SK37199A3 - Compound 6-o-methyl erythromycin a 9-hydrazon, method for the preparation of 6-o-methyl erythromycin a 9-hydrazon and method for the preparation of 6-o-methyl erythromycin a 9-oxime - Google Patents

Compound 6-o-methyl erythromycin a 9-hydrazon, method for the preparation of 6-o-methyl erythromycin a 9-hydrazon and method for the preparation of 6-o-methyl erythromycin a 9-oxime Download PDF

Info

Publication number: SK37199A3
Authority: SK; Slovakia
Prior art keywords: methylerythromycin; acid; group; solvent; hydrazine
Prior art date: 1998-04-14

Application number

SK371-99A

Other languages

English (en)

Slovak (sk)

Inventor

Vladimir Nadaka

Joseph Kaspi

Original Assignee

Chemagis Ltd

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.)

1998-04-14

Filing date

1999-03-19

Publication date

1999-11-08

1999-03-19 Application filed by Chemagis Ltd filed Critical Chemagis Ltd

1999-11-08 Publication of SK37199A3 publication Critical patent/SK37199A3/sk

Links

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 title claims description 50
229960002626 clarithromycin Drugs 0.000 title claims description 49
238000000034 method Methods 0.000 title claims description 28
150000001875 compounds Chemical class 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title description 18
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000002947 alkylene group Chemical group 0.000 claims abstract description 9
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 13
235000019253 formic acid Nutrition 0.000 claims description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
235000011054 acetic acid Nutrition 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
235000019260 propionic acid Nutrition 0.000 claims description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
MWBJRTBANFUBOX-SQYJNGITSA-N (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot 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)([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 MWBJRTBANFUBOX-SQYJNGITSA-N 0.000 claims description 3
BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims description 3
235000011167 hydrochloric acid Nutrition 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims description 2
150000007857 hydrazones Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class 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 abstract description 4
125000000217 alkyl group Chemical group 0.000 abstract 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000243 solution Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
239000002244 precipitate Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000011987 methylation Effects 0.000 description 4
238000007069 methylation reaction Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
238000011935 selective methylation Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229930006677 Erythromycin A Natural products 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000003386 deoximation reaction Methods 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
229960003276 erythromycin Drugs 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
235000010262 sodium metabisulphite Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012493 hydrazine sulfate Substances 0.000 description 1
229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
125000005597 hydrazone group Chemical group 0.000 description 1
-1 methyl erythromycin A Chemical compound 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003786 synthesis reaction Methods 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
- 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
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK371-99A 1998-04-14 1999-03-19 Compound 6-o-methyl erythromycin a 9-hydrazon, method for the preparation of 6-o-methyl erythromycin a 9-hydrazon and method for the preparation of 6-o-methyl erythromycin a 9-oxime SK37199A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IL12408498A IL124084A0 (en)	1998-04-14	1998-04-14	Erythromycin a derivatives and methods for the preparation thereof

Publications (1)

Publication Number	Publication Date
SK37199A3 true SK37199A3 (en)	1999-11-08

Family

ID=11071414

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK371-99A SK37199A3 (en)	1998-04-14	1999-03-19	Compound 6-o-methyl erythromycin a 9-hydrazon, method for the preparation of 6-o-methyl erythromycin a 9-hydrazon and method for the preparation of 6-o-methyl erythromycin a 9-oxime

Country Status (6)

Country	Link
EP (1)	EP0955307A1 (cs)
JP (1)	JPH11310592A (cs)
CZ (1)	CZ96799A3 (cs)
HU (1)	HUP9900689A2 (cs)
IL (1)	IL124084A0 (cs)
SK (1)	SK37199A3 (cs)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100361397B1 (ko) *	2000-03-15	2002-11-23	한미약품공업 주식회사	에리스로마이신 에이 9-오-트로필옥심 유도체를 이용한클라리스로마이신의 제조방법
KR100372254B1 (en) *	2002-07-15	2003-02-19	Korea United Pharm Inc	Erythromycin a 9-o-pseudosaccharinyl oxime derivative and process for preparing clarithromycin using the same
CN102382157B (zh) *	2010-09-03	2015-04-08	上海医药工业研究院	一种红霉素a衍生物及其制备方法
CN102786570B (zh) *	2011-05-18	2016-02-10	上海医药工业研究院	大环内酯类化合物、其制备方法、应用以及中间体
CN103130852B (zh) *	2011-11-25	2016-03-16	上海医药工业研究院	一种红霉素a衍生物、其制备方法、中间体及应用
CN104337826B (zh) *	2013-07-30	2018-02-13	上海医药工业研究院	大环内酯类化合物或其盐的应用及含其的药物组合物
CN106905204B (zh) *	2017-02-24	2018-07-20	杭州新桂实业有限公司	一种克拉霉素合成过程中甲基化反应溶剂的回收套用方法
CN110615822B (zh) *	2018-06-19	2023-04-28	上海医药工业研究院有限公司	大环内酯类化合物、其合成方法、药物组合物与应用
CN114858953B (zh) *	2022-05-20	2023-11-21	大连工业大学	一种动物源食品中红霉素及降解产物的检测试剂盒及检测方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA695765B (en) *	1968-08-29	1971-03-31	Lilly Co Eli	Erythromycylamine and process for preparing same
GB1344629A (en) *	1970-09-30	1974-01-23	Lilly Industries Ltd	Erythromycin azine derivatives
JPS60214796A (ja) *	1984-04-06	1985-10-28	Taisho Pharmaceut Co Ltd	６−０−メチルエリスロマイシン類の製法
US4670549A (en) *	1985-03-18	1987-06-02	Taisho Pharmaceutical Co., Ltd.	Method for selective methylation of erythromycin a derivatives
GB8721165D0 (en) *	1987-09-09	1987-10-14	Beecham Group Plc	Chemical compounds
US5929219A (en) *	1997-09-10	1999-07-27	Abbott Laboratories	9-hydrazone and 9-azine erythromycin derivatives and a process of making the same
WO1999040097A1 (en) *	1998-02-04	1999-08-12	Teva Pharmaceutical Industries Ltd.	Process for making clarithromycin

1998
- 1998-04-14 IL IL12408498A patent/IL124084A0/xx unknown
1999
- 1999-03-18 HU HU9900689A patent/HUP9900689A2/hu unknown
- 1999-03-18 EP EP99302110A patent/EP0955307A1/en not_active Withdrawn
- 1999-03-19 SK SK371-99A patent/SK37199A3/sk unknown
- 1999-03-19 CZ CZ99967A patent/CZ96799A3/cs unknown
- 1999-03-26 JP JP11083340A patent/JPH11310592A/ja active Pending

Also Published As

Publication number	Publication date
HUP9900689A2 (hu)	1999-11-29
HU9900689D0 (en)	1999-05-28
JPH11310592A (ja)	1999-11-09
CZ96799A3 (cs)	1999-11-17
EP0955307A1 (en)	1999-11-10
IL124084A0 (en)	1999-04-11

Publication	Publication Date	Title
EP0180415B1 (en)	1990-01-31	A 6-0-methylerythromycin A derivative
KR920002142B1 (ko)	1992-03-12	에리트로마이신 a 유도체의 선택적인 메틸화 방법
US4672109A (en)	1987-06-09	Method for selective methylation of erythromycin A derivatives
HU193886B (en)	1987-12-28	Process for preparing epimer azahomoerythromycin a derivatives
HU215158B (hu)	1998-12-28	Eljárás egy azitromicin A O-benziloxi-karbonil-származék előállítására
EP0240264A2 (en)	1987-10-07	Improved process for preparing macrolide derivatives
EP0080818B1 (en)	1985-04-17	Erythromycin b derivatives
HUP0000198A2 (hu)	2000-08-28	Eritromicin- A származékai
SK37199A3 (en)	1999-11-08	Compound 6-o-methyl erythromycin a 9-hydrazon, method for the preparation of 6-o-methyl erythromycin a 9-hydrazon and method for the preparation of 6-o-methyl erythromycin a 9-oxime
US4833236A (en)	1989-05-23	Erythromycin derivatives
JPS6360031B2 (cs)	1988-11-22
EP0081305B1 (en)	1985-04-24	Erythromycin a derivatives
US6165986A (en)	2000-12-26	Erythromycin a derivatives
US5602239A (en)	1997-02-11	5-O-desosaminylerythronolide derivatives
US6599886B2 (en)	2003-07-29	Macrolide intermediates in the preparation of clarithromycin
EP0972778A1 (en)	2000-01-19	Erythromycin derivatives and methods for the preparation thereof
JPS5827798B2 (ja)	1983-06-11	新規抗菌剤の中間体
BRPI0619556A2 (pt)	2011-10-04	processo para desmetilação de grupo 3' -dimetil amino de compostos eritromicina
JPH0136834B2 (cs)	1989-08-02
WO1998041532A1 (en)	1998-09-24	Erythromycin a oxime dihydrate
WO2004007518A1 (en)	2004-01-22	Erythromycin a 9-o-pseudosaccharinyloxime derivatives and process for the preparation of clarithromycin using the same
JPH0529038B2 (cs)	1993-04-28
CZ96999A3 (cs)	2000-02-16	Nové deriváty erytromycinu A, způsob selektivní methylace 6-OH skupiny erytromycinu A, a způsob přípravy 6-0- methylerytromycinu A
IL128161A (en)	2001-09-13	Methods for the preparation of clarithromycin from its 9- hydrazone
JPH06247996A (ja)	1994-09-06	６−ｏ−メチルエリスロマイシンａ誘導体