Weight Loss Treatment
OwnerDaniel A. Erlanson, Stig Hanseninventors
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Abstract
The present invention relates to the use of 2-phenyl-1,2-benzisoselenazol-3(2H)-one and other selenium-containing compounds for weight loss.
Claims26
A weight loss method, comprising administering to a subject in need of weight loss an effective amount of 2-phenyl-1,2-benzisoselenazol-3(2H)-one to induce weight loss or to prevent further weight gain in said subject.
An obesity treatment method, comprising administering to an obese subject an effective amount of 2-phenyl-1,2-benzisoselenazol-3(2H)-one to induce weight loss in said subject.
A weight loss method, comprising administering to a subject in need of weight loss an effective amount of a compound of Formula (I):
- wherein the Se bonded to —N—R1 above is optionally oxidized;
- X is C═O or SO2;
- A is a 5-6-membered aryl, or heteroaryl group, which heteroaryl group has 1 or 2 ring atoms selected from the group consisting of N and S;
- in each instance optionally substituted with 1-3 substituents independently selected from the group consisting of straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —OC1-6, —NO2, —OH, halo, —CN, and —CHO;
- and
- R1 is
- i) straight or branched —C1-6alkyl, straight or branched —C1-6alkenyl, straight or branched —C1-6alkynyl, —OC1-6, —C1-3—O—C1-3, —OH, —C1-6NRa1Rb1, —C1-6(═S)NRa1Rb1, —C1-6(═O)NRa1Rb1, —NRa1Rb1, —CN, —OCN, —C1-6(═O), —C1-6(═O)OH, or —C1-6(═O)OC1-6, or
- ii) cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —C1-6alkylcycloalkyl, —C1-6alkylheterocycloalkyl, —C1-6alkylaryl, or —C1-6alkylheteroaryl (wherein for any ring hetero means 1-2 of N, S, O);
- in each instance optionally substituted with 1-4 substituents independently selected from straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —OC1-6, —NO2, —OH, ═O, halo, —CF3, —NRa1Rb1, —CN, —OCN, —C1-6(═O), —C1-6(═O)OH, —C1-6(═O)OC1-6, —OC1-6(═O)NRa1Rb1, —C1-6(O)NRa1Rb1, —SC1-6alkyl, —SH, —SO2NRa1Rb1, and —N3;
- wherein, in each instance Ra1 and Rb1 are independently H or substituted or unsubstituted C1-6alkyl, or one of Ra1 and Rb1 is H and the other is C1-6(═O)OH, C1-6C(═O)OC1-6, or —C(═N)N—NO2, substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl;
- or an isomer or salt thereof.
A weight loss method comprising administering to a subject in need of weight loss an effective amount of a compound of Formula (II):
- wherein each instance of A is independently
- a 5-6-membered aryl, or heteroaryl group, which heteroaryl group has 1 or 2 ring atoms selected from the group consisting of N and S;
- in each instance optionally substituted with 1-3 substituents independently selected from the group consisting of straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —OC1-6, —NO2, —OH, halo, —CN, and —CHO;
- and
- L is phenyl, biphenyl, phenyl-CH2-phenyl, phenyl-CH2, CH2-phenyl-, phenyl-SO2, SO2-phenyl, -(phenyl)Se—Se(phenyl)- or is straight or branched —C1-6alkyl-, wherein up to three carbon atoms in the alkyl group may be replaced with NRa2, O or S, wherein Ra2 is H or is —C1-6alkyl;
- or an isomer or salt thereof.
A weight loss method comprising administering to a subject in need of weight loss an effective amount of a compound of Formula (III):
- wherein each instance of B is independently an 5-6-membered aryl or heteroaryl group, the heteroaryl group having 1 or 2 heteroatoms selected from the group consisting of N, and S, and wherein the aryl or heteroaryl group may also have a phenyl ring fused thereto and
- in each instance B is optionally substituted with 1-3 substituents independently selected from the group consisting of straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —OC1-6, —NO2, —OH, halo, —CN, and —C1-6(═O)NRa3Rb3;
- wherein in each instance Ra3 and Rb3 are independently H or substituted or unsubstituted C1-6alkyl, substituted or unsubstituted —C(═O)C1-6, or substituted or unsubstituted —C(═O)NRc3Rd3, wherein one of Ra3 and Rb3 is hydrogen, and the other is substituted or unsubstituted phenyl;
- or wherein Ra3 and Rb3 taken together with the nitrogen to which they are attached form a substituted or unsubstituted heterocycloalkyl group;
- wherein Rc3 and Rd3 are independently H or C1-6alkyl;
- and
- each instance of R2 and R3 is hydrogen or —OH, or one or both instances of R2 and R3 attached to the same carbon taken together are ═O;
- each instance of R4 is independently:
- i) straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —OC1-6, —C1-3—O—C1-3, —OH, —C1-6NRa4Rb4, —C1-6(═S)NRa4Rb4, —C1-6(═O)NRa4Rb4, —NRa4Rb4, —CN, —OCN, —C1-6(═O), —C1-6(═O)OH, or —C1-6(═O)OC1-6, or
- ii) cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —C1-6alkylcycloalkyl, —C1-6alkylheterocycloalkyl, —C1-6alkylaryl, or —C1-6alkylheteroaryl (wherein for any ring hetero means 1-2 of N, S, O);
- in each instance optionally substituted with 1-4 substituents independently selected from straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —OC1-6, —NO2, —OH, ═O, halo, —CF3, —NRa4Rb4, —CN, —OCN, —C1-6(═O), —C1-6(═O)OH, —C1-6(═O)OC1-6, —OC1-6(═O)NRa4Rb4, —C1-6(═O)NRa4Rb4, —C(═O)NHC(═O)C1-6alkyl, —C(═O)NHC(═O)NRa4Rb4, —SC1-6alkyl, —SH, —SO2NRa4Rb4, and —N3;
- wherein, in each instance Ra4 and Rb4 are independently H or C1-6alkyl, substituted or unsubstituted, or one of Ra4 and Rb4 is H and the other is substituted or unsubstituted cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkylheteroaryl, —C(═O)heterocycloalkyl, —C1-6(═O)OH, —C1-6C(═O)OC1-6, or —C(═N)N—NO2;
- or an isomer or salt thereof.
A weight loss method comprising administering to a subject in need of weight loss an effective amount of a compound of Formula (IV):
- wherein
- A is a 5-6-membered aryl or heteroaryl group, which heteroaryl group has 1 or 2 ring atoms selected from the group consisting of N and S;
- in each instance optionally substituted with 1-3 substituents independently selected from the group consisting of straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —OC1-6, —NO2, —OH, halo, —CN, and —CHO;
- R1 is
- i) straight or branched —C1-6alkyl, straight or branched —C1-6alkenyl, straight or branched —C1-6alkynyl, —OC1-6, —C1-3—O—C1-3, —OH, —C1-6NRa1Rb1, —C1-6(═S)NRa1Rb1, —C1-6(O)NRa1Rb1, —NRa1Rb1, —CN, —OCN, —C1-6(═O), —C1-6(═O)OH, or —C1-6(═O)OC1-6, or
- ii) cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —C1-6alkylcycloalkyl, —C1-6alkylheterocycloalkyl, —C1-6alkylaryl, or —C1-6alkylheteroaryl (wherein for any ring hetero means 1-2 of N, S, O);
- in each instance optionally substituted with 1-4 substituents independently selected from straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —OC1-6, —NO2, —OH, ═O, halo, —CF3, —NRa1Rb1, —CN, —OCN, —C1-6(═O), —C1-6(═O)OH, —C1-6(═O)OC1-6, —OC1-6(═O)NRa1Rb1, —C1-6(═O)NRa1Rb1, —SC1-6alkyl, —SH, —SO2NRa1Rb1, and —N3;
- wherein, in each instance Ra1 and Rb1 are independently H or substituted or unsubstituted C1-6alkyl, or one of Ra1 and Rb1 is H and the other is C1-6 (═O)OH, C1-6C(═O)OC1-6, or —C(═N)N—NO2, substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl;
- and
- R5 is:
- i) straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, straight or branched —C2-6alkynyl, —C1-3—O—C1-3, —C1-6NRa5Rb5, —C1-6(═O)NRa5Rb5, —NRa5Rb5, —C1-6(═O), —C1-6(═O)OH, or —C1-6(═O)OC1-6, or
- ii) cycloalkyl, heterocycloalkyl, aryl, heteroaryl, —C1-6alkylcycloalkyl, —C1-6alkylheterocycloalkyl, —C1-6alkylaryl, or —C1-6alkylheteroaryl (wherein for any ring hetero means 1 of N, O);
- in each instance optionally substituted with 1-2 substituents independently selected from
- straight or branched —C1-6alkyl, halo, —C1-6(═O)OH, and —C1-6(═O)OC1-6;
- wherein, in each instance Ra5 and Rb5 are independently H or substituted or unsubstituted C1-6alkyl, or —NRa5Rb5 is —NH(phenyl), which phenyl is substituted or unsubstituted;
- or an isomer or salt thereof.
A weight loss method comprising administering to a subject in need of weight loss an effective amount of a compound of Formula (V):
- wherein Ar is an aryl or heteroaryl group, which heteroaryl group has 1 ring atom selected from the group consisting of N, S, and O;
- in each instance optionally substituted with 1-2 substituents independently selected from the group consisting of straight or branched —C1-6alkyl, —OC1-6, halo, —CN, —OCN, —C1-6(═O), —C1-6(═O)OH, —C1-6(═O)OC1-6, and —OC1-6(═O);
- or an isomer or salt thereof.
A weight loss method comprising administering to a subject in need of weight loss an effective amount of a compound of Formula (VI):
- wherein each R6 is independently selected from the group consisting of straight or branched —C1-6alkyl, straight or branched —C2-6alkenyl, halo, —CF3, —NO2, —CN, —C1-6NRa6Rb6, —NRa6Rb6, —OH, —OC1-6, —OC1-6(═O) and phenyl,
- wherein in each instance Ra6 and Rb6 are independently H, substituted or unsubstituted C1-6alkyl;
- substituted or unsubstituted —C(═O)C1-6, or substituted or unsubstituted —C(═O)NRc6Rd6, or wherein one of Ra6 and Rb6 is hydrogen, and the other is substituted or unsubstituted phenyl, or wherein Ra6 and Rb6 taken together with the nitrogen to which they are attached form a substituted or unsubstituted heterocycloalkyl group and wherein Rc6 and Rd6 are independently H or C1-6alkyl;
- or an isomer or salt thereof.
Dependencies are inferred from the claim text.