YU48052B - (S) - (+) - 2-ETHOXY-4- / N- (1- (2-PIPERIDINO-PHENYL) -3-METHYL-1-BUTYL-AMINOCARBONYL-METHYL-benzoic acid and procedures for its preparation - Google Patents

(S) - (+) - 2-ETHOXY-4- / N- (1- (2-PIPERIDINO-PHENYL) -3-METHYL-1-BUTYL-AMINOCARBONYL-METHYL-benzoic acid and procedures for its preparation

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Publication number
YU48052B
YU48052B YU113691A YU113691A YU48052B YU 48052 B YU48052 B YU 48052B YU 113691 A YU113691 A YU 113691A YU 113691 A YU113691 A YU 113691A YU 48052 B YU48052 B YU 48052B
Authority
YU
Yugoslavia
Prior art keywords
group
compound
general formula
carboxy
methyl
Prior art date
Application number
YU113691A
Other languages
Serbo-Croatian (sh)
Other versions
YU113691A (en
Inventor
W. Grell
A. Greischel
G. Zahn
M. Mark
H. Knorr
E. Rupprecht
U. Muller
Original Assignee
Dr. Karl Thomae Gmbh.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dr. Karl Thomae Gmbh. filed Critical Dr. Karl Thomae Gmbh.
Priority to SI9111136A priority Critical patent/SI9111136A/en
Priority to YU113691A priority patent/YU48052B/en
Publication of YU113691A publication Critical patent/YU113691A/en
Priority to HR940769A priority patent/HRP940769B1/en
Publication of YU48052B publication Critical patent/YU48052B/en

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  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

(S)-(+)-2-etoksi-4-/N-(1-(2-piperidino-fenil)-3-metil-1-butil)-aminokarbonil-metil/-benzoeva kiselina i njene soli sa neorganskim ili organskim kiselinama ili bazama. Postupak za pripremanje novog jedinjenja premaza htevifma 1 i 2, ili njegove fiziološki prihvatljive soli, naznačen time, što se a) (S)-amin, formule dovodi u reakciju sa karboksilnom kiselinom, opšte formule u kojoj W predstavlja karboksi-grupu, ili karboksi-grupu zaštićenu sa zaštitnim ostatkom, ili sa njenim za reakciju sposobnim derivatom, eventualno pripremljenim u reakcionoj smeši, a prema potrebi, zatim se vrši odsepljivanje zaštitnog ostatka, ili b) razleže (S)-jedinjenje, opšte formule u kojoj A predstavlja gurpu koja se hidrolizom, temolizom ili hidrogenolizom može prevesti u karboksi-grupu, ili c) (S)-jedinjenje, opšte formule u kojoj W' predstavlja karboksi-grupu ili alkoksikarbonilnu grupu, sa ukupno 2 do 5 atoma ugljenika, pri čemu alkilni deo alkoksi-grupe može da bude supstituisan sa fenilnom grupom, dovodi u reakciju sa jeidnjenjem opšte formule Z - CH2- CH3 (V) u kojoj Z predstavlja nukleofilnu grupu, koja se može zameniti, ili zajedno sa susednim atomom vodonika predstavlja diazo-grupu, a prema potrebi se zatim vrši hidroliza ili hidrogenoliza tako dobijenog jedinjenja, ili d) jedinjenje opšte formule u kojoj W' predstavlja karboksi-grupu ili alkoksikarbonilnu grupu, sa ukupno 2 do 5 atoma ugljenika, pri čemu alkilni deo alkoksi-grupe može da bude supstituisan sa fenil-grupom, a Y grupa formule enantioselektivno redukuje, a prema potrebi se zatim vrši hidroliza tako dobijenog jedinjenja, ili e) oksidira (S)-jedinjenje, opšte formule u kojoj W" predstavlja grupu koja se oksidacijom prevodi u karboksi-grupu, ili f) razdvaja smeša, koja se sastoji od bilo koje količine (S)-enan-tiomera, opšte formule II) i bilo koje količine (R)-enantiomera, opšte formule u kojima W' predstavlja karboksi-grupu ili alkoksikarbonilnu grupu, sa ukupno 2 do 5 atoma ugljenika, pri čemu alkilni deo alkoksi-grupe može da bude supstituisan sa fenil-grupom, a tako dobijeno jedinjenje, prema potrebi se prekristalisavanjem prevodi u jedinjenje sa većom enantiomernom čistoćom, pri čemu se kristalisanjem iz etanola/vode (2/1) dobija oblik sa visokom tačkom topljenja, 130 do 131В°C, a kristalisanjem iz petroletra/tolulola (5/3) oblik sa niskom tačkom topljenja, 99 do 101В°C, a tako dobijeno jedinjenje se prevodi u svoje soli, naročito u svoje fiziološki prihvatljive soli, sa neorganskim ili organskim kiselinama ili bazama. Prijava sadrži još 3 zavisna zahteva.(S) - (+) - 2-Ethoxy-4- / N- (1- (2-piperidino-phenyl) -3-methyl-1-butyl) -aminocarbonyl-methyl / -benzoic acid and its salts with inorganic or organic acids or bases. A process for the preparation of a novel coating compound of htevifm 1 and 2, or a physiologically acceptable salt thereof, wherein the a) (S) -amine of the formula is reacted with a carboxylic acid, of the general formula wherein W represents a carboxy group, or a carboxy -group protected with a protective residue, or a reaction-capable derivative thereof, possibly prepared in the reaction mixture and, if necessary, peeling off the protective residue, or b) separating the (S) compound, of the general formula wherein A represents a group which by hydrolysis, temolysis or hydrogenolysis may be converted to a carboxy group, or c) (S)-compound, of the general formula wherein W 'represents a carboxy group or alkoxycarbonyl group, with a total of 2 to 5 carbon atoms, wherein the alkyl moiety is alkoxy- of the group may be substituted with a phenyl group, reacting with the removal of the general formula Z - CH2 - CH3 (V) in which Z represents a nucleophilic group which may be replaced, or together with the adjacent at by hydrogen represents a diazo group, followed by hydrolysis or hydrogenolysis of the compound thus obtained, or d) a compound of the general formula wherein W 'represents a carboxy group or alkoxycarbonyl group having a total of 2 to 5 carbon atoms, wherein the alkyl moiety is the alkoxy group may be substituted by a phenyl group, and the Y group of the formula is enantioselectively reduced and, if necessary, hydrolyzed by the compound thus obtained, or e) oxidizes the (S) compound, of the general formula wherein W "represents a group which is by oxidation translates into a carboxy group, or f) separates a mixture consisting of any amount of (S) -enan-thiomer, of general formula II) and any amount of (R) -enantiomer, of general formula in which W 'represents carboxy - a group or alkoxycarbonyl group having a total of 2 to 5 carbon atoms, wherein the alkyl moiety of the alkoxy group may be substituted with a phenyl group, and the compound thus obtained is converted, if necessary, to a compound with higher enantiomeric purity, whereby crystallization from ethanol / water (2/1) gives a high melting point, 130 to 131V ° C, and crystallization from petroleum ether / tolulol (5/3) a low melting point, 99 to 101V And the compound thus obtained is converted to its salts, especially to its physiologically acceptable salts, with inorganic or organic acids or bases. The application contains 3 more dependent requests.

YU113691A 1991-06-28 1991-06-28 (S) - (+) - 2-ETHOXY-4- / N- (1- (2-PIPERIDINO-PHENYL) -3-METHYL-1-BUTYL-AMINOCARBONYL-METHYL-benzoic acid and procedures for its preparation YU48052B (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
SI9111136A SI9111136A (en) 1991-06-28 1991-06-28 (S)-(+)-2-ethoxy-4-/N-/1-(2-piperidino-phenyl)-3-methyl-1-butyl/ aminocarbonylmethyl/-benzoic acid, pharmaceuticals containing this compaund and processes for their preparation
YU113691A YU48052B (en) 1991-06-28 1991-06-28 (S) - (+) - 2-ETHOXY-4- / N- (1- (2-PIPERIDINO-PHENYL) -3-METHYL-1-BUTYL-AMINOCARBONYL-METHYL-benzoic acid and procedures for its preparation
HR940769A HRP940769B1 (en) 1991-06-28 1994-10-25 (s)(+)-2-ethoxy-4-(n-(1-(2-piperidinophenyl)-3-methyl-1-butyl)-aminocarbonylmethyl)benzoic acid, medicines containing them, that compound and processes for the preparation thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
YU113691A YU48052B (en) 1991-06-28 1991-06-28 (S) - (+) - 2-ETHOXY-4- / N- (1- (2-PIPERIDINO-PHENYL) -3-METHYL-1-BUTYL-AMINOCARBONYL-METHYL-benzoic acid and procedures for its preparation

Publications (2)

Publication Number Publication Date
YU113691A YU113691A (en) 1994-06-10
YU48052B true YU48052B (en) 1996-10-18

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
YU113691A YU48052B (en) 1991-06-28 1991-06-28 (S) - (+) - 2-ETHOXY-4- / N- (1- (2-PIPERIDINO-PHENYL) -3-METHYL-1-BUTYL-AMINOCARBONYL-METHYL-benzoic acid and procedures for its preparation

Country Status (2)

Country Link
SI (1) SI9111136A (en)
YU (1) YU48052B (en)

Also Published As

Publication number Publication date
SI9111136A (en) 1995-04-30
YU113691A (en) 1994-06-10

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