ZA200301384B - Process for preparation of anhydrous azithromycin. - Google Patents

Process for preparation of anhydrous azithromycin. Download PDF

Info

Publication number: ZA200301384B
Authority: ZA; South Africa
Prior art keywords: process according; solvent; compound; formula; water
Prior art date: 2000-08-23

Application number

ZA200301384A

Other languages

English (en)

Inventor

Khan Anjum Reyaz

Shiva P Singh

Jaweed Mukarram Siddi Mohammed

Manish Purohit

Original Assignee

Wockhardt 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.)

2000-08-23

Filing date

2003-02-20

Publication date

2004-04-02

2003-02-20 Application filed by Wockhardt Ltd filed Critical Wockhardt Ltd

2004-04-02 Publication of ZA200301384B publication Critical patent/ZA200301384B/en

Links

238000000034 method Methods 0.000 title claims description 31
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 title description 16
238000002360 preparation method Methods 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 40
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 21
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
VQEMDSRIOVZAOM-UHFFFAOYSA-N 4-(4-methylsulfonylphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CSC(N)=N1 VQEMDSRIOVZAOM-UHFFFAOYSA-N 0.000 claims description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
229960004924 azithromycin dihydrate Drugs 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
229960004592 isopropanol Drugs 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
HQUPLSLYZHKKQT-WVVFQGGUSA-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-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-o Chemical compound O.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 HQUPLSLYZHKKQT-WVVFQGGUSA-N 0.000 claims description 5
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 5
229960003256 azithromycin monohydrate Drugs 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 5
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 4
AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims description 4
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 3
150000001491 aromatic compounds Chemical class 0.000 claims description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
125000003158 alcohol group Chemical group 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 14
-1 for example Chemical class 0.000 description 13
239000000047 product Substances 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000002552 dosage form Substances 0.000 description 9
239000007788 liquid Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
229960004099 azithromycin Drugs 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
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 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
238000003860 storage Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229930006677 Erythromycin A Natural products 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
239000003849 aromatic solvent Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000002178 crystalline material Substances 0.000 description 3
229960003276 erythromycin Drugs 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
230000036571 hydration Effects 0.000 description 3
238000006703 hydration reaction Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000167854 Bourreria succulenta Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
229930091371 Fructose Natural products 0.000 description 2
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
239000005715 Fructose Substances 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
235000019693 cherries Nutrition 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000002502 liposome Substances 0.000 description 2
239000003120 macrolide antibiotic agent Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
244000005700 microbiome Species 0.000 description 2
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150000002923 oximes Chemical class 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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238000012360 testing method Methods 0.000 description 2
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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 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
- 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)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Medicinal Preparation (AREA)

ZA200301384A 2000-08-23 2003-02-20 Process for preparation of anhydrous azithromycin. ZA200301384B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US22734100P	2000-08-23	2000-08-23

Publications (1)

Publication Number	Publication Date
ZA200301384B true ZA200301384B (en)	2004-04-02

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ID=22852706

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200301384A ZA200301384B (en)	2000-08-23	2003-02-20	Process for preparation of anhydrous azithromycin.

Country Status (10)

Country	Link
US (2)	US7414114B2 (de)
EP (1)	EP1313749B1 (de)
JP (1)	JP2004506664A (de)
AT (1)	ATE306491T1 (de)
AU (1)	AU2001280000A1 (de)
CA (1)	CA2419873A1 (de)
DE (1)	DE60114028T2 (de)
NO (1)	NO20030772L (de)
WO (1)	WO2002015842A2 (de)
ZA (1)	ZA200301384B (de)

Families Citing this family (18)

* 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
DE60026718T2 (de)	2000-07-25	2006-11-16	Laboratorio Silanes, S.A. De C.V.	Einstufiges verfahren zur herstellung von 7,16-deoxy-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15-hexamethylbicycle(11.2.11)hexadeca-1(2)-en-8-ona undeine neue form von 9-desoxo-9a-methyl-9a-aza-9a-homoerythromycin a
JP2004506664A (ja) *	2000-08-23	2004-03-04	ウォックハート・リミテッド	無水アジトロマイシンの製造法
ES2258142T3 (es)	2001-05-22	2006-08-16	Pfizer Products Inc.	Nueva forma cristalina.
US6861413B2 (en)	2001-05-22	2005-03-01	Pfizer Inc.	Stable non-dihydrate azithromycin oral suspensions
EP1490382A4 (de) *	2002-04-03	2007-09-12	Hanmi Pharm Ind Co Ltd	Verfahren zur herstellung von azithromycin und dabei verwendetes kristallines 9-desoxo-9a-aza-9a-homoerythromycin-a-hydrat
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
US7435805B2 (en) *	2003-05-30	2008-10-14	Glaxpsmithkline Istrazivacki	O-alkyl macrolide and azalide derivatives and regioselective process for their preparation
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
US7683162B2 (en)	2004-08-30	2010-03-23	Taro Pharmaceutical Industries Limited	Process of preparing a crystalline azithromycin monohydrate
EP1976860A2 (de) *	2006-01-12	2008-10-08	Wockhardt Limited	Verfahren für die zubereitung von azithromycin
US20120058936A1 (en)	2009-03-13	2012-03-08	Assistance Publique - Hopitaux De Paris	Compositions and methods for elimination of gram negative bacteria
US8106111B2 (en)	2009-05-15	2012-01-31	Eastman Chemical Company	Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions
US8709310B2 (en)	2011-01-05	2014-04-29	Hospira, Inc.	Spray drying vancomycin
US20130172271A1 (en) *	2012-01-04	2013-07-04	Cynthia Fragale	Pharmaceutical Spray Drying
CN103897002A (zh) *	2012-12-31	2014-07-02	菏泽市方明制药有限公司	一种粗品硫氰酸红霉素制备红霉素a9-肟的方法
CN104043104B (zh)	2013-03-15	2018-07-10	浙江创新生物有限公司	含盐酸万古霉素的喷雾干粉及其工业化制备方法

Family Cites Families (45)

* 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
US3736313A (en)	1971-02-26	1973-05-29	Abbott Lab	Erythromycin derivatives
US3842068A (en)	1972-06-15	1974-10-15	Abbott Lab	8-epi-erythromycins
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
US4331803A (en)	1980-06-04	1982-05-25	Taisho Pharmaceutical Co., Ltd.	Novel erythromycin compounds
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
DE3136679A1 (de)	1981-09-16	1983-03-24	Bayer Ag, 5090 Leverkusen	Kationische triazinfarbstoffe, ihre herstellung und verwendung
US4474768A (en)	1982-07-19	1984-10-02	Pfizer Inc.	N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor
PH19293A (en)	1982-11-15	1986-03-04	Pfizer	Epimeric azahomoerythromycin,pharmaceutical composition containing the same and method of use thereof
US4526889A (en)	1982-11-15	1985-07-02	Pfizer Inc.	Epimeric azahomoerythromycin A derivative, intermediates and method of use
US4526888A (en)	1983-04-29	1985-07-02	Bristol-Myers Company	Nephrotoxicity inhibitors for aminoglycoside antibiotics
US4492688A (en)	1983-11-25	1985-01-08	Pfizer Inc.	Antibacterial cyclic ethers of 9-deoxo-9a-aza-9a-homoerythromycin A and intermediates therefor
US4464527A (en)	1983-06-30	1984-08-07	Pfizer Inc.	Antibacterial 9-deoxo-9a-alkyl-9a-aza-9a-homoerythromycin A derivatives and intermediates therefore
US4465674A (en)	1983-09-06	1984-08-14	Pfizer Inc.	Azahomoerythromycin D derivative and intermediates therefor
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
US4518590A (en)	1984-04-13	1985-05-21	Pfizer Inc.	9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method
JPS6281399A (ja)	1985-10-04	1987-04-14	Taisho Pharmaceut Co Ltd	エリスロマイシン類のオキシム誘導体の製造法
JPS6287599A (ja)	1985-10-14	1987-04-22	Taisho Pharmaceut Co Ltd	エリスロマイシン類のオキシム誘導体の製造法
US5110800A (en)	1986-02-18	1992-05-05	Eli Lilly And Company	Derivatives of erythromycylamine
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
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
US5141926A (en)	1990-04-18	1992-08-25	Abbott Laboratories	Erythromycin derivatives
SI9011409A (en)	1990-07-18	1995-10-31	Pliva Pharm & Chem Works	O-methyl azitromycin derivates, methods and intermediates for their preparation and methods for preparation of pharmaceuticals products which comprise them
US5350839A (en)	1990-10-15	1994-09-27	Taisho Pharmaceutical Co., Ltd.	2'-position modified compound of erythromycin or its derivative
US5202434A (en)	1991-04-05	1993-04-13	Merck & Co., Inc.	8a-aza-8a-homoerythromycin lactams
US5189159A (en)	1992-04-02	1993-02-23	Merck & Co., Inc.	8a-AZA-8a-homoerythromycin cyclic iminoethers
US5215980A (en)	1992-01-17	1993-06-01	Merck & Co., Inc.	10-AZA-9-deoxo-11-deoxy-erythromycin A and derivatives thereof
US5332807A (en)	1993-04-14	1994-07-26	Merck & Co., Inc.	Process of producing 8A- and 9A-azalide antibiotics
US5686587A (en)	1993-05-19	1997-11-11	Pfizer Inc.	Intermediate for azithromycin
US5441939A (en)	1994-03-04	1995-08-15	Pfizer Inc.	3"-desmethoxy derivatives of erythromycin and azithromycin
US5605889A (en)	1994-04-29	1997-02-25	Pfizer Inc.	Method of administering azithromycin
US5808017A (en)	1996-04-10	1998-09-15	Abbott Laboratories	Process for preparing erythromycin A oxime
US5958888A (en)	1996-07-02	1999-09-28	Merial, Inc.	Water miscible macrolide solutions
US5723447A (en)	1996-07-02	1998-03-03	Rhone Merieux, Inc.	Water miscible erythromycin solutions
ES2122905B1 (es)	1996-07-11	1999-11-16	Astur Pharma Sa	Sintesis de 11,12-hidrogenoortoborato de 9-desoxo-9a-aza-11,12-desoxi-9a-metil-9a-homoeritromicina a. un procedimiento para la preparacion de 9-desoxo-9a-aza-9a-metil-9a-homoeritromicina a dihidrato (azitromicina dihidrato).
PT102006B (pt)	1997-05-19	2000-06-30	Hovione Sociedade Quimica S A	Novo processo de preparacao de azitromicina
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
WO2002009640A2 (en) *	2000-08-01	2002-02-07	Shiva Prasad Singh	Process for the preparation of anhydrous azithromycin
JP2004506664A (ja) *	2000-08-23	2004-03-04	ウォックハート・リミテッド	無水アジトロマイシンの製造法
ES2258142T3 (es)	2001-05-22	2006-08-16	Pfizer Products Inc.	Nueva forma cristalina.
US6855813B2 (en)	2002-07-19	2005-02-15	Alembic Limited	Process for the preparation of azithromycin monohydrate
WO2006011160A1 (en)	2004-06-28	2006-02-02	Alembic Limited	Process for the preparation of azithromycin monohydrate isopropanol clathrate
US7683162B2 (en)	2004-08-30	2010-03-23	Taro Pharmaceutical Industries Limited	Process of preparing a crystalline azithromycin monohydrate

2001
- 2001-08-23 JP JP2002520756A patent/JP2004506664A/ja active Pending
- 2001-08-23 AT AT01958277T patent/ATE306491T1/de not_active IP Right Cessation
- 2001-08-23 CA CA002419873A patent/CA2419873A1/en not_active Abandoned
- 2001-08-23 DE DE60114028T patent/DE60114028T2/de not_active Expired - Fee Related
- 2001-08-23 EP EP01958277A patent/EP1313749B1/de not_active Expired - Lifetime
- 2001-08-23 AU AU2001280000A patent/AU2001280000A1/en not_active Abandoned
- 2001-08-23 WO PCT/IB2001/001523 patent/WO2002015842A2/en not_active Ceased
2003
- 2003-02-18 NO NO20030772A patent/NO20030772L/no not_active Application Discontinuation
- 2003-02-20 ZA ZA200301384A patent/ZA200301384B/en unknown
- 2003-02-24 US US10/373,349 patent/US7414114B2/en not_active Expired - Fee Related
2008
- 2008-07-31 US US12/184,051 patent/US20090018090A1/en not_active Abandoned

Also Published As

Publication number	Publication date
DE60114028T2 (de)	2006-07-13
WO2002015842A2 (en)	2002-02-28
US7414114B2 (en)	2008-08-19
US20030139583A1 (en)	2003-07-24
NO20030772L (no)	2003-04-22
AU2001280000A1 (en)	2002-03-04
US20090018090A1 (en)	2009-01-15
NO20030772D0 (no)	2003-02-18
WO2002015842A3 (en)	2002-10-31
DE60114028D1 (de)	2006-02-23
CA2419873A1 (en)	2002-02-28
EP1313749B1 (de)	2005-10-12
EP1313749A2 (de)	2003-05-28
ATE306491T1 (de)	2005-10-15
JP2004506664A (ja)	2004-03-04
EP1313749A4 (de)	2004-01-21

Publication	Publication Date	Title
US20090018090A1 (en)	2009-01-15	Process for preparation of anhydrous azithromycin
KR100885755B1 (ko)	2009-02-26	리팍시민의 신규의 다형체, 그의 제조방법, 및 그의의약품으로서의 용도
KR100867751B1 (ko)	2008-11-10	리팍시민의 다형체, 그의 제조방법, 및 그의의약품으로서의 용도
EP0184170B1 (de)	1991-10-16	Aminomethyl-, N-Phenyl-substituierte Oxooxazolidin Derivate nützlich als antibakterielle Mittel
US4042700A (en)	1977-08-16	Quaternary N-β-substituted N-alkyl-nortropine benzilates
AU754705B2 (en)	2002-11-21	Thienylazolylalcoxyethanamines, their preparation and their application as medicaments
RU2215740C2 (ru)	2003-11-10	Оксазолидиноновые производные и фармацевтические композиции на их основе
CZ391091A3 (en)	1994-01-19	Crystalline paroxetin hydrochloride hemihydrate, process for producing thereof and pharmaceutical preparations in which it is comprised
SK285165B6 (sk)	2006-07-07	Tetrahydropyridoétery, farmaceutický prostriedok s ich obsahom a ich použitie
WO2002009640A2 (en)	2002-02-07	Process for the preparation of anhydrous azithromycin
AU597194B2 (en)	1990-05-24	Antibacterial 9-deoxo-9a-allyl and propargyl-9a-aza-9a-homoerythromycin a derivatives
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US6066647A (en)	2000-05-23	Zwitterionic forms of trovafloxacin
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