SE8603308L - CEPHALOSPORIN SALTS AND INJECTABLE PREPARATIONS - Google Patents
CEPHALOSPORIN SALTS AND INJECTABLE PREPARATIONSInfo
- Publication number
- SE8603308L SE8603308L SE8603308A SE8603308A SE8603308L SE 8603308 L SE8603308 L SE 8603308L SE 8603308 A SE8603308 A SE 8603308A SE 8603308 A SE8603308 A SE 8603308A SE 8603308 L SE8603308 L SE 8603308L
- Authority
- SE
- Sweden
- Prior art keywords
- alpha
- methyl
- salts
- crystalline
- dilution
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 150000001780 cephalosporins Chemical class 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 5
- -1 Cephalosporin Salts Chemical class 0.000 abstract 3
- 238000010790 dilution Methods 0.000 abstract 3
- 239000012895 dilution Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000013078 crystal Substances 0.000 abstract 2
- 238000002425 crystallisation Methods 0.000 abstract 2
- 230000008025 crystallization Effects 0.000 abstract 2
- 239000007972 injectable composition Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 238000000862 absorption spectrum Methods 0.000 abstract 1
- HVFLCNVBZFFHBT-ZKDACBOMSA-N cefepime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 HVFLCNVBZFFHBT-ZKDACBOMSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000002329 infrared spectrum Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
-
- 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Cephalosporin Salts and Injectable Compositions Crystalline sulfuric, di-nitric, mono-hydrochloric, dihydrochloric, and di- and sesqui-orthosphosphoric acid addition salts of 7-¢.alpha.-(2-aminothiazol-4-yl)-.alpha.-(Z)-methoxyimino-acetamido!-3-¢(1-methyl-1-pyrrolidinio)-methyl!-3-cephem-4-carboxylate are stable even at elevated temperatures. The crystalline sulfuric acid addition salt is made by forming an admixture of (a) at least one molar equivalent of sulfuric acid with (b) zwitterion in an amount so as to be present in the admixture at a concentration of greater than 25 milligrams/ml, causing crystallization, separating the crystals, washing and drying. The crystalline monohydrochloride, dihydrochloride, and orthophosphate salts are prepared by dissolving the zwitterion in the appropriate amount of acid, causing crystallization by adding acetone and isolating the crystal. Physical admixtures of the salts with certain bases in proportions to give a pH ranging from about 3 5 to about 7 on dilution with water provide injectable compositions on dilution. Brief Description of the Drawing Figure 1 is a graphical representation of the infra red absorption spectrum of crystalline 7-¢.alpha.-(2-aminothiazol-4-yl)-.alpha.- (Z)-methoxyiminoacetamido!-3-¢(1-methyl-1-pyrrolidinio)methyl!-3-cephem-4-carboxylate sulfate salt measured on a KBr dilution thereof. BMY-28142.H2SO4 - IR Spectrum.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76223585A | 1985-08-05 | 1985-08-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8603308D0 SE8603308D0 (en) | 1986-08-04 |
| SE8603308L true SE8603308L (en) | 1987-02-06 |
| SE469633B SE469633B (en) | 1993-08-09 |
Family
ID=25064475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8603308A SE469633B (en) | 1985-08-05 | 1986-08-04 | PHYSICAL MIXTURES OF CEPHALOSPORINE SALTS, CRYSTALLINE SULPHATE SALTS, AND A PROCEDURE FOR THE PREPARATION OF THESE |
Country Status (34)
| Country | Link |
|---|---|
| JP (1) | JPH0615548B2 (en) |
| KR (1) | KR930003121B1 (en) |
| AR (1) | AR243894A1 (en) |
| AT (1) | AT390957B (en) |
| AU (1) | AU597262B2 (en) |
| BE (1) | BE905219A (en) |
| CA (1) | CA1284994C (en) |
| CH (1) | CH675581A5 (en) |
| CS (2) | CS276849B6 (en) |
| CY (1) | CY1614A (en) |
| DD (2) | DD254941A5 (en) |
| DE (1) | DE3626375A1 (en) |
| DK (1) | DK162053C (en) |
| EG (1) | EG18003A (en) |
| ES (1) | ES2002112A6 (en) |
| FI (1) | FI84484C (en) |
| FR (1) | FR2585705B1 (en) |
| GB (1) | GB2179936B (en) |
| GR (1) | GR862055B (en) |
| HK (1) | HK99691A (en) |
| HU (1) | HU196602B (en) |
| IE (1) | IE59222B1 (en) |
| IL (1) | IL79608A (en) |
| IT (1) | IT1197067B (en) |
| LU (2) | LU88574I2 (en) |
| MY (1) | MY102212A (en) |
| NL (1) | NL8601991A (en) |
| OA (1) | OA08672A (en) |
| PT (1) | PT83134B (en) |
| SE (1) | SE469633B (en) |
| SG (1) | SG79791G (en) |
| SU (1) | SU1516013A3 (en) |
| YU (1) | YU45793B (en) |
| ZA (1) | ZA865842B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4883868A (en) * | 1984-12-27 | 1989-11-28 | Banyu Pharmaceutical Co., Ltd. | 7-amino-3-(substituted isoindolinium)methyl-3-cephem derivatives |
| US4959469A (en) * | 1984-12-27 | 1990-09-25 | Banyu Pharmaceutical Company, Ltd. | Crystalline cephalosporin compounds |
| US4910301A (en) * | 1985-08-05 | 1990-03-20 | Bristol-Myers Company | Cefepime cephalosporin salts |
| US5244891A (en) * | 1985-08-05 | 1993-09-14 | Bristol-Myers Squibb Company | Injectable compositions of cefepime dihydrochloride hydrate |
| US4808617A (en) * | 1985-12-18 | 1989-02-28 | Bristol-Myers Company | Lyophilized or precipitated cephalosporin zwitterion and salt combination |
| EP0321562B1 (en) * | 1987-06-25 | 1993-11-24 | Banyu Pharmaceutical Co., Ltd. | Crystalline cephalosporin compounds, process for their preparation, and intermediates for their preparation |
| JPH02101081A (en) * | 1988-10-08 | 1990-04-12 | Meiji Seika Kaisha Ltd | Crystalline dihydrochloride of cephalosporin derivative and production thereof |
| CA2011116C (en) * | 1989-03-06 | 1999-11-16 | Murray A. Kaplan | Lyophilized bmy-28142 dihydrochloride for parenteral use |
| CA2101571A1 (en) * | 1992-09-08 | 1994-03-09 | Elizabeth A. Garofalo | Crystalline dihydrate of a cephalosporin dihydrate salt and injectable compositions thereof |
| US5721359A (en) * | 1993-03-12 | 1998-02-24 | Pharmacia & Upjohn Company | Crystalline ceftiofur free acid |
| EP0638573A1 (en) * | 1993-08-10 | 1995-02-15 | Lucky Ltd. | Crystalline hydrates of cephalosporin and process for preparation thereof |
| WO2005063772A1 (en) | 2003-12-23 | 2005-07-14 | Sandoz Ag | Process for production of intermediates for use in cefalosporin synthesis |
| WO2008056221A2 (en) * | 2006-11-06 | 2008-05-15 | Orchid Chemicals & Pharmaceuticals Limited | Crystalline sulfate salt of cephalosporin antibiotic |
| DE102012101680A1 (en) * | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Pharmaceutical preparation containing an antiviral dihydroquinazoline derivative |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55151588A (en) * | 1979-05-14 | 1980-11-26 | Takeda Chem Ind Ltd | Preparation of cephalosporin salt crystal |
| CA1213882A (en) * | 1982-03-04 | 1986-11-12 | Jun Okumura | Cephalosporins |
| US4406899A (en) * | 1982-03-04 | 1983-09-27 | Bristol-Myers Company | Cephalosporins |
| US4525473A (en) * | 1983-03-30 | 1985-06-25 | Bristol-Myers Company | Cephalosporins |
| DE3419015A1 (en) * | 1984-05-22 | 1985-11-28 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING CEPHALOSPORINES |
| GB2165245B (en) * | 1984-10-01 | 1988-05-25 | Glaxo Group Ltd | Chemical compounds |
| GB8424692D0 (en) * | 1984-10-01 | 1984-11-07 | Glaxo Group Ltd | Chemical compounds |
-
1986
- 1986-07-28 FR FR8610892A patent/FR2585705B1/en not_active Expired
- 1986-07-28 CA CA000514766A patent/CA1284994C/en not_active Expired - Lifetime
- 1986-07-29 AR AR86304717A patent/AR243894A1/en active
- 1986-07-30 AU AU60694/86A patent/AU597262B2/en not_active Expired
- 1986-07-31 YU YU137186A patent/YU45793B/en unknown
- 1986-08-01 IE IE207886A patent/IE59222B1/en not_active IP Right Cessation
- 1986-08-01 FI FI863155A patent/FI84484C/en not_active IP Right Cessation
- 1986-08-04 CS CS903570A patent/CS276849B6/en unknown
- 1986-08-04 BE BE07217010A patent/BE905219A/en not_active IP Right Cessation
- 1986-08-04 CS CS865827A patent/CS276717B6/en unknown
- 1986-08-04 LU LU88574C patent/LU88574I2/en unknown
- 1986-08-04 GB GB8618989A patent/GB2179936B/en not_active Expired
- 1986-08-04 NL NL8601991A patent/NL8601991A/en not_active Application Discontinuation
- 1986-08-04 ZA ZA865842A patent/ZA865842B/en unknown
- 1986-08-04 CH CH3117/86A patent/CH675581A5/de not_active IP Right Cessation
- 1986-08-04 IL IL79608A patent/IL79608A/en not_active IP Right Cessation
- 1986-08-04 JP JP61183288A patent/JPH0615548B2/en not_active Expired - Lifetime
- 1986-08-04 SU SU864027914A patent/SU1516013A3/en active
- 1986-08-04 SE SE8603308A patent/SE469633B/en not_active IP Right Cessation
- 1986-08-04 PT PT83134A patent/PT83134B/en unknown
- 1986-08-04 DE DE19863626375 patent/DE3626375A1/en not_active Ceased
- 1986-08-04 IT IT21409/86A patent/IT1197067B/en active Protection Beyond IP Right Term
- 1986-08-04 DK DK371886A patent/DK162053C/en not_active IP Right Cessation
- 1986-08-04 GR GR862055A patent/GR862055B/en unknown
- 1986-08-04 LU LU86540A patent/LU86540A1/en unknown
- 1986-08-05 HU HU863376A patent/HU196602B/en unknown
- 1986-08-05 ES ES8600872A patent/ES2002112A6/en not_active Expired
- 1986-08-05 DD DD86293433A patent/DD254941A5/en unknown
- 1986-08-05 OA OA58918A patent/OA08672A/en unknown
- 1986-08-05 KR KR1019860006445A patent/KR930003121B1/en not_active Expired - Lifetime
- 1986-08-05 AT AT0211086A patent/AT390957B/en not_active IP Right Cessation
-
1987
- 1987-09-29 MY MYPI87002279A patent/MY102212A/en unknown
-
1988
- 1988-03-30 DD DD88314213A patent/DD268395A5/en unknown
-
1989
- 1989-08-04 EG EG489/86A patent/EG18003A/en active
-
1991
- 1991-10-02 SG SG797/91A patent/SG79791G/en unknown
- 1991-12-05 HK HK996/91A patent/HK99691A/en not_active IP Right Cessation
-
1992
- 1992-07-10 CY CY1614A patent/CY1614A/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SPCF | Application for supplementary protection certificate filed |
Free format text: 8603308 |
|
| SPCG | Supplementary protection certificate granted |
Free format text: 8603308, EXPIRES: 20080628 |
|
| NAL | Patent in force |
Ref document number: 8603308-1 Format of ref document f/p: F |
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| NUG | Patent has lapsed |