IL109989A - Loracarbef hydrochloride c1-c3 alcohol solvates and uses thereof - Google Patents
Loracarbef hydrochloride c1-c3 alcohol solvates and uses thereofInfo
- Publication number
- IL109989A IL109989A IL109989A IL10998994A IL109989A IL 109989 A IL109989 A IL 109989A IL 109989 A IL109989 A IL 109989A IL 10998994 A IL10998994 A IL 10998994A IL 109989 A IL109989 A IL 109989A
- Authority
- IL
- Israel
- Prior art keywords
- loracarbef
- compound
- hydrochloride
- alcohol
- formula
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 81
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 239000012453 solvate Substances 0.000 title claims abstract description 36
- 229960001977 loracarbef Drugs 0.000 title claims description 47
- JAPHQRWPEGVNBT-UTUOFQBUSA-M loracarbef anion Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CC[C@@H]32)C([O-])=O)=O)N)=CC=CC=C1 JAPHQRWPEGVNBT-UTUOFQBUSA-M 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 229910001868 water Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 claims description 7
- 238000002441 X-ray diffraction Methods 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 3
- RMIGTEGRHJUHHM-UHFFFAOYSA-N propan-1-ol;hydrochloride Chemical compound Cl.CCCO RMIGTEGRHJUHHM-UHFFFAOYSA-N 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract description 5
- GPYKKBAAPVOCIW-HSASPSRMSA-N (6r,7s)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate Chemical compound O.C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CC[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 GPYKKBAAPVOCIW-HSASPSRMSA-N 0.000 description 50
- 235000019441 ethanol Nutrition 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002002 slurry Substances 0.000 description 10
- 150000004682 monohydrates Chemical group 0.000 description 9
- 238000005917 acylation reaction Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000010933 acylation Effects 0.000 description 6
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- -1 Loracarbef Hydrochloride Methanolate Loracarbef dihydrate Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
- 238000009838 combustion analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000004683 dihydrates Chemical group 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/077,305 US5550231A (en) | 1993-06-15 | 1993-06-15 | Loracarbef hydrochloride C1-C3 alcohol solvates and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL109989A0 IL109989A0 (en) | 1994-10-07 |
| IL109989A true IL109989A (en) | 1998-06-15 |
Family
ID=22137301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL109989A IL109989A (en) | 1993-06-15 | 1994-06-13 | Loracarbef hydrochloride c1-c3 alcohol solvates and uses thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5550231A (ja) |
| EP (1) | EP0629625B1 (ja) |
| JP (1) | JP3474635B2 (ja) |
| KR (1) | KR100310947B1 (ja) |
| AT (1) | ATE225789T1 (ja) |
| BR (1) | BR9402406A (ja) |
| CA (1) | CA2125762A1 (ja) |
| DE (1) | DE69431498T2 (ja) |
| ES (1) | ES2184751T3 (ja) |
| FI (1) | FI108134B (ja) |
| HU (1) | HUT67489A (ja) |
| IL (1) | IL109989A (ja) |
| TW (1) | TW380139B (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA978515B (en) * | 1996-09-23 | 1999-03-23 | Lilly Co Eli | Intermediates and process for preparing olanzapine |
| CA2506872A1 (en) * | 2002-11-21 | 2004-06-03 | Ranbaxy Laboratories Limited | Monohydrate solvates of loracarbef |
| EP1603399B1 (fr) * | 2003-03-12 | 2009-12-23 | LESAFFRE et Cie | Levain panaire, son utilisation et produits de boulangerie cuits susceptibles d'être obtenus |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168376A (en) * | 1978-06-05 | 1979-09-18 | Eli Lilly And Company | Process for crystalline sodium cefamandole |
| US4316958A (en) * | 1979-02-10 | 1982-02-23 | Kyowa Hakko Kogyo Co., Ltd. | Process for producing optically active cephalosporin analogs |
| JPS5672698A (en) * | 1979-11-14 | 1981-06-16 | Kyowa Hakko Kogyo Co Ltd | Preparation of optically active cephalosporin analogue |
| US4332896A (en) * | 1979-04-14 | 1982-06-01 | Kyowa Hakko Kogyo Co., Ltd. | Process for producing cephalosporin analogs |
| US4775751A (en) * | 1985-06-03 | 1988-10-04 | Eli Lilly & Company | Process for cephalexin hydrochloride alcoholates |
| YU46699B (sh) * | 1987-10-06 | 1994-04-05 | Eli Lilly And Co. | Kristalni monohidratni oblik 1-karbacefalosporina |
| US4977257A (en) * | 1988-11-14 | 1990-12-11 | Eli Lilly And Company | DMF solvates of a β-lactam antibiotic |
| CA2002596A1 (en) * | 1988-11-14 | 1990-05-14 | Thomas M. Eckrich | Hydrates of b-lactam antibiotic |
| CA2002597C (en) * | 1988-11-14 | 1999-03-23 | Thomas M. Eckrich | Solvates of b-lactam antibiotic |
| CA2034592C (en) * | 1990-01-26 | 2001-06-05 | Ralph R. Pfeiffer | Crystalline hydrochloride of new beta-lactam antibiotic and process therefor |
| US5057607A (en) * | 1990-06-08 | 1991-10-15 | Eli Lilly And Company | Enantiomerically selective biocatalyzed acylation |
| US5352782A (en) * | 1993-06-04 | 1994-10-04 | Eli Lilly And Company | Process for preparing crystalline β-lactam monohydrate |
| US5399686A (en) * | 1993-06-04 | 1995-03-21 | Eli Lilly And Company | Loracarbef isopropanolate and a process for converting loracarbef isopropanolate to loracarbef monohydrate |
| US5374719A (en) * | 1993-06-04 | 1994-12-20 | Eli Lilly And Company | Process for converting loracarbef dihydrate to loracarbef monohydrate |
| US5412094A (en) * | 1993-06-28 | 1995-05-02 | Eli Lilly And Company | Bicyclic beta-lactam/paraben complexes |
-
1993
- 1993-06-15 US US08/077,305 patent/US5550231A/en not_active Expired - Lifetime
-
1994
- 1994-06-11 TW TW083105321A patent/TW380139B/zh not_active IP Right Cessation
- 1994-06-13 IL IL109989A patent/IL109989A/en not_active IP Right Cessation
- 1994-06-13 AT AT94304230T patent/ATE225789T1/de not_active IP Right Cessation
- 1994-06-13 DE DE69431498T patent/DE69431498T2/de not_active Expired - Fee Related
- 1994-06-13 EP EP94304230A patent/EP0629625B1/en not_active Expired - Lifetime
- 1994-06-13 FI FI942798A patent/FI108134B/fi not_active IP Right Cessation
- 1994-06-13 KR KR1019940013210A patent/KR100310947B1/ko not_active Expired - Fee Related
- 1994-06-13 JP JP13023494A patent/JP3474635B2/ja not_active Expired - Fee Related
- 1994-06-13 CA CA002125762A patent/CA2125762A1/en not_active Abandoned
- 1994-06-13 HU HU9401765A patent/HUT67489A/hu unknown
- 1994-06-13 ES ES94304230T patent/ES2184751T3/es not_active Expired - Lifetime
- 1994-06-14 BR BR9402406A patent/BR9402406A/pt not_active Application Discontinuation
-
1995
- 1995-05-18 US US08/444,124 patent/US5578720A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69431498D1 (de) | 2002-11-14 |
| TW380139B (en) | 2000-01-21 |
| HUT67489A (en) | 1995-04-28 |
| FI942798L (fi) | 1994-12-16 |
| CA2125762A1 (en) | 1994-12-16 |
| ATE225789T1 (de) | 2002-10-15 |
| IL109989A0 (en) | 1994-10-07 |
| FI942798A0 (fi) | 1994-06-13 |
| ES2184751T3 (es) | 2003-04-16 |
| US5550231A (en) | 1996-08-27 |
| DE69431498T2 (de) | 2003-06-26 |
| KR950000704A (ko) | 1995-01-03 |
| US5578720A (en) | 1996-11-26 |
| JP3474635B2 (ja) | 2003-12-08 |
| HU9401765D0 (en) | 1994-09-28 |
| JPH0770122A (ja) | 1995-03-14 |
| FI108134B (fi) | 2001-11-30 |
| EP0629625B1 (en) | 2002-10-09 |
| EP0629625A1 (en) | 1994-12-21 |
| KR100310947B1 (ko) | 2001-12-28 |
| BR9402406A (pt) | 1995-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |