- Drug intermediate in ACE- inhibitor synthesis and application thereof
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Compound (I) of Formula, wherein R1 is aryl or alkyl ;R2 represents alkyl ;R3 represents alkyl or aralkyl, is a valuable pharmacological intermediate, which may be prepared by reacting a compound of Formula (IV) above (with thionyl chloride as defined above R1 in particular by reacting a compound of Formula R2 with thionyl chloride), especially for use in the preparation, inhibitor, such as for example for (VI) eperindopril or ramipril 2. ((I). The compound X of Formula . R3 is as defined (I) above). wherein (II) and (are defined above ACE. R1 and R2 wherein R is. a compound, of formula,).
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Paragraph 0014
(2020/03/17)
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- A METHOD FOR PREPARING RAMIPRIL
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Enantio-specific synthesis of optically pure (2S)-acetylamino-3-(2-oxo-cyclopentyl)- propionic acid (I) comprising converting enantiomeric mixture of (1 -4C alkyl)-2- acetylamino-3-(2-oxocyclopentyl) propionoate (II) (+ and -) under the influence of an Alkaline serine endopeptidase is disclosed. The invention further describes use of optically pure (2S)-acetylamino-3-(2-oxocyclopentyl)-propionic acid (I) formed by the process of present invention, in the preparation of Ramipril.
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Paragraph 0042
(2015/04/15)
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- PROCESS FOR THE PREPARATION OF RAMIPRIL
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An enantioselective process for the production of (2S,3aS,6aS)-cyclopenta[b]pyrrole-2-carboxylic acid and its conversion into Ramipril is provided.
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Page/Page column 52
(2016/01/01)
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- COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE
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To characterize the urinary exosome miRNome, microarrays were used to identify the miRNA spectrum present within urinary exosomes from ten individuals that were previously classified for their salt sensitivity status. The present application discloses distinct patterns of selected exosomal miRNA expression that were different between salt-sensitive (SS), salt-resistant (SR), and inverse salt-sensitive (ISS) individuals. These miRNAs can be useful as biomarkers either individually or as panels comprising multiple miRNAs. The present invention provides compositions and methods for identifying, diagnosing, monitoring, and treating subjects with salt sensitivity of blood pressure. The applications discloses panels of miRNAs useful for comparing profiles, and in some cases one or more of the miRNAs in a panel can be used. The miRNAs useful for distinguishing SS and SR or ISS and SR subjects. One or more of the 45 miRNAs can be used. Some of the miRNAs have not been previously reported to be circulating. See those miRNAs with asterisks in FIG. 1 and below. The present invention encompasses the use of one or more of these markers for identifying and diagnosing SR, SS, and ISS subjects.
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- PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE
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A process for the production of amides of N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine is described. The process can be used for the production of key intermediates and finally the ACE inhibitors such as Ramipril, Enalapril, Quinapril, Trandolapril, Delapril and Moexipril starting from N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine by the reaction with the appropriate amines.
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Page/Page column 20
(2015/01/07)
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- METHOD FOR THE SYNTHESIS OF A RAMIPRIL INTERMEDIATE
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The present invention relates to a process for the preparation of octahydrocyclopenta[b]pyrrole-2-carboxylic acid and esters thereof of general formula (1) in the presence of a cobalt and/or nickel comprising catalyst and to the use of compounds of general formula (1) in the synthesis of ramipril.
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Page/Page column 12-13
(2010/05/14)
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- A PROCESS FOR PREPARATION OF RAMIPRIL
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Disclosed herein is a process for preparation of Ramipril; which comprises; reacting salts of (S,S,S)-azabicyclo[3.3.0]-octane-3-carboxylate with N-[l-(S)-ethoxy carbonyl)-3- phenyl propyl] -L-alanine in presence of dicyclohexylcarbodimide (DCC) and 1- hydroxybenzotriazole (HOBT) in a suitable solvent medium.
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Page/Page column 13-14
(2009/10/30)
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- METHOD FOR THE PRODUCTION OF RAMIPRIL
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An improved method for preparing ramipril is disclosed, and also an intermediate for use in the method.
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Page/Page column 6
(2009/01/24)
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- NOVEL CARBAMOYLGLYCINE DERIVATIVES
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The present invention relates to carbamoylglycine derivatives, a process for the preparation of carbamoylglycine derivatives and the use of carbamoylglycine derivatives in the preparation of enantiomerically enriched α-amino acids. Furthermore, the present invention relates to the preparation of pharmaceutically active products such as perindopril and ramipril using the novel carbamoylglycine derivatives.
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Page/Page column 14-15
(2009/05/28)
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- NOVEL CYCLOALKANONE β-SUBSTITUTED ALANINE DERIVATIVES
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The present invention relates to cycloalkanone β-substituted alanine derivatives, a process for the preparation of cycloalkanone β-substituted alanine derivatives and the use of cycloalkanone β-substituted alanine derivatives in the preparation of enantiomerically enriched α-amino acids. Furthermore, the present invention relates to the preparation of pharmaceutically active products such as perindopril and ramipril using the novel cycloalkanone β-substituted alanine derivatives.
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Page/Page column 9
(2009/10/09)
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- IMPROVED RAMIPRIL SYNTHESIS
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The present invention relates to the preparation of ramipril (formula [1]) from unprotected (2S,3S,6S)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid and to a method for preparing unprotected (2S,3S,6S)-octahydrocyclopenta[b]pyrrole-2- carboxylic acid.
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Page/Page column 8
(2009/06/27)
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- Expeditious synthesis of ramipril: An angiotensin converting enzyme (ACE) inhibitor
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We document an efficient and cost-effective synthesis of ramipril 1 utilizing (i) an environmentally benign process for the esterification of racemic 2-aza-bicyclo-[3.3.0]-octane-3-carboxylic acid hydrochloride 2 using boric acid as a catalyst and (ii) a robust resolution process for the synthesis of 3a by means of inexpensive and recyclable L-(+)-mandelic acid as key steps. Copyright Taylor & Francis Group, LLC.
- Malakondaiah, Golla China,Gurav,Reddy, Lekkala Amarnath,Babu, Karrothu Srihari,Bhaskar, Bolugoddu Vijaya,Reddy, Padi Pratap,Bhattacharya, Apurba,Anand, Ramasamy Vijaya
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p. 1737 - 1744
(2008/09/21)
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- NOVEL 5-SUBSTITUTED HYDANTOINS
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The present invention relates to 5-substituted hydantoins, a process for the preparation of 5-substituted hydantoins and the use of 5-substituted hydantoins in the preparation of enantiomerically enriched α-amino acids. Furthermore, the present invention relates to the preparation of pharmaceutically active products such as perindopril and ramipril using the novel 5-substituted hydantoins.
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Page/Page column 19
(2009/01/24)
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- PREPARATION OF RAMIPRIL AND STABLE PHARMACEUTICAL COMPOSITIONS
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A process for preparing ramipril, and stable pharmaceutical compositions containing ramipril.
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Page/Page column 12
(2010/11/28)
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- A PROCESS FOR THE PREPARATION OF 2-[N-- [(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-(S)-ALANYL]-(1S, 3S, 5S) -2-AZABICYCLO [3.3.0] OCTANE-3--CARBOXYLIC ACID
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A process for preparation of 2-[N-[(S)-l--ethoxycarbonyl-3-phenylpropyl] - (S) -alanyl]-(1S, 3S, 5S)-2-- azabicyclo [3.3.0 ] octane-3-carboxylic acid, ie. Ramipril, involves condensation of an activated derivative of 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine with racemic (1R*, 3R*, 5R*) -2-azabicyclo [3.3.0] octane-3--carboxylic acid, and then the desired diastereoisomer (la) is separated from the obtained diastereoisomeric mixture of 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-(S) -alanyl] - (1S, 3S, 5S) -2-azabicyclo [3.3.0] octane-3--carboxylic acid (1a) and 2- [N-[(S)-1-ethoxycarbonyl-3--phenylpropyl ] - (S) -alanyl ] - (1R, 3R, 5R) -2- azabicyclo[3.3.0]octane-3-carboxyl ic acid (lb) by treat-ing it with a solvent that selectively dissolves the un-desired diastereoisomer (1b) while the diastereoisomer (1a) remains undissolved.
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Page/Page column 12
(2008/06/13)
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- A METHOD OF PREPARATION OF RAMIPRIL
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A method of preparation of ramipril of formula (I), during which the benzyl ester hydrochloride of formula (III) is converted to the benzyl ester of formula (II), which in turn affords, by reaction with the carboxyanhydride of formula (V), the benzyl ester of ramipril of formula (IV), which is subsequently converted to ramipril of formula (I).
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Page/Page column 6
(2008/06/13)
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- 2′-Benzothiazolylthioesters of N-substituted alpha amino acids: Versatile intermediates for synthesis of ACE inhibitors
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ACE inhibitors have been synthesized from novel active esters using simple reaction conditions in high diastereomeric selectivity. The active esters may be obtained from the corresponding carboxylic acids or their acid chlorides.
- Singh, Girij Pal,Godbole, Himanshu M.,Nehate, Sagar P.,Mahajan, Pravin R.
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p. 243 - 248
(2007/10/03)
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- PROCESS FOR CRYSTALLIZATION OF RAMIPRIL AND PREPARATION OF A HYDRATED FORM THEREOF
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The present invention relates to a novel method for obtaining (2S,3aS,6aS)-1-[(S)-2-[[(S)-1-(ethoxycarbonyl)-3-phenylpropyl]-amino] propanoyl] octahydro cyclopenta[b] pyrrole-2-carboxylic acid, viz. Ramipril(I) in high optical purity, free of other stereoisomers, and in high bulk density. The present invention also relates to a novel hydrated form of Ramipril(I) and a process for preparation thereof.
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Page/Page column 11-14
(2010/02/13)
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- USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS
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The present invention relates to the use of a substituted 2-phenylbenzimidazole of formula I wherein R1, R2, R3, R 4, R5 and m have the meanings given in the claims, for the preparation of a medicament for the treatment or prevention of diseases involving glucagon receptors, as well as new compounds of formula I wherein R1 is a group of formula
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- Synthesis of a highly active angiotensin converting enzyme inhibitor: 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2-azabicyc lo[3.3.0]octane-3-carboxylic acid (Hoe 498)
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The convergent, diastereoselective synthesis of 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2-azabicyc lo[3.3.0]octane-3-carboxylic acid (Hoe 498), a new ACE-inhibitor with improved bioavailability and pharmacokinetics, is described.
- Teetz,Geiger,Henning,Urbach
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p. 1399 - 1401
(2007/10/02)
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