GB1503030A - Water soluble forms of triazolylthiomethyl cephem derivatives - Google Patents
Water soluble forms of triazolylthiomethyl cephem derivativesInfo
- Publication number
- GB1503030A GB1503030A GB53315/75A GB5331575A GB1503030A GB 1503030 A GB1503030 A GB 1503030A GB 53315/75 A GB53315/75 A GB 53315/75A GB 5331575 A GB5331575 A GB 5331575A GB 1503030 A GB1503030 A GB 1503030A
- Authority
- GB
- United Kingdom
- Prior art keywords
- salt
- solvent
- alkali metal
- acetaldehyde
- suspension
- 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
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001782 cephems Chemical class 0.000 title 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 10
- UOCJDOLVGGIYIQ-HTCLMOQTSA-N (6R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N[C@@H](C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=CN=NN2)C(=O)O)C1=O)C1=CC=C(C=C1)O UOCJDOLVGGIYIQ-HTCLMOQTSA-N 0.000 abstract 5
- 229910052783 alkali metal Inorganic materials 0.000 abstract 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- -1 cephem compounds Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- 239000000725 suspension Substances 0.000 abstract 4
- 239000002585 base Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000012453 solvate Substances 0.000 abstract 3
- 150000001340 alkali metals Chemical group 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000009472 formulation Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 229960001269 glycine hydrochloride Drugs 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 239000007787 solid Substances 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
-
- 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
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material 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)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
1503030 Triazolylthiomethyl cephem compounds BRISTOL-MYERS CO 31 Dec 1975 [2 Jan 1975] 53315/75 Heading C2C Novel compounds of the Formula (I) wherein R is an alkali metal, preferably Na or K, may be prepared (1) by treating an aqueous suspension of 7-[D-α-amino-α-(p-hydroxyphenyl)acetamido] - 3 - (1,2,3 - triazol - 5- ylthiomethyl) - 3 - cephem - 4 - carboxylic acid (II) or a solvate or hydrate thereof with acetaldehyde and sufficient water-soluble alkali metal base to raise the pH of the mixture to between 5À5 and 8 and to form a solution of the desired salt of (I), then recovering the salt from solution; or (2) forming a suspension of (II) or a solvate or hydrate thereof in an inert organic solvent, which is a solvent for the triethylamine salt of the acetaldehyde reaction product of (II) and a non-solvent for the alkali metal salt of (I), treating the suspension with acetaldehyde and sufficient triethylamine to form a salt of the acetaldehyde reaction product of (II), and precipitating the desired alkali metal salt of (I) by adding a solvent-soluble sodium or potassium base; or (3) forming a suspension of (II) or a solvate or hydrate thereof in an inert organic solvent, which is a non-solvent for the alkali metal salt (I), treating the suspension with acetaldehyde and a solvent soluble base in amount sufficient to raise pH to 5-5 to 8, and recovering the desired salt (I). Pharmaceutical compositions suitable on reconstitution with water for use as parenterally administrable antibiotic formulations comprise a compound of Formula I as defined above and a solid pharmaceutically acceptable water-soluble organic acid or glycine hydrochloride present in such amount that the pH of the reconstituted formulation is between 5 and 6.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53786875A | 1975-01-02 | 1975-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1503030A true GB1503030A (en) | 1978-03-08 |
Family
ID=24144441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB53315/75A Expired GB1503030A (en) | 1975-01-02 | 1975-12-31 | Water soluble forms of triazolylthiomethyl cephem derivatives |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS6052717B2 (en) |
| GB (1) | GB1503030A (en) |
| HK (1) | HK41081A (en) |
| KE (1) | KE3151A (en) |
| MY (1) | MY8300207A (en) |
-
1975
- 1975-12-31 GB GB53315/75A patent/GB1503030A/en not_active Expired
-
1976
- 1976-01-01 JP JP51000567A patent/JPS6052717B2/en not_active Expired
-
1981
- 1981-08-12 KE KE3151A patent/KE3151A/en unknown
- 1981-08-20 HK HK410/81A patent/HK41081A/en unknown
-
1983
- 1983-12-30 MY MY207/83A patent/MY8300207A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6052717B2 (en) | 1985-11-20 |
| KE3151A (en) | 1981-08-28 |
| JPS5191291A (en) | 1976-08-10 |
| HK41081A (en) | 1981-08-28 |
| MY8300207A (en) | 1983-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |