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1. WO1996004286 - PROCESS FOR MAKING QUINOLONYL LACTAM ANTIMICROBIALS AND NOVEL INTERMEDIATE COMPOUNDS

Publication Number WO/1996/004286
Publication Date 15.02.1996
International Application No. PCT/US1995/009649
International Filing Date 01.08.1995
Chapter 2 Demand Filed 23.02.1996
IPC
C07D 215/56 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
215Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
16with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
54attached in position 3
56with oxygen atoms in position 4
C07D 463/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
463Heterocyclic compounds containing 1-azabicyclo octane ring systems, i.e. compounds containing a ring system of the formula: , e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
C07D 477/14 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
477Heterocyclic compounds containing 1-azabicyclo heptane ring systems, i.e. compounds containing a ring system of the formula: , e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
10with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
12with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
14with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3
C07D 499/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
499Heterocyclic compounds containing 4-thia-1-azabicyclo heptane ring systems, i.e. compounds containing a ring system of the formula: , e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
C07D 499/88 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
499Heterocyclic compounds containing 4-thia-1-azabicyclo heptane ring systems, i.e. compounds containing a ring system of the formula: , e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
88Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
C07D 501/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
501Heterocyclic compounds containing 5-thia-1-azabicyclo octane ring systems, i.e. compounds containing a ring system of the formula: , e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
CPC
A61P 31/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
31Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
C07D 215/56
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
215Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
02having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
16with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
54attached in position 3
56with oxygen atoms in position 4
C07D 463/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
463Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula: , e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
02Preparation
04by forming the ring or condensed ring systems
C07D 477/14
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
477Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: , carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
10with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4 and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
12with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
14with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3
C07D 499/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
499Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: , e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
C07D 499/88
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
499Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula: , e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
88Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
Applicants
  • THE PROCTER & GAMBLE COMPANY [US]/[US]
Inventors
  • RANDALL, Jared, Lynn
  • GODLEWSKI, Jane, Ellen
Agents
  • REED, T., David
Priority Data
08/284,77102.08.1994US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) PROCESS FOR MAKING QUINOLONYL LACTAM ANTIMICROBIALS AND NOVEL INTERMEDIATE COMPOUNDS
(FR) PROCEDE D'OBTENTION D'ANTIMICROBIENS A BASE DE QUINOLONYLE LACTAME ET NOUVEAUX COMPOSES INTERMEDIAIRES
Abstract
(EN)
The present invention provides processes for making compounds of the structure (Q-L1)-L-(L2-B), wherein (I) Q is a quinolone moiety; (II) B is a lactam moiety; and (III) L, L1, and L2 together comprise a linking moiety; comprising the steps of: (1) coupling a compound of formula (III) with a lactam-containing compound to form an intermediate compound; and (2) cyclizing the intermediate by reaction with an organosilicon compound to give a compound of the formula (Q-L1)-L-(L2-B). Preferably, the process additionally comprises a step prior to the coupling step, wherein protected forms of the compound of formula (III) and the lactam compound are formed; and deprotection steps after the cyclization step, wherein the protecting groups are removed. Preferred antimicrobial compounds made by these processes are those where the beta-lactam moiety is a penem, a carbapenem, a cephem, or a carbacephem. Also preferred are those compounds where L1, L, and L2 form a carbamate moiety, or a secondary or tertiary amine moiety. The present invention also provides novel intermediate compounds of the formula (M-L1)-L-(L2-B), where (I) M has a structure according to formula (IV), (II) B is a lactam moiety, and (III) L, L1, and L2 together comprise a linking moiety.
(FR)
L'invention porte sur un procédé d'obtention de composés de structure (Q - L1) - L - (L2 - B) où: (I) Q est une fraction de quinolone; (II) B est une fraction de lactame, et (III) L, L1, et L2 forment ensemble une fraction de liaison. Ledit procédé consiste: (1) à coupler un composé de formule (III) à un composé contenant du lactame pour former un composé intermédiaire, et (2) à cycliser le composé intermédiaire par réaction avec un composé d'organosilicium pour obtenir un composé de formule (Q - L1) - L - (L2 - B). Le procédé comporte en outre de préférence une étape préliminaire au cours de laquelle se forment des formes protégées du composé de formule (III) et le composé du lactame et des étapes de déprotection suivant l'étape de protection au cours desquelles les groupes de protection sont éliminés. Les composés antimicrobiens obtenus par ces procédés sont ceux dont la fraction de béta-lactame est un pénème, un carbapénème, un céphème ou un carbacéphème. Sont également préférés les composés dans lesquels L1, L et L3 forment ensemble une fraction de carbamate ou une fraction d'amine tertiaire ou secondaire. L'invention porte également sur de nouveaux composés intermédiaires de formule (M - L1) - L - (L2 - B) où (I) M présente une structure représentée par la formule (IV), (II) B est une fraction de lactame, et (III) L, L1, et L2 forment ensemble une fraction de liaison.
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