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1. (WO1998051677) PROCESS FOR SYNTHESIZING CARBAPENEM INTERMEDIATES
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1998/051677 International Application No.: PCT/US1998/009036
Publication Date: 19.11.1998 International Filing Date: 08.05.1998
Chapter 2 Demand Filed: 25.11.1998
IPC:
C07C 311/16 (2006.01) ,C07D 275/06 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
311
Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
15
Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
16
having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
275
Heterocyclic compounds containing 1, 2-thiazole or hydrogenated 1,2-thiazole rings
04
condensed with carbocyclic rings or ring systems
06
with hetero atoms directly attached to the ring sulfur atom
Applicants:
MERCK & CO., INC. [US/US]; 126 East Lincoln Avenue Rahway, NJ 07065, US (AllExceptUS)
HUMPHREY, Guy, R. [GB/US]; US (UsOnly)
MILLER, Ross, A. [US/US]; US (UsOnly)
LIEBERMAN, David, R. [US/US]; US (UsOnly)
Inventors:
HUMPHREY, Guy, R.; US
MILLER, Ross, A.; US
LIEBERMAN, David, R.; US
Agent:
MERCK & CO., INC.; 126 East Lincoln Avenue Rahway, NJ 07065, US
Common
Representative:
MERCK & CO., INC.; 126 East Lincoln Avenue Rahway, NJ 07065, US
Priority Data:
60/046,35713.05.1997US
9806023.920.03.1998GB
Title (EN) PROCESS FOR SYNTHESIZING CARBAPENEM INTERMEDIATES
(FR) PROCEDE DE SYNTHESE POUR COMPOSES INTERMEDIAIRES DE CARBAPENEM
Abstract:
(EN) A process for synthesizing a compound of formula (I) is disclosed wherein R represents halo or C1-6 alkyl, unsubstituted or substituted with OP, wherein P represents a protecting group, comprising: (a) reacting a compound of formula (II) with chlorosulfonic acid to produce a compound of formula (III), (b) reacting compound (III) with NHRaRb, wherein Ra and Rb represent H or C1-6 alkyl, to produce a compound of formula (IV), (c) reacting compound (IV) with HNO3 to produce a compound of formula (V), (d) reacting compound (V) with a reducing agent to produce a compound of formula (VI) and (e) reacting compound (VI) with acid to produce a compound of formula (I). Intermediate compounds that are useful in the synthesis of carbapenem side chains are included as well.
(FR) L'invention concerne un procédé de synthèse pour composé de formule I. Dans ladite formule, R est halo ou alkyle C1-6, non substitué ou substitué par OP, et P est un groupe de protection. Le procédé consiste à : (a) faire réagir un composé de formule II avec de l'acide chlorosulfonique pour obtenir un composé de formule III; (b) à faire réagir le composé III avec NHRaRb, Ra et Rb étant H ou alkyle C1-6, pour obtenir un composé de formule IV; (c) à faire réagir le composé IV avec HNO3 pour obtenir un composé de formule V; (d) à faire réagir le composé V avec un agent réducteur pour obtenir un composé de formule VI; et (e) à faire réagir le composé VI avec un acide pour obtenir un composé de formule I. L'invention concerne aussi des composés intermédiaires utiles dans la synthèse des chaînes latérales de carbapenem.
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Designated States: AL, AM, AU, AZ, BA, BB, BG, BR, BY, CA, CN, CU, CZ, EE, GE, GW, HU, ID, IL, IS, JP, KG, KR, KZ, LC, LK, LR, LT, LV, MD, MG, MK, MN, MX, NO, NZ, PL, RO, RU, SG, SI, SK, SL, TJ, TM, TR, TT, UA, US, UZ, VN, YU
African Regional Intellectual Property Organization (ARIPO) (GH, GM, KE, LS, MW, SD, SZ, UG, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
EP0981522JP2001527557 CA2287931AU1998073678