Derivative of micronomycine and its preparing process and medical application

A technology of micronomycin and derivatives, applied in the field of new aminoglycoside antibiotic derivatives, which can solve the problems of aminoglycoside antibiotics losing activity and hindering interaction

Inactive Publication Date: 2003-02-19
四川抗菌素工业研究所有限公司
View PDF0 Cites 23 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As for the biochemical mechanism of drug resistance of aminoglycoside antibiotics, it is believed that drug-resistant bacteria with R factors use the drug resistance group (R factor) present in the plastid or chromosome as a template to form mRNA, and then use the mRNA as a template, Three types of inactivating enzymes are formed on ribonucleosomes that transfer phosphate, adenylate or acetyl groups from adenosine triphosphate (ATP) or acetyl-CoA to aminoglycoside antibiotic molecules, respectively Some important hydroxyl and amino groups cause changes in the structure of aminoglycoside antibiotic molecules, hindering the interaction between aminoglycoside antibiotic molecules and bacterial ribonucleosomes, thereby inactivating aminoglycoside antibiotics

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Derivative of micronomycine and its preparing process and medical application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: SCO-1 (C 1 -N-methyl-minornomycin) preparation

[0060] Feeding: Formaldehyde / THF 4.5ml

[0061] According to the above-mentioned general operation method A method, 2.9 g of SCO-1 was obtained from 14.1 g of triacetyl minonomycin. [α] D t 124.2°; elemental analysis: C: 52.83 H: 9.01 N: 14.67 (theoretical value: C: 52.72 H: 9.20 N: 14.60). IR (cm-1) 3361, 2936, 1452, 1337 MS (m / e) 477 364 360 314 160143 43 28 HNMR (D 2 O)δ(ppm)5.25(H-1′1H d)5.05(H-1″1H d)4.45(H-2′1H d J 1″-2″ =3.5HZ J 2″-3″ =11.0HZ)3.92(H-3″1H s)2.50(3″-N-CH 3 3HS)2.30(6'-NCH 33H S) 1.97 (4″-C-CH 3 3H S) 1.20 (1-NCH 3 3H S).

Embodiment 2

[0062] Embodiment 2: SCO-2 (C 1 -N-ethyl-micronomycin) preparation

[0063] Feeding: 4.5ml of acetaldehyde / tetrahydrofuran

[0064] According to the above-mentioned general operation method A, 2.5 g of SCO-2 was obtained from 14.2 g of triacetyl minonomycin. [α] D t 115.4°; elemental analysis: C: 53.70 H; 9.40 N: 14.20 (theoretical value: C: 53.77 H: 9.37 N: 14.30). IR (cm-1) 3361 2935 1453 1373 MS (m / e) 491 375 361 346314 289 233 160 143 115 100 43 HNMR (D 2 O)δ(ppm)5.27(H-1′1H d)5.00(H-1″1H d)4.45(H-2″1H d J 1″-2″ =3.5HZ J 2″-3″ =11.0HZ)3.92(H-3″1H s)2.48(3″-N-CH 3 3HS)2.35(6'-NCH 3 3H S) 1.95 (4″-C-CH 3 3H S) 1.30 (1-NCH 2 CH 3 2Hq)1.25(1 NCH 2 CH 3 3Ht).

Embodiment 3

[0065] Embodiment 3: SCO-3 (C 1 -N-isobutyl-micronomycin) preparation

[0066] Feeding: 4ml of isobutyraldehyde / tetrahydrofuran

[0067] According to the above-mentioned general operation method A method, 1.9 g of SCO-3 was obtained from 14.1 g of triacetyl minonomycin. [α] D t 119°; elemental analysis: C: 55.40 H: 9.51 N: 13.49 (theoretical value: C: 55.50 H: 9.63 N: 13.48). IR (cm-1) 3360 2935 1452 1390 1372 MS (m / e) 519 375 347 314 272 233 205 160 143 73 57 44 HNMR (D 2 O)δ(ppm)5.25(H-1′1H d)5.01(H-1″1H d)4.46(H-2″1H d J 1″-2″ =3.5HZ J 2″-3″ =11.0HZ)2.45(3″-NCH 3 3HS)2.32(6'-NCH 3 3H S) 1.96 (4″-C-CH 3 3H S) 1.20 (1-NCH 2 -CH(CH 3 ) 2 2H d)0.90(1-NCH 2 CH(CH 3 ) 2 6H d).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

A series of novel derivatives of micronomycin, its preparing process and the medicines containing them as active component are disclosed. The said derivatives are prepared through alkylating and acylating C1-NH2 of microromycin and chemical reactions. Its advantage is high antibacterial activity.

Description

Technical field: [0001] The present invention relates to a kind of novel aminoglycoside antibiotic derivative, relate more specifically to micronomycin C 1 -N-substituted new derivatives, preparation methods of the series of derivatives, and medicines containing the derivatives as active ingredients. Background technique: [0002] Over half a century since the discovery of streptomycin in 1944 and neomycin in 1949, a series of clinically useful aminoglycoside antibiotics have been obtained. The research on aminoglycoside antibiotics began in the 1940s and lasted for more than half a century. Its development has roughly gone through the following stages: streptomycin-neomycin period; kanamycin period; gentamicin (Tobramycin The period of semi-synthetic aminoglycoside antibiotic derivatives (among them, the structurally modified derivatives mainly use kanamycin and gentamicin as the mother nucleus). The emergence of these derivatives has overcome and partly overcome the clin...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/7036A61P31/04C07H15/234
Inventor 刘家健刘敦茀赵经伟
Owner 四川抗菌素工业研究所有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap