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CN114773414A - Aminoglycoside compound, preparation method and application - Google Patents

Aminoglycoside compound, preparation method and application Download PDF

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Publication number
CN114773414A
CN114773414A CN202210195300.4A CN202210195300A CN114773414A CN 114773414 A CN114773414 A CN 114773414A CN 202210195300 A CN202210195300 A CN 202210195300A CN 114773414 A CN114773414 A CN 114773414A
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Prior art keywords
aminoglycoside
hydrogen
atoms
ring
compound
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Inventor
吴鹏程
张志平
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Wuxi Further Pharmaceutical Co ltd
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Wuxi Further Pharmaceutical Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
    • C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
    • C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
    • C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
    • 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

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
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Abstract

The invention provides an aminoglycoside compound, a preparation method and application thereof, belonging to the field of aminoglycoside compounds, wherein the aminoglycoside compound provided by the invention has a chemical structural formula shown as (I),
Figure RE-DDA0003675731720000011
or a pharmaceutically acceptable salt, an active ester or any one chiral isomer compound thereof; wherein Q1、Q2、Q3Is hydrogen or C1-C6The compound has very low toxic and side effects on the eighth cranial nerve, kidney and other tissues, does not cause serious damage to ears and kidneys after long-term use, and can form a heterocyclic ring with more 4 to 6 ring atomsHas good antibacterial effect on drug-resistant bacteria.

Description

Aminoglycoside compound, preparation method and application
Technical Field
The invention relates to an aminoglycoside compound, in particular to an aminoglycoside compound, a preparation method and application thereof.
Background
Aminoglycoside antibiotics (aminoglycoside antibiotics) are a large group of antibiotics having an aminoglycoside structure, and each of the chemical structures thereof contains a parent nucleus obtained by condensation of an aminocyclitol and an aminosugar. Since the discovery of the first aminoglycoside antibiotic, StreptomyCin, from actinomycete cultures by Waksman, a scientist in the united states in 1944, neomycin (neomyein), kanamycin (kanamyein), gentamicin (gentamicin), and the like, have been discovered in succession. Statistically, about 100 natural aminoglycoside antibiotics have been discovered so far, and the total number of these antibiotics is about thousand, including semisynthetic or derivative varieties, and there are currently over ten kinds of these antibiotics used in clinical medicine.
Aminoglycoside antibiotics have in common chemical properties, biological attributes and antibacterial mechanisms. Because the molecules of the compounds contain a plurality of hydroxyl groups and a plurality of amino groups, the compounds are easy to dissolve in water and are alkaline, and the salts formed by the compounds and inorganic acids or organic acids are generally used clinically. The molecular weight of the antibiotic is between 300-800, most of the antibiotic is aqueous amorphous substance, and the antibiotic has no characteristic melting point. Aminoglycoside antibiotics act in an irreversible manner on ribosomes in the body of bacteria to inhibit the synthesis of bacterial proteins and to disrupt the integrity of the bacterial cell membrane, thereby exerting bactericidal effects.
The aminoglycoside antibiotics have the advantages of good water solubility, stable property, wide antibacterial spectrum, strong antibacterial and bactericidal capacity, synergistic action of the [ zz1] antibiotics in combined use and the like, and are clinically important anti-infective medicaments all the time, in particular to indispensable medicaments for treating gram-negative bacterial infection and tuberculosis. However, aminoglycoside antibiotics have stronger toxic and side effects compared with other antibiotics, and can generate drug-resistant bacteria after long-term and large-scale use, so that the clinical application of the antibiotics is limited to a certain extent.
Research shows that aminoglycoside antibiotics have strong toxic and side effects on the eighth pair of cranial nerves, kidney and other tissues, and can cause serious damage to hearing and kidney after long-term and large-scale use. Meanwhile, bacteria can generate various passivating enzymes (phosphotransferase APH for phosphorylating free hydroxyl, nucleotidyl transferase AAD for glycosidating free hydroxyl, phthalein transferase ACA for acetylating free amino, and the like), so that some active groups in the amino glycoside antibiotics are passivated, and the molecules lose activity to generate drug resistance, thereby affecting the curative effect of the antibiotics.
Therefore, there is an urgent need to develop new aminoglycoside antibiotics with low toxicity to ear and kidney and better antibacterial effect on drug-resistant bacteria.
Disclosure of Invention
The aminoglycoside compound provided by the invention has very low toxic and side effects on cranial nerves, kidney and other tissues, can not cause serious damage to ears and kidneys after long-term use, and can generate a good antibacterial effect on drug-resistant bacteria.
In order to achieve the purpose, the invention adopts the technical scheme that:
an aminoglycoside compound, the chemical structural formula of which is shown as (I),
Figure DEST_PATH_IMAGE001
(Ⅰ)
or a pharmaceutically acceptable salt, an active ester or any one chiral isomer compound thereof;
wherein Q is1Is hydrogen, or has the following structural fragment: the chiral center is in S configuration, R configuration or a mixture thereof;
Figure DEST_PATH_IMAGE002
or
Figure DEST_PATH_IMAGE003
Or
Figure DEST_PATH_IMAGE004
Or
Figure DEST_PATH_IMAGE005
；
Q2 is hydrogen, cycloalkylalkyl unsubstituted or substituted with hydroxy, amino or amino-substituted alkyl, heterocyclylalkyl unsubstituted or substituted with hydroxy, amino or alkyl, -C (= NH) NR4R5、-(CR10R11)pR12、
Figure DEST_PATH_IMAGE006
Or
Figure DEST_PATH_IMAGE007
Wherein m and n are any integer of 0-10 Arabic numerals; p1、P2Is a heteroatom group: oxygen, nitrogen, sulfur, phosphorus, and the like;
wherein the alkane ring has from 3 to 15 carbon atoms; the alkyl group has 1 to 12 carbon atoms; and said heterocyclyl refers to a stable 3-to 18-membered non-aromatic ring radical consisting of 2 to 12 carbon atoms and 1 to 6 nitrogens;
Q3、R1、R2、R3、R4、R5、R10、R11、R12is hydrogen or C1-C6Or R is1And R2Together with the atoms to which they are attached may form a heterocyclic ring having more than 4 to 6 ring atoms, or R2And R3Together with the atoms to which they are attached may form a heterocyclic ring having more than 4 to 6 ring atoms, or R1And R3Together with the atoms to which they are attached may form a carbocyclic ring having more than 4 to 6 ring atoms; wherein said heterocyclic ring is a stable 3-to 18-membered non-aromatic cyclic group consisting of 2 to 12 carbon atoms and 1 to 6 nitrogen atoms;
p is an independent integer from 1 to 5.
The invention provides an aminoglycoside compound, wherein Q3Is hydrogen.
The invention provides aminoglycoside compounds, wherein Q1And Q2Is not hydrogen.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure DEST_PATH_IMAGE008
(ii) a Wherein R is1Is hydrogen; r is2Is hydrogen; r3Is hydrogen.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure DEST_PATH_IMAGE009
Or
Figure DEST_PATH_IMAGE010
。
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 410443DEST_PATH_IMAGE008
；
Wherein R is1Is hydrogen; and R is2And R3Together with the atoms to which they are attached form a heterocyclic ring having from 4 to 6 ring atoms.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure DEST_PATH_IMAGE011
、
Figure DEST_PATH_IMAGE012
、
Figure DEST_PATH_IMAGE013
、
Figure DEST_PATH_IMAGE014
、
Figure DEST_PATH_IMAGE015
Figure DEST_PATH_IMAGE016
、
Figure DEST_PATH_IMAGE017
。
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure DEST_PATH_IMAGE018
Wherein R is3Is hydrogen; and R is1And R2Together with the atoms to which they are attached form a heterocyclic ring having from 4 to 6 ring atoms.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 8521DEST_PATH_IMAGE011
、
Figure DEST_PATH_IMAGE019
、
Figure DEST_PATH_IMAGE020
Or
Figure DEST_PATH_IMAGE021
。
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 5165DEST_PATH_IMAGE008
Wherein R is2Is hydrogen; and R is1And R3Taken together with the atoms to which they are attached form a carbocyclic ring having from 4 to 6 ring atoms.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure DEST_PATH_IMAGE022
、
Figure DEST_PATH_IMAGE023
、
Figure DEST_PATH_IMAGE024
、
Figure DEST_PATH_IMAGE025
、
Figure DEST_PATH_IMAGE026
、
Figure DEST_PATH_IMAGE027
Or
Figure DEST_PATH_IMAGE028
。
Aminoglycosides provided by the inventionA compound of formula (I) wherein Q1Is composed of
Figure DEST_PATH_IMAGE029
Wherein R is2Is hydrogen, and R3Is hydrogen.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure DEST_PATH_IMAGE030
Wherein R is2Is hydrogen, and R3Is hydrogen.
The invention provides an aminoglycoside compound, wherein Q1Is a chiral or achiral compound of
Figure 307577DEST_PATH_IMAGE005
Or
Figure DEST_PATH_IMAGE031
。
The invention provides an aminoglycoside compound, wherein Q2Is- (CR)10R11)pR12。
The invention provides an aminoglycoside compound, wherein P is1、P2Is an oxygen or sulfur atom; q2The substituent is
Figure DEST_PATH_IMAGE032
Or
Figure DEST_PATH_IMAGE033
。
The invention provides aminoglycoside compounds, wherein R10Is hydrogen.
The invention provides an aminoglycoside compound, wherein R11Is hydrogen.
The invention provides an aminoglycoside compound, wherein Q2Is cycloalkylalkyl unsubstituted or substituted with hydroxy, amino or amino-substituted alkyl.
The aminoglycoside compound provided by the inventionA compound of formula (I), wherein Q2Unsubstituted.
The invention provides an aminoglycoside compound, wherein Q2Substituted by hydroxyl or amino.
The invention provides an aminoglycoside compound, wherein Q2Is a heterocyclylalkyl group which is unsubstituted or substituted with a hydroxy, amino, or alkyl group.
The invention provides an aminoglycoside compound, wherein Q2Unsubstituted.
The invention provides an aminoglycoside compound, wherein Q2Substituted by hydroxy or amino.
The invention provides an aminoglycoside compound, wherein Q2Is composed of
Figure 204601DEST_PATH_IMAGE032
Or
Figure 445352DEST_PATH_IMAGE033
。
The invention provides an aminoglycoside compound, wherein Q1Not being hydrogen, Q2Is hydrogen.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 742341DEST_PATH_IMAGE018
；
Wherein R is1Is hydrogen; r is2Is hydrogen; r is3Is hydrogen.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure DEST_PATH_IMAGE034
Or
Figure DEST_PATH_IMAGE035
。
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 848444DEST_PATH_IMAGE008
；
Wherein R is1Is hydrogen; and R is2And R3Together with the atoms to which they are attached form a heterocyclic ring having from 4 to 6 ring atoms.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 383330DEST_PATH_IMAGE012
、
Figure DEST_PATH_IMAGE036
、
Figure 857299DEST_PATH_IMAGE013
、
Figure 641584DEST_PATH_IMAGE014
、
Figure 662630DEST_PATH_IMAGE015
、
Figure 786444DEST_PATH_IMAGE016
、
Figure 264322DEST_PATH_IMAGE017
。
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 739166DEST_PATH_IMAGE018
Wherein R is3Is hydrogen; and R is1And R2Taken together with the atoms to which they are attached form a heterocyclic ring having from 4 to 6 ring atoms.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 563902DEST_PATH_IMAGE011
、
Figure 309267DEST_PATH_IMAGE019
、
Figure 357994DEST_PATH_IMAGE020
Or
Figure 320134DEST_PATH_IMAGE021
。
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 948561DEST_PATH_IMAGE018
Wherein R is2Is hydrogen; and R is1And R3Taken together with the atoms to which they are attached form a carbocyclic ring having from 4 to 6 ring atoms.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 811082DEST_PATH_IMAGE022
、
Figure 233973DEST_PATH_IMAGE023
、
Figure 683409DEST_PATH_IMAGE024
、
Figure 849948DEST_PATH_IMAGE025
、
Figure 304325DEST_PATH_IMAGE026
、
Figure 163697DEST_PATH_IMAGE027
Or
Figure 834849DEST_PATH_IMAGE028
。
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 70659DEST_PATH_IMAGE029
Wherein R is2Is hydrogen and R3 is hydrogen.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 438930DEST_PATH_IMAGE030
Wherein R is2Is hydrogen and R3 is hydrogen.
The invention provides an aminoglycoside compound, wherein Q1Is composed of
Figure 469203DEST_PATH_IMAGE005
。
The invention provides an aminoglycoside compound, wherein Q1Is hydrogen, Q2Is not hydrogen.
The invention provides an aminoglycoside compound, wherein Q2is-C (= NH) NH2。
The aminoglycoside compound provided by the invention comprises the following components,
Q2is composed of
Figure 627652DEST_PATH_IMAGE032
Or
Figure 903037DEST_PATH_IMAGE033
。
The aminoglycoside compound provided by the invention is
Figure DEST_PATH_IMAGE037
。
A pharmaceutical composition comprising a compound of any one of the above, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent or excipient.
Use of an aminoglycoside compound according to any one of the preceding claims or a composition according to the preceding claims for the treatment of a bacterial infection in a mammal.
These and other aspects of the invention will be apparent upon reference to the following detailed description.

Claims (10)

1. An aminoglycoside compound, the chemical structural formula of which is shown as (I),
Figure 981195DEST_PATH_IMAGE001
(Ⅰ)
or a pharmaceutically acceptable salt, an active ester or any one chiral isomer compound thereof;
wherein Q is1Is hydrogen, or has the following structural fragment: the chiral center is S configuration, R configuration or a mixture thereof;
Figure 781661DEST_PATH_IMAGE002
or
Figure 206695DEST_PATH_IMAGE003
Or
Figure 459822DEST_PATH_IMAGE004
Or
Figure 762758DEST_PATH_IMAGE005
；
Q2Is hydrogen, cycloalkyl which is unsubstituted or substituted by hydroxyl, amino or alkyl which is substituted by amino, alkyl, heterocyclylalkyl which is unsubstituted or substituted by hydroxyl, amino or alkyl, -C (= NH) NR4R5、-(CR10R11)pR12、
Figure 401419DEST_PATH_IMAGE006
Or
Figure 748087DEST_PATH_IMAGE007
Wherein m and n are any integer of 0-10 Arabic numerals;
P1、P2is a heteroatom group: oxygen, nitrogen, sulfur, phosphorus, etc.;
wherein the alkane ring has 3 to 15 carbon atoms; the alkyl group has 1 to 12 carbon atoms; and said heterocyclyl refers to a stable 3-to 18-membered non-aromatic ring radical consisting of 2 to 12 carbon atoms and 1 to 6 nitrogen atoms;
Q3、R1、R2、R3、R4、R5、R10、R11、R12is hydrogen or C1-C6Or R is1And R2Together with the atoms to which they are attached may form a heterocyclic ring having more than 4 to 6 ring atoms, or R2And R3Together with the atoms to which they are attached may form a heterocyclic ring having more 4 to 6 ring atoms, or R1R = together with the atoms to which it is attached may form a carbocyclic ring having more 4 to 6 ring atoms; wherein said heterocyclic ring is a stable 3-to 18-membered non-aromatic cyclic group consisting of 2 to 12 carbon atoms and 1 to 6 nitrogen atoms;
p is an independent integer from 1 to 5.
2. Aminoglycosides according to claim 3, characterized in that Q1Is composed of
Figure 973663DEST_PATH_IMAGE002
Wherein R is1、R2、R3Are both hydrogen or one of them is hydrogen and the other two, together with the atoms to which they are attached, form a heterocyclic ring having from 4 to 6 ring atoms.
3. The aminoglycoside of claim 1, wherein P is1、P2Is an oxygen or sulfur atom; q2The substituent is
Figure 63978DEST_PATH_IMAGE008
Or
Figure 822725DEST_PATH_IMAGE009
。
4. The aminoglycoside of claim 3, wherein Q is Q2Is cycloalkylalkyl unsubstituted or substituted with hydroxy, amino or amino-substituted alkyl; q2Unsubstituted or Q2Substituted by hydroxy or amino; q2Is composed of
Figure 340294DEST_PATH_IMAGE008
Or
Figure 53166DEST_PATH_IMAGE009
。
5. The aminoglycoside of claim 10, wherein Q is1Is composed of
Figure 681593DEST_PATH_IMAGE010
、
Figure 560425DEST_PATH_IMAGE011
Or is
Figure 734049DEST_PATH_IMAGE012
、
Figure 183485DEST_PATH_IMAGE013
、
Figure 864871DEST_PATH_IMAGE014
、
Figure 817783DEST_PATH_IMAGE015
、
Figure 427887DEST_PATH_IMAGE016
、
Figure 99040DEST_PATH_IMAGE017
、
Figure 873134DEST_PATH_IMAGE018
Or is
Figure 946132DEST_PATH_IMAGE019
、
Figure 727137DEST_PATH_IMAGE020
、
Figure 151165DEST_PATH_IMAGE021
、
Figure 174354DEST_PATH_IMAGE021
Or is
Figure 101859DEST_PATH_IMAGE022
、
Figure 53765DEST_PATH_IMAGE023
、
Figure 699510DEST_PATH_IMAGE024
、
Figure 526390DEST_PATH_IMAGE025
、
Figure 590292DEST_PATH_IMAGE026
、
Figure 962367DEST_PATH_IMAGE027
、
Figure 344676DEST_PATH_IMAGE028
。
6. The aminoglycoside of claim 10, wherein Q is1Is composed of
Figure 460399DEST_PATH_IMAGE029
Wherein R is2Is hydrogen, and R3Is hydrogen; q1Is composed of
Figure 378808DEST_PATH_IMAGE030
。
7. The aminoglycoside of claim 1, wherein Q is1Is hydrogen, Q2Is not hydrogen; q2is-C (= NH) NH2Q2Is composed of
Figure 921785DEST_PATH_IMAGE008
Or
Figure 525810DEST_PATH_IMAGE031
。
8. The aminoglycoside according to claim 1, wherein said aminoglycoside is
Figure 445225DEST_PATH_IMAGE032
。
9. A pharmaceutical composition comprising a compound according to any one of claims 1 to 15, or a pharmaceutically acceptable salt, substituted active ester group thereof, and a pharmaceutically acceptable carrier, diluent or excipient.
10. Use of an aminoglycoside compound according to any one of claims 1 to 14 or a composition according to claim 16 for the treatment of bacterial or other infections in humans or mammals.
CN202210195300.4A 2022-03-02 2022-03-02 Aminoglycoside compound, preparation method and application Pending CN114773414A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3972930A (en) * 1975-02-18 1976-08-03 Sterling Drug Inc. Aminocyclitol antibiotics
US4053591A (en) * 1976-06-30 1977-10-11 Schering Corporation 5-deoxy-4,6-di-o-(aminoglycosyl)-1,3-diaminocyclitols, methods for their manufacture, method for their use as antibacterial agents and compositions useful therefor
US4412068A (en) * 1981-06-08 1983-10-25 Sterling Drug Inc. Novel compounds of the gentamicin class
CN108003205A (en) * 2017-12-22 2018-05-08 中国医药集团总公司四川抗菌素工业研究所 Aminoglycoside derivatives and its preparation method and application

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3972930A (en) * 1975-02-18 1976-08-03 Sterling Drug Inc. Aminocyclitol antibiotics
US4053591A (en) * 1976-06-30 1977-10-11 Schering Corporation 5-deoxy-4,6-di-o-(aminoglycosyl)-1,3-diaminocyclitols, methods for their manufacture, method for their use as antibacterial agents and compositions useful therefor
US4412068A (en) * 1981-06-08 1983-10-25 Sterling Drug Inc. Novel compounds of the gentamicin class
CN108003205A (en) * 2017-12-22 2018-05-08 中国医药集团总公司四川抗菌素工业研究所 Aminoglycoside derivatives and its preparation method and application

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Application publication date: 20220722