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84 PATENTNI ZAHTEVKI 1. Postopek za pripravo Nr(l,2-cis-2-halogenociklopropil)-subst.derivata pindonkarboksilne kisline, prikazane z naslednjo formuloA process for the preparation of Nr (1,2-cis-2-halocyclopropyl) -subst. Derivatives of pindonecarboxylic acid shown by the following formulakjer R1 predstavlja amino skupino, metilamino skupino, hidroksilno skupino, tiolno skupino ali atom vodika, R predstavlja 4-, 5-ali 7-člensko ciklično amino skupino, ki ima vsaj en substituent izbran izmed hidroksilne skupine, alkilne skupine z 1 do 6 atomi ogljika, polimetilenske skupine z 2 do 5 atomi ogljika, ki skupaj z obročnim atomom, na katerega je vezan, tvori spiro enoto, aminoalkilno skupino ali amino skupino, ciklična amino skupina pa lahko vsebuje premostitveno enoto, da se tvori biciklična amino skupina, in lahko vsebuje vsaj en hetero atom, izbran izmed atoma dušika, atoma kisika in atoma žvepla v njenem obroču, ali R2 predstavlja ciklično amino skupino, prikazano s formulowherein R 1 represents an amino group, a methylamino group, a hydroxyl group, a thiol group or a hydrogen atom, R represents a 4-, 5- or 7-membered cyclic amino group having at least one substituent selected from a hydroxyl group, an alkyl group having 1 to 6 atoms carbon, a polymethylene group having 2 to 5 carbon atoms which, together with the ring atom to which it is attached, forms a spiro unit, an aminoalkyl group or an amino group, and the cyclic amino group may contain a bridging unit to form a bicyclic amino group, and may contains at least one hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom in its ring, or R2 represents a cyclic amino group represented by the formulaali R,0NHor R 10NHkjer R3, R4, R5, R6, R10 in R11, ki so lahko enaki ali različni, predstavljajo alkilno skupino z 1 do 6 atomi ogljika ali atom vodika; A predstavlja C-X3 ali atom dušika; X1 in X , ki sta lahko enaka ali različna, vsakokrat predstavljata atom halogena, X pa predstavlja atom halogena, alkilno skupino z 1 do 6 atomi ogljika, alkoksilno skupino z 1 do 6 atomi ogljika, ciano skupino, trifluorometilno skupino ali atom vodika; s pridržkom, da je izključen primer, kjer je R atom vodika in R piperazinski ali 4-alkil-substituiran piperazinski ostanek, ali njegove soli, 85 označen s tem, da presnovimo 7-halogeno-l-(l,2-cis-2-fluorociklopropil)piridon karboksilno kislino z naslednjo formulo R1 Owherein R 3, R 4, R 5, R 6, R 10 and R 11, which may be the same or different, represent an alkyl group having 1 to 6 carbon atoms or a hydrogen atom; A represents C-X3 or a nitrogen atom; X1 and X, which may be the same or different, each represent a halogen atom, and X represents a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, a trifluoromethyl group or a hydrogen atom; with the proviso that it is excluded that R is a hydrogen atom and R is a piperazine or 4-alkyl-substituted piperazine residue, or salts thereof, 85 characterized in that 7-halogen-1- (1,2-cis-2) is reacted -fluorocyclopropyl) pyridone carboxylic acid of the following formula R1 Okjer imajo R1, X1, X2 in A zgoraj definirani pomen, X pa predstavlja atom halogena, s ciklično aminsko spojino s formulo R2-H, ki je lahko zaščitena z običajno zaščitno skupino, pri čemer ima R zgoraj navedeni pomen.wherein R1, X1, X2 and A have the meaning defined above and X represents a halogen atom, with a cyclic amine compound of formula R2-H which may be protected by a conventional protecting group, wherein R has the meaning given above.2. Postopek po zahtevku 1, označen s tem, daje R2 pirolidinski, diazabicikloheptanski ali diazabiciklooktanski ostanek.Process according to Claim 1, characterized in that R 2 is a pyrrolidine, diazabicycloheptane or diazabicyclooctane residue.3. Postopek po zahtevku 1 ali 2, označen s tem, da je R ciklična amino skupina, izvedena iz cikličnega amina, ki obsega en sam stereoizomer.Process according to Claim 1 or 2, characterized in that R is a cyclic amino group derived from a cyclic amine comprising a single stereoisomer.4. Postopek po zahtevku 3, označen s tem, daje R2 3-amino pirolidinilna skupina.Process according to Claim 3, characterized in that R 2 is a 3-amino pyrrolidinyl group.5. Postopek po zahtevku 4, označen s tem, daje R2 7-amino-5-azaspiro[2.4]heptan-5-ilna skupina.Process according to Claim 4, characterized in that R 2 is a 7-amino-5-azaspiro [2.4] heptan-5-yl group.6. Postopek po zahtevku 1, označen s tem, daje X2 atom fluora. Za Daiichi Seiyaku Co., Ltd.:Process according to Claim 1, characterized in that X 2 is a fluorine atom. For Daiichi Seiyaku Co., Ltd .:
SI8910875A1988-04-271989-04-26Optically active pyridone carboxylic acid derivatives
SI8910875B
(en)
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