JP4208464B2 - ナフチリジン−３−カルボン酸誘導体の製造法 - Google Patents
ナフチリジン−３−カルボン酸誘導体の製造法 Download PDFInfo
- Publication number
- JP4208464B2 JP4208464B2 JP2001522225A JP2001522225A JP4208464B2 JP 4208464 B2 JP4208464 B2 JP 4208464B2 JP 2001522225 A JP2001522225 A JP 2001522225A JP 2001522225 A JP2001522225 A JP 2001522225A JP 4208464 B2 JP4208464 B2 JP 4208464B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- naphthyridine
- carboxylic acid
- compound represented
- compound
- 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 - Fee Related
Links
- 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 description 8
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 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 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims 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 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical class [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 229940098779 methanesulfonic acid Drugs 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- -1 3-aminomethyl-4-methoxyiminopyrrolidin-1-yl Chemical group 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 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 description 4
- 239000000126 substance Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- WWPSDNRRMDKBHO-UHFFFAOYSA-N (4-methoxyiminopyrrolidin-3-yl)methanamine;dihydrochloride Chemical compound Cl.Cl.CON=C1CNCC1CN WWPSDNRRMDKBHO-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- KVERQKOZMUXLTL-UHFFFAOYSA-N methanesulfonic acid trihydrate Chemical compound O.O.O.CS(O)(=O)=O.CS(O)(=O)=O KVERQKOZMUXLTL-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- IWZIMRWBERTXPB-UHFFFAOYSA-N (4-methoxyiminopyrrolidin-1-ium-3-yl)methanamine 2,2,2-trifluoroacetate Chemical compound FC(C(=O)[O-])(F)F.FC(C(=O)[O-])(F)F.NCC1C(C[NH2+]C1)=NOC.NCC1C(C[NH2+]C1)=NOC IWZIMRWBERTXPB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LEDQBZYEIOHQMG-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.C12=NC=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 LEDQBZYEIOHQMG-UHFFFAOYSA-N 0.000 description 1
- OXNZWNNMJBOZQO-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C12=NC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 OXNZWNNMJBOZQO-UHFFFAOYSA-N 0.000 description 1
- 0 CC*N(C=C(*)C(c1c2)=O)c1nc(*)c2F Chemical compound CC*N(C=C(*)C(c1c2)=O)c1nc(*)c2F 0.000 description 1
- NKWQSQKRJTWNBT-UHFFFAOYSA-N CS([O-])(=O)=O.CS([O-])(=O)=O.CON=C1C[NH+](C)CC1N.CON=C1C[NH+](C)CC1N Chemical compound CS([O-])(=O)=O.CS([O-])(=O)=O.CON=C1C[NH+](C)CC1N.CON=C1C[NH+](C)CC1N NKWQSQKRJTWNBT-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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9920917.3A GB9920917D0 (en) | 1999-09-03 | 1999-09-03 | Novel process |
| GB9920917.3 | 1999-09-03 | ||
| PCT/GB2000/003366 WO2001018002A1 (en) | 1999-09-03 | 2000-09-01 | Process for production of naphthyridine-3-carboxylic acid derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003508532A JP2003508532A (ja) | 2003-03-04 |
| JP2003508532A5 JP2003508532A5 (enExample) | 2005-12-22 |
| JP4208464B2 true JP4208464B2 (ja) | 2009-01-14 |
Family
ID=10860353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001522225A Expired - Fee Related JP4208464B2 (ja) | 1999-09-03 | 2000-09-01 | ナフチリジン−３−カルボン酸誘導体の製造法 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7232907B2 (enExample) |
| EP (1) | EP1214321B1 (enExample) |
| JP (1) | JP4208464B2 (enExample) |
| KR (1) | KR100724311B1 (enExample) |
| CN (1) | CN1275963C (enExample) |
| AR (1) | AR029002A1 (enExample) |
| AT (1) | ATE271050T1 (enExample) |
| AU (1) | AU773722B2 (enExample) |
| BR (1) | BRPI0013751B8 (enExample) |
| CA (1) | CA2383753C (enExample) |
| CO (1) | CO5470281A1 (enExample) |
| DE (1) | DE60012196T2 (enExample) |
| DK (1) | DK1214321T3 (enExample) |
| ES (1) | ES2223574T3 (enExample) |
| GB (1) | GB9920917D0 (enExample) |
| HK (1) | HK1047093B (enExample) |
| MX (1) | MXPA02002355A (enExample) |
| MY (1) | MY125309A (enExample) |
| PT (1) | PT1214321E (enExample) |
| SI (1) | SI1214321T1 (enExample) |
| TW (1) | TWI274753B (enExample) |
| WO (1) | WO2001018002A1 (enExample) |
| ZA (1) | ZA200201781B (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 |
| WO2003011450A1 (en) | 2001-08-02 | 2003-02-13 | Lg Life Sciences Limited | Processes for the production of amino-protected derivatives of 4-aminomethylene-pyrrolidin-3-one and/or 4-aminomethylene-pyrrolidin-3-alkoxyimino derivatives and/or gemifloxacin or a salt thereof |
| KR100517638B1 (ko) * | 2002-04-08 | 2005-09-28 | 주식회사 엘지생명과학 | 게미플록사신 산염의 새로운 제조방법 |
| KR100653334B1 (ko) * | 2003-03-07 | 2006-12-04 | 주식회사 엘지생명과학 | 4-아미노메틸-3-알콕시이미노피롤리딘 메탄설폰산염의 신규한 제조 방법 |
| 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 |
| 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 (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 |
| IE66202B1 (en) | 1989-08-16 | 1995-12-13 | Pfizer | Azabicyclo quinolone carboxylic acids |
| 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 |
| DK0688772T3 (da) * | 1994-06-16 | 1999-11-01 | Lg Chemical Ltd | Quinolincarboxylsyrederivater med 7-(4-aminomethyl-3-oxim)-pyrrolidinsubstituenter og fremgangsmåde til deres fremstilling |
| 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 |
| 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 |
| RU2140910C1 (ru) | 1995-08-11 | 1999-11-10 | Пфайзер Инк. | Тригидрат метансульфоната (1s,2s)-1-(4-гидроксифенил)-2-(4-гидрокси-4- фенилпиперидин-1-ил)-1-пропанола |
| BR9708336A (pt) | 1996-03-29 | 1999-08-03 | Smithkline Beecham Corp | Diidrato de eprosartan e processo para sua produção e formulação |
| 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 |
| JP2002516308A (ja) | 1998-05-29 | 2002-06-04 | ファルマシア・アンド・アップジョン・カンパニー | ３−［（１’−ｎ−メチルアミノ）エチル−ｎ−ベンジル］ピロリジンモノメタンスルホネート |
| 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 |
| 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 |
-
1999
- 1999-09-03 GB GBGB9920917.3A patent/GB9920917D0/en not_active Ceased
-
2000
- 2000-09-01 EP EP00958776A patent/EP1214321B1/en not_active Expired - Lifetime
- 2000-09-01 CO CO00065924A patent/CO5470281A1/es active IP Right Grant
- 2000-09-01 AU AU70197/00A patent/AU773722B2/en not_active Ceased
- 2000-09-01 ES ES00958776T patent/ES2223574T3/es not_active Expired - Lifetime
- 2000-09-01 DK DK00958776T patent/DK1214321T3/da active
- 2000-09-01 CA CA2383753A patent/CA2383753C/en not_active Expired - Lifetime
- 2000-09-01 KR KR1020027002869A patent/KR100724311B1/ko not_active Expired - Lifetime
- 2000-09-01 DE DE60012196T patent/DE60012196T2/de not_active Expired - Lifetime
- 2000-09-01 HK HK02108462.0A patent/HK1047093B/en not_active IP Right Cessation
- 2000-09-01 JP JP2001522225A patent/JP4208464B2/ja not_active Expired - Fee Related
- 2000-09-01 BR BRPI0013751A patent/BRPI0013751B8/pt not_active IP Right Cessation
- 2000-09-01 WO PCT/GB2000/003366 patent/WO2001018002A1/en not_active Ceased
- 2000-09-01 AR ARP000104595A patent/AR029002A1/es not_active Application Discontinuation
- 2000-09-01 CN CNB008123314A patent/CN1275963C/zh not_active Expired - Lifetime
- 2000-09-01 MX MXPA02002355A patent/MXPA02002355A/es active IP Right Grant
- 2000-09-01 MY MYPI20004054 patent/MY125309A/en unknown
- 2000-09-01 PT PT00958776T patent/PT1214321E/pt unknown
- 2000-09-01 SI SI200030482T patent/SI1214321T1/xx unknown
- 2000-09-01 AT AT00958776T patent/ATE271050T1/de active
- 2000-09-29 TW TW089120236A patent/TWI274753B/zh not_active IP Right Cessation
-
2002
- 2002-03-04 ZA ZA200201781A patent/ZA200201781B/xx unknown
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2003
- 2003-10-24 US US10/692,640 patent/US7232907B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA02002355A (es) | 2004-07-16 |
| GB9920917D0 (en) | 1999-11-10 |
| CA2383753A1 (en) | 2001-03-15 |
| KR100724311B1 (ko) | 2007-06-04 |
| TWI274753B (en) | 2007-03-01 |
| DK1214321T3 (da) | 2004-10-25 |
| CN1377350A (zh) | 2002-10-30 |
| ATE271050T1 (de) | 2004-07-15 |
| AU773722B2 (en) | 2004-06-03 |
| EP1214321A1 (en) | 2002-06-19 |
| CA2383753C (en) | 2011-06-28 |
| PT1214321E (pt) | 2004-10-29 |
| ES2223574T3 (es) | 2005-03-01 |
| EP1214321B1 (en) | 2004-07-14 |
| HK1047093A1 (en) | 2003-02-07 |
| JP2003508532A (ja) | 2003-03-04 |
| DE60012196T2 (de) | 2005-08-18 |
| ZA200201781B (en) | 2003-06-25 |
| BR0013751A (pt) | 2002-05-07 |
| KR20020041421A (ko) | 2002-06-01 |
| SI1214321T1 (en) | 2004-12-31 |
| US7232907B2 (en) | 2007-06-19 |
| US20050176961A1 (en) | 2005-08-11 |
| HK1047093B (en) | 2005-05-27 |
| BR0013751B1 (pt) | 2013-02-05 |
| CO5470281A1 (es) | 2004-12-30 |
| AU7019700A (en) | 2001-04-10 |
| WO2001018002A1 (en) | 2001-03-15 |
| DE60012196D1 (de) | 2004-08-19 |
| BRPI0013751B8 (pt) | 2021-05-25 |
| AR029002A1 (es) | 2003-06-04 |
| MY125309A (en) | 2006-07-31 |
| CN1275963C (zh) | 2006-09-20 |
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