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

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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
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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
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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

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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
US6861413B2 (en) 2001-05-22 2005-03-01 Pfizer Inc. Stable non-dihydrate azithromycin oral suspensions
AU2002256846B2 (en) * 2001-05-22 2007-04-05 Pfizer Products Inc. Crystal Forms of Azithromycin
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
EP2405909A1 (en) 2009-03-13 2012-01-18 Da Volterra Compositions and methods for elimination of gram-negative bacteria
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
SI7910768A8 (en) 1979-04-02 1996-06-30 Pliva Pharm & Chem Works Process for pripering 11-aza-4-0-cladinosyl-6-0-desosaminyl-15-ethyl- 7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl- oxacyclopentadecane-2-one and their derivatives
YU43006B (en) 1981-03-06 1989-02-28 Pliva Pharm & Chem Works Process for preparing n-methyl-11-aza-10-deoxo-10-dihydro erythromycin 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
RU2066324C1 (en) 1987-07-09 1996-09-10 Пфайзер Инк. Crystalline azithromycin dehydrate, and process for preparation thereof
WO1989002271A1 (en) 1987-09-10 1989-03-23 Pfizer Azithromycin and derivatives as antiprotozoal agents
DE69403963T2 (en) 1993-05-19 1997-11-20 Pfizer INTERMEDIATE PRODUCT FOR AZITHROMYCIN
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
EP1712556B1 (en) 1999-06-29 2010-06-02 Sandoz AG Azithromycin monohydrate
AU2001214115A1 (en) 2000-08-01 2002-02-13 Habil F. Khorakiwala Process for the preparation of anhydrous azithromycin
CA2419873A1 (en) 2000-08-23 2002-02-28 Wockhardt Limited Process for preparation of anhydrous azithromycin

Also Published As

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

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