KR20150048920A - 목시플록사신 염산염의 합성방법 - Google Patents
목시플록사신 염산염의 합성방법 Download PDFInfo
- Publication number
- KR20150048920A KR20150048920A KR1020157010216A KR20157010216A KR20150048920A KR 20150048920 A KR20150048920 A KR 20150048920A KR 1020157010216 A KR1020157010216 A KR 1020157010216A KR 20157010216 A KR20157010216 A KR 20157010216A KR 20150048920 A KR20150048920 A KR 20150048920A
- Authority
- KR
- South Korea
- Prior art keywords
- moxifloxacin hydrochloride
- crystalline form
- moxifloxacin
- hydrochloride according
- rti
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- 229960005112 moxifloxacin hydrochloride Drugs 0.000 title claims abstract description 33
- 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 title claims abstract 15
- 238000000034 method Methods 0.000 title claims description 28
- 230000015572 biosynthetic process Effects 0.000 title abstract description 3
- 238000003786 synthesis reaction Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 229960003702 moxifloxacin Drugs 0.000 claims description 21
- FABPRXSRWADJSP-MEDUHNTESA-N moxifloxacin Chemical compound COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 FABPRXSRWADJSP-MEDUHNTESA-N 0.000 claims description 21
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- 238000001237 Raman spectrum Methods 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 238000002329 infrared spectrum Methods 0.000 claims description 3
- 238000001757 thermogravimetry curve Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- SKZIMSDWAIZNDD-WJMOHVQJSA-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-4-oxoquinoline-3-carboxylic acid;hydrate;hydrochloride Chemical compound O.Cl.COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 SKZIMSDWAIZNDD-WJMOHVQJSA-N 0.000 description 34
- 239000011541 reaction mixture Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000008213 purified water Substances 0.000 description 8
- KSCPLKVBWDOSAI-NKWVEPMBSA-N (4as,7as)-2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCC[C@H]2CNC[C@H]21 KSCPLKVBWDOSAI-NKWVEPMBSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- JFPZXAXJJFRETR-UHFFFAOYSA-N CCCOOOB(O)OOOCCC Chemical compound CCCOOOB(O)OOOCCC JFPZXAXJJFRETR-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 206010057190 Respiratory tract infections Diseases 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- WQJZXSSAMGZVTM-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(F)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 WQJZXSSAMGZVTM-UHFFFAOYSA-N 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- -1 moxifloxacin hydrochloride anhydrides Chemical class 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000606768 Haemophilus influenzae Species 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229940047650 haemophilus influenzae Drugs 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 241000588655 Moraxella catarrhalis Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 241000193998 Streptococcus pneumoniae Species 0.000 description 2
- 241000193996 Streptococcus pyogenes Species 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- XPAOPAPDCRLMTR-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxoquinoline-3-carboxylate Chemical compound C12=C(OC)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 XPAOPAPDCRLMTR-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- GQYBNVXJQVIRGC-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.FC1=CC(C(C(C(O)=O)=CN2C3CC3)=O)=C2C(OC)=C1N1CCNC(C)C1 GQYBNVXJQVIRGC-UHFFFAOYSA-N 0.000 description 1
- VAYISIYCRRTUOV-UHFFFAOYSA-N 1-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2N(OC)C=C(C(O)=O)C(=O)C2=C1 VAYISIYCRRTUOV-UHFFFAOYSA-N 0.000 description 1
- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 1
- FABPRXSRWADJSP-UHFFFAOYSA-N 7-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-1-ium-6-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylate Chemical compound COC1=C(N2CC3NCCCC3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 FABPRXSRWADJSP-UHFFFAOYSA-N 0.000 description 1
- CDGYPATWKVOBIY-UHFFFAOYSA-N 8-methoxy-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound N1C=C(C(O)=O)C(=O)C2=C1C(OC)=CC=C2 CDGYPATWKVOBIY-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- DNROVSRDRPUIEN-VHSXEESVSA-N C(CC)O[C@]12NCCC[C@H]2CNC1 Chemical compound C(CC)O[C@]12NCCC[C@H]2CNC1 DNROVSRDRPUIEN-VHSXEESVSA-N 0.000 description 1
- 102100034741 Cyclin-dependent kinase 20 Human genes 0.000 description 1
- 241000606766 Haemophilus parainfluenzae Species 0.000 description 1
- 101500014379 Lymnaea stagnalis Ovulation hormone Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 201000005010 Streptococcus pneumonia Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229940124307 fluoroquinolone Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 235000019589 hardness Nutrition 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1879MU2006 | 2006-11-13 | ||
| IN1879/MUM/2006 | 2006-11-13 | ||
| PCT/GB2007/004320 WO2008059223A2 (en) | 2006-11-13 | 2007-11-13 | Process for the synthesis of moxifloxacin hydrochloride |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097012171A Division KR101539561B1 (ko) | 2006-11-13 | 2007-11-13 | 목시플록사신 염산염의 합성방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150048920A true KR20150048920A (ko) | 2015-05-07 |
Family
ID=38947366
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097012171A Expired - Fee Related KR101539561B1 (ko) | 2006-11-13 | 2007-11-13 | 목시플록사신 염산염의 합성방법 |
| KR1020157010216A Ceased KR20150048920A (ko) | 2006-11-13 | 2007-11-13 | 목시플록사신 염산염의 합성방법 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097012171A Expired - Fee Related KR101539561B1 (ko) | 2006-11-13 | 2007-11-13 | 목시플록사신 염산염의 합성방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8198451B2 (enExample) |
| EP (2) | EP2089388B1 (enExample) |
| JP (2) | JP2010509305A (enExample) |
| KR (2) | KR101539561B1 (enExample) |
| AU (1) | AU2007320997B2 (enExample) |
| CA (1) | CA2669427A1 (enExample) |
| IN (1) | IN2014MN02582A (enExample) |
| NZ (1) | NZ576929A (enExample) |
| WO (1) | WO2008059223A2 (enExample) |
| ZA (1) | ZA200903889B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ576929A (en) | 2006-11-13 | 2012-07-27 | Cipla Ltd | Crystalline anhydrous form C of moxifloxacin hydrochloride |
| CN101817820B (zh) * | 2009-07-30 | 2011-10-05 | 重庆博腾制药科技股份有限公司 | 一种盐酸莫西沙星的合成方法 |
| WO2011121596A2 (en) * | 2010-04-01 | 2011-10-06 | Neuland Laboratories Ltd. | Crystal modification of moxifloxacin hydrochloride |
| CN102309458B (zh) * | 2010-07-09 | 2016-02-03 | 北京圣医耀科技发展有限责任公司 | 海藻酸钠交联莫西沙星缓释微球、其制备方法和用途以及含有所述微球的血管靶向栓塞剂 |
| CN102617622B (zh) * | 2011-01-31 | 2016-06-15 | 深圳信立泰药业股份有限公司 | 一种制备莫西沙星或其可药用盐及其中间体的方法 |
| CN102276603B (zh) * | 2011-07-14 | 2012-10-24 | 福建省福抗药业股份有限公司 | 一种盐酸莫西沙星的清洁制备方法 |
| ITTO20110705A1 (it) | 2011-07-29 | 2013-01-30 | Italiana Sint Spa | Procedimento di preparazione della moxifloxacina cloridrato e relativi intermedi |
| CN102659761B (zh) * | 2012-04-27 | 2017-10-10 | 常州市亚邦医药研究所有限公司 | 盐酸贝西沙星的制备方法 |
| FR2992218B1 (fr) | 2012-06-22 | 2015-01-23 | Rivopharm Sa | Composition pharmaceutique de chlorhydrate de moxifloxacine et procede de preparation |
| EP2928892B1 (en) | 2012-12-04 | 2018-03-21 | Mankind Pharma Ltd. | An improved process for the preparation of moxifloxacin hydrochloride |
| CN103102341A (zh) * | 2012-12-14 | 2013-05-15 | 浙江普洛康裕制药有限公司 | 一种巴洛沙星二水合物的制备方法 |
| 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 |
| CN104098561B (zh) * | 2013-04-10 | 2016-01-20 | 山东省生物医药科学院 | 一种适合工业化生产的制备高光学纯度盐酸莫西沙星的方法 |
| CN104031043B (zh) * | 2014-05-28 | 2016-03-16 | 成都克莱蒙医药科技有限公司 | 一种盐酸莫西沙星合成方法 |
| 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 |
| CN105237535A (zh) * | 2015-11-15 | 2016-01-13 | 青岛麦瑞特医药技术有限公司 | 一种制备盐酸莫西沙星的方法 |
| CN105669671A (zh) * | 2016-03-10 | 2016-06-15 | 陈红 | 一种盐酸莫西沙星的制备方法 |
| CN110143959B (zh) * | 2019-05-10 | 2022-04-26 | 广西两面针亿康药业股份有限公司 | 一种盐酸莫西沙星的制备方法 |
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| SI8810667A8 (en) * | 1987-04-08 | 1996-04-30 | Chinoin Gyogyszer Es Vegyeszet | Anhydride of quinoline carboxylic acid of boron acid and process for their production. |
| 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 |
| JPH0778065B2 (ja) * | 1990-07-06 | 1995-08-23 | 杏林製薬株式会社 | (6,7―置換―8―アルコキシ―1―シクロプロピル―1,4―ジヒドロ―4―オキソ―3―キノリンカルボン酸―o▲上3▼,o▲上4▼)ビス(アシルオキシ―o)ホウ素化合物及びその塩並びにその製造方法 |
| TW209865B (enExample) | 1992-01-10 | 1993-07-21 | Bayer Ag | |
| ES2077490B1 (es) * | 1992-11-18 | 1996-10-16 | Marga Investigacion | Esteres trimetilsililicos y solvatos de quelatos de acidos quinolin-3-carboxilicos. preparacion y aplicacion al proceso de quinolonas. |
| DE4342186A1 (de) | 1993-12-10 | 1995-06-14 | Bayer Ag | Eintopfverfahren zur Herstellung von 3-Chinoloncarbonsäurederivaten |
| 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 |
| DE19821039A1 (de) * | 1998-05-11 | 1999-11-18 | Bayer Ag | Verfahren zur Herstellung von (S,S)-Benzyl-2,8-diazabicyclo[4.3.0]nonan |
| US6174878B1 (en) * | 1999-08-31 | 2001-01-16 | Alcon Laboratories, Inc. | Topical use of kappa opioid agonists to treat otic pain |
| CN1184221C (zh) * | 2001-08-08 | 2005-01-12 | 中国医学科学院医药生物技术研究所 | 有7-(7-氨甲基-5-氮杂螺[2,4]庚烷)取代基的新喹啉羧酸衍生物及其制备方法 |
| EP2113505A1 (en) | 2003-04-09 | 2009-11-04 | Dr. Reddy's Laboratories, Ltd. | A crystalline form III of anhydrous moxifloxacin hydrochloride and processes for the preparation thereof |
| US20060264635A1 (en) | 2003-08-05 | 2006-11-23 | Chava Satyanarayana | Process for the preparation of moxifloxacin hydrochloride |
| ES2319125T3 (es) | 2003-11-20 | 2009-05-04 | Chemi S.P.A. | Polimorfos del clorhidrato del acido 1-ciclopropil-7-((s,s)-2,8-diazadiciclo(4.3.0)-non-8-il)-6-fluoro-1,4-dihidro-8-metoxi-4-oxo-3-quinolina carboxilico y metodos para la preparacion de los mismos. |
| US7320006B2 (en) * | 2004-11-12 | 2008-01-15 | Computer Sciences Corporation | Hierarchical database management |
| WO2006134491A2 (en) * | 2005-06-14 | 2006-12-21 | Aurobindo Pharma Limited | New crystalline form of moxifloxacin hydrochloride and process for its preparation |
| WO2007010555A2 (en) | 2005-07-15 | 2007-01-25 | Msn Laboratories Limited | Novel crystalline forms of moxifloxacin hydrochloride and process for preparation thereof |
| ES2284380B1 (es) * | 2006-03-10 | 2008-11-01 | Quimica Sintetica S.A. | Procedimiento para la preparacion de moxifloxacino y moxifloxacino clorhidrato. |
| NZ576929A (en) | 2006-11-13 | 2012-07-27 | Cipla Ltd | Crystalline anhydrous form C of moxifloxacin hydrochloride |
-
2007
- 2007-11-13 NZ NZ576929A patent/NZ576929A/en not_active IP Right Cessation
- 2007-11-13 KR KR1020097012171A patent/KR101539561B1/ko not_active Expired - Fee Related
- 2007-11-13 IN IN2582MUN2014 patent/IN2014MN02582A/en unknown
- 2007-11-13 WO PCT/GB2007/004320 patent/WO2008059223A2/en not_active Ceased
- 2007-11-13 JP JP2009535810A patent/JP2010509305A/ja active Pending
- 2007-11-13 EP EP07824549.5A patent/EP2089388B1/en not_active Not-in-force
- 2007-11-13 AU AU2007320997A patent/AU2007320997B2/en not_active Ceased
- 2007-11-13 EP EP12159510A patent/EP2474547A3/en not_active Withdrawn
- 2007-11-13 US US12/514,552 patent/US8198451B2/en not_active Expired - Fee Related
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- 2007-11-13 KR KR1020157010216A patent/KR20150048920A/ko not_active Ceased
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| EP2089388A2 (en) | 2009-08-19 |
| AU2007320997B2 (en) | 2012-11-08 |
| JP2014122223A (ja) | 2014-07-03 |
| CA2669427A1 (en) | 2008-05-22 |
| AU2007320997A1 (en) | 2008-05-22 |
| US8198451B2 (en) | 2012-06-12 |
| JP2010509305A (ja) | 2010-03-25 |
| ZA200903889B (en) | 2010-03-31 |
| KR101539561B1 (ko) | 2015-07-27 |
| EP2089388B1 (en) | 2014-01-29 |
| JP5774732B2 (ja) | 2015-09-09 |
| US20100152229A1 (en) | 2010-06-17 |
| EP2474547A3 (en) | 2012-07-25 |
| EP2474547A2 (en) | 2012-07-11 |
| IN2014MN02582A (enExample) | 2015-09-11 |
| KR20090090337A (ko) | 2009-08-25 |
| NZ576929A (en) | 2012-07-27 |
| WO2008059223A2 (en) | 2008-05-22 |
| WO2008059223A3 (en) | 2008-07-31 |
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