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US 2010/0076029 A1Published application
Compounds Which Selectively Modulate The CB2 Receptor
AssigneeBoehringer Ingelheim International GmbH
InventorsAlessandra BARTOLOZZI, Eugene Richard HICKEY, Doris RIETHER, Lifen WU, Renee M. ZINDELL, Stephen Peter EAST, Monika ERMANN
Life of this patent
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Abstract
Compounds of formula (I) are disclosed. Compounds according to the invention bind to and are agonists, antagonists or inverse agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.
Claims12
A compound of the formula (I)
- wherein:
- Het is a 5-membered heteroaryl ring optionally substituted by C1-5 alkyl;
- R1 is C1-10 alkyl, C1-10 alkoxy, C3-10 cycloalkyl, 3-10 membered saturated heterocyclic ring, 5-10 membered mono or bicyclic heteroaryl ring or phenyl each optionally independently substituted with 1-3 substituents chosen from C1-8 alkyl, C1-4 alkoxy, C3-10 cycloalkyl, C3-10 cycloalkylC1-5 alkyl, C1-4 alkylsulfonyl, C1-4 acyl, oxo, cyano, phenyl, hydroxyl and halogen;
- R2 and R3 are C1-C4 alkyl or hydrogen with the proviso that both R2 and R3 cannot be hydrogen;
- or R2 and R3 together with the carbon atom to which they are attached form a 3- to 6-membered cycloalkyl or heterocyclic ring;
- R4 is hydrogen or methyl;
- R5 is chosen from
- or R5 is a 3-10 membered saturated heterocyclic ring optionally substituted with 1-3 C1-4 alkyl;
- m is 0, 1, 2 or 3;
- each R6 is independently hydrogen, C1-6 alkyl, 3-10 membered saturated heterocyclic ring, aryl, benzyl or —(CH2)1-3—O—(CH2)0-1—X wherein X is aryl or CH3 each heterocyclic, benzyl or aryl ring is optionally substituted by one or more C1-4 alkyl, C1-4 alkoxy or halogen;
- wherein R7 and R8 are each independently hydrogen or C1-4 alkyl with the proviso that both R7 and R8 cannot be hydrogen, and wherein R7 and R8 optionally can cyclize to form a C3-7 cycloalkyl ring;
- R9 is C1-4 alkyl which replaces a methylene hydrogen on —(CH2)n— or is absent;
- n is 0, 1 or 2;
- wherein any carbon atom on the formula (I) or any R substituent listed above is optionally partially or fully halogenated where possible;
- or a pharmaceutically acceptable salt thereof
12 more elements
A compound of the formula (II)
- wherein
- of the formula (I) is chosen from column Al1-A11 in Table I, and
- of the formula (I) is chosen from column B1-B36 in Table I,
- TABLE I
- A1
- A2
- A3
- A4
- A5
- A6
- A7
- A8
- A9
- A10
- A11
- B1
- B2
- B3
- B4
- B5
- B6
- B7
- B8
- B9
- B10
- B11
- B12
- B13
- B14
- B15
- B16
- B17
- B18
- B19
- B20
- B21
- B22
- B23
- B24
- B25
- B26
- B27
- B28
- B29
- B30
- B30
- B31
- B32
- B33
- B34
- B35
- B36
- or a pharmaceutically acceptable salt thereof.
50 more elements
A compound chosen from
- or a pharmaceutically acceptable salt thereof.
A compound chosen from
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.