Cationic steroidal antimicrobial compounds and methods of manufacturing such compounds
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07J-041/00
A61K-031/575
C07C-225/00
C07C-211/00
출원번호
US-0866213
(2015-09-25)
등록번호
US-9434759
(2016-09-06)
발명자
/ 주소
Savage, Paul B.
출원인 / 주소
BRIGHAM YOUNG UNIVERSITY
대리인 / 주소
Workman Nydegger
인용정보
피인용 횟수 :
4인용 특허 :
38
초록▼
Cationic steroidal antimicrobial (CSA) compounds having amide functionality and methods of manufacturing such CSA compounds. The CSA compound can be a compound of Formula (I), Formula (II), Formula (III), or a salt thereof: where R18 has the following structure: —R20—(C═O)—N—R21R22 R20 is omitted or
Cationic steroidal antimicrobial (CSA) compounds having amide functionality and methods of manufacturing such CSA compounds. The CSA compound can be a compound of Formula (I), Formula (II), Formula (III), or a salt thereof: where R18 has the following structure: —R20—(C═O)—N—R21R22 R20 is omitted or substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl, andR21 and R22 are independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, or substituted or unsubstituted aryl, provided that at least one of R21 and R22 is not hydrogen.
대표청구항▼
1. A cationic steroidal antimicrobial (CSA) compound of Formula (III), or salt thereof: wherein, R3, R7, and R12 are independently selected from the group consisting of aminoalkyloxy, aminoalkylcarboxy, alkylaminoalkyl, alkoxycarbonylalkyl, alkylcarbonylalkyl, di(alkyl)aminoalkyl, alkylcarboxyalkyl
1. A cationic steroidal antimicrobial (CSA) compound of Formula (III), or salt thereof: wherein, R3, R7, and R12 are independently selected from the group consisting of aminoalkyloxy, aminoalkylcarboxy, alkylaminoalkyl, alkoxycarbonylalkyl, alkylcarbonylalkyl, di(alkyl)aminoalkyl, alkylcarboxyalkyl, aminoalkylaminocarbonyl, aminoalkylcarboxamido, guanidinoalkyloxy, guanidinoalkylcarboxy, quaternary ammonium alkylcarboxy, and hydroxyalkyl,R18 has the following structure: —R20—(C═O)—N—R21R22 R20 is a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C1-C10 alkenyl, a substituted or unsubstituted C1-C10 alkynyl, or a substituted or unsubstituted C6 or C10 aryl, andR21 and R22 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C6 or C10 aryl, substituted or unsubstituted 5 to 10 membered heteroaryl, substituted or unsubstituted 5 to 10 membered heterocyclyl, substituted or unsubstituted C7-C13 aralkyl, substituted or unsubstituted (5 to 10 membered heteroaryl)-C1-C6 alkyl, substituted or unsubstituted C3-C10 carbocyclyl, substituted or unsubstituted C4-C10 (carbocyclyl)alkyl, substituted or unsubstituted (5 to 10 membered heterocyclyl)-C1-C6 alkyl, substituted or unsubstituted substituted amido, and amine protecting group, provided that at least one of R21 and R22 is not hydrogen. 2. The CSA compound of claim 1, wherein R3, R7, and R12 are independently selected from the group consisting of unsubstituted (C1-C6) hydroxyalkyl, unsubstituted (C1-C16) alkylamino-(C1-C5)alkyl, unsubstituted (C1-C5) aminoalkyloxy, unsubstituted (C1-C5) aminoalkylcarboxy, unsubstituted (C1-C5) aminoalkylaminocarbonyl, unsubstituted (C1-C5) aminoalkylcarboxamido, unsubstituted di(C1-C5 alkyl)amino-(C1-C5) alkyl, unsubstituted (C1-C5) guanidinoalkyloxy, unsubstituted (C1-C16) quaternary ammonium alkylcarboxy, and unsubstituted (C1-C16) guanidinoalkylcarboxy. 3. The CSA compound of claim 1, wherein R3, R7, and R12 are independently selected from the group consisting of aminoalkyloxy, aminoalkylcarboxy, alkoxycarbonylalkyl, aminoalkylaminocarbonyl, aminoalkylcarboxamido, guanidinoalkyloxy, guanidinoalkylcarboxy, and quaternary ammonium alkylcarboxy. 4. The CSA compound of claim 1, wherein R3, R7, and R12 are each one of aminoalkyloxy or aminoalkylcarboxy. 5. The CSA compound of claim 1, wherein R3, R7, and R12 are independently selected from the group consisting of amino-C3-alkyloxy; amino-C3-alkyl-carboxy; C8-alkylamino-C5-alkyl; C8-alkoxy-carbonyl-C4-alkyl; C8-alkyl-carbonyl-C4-alkyl; di-(C5-alkyl)amino-C5-alkyl; C13-alkylamino-C5-alkyl; C6-alkoxy-carbonyl-C4-alkyl; C6-alkyl-carboxy-C4-alkyl; and C16-alkylamino-C5-alkyl. 6. A pharmaceutical composition comprising the CSA compound of claim 1 and a pharmaceutically acceptable excipient. 7. A cationic steroidal antimicrobial (CSA) compound selected from the group consisting of: and salts thereof. 8. The CSA compound of claim 7, wherein the CSA compound is or salt thereof. 9. The CSA compound of claim 7, wherein the CSA compound comprises a salt selected from the group consisting of: (1) salts obtained by reacting a CSA compound with an inorganic acid, a hydrohalic acid, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and/or phosphoric acid; (2) salts obtained by reacting a CSA compound with an organic acid, an aliphatic or aromatic carboxylic or sulfonic acid, formic acid, acetic acid, propionic acid, glycolic acid, pyruvic acid, malonic acid, maleic acid, fumaric acid, trifluoroacetic acid, benzoic acid, cinnamic acid, mandelic acid, succinic acid, lactic acid, malic acid, tartaric acid, citric acid, ascorbic acid, nicotinic acid, methanesulfonic acid, ethanesulfonic acid, p-toluensulfonic acid, salicylic acid, stearic acid, muconic acid, butyric acid, phenylacetic acid, phenylbutyric acid, valproic acid, 1,2-ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 2-naphthalenesulfonic acid, and/or naphthalenesulfonic acid; (3) salts obtained by reacting a CSA compound with a base to form an ammonium salt, an alkali metal salt, a lithium, sodium or a potassium salt, an alkaline earth metal salt, a calcium, magnesium and/or aluminum salt; (4) salts of organic bases, dicyclohexylamine, N-methyl-D-glucamine, tris(hydroxymethyl)methylamine, C1-C7 alkylamine, cyclohexylamine, dicyclohexylamine, triethanolamine, ethylenediamine, ethanolamine, diethanolamine, triethanolamine, and/or tromethamine, and salts with amino acids such as arginine and lysine; and (5) salts of an inorganic base, aluminum hydroxide, calcium hydroxide, potassium hydroxide, sodium carbonate, and/or sodium hydroxide. 10. The CSA compound of claim 7, wherein the CSA compound comprises a salt selected from the group consisting of hydrochloride salts, mono-hydrochloride salts, di-hydrochloride salts, tri-hydrochloride salts, tetra-hydrochloride salts, sulfuric acid addition salts, sulfonic acid addition salts, disulfonic acid addition salts, 1,5-naphthalenedisulfonic acid addition salts, sulfate salts, and bisulfate salts. 11. The CSA compound of claim 1, wherein one of R21 or R22 is hydrogen and one is not hydrogen. 12. An antimicrobial composition comprising the CSA compound of claim 1 and a carrier. 13. The pharmaceutical composition of claim 6, wherein the pharmaceutically acceptable excipient comprises at least one member selected from the group consisting of carriers, solvents, stabilizers, adjuvants, diluents, and combinations thereof. 14. The pharmaceutical composition of claim 6, wherein the pharmaceutical composition is in a dosage form selected from the group consisting of tablets, capsules, solids, emulsions, suspensions, solutions, liquids, powders, syrups, creams, ointments, troches, lozenges, granules, and elixirs. 15. The CSA compound of claim 7, wherein the CSA compound is 16. A pharmaceutical composition comprising the CSA compound of claim 7 and a pharmaceutically acceptable excipient. 17. An antimicrobial composition comprising the CSA compound of claim 7 and a carrier. 18. A cationic steroidal antimicrobial (CSA) compound of Formula (III), or salt thereof: wherein, R3, R7, and R12 are independently selected from the group consisting of aminoalkyloxy, aminoalkylcarboxy, aminoalkylaminocarbonyl, aminoalkylcarboxamido, and quaternary ammonium alkylcarboxy,R18 has the following structure: —R20—(C═O)—N—R21R22 R20 is a C4 alkyl, andR21 and R22 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C6 or C10 aryl, substituted or unsubstituted 5 to 10 membered heteroaryl, substituted or unsubstituted 5 to 10 membered heterocyclyl, substituted or unsubstituted C7-C13 aralkyl, substituted or unsubstituted (5 to 10 membered heteroaryl)-C1-C6 alkyl, substituted or unsubstituted C3-C10 carbocyclyl, substituted or unsubstituted C4-C10 (carbocyclyl)alkyl, substituted or unsubstituted (5 to 10 membered heterocyclyl)-C1-C6 alkyl, provided that at least one of R21 and R22 is not hydrogen. 19. The CSA compound of claim 18, wherein R3, R7, and R12 are each one of aminoalkyloxy or aminoalkylcarboxy. 20. The CSA compound of claim 18, wherein R3, R7, and R12 are each one of amino-C3-alkyloxy or amino-C3-alkyl-carboxy.
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