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US 7,030,139 B2Granted
Compounds
AssigneeAstraZeneca AB
InventorsYun-Xing Cheng, Miroslaw Tomaszewski, Christopher Walpole, Hua Yang
Life of this patent
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Abstract
Compounds of general formula (I), are disclosed and claimed in the present application, as well as salts and pharmaceutical compositions comprising the novel compounds and their use in therapy, in particular in the management of pain
Claims6
A compound of formula I or a pharmaceutically acceptable salt thereof;
- wherein
- R1 is selected from the group consisting of —(C1–C8)alkyl, —(C2–C8)alkenyl, R42N(C1–C6)alkyl-, R42NC(═O)(C1–C6)alkyl-, R4O(C1–C6)alkyl-, R4OC(═O) (C1–C6)alkyl-, R4C(═O)(C1–C6)alkyl-, R4C(═O)NR4(C1–C6)alkyl-, R42NSO2(C1–C6)alkyl-, R4CSO2NR4(C1–C6)alkyl-, R42NC(═O)NR4(C1–C6)alkyl-, R42NSO2NR4(C1–C6)alkyl-, aryl(C1–C6)alkyl, aroyl(C1–C6)alkyl, (C3–C8)heterocycloalkyl(C1–C6)alkyl, bicyclic heteroaryl (C1–C6)alkyl and bicyclic heteroaroyl(C1–C6)alkyl;
- wherein said —(C2–C8)alkenyl, —(C1–C8)alkyl of R1 are unsubstituted or substituted by one or more moieties independently selected from the group consisting of halogen, cyano, acetoxymethyl, and nitro;
- Ar is an optionally substituted aryl moiety;
- R2 is —(C1–C6)alkyl, unsubstituted or substituted on 1–6 carbons by one or more fluorine substituents, or (C3–C6)cycloalkyl;
- R3 is selected from the group consisting of:
- R4 is a moiety independently selected from the group consisting of —H, —(C1–C6)alkyl, —(C2–C6) alkenyl and —(C2–C6)alkynyl;
- R5 moieties are independently selected from the group consisting of —H, —(C1–C6)alkyl, —(C2–C6)alkenyl and heterocyclyl;
- R6moieties are independently selected from the group consisting of:
- —H, —(C1–C6)alkyl, —(C2–C6)alkenyl, —(C1–C6)alkanoyl, heterocyclyl, heterocyclyl (C1–C3)alkyl, aryl, aryl(C1–C3)alkyl, bicyclic heteroaryl, and bicyclic heteroaryl(C1–C3)alkyl;
- with a proviso that:
- when R3 is (b) or (i), R6 is not —(C1–C6)alkyl;
- when R3 is (j), —R5 are not both —H;
- R5 and R6 may combine to form a 5–7 membered heterocycle;
- X is selected from the group consisting of —C(R5)2—, —NR5—, C(═O )—, —CH2—CH2—, —CH═CH—, —O—, —C(R)(R′)—, and —S(O)n—(where n=0, 1 or 2), where R and R′=(C1–C6)alkyl, OR″, or II, and R″=H or (C1–C6)alkyl;
- and
- Y is CH;
- and
- wherein if R1 represents R42N(C1–C6)alkyl-, wherein both occurrences of R4 represent —(C1 –C6)alkyl, then R3 is not acetyl, —NH2, or acetamido.
16 more elements
A compound formula I,
- wherein:
- R1 is selected from the group consisting of cyclopropylmethyl, ethyl, propyl, allyl, isopentyl, benzyl, methoxyethyl, dimethylaminoethyl, 4-pyridylmethyl, 2-pyridylmethyl, 1-pyrrolylethyl, 1-morpholinoethyl, 5-(2-methylthiazolyl), cyclohexylmethyl, 2-pyrrolidylmethyl, N-methyl-2-pyrrolidylmethyl, 2-piperidylmethyl, N-methyl-2-piperidylmethyl, 3-thienylmethyl, 2-tetrahydrofuranylmethyl, (2-nitrothiophene-5-yl)methyl, (1-methyl-1H-imidazole-2-yl)methyl, (5-(acetoxymethyl)-2-furanyl)methyl, (2,3-dihydro -1H-isoindole-1-yl)methyl, and 5-(2-methylthiazolyl);
- R2 selected from the group consisting of —CH3, —CH2CH3, —CH(CH3)2, and CF3;
- R3 is selected from the group consisting of:
- Y is CH;
- R5 is selected from the group consisting of —H, —CH3, —CH2CH3, —CH═CH2 and —CH2—CH═CH2;
- R6 is selected from the group consisting of —CH3, —CH2CH3, —CH═CH2, —CH2—CH═CH2, —CH2—CH2—CH═CH2, —CH2CH(CH3)2 and 5-methyl-3-isoxazole;
- Ar is a phenyl or six-membered heteroaromatic ring system, either of which may be unsubstituted or substituted by one or more moieties independently selected from the group consisting of (C1–C6)alkyl, halogen, trifluoromethyl, cyano, nitro, hydroxy and —OR4;
- X is selected from the group consisting of —CH2—, —CH2CH2—, —S—, —O—, —CH(C3)—, —C(CH3)2—, —CH(OH)—, —NH—, —N(CH3)—, and —C(═O)—;
- and
- X is positioned on ring Ar in a 1,4 relationship with respect to the —O—R2 group.
8 more elements
Dependencies are inferred from the claim text.