1,3-THIAZINES

• Main Authors: HARSANYI K,HU, TAKACS K,HU, TARDOS L,HU, KISS P,HU, NADOR K,HU, SIMAY A,HU, KORBONITS D,HU, LESZKOVSZKY G,HU, BODROGI I,HU
• Format: Patent
• Language: English
• Published: 27.11.1973
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

1286315 Thiazine; thiazoline and thiazolidine derivatives CHINOIN GYOGYSZER ES VEGYESZETI TERMEKEK GYARA RT 3 Nov 1969 [6 Nov 1968] 53867/69 Headings C2C and C2P Novel compounds I, II and III in which R 1 is naphthyl (which may be substituted by one or more alkyl, alkoxy, halo, amino, sulphamoyl, carboxy, functionally modified carboxy, acyl or alkyl- or aryl-sulphonyl and/or hydrogenated) and A is or in which R 2 is alkyl, aralkyl or aryl and R 3 is H, alkyl, aralkyl or aryl and their salts are prepared:-(1) by reacting R 1 -NHCSNH 2 with C 2 H 3 X 2 R 2 or C 3 H 5 X 2 R 3 (X = halo) (halo attached to 1 and 2 or 1 and 3 positions respectively); (2) by reacting R 1 -NCS with C 2 H 3 (OH)(NH 2 )R 2 or C 3 H 5 (OH) (NH 2 )R 3 (amino and hydroxy attached to 1 and 2 or 1 and 3 positions respectively); (3) by cyclizing a reactive ester of a compound R 1 NHCSNHC 2 H 3 (OH)R 2 or (4) by reacting R 1 NCS or R 1 -NHCSNH 2 with C 2 H 3 (X)(NH 2 )R 2 or C 3 H 5 (X)(NH 2 )R 3 (halo and NH 2 attached to 1 and 2 or 1 and 3 positions respectively); (5) by reacting a compound IV in which R 4 is alkyl with R 1 NH 2 (6) by reacting R 1 NH 2 with C 2 H 3 X(NCS)R 2 or C 3 H 5 X(NCS)R 3 ; and (7) by reacting a compound V with R 1 NH 2 N-( or 2-naphthyl) .Y1.( 3-hydroxypropyl)-thiourea is prepared by reacting 3-aminopropanol with 1 or 2-naphthyl.isothiocyanate. N-(naphthyl -1) -N1- (3-phosphatopropyl) -thiourea disodium salt is prepared by reacting 3-aminopropyl dihydrogen-phosphate hydrate with naphth-1-yl isocyanate in NaOH. (2-Methyl-naphth-l-yl) isothiocyanate is prepared by boiling the corresponding thiourea with chlorobenzene. (2-Methoxy-naphth. 1-yl) isothiocyanate is similarly prepared. N-(4.chloronaphthyl- 1 )-N1-(3.hydroxypropyl)-thiourea is prepared by reacting 3-aminopropanol with the appropriate isothiocyanate. N - (5,6,7,8 - tetrahydronaphthyl - 1) - N1 - (3- hydroxypropyl)thiourea; N-(5,6,7,8-tetrahydronaphthyl-2)-N1-3-hydroxypropyl) -thiourea; N-(1- acetyl-naphthyl-4 or 7).N1-( 3-hydroxypropyl)-thio. urea and N- ( 1-naphthyl )-N1-(1-hydroxy-but-2-yl )- thiourea are similarly prepared by reaction of the appropriate aminoalkanol with the appropriate isothiocyanate. Pharmaceutical compositions comprise a compound of Formula I, II or III and a suitable carrier are administered enterally or parenterally and have sedative, tranquillizing, spasmolytic and prolonged hypotensive properties. Pesticidal compositions comprise a compound of Formula I, II or III and an inert carrier.