CA2417353A1 - Single-step process for preparing 7,16-deoxy-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15-hexamethylbicycle (11.2.1)hexadeca-1(2)-en-8-one, and obtaining a new form of 9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin a - Google Patents

Single-step process for preparing 7,16-deoxy-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15-hexamethylbicycle (11.2.1)hexadeca-1(2)-en-8-one, and obtaining a new form of 9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin a Download PDF

Info

Publication number
CA2417353A1
CA2417353A1 CA002417353A CA2417353A CA2417353A1 CA 2417353 A1 CA2417353 A1 CA 2417353A1 CA 002417353 A CA002417353 A CA 002417353A CA 2417353 A CA2417353 A CA 2417353A CA 2417353 A1 CA2417353 A1 CA 2417353A1
Authority
CA
Canada
Prior art keywords
aza
erythromycin
hexamethylbicycle
desosaminil
cladinosil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002417353A
Other languages
French (fr)
Other versions
CA2417353C (en
Inventor
Juan Antonio De La Torre Garcia
Fidencio Franco Andrade
Jose Manuel Francisco Lara Ochoa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Instituto de Investigacion en Quimica Aplicada SC
Laboratorios Silanes SA de CV
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2417353A1 publication Critical patent/CA2417353A1/en
Application granted granted Critical
Publication of CA2417353C publication Critical patent/CA2417353C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals

Abstract

The invention relates to an improved method for preparing 7,16-deoxy-2-aza-1 0- O-cladinosil-12-O-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15- hexamethylbicycle[11.2.1]hexa-deca-1(2)-en-8-ona from erythromycin A, wherei n said compound is obtained from erythromycin A with high yields and under sof t and adequate production conditions in a single-step process. Transformation of erythromycin A into an intermediate compound called 6,9-iminoether, which is obtained in a single step, is carried out by forming "in situ" mesitylenesulfonyloxime from erythromycin, which undergoes Beckmann's transposition in the presence of a base in aqueous acetone thus giving rise to the iminoether with the aid of the hydroxyl in position 6 of the macrolide ring. Said intermediate compound is transformed into the antibiotic called 9 - deoxo-9a-aza-9a-methyl-9a-homoerythromycin A, which is obtained by appropria te precipitation in hexane. A novel form with an anhydrous crystalline structur e and physical properties differing from those of forms known to date is thus obtained.
CA002417353A 2000-07-25 2000-07-25 Single-step process for preparing 7,16-deoxy-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15-hexamethylbicycle (11.2.1)hexadeca-1(2)-en-8-one, and obtaining a new form of 9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin a Expired - Fee Related CA2417353C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/MX2000/000030 WO2002010144A1 (en) 2000-07-25 2000-07-25 Single-step process for preparing 7,16-deoxy-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15-hexamethylbicycle (11.2.1)hexadeca-1(2)-en-8-ona and obtaining a new form of 9-desoxo-9a-methyl-9a-aza-9a-homoerythromycin a

Publications (2)

Publication Number Publication Date
CA2417353A1 true CA2417353A1 (en) 2003-01-27
CA2417353C CA2417353C (en) 2009-09-01

Family

ID=19741683

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002417353A Expired - Fee Related CA2417353C (en) 2000-07-25 2000-07-25 Single-step process for preparing 7,16-deoxy-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15-hexamethylbicycle (11.2.1)hexadeca-1(2)-en-8-one, and obtaining a new form of 9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin a

Country Status (8)

Country Link
US (1) US6528492B1 (en)
EP (1) EP1304326B1 (en)
AT (1) ATE320441T1 (en)
AU (1) AU2000270425A1 (en)
CA (1) CA2417353C (en)
DE (1) DE60026718T2 (en)
ES (1) ES2260047T3 (en)
WO (1) WO2002010144A1 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HRP20020231A2 (en) * 2002-03-18 2003-12-31 Pliva D D ISOSTRUCTURAL PSEUDOPOLYMORPHS OF 9-DEOXO-9a-AZA-9a-METHYL-9a-HOMOERYTHROMYCIN A
BR0209918A (en) * 2001-05-22 2004-03-30 Pfizer Prod Inc Crystalline forms of azithromycin
US6861413B2 (en) 2001-05-22 2005-03-01 Pfizer Inc. Stable non-dihydrate azithromycin oral suspensions
HRP20020614A2 (en) 2002-07-22 2004-06-30 PLIVA-ISTRAŽIVAČKI INSTITUT d.o.o. Rhombic pseudopolymorph of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin a
US7468428B2 (en) * 2004-03-17 2008-12-23 App Pharmaceuticals, Llc Lyophilized azithromycin formulation
US20060116336A1 (en) * 2004-03-17 2006-06-01 American Pharmaceutical Partners, Inc. Lyophilized azithromycin formulation
US20090093420A1 (en) * 2006-01-12 2009-04-09 Wockhardt Limited Processes for the preparation of azithromycin
BRPI1009823A2 (en) 2009-03-13 2019-09-24 Da Volterra Assistance Publique Hopitaux De Paris E Univ Paris Diderot Paris 7 "composition comprising a drug dispensing system, a first and a second composition set, and a kit."
CN103087125B (en) * 2013-02-06 2015-12-02 浙江国邦药业有限公司 Prepare the processing method that Azythromycin is treated different things alike

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1100504A (en) 1967-08-16 1968-01-24 Pliva Pharm & Chem Works Erythromycin oxime and 9-amino-3-o-cladinosyl-5-o-desosaminyl-6,11,12-trihydroxy-2,4,6,8,10,12-hexamethylpentadecane-13-olide
YU43116B (en) 1979-04-02 1989-04-30 Pliva Pharm & Chem Works Process for preparing 11-aza-4-o-cladinosyl-6-o-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one(11-aza-10-deox
SI8110592A8 (en) 1981-03-06 1996-06-30 Pliva Pharm & Chem Works Process for preparing of n-methyl-11-aza-10-deoxo-10-dihydroerythromycine a and derivatives thereof
US4474768A (en) 1982-07-19 1984-10-02 Pfizer Inc. N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor
WO1989000576A1 (en) 1987-07-09 1989-01-26 Pfizer Inc. Azithromycin dihydrate
WO1989002271A1 (en) 1987-09-10 1989-03-23 Pfizer Azithromycin and derivatives as antiprotozoal agents
JP2696608B2 (en) 1993-05-19 1998-01-14 ファイザー・インク． Azithromycin intermediate
US5605889A (en) * 1994-04-29 1997-02-25 Pfizer Inc. Method of administering azithromycin
ES2122905B1 (en) * 1996-07-11 1999-11-16 Astur Pharma Sa SYNTHESIS OF 11,12-HYDROGENOORTOBORATE 9-DESOXO-9A-AZA-11,12-DESOXI-9A-METHYL-9A-HOMOERYTHROMYCIN A. A PROCEDURE FOR THE PREPARATION OF 9-DESOXO-9A-AZA-9A-METHYL-9A -HOMOERYTHROMYCIN TO DIHYDRATE (AZYTHROMYCIN DIHYDRATE).
PT102006B (en) 1997-05-19 2000-06-30 Hovione Sociedade Quimica S A NEW AZITROMYCIN PREPARATION PROCESS
TW546302B (en) 1998-05-08 2003-08-11 Biochemie Sa Improvements in macrolide production
CA2245398C (en) 1998-08-21 2002-01-29 Apotex Inc. Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof
GB9824580D0 (en) * 1998-11-10 1999-01-06 Biochemie Sa Organic compounds
KR100700475B1 (en) 1999-06-29 2007-03-28 바이오케미 에스.에이. Macrolides
AU2001214115A1 (en) 2000-08-01 2002-02-13 Habil F. Khorakiwala Process for the preparation of anhydrous azithromycin
WO2002015842A2 (en) 2000-08-23 2002-02-28 Wockhardt Limited Process for preparation of anhydrous azithromycin

Also Published As

Publication number Publication date
ES2260047T3 (en) 2006-11-01
ATE320441T1 (en) 2006-04-15
EP1304326A1 (en) 2003-04-23
DE60026718T2 (en) 2006-11-16
EP1304326B1 (en) 2006-03-15
WO2002010144A1 (en) 2002-02-07
US6528492B1 (en) 2003-03-04
CA2417353C (en) 2009-09-01
EP1304326A4 (en) 2004-06-16
AU2000270425A1 (en) 2002-02-13
DE60026718D1 (en) 2006-05-11

Similar Documents

Publication Publication Date Title
CA2184734C (en) 3''-desmethoxy derivatives of erythromycin and azithromycin
CA2417353A1 (en) Single-step process for preparing 7,16-deoxy-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15-hexamethylbicycle (11.2.1)hexadeca-1(2)-en-8-one, and obtaining a new form of 9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin a
US5686587A (en) Intermediate for azithromycin
HU215158B (en) Process for producing an 0-benzyloxycarbonyl derivative of azythromycin a
BG105547A (en) Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions thereof
US5869629A (en) Synthesis of 9-deoxo-9a-aza-11,12-deoxy-9a-methyl-9a-homoerythromycin A 11,12 Hydrogenorthoborate dihydrate and a process for the preparation of azitromicin dihydrate
NO161497B (en) ANALOGUE PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 9A-AZA-9A-HOMOERYTROMYCIN DERIVATIVES.
NO20024321L (en) Process for the preparation of crystalline form I of cabergoline
US5922849A (en) Process for preparation of N-demethyl-4"-deoxy-erthromycins A and B
CA1209987A (en) Chemical process for the synthesis of macrolide antibiotics
HUP0104600A2 (en) Novel intermediates, process for preparing macrolide antibiotic agent therefrom
AU2001246636B2 (en) Method for preparing 9-deoxo-8a-aza-(8a-alkyl)-8a-homoerythromycin A derivatives from 9-deoxo-9(Z)-hydroxyiminoerythromycin A
US6642364B2 (en) Process to obtain clarithromycin
HU179744B (en) Process for producing semisynthetic 4-comma above comma above-amino-oleandomycin derivatives
Lazarevski et al. Ring opening reactions of 6-deoxy-9-deoxo-9a-aza-9a-homoerythromycin A 6, 9-cyclic imino ether
WO2006027800A8 (en) A novel process for preparation of a pharmaceutically pure polymorphic form 1 of olanzapine
HU182559B (en) Process for producing 4-two comma above-deoxy-4-two comma above-amino-erythromycin a derivatives of antibacterial activity
KR100359545B1 (en) Improved Manufacturing Method of D-(+)-Biotin Intermediates
US6482931B2 (en) Process for the preparation of 9-deoxo-8a-aza-(8a-alkyl)-8a-homoerythromycin A derivatives from 9-deoxo-9 (Z)-hydroxyiminoerythromycin A
NO312839B1 (en) New hydroxy derivatives of tylosin and process for their preparation
WO2001077135A1 (en) Process for preparing 6-methyl erythromycin a
WO1998041532A1 (en) Erythromycin a oxime dihydrate
MXPA99006221A (en) Improved process in a single step for the preparation of 7,16-dioxa-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihidroxi-6-etil-3,5,9,11, 13,15-hexametilbiciclo [11.2.1] hexadeca-1 (2) -en-8-ona, from erythromycin
IE862218L (en) Penicillanic acid derivatives
CA2183049A1 (en) Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed