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US 2005/0065115 A1Published application
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.
Claims54
A pharmaceutical composition comprising an N,N-dihaloamino acid of the formula (I)
- A-C(R1Ro)R(CH2)n—C(YZ)-X′
- or a derivative thereof;
- wherein A is hydrogen or Hal2N—;
- Hal is halogen selected from the group consisting of chloro, bromo and iodo;
- R is a carbon carbon single bond or a divalent cycloalkylene radical with three to six carbon atoms;
- R1 is hydrogen, lower alkyl or the group —COOH;
- Ro is hydrogen or 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 hydrogen, —COOH, —CONH2, —SO3H, —SO2NH2, —P(═O)(OH)2 or —B(OH)2;
- if R is a divalent cycloalkylene radical n is 0 or an integer up to and including 11, said divalent 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.
13 more elements
A composition with bactericidal, antibacterial, anti-infective, antimicrobial, sporicidal, disinfectant, antifungal and antiviral activity comprising an N,N-dihalo-amino 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, bromo and iodo;
- R1 is hydrogen, lower alkyl or the group —COOH;
- Ro is hydrogen or 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 —COOH, —CONH2, —SO3H or —SO2NH2;
- 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 concentration of the N,N-dihaloamino acid or its derivative between 0.1 to 100 mM and a pH range between about 3 to about 4.8, 3.0 to 4.5, or 3.5 to 4.5, or at about 3.5
13 more elements
A stabilized composition with bactericidal, antibacterial, anti-infective, antimicrobial, sporicidal, disinfectant, antifungal and antiviral activity comprising an N,N-dihalo-amino 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, bromo and iodo;
- R1 is hydrogen, lower alkyl or the group —COOH;
- Ro is hydrogen or 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 —COOH, —CONH2, —SO3H or —SO2NH2;
- 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 concentration of the N,N-dihaloamino acid or its derivative between 0.1 to 50 mM and a pH range between about 2 to about 7, 3 to 6, 3 to 4.8, 3 to 4.5, or 3.5 to 4.5, or at about 3.5
13 more elements
A composition comprising an N,N-dihalo-amino 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, bromo and iodo;
- R1 is hydrogen, lower alkyl or the group —COOH;
- Ro is hydrogen or 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 —COOH, —CONH2, —SO3H or —SO2NH2;
- 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, 3 to 6, 3 to 5, or at about 3.5, and
- said compositions having bactericidal, antibacterial, anti-infective, antimicrobial, sporicidal, disinfectant, antifungal and antiviral activity.
14 more elements
The use of a composition comprising an N,N-dihalo-amino 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, bromo and iodo;
- R1 is hydrogen, lower alkyl or the group —COOH;
- Ro is hydrogen or 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 —COOH, —CONH2, —SO3H or —SO2NH2;
- 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, 3 to 6, 3 to 5, or at about 3.5 in the preparation of a medicament for bactericidal, antibacterial, anti-infective, antimicrobial, sporicidal, disinfectant, antifungal and antiviral use.
13 more elements
A method of preventing or treating an infection caused by a bacterial, a microbial, a sporal, a fungal or a viral activity in a mammal, said method comprising the administration of a bactericidal, antibacterial, anti-infective, antimicrobial, sporicidal, disinfectant, antifungal and antiviral amount of an N,N-dihalo-amino 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, bromo and iodo;
- R1 is hydrogen, lower alkyl or the group —COOH;
- Ro is hydrogen or 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 —COOH, —CONH2, —SO3H or —SO2NH2;
- 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.
12 more elements
A composition with bactericidal, antibacterial, anti-infective, antimicrobial, disinfectant, antifungal, sporicidal and antiviral activity comprising an N,N-dihalo-amino acid of the formula (IV)
- Hal2N—C(R1R2)—(CH2)n—C(YZ)-X (IV)
- or a derivative thereof;
- wherein Hal is halogen selected from the group consisting of chloro, bromo and iodo;
- R1 is hydrogen, lower alkyl or the group —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 —COOH, —CONH2, —SO3H or —SO2NH2;
- 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.
10 more elements
An N,N-dihaloamino acid of the formula (IV)
- Hal2N—C(R1R2)—(CH2)n—C(YZ)-X
- or a derivative thereof;
- wherein
- Hal is halogen selected from the group consisting of chloro, bromo and iodo;
- R1 is hydrogen, lower alkyl or the group —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 —COOH, —CONH2, —SO3H or —SO2NH2;
- 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.
11 more elements
Dependencies are inferred from the claim text.