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
238000001802 infusion Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
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
229910052757 nitrogen Inorganic materials 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
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
238000001953 recrystallisation Methods 0.000 description 2
238000006049 ring expansion reaction Methods 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
238000012360 testing method Methods 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
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
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 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
108010011485 Aspartame Proteins 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000238367 Mya arenaria Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000000556 agonist Substances 0.000 description 1
239000005456 alcohol based solvent Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
239000000605 aspartame Substances 0.000 description 1
229960003438 aspartame Drugs 0.000 description 1
235000010357 aspartame Nutrition 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
239000006189 buccal tablet Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007958 cherry flavor Substances 0.000 description 1
QVFWZNCVPCJQOP-UHFFFAOYSA-N chloralodol Chemical compound CC(O)(C)CC(C)OC(O)C(Cl)(Cl)Cl QVFWZNCVPCJQOP-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003759 ester based solvent Substances 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
125000005908 glyceryl ester group Chemical group 0.000 description 1
239000001087 glyceryl triacetate Substances 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
OIPZNTLJVJGRCI-UHFFFAOYSA-M octadecanoyloxyaluminum;dihydrate Chemical compound O.O.CCCCCCCCCCCCCCCCCC(=O)O[Al] OIPZNTLJVJGRCI-UHFFFAOYSA-M 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000006485 reductive methylation reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007892 solid unit dosage form Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000009637 wintergreen oil Substances 0.000 description 1

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

Family

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 (fr)
EP (1)	EP1313749B1 (fr)
JP (1)	JP2004506664A (fr)
AT (1)	ATE306491T1 (fr)
AU (1)	AU2001280000A1 (fr)
CA (1)	CA2419873A1 (fr)
DE (1)	DE60114028T2 (fr)
NO (1)	NO20030772L (fr)
WO (1)	WO2002015842A2 (fr)
ZA (1)	ZA200301384B (fr)

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
CA2417353C (fr)	2000-07-25	2009-09-01	Laboratorio Silanes,S.A. De C.V.	Methode de synthese en une etape de la 7,16-desoxy-2-aza-10-o-cladinosyl-12-o-desosaminyl-4,5-dihydroxy-6-ethyl-3,5,9,11,13,15-hexamethylbicyclo(11.2.1)hexadeca-1(2)-en-8-one et de production d'une nouvelle forme de 9-desoxo-9a-methyl-9a-aza-9a-homoerythromycine a
WO2002015842A2 (fr) *	2000-08-23	2002-02-28	Wockhardt Limited	Procede de preparation d'azithromycine anhydre
GEP20084399B (en)	2001-05-22	2008-06-10	Pfizer Prod Inc	Crystal forms of azithromycin
US6861413B2 (en)	2001-05-22	2005-03-01	Pfizer Inc.	Stable non-dihydrate azithromycin oral suspensions
EP1490382A4 (fr) *	2002-04-03	2007-09-12	Hanmi Pharm Ind Co Ltd	Procede de preparation d'azithromyxine et de 9-deoxo-9a-homoerythromycine cristalline a hydrate
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 (fr) *	2006-01-12	2008-10-08	Wockhardt Limited	Procédés de synthèse d azithromycine
KR20120004448A (ko)	2009-03-13	2012-01-12	다 볼떼라	그람음성 박테리아 제거용 조성물 및 방법
US8106111B2 (en)	2009-05-15	2012-01-31	Eastman Chemical Company	Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions
CA2823628A1 (fr)	2011-01-05	2012-07-12	Hospira, Inc.	Sechage par atomisation de la vancomycine
WO2013103801A1 (fr) *	2012-01-04	2013-07-11	Hospira, Inc.	Séchage par pulvérisation pharmaceutique
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
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
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
US4526889A (en)	1982-11-15	1985-07-02	Pfizer Inc.	Epimeric azahomoerythromycin A derivative, intermediates and method of use
PH19293A (en)	1982-11-15	1986-03-04	Pfizer	Epimeric azahomoerythromycin,pharmaceutical composition containing the same and method of use thereof
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
RU2066324C1 (ru)	1987-07-09	1996-09-10	Пфайзер Инк.	Кристаллический дигидрат азитромицина и способ его получения
WO1989002271A1 (fr)	1987-09-10	1989-03-23	Pfizer	Azithromycine et derives utilises comme agents anti-protozoaires
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
EP0553353A1 (fr)	1990-10-15	1993-08-04	Taisho Pharmaceutical Co. Ltd	Erythromycine modifiee en 2' ou derive de cette substance
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
ATE154806T1 (de)	1993-05-19	1997-07-15	Pfizer	Zwischenprodukt für 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 (fr) *	1998-08-21	2002-01-29	Apotex Inc.	Clathrate d'isopropanol monohydrate d'azithromycine et methodes d'obtention
AU2001214115A1 (en) *	2000-08-01	2002-02-13	Habil F. Khorakiwala	Process for the preparation of anhydrous azithromycin
WO2002015842A2 (fr) *	2000-08-23	2002-02-28	Wockhardt Limited	Procede de preparation d'azithromycine anhydre
GEP20084399B (en)	2001-05-22	2008-06-10	Pfizer Prod Inc	Crystal forms of azithromycin
US6855813B2 (en)	2002-07-19	2005-02-15	Alembic Limited	Process for the preparation of azithromycin monohydrate
US7235646B2 (en)	2004-06-28	2007-06-26	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 WO PCT/IB2001/001523 patent/WO2002015842A2/fr not_active Ceased
- 2001-08-23 JP JP2002520756A patent/JP2004506664A/ja active Pending
- 2001-08-23 AU AU2001280000A patent/AU2001280000A1/en not_active Abandoned
- 2001-08-23 CA CA002419873A patent/CA2419873A1/fr not_active Abandoned
- 2001-08-23 AT AT01958277T patent/ATE306491T1/de not_active IP Right Cessation
- 2001-08-23 DE DE60114028T patent/DE60114028T2/de not_active Expired - Fee Related
- 2001-08-23 EP EP01958277A patent/EP1313749B1/fr not_active Expired - Lifetime
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
ATE306491T1 (de)	2005-10-15
JP2004506664A (ja)	2004-03-04
NO20030772L (no)	2003-04-22
US20090018090A1 (en)	2009-01-15
WO2002015842A2 (fr)	2002-02-28
AU2001280000A1 (en)	2002-03-04
CA2419873A1 (fr)	2002-02-28
DE60114028D1 (de)	2006-02-23
NO20030772D0 (no)	2003-02-18
WO2002015842A3 (fr)	2002-10-31
EP1313749A2 (fr)	2003-05-28
DE60114028T2 (de)	2006-07-13
EP1313749A4 (fr)	2004-01-21
US20030139583A1 (en)	2003-07-24
US7414114B2 (en)	2008-08-19
EP1313749B1 (fr)	2005-10-12

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 (fr)	1991-10-16	Dérivés d'aminométhyl-oxo-oxazolidinyl benzène comme agents antibactériens
US4042700A (en)	1977-08-16	Quaternary N-β-substituted N-alkyl-nortropine benzilates
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 (fr)	2002-02-07	Élaboration d'azithromycine anhydre
AU597194B2 (en)	1990-05-24	Antibacterial 9-deoxo-9a-allyl and propargyl-9a-aza-9a-homoerythromycin a derivatives
IE61019B1 (en)	1994-09-07	(Benzofuran-2-yl) imidazoles having pharmaceutical activity, their salts and relevant production processes
US4692515A (en)	1987-09-08	Adamantane-spirolactams
NZ524464A (en)	2004-11-26	Process for preparation of anhydrous azithromycin
CA2007785C (fr)	1996-09-03	1-[3-(2-hydroxy-3-alkylaminopropoxy)-2-thienyl] -2-thienyl]-3-phenyl-1-propanones et procede de preparation
WO1997007800A1 (fr)	1997-03-06	Formes zwitterioniques de trovafloxacine
WO2005030698A1 (fr)	2005-04-07	Procede de preparation de voglibose
JPS5935387B2 (ja)	1984-08-28	３−アミノ−２−ヒドロキシプロパンのジ−置換フエノ−ルエ−テル類、その製法ならびに医薬用途
US6066647A (en)	2000-05-23	Zwitterionic forms of trovafloxacin
US6835734B2 (en)	2004-12-28	1,3-dioxolanes with antitussive activity
US5084464A (en)	1992-01-28	Conjugated γ-hydroxybutenolide compounds and antiulcer agents containing the same as an effective ingredient
MXPA98001664A (en)	1998-11-12	Zwitterionic forms of trovafloxacin, procedure for its preparation, compositions that contain them and use of the mis
HK1096396B (en)	2012-08-31	New polymorphous forms of rifaximin, processes for their production and use thereof in the medicinal preparations
HUT66704A (en)	1994-12-28	Hydrocloride salts of indoline derivatives, pharmaceutical compositions contg. them and process for preparing these compounds
MXPA00004528A (en)	2001-07-09	Oxazolidinone derivatives and pharmaceutical compositions