N,N-dihalogenated amino acids and derivatives
AssigneeNovaBay Pharmaceuticals, Inc.
InventorsMansour Bassiri, Ramin Najafi, Lu Wang, Jane Yang
Life of this patent
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Abstract
The present invention relates to active bactericidal, antibacterial, anti-infective, antimicrobial, sporicidal, disinfectant, antifungal and antiviral compounds and compositions and to new uses of these compositions in therapy. This specification also describes methods of use for the new compounds and compositions. The specification further describes methods for preparing these compounds.
Claims30
A composition comprising an N,N-dihaloamino acid of the formula (I))
- A-C(R1Ro)R(CH2)n—C(YZ)—X′ (I)
- or a derivative or a pharmaceutical composition thereof;
- wherein A is Hal2N—;
- Hal is halogen selected from the group consisting of chloro and bromo;
- R is a carbon-carbon single bond or a divalent cycloalkylene radical with three to six carbon atoms;
- R1 is selected from the group consisting of hydrogen, lower alkyl and —COOH;
- Ro is lower alkyl;
- or
- R1 and Ro together with the carbon atom to which they attach form a (C3-C6)cycloalkyl ring;
- n is 0 or an integer from 1 to 13;
- Y is hydrogen, lower alkyl, —NH2 or —NHal2;
- Z is hydrogen or lower alkyl;
- and
- X′ is selected from the group consisting of hydrogen, —SO3H, —SO2NH2, —P(═O)(OH)2 and —B(OH)2;
- if R is a divalent cycloalkylene radical, n is 0 or an integer up to and including 11, said divalent cycloalkylene radical R or divalent radical —(CH2)n— being optionally substituted with —NHal2;
- said derivative being a pharmaceutically acceptable salt, ester with lower alkanols, or lower alkanoyl derivative of the —NH2 group attached to the carbon atom to which the substituent X′ is attached.
A composition comprising an N,N-dihaloamino acid of the formula (II))
- Hal2N—C(R1Ro)—(CH2)n—C(YZ)—X (II)
- or a derivative thereof;
- wherein Hal is halogen selected from the group consisting of chloro and bromo;
- R1 is selected from the group consisting of hydrogen, lower alkyl and —COOH;
- Ro is lower alkyl;
- or
- R1 and Ro together with the carbon atom to which they attach form a (C3-C6)cycloalkyl ring;
- n is 0 or an integer from 1 to 3;
- Y is hydrogen, lower alkyl or —NH2;
- Z is hydrogen or lower alkyl;
- and
- X is selected from the group consisting of —SO3H, —SO2NH2, —P(═O)(OH)2 and —B(OH)2;
- said derivative being selected from the group consisting of pharmaceutically acceptable salts, esters with lower alkanols, and lower alkanoyl derivatives of the —NH2 group attached to the carbon atom to which the substituent X is attached;
- and
- a pharmaceutically acceptable carrier;
- said composition having a pH range between about 2 to about 7.
A method of treating an infection caused by a bacterial, a microbial, a fungal or a viral activity in a mammal, said method comprising the administration a bactericidal, antibacterial, anti-infective, antimicrobial, disinfectant, antifungal and antiviral amount of an N,N-dihaloamino acid of the formula (II):
- Hal2N—C(R1Ro)—(CH2)n—C(YZ)—X (II)
- or a derivative thereof;
- wherein Hal is halogen selected from the group consisting of chloro and bromo;
- R1 is selected from the group consisting of hydrogen, lower alkyl and —COOH;
- Ro is lower alkyl;
- or
- R1 and Ro together with the carbon atom to which they attach form a (C3-C6)cycloalkyl ring;
- n is 0 or an integer from 1 to 3;
- Y is hydrogen, lower alkyl or —NH2;
- Z is hydrogen or lower alkyl;
- and
- X is selected from the group consisting of —SO3H or —SO2NH2, —P(═O)(OH)2 and —B(OH)2;
- said derivative being selected from the group consisting of pharmaceutically acceptable salts, esters with lower alkanols, and lower alkanoyl derivatives of the —NH2 group attached to the carbon atom to which the substituent X is attached;
- and
- a pharmaceutically acceptable carrier.
An N,N-dihaloamino acid of the formula (IV)
- Hal2N—C(R1R2)—(CH2)n—C(YZ)—X (IV)
- or a derivative thereof or a pharmaceutical composition thereof;
- wherein Hal is halogen selected from the group consisting of chloro and bromo;
- R1 is selected from the group consisting of hydrogen, lower alkyl and —COOH;
- R2 is lower alkyl;
- or
- R1 and R2 together with the carbon atom to which they attach form a (C3-C6)cycloalkyl ring;
- n is 0 or an integer from 1 to 3;
- Y is hydrogen, lower alkyl or —NH2;
- Z is hydrogen or lower alkyl;
- and
- X is selected from the group consisting of —SO3H, —SO2NH2, —P(═O)(OH)2 and —B(OH)2;
- said derivative being selected from the group consisting of pharmaceutically acceptable salts, esters with lower alkanols, and lower alkanoyl derivatives of the —NH2 group attached to the carbon atom to which the substituent X is attached.
A compound selected from the group consisting of N,N-dichloro-2-methyl-2-amino-ethanesulfonic acid;
- N,N-dichloro-1-methyl-2-aminoethanesulfonic acid;
- N,N-dichloroamino-trimethylenephosphonic acid;
- N,N-dibromo-2-amino-5-phosphonopantanoic acid;
- N,N-dichloroaminoethylphosphonic acid diesters;
- N,N-dichloro-1-amino-1-methylethanephosphonic acid;
- N,N-dichloro-1-amino-2-methylethanephosphonic acid;
- N,N-dichloro-1-amino-2-methylpropanephosphonic acid;
- N,N-dichloro-leucinephosphonic acid;
- N,N-dichloro-4-amino-4-phosphonobutyric acid;
- (±)N,N-dichloro-2-amino-5-phosphonovaleric acid;
- N,N-dichloro-(+)-2-amino-5-phosphonovaleric acid;
- N,N-dichloro-d,1-2-amino-3-phosphonopropionic acid;
- N,N-dichloro-2-amino-8-phosphonooctanoic acid;
- N,N-dichloro-leucineboronic acid and N,N-dichloro-β-alanineboronic acid, or a derivative thereof, said derivative being selected from the group consisting of pharmaceutically acceptable salts and esters with lower alkanols.
Dependencies are inferred from the claim text.