- METHOD FOR PREPARING MEROPENEM USING ZINC POWDER
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The present invention relates to an improved method for synthesizing meropenem trihydrate [(1R,5S,6S)-2-[((2′S,4′S)-2′-dimethylaminocarbozyl)pyrrolidin-4′-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid, trihydrate], which is a novel carbapenem antibiotic.
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Page/Page column 5
(2012/03/27)
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- IMPROVED METHOD FOR PREPARING MEROPENEM USING ZINC POWDER
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The present invention relates to an improved method for synthesizing meropenem trihydrate [(1R,5S,6S)-2-[((2'S,4'S)-2'-dimethylaminocarbozyl)pyrrolidin-4'-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid, trihydrate], which is a novel carbapenem antibiotic.
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Page/Page column 7
(2012/02/04)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF MEROPENEM
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The present invention provides an improved process for the preparation of methyl carbapenem derivative of formula (I) or its pharmaceutically acceptable salts or hydrates thereof in a pure form.
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- Improved process for the preparation of carbapenem using carbapenem intermediates and recovery of carbapenem
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The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem; and provides an effective process for recovering ertapenem compounds.
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Page/Page column 12
(2011/12/03)
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- Preparation of Carbapenem Intermediate and Their Use
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The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem.
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Page/Page column 7
(2011/12/12)
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- Process for The Preparation of Beta-Lactam Antibiotic
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The present invention relates to a process for the preparation of Meropenem of formula (I) in sterile form and also provides an improved process for the preparation of compound of formula (V), which is an important intermediate in the synthesis of Meropenem.
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Page/Page column 5
(2009/10/30)
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- MEROPENEM INTERMEDIATE IN NOVEL CRYSTALLINE FORM AND A METHOD OF MANUFACTURE OF MEROPENEM
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The present invention specially relates to the crystalline form of (4-Nitrobenzyl (4R,5S,6S)-(3-{(3S,5S)-5-[(dimethylamino)carbonyl]-1-[(4-nitrophenoxy)carbonxyl]pyrrolidin-3-yl}thio-6-[(1R)-1-hydorxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0].hept-2-ene-2-carboxylate) of compound Formula I as well as an improved process for preparation of meropenem trihydrate of compound Formula II wherein PNB represents a P-nitro benzyl group and PNZ represents a P-nitrobenzyloxycarbonyl group.
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Page/Page column 5
(2009/12/23)
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- IMPROVED PROCESS FOR PRODUCING CARBAPENEM COMPOUND
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The present invention has its object to provide an easy process for producing (4R,5S,6S)-3-[[(3S,5S)-5-(dimethylaminocarbonyl)-3-pyrrolid inyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicy clo[3.2.0]hept-2-ene-2-carboxylic acid, excellent in antimicrobial activity. The present invention relates to a process for continuously producing (4R,5S,6S)-3-[[(3S,5S)-5-(dimethylaminocarbonyl)-3-pyrrolid inyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicy clo[3.2.0]hept-2-ene-2-carboxylic acid without isolating/purifying the reaction intermediate.
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Page/Page column 13-14
(2009/01/24)
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- A PROCESS FOR THE PREPARATION OF MEROPENEM
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The invention relates to a process for the preparation of meropenem, a β-methylcarbopenem. The said process comprises the following steps: preparing the compound of Formula (XI) from the compound of Formula (IV) through three steps "one-pot process"; then condensing the compound of Formula (XI) with the compound of Formula (XX) to form the compound of Formula (XXIV); finally preparing meropenam of Formula (I) from the compound of Formula (XXIV) by deprotection reaction by means of catalyst. The process of the invention is easily to carry out, the product is isolated in high content and yield, and the cost is reduced, thereby overcoming the shortage of the prior art.
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Page/Page column 13-14
(2010/11/28)
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- PROCESSES FOR THE PREPARATION OF CARBAPENEMS
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The invention relates to processes for the preparation of carbapenems. More particularly, it relates to a process for the preparation of meropenem.
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Page/Page column 5-6
(2010/11/28)
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- A PROCESS FOR THE PREPARATION OF THE INTERMEDIATE OF Β-METHYL CARBAPENEM
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A process of preparation of the intermediate of β-methyl carbapenem is disclosed, in which 4-acetylazacyclobutanone as the raw material is firstly reacted with α-bromopropionamide having a big inductive group. Since this reaction is highly stereoselectivity, most of the product is the required parent nucleus of β-methyl carbapenem, a product of β-configuration. Compared with the prior art, the process of the present invention is highly-yielding, cost-effective and can be used for large scale production.
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Page/Page column 18
(2010/11/28)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF BETA-LACTAM ANTIBIOTIC
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The present invention relates to a process for the preparation of Meropenem of formula (I) in sterile form and also provides an improved process for the preparation of compound of formula (V), which is an important intermediate in the synthesis of Meropenem.
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Page/Page column 13-17
(2008/06/13)
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- Carbapenems, their preparation and use the synthesis of carbapenems
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Pyrrolidine compound (V), in free or salt form, is new. Pyrrolidine compound of formula (V), in free or salt form, is new. Independent claims aren also included for: (1) the preparation of (V); (2) the preparation of 3-[(3S,5S)-5-carbamido-3-pyrrolidinyl]-thio substituted carbapenem compound of formula (II) comprising reaction of (V) with an amine compound of formula (NH(R1)(R2)) to give a pyrrolidine compound of formula (III); and elimination of p-nitrobenzyl- and/or p-nitrobenzylcarbonyl-protection groups from (III); and (3) preparation of a pharmaceutical composition of (II) comprising mixing (II) with solvents or auxiliary materials. Either R1, R2alkyl, H, aryl or heterocyclyl; or NR1R25-8 membered optionally saturated heterocyclic group (optionally substituted). [Image] [Image].
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Page/Page column 8-9
(2008/06/13)
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- MEROPENEM INTERMEDIATE IN CRYSTALLINE FORM
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The present invention relates to the compound (4R, 5S, 6S)-(p-nitrobenzyl) 3-[[(3S, 5S)-1(-p-nitrobenzyloxycarbonyl)-5-(dimethylaminocarbonyl)-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2carboxylate in crystalline form, as well as a process for the production of this crystalline compound in alkyl alkanoates, and its usage in a process for producing meropenem. Formula (I).
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Page/Page column 6-7
(2008/06/13)
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- Azetidinone compounds useful in the preparation of carbapenem antibiotics and process for preparing carbapenem and penem compounds
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Compounds of formula (I): STR1 wherein: R1 is hydrogen or a hydroxy-protecting group; R2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR5 R6, where Y is oxygen or sulfur, and R5 and R6 are each alkyl, aryl or aralkyl, or R5 and R6 and the nitrogen to which they are attached together form a heterocyclic group; is R4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.
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- An Efficient Synthesis of (2S,4S)-2-Substituted-4-mercaptopyrrolidine Derivatives
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An efficient synthesis of (2S,4S)-2-substituted 4-mercapto-1-p-nitrobenzyloxycarbonylpyrrolidine (2) was studied.Intramolecular cyclization of (2S,4R)-1-p-nitrobenzyloxycarbonyl-4-methanesulfonyloxy-2-pyrrolidinethiocarboxylic acid (8), derived from trans-4-hydroxy-L-proline (3), afforded (1S,4S)-5-p-nitrobenzyloxycarbonyl-2-thia-5-azabicycloheptan-3-one (7).Reaction of 7 with primary amine, secondary amine and alkoxide afforded corresponding 2 in high yield.
- Matsumura, Haruki,Bando, Takashi,Sunagawa, Makoto
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p. 147 - 160
(2007/10/02)
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- Process for preparing carbapenem and penem compounds and new compounds involved in that process
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Penem and carbapenem compounds having a group of formula -SA are prepared from a corresponding compound having a substituted thio, sulphinyl or sulphonyl group at this position by reaction with a compound ASH (where A is various organic groups) in the presence of a salt of a metal of Group II or III of the Periodic Table.
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- Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton
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An efficient synthesis of 1β-methylcarbapenem from the 1-(2- oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.
- Sunagawa,Sasaki,Matsumura,Goda,Tamoto
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p. 1381 - 1387
(2007/10/02)
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