617866A patent/IL26178A/xx unknown
- 1966-07-20 CH CH1046366A patent/CH484181A/de not_active IP Right Cessation
- 1966-07-28 GB GB3397166A patent/GB1088550A/en not_active Expired
- 1966-07-28 NL NL6610677A patent/NL6610677A/xx unknown
- 1966-07-28 BE BE684739D patent/BE684739A/xx unknown
-
1970
- 1970-06-05 CY CY54170A patent/CY541A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE684739A (enrdf_load_stackoverflow) | 1967-01-30 |
| GB1088550A (en) | 1967-10-25 |
| CY541A (en) | 1970-06-05 |
| NL6610677A (enrdf_load_stackoverflow) | 1967-01-30 |
| IL26178A (en) | 1970-03-22 |
| CH484181A (de) | 1970-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |