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US 7,253,189 B2Granted
Cannabinoid receptor ligands
AssigneeSchering Corporation
InventorsLing Tong, Lei Chen, Bandarpalle B. Shankar, Joseph A. Kozlowski, Neng-Yang Shih
Life of this patent
Estimating the term…
Abstract
A compound of the formula or a pharmaceutically acceptable salt or solvate thereof, wherein: R1, R2, L1, L2, M1, M2, n, p, q, A, D, X, Y and Z are as described in the specification; pharmaceutical compositions thereof, methods of making said pharmaceutical compositions; and methods of use thereof.
Claims53
A compound represented by the structural Formula (I):
- or a pharmaceutically acceptable salt or solvate thereof, wherein:
- R1 is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, —CF3, substituted or unsubstituted alkoxy, —N(R3)2, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, wherein the term “substituted” means being substituted with (X)t substituent(s);
- R2 is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, —CF3, substituted or unsubstituted alkoxy, —N(R3)2, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, wherein the term “substituted” means being substituted with (X)t substituent(s);
- or
- each R3, which can be the same or different, is independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted heteroarylalkyl, wherein the term “substituted” means being substituted with (X)t substituent(s);
- each X, when present, is independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aminoalkyl-, —NR4R5, halo, —CF3, —OCF2H, —OCF3, —OR6, —C(O)R6, —C(O)OR6, —NR6C(O)R7, —NR6C(O)OR7, —C(O)NR4R5, —NO2, —CN, —S(O)2R6, —S(O)2NR4R5 and —NR4S(O)2R5;
- R4 and R5, which can be the same or different, are each independently selected from the group consisting of H or alkyl, or
- R4 and R5, taken together with N to which they are each attached, form a 4- to 8- membered heterocycloalkyl moiety optionally having an additional heteroatom selected from the group consisting of N, O and S, wherein the additional N heteroatom, when present, or any ring carbon atom of the heterocycloalkyl moiety can be substituted with H or alkyl;
- R6 and R7, which can be the same or different, are each independently selected from the group consisting of H or alkyl;
- L1 is selected from the group consisting of —C(R2)2—, —OC(O)—, —C(O)—, —C(O)O—, —(CH(OR2))—, —S(O)2—, —S(O)—, —S—, —O—, —N(R2)—, —C(O)NH—, —NHC(O)—, —CF2— and —C(═N—OR2)—;
- L2 is selected from the group consisting of a covalent bond, —C(R2)2—, —C(═N—OR2—, —S(O)2—, —S(O)—, —S—, —C(O)—, —O—, —N(R2), —C(O)NH—, —NHC(O)—, —OC(O)—, —C(O)O—,—(CH(OR2))— and —CF2—;
- M1 is an aryl, heteroaryl, cycloalkyl or heterocycloalkyl moiety wherein said aryl, heteroaryl, cycloalkyl or heterocycloalkyl moiety is substituted with D when p is ≧1;
- M2 is an alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl moiety wherein said alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl moiety is substituted with A when q is ≧1;
- m is 1-3;
- n is 0-3 wherein when n>1, each X can be the same or different and is independently selected;
- p is 0-4;
- q is 0-5;
- t is 0-6 wherein when t>1, each X can be the same or different and is independently selected;
- v is 1-3;
- A is an optional substituent on M2, each A being independently selected from the group consisting of —Br, —Cl, —F, —CF3, —OH, —OCF2H, —OCF3, alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, —O-substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —CN, —NO2, —C(O)OR4, —C(O)NR4R5, —NR4C(O)R5, —NR4R5, and —S(O)2R2, wherein the term “substituted” means being substituted with (X)t and wherein when q>1, each A can be the same or different;
- D is an optional substituent on M1, each D being independently selected from the group consisting of —Br, —Cl, —F, —CF3, —OH, —OCF2H, —OCF3, alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, —O-substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —CN, —NO2, —C(O)OR4, —C(O)NR4R5, —NR4C(O)R5, —NR4R5, and —S(O)2R2, wherein the term “substituted” means being substituted with (X)n and wherein when p>1, each D can be the same or different;
- Y is selected from the group consisting of a covalent bond, —(CR6R7)m—, —S(O)2—, and —C(O)—;
- and
- Z is selected from the group consisting of a covalent bond, —(CR6R7)v—, —S(O)0-2—, and —C(O)—,
- with the following provisos:
- when L2 is a covalent bond, M2 is directly linked to M1;
- when Y is a covalent bond, R1 is directly linked to the nitrogen atom of —N-Z-R2;
- and
- when Z is a covalent bond, R2 is directly linked to the nitrogen atom of —N—Y—R1.
26 more elements
Dependencies are inferred from the claim text.