DE1670907B2 - N-disubstituierte 3-amino-1,2benzisothiazole und verfahren in ihrer herstellung - Google Patents
N-disubstituierte 3-amino-1,2benzisothiazole und verfahren in ihrer herstellungInfo
- Publication number
- DE1670907B2 DE1670907B2 DE1967F0053242 DEF0053242A DE1670907B2 DE 1670907 B2 DE1670907 B2 DE 1670907B2 DE 1967F0053242 DE1967F0053242 DE 1967F0053242 DE F0053242 A DEF0053242 A DE F0053242A DE 1670907 B2 DE1670907 B2 DE 1670907B2
- Authority
- DE
- Germany
- Prior art keywords
- connection
- disubstituted
- amino
- benzisothiazolium
- benzisothiazole
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical class NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 210000003608 fece Anatomy 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001480043 Arthrodermataceae Species 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 230000037304 dermatophytes Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- CPYSWRYVSINXMC-UHFFFAOYSA-N n-ethyl-1,2-benzothiazol-3-amine Chemical compound C1=CC=C2C(NCC)=NSC2=C1 CPYSWRYVSINXMC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BOMDDXNRKMWRTF-UHFFFAOYSA-N 1,2-benzothiazole;hydrochloride Chemical compound Cl.C1=CC=C2C=NSC2=C1 BOMDDXNRKMWRTF-UHFFFAOYSA-N 0.000 description 1
- MORCMRZOISVFRS-UHFFFAOYSA-N 3-chloro-1,2-benzothiazol-2-ium;chloride Chemical compound [Cl-].C1=CC=C2C(Cl)=[NH+]SC2=C1 MORCMRZOISVFRS-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- -1 alkyl radical Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000048 toxicity data Toxicity 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 (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0053242 DE1670907B2 (de) | 1967-08-16 | 1967-08-16 | N-disubstituierte 3-amino-1,2benzisothiazole und verfahren in ihrer herstellung |
| CH915368A CH516581A (de) | 1967-08-16 | 1968-06-20 | Verfahren zur Herstellung von N-disubstituierten 3-Amino-1,2-benzisothiazolen |
| IL6830231A IL30231A (en) | 1967-08-16 | 1968-06-23 | 3-Amino-1,2-benzaziothiazoles N -duclear, their preparation and pharmaceutical preparations containing them |
| GB1229996D GB1229996A (OSRAM) | 1967-08-16 | 1968-07-31 | |
| AT747168A AT279608B (de) | 1967-08-16 | 1968-07-31 | Verfahren zur Herstellung neuer N-disubtituierter 3-Amino-1,2-benzisothiazole |
| NL6811549A NL6811549A (OSRAM) | 1967-08-16 | 1968-08-14 | |
| BR201542/68A BR6801542D0 (pt) | 1967-08-16 | 1968-08-16 | Processo para preparacao de 3-amino-1,2-benzisotiazois-n-dissubstituidos |
| ES357317A ES357317A1 (es) | 1967-08-16 | 1968-08-16 | Procedimiento para la preparacion de 3-amino -i,2-benziso- tiazoles n-disustituidos. |
| BE719566D BE719566A (OSRAM) | 1967-08-16 | 1968-08-16 | |
| FR1601118D FR1601118A (OSRAM) | 1967-08-16 | 1968-08-18 | |
| FR173955A FR8097M (OSRAM) | 1967-08-16 | 1968-11-15 | |
| US00182246A US3787572A (en) | 1967-08-16 | 1971-09-29 | N-disubstituted 3-amino-1,2-benzisothiazoles as antimycotic agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0053242 DE1670907B2 (de) | 1967-08-16 | 1967-08-16 | N-disubstituierte 3-amino-1,2benzisothiazole und verfahren in ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1670907A1 DE1670907A1 (de) | 1971-03-18 |
| DE1670907B2 true DE1670907B2 (de) | 1976-07-22 |
Family
ID=7106127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967F0053242 Granted DE1670907B2 (de) | 1967-08-16 | 1967-08-16 | N-disubstituierte 3-amino-1,2benzisothiazole und verfahren in ihrer herstellung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3787572A (OSRAM) |
| AT (1) | AT279608B (OSRAM) |
| BE (1) | BE719566A (OSRAM) |
| BR (1) | BR6801542D0 (OSRAM) |
| CH (1) | CH516581A (OSRAM) |
| DE (1) | DE1670907B2 (OSRAM) |
| ES (1) | ES357317A1 (OSRAM) |
| FR (2) | FR1601118A (OSRAM) |
| GB (1) | GB1229996A (OSRAM) |
| IL (1) | IL30231A (OSRAM) |
| NL (1) | NL6811549A (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2609864C2 (de) * | 1976-03-10 | 1984-02-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3-Amino-1,2-benzisothiazolen |
| US4112105A (en) * | 1977-05-04 | 1978-09-05 | Sterling Drug Inc. | Anti-inflammatory 3-(substituted-amino)-2,1-benzisothiazoles |
| US4411901A (en) * | 1981-12-23 | 1983-10-25 | Mead Johnson & Company | Benzisothiazole and benzisoxazole piperazine derivatives |
| US4590196A (en) * | 1984-08-23 | 1986-05-20 | Bristol-Myers Company | Analgesic 1,2-benzisothiazol-3-ylpiperazine derivatives |
| PE20070847A1 (es) * | 2005-11-21 | 2007-09-21 | Basf Ag | Compuestos derivados de 3-amino-1,2-bencisotiazol como insecticidas |
-
1967
- 1967-08-16 DE DE1967F0053242 patent/DE1670907B2/de active Granted
-
1968
- 1968-06-20 CH CH915368A patent/CH516581A/de not_active IP Right Cessation
- 1968-06-23 IL IL6830231A patent/IL30231A/en unknown
- 1968-07-31 GB GB1229996D patent/GB1229996A/en not_active Expired
- 1968-07-31 AT AT747168A patent/AT279608B/de not_active IP Right Cessation
- 1968-08-14 NL NL6811549A patent/NL6811549A/xx unknown
- 1968-08-16 BE BE719566D patent/BE719566A/xx unknown
- 1968-08-16 ES ES357317A patent/ES357317A1/es not_active Expired
- 1968-08-16 BR BR201542/68A patent/BR6801542D0/pt unknown
- 1968-08-18 FR FR1601118D patent/FR1601118A/fr not_active Expired
- 1968-11-15 FR FR173955A patent/FR8097M/fr not_active Expired
-
1971
- 1971-09-29 US US00182246A patent/US3787572A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES357317A1 (es) | 1970-03-16 |
| BE719566A (OSRAM) | 1969-02-17 |
| AT279608B (de) | 1970-03-10 |
| IL30231A0 (en) | 1968-08-22 |
| IL30231A (en) | 1972-01-27 |
| NL6811549A (OSRAM) | 1969-02-18 |
| DE1670907A1 (de) | 1971-03-18 |
| CH516581A (de) | 1971-12-15 |
| FR1601118A (OSRAM) | 1970-08-10 |
| FR8097M (OSRAM) | 1970-07-20 |
| BR6801542D0 (pt) | 1973-02-22 |
| GB1229996A (OSRAM) | 1971-04-28 |
| US3787572A (en) | 1974-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |