SK142000A3 - Erythromycin a oxime solvates - Google Patents

Erythromycin a oxime solvates Download PDF

Info

Publication number: SK142000A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; solvate; solvent; erythromycin
Prior art date: 1997-07-08

Application number

SK14-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Immaculada Bosch

Victor Centellas

Jose Diago

Original Assignee

Biochemie Sa

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.)

1997-07-08

Filing date

1998-07-06

Publication date

2000-06-12

1997-07-08 Priority claimed from GBGB9714358.0A external-priority patent/GB9714358D0/en

1998-05-13 Priority claimed from GBGB9810245.2A external-priority patent/GB9810245D0/en

1998-07-06 Application filed by Biochemie Sa filed Critical Biochemie Sa

2000-06-12 Publication of SK142000A3 publication Critical patent/SK142000A3/sk

Links

KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\O)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 title claims abstract description 38
239000012453 solvate Substances 0.000 title claims description 56
150000001875 compounds Chemical class 0.000 claims description 93
239000002904 solvent Substances 0.000 claims description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
239000003960 organic solvent Substances 0.000 claims description 28
239000003849 aromatic solvent Substances 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 21
230000008569 process Effects 0.000 claims description 16
239000003120 macrolide antibiotic agent Substances 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
RXZBMPWDPOLZGW-XMRMVWPWSA-N (E)-roxithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/OCOCCOC)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 RXZBMPWDPOLZGW-XMRMVWPWSA-N 0.000 claims description 6
229960004099 azithromycin Drugs 0.000 claims description 6
MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims description 6
229960005224 roxithromycin Drugs 0.000 claims description 6
230000002051 biphasic effect Effects 0.000 claims description 5
229960002626 clarithromycin Drugs 0.000 claims description 5
AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 4
238000005804 alkylation reaction Methods 0.000 claims description 4
HRKNNHYKWGYTEN-HOQMJRDDSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)NC[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 HRKNNHYKWGYTEN-HOQMJRDDSA-N 0.000 claims description 3
238000003386 deoximation reaction Methods 0.000 claims description 3
230000008707 rearrangement Effects 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
125000003544 oxime group Chemical group 0.000 claims description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000007858 starting material Substances 0.000 description 10
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
229960003276 erythromycin Drugs 0.000 description 8
239000012458 free base Substances 0.000 description 8
150000003839 salts Chemical group 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
239000002585 base Substances 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
238000001035 drying Methods 0.000 description 5
229940043265 methyl isobutyl ketone Drugs 0.000 description 5
239000000843 powder Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
229930006677 Erythromycin A Natural products 0.000 description 4
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
-1 alkyl ketones Chemical class 0.000 description 4
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
229940011051 isopropyl acetate Drugs 0.000 description 4
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
229940041033 macrolides Drugs 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
229960004100 dirithromycin Drugs 0.000 description 2
WLOHNSSYAXHWNR-NXPDYKKBSA-N dirithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H]2O[C@H](COCCOC)N[C@H]([C@@H]2C)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 WLOHNSSYAXHWNR-NXPDYKKBSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229940078552 o-xylene Drugs 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000002411 thermogravimetry Methods 0.000 description 2
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical class CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002635 aromatic organic solvent Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003988 headspace gas chromatography Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical class CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical class CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
ing And Chemical Polishing (AREA)
Bidet-Like Cleaning Device And Other Flush Toilet Accessories (AREA)
Dental Preparations (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK14-2000A 1997-07-08 1998-07-06 Erythromycin a oxime solvates SK142000A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9714358.0A GB9714358D0 (en)	1997-07-08	1997-07-08	Organic compounds
GBGB9810245.2A GB9810245D0 (en)	1998-05-13	1998-05-13	Organic compounds
PCT/EP1998/004166 WO1999002541A2 (en)	1997-07-08	1998-07-06	Erythromycin a oxime solvates

Publications (1)

Publication Number	Publication Date
SK142000A3 true SK142000A3 (en)	2000-06-12

Family

ID=26311850

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK14-2000A SK142000A3 (en)	1997-07-08	1998-07-06	Erythromycin a oxime solvates

Country Status (15)

Country	Link
US (1)	US6504017B1 (id)
EP (1)	EP0994889B1 (id)
JP (1)	JP2001506281A (id)
KR (1)	KR100378434B1 (id)
CN (1)	CN1157402C (id)
AT (1)	ATE269350T1 (id)
AU (1)	AU8973398A (id)
BR (1)	BR9811674A (id)
CA (1)	CA2295629A1 (id)
DE (1)	DE69824590T2 (id)
ES (1)	ES2224425T3 (id)
ID (1)	ID24108A (id)
PT (1)	PT994889E (id)
SK (1)	SK142000A3 (id)
WO (1)	WO1999002541A2 (id)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2245398C (en) *	1998-08-21	2002-01-29	Apotex Inc.	Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof
DE60029589T2 (de) *	1999-06-29	2007-07-19	Sandoz Ag	Verfahren zur herstellung von azithromycin
FR2802534B1 (fr) *	1999-12-20	2002-02-01	Merial Sas	Procede pour preparer et isoler la 9-deoxo-9 (z)- hydroxyiminoerythromycine a
TW200302830A (en) *	2002-01-11	2003-08-16	Chugai Pharmaceutical Co Ltd	Anhydrate/hydrate of an erythromycin derivative and processes for preparing said anhydrate/hydrate
US20060116336A1 (en) *	2004-03-17	2006-06-01	American Pharmaceutical Partners, Inc.	Lyophilized azithromycin formulation
US7468428B2 (en) *	2004-03-17	2008-12-23	App Pharmaceuticals, Llc	Lyophilized azithromycin formulation
CN103713080A (zh) *	2013-12-25	2014-04-09	挑战（天津）动物药业有限公司	一种加米霉素的含量检测方法

Family Cites Families (4)

* 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
JP2751385B2 (ja) *	1988-05-19	1998-05-18	大正製薬株式会社	エリスロマイシンａオキシム及びその塩の製造方法
US5912331A (en) *	1991-03-15	1999-06-15	Merck & Co., Inc.	Process for the preparation of 9-deoxo-9(Z)-hydroxyiminoerythromycin A
US5808017A (en) *	1996-04-10	1998-09-15	Abbott Laboratories	Process for preparing erythromycin A oxime

1998
- 1998-07-06 PT PT98941292T patent/PT994889E/pt unknown
- 1998-07-06 SK SK14-2000A patent/SK142000A3/sk unknown
- 1998-07-06 ID IDW20000008A patent/ID24108A/id unknown
- 1998-07-06 EP EP98941292A patent/EP0994889B1/en not_active Expired - Lifetime
- 1998-07-06 KR KR10-1999-7012218A patent/KR100378434B1/ko not_active Expired - Fee Related
- 1998-07-06 ES ES98941292T patent/ES2224425T3/es not_active Expired - Lifetime
- 1998-07-06 CN CNB988070103A patent/CN1157402C/zh not_active Expired - Fee Related
- 1998-07-06 CA CA002295629A patent/CA2295629A1/en not_active Abandoned
- 1998-07-06 BR BR9811674-6A patent/BR9811674A/pt not_active Application Discontinuation
- 1998-07-06 AU AU89733/98A patent/AU8973398A/en not_active Abandoned
- 1998-07-06 DE DE69824590T patent/DE69824590T2/de not_active Expired - Fee Related
- 1998-07-06 US US09/462,302 patent/US6504017B1/en not_active Expired - Fee Related
- 1998-07-06 JP JP50811999A patent/JP2001506281A/ja active Pending
- 1998-07-06 AT AT98941292T patent/ATE269350T1/de not_active IP Right Cessation
- 1998-07-06 WO PCT/EP1998/004166 patent/WO1999002541A2/en not_active Ceased

Also Published As

Publication number	Publication date
JP2001506281A (ja)	2001-05-15
CA2295629A1 (en)	1999-01-21
KR100378434B1 (ko)	2003-03-29
ATE269350T1 (de)	2004-07-15
EP0994889B1 (en)	2004-06-16
DE69824590D1 (de)	2004-07-22
CN1157402C (zh)	2004-07-14
AU8973398A (en)	1999-02-08
KR20010014150A (ko)	2001-02-26
WO1999002541A2 (en)	1999-01-21
DE69824590T2 (de)	2005-06-30
US6504017B1 (en)	2003-01-07
PT994889E (pt)	2004-10-29
EP0994889A2 (en)	2000-04-26
WO1999002541A3 (en)	1999-04-01
ES2224425T3 (es)	2005-03-01
ID24108A (id)	2000-07-06
CN1262686A (zh)	2000-08-09
BR9811674A (pt)	2000-09-19

Publication	Publication Date	Title
KR920002142B1 (ko)	1992-03-12	에리트로마이신 a 유도체의 선택적인 메틸화 방법
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