PT96917B - Processo para a preparacao selectiva de cristais de hemi-hidrato ou mono-hidrato do acido (s)-9-fluoro-3-metil-1o-(4-metil-1-piperazinil)-7-oxo-3,4-di-hidro-7h-pirido{1,2,3-de} {1,4}benzoxazina-6-carboxilico - Google Patents
Processo para a preparacao selectiva de cristais de hemi-hidrato ou mono-hidrato do acido (s)-9-fluoro-3-metil-1o-(4-metil-1-piperazinil)-7-oxo-3,4-di-hidro-7h-pirido{1,2,3-de} {1,4}benzoxazina-6-carboxilico Download PDFInfo
- Publication number
- PT96917B PT96917B PT96917A PT9691791A PT96917B PT 96917 B PT96917 B PT 96917B PT 96917 A PT96917 A PT 96917A PT 9691791 A PT9691791 A PT 9691791A PT 96917 B PT96917 B PT 96917B
- Authority
- PT
- Portugal
- Prior art keywords
- methyl
- solvent
- process according
- water content
- pyrido
- Prior art date
Links
- 239000013078 crystal Substances 0.000 title claims description 53
- -1 4-METHYL-1-PIPERAZINYL Chemical class 0.000 title claims description 22
- CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical compound O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 title claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 47
- 150000004682 monohydrates Chemical class 0.000 claims abstract description 38
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims abstract description 36
- 230000008569 process Effects 0.000 claims abstract description 36
- 239000003125 aqueous solvent Substances 0.000 claims abstract description 23
- 238000002425 crystallisation Methods 0.000 claims abstract description 22
- 230000008025 crystallization Effects 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 36
- 229960003376 levofloxacin Drugs 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000001035 drying Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- 229940001981 carac Drugs 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 description 11
- 239000000725 suspension Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004455 differential thermal analysis Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000001159 Fisher's combined probability test Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005243 fluidization Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- QEHPHWRZQAZOTI-PPHPATTJSA-N levofloxacin monohydrate Chemical compound O.C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 QEHPHWRZQAZOTI-PPHPATTJSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5045490 | 1990-03-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT96917A PT96917A (pt) | 1991-10-31 |
| PT96917B true PT96917B (pt) | 1998-07-31 |
Family
ID=12859314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT96917A PT96917B (pt) | 1990-03-01 | 1991-02-28 | Processo para a preparacao selectiva de cristais de hemi-hidrato ou mono-hidrato do acido (s)-9-fluoro-3-metil-1o-(4-metil-1-piperazinil)-7-oxo-3,4-di-hidro-7h-pirido{1,2,3-de} {1,4}benzoxazina-6-carboxilico |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5545737A (en, 2012) |
| EP (1) | EP0444678B1 (en, 2012) |
| KR (1) | KR970000045B1 (en, 2012) |
| AT (1) | ATE157666T1 (en, 2012) |
| DE (1) | DE69127485T2 (en, 2012) |
| ES (1) | ES2106739T3 (en, 2012) |
| GR (1) | GR3025276T3 (en, 2012) |
| IE (1) | IE910692A1 (en, 2012) |
| IN (1) | IN172207B (en, 2012) |
| PT (1) | PT96917B (en, 2012) |
| TW (1) | TW208013B (en, 2012) |
| YU (1) | YU48328B (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA946853B (en) * | 1993-09-10 | 1995-04-24 | Daiichi Seiyaku Co | Crystals of antimicrobial compound. |
| PE20011061A1 (es) | 2000-02-01 | 2001-11-20 | Procter & Gamble | Cristalizacion selectiva del acido 3-piridil-1-hidroxi-etiliden-1,1-bisfosfonico sodio como el hemipentahidrato o el monohidrato |
| US6562974B2 (en) | 2000-02-01 | 2003-05-13 | The Procter & Gamble Company | Process for making geminal bisphosphonates |
| EP1772457A3 (en) | 2001-10-03 | 2007-07-04 | Teva Pharmaceutical Industries Ltd. | Preparation of levofloxacin and forms thereof |
| US7425628B2 (en) | 2001-10-03 | 2008-09-16 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
| AU2002365416A1 (en) * | 2001-11-29 | 2003-06-10 | Teva Pharmaceutical Industries Ltd. | Methods for the purification of levofloxacin |
| US20060276463A1 (en) * | 2002-12-16 | 2006-12-07 | Sharma Tarun K | Pure levofloxacin hemihydrate and processes for preparation thereof |
| KR100704641B1 (ko) * | 2004-07-21 | 2007-04-06 | 주식회사유한양행 | 고순도의 레보플록사신 제조방법 |
| EP1797101A4 (en) * | 2004-09-17 | 2009-11-11 | Matrix Lab Ltd | IMPROVED PROCESS FOR THE PREPARATION OF LEVOFLOXACIN HEMIHYDRATE |
| US20070244318A1 (en) * | 2004-11-08 | 2007-10-18 | Rao Davuluri R | Process for the Preparation of Levofloxacin Hemihydrate |
| ES2255871B1 (es) * | 2004-12-31 | 2007-08-16 | Quimica Sintetica, S.A. | Procedimiento para la obtencion de levofloxacino exento de sales. |
| CN1321121C (zh) * | 2005-04-21 | 2007-06-13 | 浙江医药股份有限公司新昌制药厂 | 左氧氟沙星制备及后处理方法 |
| US7964723B2 (en) * | 2008-08-02 | 2011-06-21 | Apeloa-Kangyu | And practical process for exclusively producing (S)-9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido-[1,2,3,de][1,4]benzoxazine-6-carboxylic acid hemihydrate |
| CN101863904A (zh) * | 2010-07-08 | 2010-10-20 | 浙江东亚药业有限公司 | 一种高纯度左氧氟沙星半水合物的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE203719C (en, 2012) * | 1907-11-02 | 1908-10-20 | ||
| JPS5746986A (en) * | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| JPS57131769A (en) * | 1981-02-10 | 1982-08-14 | Kissei Pharmaceut Co Ltd | 4-(1-imidazolylmethyl)cinnamic acid hydrochloride monohydrate, its preparation and drug containing the same |
| JPS5843977A (ja) * | 1981-09-09 | 1983-03-14 | Dai Ichi Seiyaku Co Ltd | ピリドベンズオキサジン誘導体の製法 |
| JPS60226855A (ja) * | 1984-04-26 | 1985-11-12 | Nippon Kayaku Co Ltd | Ｎ−ベンジルオキシカルボニル−ｌ−スレオニンアミド・１／２水和物およびその製造法 |
| NO166131C (no) * | 1985-06-20 | 1991-06-05 | Daiichi Seiyaku Co | Analogifremgangsmaate for fremstilling av s(-)-pyridobenzoksazinforbindelser. |
| ZA864518B (en) * | 1985-06-20 | 1987-03-25 | Daiichi Seiyaku Co | Optically active pyridobenzoxazine derivatives and intermediates thereof |
| MY104139A (en) * | 1988-08-09 | 1994-02-28 | Daiichi Seiyaku Co | Antimicrobial agent for animals |
| FI82240C (fi) * | 1988-10-20 | 1991-02-11 | Huhtamaeki Oy | Foerfarande foer framstaellning av farmakologiskt vaerdefullt s-timolol-hemihydrat. |
| MTP1076B (en) * | 1990-01-12 | 1991-09-30 | Ciba Geigy Ag | Hemihydrate |
-
1990
- 1990-03-13 TW TW080108336A patent/TW208013B/zh active
-
1991
- 1991-02-28 IN IN175/MAS/91A patent/IN172207B/en unknown
- 1991-02-28 PT PT96917A patent/PT96917B/pt not_active IP Right Cessation
- 1991-02-28 YU YU35491A patent/YU48328B/sh unknown
- 1991-02-28 ES ES91103032T patent/ES2106739T3/es not_active Expired - Lifetime
- 1991-02-28 AT AT91103032T patent/ATE157666T1/de not_active IP Right Cessation
- 1991-02-28 KR KR1019910003413A patent/KR970000045B1/ko not_active Expired - Lifetime
- 1991-02-28 EP EP91103032A patent/EP0444678B1/en not_active Expired - Lifetime
- 1991-02-28 DE DE69127485T patent/DE69127485T2/de not_active Expired - Lifetime
- 1991-03-01 IE IE069291A patent/IE910692A1/en not_active IP Right Cessation
-
1994
- 1994-01-18 US US08/182,364 patent/US5545737A/en not_active Expired - Lifetime
-
1997
- 1997-11-05 GR GR970402914T patent/GR3025276T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR970000045B1 (ko) | 1997-01-04 |
| IN172207B (en, 2012) | 1993-05-01 |
| KR910016748A (ko) | 1991-11-05 |
| DE69127485D1 (de) | 1997-10-09 |
| EP0444678B1 (en) | 1997-09-03 |
| GR3025276T3 (en) | 1998-02-27 |
| DE69127485T2 (de) | 1998-04-02 |
| HK1002730A1 (en) | 1998-09-11 |
| TW208013B (en, 2012) | 1993-06-21 |
| US5545737A (en) | 1996-08-13 |
| EP0444678A1 (en) | 1991-09-04 |
| YU35491A (sh) | 1994-04-05 |
| ATE157666T1 (de) | 1997-09-15 |
| ES2106739T3 (es) | 1997-11-16 |
| PT96917A (pt) | 1991-10-31 |
| IE910692A1 (en) | 1991-09-11 |
| YU48328B (sh) | 1998-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB1A | Laying open of patent application |
Effective date: 19910708 |
|
| FG3A | Patent granted, date of granting |
Effective date: 19980414 |
|
| PC4A | Transfer of assignment |
Owner name: DAIICHI SANKYO COMPANY, LIMITED, JP Effective date: 20071026 |
|
| MM4A | Annulment/lapse due to non-payment of fees, searched and examined patent |
Free format text: MAXIMUM VALIDITY LIMIT REACHED Effective date: 20130415 |