JP2010509305A - モキシフロキサシン塩酸塩の合成方法 - Google Patents
モキシフロキサシン塩酸塩の合成方法 Download PDFInfo
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- JP2010509305A JP2010509305A JP2009535810A JP2009535810A JP2010509305A JP 2010509305 A JP2010509305 A JP 2010509305A JP 2009535810 A JP2009535810 A JP 2009535810A JP 2009535810 A JP2009535810 A JP 2009535810A JP 2010509305 A JP2010509305 A JP 2010509305A
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- Prior art keywords
- moxifloxacin hydrochloride
- moxifloxacin
- hydrochloride form
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- 238000000034 method Methods 0.000 title claims abstract description 39
- 229960005112 moxifloxacin hydrochloride Drugs 0.000 title claims abstract description 25
- 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 21
- 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 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 229960003702 moxifloxacin Drugs 0.000 claims description 25
- 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 25
- 150000001875 compounds Chemical class 0.000 claims description 18
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 14
- JFPZXAXJJFRETR-UHFFFAOYSA-N CCCOOOB(O)OOOCCC Chemical compound CCCOOOB(O)OOOCCC JFPZXAXJJFRETR-UHFFFAOYSA-N 0.000 claims description 10
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims 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 claims description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 7
- 239000004327 boric acid Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 7
- -1 1-cyclopropyl Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 238000001237 Raman spectrum Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 238000001757 thermogravimetry curve Methods 0.000 claims description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 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
- 208000035473 Communicable disease Diseases 0.000 claims 2
- MEGKGWWDESTXJL-UHFFFAOYSA-N 3-oxo-2,4-dihydro-1h-quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C(=O)CNC2=C1 MEGKGWWDESTXJL-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 13
- 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000008213 purified water Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 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 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 0 CCC(C(C1[U]C)=CN(C2CC2)c(c(*)c2F)c1cc2I)=N Chemical compound CCC(C(C1[U]C)=CN(C2CC2)c(c(*)c2F)c1cc2I)=N 0.000 description 2
- 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
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 241000606768 Haemophilus influenzae Species 0.000 description 2
- 241000606766 Haemophilus parainfluenzae Species 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
- 238000001069 Raman spectroscopy Methods 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
- 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
- 239000013078 crystal Substances 0.000 description 2
- 229940047650 haemophilus influenzae Drugs 0.000 description 2
- 208000015181 infectious disease Diseases 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 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
- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- KSCPLKVBWDOSAI-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCCC2CNCC21 KSCPLKVBWDOSAI-UHFFFAOYSA-N 0.000 description 1
- SXEMUBYCBZZXCU-UHFFFAOYSA-N 3-oxo-2,4-dihydro-1h-quinoline-2-carboxylic acid Chemical compound C1=CC=C2CC(=O)C(C(=O)O)NC2=C1 SXEMUBYCBZZXCU-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
- YNFWAIPSUMXPNG-UHFFFAOYSA-N CCC(O[B](C(C1)CC1C1=O)(OC(CC)=O)[O]=C(c2cc(F)c3F)C1=CN(C1CC1)c2c3OC)=O Chemical compound CCC(O[B](C(C1)CC1C1=O)(OC(CC)=O)[O]=C(c2cc(F)c3F)C1=CN(C1CC1)c2c3OC)=O YNFWAIPSUMXPNG-UHFFFAOYSA-N 0.000 description 1
- 102100034741 Cyclin-dependent kinase 20 Human genes 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 class CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 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 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002458 infectious 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
- 238000005259 measurement Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 229960004954 sparfloxacin Drugs 0.000 description 1
- DZZWHBIBMUVIIW-DTORHVGOSA-N sparfloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DZZWHBIBMUVIIW-DTORHVGOSA-N 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
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
i)無水プロピオン酸およびホウ酸をエチル-1-シクロプロピル-6-7-ジフルオロ-8-メトキシ-4-オキソ-1,4-ジヒドロ-3-キノロンカルボキシレート(A)と反応させて、1-シクロプロピル-6,7-ジフルオロ-8-メトキシ-4-オキソ-1,4-ジヒドロ-3-キノリンカルボン酸-O3,O4 ビス(プロピルオキシ-O)ボレート(I)を得ること;
ii)ボレート複合体(I)を、有機溶媒中で、塩基の非存在下において、ノナン(B)と縮合させて、新規中間体(4aS-シス)-(1-シクロプロピル-7-(2,8-ジアザビシクロ [4.3.0] ノン-8-イル)-6-フルオロ-8-メトキシ-4-オキソ-1,4-ジヒドロ-3-キノリンカルボン酸-O3,O4)ビス(プロピルオキシ-O) ボレート(II)を得ること;および
iii)中間体(II)を加水分解して、モキシフロキサシン塩基を得ること。
Claims (28)
i)無水プロピオン酸およびホウ酸をエチル-1-シクロプロピル-6-7-ジフルオロ-8-メトキシ-4-オキソ-1,4-ジヒドロ-3-キノロンカルボキシレートと反応させて、1-シクロプロピル-6,7-ジフルオロ-8-メトキシ-4-オキソ-1,4-ジヒドロ-3-キノリンカルボン酸-O3,O4 ビス(プロピルオキシ-O)ボレートを得る工程;
ii)このボレート複合体(I)を(S,S)-2,8-ジアザビシクロ [4.3.0] ノナンと有機溶媒中で縮合させて、中間体である(4aS-シス)-(1-シクロプロピル-7-(2,8-ジアザビシクロ [4.3.0] ノン-8-イル)-6-フルオロ-8-メトキシ-4-オキソ-1,4-ジヒドロ-3-キノリンカルボン酸-O3,O4)ビス(プロピルオキシ-O) ボレートを得る工程;
iii)この中間体(II)を加水分解して、モキシフロキサシン塩基を得る工程。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN1879MU2006 | 2006-11-13 | ||
PCT/GB2007/004320 WO2008059223A2 (en) | 2006-11-13 | 2007-11-13 | Process for the synthesis of moxifloxacin hydrochloride |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2014003579A Division JP5774732B2 (ja) | 2006-11-13 | 2014-01-10 | モキシフロキサシン塩酸塩の合成方法 |
Publications (1)
Publication Number | Publication Date |
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JP2010509305A true JP2010509305A (ja) | 2010-03-25 |
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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JP2009535810A Pending JP2010509305A (ja) | 2006-11-13 | 2007-11-13 | モキシフロキサシン塩酸塩の合成方法 |
JP2014003579A Expired - Fee Related JP5774732B2 (ja) | 2006-11-13 | 2014-01-10 | モキシフロキサシン塩酸塩の合成方法 |
Family Applications After (1)
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JP2014003579A Expired - Fee Related JP5774732B2 (ja) | 2006-11-13 | 2014-01-10 | モキシフロキサシン塩酸塩の合成方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US8198451B2 (ja) |
EP (2) | EP2089388B1 (ja) |
JP (2) | JP2010509305A (ja) |
KR (2) | KR20150048920A (ja) |
AU (1) | AU2007320997B2 (ja) |
CA (1) | CA2669427A1 (ja) |
IN (1) | IN2014MN02582A (ja) |
NZ (1) | NZ576929A (ja) |
WO (1) | WO2008059223A2 (ja) |
ZA (1) | ZA200903889B (ja) |
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 |
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- 2007-11-13 CA CA002669427A patent/CA2669427A1/en not_active Abandoned
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- 2007-11-13 WO PCT/GB2007/004320 patent/WO2008059223A2/en active Application Filing
- 2007-11-13 KR KR1020157010216A patent/KR20150048920A/ko not_active Application Discontinuation
- 2007-11-13 KR KR1020097012171A patent/KR101539561B1/ko not_active IP Right Cessation
- 2007-11-13 EP EP12159510A patent/EP2474547A3/en not_active Withdrawn
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Also Published As
Publication number | Publication date |
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KR101539561B1 (ko) | 2015-07-27 |
WO2008059223A3 (en) | 2008-07-31 |
JP2014122223A (ja) | 2014-07-03 |
US8198451B2 (en) | 2012-06-12 |
KR20150048920A (ko) | 2015-05-07 |
JP5774732B2 (ja) | 2015-09-09 |
IN2014MN02582A (ja) | 2015-09-11 |
EP2089388B1 (en) | 2014-01-29 |
KR20090090337A (ko) | 2009-08-25 |
NZ576929A (en) | 2012-07-27 |
AU2007320997B2 (en) | 2012-11-08 |
ZA200903889B (en) | 2010-03-31 |
EP2089388A2 (en) | 2009-08-19 |
CA2669427A1 (en) | 2008-05-22 |
EP2474547A3 (en) | 2012-07-25 |
EP2474547A2 (en) | 2012-07-11 |
US20100152229A1 (en) | 2010-06-17 |
AU2007320997A1 (en) | 2008-05-22 |
WO2008059223A2 (en) | 2008-05-22 |
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