OA12801A - Process for preparing acid salts of gemifloxacin. - Google Patents
Process for preparing acid salts of gemifloxacin. Download PDFInfo
- Publication number
- OA12801A OA12801A OA1200400271A OA1200400271A OA12801A OA 12801 A OA12801 A OA 12801A OA 1200400271 A OA1200400271 A OA 1200400271A OA 1200400271 A OA1200400271 A OA 1200400271A OA 12801 A OA12801 A OA 12801A
- Authority
- OA
- OAPI
- Prior art keywords
- acid
- formula
- compound
- reaction
- température
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 31
- ZRCVYEYHRGVLOC-HYARGMPZSA-N gemifloxacin Chemical class C1C(CN)C(=N/OC)/CN1C(C(=C1)F)=NC2=C1C(=O)C(C(O)=O)=CN2C1CC1 ZRCVYEYHRGVLOC-HYARGMPZSA-N 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 229960003170 gemifloxacin Drugs 0.000 title claims abstract description 10
- 150000003839 salts Chemical class 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 11
- 239000012046 mixed solvent Substances 0.000 claims description 10
- 238000005755 formation reaction Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 5
- YZBFISOEIGOFAF-UHFFFAOYSA-N (4-methoxyiminopyrrolidin-3-yl)methanamine Chemical compound CON=C1CNCC1CN YZBFISOEIGOFAF-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- SNLMOXFUCILIPL-UHFFFAOYSA-N 1,8-naphthyridine-2-carboxylic acid Chemical compound C1=CC=NC2=NC(C(=O)O)=CC=C21 SNLMOXFUCILIPL-UHFFFAOYSA-N 0.000 claims description 2
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 claims 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 abstract description 3
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- -1 and éthanol Substances 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000001976 improved effect Effects 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- 229940044613 1-propanol Drugs 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007086 side reaction Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2002-0018847A KR100517638B1 (ko) | 2002-04-08 | 2002-04-08 | 게미플록사신 산염의 새로운 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA12801A true OA12801A (en) | 2006-07-11 |
Family
ID=36241771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200400271A OA12801A (en) | 2002-04-08 | 2003-04-04 | Process for preparing acid salts of gemifloxacin. |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US7361762B2 (is) |
| EP (1) | EP1497290B1 (is) |
| JP (1) | JP4315815B2 (is) |
| KR (1) | KR100517638B1 (is) |
| CN (1) | CN1291987C (is) |
| AP (1) | AP1786A (is) |
| AT (1) | ATE404559T1 (is) |
| AU (1) | AU2003219581B2 (is) |
| BR (1) | BRPI0309037B8 (is) |
| CA (1) | CA2481217C (is) |
| CO (1) | CO5611198A2 (is) |
| CY (1) | CY1108469T1 (is) |
| DE (1) | DE60322872D1 (is) |
| DK (1) | DK1497290T3 (is) |
| EA (1) | EA007222B1 (is) |
| ES (1) | ES2311694T3 (is) |
| GE (1) | GEP20074025B (is) |
| HR (1) | HRP20040929B1 (is) |
| IL (1) | IL164328A (is) |
| IS (1) | IS2731B (is) |
| MA (1) | MA26408A1 (is) |
| MX (1) | MXPA04009777A (is) |
| NO (1) | NO330042B1 (is) |
| NZ (1) | NZ536174A (is) |
| OA (1) | OA12801A (is) |
| PL (1) | PL372815A1 (is) |
| PT (1) | PT1497290E (is) |
| SI (1) | SI1497290T1 (is) |
| UA (1) | UA77070C2 (is) |
| WO (1) | WO2003087100A1 (is) |
| ZA (1) | ZA200408088B (is) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100892864B1 (ko) * | 2001-08-02 | 2009-04-15 | 주식회사 엘지생명과학 | 4-아미노메틸렌-피롤리딘-3-온의 아미노-보호 유도체및/또는 4-아미노메틸렌-피롤리딘-3-알콕시이미노유도체들 및/또는 제미플록사신 또는 그것의 염의 제조를위한 공정 |
| WO2006134431A1 (en) * | 2005-05-03 | 2006-12-21 | Ranbaxy Laboratories Limited | Formate salt of gemifloxacin |
| EP2159225A1 (en) * | 2005-06-15 | 2010-03-03 | Hetero Drugs Limited | Gemifloxacin process and polymorphs |
| JP5384119B2 (ja) * | 2006-03-07 | 2014-01-08 | ウォックハート リミテッド | ベンゾキノリジン−２−カルボン酸のプロドラッグ |
| US20100076193A1 (en) * | 2006-10-31 | 2010-03-25 | Chandrasekaran Ramasubbu | process for the preparation of gemifloxacin |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57134482A (en) | 1981-02-13 | 1982-08-19 | Dainippon Pharmaceut Co Ltd | 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation |
| IN162769B (is) | 1984-11-13 | 1988-07-09 | Kyorin Seiyaku Kk | |
| NZ222047A (en) | 1986-10-08 | 1991-01-29 | Bristol Myers Co | Quinoline - or naphthyridine - carboxylic acid anti-bacterial agents |
| JPH01100165A (ja) | 1987-10-13 | 1989-04-18 | Shionogi & Co Ltd | オキシムまたはヒドロキシアミン誘導体系抗菌剤 |
| US4920120A (en) | 1988-01-25 | 1990-04-24 | Warner-Lambert Company | Antibacterial agents |
| JPH0356479A (ja) | 1989-07-24 | 1991-03-12 | Takeshi Yokota | 水溶性キノロン誘導体のｐ‐トルエンスルホン酸塩 |
| PL166381B1 (pl) | 1989-08-16 | 1995-05-31 | Pfizer | Sposób wytwarzania nowych podstawionych kwasów 7-azabicyklochinolonokarboksylowych PL PL PL PL |
| US5137892A (en) | 1990-12-12 | 1992-08-11 | Abbott Laboratories | Quinoline, naphthyridine and pyridobenzoxazine derivatives |
| EP0541086A1 (en) | 1991-11-08 | 1993-05-12 | Kaken Pharmaceutical Co., Ltd. | Antibacterial 6-fluoro-quinolones having an oxime group on the substituent in position 7 |
| JPH0673056A (ja) | 1992-08-26 | 1994-03-15 | Kaken Pharmaceut Co Ltd | キノリンカルボン酸誘導体およびその塩 |
| US5776944A (en) * | 1994-06-16 | 1998-07-07 | Lg Chemical Ltd. | 7-(4-aminomethyl-3-methyloxyiminopyrroplidin-1-yl)-1-cyclopropyl-6-flu oro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and the process for the preparation thereof |
| DE69509442T2 (de) | 1994-06-16 | 1999-09-02 | Lg Chemical Ltd. | Chinolincarbonsäurederivate mit 7-(4-Amino-methyl-3-oxim)-pyrrolidin-Substituenten und Verfahren zu ihrer Herstellung |
| JP3449658B2 (ja) | 1994-12-21 | 2003-09-22 | 杏林製薬株式会社 | 安定性に優れた８−アルコキシキノロンカルボン酸水和物並びにその製造方法 |
| 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 |
| CZ296236B6 (cs) | 1995-08-11 | 2006-02-15 | Pfizer Inc. | Trihydrát methansulfonátu (1S,2S)-1-(4-hydroxyfenyl)-2-(4-hydroxy-4-fenylpiperidin-1-yl)-1-propanolu, farmaceutický prostredek a farmaceutická kombinace s jeho obsahem |
| UY24504A1 (es) | 1996-03-29 | 1997-09-19 | Smithkline Beecham Corp | Dihidrato de eprosartano y un procedimiento para su produccion y formulacion |
| MA24500A1 (fr) * | 1997-03-21 | 1998-10-01 | Lg Life Sciences Ltd | Derive du sel d'acide carboxylique de naphthyridine . |
| KR100286874B1 (ko) * | 1998-03-04 | 2001-04-16 | 성재갑 | 보호된 4-아미노메틸-피롤리딘-3-온의 제조방법 |
| DK1082300T3 (da) | 1998-05-29 | 2003-12-15 | Upjohn Co | 3-[1'-N-Methylamino)ethyl-N-benzyl]pyrrolidin-monomethansulfonat |
| GB9820405D0 (en) | 1998-09-18 | 1998-11-11 | Smithkline Beecham Plc | Process |
| PT1223935E (pt) | 1999-06-29 | 2008-04-03 | Lg Life Sciences Ltd | Utilização de compostos de gemifloxacina contra bactérias |
| EP1401440A4 (en) | 1999-09-01 | 2006-07-05 | Lg Life Sciences Ltd | METHODS OF USING FLUOROQUINOLONE COMPOUNDS AGAINST BACTERIA |
| GB9920919D0 (en) | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel compound |
| GB9920917D0 (en) * | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel process |
| AU7709400A (en) | 1999-09-22 | 2001-04-24 | Smithkline Beecham Corporation | Methods of use of fluoroquinolone compounds against bacteria |
| KR20010091379A (ko) | 2000-03-15 | 2001-10-23 | 성재갑 | 7-(4-아미노메틸-3-옥심)피롤리딘 치환체를 갖는 퀴놀린카르복실산 유도체의 신규 제조방법 |
| KR20020018560A (ko) | 2000-09-01 | 2002-03-08 | 성재갑 | 3-아미노메틸-4-ｚ-메톡시이미노피롤리딘의 신규 제조방법 |
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2002
- 2002-04-08 KR KR10-2002-0018847A patent/KR100517638B1/ko not_active Expired - Lifetime
-
2003
- 2003-04-04 HR HRP20040929AA patent/HRP20040929B1/hr not_active IP Right Cessation
- 2003-04-04 NZ NZ536174A patent/NZ536174A/en not_active IP Right Cessation
- 2003-04-04 AT AT03715805T patent/ATE404559T1/de active
- 2003-04-04 JP JP2003584056A patent/JP4315815B2/ja not_active Expired - Fee Related
- 2003-04-04 AU AU2003219581A patent/AU2003219581B2/en not_active Ceased
- 2003-04-04 BR BRPI0309037A patent/BRPI0309037B8/pt not_active IP Right Cessation
- 2003-04-04 AP APAP/P/2004/003148A patent/AP1786A/en active
- 2003-04-04 SI SI200331341T patent/SI1497290T1/sl unknown
- 2003-04-04 WO PCT/KR2003/000683 patent/WO2003087100A1/en not_active Ceased
- 2003-04-04 GE GEAP8436A patent/GEP20074025B/en unknown
- 2003-04-04 ES ES03715805T patent/ES2311694T3/es not_active Expired - Lifetime
- 2003-04-04 EP EP03715805A patent/EP1497290B1/en not_active Expired - Lifetime
- 2003-04-04 CN CNB038095483A patent/CN1291987C/zh not_active Expired - Lifetime
- 2003-04-04 MX MXPA04009777A patent/MXPA04009777A/es active IP Right Grant
- 2003-04-04 UA UA20041008144A patent/UA77070C2/uk unknown
- 2003-04-04 OA OA1200400271A patent/OA12801A/en unknown
- 2003-04-04 US US10/510,514 patent/US7361762B2/en not_active Expired - Lifetime
- 2003-04-04 CA CA2481217A patent/CA2481217C/en not_active Expired - Lifetime
- 2003-04-04 PL PL03372815A patent/PL372815A1/xx not_active Application Discontinuation
- 2003-04-04 EA EA200401328A patent/EA007222B1/ru not_active IP Right Cessation
- 2003-04-04 DK DK03715805T patent/DK1497290T3/da active
- 2003-04-04 DE DE60322872T patent/DE60322872D1/de not_active Expired - Lifetime
- 2003-04-04 PT PT03715805T patent/PT1497290E/pt unknown
-
2004
- 2004-09-30 IS IS7477A patent/IS2731B/is unknown
- 2004-10-05 CO CO04099283A patent/CO5611198A2/es active IP Right Grant
- 2004-10-07 MA MA27894A patent/MA26408A1/fr unknown
- 2004-10-07 ZA ZA200408088A patent/ZA200408088B/xx unknown
- 2004-10-21 IL IL164328A patent/IL164328A/en unknown
- 2004-10-27 NO NO20044629A patent/NO330042B1/no not_active IP Right Cessation
-
2008
- 2008-10-31 CY CY20081101234T patent/CY1108469T1/el unknown
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