NO315748B1 - Fremgangsmate for fremstilling av 8-metoksy-kinolonkarboksylsyrer - Google Patents

Fremgangsmate for fremstilling av 8-metoksy-kinolonkarboksylsyrer Download PDF

Info

Publication number: NO315748B1
Authority: NO; Norway
Prior art keywords: solvent; equivalents; formula; reaction; compound
Prior art date: 1997-11-24

Application number

NO20002637A

Other languages

English (en)

Norwegian (no)

Other versions

NO20002637L (no

NO20002637D0 (no

Inventor

Klaus-Helmut Mohrs

Herbert Diehl

Reinhold Gehring

Werner Heilmann

Original Assignee

Bayer Ag

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.)

1997-11-24

Filing date

2000-05-23

Publication date

2003-10-20

2000-05-23 Application filed by Bayer Ag filed Critical Bayer Ag

2000-05-23 Publication of NO20002637L publication Critical patent/NO20002637L/no

2000-05-23 Publication of NO20002637D0 publication Critical patent/NO20002637D0/no

2003-10-20 Publication of NO315748B1 publication Critical patent/NO315748B1/no

Links

238000000034 method Methods 0.000 title claims description 42
238000002360 preparation method Methods 0.000 title claims description 11
ZOCSBJTWWJARJQ-UHFFFAOYSA-N 8-methoxy-2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=C(C(O)=O)C(=O)NC2=C1C=CC=C2OC ZOCSBJTWWJARJQ-UHFFFAOYSA-N 0.000 title description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 26
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
239000002904 solvent Substances 0.000 claims description 21
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 19
229910052700 potassium Chemical group 0.000 claims description 19
239000011591 potassium Chemical group 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 15
-1 FCH2-CH2- Chemical group 0.000 claims description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
235000019445 benzyl alcohol Nutrition 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
238000001035 drying Methods 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
238000000746 purification Methods 0.000 claims description 4
238000001953 recrystallisation Methods 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
238000001914 filtration Methods 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
UBIKHJZIEKPIBU-UHFFFAOYSA-N 3-oxo-2h-quinoline-2-carboxylic acid Chemical class C1=CC=CC2=CC(=O)C(C(=O)O)N=C21 UBIKHJZIEKPIBU-UHFFFAOYSA-N 0.000 claims 3
125000000217 alkyl group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 13
238000010992 reflux Methods 0.000 description 13
IDIIJJHBXUESQI-DFIJPDEKSA-N moxifloxacin hydrochloride Chemical compound Cl.COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 IDIIJJHBXUESQI-DFIJPDEKSA-N 0.000 description 11
239000013078 crystal Substances 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000000725 suspension Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 4
150000004682 monohydrates Chemical class 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical group C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000010534 nucleophilic substitution reaction Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
229960003237 betaine Drugs 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
XUBOMFCQGDBHNK-JTQLQIEISA-N (S)-gatifloxacin Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCN[C@@H](C)C1 XUBOMFCQGDBHNK-JTQLQIEISA-N 0.000 description 1
RPHLUJOQGYWPIF-OAPXFOCYSA-N 7-[(4as,7as)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-8-methoxy-3,4-dioxo-2h-quinoline-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=2C(OC)=C(N3C[C@H]4NCCC[C@H]4C3)C(F)=CC=2C(=O)C(=O)C(C(O)=O)N1C1CC1 RPHLUJOQGYWPIF-OAPXFOCYSA-N 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical group C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012467 final product Substances 0.000 description 1
XUBOMFCQGDBHNK-UHFFFAOYSA-N gatifloxacin Chemical compound FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCNC(C)C1 XUBOMFCQGDBHNK-UHFFFAOYSA-N 0.000 description 1
229960003923 gatifloxacin Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- 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

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Environmental Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Quinoline Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO20002637A 1997-11-24 2000-05-23 Fremgangsmate for fremstilling av 8-metoksy-kinolonkarboksylsyrer NO315748B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19751948A DE19751948A1 (de)	1997-11-24	1997-11-24	Verfahren zur Herstellung von 8-Methoxy-Chinoloncarbonsäuren
PCT/EP1998/007237 WO1999026940A2 (fr)	1997-11-24	1998-11-12	Procede de production d'acides carboxyliques de 8-methoxy-quinolone

Publications (3)

Publication Number	Publication Date
NO20002637L NO20002637L (no)	2000-05-23
NO20002637D0 NO20002637D0 (no)	2000-05-23
NO315748B1 true NO315748B1 (no)	2003-10-20

Family

ID=7849617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20002637A NO315748B1 (no)	1997-11-24	2000-05-23	Fremgangsmate for fremstilling av 8-metoksy-kinolonkarboksylsyrer

Country Status (41)

Country	Link
US (2)	US6897315B2 (fr)
EP (1)	EP1034173B1 (fr)
JP (1)	JP4445667B2 (fr)
KR (1)	KR100589549B1 (fr)
CN (2)	CN1151151C (fr)
AR (1)	AR016694A1 (fr)
AT (1)	ATE294169T1 (fr)
AU (1)	AU732977B2 (fr)
BG (1)	BG64532B1 (fr)
BR (1)	BRPI9814894B8 (fr)
CA (2)	CA2311540C (fr)
CO (1)	CO5011069A1 (fr)
CU (1)	CU22953A3 (fr)
CZ (1)	CZ297212B6 (fr)
DE (2)	DE19751948A1 (fr)
DK (1)	DK1034173T3 (fr)
EE (1)	EE04281B1 (fr)
ES (1)	ES2241185T3 (fr)
HK (2)	HK1034080A1 (fr)
HN (1)	HN1998000179A (fr)
HR (1)	HRP20000332B1 (fr)
HU (1)	HU228337B1 (fr)
ID (1)	ID26840A (fr)
IL (1)	IL135866A0 (fr)
IN (1)	IN189753B (fr)
MY (1)	MY129324A (fr)
NO (1)	NO315748B1 (fr)
NZ (1)	NZ504657A (fr)
PE (1)	PE20000007A1 (fr)
PL (1)	PL192461B1 (fr)
PT (1)	PT1034173E (fr)
RU (1)	RU2219175C2 (fr)
SI (1)	SI1034173T1 (fr)
SK (1)	SK285492B6 (fr)
SV (1)	SV1998000139A (fr)
TR (1)	TR200001472T2 (fr)
TW (1)	TW513427B (fr)
UA (1)	UA56286C2 (fr)
UY (1)	UY25265A1 (fr)
WO (1)	WO1999026940A2 (fr)
ZA (1)	ZA9810669B (fr)

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US6608078B2 (en)	2000-05-08	2003-08-19	Wockhardt Limited	Antibacterial chiral 8-(substituted piperidino)-benzo [i,j] quinolizines, processes, compositions and methods of treatment
US7098219B2 (en)	2000-08-01	2006-08-29	Wockhart Limited	Inhibitors of cellular efflux pumps of microbes
US6964966B2 (en)	2001-04-25	2005-11-15	Wockhardt Limited	Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
US6878713B2 (en)	2001-04-25	2005-04-12	Wockhardt Limited	Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
WO2003099815A1 (fr)	2002-05-28	2003-12-04	Wockhardt Limited	Forme cristalline de sel d'arginine de fluoroquinolone
CA2521398C (fr) *	2003-04-09	2011-03-22	Dr. Reddy's Laboratories Limited	Forme cristalline iii de chlorhydrate de moxifloxacine anhydre et procede de preparation de cette derniere
EP1651630A1 (fr) *	2003-08-05	2006-05-03	Matrix Laboratories Ltd	Procede ameliore permettant de preparer un hydrochlorure de moxifloxacine
DE60314920T2 (de)	2003-09-04	2008-03-13	Wockhardt Ltd.	Benzochinolizin-2-carbonsäureargininsalz- tetrahydrat
ITMI20032259A1 (it) *	2003-11-20	2005-05-21	Chemi Spa	Nuovo polimorfo dell'acido 1-ciclopropil-7-(s,s-2,8-diazabciclo-4.3.0-non-8-il)-6-fluoro-1,4-diidro-8-metossi-4-oxo-chinolin carbossilico cloridrato e metodi per la sua preparazione
US7759362B2 (en) *	2004-04-21	2010-07-20	Institut Of Medicinal Biotechnology Chinese Academy Of Medical Sciences	Quinolonecarboxylic acid compounds, preparation methods and pharmaceutical uses thereof
WO2006134491A2 (fr) *	2005-06-14	2006-12-21	Aurobindo Pharma Limited	Nouvelle forme cristalline d'hydrochlorure de moxifloxacine et procede de preparation de cette derniere
ES2311391B1 (es) *	2007-02-07	2009-12-22	Quimica Sintetica, S.A.	Forma cristalina de moxifloxacino base.
EP2154137A1 (fr)	2008-08-04	2010-02-17	Chemo Ibérica, S.A.	Formule cristalline à base de moxifloxacine
IT1393337B1 (it)	2009-03-06	2012-04-20	Italiana Sint Spa	Sintesi di (4as, 7as)-ottaidro-1h-pirrolo[3,4-b]piridina
IT1398952B1 (it)	2010-03-19	2013-03-28	F S I Fabbrica Italiana Sint	Processo di preparazione della moxifloxacina e suoi sali
CN102030751B (zh) *	2010-12-01	2012-11-21	上虞京新药业有限公司	一种盐酸莫西沙星的结晶工艺
CN104447742A (zh) *	2014-11-17	2015-03-25	安徽美诺华药物化学有限公司	一种喹诺酮衍生物的制备方法
CN104370907A (zh) *	2014-11-17	2015-02-25	安徽美诺华药物化学有限公司	喹诺酮衍生物的制备方法
CN104370906A (zh) *	2014-11-17	2015-02-25	安徽美诺华药物化学有限公司	氟喹诺酮衍生物的制备方法
CN104447741A (zh) *	2014-11-17	2015-03-25	安徽美诺华药物化学有限公司	一种氟喹诺酮衍生物的制备方法

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PT77267B (en) *	1982-09-07	1986-03-21	Lilly Co Eli	Improved process for preparing novel octahydrobenz <f> isoquinolines or compounds relating thereto
IE55898B1 (en) *	1982-09-09	1991-02-14	Warner Lambert Co	Antibacterial agents
JPH089597B2 (ja) *	1986-01-21	1996-01-31	杏林製薬株式会社	選択毒性に優れた８‐アルコキシキノロンカルボン酸およびその塩並びにその製造方法
JPS62205060A (ja) *	1986-03-04	1987-09-09	Kyorin Pharmaceut Co Ltd	８位置換キノロンカルボン酸誘導体
NO871333L (no) *	1986-03-31	1987-10-01	Sankyo Co	Kinolin-3-karboksylsyrederivater, fremgangsmaate til fremstilling og anvendelse derav.
EP0342675B1 (fr) *	1988-05-19	1995-01-25	Chugai Seiyaku Kabushiki Kaisha	Dérivés de l'acide quinolonecarboxylique
DE3906365A1 (de)	1988-07-15	1990-01-18	Bayer Ag	7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe
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JPH05117238A (ja)	1991-10-23	1993-05-14	Chugai Pharmaceut Co Ltd	キノロンカルボン酸誘導体の製造方法及びその合成中間体
TW209865B (fr)	1992-01-10	1993-07-21	Bayer Ag
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DE4232172A1 (de)	1992-09-25	1994-03-31	Bayer Ag	7-(Aminomethyl-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)chinolon- und Naphthyridoncarbonsäure-Derivate
DE4234078A1 (de) *	1992-10-09	1994-04-14	Bayer Ag	Chinoloncarbonsäuren
DE4234330A1 (de)	1992-10-12	1994-04-14	Bayer Ag	Chinoloncarbonsäuren
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KR950018003A (ko) *	1993-12-09	1995-07-22	스미스클라인 비참 피엘씨	신규한 퀴놀론 유도체 및 그의 제조 방법
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WO1997027856A1 (fr) *	1996-01-31	1997-08-07	Sankyo Company, Limited	Medicaments pour prevenir ou soigner le sida

1997
- 1997-11-24 DE DE19751948A patent/DE19751948A1/de not_active Withdrawn
1998
- 1998-11-12 PT PT98959874T patent/PT1034173E/pt unknown
- 1998-11-12 DE DE59812758T patent/DE59812758D1/de not_active Expired - Lifetime
- 1998-11-12 AU AU15619/99A patent/AU732977B2/en not_active Expired
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- 1998-11-12 IL IL13586698A patent/IL135866A0/xx not_active IP Right Cessation
- 1998-11-12 AT AT98959874T patent/ATE294169T1/de active
- 1998-11-12 RU RU2000116546/04A patent/RU2219175C2/ru active
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- 1998-11-12 CA CA2711645A patent/CA2711645C/fr not_active Expired - Lifetime
- 1998-11-12 WO PCT/EP1998/007237 patent/WO1999026940A2/fr active IP Right Grant
- 1998-11-12 PL PL341088A patent/PL192461B1/pl unknown
- 1998-11-12 HU HU0004337A patent/HU228337B1/hu active Protection Beyond IP Right Term
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- 1998-11-12 EP EP98959874A patent/EP1034173B1/fr not_active Expired - Lifetime
- 1998-11-12 SI SI9830772T patent/SI1034173T1/xx unknown
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- 1998-12-11 UA UA2000063686A patent/UA56286C2/uk unknown
2000
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2002
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2003
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Also Published As

Publication number	Publication date
ID26840A (id)	2001-02-15
TW513427B (en)	2002-12-11
AR016694A1 (es)	2001-07-25
CU22953A3 (es)	2004-06-21
WO1999026940A2 (fr)	1999-06-03
EE200000241A (et)	2001-06-15
DE59812758D1 (de)	2005-06-02
IL135866A0 (en)	2001-05-20
KR100589549B1 (ko)	2006-06-14
EP1034173B1 (fr)	2005-04-27
JP4445667B2 (ja)	2010-04-07
ZA9810669B (en)	1999-05-26
EE04281B1 (et)	2004-04-15
NO20002637L (no)	2000-05-23
ES2241185T3 (es)	2005-10-16
SK7482000A3 (en)	2000-10-09
AU732977B2 (en)	2001-05-03
WO1999026940A3 (fr)	1999-08-12
SV1998000139A (es)	1999-04-13
NZ504657A (en)	2001-04-27
MY129324A (en)	2007-03-30
SI1034173T1 (en)	2005-10-31
HU228337B1 (en)	2013-03-28
BRPI9814894B1 (pt)	2011-10-18
HRP20000332A2 (en)	2001-04-30
NO20002637D0 (no)	2000-05-23
CO5011069A1 (es)	2001-02-28
EP1034173A2 (fr)	2000-09-13
CN1151151C (zh)	2004-05-26
US20050209276A1 (en)	2005-09-22
PL341088A1 (en)	2001-03-26
DK1034173T3 (da)	2005-07-25
JP2001524477A (ja)	2001-12-04
HN1998000179A (es)	1999-02-09
PT1034173E (pt)	2005-08-31
PE20000007A1 (es)	2000-03-05
RU2219175C2 (ru)	2003-12-20
HK1056169A1 (en)	2004-02-06
CA2311540A1 (fr)	1999-06-03
HRP20000332B1 (en)	2009-01-31
BG64532B1 (bg)	2005-06-30
SK285492B6 (sk)	2007-02-01
HK1034080A1 (en)	2001-10-12
AU1561999A (en)	1999-06-15
BRPI9814894B8 (pt)	2021-07-06
CA2311540C (fr)	2011-06-14
CN1418879A (zh)	2003-05-21
US6897315B2 (en)	2005-05-24
TR200001472T2 (tr)	2002-06-21
CA2711645C (fr)	2016-04-26
BRPI9814894A (pt)	2000-10-03
KR20010032361A (ko)	2001-04-16
US7115744B2 (en)	2006-10-03
DE19751948A1 (de)	1999-05-27
CZ297212B6 (cs)	2006-10-11
CZ20001926A3 (cs)	2000-11-15
ATE294169T1 (de)	2005-05-15
PL192461B1 (pl)	2006-10-31
UA56286C2 (uk)	2003-05-15
UY25265A1 (es)	1999-07-19
IN189753B (fr)	2003-04-19
HUP0004337A3 (en)	2004-07-28
CA2711645A1 (fr)	1999-06-03
CN1279683A (zh)	2001-01-10
BG104467A (en)	2001-08-31
CN1200938C (zh)	2005-05-11
HUP0004337A2 (hu)	2001-10-28
US20030208069A1 (en)	2003-11-06

Legal Events

Date	Code	Title	Description
2013-06-17	CHAD	Change of the owner's name or address (par. 44 patent law, par. patentforskriften)	Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE
2018-12-10	MK1K	Patent expired

Publication	Publication Date	Title
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