Meiac
Cefditoren Pivoxil
CAS: 117467-28-4
Molecular Formula: C25H28N6O7S3
Meiac - Names and Identifiers
Meiac - Physico-chemical Properties
| Molecular Formula | C25H28N6O7S3 |
| Molar Mass | 620.72 |
| Density | 1.55±0.1 g/cm3(Predicted) |
| Melting Point | 207-209°C |
| Specific Rotation(α) | D20 -48.5° (c = 0.5 in methanol) |
| Solubility | DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly, Heated) |
| Appearance | Solid |
| Color | Off-White to Pale Yellow |
| Merck | 14,1921 |
| pKa | 8.08±0.60(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.71 |
| In vitro study | The MIC50/MIC90 of Cefditoren for Moraxella catarrhalis and Haemophilus influenzae were 0.12/0.5 and ≤ 0.008/0.015 mg/mL, respectively. Cefditoren (MIC(90), 0.5 mg/mL) was 4-to 128-fold more effective than other beta-lactams in the treatment of Diplococcus Pneumonia, and acting on beta-hemolytic streptococci is the most effective beta-lactam (including penicillin). Cefditoren (MIC(90),mg/mL/% susceptible) tested for Haemophilus influenzae (0.03/100) and Moraxella catarrhalis (0.06-0.5/100) the activity of is equivalent to Cefixime and is significantly higher than cefaclor. Cefditoren exhibited a T(1/2) of 200-2 hours, C(max) in terms of Cefditoren pharmacokinetics at doses of 400 or 1.5 mg pivoxil. Values were 2.8 and 4.6 mg/mL, respectively. Cefditoren has a broad spectrum of antibacterial activity against a number of clinically important β-lactamase resistant gram-positive and gram-negative species. Cefditoren is also effective against methicillin-susceptible S. Aureus strains. Cefditoren acts on most common isolated respiratory pathogens and is more effective than other orally administered antibiotics. Cefditoren up-regulated the expression levels of Mrp2,Bcrp and Oat2, and down-regulated P-gp and Oct 1 mRNA expression. |
Meiac - Risk and Safety
| RTECS | XI0367800 |
Meiac - Synthetic Methods
synthesis of 1 1 (see figure 1)
1.1 21 was reacted with NaI and TPP (triphenylphosphine) with stirring, and treated with aqueous NaOH. Separation of the organic phase, and 3 occurred Wittig reaction to get 22. Phenol dissolved 22, stirred to remove 2 a protecting group of methoxybenzyl, and then mNaHCO aqueous solution extraction, acidification and precipitation, that is, 23. 23 dissolved in DMF, add K,CO, and then react with methyl iodide, 24. With PC1, pyridine, methanol to remove 24 of the 7 one protecting group phenyl acetyl group, get 25. 25 and 36 [I. E. 2 (2 triphenylmethylamino 2 thiazolyl) a 2 methoxyimine acetic acid] in pyridine and. Under the action of POCI condensation reaction, column chromatography separation was 26. 26 Removal of triphenylmethyl (Tri) with CF COOH to give 1
1.2 21 with PC1, pyridine, methanol to remove 7 a protective group of phenyl acetyl group 27. 27 in the role of DCC or pyridine and POC1 in the acylation reaction with 36 29. 29 with NaI, TPP stirring reaction, and then add NaOH aqueous solution treatment, and 3 Wittig reaction to 3O,3O removal of the protective group to 2. 2 (or its sodium salt, potassium salt) and methyl iodide pivalate esterification 1
1.3 27 with NaI, TPP stirring reaction, and then add NaOH aqueous solution treatment, and 3 Wittig reaction to 28 (can also be obtained from 22 with PC1, pyridine, CH OH to remove the phenyl acetyl group), condensation reaction between 28 and 36 to obtain 30, and then 1 by 1.2 method
1.4 28 with phenol, anisole removed 2 a methoxybenzyl to 20,20 and 37 (aminothiazole acid benzothiazole active ester, benzotriazole active ester, phosphite, oxazole Ester, etc.) under the action of alkalizing agent, the condensation reaction yields 2, then 1
1.5 23 with PC1, pyridine, CH OH to remove phenylacetyl group (or: 23 dissolved = J = NaHCO, aqueous solution, with penicillin acylase Pen-G to remove phenylacetyl group) to obtain 2O, then get 2 by 1.4, get 1
1.6 34G joint JR = A SO CN(CH ),] or in DCC(R = OH) under the Action of 20 reaction to get 35,35 synthesis of thiazole ring by ring closure reaction with thiourea to obtain 2, 1
1.7 31 (ie: cefotaxime acid) with TMSC (trimethylchlorosilane) and HMDS (hexamethyldisilylamine) silanization, and then TMSI iodine for 32. 32 and PPh, NaI, the role of alkali to Ye Lide 33. 33 and 3 for Wittig reaction, and remove the protective group, get 2, then get 1
2 intermediate 3 (see figure 2)
2.1 acetone and thiourea under the action of iodine, heating reflux, ring closure and 4. POC1 /DMF acts on 4 to introduce a formyl group at one of its 5 positions to give 5. Concentrated sulfuric acid acts on 5, performs diazotization reaction with NaNO, and then is treated with sodium hypophosphite, and finally removes the amino group to obtain 3T
2.2 6 under the action of initiator AIBN, N7 was obtained by selective bromination reaction with NBS. 7 reacts with c H ,N to form salt to obtain 8,8 is hydrolyzed by heating to obtain 3T
2.3 9m lithium aluminum hydride reduction (10m NABH/A1C1 reduction) ll. ll oxidation (oxidant MnO, KBr/TEMPO, pyridinium chlorochromate, etc.)
2.4 Vitamin B 1 to NaHSO hydrolysis of 12,l2 to CrO /H2SO4 oxidative cleavage of 3 "l,].
2.5 SOCI, acting on l3-acyl chloride 14, then hydrogenation and reduction to 3T
2.6 under the action of ozone, olefin cracking reaction occurs and 3
2.7 bromine acting on 16, l7 was obtained. Ethylene glycol protects the formyl group of l7 from acetal 18. 18 with thioformamide reaction, ring formation of thiazole acetal 19. Hydrolysis of acetal l9 by sulfuric acid to obtain 3
(Data Search ~ CA2008, Volume 148)
Last Update：2024-04-10 22:29:15
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