TWI274753B - Process for production of quinoline carboxylic acid derivatives - Google Patents
Process for production of quinoline carboxylic acid derivatives Download PDFInfo
- Publication number
- TWI274753B TWI274753B TW089120236A TW89120236A TWI274753B TW I274753 B TWI274753 B TW I274753B TW 089120236 A TW089120236 A TW 089120236A TW 89120236 A TW89120236 A TW 89120236A TW I274753 B TWI274753 B TW I274753B
- Authority
- TW
- Taiwan
- Prior art keywords
- formula
- compound
- hydrate
- doc
- solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000003125 aqueous solvent Substances 0.000 claims abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- -1 4-aminomercapto-3-methoxyiminopyrrolidinium disulfonate Chemical compound 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 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 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- RCBKDYCOSBVTGD-UHFFFAOYSA-N [N+](=O)([O-])C12CCCCCC2=CCCC1 Chemical compound [N+](=O)([O-])C12CCCCCC2=CCCC1 RCBKDYCOSBVTGD-UHFFFAOYSA-N 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000725 suspension 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 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
- 125000006242 amine protecting group Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- WWPSDNRRMDKBHO-UHFFFAOYSA-N (4-methoxyiminopyrrolidin-3-yl)methanamine;dihydrochloride Chemical compound Cl.Cl.CON=C1CNCC1CN WWPSDNRRMDKBHO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 208000001613 Gambling Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- HEABMVBRFLKRDB-UHFFFAOYSA-N acridine-3-carboxylic acid Chemical compound C1=CC=CC2=NC3=CC(C(=O)O)=CC=C3C=C21 HEABMVBRFLKRDB-UHFFFAOYSA-N 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001621 bismuth Chemical class 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000006824 pyrimidine synthesis Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011215 ultra-high-temperature ceramic Substances 0.000 description 1
- 238000001291 vacuum drying 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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9920917.3A GB9920917D0 (en) | 1999-09-03 | 1999-09-03 | Novel process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI274753B true TWI274753B (en) | 2007-03-01 |
Family
ID=10860353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089120236A TWI274753B (en) | 1999-09-03 | 2000-09-29 | Process for production of quinoline carboxylic acid derivatives |
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 |
| 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 |
| JP4208464B2 (ja) | 2009-01-14 |
| 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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