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1. (WO1998052918) INTERMEDIATES USEFUL IN PRODUCING CARBAPENEM AND PROCESS FOR THE STEREOSELECTIVE PRODUCTION OF THE SAME
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1998/052918 International Application No.: PCT/JP1998/002225
Publication Date: 26.11.1998 International Filing Date: 21.05.1998
Chapter 2 Demand Filed: 20.11.1998
IPC:
C07D 207/12 (2006.01) ,C07D 263/22 (2006.01) ,C07D 413/06 (2006.01) ,C07D 477/20 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
207
Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
02
with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
04
having no double bonds between ring members or between ring members and non-ring members
10
with 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
12
Oxygen or sulfur atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
263
Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
02
not condensed with other rings
08
having one double bond between ring members or between a ring member and a non-ring member
16
with 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
18
Oxygen atoms
20
attached in position 2
22
with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
413
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
02
containing two hetero rings
06
linked by a carbon chain containing only aliphatic carbon atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
477
Heterocyclic compounds containing 1-azabicyclo [3.2.0] 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
10
with 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
12
with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
16
with hetero atoms or carbon atoms 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 3
20
Sulfur atoms
Applicants:
EISAI CO., LTD. [JP/JP]; 6-10, Koishikawa 4-chome Bunkyo-ku Tokyo 112-8088, JP (AllExceptUS)
SUZUKI, Takaaki [JP/JP]; JP (UsOnly)
SUGIYAMA, Isao [JP/JP]; JP (UsOnly)
SASHO, Manabu [JP/JP]; JP (UsOnly)
SATO, Nobuaki [JP/JP]; JP (UsOnly)
KAMADA, Atsushi [JP/JP]; JP (UsOnly)
ASHIZAWA, Kazuhide [JP/JP]; JP (UsOnly)
Inventors:
SUZUKI, Takaaki; JP
SUGIYAMA, Isao; JP
SASHO, Manabu; JP
SATO, Nobuaki; JP
KAMADA, Atsushi; JP
ASHIZAWA, Kazuhide; JP
Agent:
FURUYA, Kaoru ; Nihonbashi TM Building 1-8-11, Nihonbashi-Horidomecho Chuo-ku Tokyo 103-0012, JP
Priority Data:
9/13317123.05.1997JP
Title (EN) INTERMEDIATES USEFUL IN PRODUCING CARBAPENEM AND PROCESS FOR THE STEREOSELECTIVE PRODUCTION OF THE SAME
(FR) INTERMEDIAIRES EMPLOYES A LA PRODUCTION DE CARBAPENEM ET PROCEDE DE PRODUCTION STEREOSELECTIVE
Abstract:
(EN) An efficient process for the stereoselective production of (2S,4S)-2-[[(R)-hydroxy-(3R)-cyclic amin-3-yl]methyl]pyrrolidine-4-thiol or its salts, which are intermediates useful in producing carbapenem, by reacting a compound represented by general formula (I) (wherein R1 represents lower alkylsulfonyl, optionally substituted arylsulfonyl or alkylsilyl; and R2 represents an amino-protective group) with a compound represented by general formula (II), wherein R3 represents optionally substituted lower alkyl or aryl; X represents oxygen or sulfur; Y represents azido or nitro; and m is an integer of from 2 to 5.
(FR) L'invention a trait à un procédé efficace de production stéréosélective de (2S,4S)-2-[[(R)-hydroxy-(3R)-amine cyclique-3-yl]méthyl]pyrrolidine-4-thiol ou de ses sels, en l'occurrence des intermédiaires employés à la production de carbapenem. Le procédé consiste à faire réagir un composé représenté par la formule générale suivante (I) (formule dans laquelle R1 représente un alkylsulfonyle inférieur, un arylsulfonyle ou un alkylsilyle éventuellement substitué et où R2 représente un groupe amino-protecteur) avec un composé représenté par la formule générale suivante (II), dans laquelle R3 représente un alkyle ou un aryle éventuellement substitué, X représente un oxygène ou un soufre et où Y représente un azido ou un nitro, m étant un nombre entier d'une valeur comprise entre 2 et 5.
front page image
Designated States: US
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
Publication Language: Japanese (JA)
Filing Language: Japanese (JA)
Also published as:
EP1020440US6218550US6372914