CZ289076B6 - Enantiomery derivátů kyseliny chinolonkarboxylové a nafthyridonkarboxylové - Google Patents
Enantiomery derivátů kyseliny chinolonkarboxylové a nafthyridonkarboxylové Download PDFInfo
- Publication number
- CZ289076B6 CZ289076B6 CS19923966A CS396692A CZ289076B6 CZ 289076 B6 CZ289076 B6 CZ 289076B6 CS 19923966 A CS19923966 A CS 19923966A CS 396692 A CS396692 A CS 396692A CZ 289076 B6 CZ289076 B6 CZ 289076B6
- Authority
- CZ
- Czechia
- Prior art keywords
- diazabicyclo
- cyclopropyl
- acid
- oxo
- dihydro
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 28
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title claims description 14
- -1 naphthyridone carboxylic acid derivatives Chemical class 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 34
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
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- 230000008569 process Effects 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- YCAZALSUJDPQPP-UHFFFAOYSA-N 4-oxo-3h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)C=NC2=C1 YCAZALSUJDPQPP-UHFFFAOYSA-N 0.000 claims description 5
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- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
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- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 claims description 3
- BEOAQNGVMXFVRN-JOYOIKCWSA-N 7-[(4as,7as)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-5,6,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3C[C@H]4NCCC[C@H]4C3)=C(F)C(F)=C2C(=O)C(C(=O)O)=CN1C1CC1 BEOAQNGVMXFVRN-JOYOIKCWSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
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- 239000004480 active ingredient Substances 0.000 claims 1
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- 150000002357 guanidines Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 9
- 239000003242 anti bacterial agent Substances 0.000 abstract description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- 239000000243 solution Substances 0.000 description 46
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 40
- 238000000354 decomposition reaction Methods 0.000 description 39
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- 239000000203 mixture Substances 0.000 description 33
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 32
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- 239000002244 precipitate Substances 0.000 description 26
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 125000006414 CCl Chemical group ClC* 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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- 239000000706 filtrate Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 16
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- CJIVCSBYIRBJSG-UHFFFAOYSA-N pyrrolidine-3,3-diol Chemical compound OC1(O)CCNC1 CJIVCSBYIRBJSG-UHFFFAOYSA-N 0.000 description 1
- DASZTFGYDXJWBT-UHFFFAOYSA-N quinoline-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(C(=O)O)=CC=C21 DASZTFGYDXJWBT-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- YVZVETBYUFHWDL-UHFFFAOYSA-N quinoline-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CC2=CC(C(=O)O)=CN=C21 YVZVETBYUFHWDL-UHFFFAOYSA-N 0.000 description 1
- KVROVDQWRUAIID-UHFFFAOYSA-N quinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C(=O)O)=CN=C21 KVROVDQWRUAIID-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 208000015339 staphylococcus aureus infection Diseases 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Fodder In General (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4200414A DE4200414A1 (de) | 1992-01-10 | 1992-01-10 | Chinolon- und naphthyridon-carbonsaeure-derivate |
| DE4208792A DE4208792A1 (de) | 1992-03-19 | 1992-03-19 | Enantiomerenreine chinolincarbonsaeure-derivate |
| DE4208789A DE4208789A1 (de) | 1992-03-19 | 1992-03-19 | Enantiomerenreine chinolincarbonsaeure-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ396692A3 CZ396692A3 (en) | 1993-08-11 |
| CZ289076B6 true CZ289076B6 (cs) | 2001-10-17 |
Family
ID=27203290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS19923966A CZ289076B6 (cs) | 1992-01-10 | 1992-12-29 | Enantiomery derivátů kyseliny chinolonkarboxylové a nafthyridonkarboxylové |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0550903A1 (en, 2012) |
| JP (3) | JPH05271229A (en, 2012) |
| KR (1) | KR100251886B1 (en, 2012) |
| CN (3) | CN1043142C (en, 2012) |
| AU (1) | AU669502B2 (en, 2012) |
| CA (1) | CA2086914C (en, 2012) |
| CZ (1) | CZ289076B6 (en, 2012) |
| FI (3) | FI104174B1 (en, 2012) |
| HU (1) | HU219488B (en, 2012) |
| MX (1) | MX9207604A (en, 2012) |
| MY (1) | MY115416A (en, 2012) |
| NO (1) | NO301420B1 (en, 2012) |
| NZ (1) | NZ245640A (en, 2012) |
| PL (1) | PL174853B1 (en, 2012) |
| SK (3) | SK282971B6 (en, 2012) |
| TW (1) | TW209865B (en, 2012) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04445A (ja) | 1990-04-17 | 1992-01-06 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| EP0458131B1 (en) | 1990-05-09 | 1997-08-06 | Fuji Photo Film Co., Ltd. | Photographic processing composition and processing method using the same |
| DE4121214A1 (de) * | 1991-06-27 | 1993-01-14 | Bayer Ag | 7-azaisoindolinyl-chinolon- und -naphthyridoncarbonsaeure-derivate |
| CA2112165C (en) * | 1992-12-25 | 2003-04-08 | Makoto Takemura | Bicyclic amine derivatives |
| KR0148277B1 (ko) * | 1993-01-18 | 1998-11-02 | 채영복 | 신규한 플루오르퀴놀론계 유도체 및 그의 제조방법 |
| DE4301246A1 (de) * | 1993-01-19 | 1994-07-21 | Bayer Ag | Chinolon- und Naphthyridoncarbonsäurederivate |
| JP3372994B2 (ja) | 1993-06-11 | 2003-02-04 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料の処理方法 |
| DE4329600A1 (de) * | 1993-09-02 | 1995-03-09 | Bayer Ag | Pyrido [1,2,3-d,e] [1,3,4] benzoxadiazinderivate |
| KR950018003A (ko) * | 1993-12-09 | 1995-07-22 | 스미스클라인 비참 피엘씨 | 신규한 퀴놀론 유도체 및 그의 제조 방법 |
| DE4342186A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Eintopfverfahren zur Herstellung von 3-Chinoloncarbonsäurederivaten |
| DE4418510A1 (de) * | 1994-05-27 | 1995-11-30 | Bayer Ag | 1,9-überbrückte Thiazolol[3,4-a]chinolinderivate |
| AU6221296A (en) * | 1995-06-07 | 1996-12-30 | Bayer Aktiengesellschaft | Testing device for determining the susceptibility of microor ganisms to inhibitory agents |
| DE19546249A1 (de) * | 1995-12-12 | 1997-06-19 | Bayer Ag | Neue Kristallmodifikation des 1-Cyclopropyl-7-([S,S]-2,8-diazabicyclo[4,3,0]non-8-yl)-6-fluor-1,4-dihydro-8-methoxy-4-oxo-3-chinolincarbonsäure Hydrochlorid (CDCH), Verfahren zu dessen Herstellung und diese enthaltende pharmazeutische Zubereitungen |
| DE19652239A1 (de) * | 1996-12-16 | 1998-06-18 | Bayer Ag | Verwendung von 7-(2-Oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-chinolon- und -naphthyridoncarbonsäure-Derivaten zur Therapie von Helicobacter-pylori-Infektionen und den damit assoziierten gastroduodenalen Erkrankungen |
| DE19735198A1 (de) * | 1997-08-14 | 1999-02-18 | Bayer Ag | Verfahren zur Racematspaltung von cis- und trans-Pyrrolopiperidin |
| CN1623533A (zh) * | 1997-09-25 | 2005-06-08 | 拜尔公司 | 控释活性化合物的药物制剂 |
| DE19751948A1 (de) * | 1997-11-24 | 1999-05-27 | Bayer Ag | Verfahren zur Herstellung von 8-Methoxy-Chinoloncarbonsäuren |
| DE19821039A1 (de) * | 1998-05-11 | 1999-11-18 | Bayer Ag | Verfahren zur Herstellung von (S,S)-Benzyl-2,8-diazabicyclo[4.3.0]nonan |
| US6395746B1 (en) | 1998-09-30 | 2002-05-28 | Alcon Manufacturing, Ltd. | Methods of treating ophthalmic, otic and nasal infections and attendant inflammation |
| US6509327B1 (en) | 1998-09-30 | 2003-01-21 | Alcon Manufacturing, Ltd. | Compositions and methods for treating otic, ophthalmic and nasal infections |
| US6716830B2 (en) | 1998-09-30 | 2004-04-06 | Alcon, Inc. | Ophthalmic antibiotic compositions containing moxifloxacin |
| AR020661A1 (es) * | 1998-09-30 | 2002-05-22 | Alcon Lab Inc | Una composicion farmaceutica topica oftalmica, otica o nasal y el uso de la misma para la manufactura de un medicamento |
| UA72483C2 (en) * | 1998-11-10 | 2005-03-15 | Moxifloxacin-containing pharmaceutical preparation and method for its manufacture | |
| JP4694669B2 (ja) | 1999-03-17 | 2011-06-08 | 第一三共株式会社 | 医薬組成物 |
| DE19927412A1 (de) | 1999-06-16 | 2000-12-21 | Bayer Ag | Verfahren zur Enantiomerenanreicherung von cis-8-Benzyl-7,9-dioxo-2,8-diazabicyclo [4.3.0]nonan |
| DE19931115A1 (de) * | 1999-07-06 | 2001-01-11 | Bayer Ag | Racemisierung von R, S-Dioxo-Benzylpyrrolopiperidin |
| DE19962470A1 (de) * | 1999-12-22 | 2001-07-12 | Schulz Hans Herrmann | Verwendung von Chemotherapeutika |
| DE10226923A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Verfahren zur Enantiomerenanreicherung von cis-8-Benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonan |
| EP1685130B1 (en) * | 2003-11-20 | 2008-12-10 | CHEMI S.p.A. | Polymorphs of 1-cyclopropyl-7-([s,s] - 2,8-diazadicyclo [4.3.0] non-8-yl) -6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid hydrochloride and methods for the preparation thereof |
| 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 |
| CN1244582C (zh) * | 2004-04-21 | 2006-03-08 | 中国医学科学院医药生物技术研究所 | 喹诺酮羧酸类化合物及其制备方法和医药用途 |
| ES2284380B1 (es) * | 2006-03-10 | 2008-11-01 | Quimica Sintetica S.A. | Procedimiento para la preparacion de moxifloxacino y moxifloxacino clorhidrato. |
| WO2008000418A2 (en) | 2006-06-27 | 2008-01-03 | Sandoz Ag | New method for salt preparation |
| EP2474547A3 (en) | 2006-11-13 | 2012-07-25 | Cipla Limited | Process for the Synthesis of Moxifloxacin Hydrochloride |
| WO2008059521A2 (en) * | 2006-11-14 | 2008-05-22 | Msn Laboratories Limited | Novel process for the preparation of moxifloxacin hydrochloride and a novel polymorph of moxifloxacin |
| US7692015B2 (en) | 2007-01-05 | 2010-04-06 | Zheqing Wang | Economical process for preparing (S, S)-2, 8-diazabicyclo[4.3.0]nonane and its enantiomer |
| WO2008102188A1 (en) | 2007-02-22 | 2008-08-28 | Tibor Nagy | Procedure to manufacture and use beer and other types liquids treated with neodimium magnet |
| EP2083010A1 (en) | 2008-01-08 | 2009-07-29 | Chemo Ibérica, S.A. | Polymorphic Forms of Moxifloxacin hydrochloride and processes for preparation thereof |
| EP2154137A1 (en) | 2008-08-04 | 2010-02-17 | Chemo Ibérica, S.A. | Crystalline form of moxifloxacin base |
| IT1393337B1 (it) * | 2009-03-06 | 2012-04-20 | Italiana Sint Spa | Sintesi di (4as, 7as)-ottaidro-1h-pirrolo[3,4-b]piridina |
| EP2423211B1 (en) * | 2009-04-20 | 2014-04-16 | Kaneka Corporation | Processes for producing (1s,6s)- or (1r,6r)-cis-2,8-diazabicyclo[4.3.0]nonane and intermediate thereof |
| IT1398952B1 (it) * | 2010-03-19 | 2013-03-28 | F S I Fabbrica Italiana Sint | Processo di preparazione della moxifloxacina e suoi sali |
| CN101941969B (zh) * | 2010-09-30 | 2012-05-23 | 江苏正大丰海制药有限公司 | 盐酸莫西沙星的制备方法 |
| CN102675308A (zh) * | 2011-03-17 | 2012-09-19 | 苏州中科天马肽工程中心有限公司 | 一种制备8-苄基-2,8-二氮杂二环[4.3.0]壬烷的方法 |
| CN102675307A (zh) * | 2011-03-17 | 2012-09-19 | 苏州中科天马肽工程中心有限公司 | 一种制备手性化合物8-苯乙基-2,8-二氮杂二环[4.3.0]壬烷的方法 |
| ITTO20110705A1 (it) | 2011-07-29 | 2013-01-30 | Italiana Sint Spa | Procedimento di preparazione della moxifloxacina cloridrato e relativi intermedi |
| CN102964346B (zh) * | 2011-09-01 | 2015-04-22 | 中国中化股份有限公司 | 一种制备(S,S)-八氢-6H-吡咯并[3,4-b]吡啶的方法 |
| CN103044418B (zh) * | 2011-10-14 | 2015-02-04 | 上海朴颐化学科技有限公司 | (s,s)-2,8-二氮杂双环[4,3,0]壬烷的不对称合成方法、相关原料及制备方法 |
| CN102408427B (zh) * | 2011-10-22 | 2012-12-12 | 浙江普洛康裕制药有限公司 | 莫西沙星中间体〔1s，6r〕—8—苄基—7，9—二氧—2，8—二氮杂双环［4．3．0］壬烷的制备方法 |
| BRPI1106900A2 (pt) | 2011-12-26 | 2013-11-05 | Ems Sa | Composição farmacêutica sólida compreendendo antibótico da familia das quinolonas e processo de sua obtenção |
| FR2992218B1 (fr) | 2012-06-22 | 2015-01-23 | Rivopharm Sa | Composition pharmaceutique de chlorhydrate de moxifloxacine et procede de preparation |
| US9388178B2 (en) | 2012-12-04 | 2016-07-12 | Mankind Research Centre | Process for the preparation of moxifloxacin hydrochloride |
| CN103012452B (zh) * | 2012-12-25 | 2015-12-02 | 浙江新和成股份有限公司 | 一种莫西沙星及其盐酸盐的制备方法 |
| UA106556C2 (uk) * | 2013-05-13 | 2014-09-10 | Наталья Николаевна Деркач | СПОСІБ ОДЕРЖАННЯ (1-ЦИКЛОПРОПІЛ-6-ФТОР-1,4-ДИГІДРО-8-МЕТОКСІ-7-[(4aS,7aS)-ОКТАГІДРО-6Н-ПІРОЛО[3,4-b]-4-ОКСО-3-ХІНОЛІНКАРБОНОВОЇ КИСЛОТИ |
| CN103724262B (zh) * | 2013-12-10 | 2016-05-18 | 广东省第二人民医院 | 一种氟喹诺酮银化合物及其制备方法和用途 |
| CN104860944A (zh) * | 2015-06-09 | 2015-08-26 | 内蒙古东北六药集团有限公司 | 盐酸莫西沙星的生产方法 |
| CN108872413B (zh) * | 2018-04-27 | 2021-06-08 | 山东齐都药业有限公司 | 检测(s,s)-2,8-二氮杂双环[4,3,0]壬烷中对映异构体含量的方法 |
| CN110627768B (zh) * | 2018-06-22 | 2021-11-09 | 扬子江药业集团有限公司 | 一种莫西沙星降解杂质j的制备方法 |
| CN110183445B (zh) * | 2019-06-28 | 2021-08-24 | 昆明学院 | 莫西沙星及其衍生物的合成方法 |
| RU2713932C1 (ru) * | 2019-10-31 | 2020-02-11 | федеральное государственное автономное образовательное учреждение высшего образования "Казанский (Приволжский) федеральный университет" (ФГАОУ ВО КФУ) | Соединения фторхинолонового ряда на основе производных пиридоксина, обладающие антибактериальными свойствами |
| CN112939849B (zh) * | 2019-12-11 | 2022-05-03 | 浙江新和成股份有限公司 | 一种(s,s)-2,8-二氮杂双环[4.3.0]壬烷中间体及其制备方法和应用 |
| CN110981874A (zh) * | 2020-03-05 | 2020-04-10 | 北京四环生物制药有限公司 | 一种盐酸莫西沙星的制备方法 |
| CN112409352B (zh) * | 2020-11-20 | 2022-05-24 | 华南理工大学 | 一类莫西沙星类药物衍生物及其制备方法和应用 |
| CN112574197B (zh) * | 2020-12-07 | 2021-12-31 | 泰安汉威集团有限公司 | 一种化合物c的手性纯化方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0754229B2 (ja) * | 1987-09-28 | 1995-06-07 | 松下冷機株式会社 | 冷蔵庫 |
| 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 |
| FI901201A7 (fi) * | 1989-03-13 | 1990-09-14 | Bristol Myers Squibb Co | Antibakteeriset 5-substituoidut 1,4-dihydro-4-oksonaftyridiini-3-karboksylaattijohdannaiset ja niiden valmistus |
| DE3910663A1 (de) * | 1989-04-03 | 1990-10-04 | Bayer Ag | 5-alkylchinoloncarbonsaeuren |
| JPH03188080A (ja) * | 1989-12-15 | 1991-08-16 | Banyu Pharmaceut Co Ltd | ピリドンカルボン酸誘導体 |
-
1992
- 1992-10-12 TW TW081108103A patent/TW209865B/zh not_active IP Right Cessation
- 1992-12-22 NO NO924978A patent/NO301420B1/no not_active IP Right Cessation
- 1992-12-28 EP EP92122058A patent/EP0550903A1/de not_active Withdrawn
- 1992-12-29 MX MX9207604A patent/MX9207604A/es unknown
- 1992-12-29 SK SK3966-92A patent/SK282971B6/sk not_active IP Right Cessation
- 1992-12-29 SK SK223-2000A patent/SK285223B6/sk not_active IP Right Cessation
- 1992-12-29 SK SK221-2000A patent/SK285155B6/sk not_active IP Right Cessation
- 1992-12-29 CZ CS19923966A patent/CZ289076B6/cs not_active IP Right Cessation
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1993
- 1993-01-05 JP JP5015917A patent/JPH05271229A/ja active Pending
- 1993-01-06 AU AU31054/93A patent/AU669502B2/en not_active Expired
- 1993-01-07 FI FI930049A patent/FI104174B1/fi not_active IP Right Cessation
- 1993-01-07 CA CA002086914A patent/CA2086914C/en not_active Expired - Lifetime
- 1993-01-08 HU HU9300034A patent/HU219488B/hu unknown
- 1993-01-08 PL PL93297338A patent/PL174853B1/pl unknown
- 1993-01-08 NZ NZ245640A patent/NZ245640A/en not_active IP Right Cessation
- 1993-01-09 CN CN93100215A patent/CN1043142C/zh not_active Expired - Lifetime
- 1993-01-09 KR KR1019930000227A patent/KR100251886B1/ko not_active Expired - Lifetime
- 1993-01-10 MY MYPI93000039A patent/MY115416A/en unknown
-
1997
- 1997-12-20 CN CN97108773A patent/CN1061351C/zh not_active Expired - Lifetime
-
1998
- 1998-05-29 CN CN98109504A patent/CN1075499C/zh not_active Expired - Lifetime
-
1999
- 1999-02-03 FI FI990207A patent/FI110943B/fi not_active IP Right Cessation
-
2002
- 2002-01-11 FI FI20020059A patent/FI113771B/fi not_active IP Right Cessation
- 2002-05-20 JP JP2002144576A patent/JP4111431B2/ja not_active Expired - Lifetime
- 2002-05-20 JP JP2002144273A patent/JP2003026574A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20121229 |
|
| MK4A | Patent expired |
Effective date: 20140621 |