CS270145B1 - 6-benzylidenamino-2-n-hexylthiobenzothiazole - Google Patents
6-benzylidenamino-2-n-hexylthiobenzothiazole Download PDFInfo
- Publication number
- CS270145B1 CS270145B1 CS888362A CS836288A CS270145B1 CS 270145 B1 CS270145 B1 CS 270145B1 CS 888362 A CS888362 A CS 888362A CS 836288 A CS836288 A CS 836288A CS 270145 B1 CS270145 B1 CS 270145B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- compound
- prati
- odlereva
- ethanol
- hexylthiobenzothiazole
- Prior art date
Links
- -1 6-benzylidenamino-2-n-hexylthiobenzothiazole Chemical compound 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 241000186367 Mycobacterium avium Species 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Β·1 připravený dateraz neznéay 6- -henzylidénaaina-2-n-hexyltiahenzatiaζ·1 vzarca I..Syntéza uvedenej zlúčenin . ny sa uskutečňuje reakciau 6-aaine-2-n- -hexyltiehenzetiazelu e henzaldehydea v etanele za varu. Zlúčenina je antiaykehakteriélne účinná prati typicljýa a * atypický* tuherkuleznya aykehakteriáa, najafi prati Mycehaeteriua fartuitua.Β · 1 ready dateraz strange 6- -henzylidénaaina-2-n-1 · hexyltiahenzatiaζ Synthesis of said compound . The reaction of 6-aaine-2-n- -hexyltiehenzetiazel e henzaldehydea in ethanol at boiling. The compound is anti-cyclohexylic effective prati typicljýa a * atypical * tuherkuleznya aykehakteriáa, najafi prati Mycehaeteriua fartuitua.
Description
Predaetoa vynálezu je 6-kenzylidénaaino-2-n-kexyltiokenzotiazol.The present invention is 6-kenzylideneamino-2-n-kexylthiokenzothiazole.
Deteraz koli znáae viaceré antiaykokakteriálne účinné deriváty kenzotiazolu. /Sidéevá, E. a Odlerevá, Ž., 6sl. Λ0 189212 /1978/, Sidéevá, E. a Odlerevá, Ž., 6el. AO 195149/1979/, Sidéevá, E. a Odlerevá, ž., Sel. AO 2Ó7299 /1980/, Sedéová, E. a Odlerevá, Ž., Čel. AO 2Í645O /1982/, Sidéevá, E. a Odlerevá, 2., 6eí. AO 225015 /1983/, Sidéevá, E. a Odlerevá, Ž., Cel. AO 239438 /1985/, Sidéevá, E, a Odlerevá, ž., Čel. AO 242017 /1985/ a $i*éová, E. a Odlerevá, 2., čel, AO 250557 /1986//. Uvedené slúčeniny aajd v poloh·'6 kenzénevéhe kruhu aainebkupinu, alek· ed nej edveáenú aaideskuyinu reap, iaideakupinuk iTo date, several anti-incocacterial active kenzothiazole derivatives are known. / Sidéevá, E. and Odlerevá, Ž., 6p. 180 189212/1978 /, Sidéeva, E. and Odlereva, Ž., 6el. AO 195149 (1979), Sidéeva, E. and Odlereva, b., Sel. AO 2Ó7299 / 1980 /, Sedéová, E. and Odlerevá, Ž., Čel. AO 2í645O / 1982 /, Sidéeva, E. and Odlereva, 2., 6eí. AO 225015 (1983), Sidéeva, E. and Odlereva, Ž., Cel. AO 239438/1985 /, Sidéeva, E, and Odlereva, b., Cel. AO 242017 (1985) and E. and Odlereva, 2., front, AO 250557 (1986). Said compounds are also in the 6-position of the kenzene ring of the aaine group, but also of the aaideskuyine reap, iaideakupinuk i
Teraz eae zistili, íe deteraz neznáaa zlúčenina xaerca I ’Now eae have found that the compound xaerca I ’is still unknown.
je antiaykokakteriálne účinná preti typickýa a atypiokýa tukerkuléznya aykokaktériáa najati pretl Myoekaoteriua /H,/ fertuitua. Súčaene hal zlatěný eyéaok propravy uvodonej zlúčeniny na káze S-aalne-2-n-hexyltiekenzetiazelu /Sidéevá, E. a Odlerevá, Ϊ., čel. AO 829212/1978//, který aa vyznačuje týa, le 6-aaine-2-j»-hoxyltioken«otiasol aa nooká roagov-ať a ekvivalentnýa anožstvea kenzaldehydu v etanOle za varu, ' , ' |is an antiaycocacterial active against typical and atypical fat-based myocardial lysis and is mediated by Myoekaoteriua / H, / fertuitua. The combined hal gold eyéaok of the preparation of the title compound on the S-aalne-2-n-hexylthienzenzetiazel sermon [Sidéevá, E. and Odlerevá, Ϊ., Č. AO 829212 (1978), which denotes 6-aaine-2-j-ethoxylthiokene otiasol aa nook roagov-a and an equivalent amount of kenzaldehyde in ethanol at boiling, ',' |
Nasledujúee příklady kližSie osvetťujú, ale nijaké neekaedzujú přípravu a vlastnosti zlúčeniny podía vynálezu.The following examples illustrate, but do not limit, the preparation and properties of the compound of the invention.
Příklad 1Example 1
Příprava 6-kenzylidénanine-2-n-kexyltiokenzotia2oluPreparation of 6-benzylideneanine-2-n-kexylthiokenzothiazole
6-Aaino-2-hexyltiokenzotiazol /5,3 g, 0,02 ael/ aa rozpustil v etanele /20 oa3/, k rezteku ea přidal kenzaldehyd /2,1 gt 0,02 ael/ a reakčná zaee aa zahriala na 5 áinút do varu. K reakčnej zaeei po eohladení áa tepletu aieatneati sa přidala studená veda /10 oaV a po 3 hodinách sa izeleval surový predukt e t.t. 73 až 74,5 *0 v anožstve 3,6ig /50,7 ¢/.6-Amino-2-hexyltiokenzotiazol / 5.3 g, 0.02 AEL / a, dissolved in etanele / 20 o 3 /, e and added to rezteku kenzaldehyd / 0.02 2.1 g t AEL / aa, and the reaction warmed to zaee 5 minutes to boil. Cold science (10 ° C) was added to the reaction mixture after cooling to room temperature, and after 3 hours, the crude product was collected in an amount of 73-74.5% in an amount of 3.6 μg (50.7%).
Látka kela prekryStalizevaná ze nesl etanel. - veda v peaere 4j_l za peužitia aktívnehe uhlia. Získal sa čistý 5-kenzylidénaaihe-2-n-hsxyltiokenzotiazol s t.t.73,5 až 74,5 *0, M.h. i 354,54. ।'Kela fabric overlaid from supported ethanol. - science in peaere 4j_l for the use of activated carbon. Pure 5-benzylidene and 2-n-hexylthiokenzothiazole were obtained, m.p. 73.5-74.5%, M.h. and 354.54. । '
Pře ^20^22^2^2 vypočítané fit C 67,76 H 6,25 N 7,90 S 18,09 zistené 67,85 6,53 7,8518,22For ^ 20 ^ 22 ^ 2 ^ 2 calculated fit C 67.76 H 6.25 N 7.90 S 18.09 found 67.85 6.53 7.8518.22
Příklad 2 'Example 2 '
Antiaykekakteriálna účinnost* zlúčeniny. pedía vynálezu v porovnaní a účinnesťeu Izeniketínhydrazidu a 2-aerkaptekenzotiazolu.Antiaykecacterial activity * of the compound. according to the invention in comparison with the efficacy of iseniketin hydrazide and 2-aeraptecenzothiazole.
Antiaykekakteriálna účinnesť preti tukerkuléznya nykekaktdriáa k«la slddevaná v tekuté j Sulevej pSde zrieievaoía testea. Ake rezpúžťadle kel peužitý iiaetylsulfexid. VýslednáThe antifungal activity has been shown to be effective in liquid treatment in a liquid solution. The solvent used is ethyl sulfexide. The resulting
MIC « ainiaálna inhikičná kenoentráoia vMg oa“\ INH Izeniketínhydrazid, 2-MBT . 2-aerkaptekenzetiaZel. Siastečná inhikičná kenoentráoia je udaná v zátverke.MIC: Initial Inhibitory Kenoenterology in Mg O 2 Isinethetine Hydrazide, 2-MBT. 2-aerkaptekenzetiaZel. The partial injection kenoentration is given in parentheses.
CS 270 145 BlCS 270 145 Bl
Významný je fakt, že zlúčenina pedía vynálezu avejeu účinnesteu preti M. avium převyšuje zavedený preparát Izeniazid /INH, Izeniketínhydrazid/ dvejnásebne a účinneeťeu preti M. fertuitum štvernásebne, pritem má účinnesť perevnatáínú a účinnesteu uvedenéhe preparátu preti M. tu>erculesÍB Ηβ7®ν a M· kanaasii.Important is the fact that the compound of the invention specialization avejeu účinnesteu preti M. avium exceeds the established formulation Izeniazid / INH Izeniketínhydrazid / dvejnásebne and A. Preti účinneeťeu fertuitum štvernásebne, pritem the účinnesť perevnatáínú and účinnesteu uvedenéhe preparation A. Preti here> erculesÍB Ηβ7® and ν M · kanaasii.
Zlúčeninu pedťa vynálezu nežne peužívat ake účinnú zležku antimykebakteriálnych prípravkev, alete ake medzlpredukt pre dalšie syntézy.The compound of the present invention cannot be used as an effective ingredient of antimycebacterial agents, but also as an intermediate for further syntheses.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS888362A CS270145B1 (en) | 1988-12-16 | 1988-12-16 | 6-benzylidenamino-2-n-hexylthiobenzothiazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS888362A CS270145B1 (en) | 1988-12-16 | 1988-12-16 | 6-benzylidenamino-2-n-hexylthiobenzothiazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS836288A1 CS836288A1 (en) | 1989-09-12 |
| CS270145B1 true CS270145B1 (en) | 1990-06-13 |
Family
ID=5434060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS888362A CS270145B1 (en) | 1988-12-16 | 1988-12-16 | 6-benzylidenamino-2-n-hexylthiobenzothiazole |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS270145B1 (en) |
-
1988
- 1988-12-16 CS CS888362A patent/CS270145B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS836288A1 (en) | 1989-09-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI337998B (en) | Substituted imidazoles | |
| DE69132961T2 (en) | STYRYL-SUBSTITUTED HETEROARYL COMPOUNDS INHIBITING EGF RECEPTOR TYROSINE KINASE | |
| JP2727199B2 (en) | Novel imidazolidine substituted with a hydroxymethyl group and a substituted phenyl group, method for producing the same, use as a medicament, pharmaceutical composition containing the same, and intermediate for producing the same | |
| US5171851A (en) | Imidazole substituted benzoxazine or benzothiazine derivatives | |
| CA1265794A (en) | 4h-triazolo[4,3-a][1,4] benzodiazepin compounds, process for preparation thereof, their applications as drugs and compositions containing same | |
| TW201534586A (en) | Novel CYP17 inhibitors/antiandrogens | |
| JP3186771B2 (en) | A new selective aromatase inhibitor | |
| CA2069261A1 (en) | Pyrimidine derivatives, their preparation process, the new intermediates obtaines, their application as drugs and the pharmaceutical compositions containing them | |
| JPS60100560A (en) | Antidepressive 1,2,4-triazolone compound | |
| EP0040591A1 (en) | Pyridoxine derivatives, process for their preparation and their therapeutical use | |
| HU203076B (en) | Process for producing arylhydroxamic acid derivatives and pharmaceutical compositions comprising such compounds, as well as composition regulating plant growth and delaying fading of cut flowers | |
| FR2715402A1 (en) | New substd. phenyl-imidazolidine(s) which fix to androgen receptors | |
| CA2056967A1 (en) | Use of organic compounds | |
| BE1000573A4 (en) | DERIVATIVES 1- (hydroxystyryl) -5 H 2,3-BENZODIAZEPINE, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING. | |
| FR2464264A1 (en) | 6- (PYRIDINYL) -3 (2H) PYRIDAZINONES, THEIR PREPARATION AND THEIR THERAPEUTIC USE | |
| CS270145B1 (en) | 6-benzylidenamino-2-n-hexylthiobenzothiazole | |
| FR2612517A1 (en) | BENZOXAZINE DERIVATIVES, METHODS FOR PREPARING THESE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME | |
| WO2025077774A1 (en) | At2r antagonist and use thereof | |
| NO143316B (en) | ANALOGY PROCEDURE FOR THE PREPARATION OF NEW OXSAZOLIDINONS WITH PHARMACODYNAMIC PROPERTIES | |
| EP0429360A2 (en) | Inhibition of withdrawal syndrome | |
| EP0145019B1 (en) | Pyridazinone derivatives and salts thereof | |
| FR2536398A1 (en) | NEW HETEROCYCLIC COMPOUNDS | |
| FR2499991A1 (en) | NOVEL 2,1,3-BENZOTHIADIAZOLES AND 2,1,3-BENZOXADIAZOLES, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINES | |
| FR2514006A1 (en) | ACYLAMINO-4 AZA-1 ADAMANTANES, PROCESS FOR THEIR PREPARATION, AND THERAPEUTIC APPLICATION | |
| US4288448A (en) | N-Substituted imidazole derivatives, and their use |