KR100705363B1 - 나프티리딘-3-카르복실산 유도체의 제조를 위한 중간체 - Google Patents
나프티리딘-3-카르복실산 유도체의 제조를 위한 중간체 Download PDFInfo
- Publication number
- KR100705363B1 KR100705363B1 KR1020027002876A KR20027002876A KR100705363B1 KR 100705363 B1 KR100705363 B1 KR 100705363B1 KR 1020027002876 A KR1020027002876 A KR 1020027002876A KR 20027002876 A KR20027002876 A KR 20027002876A KR 100705363 B1 KR100705363 B1 KR 100705363B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- aminomethyl
- reaction
- carried out
- 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.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000000543 intermediate Substances 0.000 title description 4
- CGXLVFZJJOXEDF-UHFFFAOYSA-N 1,8-naphthyridine-3-carboxylic acid Chemical class N1=CC=CC2=CC(C(=O)O)=CN=C21 CGXLVFZJJOXEDF-UHFFFAOYSA-N 0.000 title 1
- UEOGQXKQVBYIDZ-UHFFFAOYSA-N methanesulfonate;(4-methoxyiminopyrrolidin-1-ium-3-yl)methanamine Chemical compound CS([O-])(=O)=O.CS([O-])(=O)=O.CON=C1C[NH2+]CC1CN.CON=C1C[NH2+]CC1CN UEOGQXKQVBYIDZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 42
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- -1 t-butyloxycarbonyl Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 abstract description 3
- SNLMOXFUCILIPL-UHFFFAOYSA-N 1,8-naphthyridine-2-carboxylic acid Chemical class C1=CC=NC2=NC(C(=O)O)=CC=C21 SNLMOXFUCILIPL-UHFFFAOYSA-N 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 0 C*(C)C[C@](CN)C(*)=NOC Chemical compound C*(C)C[C@](CN)C(*)=NOC 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- ZEEYWNLTALRSIE-UHFFFAOYSA-N 1-(aminomethyl)pyrrolidin-3-one Chemical compound NCN1CCC(=O)C1 ZEEYWNLTALRSIE-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
- SCANHWGNLLBPRH-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-1,8-naphthyridin-4-one Chemical compound N1=C(Cl)C(F)=CC(C(C=C2)=O)=C1N2C1CC1 SCANHWGNLLBPRH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UQEJWZPQHPZHAZ-UHFFFAOYSA-N O.CS(=O)(=O)O.O=C1C(=CNC2=NC=CC=C12)C(=O)O.O.O.O=C1C(=CNC2=NC=CC=C12)C(=O)O.CS(=O)(=O)O Chemical compound O.CS(=O)(=O)O.O=C1C(=CNC2=NC=CC=C12)C(=O)O.O.O.O=C1C(=CNC2=NC=CC=C12)C(=O)O.CS(=O)(=O)O UQEJWZPQHPZHAZ-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9920919.9A GB9920919D0 (en) | 1999-09-03 | 1999-09-03 | Novel compound |
| GB9920919.9 | 1999-09-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20020041423A KR20020041423A (ko) | 2002-06-01 |
| KR100705363B1 true KR100705363B1 (ko) | 2007-04-10 |
Family
ID=10860355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027002876A Expired - Lifetime KR100705363B1 (ko) | 1999-09-03 | 2000-09-01 | 나프티리딘-3-카르복실산 유도체의 제조를 위한 중간체 |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US6703512B1 (enExample) |
| EP (1) | EP1212321B1 (enExample) |
| JP (1) | JP4208463B2 (enExample) |
| KR (1) | KR100705363B1 (enExample) |
| CN (1) | CN1255402C (enExample) |
| AR (1) | AR029452A1 (enExample) |
| AT (1) | ATE270671T1 (enExample) |
| AU (1) | AU773698B2 (enExample) |
| BR (1) | BRPI0013750B8 (enExample) |
| CA (1) | CA2383751C (enExample) |
| CO (1) | CO5180620A1 (enExample) |
| CZ (1) | CZ2002759A3 (enExample) |
| DE (1) | DE60012028T2 (enExample) |
| DK (1) | DK1212321T3 (enExample) |
| ES (1) | ES2223570T3 (enExample) |
| GB (1) | GB9920919D0 (enExample) |
| HK (1) | HK1046908B (enExample) |
| HU (1) | HU229391B1 (enExample) |
| IL (2) | IL148441A0 (enExample) |
| MX (1) | MXPA02002356A (enExample) |
| MY (1) | MY126789A (enExample) |
| NO (1) | NO322501B1 (enExample) |
| NZ (1) | NZ517601A (enExample) |
| PL (1) | PL206491B1 (enExample) |
| PT (1) | PT1212321E (enExample) |
| SI (1) | SI1212321T1 (enExample) |
| TR (1) | TR200200548T2 (enExample) |
| TW (1) | TWI264435B (enExample) |
| WO (1) | WO2001017961A2 (enExample) |
| ZA (1) | ZA200201779B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2281817C (en) * | 1999-06-29 | 2008-07-29 | Smithkline Beecham Corporation | Methods of use of fluoroquinolone compounds against maxillary sinus pathogenic 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 |
| PT1412078E (pt) | 2001-08-02 | 2009-01-08 | Lg Life Sciences Ltd | Processos para a produção de derivados amino-protegidos da 4- aminometileno-pirrolidin-3-ona, gemifloxacina ou um seu sal |
| KR100517638B1 (ko) | 2002-04-08 | 2005-09-28 | 주식회사 엘지생명과학 | 게미플록사신 산염의 새로운 제조방법 |
| KR101061456B1 (ko) * | 2002-07-17 | 2011-09-02 | 시바 홀딩 인크 | 퀴나크리돈 안료를 제조하기 위한 산화방법 |
| KR100653334B1 (ko) * | 2003-03-07 | 2006-12-04 | 주식회사 엘지생명과학 | 4-아미노메틸-3-알콕시이미노피롤리딘 메탄설폰산염의 신규한 제조 방법 |
| US8822934B2 (en) * | 2006-11-03 | 2014-09-02 | Accuray Incorporated | Collimator changer |
| CN104693088B (zh) * | 2013-12-06 | 2018-01-05 | 常州市勇毅生物药业有限公司 | 一种吉米沙星侧链的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0688772A1 (en) * | 1994-06-16 | 1995-12-27 | LG Chemical Limited | Novel quinoline carboxylic acid derivatives having 7-(4-amino-methyl-3-oxime) pyrrolidine substituents and processes for their preparation |
| WO1998042705A1 (en) * | 1997-03-21 | 1998-10-01 | Lg Chemical Ltd. | Salt of naphthyridine carboxylic acid derivative |
Family Cites Families (25)
| 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 (enExample) | 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 |
| 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 |
| ES2117426T3 (es) | 1995-06-06 | 1998-08-01 | Pfizer | Forma cristalina de la sal anhidra compuesta de los acidos 7-((1a,5a,6a)-6-amino-3-azabiciclo(3.1.0.)hex-3-il)-6-fluoro-1-(2,4-difluorofenil)-1,4-dihidro-4-oxo-1,8-naftiridina-3-carboxilico y metanosulfonico. |
| UA59341C2 (uk) | 1995-08-11 | 2003-09-15 | Пфайзер, Інк. | (1s,2s)-1-(4-гідроксифеніл)-2-(4-гідрокси-4-фенілпіперидин-1-іл)-1-пропанолметансульфонат тригідрат |
| JP4316013B2 (ja) | 1996-03-29 | 2009-08-19 | スミスクライン・ビーチャム・コーポレイション | エプロサルタン二水和物ならびにその製法および処方 |
| KR100286874B1 (ko) | 1998-03-04 | 2001-04-16 | 성재갑 | 보호된 4-아미노메틸-피롤리딘-3-온의 제조방법 |
| PT1082300E (pt) | 1998-05-29 | 2004-02-27 | Upjohn Co | Monometanossulfonato de 3-¬(1'-n-metilamino)etil-n-benzil|pirrolidina |
| 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 |
| AU6947900A (en) | 1999-09-01 | 2001-03-26 | Smithkline Beecham Corporation | Methods of use of fluoroquinolone compounds against bacteria |
| GB9920917D0 (en) * | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel process |
| GB9920919D0 (en) * | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel compound |
| EP1242079A4 (en) | 1999-09-22 | 2003-01-22 | Smithkline Beecham | Methods of anti-bacterial use of fluoroquinolonic compounds |
| 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 |
-
1999
- 1999-09-03 GB GBGB9920919.9A patent/GB9920919D0/en not_active Ceased
-
2000
- 2000-09-01 SI SI200030481T patent/SI1212321T1/xx unknown
- 2000-09-01 US US10/088,149 patent/US6703512B1/en not_active Expired - Lifetime
- 2000-09-01 MY MYPI20004053 patent/MY126789A/en unknown
- 2000-09-01 TR TR2002/00548T patent/TR200200548T2/xx unknown
- 2000-09-01 PL PL354725A patent/PL206491B1/pl not_active IP Right Cessation
- 2000-09-01 EP EP00956706A patent/EP1212321B1/en not_active Expired - Lifetime
- 2000-09-01 HK HK02108460.2A patent/HK1046908B/en not_active IP Right Cessation
- 2000-09-01 DK DK00956706T patent/DK1212321T3/da active
- 2000-09-01 HU HU0202733A patent/HU229391B1/hu not_active IP Right Cessation
- 2000-09-01 PT PT00956706T patent/PT1212321E/pt unknown
- 2000-09-01 CA CA2383751A patent/CA2383751C/en not_active Expired - Lifetime
- 2000-09-01 JP JP2001521708A patent/JP4208463B2/ja not_active Expired - Fee Related
- 2000-09-01 AU AU68573/00A patent/AU773698B2/en not_active Ceased
- 2000-09-01 CN CNB008123292A patent/CN1255402C/zh not_active Expired - Lifetime
- 2000-09-01 BR BRPI0013750A patent/BRPI0013750B8/pt not_active IP Right Cessation
- 2000-09-01 MX MXPA02002356A patent/MXPA02002356A/es active IP Right Grant
- 2000-09-01 AT AT00956706T patent/ATE270671T1/de active
- 2000-09-01 CO CO00065923A patent/CO5180620A1/es active IP Right Grant
- 2000-09-01 KR KR1020027002876A patent/KR100705363B1/ko not_active Expired - Lifetime
- 2000-09-01 AR ARP000104596A patent/AR029452A1/es active IP Right Grant
- 2000-09-01 DE DE60012028T patent/DE60012028T2/de not_active Expired - Lifetime
- 2000-09-01 IL IL14844100A patent/IL148441A0/xx active IP Right Grant
- 2000-09-01 NZ NZ517601A patent/NZ517601A/en not_active IP Right Cessation
- 2000-09-01 CZ CZ2002759A patent/CZ2002759A3/cs unknown
- 2000-09-01 ES ES00956706T patent/ES2223570T3/es not_active Expired - Lifetime
- 2000-09-01 WO PCT/GB2000/003358 patent/WO2001017961A2/en not_active Ceased
- 2000-09-29 TW TW089120154A patent/TWI264435B/zh not_active IP Right Cessation
-
2002
- 2002-02-28 IL IL148441A patent/IL148441A/en unknown
- 2002-03-01 NO NO20021043A patent/NO322501B1/no not_active IP Right Cessation
- 2002-03-04 ZA ZA200201779A patent/ZA200201779B/xx unknown
-
2003
- 2003-12-23 US US10/742,797 patent/US6803467B2/en not_active Expired - Lifetime
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2004
- 2004-09-08 US US10/935,357 patent/US20050033064A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0688772A1 (en) * | 1994-06-16 | 1995-12-27 | LG Chemical Limited | Novel quinoline carboxylic acid derivatives having 7-(4-amino-methyl-3-oxime) pyrrolidine substituents and processes for their preparation |
| WO1998042705A1 (en) * | 1997-03-21 | 1998-10-01 | Lg Chemical Ltd. | Salt of naphthyridine carboxylic acid derivative |
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