- Method for synthesizing cefdinir
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The invention relates to a method for synthesizing cefdinir. The method includes carrying out condensation reaction on cefdinir parent nuclei 7-AVCA and cefdinir side-chain active ester to obtain cefdinir with protecting groups; adding hydrogen chloride and catalysts into reaction liquid without separation on the reaction liquid and removing the protecting groups to obtain the cefdinir. The cefdinir parent nuclei 7-AVCA are used as raw materials. The method has the advantages that reaction for removing the protecting groups is directly carried out without separation on an intermediate product (the cefdinir with the protecting groups), accordingly, the cefdinir can be obtained under high-yield conditions, the yield can reach 85% at least, the method is short in synthetic reaction process route, and reagents are inexpensive and are low in cost.
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Paragraph 0033; 0034; 0035
(2017/05/16)
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- Method for preparing cefdinir
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The invention relates to a method for preparing cefdinir. The method includes condensing active ester of methoxyiminoacetic acid and 7.amino.3.vinyl.3.cephalosporin ring.4.carboxylate ester in the presence of organic alkali; carrying out ester hydrolysis reaction. The method has the advantages of few reaction steps, high yield and simplicity in post-treatment.
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Paragraph 0032; 0033; 0034; 0035; 0036; 0037; 0038
(2017/07/21)
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- Cefdinir synthesizing technology
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The invention provides a cefdinir synthesizing technology. The technology comprises the steps that (Z)-2-(2-aminothiazole-4-yl)-2-acetoxyl imino thioacetic acid(S-2-benzothiazole)ester and 7-amino-3-vinyl-8-oxo-5-thia-1-azabicyalo[4.2.0]oct-2-alkene-2-carboxylic acid are subjected to condensation; acetyl protection is removed through hydrolysis, and a cefdinir finished product is finally obtained. The method for preparing the cefdinir has the advantages of being short in production cycle, high in yield, high in product quality and suitable for industrial production.
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Paragraph 0055; 0062-0074; 0081-0093; 0100-0112; 0119-0131
(2017/06/02)
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- CRYSTALLINE HYDRATES OF CEFDINIR CALCIUM SALT
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Crystalline hydrates of (6R-(6α,7β(Z))-7-((2-amino-4-thiazolyl)(hydroxyimino)acetyl)amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (cefdinir), calcium salt, ways to make them, compositions comprising them and made with them, and methods of treatment using them are disclosed.
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Page/Page column 4
(2010/11/28)
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- Crystalline form of cefdinir cesium salt
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Provided is the cesium salt of cefdinir, processes for its preparation and its use in the preparation of cefdinir.
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Page/Page column 6
(2008/06/13)
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- Process for the preparation of cefdinir
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The invention relates to processes for preparing cefdinir via its potassium and cesium salts.
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Page/Page column 4
(2008/06/13)
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- CRYSTALLINE FORMS OF CEFDINIR POTASSIUM SALT
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The present invention encompasses the solid state chemistry of cefdinir potassium salt.
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Page/Page column 16
(2008/06/13)
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- Improved synthesis of Cefdinir and its polymorphic form, an antibacterial active pharmaceutical ingredient
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New methods for the preparation of Cefdinir 1 and its polymorphic form Sesqui hydrate 1a are described. The synthesis of 2-mercaptobenzothiazolyl (Z)-2-(2-amino-4-thiazolyl)-2-acetoxyiminoacetate 4 was affected by using triphenylphosphine and triethylamine, and acylation of 7-amino-3-vinylcephem-4- carboxylic acid 5 followed by deprotection with K2CO3 in the presence of ammonium chloride in the same pot yielded crude Cefdinir. Purification of crude Cefdinir through resin and treatment of the resulting wet product with trifluoroacetic acid gave highly pure TFA salt of Cefdinir 6, which on neutralization afforded 1a in excellent yield. The impurity profiling of this compound has also been discussed. Copyright Taylor & Francis Group, LLC.
- Rao, Korrapati V. V. Prasada,Dandala, Ramesh,Sivakumaran, Meenakshisunderam S.,Rani, Ananta,Naidu, Andra
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p. 2275 - 2283
(2008/02/07)
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- Novel compounds for the synthesis of Cefdinir
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(Chemical Equation Presented) Preparation of two new compounds 2-mercapto-5-methyl-1,3,4-thiadiazolyl-(Z)-2-(2-amino-4-thiazolyl) -2-trityloxyiminoacetate (14) and 2-mercapto-5-methyl-1, 3,4-thiadiazolyl- (Z)-2-(2-amino-4-thiazolyl)-2-acetyloxyiminoacetate (12) and their use in the preparation of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3- vinylcephem-4-carboxylic acid, also known by the generic name Cefdinir (1) has been accomplished in a single step by coupling with 7-amino-3-vinylcephem-4- carboxylic acid (7) with purity of greater than 99% by HPLC.
- Prasada Rao,Dandala, Ramesh,Sivakumaran, Meenakshisunderam,Rani, Ananta,Naidu
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p. 309 - 314
(2008/04/05)
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- A NOVEL CRYSTALLINE FORM OF CEFDINIR
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The present invention relates to a novel crystalline form of cefdinir, process for its preparation and to a pharmaceutical composition containing it. Thus, cefdinir is added to water at 20 - 25 °C and then hydrochloric acid (18 %) is added at 20 - 25 °C to get a clear solution. To the solution activated carbon is added at 20 - 25 °C, stirred for 30 minutes, filtered through hyflo bed and washed with water. Then the pH of the filtrate is adjusted to 6.5 with saturated bicarbonate solution at 5 - 8 °C, stirred for clear solution, activated carbon is added and stirred for 30 minutes at 5 - 8°C. The reaction mass is filtered through hyflo bed, washed with water, 1:1 sulfuric acid is dumped to the above solution at 5 - 8 °C (pH: 2.8) and then stirred for 60 minutes at 3 - 5 °C. The resulting solid is filtered, washed with water and dried at 40 °C under vacuum to give cefdinir form H.
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Page/Page column 5-6
(2008/06/13)
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- TERTIARY AMINE SALTS OF 2-(2-AMINOTHIAZOLE-4-YL)-2-ACYLOXYIMINO)ACETIC ACID
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Subject of the present invention are crystalline tertiary amine salts of 2-(2-aminothiazole-4-yl)-2-(acyloxyimino)acetic acid compounds of formula (I) wherein R1, R2 and R3 independently represents unsubstituted or substituted alkyl, cyclo-alkyl or aryl, and R4 denotes acyl, which may be obtained in anhydrous form. Crystalline compounds of formula I are useful in a reaction step with an activating agent in order to produce cefdinir. Additionally, a process to prepare compounds of formula I is a part of the present invention.
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Page/Page column 7
(2010/02/15)
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- ALKANOYL AMIDE SOLVATES OF 2-(2-AMINOTHIAZOLE-4-YL)-2-(ACYLOXYIMINO)ACETIC ACID
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Subject of the present invention are N,N-dimethyl alkanoyl amide solvates of 2-(2-aminothiazole -4-yl)-2(acyloxyimino)acetic acid compounds of formula (I) which may be prepared in an anhydrous form. Crystalline compounds of formula I are useful in a reaction step with an activating agent in order to produce cefdinir. Additionally, a process to prepare compounds of formula I is a part of the present invention.
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Page/Page column 7
(2010/02/15)
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- Stable amorphous Cefdinir
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The present invention relates to stable amorphous 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer), methods for its preparation, and pharmaceutical compositions comprising stable amorphous 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer).
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Page/Page column 2
(2010/02/15)
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- CRYSTALLINE FORM OF CEFDINIR AMMONIUM SALT AS AN INTERMEDIATE FOR THE PREPARATION OF PURE CEFDINIR
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The invention relates to crystalline Cefdinir ammonium salt of formula (I).
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Page/Page column 9; 10
(2008/06/13)
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- CRYSTALLINE FORMS OF CEFDINIR POTASSIUM
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The present invention relates to a novel crystalline potassium salt of cefdinir - cefdinir potassium tetrahydrate, processes for its preparation, pharmaceutical compositions including cefdinir potassium tetrahydrate, and methods of treating bacterial infections using cefdinir potassium tetrahydrate. In addition, the present invention also relates to a mixture of cefdinir potassium dihydrate and cefdinir potassium tetrahydrate, processes for its preparation, pharmaceutical compositions including the mixture, and methods of treating bacterial infections using mixtures of cefdinir potassium dihydrate and cefdinir potassium tetrahydrate. Further it also relates to processes for preparing pure cefdinir and cefdinir potassium dihydrate from cefdinir potassium tetrahydrate.
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Page/Page column 10
(2008/06/13)
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- CRYSTALLINE FORMS OF CEFDINIR
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The invention relates to processes for the preparation of crystalline polymorphic forms of cefdinir of formula I. More particularly, it relates to the preparation of crystalline polymorphic forms of cefdinir designated as Forms B and C. The invention also relates to pharmaceutical compositions that include the polymorphic forms B and C, and the use of the compositions for treating bacterial infections.
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Page/Page column 9-10
(2008/06/13)
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- NOVEL ORAL PHARMACEUTICAL SUSPENSION OF CEFDINIR CRYSTAL
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The present invention relates to a novel oral pharmaceutical suspension of cefdinir crystal. More specifically, the present invention relates to a novel kit for preparation of an oral pharmaceutical suspension containing crystal form C Cefdinir.
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Page/Page column 8
(2008/06/13)
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- PROCESS FOR THE PREPARATION OF CEFDINIR
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Provided are intermediates for use in synthesis of Cefdinir and processes for preparing cefdinir with such intermediates.
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Page/Page column 10
(2008/06/13)
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- STABLE AMORPHOUS CEFDINIR
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The present invention relates to stable amorphous 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer), methods for its preparation, and pharmaceutical compositions comprising stable amorphous 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer).
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Page/Page column 7
(2010/02/14)
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- NOVEL CRYSTAL OF 7- 2-(2-AMINOTHIAZOLE-4-YL)-2-HYDROXYIMINOA CETAMIDO-3-VINYL-3-CEPHEM-4-CARBOXYLIC ACID (SYN ISOMER) AND METHOD FOR PREPARATION THEREOF
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A novel crystal (B-type crystal) of 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide-3-vinyl-3-cephem-4-carboxylic acid (a syn isomer), characterized in that it exhibits peaks at diffraction angles shown in the following Table 1, in its powder X ray diffraction pattern: This crystal is obtained by forming a crystal from a solution at a temperature of -5 to 5°C in an acidic state. The crystal is not bulky, exhibits good stability and good filterability, and is excellent in the solubility toward water, and thus can be prepared with case.
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Page/Page column 12-13
(2010/02/15)
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- Stable bioavailable crystalline form or cefdinir and a process for the preparation thereof
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The present invention relates to a stable and bioavailable crystalline form of a third generation cephalosporin antibiotic, cefdinir and a process for the preparation thereof. The present invention also relates to a pharmaceutical composition containing the novel crystalline cefdinir, useful in the treatment of maladies such as bacterial infections.
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Page/Page column 15
(2010/02/14)
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- Cefdinir pyridine salt
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The present invention relates to a novel pyridine salt of 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer), methods for its preparation, and pharmaceutical compositions comprising the salt.
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Page/Page column 2
(2008/06/13)
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- NOVEL POLYMORPH OF CEFDINIR
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The present invention relates to novel polymorph of cefdinir represented by formula (I). More particularly, the present invention relates to novel crystalline form (Crystal D) of cefdinir. The present invention also provides a process for the preparation of novel crystalline form (Crystal D) of cefdinir.
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Page/Page column 11
(2010/02/14)
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- Novel polymorph of cefdinir
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The present invention relates to novel polymorph of cefdinir represented by formula (I). More particularly, the present invention relates to novel crystalline form (Crystal D) of cefdinir. The present invention also provides a process for the preparation of novel crystalline form (Crystal D) of cefdinir.
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Page/Page column 2; 4
(2010/02/14)
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- Novel crystalline form of cefdinir
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The present invention relates to novel crystalline form of Cefdinir, 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid, herein referred as cefdinir crystal B, processes for preparing cefdinir crystal B, and the incorporation of cefdinir crystal B in pharmaceutical compositions.
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- Polymorph of a pharmaceutical
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The present invention relates to novel crystalline polymorphs of 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamide]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer), methods for their preparation, and pharmaceutical compositions comprising the novel crystalline polymorphs.
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Page/Page column 4
(2008/06/13)
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- CRYSTALLINE CEFDINIR SALTS
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Cefdinir crystalline salts of formula (I), in which n ranges from 1 to 3, the preparation and use thereof for the preparation and purification of cefdinir is herein disclosed. The salts of formula (I) can be obtained from cefdinir intermediates or crude cefdinir by treatment with phosphoric acid.
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- CRYSTALLINE FORM OF CEFDINIR
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The invention relates to a new crystalline form of cefdinir and processes for producing the crystalline cefdinir. More particularly, it relates to the preparation of new crystalline form of cefdinir, referred to as 'Form R' and pharmaceutical compositions that include the 'Form R'. It also relates to a method of treatment of infectious diseases comprising administration of the 'Form R'.
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- NOVEL INTERMEDIATES FOR SYNTHESIS OF CEPHALOSPORINS AND PROCESS FOR PREPARATION OF SUCH INTERMEDIATES
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A novel 4-halo-2-oxyimino-3-oxo butyric acid-N, N-dimethyl formiminium chloride chlorosulfate of formula (I) useful in the preparation of cephalosporin antibiotics, wherein X is chlorine or bromine; R is hydrogen, C1-4 alkyl group, an easily removable hydroxyl protective group, -CH2COOR5, or -C(CH3)2COOR5, wherein R5 is hydrogen or an easily hydrolysable ester group. The compound of formula (I) is prepared by reacting 4-halo-2-oxyimino-3-oxobutyric acid of formula (IV1), wherein X, R and R5 are as defined above, with N, N-dimethylformiminium chloride chlorosulphate of formula (VII), in an organic solvent at a temperature ranging from -30 °C to -15 °C. The cephalosporins that may be prepared from the intermediate include cefdinir, cefditoren pivoxil, cefepime, cefetamet pivoxil, cefixime, cefmenoxime, cefodizime, cefoselis, cefotaxime, cefpirome, cefpodoxime proxetil, cefquinome, ceftazidime, cefteram pivoxil, ceftiofur, ceftizoxime, ceftriaxone and cefuzonam.
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- An alternative procedure for preparation of cefdinir
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Cefdinir, a broad spectrum third-generation cephalosporin for oral administration, was prepared by the following synthetic pathway: synthesis of diphenylmethyl 7β-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride from 7-aminocephalosporanic acid (7-ACA), preparation of sodium 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino) acetate from ethyl acetoacetate, coupling of both intermediaries to obtain diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-tritylhydroxyimino-3- vinyl-3-cephem-4-carboxylate and final cleavage of trityl and diphenylmethyl protective groups. This procedure allows to obtain better yields of cefdinir and to avoid the use of diketene during the synthesis of this antibiotic by the previously reported method.
- Gonzalez, Maritza,Rodriguez, Zalua,Tolon, Blanca,Rodriguez, Juan C.,Velez, Herman,Valdes, Barbara,Lopez, Miguel A.,Fini, Adamo
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p. 409 - 418
(2007/10/03)
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- Crystalline amine salt of cefdinir
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Cefdinir in the form of a salt with dicyclohexylamine, a process for its production and its use in the purification of impure cefdinir.
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Page column 3
(2008/06/13)
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