KR950700311A - 3-세펨-4-카복실산 유도체의 정제방법(Process for the purification of a 3-cephem-4-carboxylic acid derivatives) - Google Patents
3-세펨-4-카복실산 유도체의 정제방법(Process for the purification of a 3-cephem-4-carboxylic acid derivatives)Info
- Publication number
- KR950700311A KR950700311A KR1019940702673A KR19940702673A KR950700311A KR 950700311 A KR950700311 A KR 950700311A KR 1019940702673 A KR1019940702673 A KR 1019940702673A KR 19940702673 A KR19940702673 A KR 19940702673A KR 950700311 A KR950700311 A KR 950700311A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- carboxylic acid
- amino
- propen
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract 12
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract 5
- -1 amine salt Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 12
- 239000011734 sodium Substances 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- 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 claims 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 5
- 229910052744 lithium Inorganic materials 0.000 claims 5
- 229910052708 sodium Inorganic materials 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- 229910052700 potassium Inorganic materials 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- 239000011877 solvent mixture Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 claims 1
- 239000003463 adsorbent Substances 0.000 claims 1
- 238000005377 adsorption chromatography Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229940124587 cephalosporin Drugs 0.000 claims 1
- 150000001780 cephalosporins Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 235000011056 potassium acetate Nutrition 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 230000003381 solubilizing effect Effects 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000001271 cephalosporin group Chemical group 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ATA191/92 | 1992-02-05 | ||
| AT0019192A AT399876B (de) | 1992-02-05 | 1992-02-05 | Verfahren zur abreicherung von 7-amino-3-((e)-1- propen-1-yl)-3-cephem-4-carbonsäure |
| GB9225666.8 | 1992-12-09 | ||
| GB929225666A GB9225666D0 (en) | 1992-12-09 | 1992-12-09 | Process for the depletion of 7-amino-3-((e)-propen-1-yl)-3-cephem-4-carboxylic acid |
| PCT/EP1992/002965 WO1993016084A1 (en) | 1992-02-05 | 1992-12-21 | Process for the purification of a 3-cephem-4-carboxylic acid derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR950700311A true KR950700311A (ko) | 1995-01-16 |
Family
ID=25591794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940702673A Expired - Lifetime KR950700311A (ko) | 1992-02-05 | 1992-12-21 | 3-세펨-4-카복실산 유도체의 정제방법(Process for the purification of a 3-cephem-4-carboxylic acid derivatives) |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US5869648A (forum.php) |
| EP (2) | EP1103555B1 (forum.php) |
| JP (1) | JP2825655B2 (forum.php) |
| KR (1) | KR950700311A (forum.php) |
| AT (2) | ATE253583T1 (forum.php) |
| CA (1) | CA2124322C (forum.php) |
| DE (2) | DE69233249T2 (forum.php) |
| DK (1) | DK0630380T3 (forum.php) |
| ES (2) | ES2162812T3 (forum.php) |
| GR (1) | GR3036985T3 (forum.php) |
| PT (1) | PT630380E (forum.php) |
| SG (1) | SG48415A1 (forum.php) |
| TW (1) | TW230775B (forum.php) |
| WO (1) | WO1993016084A1 (forum.php) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0658558T3 (da) | 1993-11-17 | 2001-04-17 | Biochemie Gmbh | Adskillelse af cephalosporinisomere |
| US5648378A (en) * | 1995-06-07 | 1997-07-15 | Research Corporation Technologies, Inc. | 2-iminochromene derivatives as inhibitors of protein tyrosine kinase |
| AT403049B (de) * | 1995-08-14 | 1997-10-27 | Biochemie Gmbh | Abreicherung von 7-adca in 3-vinyl-aca |
| AT405283B (de) * | 1997-04-04 | 1999-06-25 | Biochemie Gmbh | Neues kristallines 7-(z)-(2-(2-aminothiazol-4-yl) -2-hydroxyiminoacetamido)-3-vinyl-3-cephem-4- carbonsäure dicyclohexylammoniumsalz und verfahren zu dessen herstellung |
| AT406773B (de) * | 1998-04-02 | 2000-08-25 | Biochemie Gmbh | Neues salz von 7-(2-(aminothiazol-4yl)-2- |
| GB0118764D0 (en) * | 2001-08-01 | 2001-09-26 | Biochemie Gmbh | Organic compounds |
| EP1554289B1 (en) * | 2002-08-13 | 2011-03-09 | Sandoz Ag | A cefdinir intermediate |
| CN1711271A (zh) * | 2002-10-08 | 2005-12-21 | 兰贝克赛实验室有限公司 | 制备富含(z)－异构体的7－氨基－3－丙烯－1－基－3－头孢烯－4－羧酸的方法 |
| US6903211B2 (en) * | 2002-10-30 | 2005-06-07 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of 3-propenyl cephalosporin DMF solvate |
| MXPA05010205A (es) * | 2003-03-24 | 2005-11-08 | Acs Dobfar Spa | Nuevo cristal del acido 7-[2-(2- aminotiazol- 4-il)-2- hidroxiiminoacetamido] -3-vinil-3- cefem-4 -carboxilico (isomero syn) y metodo para la preparacion del mismo. |
| WO2005100369A1 (en) * | 2004-04-13 | 2005-10-27 | Ranbaxy Laboratories Limited | Depletion of e-isomers in preparation of z-enriched 3-(2-substituted vinyl) cephalosporins |
| JP4046708B2 (ja) * | 2004-06-04 | 2008-02-13 | 明治製菓株式会社 | ３−アルケニルセフェム化合物の製造方法 |
| GB2421024A (en) * | 2004-12-07 | 2006-06-14 | Sandoz Ag | Cefdinir crystalline form C |
| US20070128268A1 (en) * | 2005-12-07 | 2007-06-07 | Herwig Jennewein | Pharmaceutical compositions comprising an antibiotic |
| EP2367118A1 (en) * | 2010-03-15 | 2011-09-21 | GMC Software AG | Method and devices for generating two-dimensional visual objects |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769277A (en) * | 1970-01-23 | 1973-10-30 | Glaxo Lab Ltd | Preparation of delta3-4 carboxy cephalosporins having a 3-vinyl or substituted 3-vinyl group |
| US4107431A (en) * | 1970-01-23 | 1978-08-15 | Glaxo Laboratories Limited | Δ3 -3-Vinyl or substituted vinyl-4-carboxy cephalosporins |
| US4110534A (en) * | 1970-01-23 | 1978-08-29 | Glaxo Laboratories Limited | Process for the preparation of 3-vinyl and substituted vinyl cephalosporins |
| US4065620A (en) * | 1971-06-14 | 1977-12-27 | Eli Lilly And Company | 3-(Substituted) vinyl cephalosporins |
| US4520022A (en) | 1983-01-28 | 1985-05-28 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| ZM884A1 (en) | 1983-01-28 | 1984-10-22 | Bristol Myers Co | Substituted vinyl cephalosporins |
| FR2580652B1 (fr) * | 1985-04-22 | 1989-01-06 | Bristol Myers Co | Acide 7-amino-3-propenylcephalosporanique et ses esters |
| US4699979A (en) | 1985-04-22 | 1987-10-13 | Bristol-Meyers Company | 7-amino-3-propenylcephalosporanic acid and esters thereof |
| US4874856A (en) * | 1985-06-24 | 1989-10-17 | Bristol-Myers Company | 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof |
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| US4694079A (en) * | 1985-07-29 | 1987-09-15 | Bristol-Myers Company | 3-propenyl cephalosporin solvates |
| US4727070A (en) * | 1985-11-25 | 1988-02-23 | Bristol-Myers Company | 3-Propenzl cephalosporin isomer separation process and derivative |
| US4847373A (en) * | 1987-02-26 | 1989-07-11 | Bristol-Myers Company | Production of 3-allyl- and 3-butenyl-3-cephems |
| DE3734005A1 (de) * | 1987-05-26 | 1988-12-15 | Bayer Ag | Substituierte vinylcephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4935508A (en) * | 1988-08-23 | 1990-06-19 | Bristol-Myers Company | Process for cephem prodrug esters |
| DE3933934A1 (de) * | 1989-10-03 | 1991-04-11 | Bayer Ag | Verfahren zur herstellung von 7-amino-3-((z)-1-propen-1-yl)-3-cephem-4-carbonsaeure |
| US5095012A (en) * | 1990-08-23 | 1992-03-10 | Bristol-Myers Squibb Company | Antibiotic c-7 catechol-substituted cephalosporin compounds, compositions, and method of use thereof |
| ES2157199T3 (es) * | 1991-03-08 | 2001-08-16 | Biochemie Gmbh | Nuevo procedimiento para la produccion de cefalosporinas y nuevos compuestos intermedios para este procedimiento. |
-
1992
- 1992-12-21 EP EP01104309A patent/EP1103555B1/en not_active Expired - Lifetime
- 1992-12-21 WO PCT/EP1992/002965 patent/WO1993016084A1/en active IP Right Grant
- 1992-12-21 EP EP93901714A patent/EP0630380B1/en not_active Expired - Lifetime
- 1992-12-21 DE DE69233249T patent/DE69233249T2/de not_active Expired - Fee Related
- 1992-12-21 AT AT01104309T patent/ATE253583T1/de not_active IP Right Cessation
- 1992-12-21 CA CA002124322A patent/CA2124322C/en not_active Expired - Fee Related
- 1992-12-21 KR KR1019940702673A patent/KR950700311A/ko not_active Expired - Lifetime
- 1992-12-21 PT PT93901714T patent/PT630380E/pt unknown
- 1992-12-21 DK DK93901714T patent/DK0630380T3/da not_active Application Discontinuation
- 1992-12-21 SG SG1996009496A patent/SG48415A1/en unknown
- 1992-12-21 AT AT93901714T patent/ATE205214T1/de not_active IP Right Cessation
- 1992-12-21 DE DE69232048T patent/DE69232048T2/de not_active Expired - Fee Related
- 1992-12-21 JP JP5513698A patent/JP2825655B2/ja not_active Expired - Lifetime
- 1992-12-21 ES ES93901714T patent/ES2162812T3/es not_active Expired - Lifetime
- 1992-12-21 ES ES01104309T patent/ES2210047T3/es not_active Expired - Lifetime
- 1992-12-29 TW TW081110453A patent/TW230775B/zh not_active IP Right Cessation
-
1995
- 1995-06-06 US US08/466,306 patent/US5869648A/en not_active Expired - Fee Related
-
1998
- 1998-11-12 US US09/190,200 patent/US6136967A/en not_active Expired - Lifetime
-
2000
- 2000-05-04 US US09/564,833 patent/US6333409B1/en not_active Expired - Fee Related
-
2001
- 2001-10-23 GR GR20010401855T patent/GR3036985T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0630380A1 (en) | 1994-12-28 |
| CA2124322C (en) | 2007-04-17 |
| ES2162812T3 (es) | 2002-01-16 |
| CA2124322A1 (en) | 1993-08-19 |
| JP2825655B2 (ja) | 1998-11-18 |
| WO1993016084A1 (en) | 1993-08-19 |
| ATE253583T1 (de) | 2003-11-15 |
| DE69233249T2 (de) | 2004-08-19 |
| DE69233249D1 (de) | 2003-12-11 |
| DK0630380T3 (da) | 2001-12-10 |
| JPH07503474A (ja) | 1995-04-13 |
| DE69232048D1 (de) | 2001-10-11 |
| US6136967A (en) | 2000-10-24 |
| DE69232048T2 (de) | 2002-07-04 |
| EP1103555B1 (en) | 2003-11-05 |
| GR3036985T3 (en) | 2002-01-31 |
| EP1103555A1 (en) | 2001-05-30 |
| ATE205214T1 (de) | 2001-09-15 |
| SG48415A1 (en) | 1998-04-17 |
| ES2210047T3 (es) | 2004-07-01 |
| EP0630380B1 (en) | 2001-09-05 |
| US6333409B1 (en) | 2001-12-25 |
| PT630380E (pt) | 2002-02-28 |
| US5869648A (en) | 1999-02-09 |
| TW230775B (forum.php) | 1994-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 19940804 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19971220 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19991018 Patent event code: PE09021S01D |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20000819 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
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