CN1248580A - 制备托诺氟沙星酸式盐的方法 - Google Patents
制备托诺氟沙星酸式盐的方法 Download PDFInfo
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- CN1248580A CN1248580A CN99118470A CN99118470A CN1248580A CN 1248580 A CN1248580 A CN 1248580A CN 99118470 A CN99118470 A CN 99118470A CN 99118470 A CN99118470 A CN 99118470A CN 1248580 A CN1248580 A CN 1248580A
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- Prior art keywords
- acid
- compound
- formula
- alkyl
- tonorfloxacin
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- 150000003839 salts Chemical class 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000002253 acid Substances 0.000 claims abstract description 35
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 31
- 239000011707 mineral Substances 0.000 claims abstract description 31
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 22
- -1 but not limited to Substances 0.000 claims abstract description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 10
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims abstract description 5
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- 125000004494 ethyl ester group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 9
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
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- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 claims description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 claims description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 3
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 claims description 3
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 3
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 3
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 229940092714 benzenesulfonic acid Drugs 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
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- 239000011975 tartaric acid Substances 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
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- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 21
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- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960000497 trovafloxacin Drugs 0.000 description 1
Classifications
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cephalosporin Compounds (AREA)
- Indole Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9894498P | 1998-09-03 | 1998-09-03 | |
| US60/098,944 | 1998-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1248580A true CN1248580A (zh) | 2000-03-29 |
Family
ID=22271674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99118470A Pending CN1248580A (zh) | 1998-09-03 | 1999-09-02 | 制备托诺氟沙星酸式盐的方法 |
Country Status (40)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104892507A (zh) * | 2015-05-26 | 2015-09-09 | 徐州天意动物药业有限公司 | 水溶性甲磺酸沙拉沙星及其制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164402A (en) * | 1989-08-16 | 1992-11-17 | Pfizer Inc | Azabicyclo quinolone and naphthyridinone carboxylic acids |
| BR9408490A (pt) * | 1994-01-18 | 1997-08-26 | Pfizer | Processo e intermediários para a preparação de sais do ácido nafftiridonocarboxílico |
| CA2223404C (en) * | 1995-06-06 | 2001-01-16 | Thomas A. Morris | Novel crystal form of anhydrous 7-(¬1.alpha., 5.alpha., 6.alpha.|-6-amino-3-azabicyclo¬3.1.0|hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, methanesulfonic acid salt |
| JPH0912547A (ja) * | 1995-06-23 | 1997-01-14 | Chisso Corp | ニューキノロン系化合物中間体の製造方法 |
| JPH0912546A (ja) * | 1995-06-23 | 1997-01-14 | Chisso Corp | アザビシクロ環化合物および製造方法 |
| TR199800339T1 (xx) * | 1995-08-29 | 1998-06-22 | Pfizer Inc. | Trovafloksasinin melez iyonik bi�imleri. |
| US6184380B1 (en) * | 1999-01-25 | 2001-02-06 | Pfizer Inc. | Process for preparing naphthyridones and intermediates |
| PA8464701A1 (es) * | 1998-01-16 | 2000-09-29 | Pfizer Prod Inc | Procedimiento e intermedios para preparar naftiridonas |
-
1999
- 1999-08-17 HN HN1999000141A patent/HN1999000141A/es unknown
- 1999-08-25 GT GT199900142A patent/GT199900142A/es unknown
- 1999-08-25 SK SK1165-99A patent/SK116599A3/sk unknown
- 1999-08-26 IL IL13161499A patent/IL131614A0/xx unknown
- 1999-08-26 US US09/383,320 patent/US6359137B1/en not_active Expired - Fee Related
- 1999-08-27 AU AU44826/99A patent/AU761035B2/en not_active Ceased
- 1999-08-30 TW TW088114861A patent/TW520369B/zh active
- 1999-08-30 IS IS5168A patent/IS5168A/is unknown
- 1999-08-31 UY UY25686A patent/UY25686A1/es not_active Application Discontinuation
- 1999-08-31 PA PA19998481001A patent/PA8481001A1/es unknown
- 1999-08-31 OA OA9900199A patent/OA11152A/en unknown
- 1999-09-01 ZA ZA9905630A patent/ZA995630B/xx unknown
- 1999-09-01 PE PE1999000878A patent/PE20001026A1/es not_active Application Discontinuation
- 1999-09-01 MY MYPI99003775A patent/MY130800A/en unknown
- 1999-09-01 TN TNTNSN99164A patent/TNSN99164A1/fr unknown
- 1999-09-01 SG SG1999004240A patent/SG74748A1/en unknown
- 1999-09-01 CA CA002281244A patent/CA2281244C/en not_active Expired - Fee Related
- 1999-09-01 JP JP24737399A patent/JP3354526B2/ja not_active Expired - Fee Related
- 1999-09-01 MA MA25749A patent/MA24966A1/fr unknown
- 1999-09-01 IN IN1171DE1999 patent/IN191583B/en unknown
- 1999-09-01 BG BG103703A patent/BG103703A/bg unknown
- 1999-09-01 EP EP99306947A patent/EP0989119A1/en not_active Withdrawn
- 1999-09-01 EA EA199900708A patent/EA002340B1/ru not_active IP Right Cessation
- 1999-09-02 KR KR1019990037060A patent/KR20000022858A/ko not_active Abandoned
- 1999-09-02 EE EEP199900457A patent/EE04118B1/xx not_active IP Right Cessation
- 1999-09-02 NZ NZ337605A patent/NZ337605A/xx unknown
- 1999-09-02 AR ARP990104424A patent/AR021475A1/es unknown
- 1999-09-02 NO NO994261A patent/NO994261L/no unknown
- 1999-09-02 HU HU9902967A patent/HUP9902967A3/hu unknown
- 1999-09-02 SV SV1999000144A patent/SV1999000144A/es not_active Application Discontinuation
- 1999-09-02 YU YU43199A patent/YU43199A/sh unknown
- 1999-09-02 ID IDP990831D patent/ID23718A/id unknown
- 1999-09-02 AP APAP/P/1999/001667A patent/AP1118A/en active
- 1999-09-02 CN CN99118470A patent/CN1248580A/zh active Pending
- 1999-09-02 TR TR1999/02138A patent/TR199902138A2/xx unknown
- 1999-09-03 GE GEAP19994978A patent/GEP20022785B/en unknown
- 1999-09-03 BR BR9904082-4A patent/BR9904082A/pt not_active Application Discontinuation
- 1999-09-03 PL PL99335246A patent/PL335246A1/xx not_active Application Discontinuation
- 1999-09-03 CO CO99055924A patent/CO5251466A1/es not_active Application Discontinuation
- 1999-09-03 HR HR990274A patent/HRP990274A2/hr not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104892507A (zh) * | 2015-05-26 | 2015-09-09 | 徐州天意动物药业有限公司 | 水溶性甲磺酸沙拉沙星及其制备方法 |
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