FI106460B - Bicykliska beta-laktam/parabenkomplexer och förfarande för framställning av beta-laktamderivat - Google Patents
Bicykliska beta-laktam/parabenkomplexer och förfarande för framställning av beta-laktamderivat Download PDFInfo
- Publication number
- FI106460B FI106460B FI943081A FI943081A FI106460B FI 106460 B FI106460 B FI 106460B FI 943081 A FI943081 A FI 943081A FI 943081 A FI943081 A FI 943081A FI 106460 B FI106460 B FI 106460B
- Authority
- FI
- Finland
- Prior art keywords
- loracarbef
- lactam
- paraben
- methylparaben
- hydrogen
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
- C07D463/16—Nitrogen atoms
- C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
- C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D463/22—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen further substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/59—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with hetero atoms directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (9)
1. Bicykliskt β-laktam/parabenkomplex med formeln : R,—^ ^~*3 "H2°
10 O * COOH (V) där X är klor eller -CH3, Z är CH2 eller S, is n är 0 - 5, Y är fenyl eller 1,4-cyklohexadien-l-yl, R-l och R2 är väte eller hydroxi, förutsatt, att R.,^ och R2 bäda ej är väteatomer, och R3 är -C02H, -COO (C3_4-alkyl) eller -(C=0)-R4/ där R4 20 är C1.4-alkyl.
2. Komplex enligt patentkrav 1, känne-t e c k n a t därav, att nämnda komplex är cef radin :metylparaben.H20, cefaklor:metylparaben.3 H 20, cefa-klor(4-hydroxiacetofenon), cefalexin:metylparaben.H20, lo- **· 25 rakarbef imetylparaben, lorakarbef: etylparaben, lorakar- bef:propylparaben eller lorakarbef:(metylester av 3-hydroxibensoesyra).(1 eller 5)H20.
3. Förfarande för framställning av ett β-laktam-komplex med formeln (VI) , 30 tfH2 h
35 Q/ Λ (VI) COOH • - 22 1 0 6 4 6 0 där X är klor eller -CH3, Z är CH2 eller S, och Y är fenyl eller 1,4-cyklohexadien-l-yl, 5 kännetecknat därav, att det omfattar ett steg, där ett bicykliskt β-laktam/parabenkomplex med formeln - v V yf Ί .,-/>»,. *
0 A=/ COOH {v) 15 där X, Y och Z är ovarx definierade, n är 0 - 5, R3 och R2 är väte eller hydroxi, förutsatt, att R3 och R2 bäda ej är väteatomer, och R3 är C02H, -COO (C^-alkyl) eller -(C=0)-R4/ där R4 är C-^-alkyl, 20 loses i ett surt organiskt lösningsmedel eller en sur vattenhaltig organisk lösningsmedelsblandning och där-efter tillsätts en tillräcklig mängd av en bas för utfäll-ning av föreningen med formeln (VI).
4. Förfarande enligt patentkrav 3, k ä n n e - /. 25 t e c k n a t därav, att nämnda komplex är cefra- din:metylparaben.H20, cefaklorrmetylparaben.3 H20, cefak- lor:4-hydroxiacetofenon, cefalexin:metylparaben.H20, lora-karbef:metylparaben, lorakarbef:etylparaben, lorakarbef:-propylparaben eller lorakarbef:(metylester av 3-hydroxi- 30 bensoesyra) . (1 eller 5)H20.
5. Förfarande för framställning av ett β-laktam-derivat med formeln ·- 35 23 106460 nh2 u 5 cT Ύ (vi) COOH där X är klor eller -CH3i Z är CH2 eller S, och ίο Y är fenyl eller 1,4-cyklohexadien-l-yl, kännetecknat därav, att det omf attar ett steg, där ett bicykliskt β-laktam/parabenkomplex med formeln 15 "Φ* H ζ R2 νΛ^Υ-ί^ ^ Π : R1—U 'V—R3 * ηΗ20 o^y\ Λ=/
20 COOH (ν> där X, Υ och Ζ är ovan definierade, n är 0 - 5, Rx och R2 är väte eller hydroxi, förutsatt, att R3 och R2 bäda ej är väteatomer, och R3 är C02H, -COO (C1.4~alkyl) eller -(C=0)-R4, där R4 25 är C1.4-alkyl, loses i ett basiskt organiskt lösningsmedelssys-tem eller en basisk vattenhaltig organiskt lösningsmedels-blandning och därefter tillsätts en tillräcklig raängd av en syra för utfällning av föreningen med formeln (VI). 30 6. Förfarande enligt patentkrav 3, känne tecknat därav, att nämnda komplex är cefradin:-metylparaben.H20, cefaklor:metylparaben.3 H20, cefaklor:4-hydroxiacetofenon, cefalexinrmetylparaben.H20, lorakar bef :metylparäben, lorakarbef:etylparaben, lorakarbef:pro- 35 pylparaben eller lorakarbef:(metylester av 3-hydroxiben-soesyra) . (1 eller 5)H20. «
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/084,651 US5412094A (en) | 1993-06-28 | 1993-06-28 | Bicyclic beta-lactam/paraben complexes |
| US8465193 | 1993-06-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI943081A0 FI943081A0 (sv) | 1994-06-27 |
| FI943081A FI943081A (sv) | 1994-12-29 |
| FI106460B true FI106460B (sv) | 2001-02-15 |
Family
ID=22186328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI943081A FI106460B (sv) | 1993-06-28 | 1994-06-27 | Bicykliska beta-laktam/parabenkomplexer och förfarande för framställning av beta-laktamderivat |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5412094A (sv) |
| EP (1) | EP0637587B1 (sv) |
| JP (1) | JPH0748383A (sv) |
| KR (1) | KR950000707A (sv) |
| CN (1) | CN1044246C (sv) |
| AT (1) | ATE159942T1 (sv) |
| AU (1) | AU674226B2 (sv) |
| BR (1) | BR9402561A (sv) |
| CA (1) | CA2126401A1 (sv) |
| CO (1) | CO4230098A1 (sv) |
| CZ (1) | CZ285452B6 (sv) |
| DE (1) | DE69406607T2 (sv) |
| DK (1) | DK0637587T3 (sv) |
| ES (1) | ES2110185T3 (sv) |
| FI (1) | FI106460B (sv) |
| GR (1) | GR3025563T3 (sv) |
| HU (1) | HU219484B (sv) |
| IL (1) | IL110103A (sv) |
| NO (1) | NO305480B1 (sv) |
| NZ (1) | NZ260791A (sv) |
| PE (1) | PE57294A1 (sv) |
| PL (1) | PL177317B1 (sv) |
| RU (1) | RU2134265C1 (sv) |
| YU (1) | YU40694A (sv) |
| ZA (1) | ZA944376B (sv) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5550231A (en) * | 1993-06-15 | 1996-08-27 | Eli Lilly And Company | Loracarbef hydrochloride C1-C3 alcohol solvates and uses thereof |
| US6001996A (en) * | 1995-05-11 | 1999-12-14 | Eli Lilly And Company | Complexes of cephalosporins and carbacephalosporins with parabens |
| US7927613B2 (en) | 2002-02-15 | 2011-04-19 | University Of South Florida | Pharmaceutical co-crystal compositions |
| US20090088443A1 (en) * | 2002-02-15 | 2009-04-02 | Julius Remenar | Novel crystalline forms of conazoles and methods of making and using the same |
| US20100311701A1 (en) * | 2002-02-15 | 2010-12-09 | Transform Pharmaceuticals, Inc | Pharmaceutical Co-Crystal Compositions |
| US7790905B2 (en) * | 2002-02-15 | 2010-09-07 | Mcneil-Ppc, Inc. | Pharmaceutical propylene glycol solvate compositions |
| IL163846A0 (en) * | 2002-03-01 | 2005-12-18 | Univ South Florida | Multiple-component solid phases containing at least one active pharmaceutical ingredient |
| US20070059356A1 (en) * | 2002-05-31 | 2007-03-15 | Almarsson Oern | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| CN100360117C (zh) * | 2002-06-21 | 2008-01-09 | 转化医药公司 | 具有提高的溶出度的药物组合物 |
| US8183290B2 (en) * | 2002-12-30 | 2012-05-22 | Mcneil-Ppc, Inc. | Pharmaceutically acceptable propylene glycol solvate of naproxen |
| KR20120115492A (ko) * | 2009-11-06 | 2012-10-18 | 바스프 에스이 | ４―히드록시 벤조산 및 선택된 살충제의 결정질 복합체 |
| CN105997931A (zh) * | 2016-07-19 | 2016-10-12 | 南京正宽医药科技有限公司 | 一种头孢克肟胶囊及其制备方法 |
| CN113845529B (zh) * | 2021-10-15 | 2024-02-27 | 东南大学 | 一种头孢氨苄共晶化合物及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3531481A (en) * | 1969-04-21 | 1970-09-29 | Lilly Co Eli | Method for manufacture of crystalline cephalosporin |
| GB1510794A (en) * | 1974-08-06 | 1978-05-17 | Univ Kingston | 1-oxacephems and intermediates therefor |
| AT363594B (de) * | 1978-02-01 | 1981-08-10 | Biochemie Gmbh | Verfahren zur herstellung eines neuen formamidkomplexes von 7-beta-(d-2-amino-2-phenylacetamido)-3-methylceph-3-emcarbonsaeure |
| PH21016A (en) * | 1982-07-23 | 1987-06-30 | Meiji Seika Kaisha | 2-alkyl-1-oxa-dethia-cephalosporin derivatives and process for producing said compound |
| US4782144A (en) * | 1987-09-14 | 1988-11-01 | Eli Lilly And Company | 1-carba(dethia)-3-hydroxy-3-cephem ester crystalline and crystalline solvate thereof |
| DD273634A5 (de) * | 1987-10-06 | 1989-11-22 | ����@�����@�����@����k�� | Verfahren zur herstellung eines kristallinen monohydrats eines 1-carbacephalosporins |
| EP0341991A3 (en) * | 1988-05-13 | 1991-08-28 | Eli Lilly And Company | Method for recovery of antibiotics from mother liquors and novel pharmaceutically-acceptable salts thereof |
| CA2002596A1 (en) * | 1988-11-14 | 1990-05-14 | Thomas M. Eckrich | Hydrates of b-lactam antibiotic |
| US4977257A (en) * | 1988-11-14 | 1990-12-11 | Eli Lilly And Company | DMF solvates of a β-lactam antibiotic |
| US5142042A (en) * | 1989-01-23 | 1992-08-25 | Purzer Pharmaceutical Co., Ltd. | Process for preparing well crystallized alkali metal salts of 3, 7-substituted 7-aminocephalosporanic acid derivatives |
-
1993
- 1993-06-28 US US08/084,651 patent/US5412094A/en not_active Expired - Fee Related
-
1994
- 1994-06-20 AT AT94304442T patent/ATE159942T1/de not_active IP Right Cessation
- 1994-06-20 DK DK94304442.0T patent/DK0637587T3/da active
- 1994-06-20 EP EP94304442A patent/EP0637587B1/en not_active Expired - Lifetime
- 1994-06-20 ES ES94304442T patent/ES2110185T3/es not_active Expired - Lifetime
- 1994-06-20 ZA ZA944376A patent/ZA944376B/xx unknown
- 1994-06-20 DE DE69406607T patent/DE69406607T2/de not_active Expired - Fee Related
- 1994-06-20 CZ CZ941519A patent/CZ285452B6/cs not_active IP Right Cessation
- 1994-06-20 NZ NZ260791A patent/NZ260791A/en unknown
- 1994-06-20 PE PE1994244825A patent/PE57294A1/es not_active Application Discontinuation
- 1994-06-21 CA CA002126401A patent/CA2126401A1/en not_active Abandoned
- 1994-06-21 NO NO942364A patent/NO305480B1/no not_active IP Right Cessation
- 1994-06-23 IL IL11010394A patent/IL110103A/xx not_active IP Right Cessation
- 1994-06-24 PL PL94303977A patent/PL177317B1/pl unknown
- 1994-06-24 CO CO94027493A patent/CO4230098A1/es unknown
- 1994-06-24 AU AU65950/94A patent/AU674226B2/en not_active Ceased
- 1994-06-25 KR KR1019940014713A patent/KR950000707A/ko active IP Right Grant
- 1994-06-27 CN CN94106572A patent/CN1044246C/zh not_active Expired - Fee Related
- 1994-06-27 JP JP6144637A patent/JPH0748383A/ja active Pending
- 1994-06-27 YU YU40694A patent/YU40694A/sh unknown
- 1994-06-27 BR BR9402561A patent/BR9402561A/pt not_active Application Discontinuation
- 1994-06-27 RU RU94022484A patent/RU2134265C1/ru active
- 1994-06-27 FI FI943081A patent/FI106460B/sv active
- 1994-06-28 HU HU9401935A patent/HU219484B/hu not_active IP Right Cessation
-
1997
- 1997-12-02 GR GR970403213T patent/GR3025563T3/el unknown
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