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US 10,858,326 B2Granted
Oxazoline pseudodimers, pharmaceutical compositions and the use thereof
AssigneePurdue Pharma L.P.
InventorsPaul Blake, Laykea Tafesse
Life of this patent
Estimating the term…
Abstract
The present disclosure is directed to oxazoline mono- and hetero-pseudodimer compounds, such as compounds of Formula (I) or pharmaceutically acceptable salts or solvates thereof: These compounds are useful for treating pain. The present disclosure also relates to pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of Formula (I) or (II) or a pharmaceutically acceptable salt or solvate thereof.
Claims19
A compound of Formula (I)
- or a pharmaceutically acceptable salt or solvate thereof, wherein
- each R1 and each R5 are independently:
- deuterium,
- tritium,
- lower alkyl,
- lower alkoxy,
- lower alkyl substituted by one or more same or different halogens,
- lower alkoxy substituted by one or more same or different halogens,
- halogen,
- phenyl unsubstituted or substituted by one or more same or different halogens,
- phenyloxy,
- benzyl,
- benzyloxy,
- —COO-lower alkyl,
- —O—(CH2)o—O-lower alkyl,
- —NH-cycloalkyl,
- cycloalkyl,
- piperidin-1-yl, or
- tetrahydropyran-4-yloxy;
- X1 and X2 are each independently a bond, —CH(R20)—, —CH(R20)CH(R21)—, —OCH(R20)—, —N(R20)CH(R21)—, —CH2OCH(R20)—, —CH2CH2CH2—, —SCH(R20)—, —S(O)2CH(R20)—, —CH2SCH2—, —CH2N(R20)CH2—, -cycloalkyl-CH2— or —Si(R20)(R21)CH2—, wherein R20 and R21 are each independently hydrogen, lower alkyl, lower alkyl substituted by one or more same or different halogens, or benzyl unsubstituted or substituted by one or more same or different substituents selected from the group consisting of alkoxy and halogen;
- R2 and R6 are each independently hydrogen, phenyl, or lower alkyl;
- R3, R4, R7, and R8 are each independently hydrogen, lower alkyl, lower alkoxy, lower alkyl substituted by one or more same or different halogens, or lower alkoxy substituted by one or more same or different halogens;
- Y1 and Y2 are each independently phenyl, naphthyl, thiophenyl, pyridinyl, cycloalkyl, 1,2,3,4-tetrahydro-naphthalen-2-yl, 2,3-dihydrobenzo[1,4]dioxin-6-yl, benzo[1,3]dioxol-5-yl, pyrimidyl, indanyl, 2,3-dihydroindol-1-yl, or 3,4-dihydro-quinolin-1-yl;
- m and n are each independently 0, 1, 2 or 3;
- and
- o is 1, 2, or 3, and
- wherein the compound of Formula (I) is not
24 more elements
A method of treating pain comprising administering to a subject in need thereof a therapeutically effective amount of a compound of Formula (I)
- or a pharmaceutically acceptable salt thereof, wherein
- each R1 and each R5 are independently:
- deuterium,
- tritium,
- lower alkyl,
- lower alkoxy,
- lower alkyl substituted by one or more same or different halogens,
- lower alkoxy substituted by one or more same or different halogens,
- halogen,
- phenyl unsubstituted or substituted by one or more same or different halogens,
- phenyloxy,
- benzyl,
- benzyloxy,
- —COO-lower alkyl,
- —O—(CH2)o—O-lower alkyl,
- —NH-cycloalkyl,
- cycloalkyl,
- piperidin-1-yl, or
- tetrahydropyran-4-yloxy;
- X1 and X2 are each independently a bond, —CH(R20)—, —CH(R20)CH(R21)—, —OCH(R20)—, —N(R20)CH(R21)—, —CH2OCH(R20)—, —CH2CH2CH2—, —SCH(R20)—, —S(O)2CH(R20)—, —CH2SCH2—, —CH2N(R20)CH2—, -cycloalkyl-CH2— or —Si(R20)(R21)CH2—, wherein R20 and R21 are each independently hydrogen, lower alkyl, lower alkyl substituted by one or more same or different halogens, or benzyl unsubstituted or substituted by one or more same or different substituents selected from the group consisting of alkoxy and halogen;
- R2 and R6 are each independently hydrogen, phenyl, or lower alkyl;
- R3, R4, R7, and R8 are each independently hydrogen, lower alkyl, lower alkoxy, lower alkyl substituted by one or more same or different halogens, or lower alkoxy substituted by one or more same or different halogens;
- Y1 and Y2 are each independently phenyl, naphthyl, thiophenyl, pyridinyl, cycloalkyl, 1,2,3,4-tetrahydro-naphthalen-2-yl, 2,3-dihydrobenzo[1,4]dioxin-6-yl, benzo[1,3]dioxol-5-yl, pyrimidyl, indanyl, 2,3-dihydroindol-1-yl, or 3,4-dihydro-quinolin-1-yl;
- m and n are each independently 0, 1, 2 or 3;
- and
- o is 1, 2, or 3.
23 more elements
A method of activating TAAR1 comprising administering to a subject in need thereof an effective amount of a compound of Formula (I)
- or a pharmaceutically acceptable salt thereof, wherein
- each R1 and each R5 are independently:
- deuterium,
- tritium,
- lower alkyl,
- lower alkoxy,
- lower alkyl substituted by one or more same or different halogens,
- lower alkoxy substituted by one or more same or different halogens,
- halogen,
- phenyl unsubstituted or substituted by one or more same or different halogens,
- phenyloxy,
- benzyl,
- benzyloxy,
- —COO-lower alkyl,
- —O—(CH2)o—O-lower alkyl,
- —NH-cycloalkyl,
- cycloalkyl,
- piperidin-1-yl, or
- tetrahydropyran-4-yloxy;
- X1 and X2 are each independently a bond, —CH(R20)—, —CH(R20)CH(R21)—, —OCH(R20)—, —N(R20)CH(R21) CH2OCH(R20)—, —CH2CH2CH2—, —SCH(R20)—, —S(O)2CH(R20)—, —CH2SCH2—, —CH2N(R20)CH2—, -cycloalkyl-CH2— or —Si(R20)(R21)CH2—, wherein R20 and R21 are each independently hydrogen, lower alkyl, lower alkyl substituted by one or more same or different halogens, or benzyl unsubstituted or substituted by one or more same or different substituents selected from the group consisting of alkoxy and halogen;
- R2 and R6 are each independently hydrogen, phenyl, or lower alkyl;
- R3, R4, R7, and R8 are each independently hydrogen, lower alkyl, lower alkoxy, lower alkyl substituted by one or more same or different halogens, or lower alkoxy substituted by one or more same or different halogens;
- Y1 and Y2 are each independently phenyl, naphthyl, thiophenyl, pyridinyl, cycloalkyl, 1,2,3,4-tetrahydro-naphthalen-2-yl, 2,3-dihydrobenzo[1,4]dioxin-6-yl, benzo[1,3]dioxol-5-yl, pyrimidyl, indanyl, 2,3-dihydroindol-1-yl, or 3,4-dihydro-quinolin-1-yl;
- m and n are each independently 0, 1, 2 or 3;
- and
- o is 1, 2, or 3.
23 more elements
Dependencies are inferred from the claim text.