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US 2001/0012848 A1Published application
Pharmaceutical compounds
AssigneeEli Lilly and Company
InventorsSean Patrick Hollinshead, Philip Floyd Hughes, Jose Serafin Mendoza, Joseph Wendell Wilson, Bret Eugene Huff, Charles Howard Mitch, Michael Alexander Staszak, John Stanley Ward
Life of this patent
Estimating the term…
Abstract
The present invention provides novel indane-like compounds which can be useful for treating psychosis and other conditions associated with the modulation of a muscarinic receptor. The invention provides formulations and methods for using the novel compounds.
Claims41
A compound of the Formula I:
- 23
- R1 is selected from the group consisting of hydrogen, —OR4, —SR5, C1-C3 alkyl, C2-C3 alkenyl, halo, —CN, S(O)m2, COR4b′, and —OC(O)—R15;
- m2 is from 0 to 2;
- R2 is selected from the group consisting of C1-C10 alkyl, substituted C1-C10 alkyl, C2-C10 alkenyl, substituted C2-C10 alkenyl, C3-C8 cycloalkyl, substituted C3-C8 cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic;
- R4 is hydrogen, C1-C3 alkyl;
- R5 is hydrogen, C1-C3 alkyl;
- R10 is selected from the group consisting of hydrogen, carbonyl, halo, and C1-C3 alkyl;
- R 11 is selected from the group consisting of hydrogen and C1-C3 alkyl;
- R12 is independently selected from the group consisting of hydrogen, C1-C10 alkyl, and aryl;
- R13 is independently selected from the group consisting of hydrogen, C1-C10 alkyl, and aryl;
- or
- R12 and R13 together with the nitrogen to which they are attached form a group of the formula II:
- 24
- II′ wherein the II′ group is a group of Formula II which is unsaturated;
- or
- R11 and R12 together with the nitrogen and carbon to which they are bound can join to form a three to six membered ring;
- R14 is selected from the group consisting of H, halo, C1-C3 alkyl, S(O)m3 and —OR16;
- R15 is C1-C3 alkyl or aryl;
- R16 is C1-C3 alkyl;
- R17 is independently selected from the group consisting of hydrogen, —OR4′,
- —SR5, C1-C3 alkyl, C2-C3 alkenyl, halo, —CN, S(O)m2′, —COR4b, and —OC(O)—R15′;
- R4b and R4b′ are each independently selected from hydrogen and C1-C3 alkyl;
- R15′ is C1-C3 alkyl or aryl;
- m2′ is 0 to 2;
- R4′ is hydrogen, C1-C3 alkyl;
- R5′ is hydrogen, C1-C3 alkyl;
- m2 is 0 to 2;
- X is selected from the group consisting of C, O, S, N, carbonyl, and a bond;
- n′ is 0 to 2;
- m′ is 0 to 2;
- m3 is 0 to 2;
- n is 0 to 3;
- or
- a pharmaceutically acceptable salt or solvate thereof.
31 more elements
A compound of Formula III 25
- R1 is selected from the group consisting of hydrogen, —OR4, —SR5, C1-C3 alkyl, C2-C3 alkenyl, halo, —CN, S(O)m2, —COR4b′, and —OC(O)—R15;
- m2 is from 0 to 2;
- R2 is selected from the group consisting of C1-C10 alkyl, substituted C1-C10 alkyl,
- C2-C10 alkenyl, substituted C2-C10 alkenyl, C3-C8 cycloalkyl, substituted C3-C8 cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic;
- R4 is hydrogen, C1-C3 alkyl;
- R5 is hydrogen, C1-C3 alkyl;
- R10 is selected from the group consisting of hydrogen, carbonyl, halo, and C1-C3 alkyl;
- R11 is selected from the group consisting of hydrogen and C1-C3 alkyl;
- R12 is independently selected from the group consisting of hydrogen, C1-C10 alkyl, and aryl;
- R13 is independently selected from the group consisting of hydrogen, C1-C10 alkyl, and aryl;
- or
- R12 and R13 together with the nitrogen to which they are attached form a group of the formula II:
- 26
- II′ wherein the II′ group is a group of Formula II which is unsaturated;
- or
- R11 and R12 together with the nitrogen and carbon to which they are bound can join to form a three to six membered ring;
- R14 is selected from the group consisting of H, halo, C1-C3 alkyl, S(O)m3 and —OR16;
- R15 is C1-C3 alkyl or aryl;
- R16 is C1-C3 alkyl;
- R17 is independently selected from the group consisting of hydrogen, —OR4′,
- —SR5′, C1-C3 alkyl, C2-C3 alkenyl, halo, —CN, S(O)m2′, —COR4b, and —OC(O)—R15′;
- R4b and R4b′ are each independently selected from hydrogen and C1-C3 alkyl;
- R15′ is C1-C3 alkyl or aryl;
- m2′ is 0 to 2;
- R4′ is hydrogen, C1-C3 alkyl;
- R5′ is hydrogen, C1-C3 alkyl;
- m2 is 0 to 2;
- X is selected from the group consisting of C, O, S, N, carbonyl, and a bond;
- n′ is 0 to 2;
- m′ is 0 to 2;
- m3 is 0 to 2;
- n is 0 to 3;
- or
- a pharmaceutically acceptable salt or solvate thereof.
31 more elements
A compound of Formula IV 27
- R21 and R22 are selected from H and O;
- R20 is selected from amine protecting groups;
- R1′ selected from the group consisting of —OR4, —SR5, C1-C3 alkyl, C2-C3 alkenyl, halo, —CN, S(O)m2, —COR4b′, and —OC(O)—R15;
- m2 is 0 to 2;
- R4 and R4b′ are each independently selected from hydrogen and C1-C3 alkyl;
- R5 is selected from hydrogen and C1-C3 alkyl;
- R15 is C1-C3 alkyl or aryl;
- or
- a pharmaceutically acceptable salt or solvate thereof.
6 more elements
A compound of the Formula V:
- 28
- E1+ is selected from the group consisting of C1-C10 alkyl, substituted C1-C10 alkyl, C2-C10 alkenyl, substituted C2-C10 alkenyl, C3-C8 cycloalkyl, substituted C3-C8 cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, substituted heterocyclic, and aryl electrophile;
- R11 is selected from the group consisting of hydrogen and C1-C3 alkyl;
- R12 is independently selected from the group consisting of hydrogen, C1-C10 alkyl, and aryl;
- R13 is independently selected from the group consisting of hydrogen, C1-C10 alkyl, and aryl;
- or
- R12 and R13 together with the nitrogen to which they are attached form a group of the formula II:
- 29
- II′ wherein the II′ group is a group of Formula II which is unsaturated;
- or
- R11 and R12 together with the nitrogen and carbon to which they are bound can join to form a three to six membered ring;
- R14 is selected from the group consisting of H, halo, C1-C3 alkyl, S(O)m3 and —OR16;
- R16 is C1-C3 alkyl;
- R17 is independently selected from the group consisting of hydrogen, —OR4′,
- —SR5′, C1-C3 alkyl, C2-C3 alkenyl, halo, —CN, S(O)m2′, —COR4b, and —OC(O)—R15′;
- R4b and R4b′ are each independently selected from hydrogen and C1-C3 alkyl;
- R15′ is C1-C3 alkyl or aryl;
- m2′ is 0 to 2;
- R4′ is hydrogen, C1-C3 alkyl;
- R5′ is hydrogen, C1-C3 alkyl;
- m2 is 0 to 2;
- X is selected from the group consisting of C, O, S, N, carbonyl, and a bond;
- n′ is 0 to 2;
- m′ is 0 to 2;
- m3 is 0 to 2;
- n is 0 to 3;
- or
- a pharmaceutically acceptable salt or solvate thereof.
25 more elements
Dependencies are inferred from the claim text.