IP Library › Granted Patent US 8,889,670

Granted Patent B2

US 8,889,670 · App. 13/147,432 · Granted Nov 18, 2014

Heterocyclic compounds which modulate the CB2 receptor

Inventors: Alessandra Bartolozzi (Norwalk, CT); Angela Berry (Gaylordsville, CT); Pier Francesco Cirillo (Woodbury, CT); Eugene Richard Hickey (Danbury, CT); Doris Riether (Biberach an der Riss, DE); Lifen Wu (New Milford, CT); Renee M. Zindell (New Milford, CT)

Assignee: Boehringer Ingelheim International GmbH

C07D413/12 C07D211/60 C07D401/12 C07D405/04 C07D417/12 C07D417/14

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Quick Facts

Patent No.: US 8,889,670
App. No.: 13/147,432
Granted: Nov 18, 2014
Kind: B2

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USPTO Patent Center↗ Full Patent PDF↗

Abstract

Compounds which modulate the CB2 receptor are disclosed. Compounds according to the invention bind to and are agonists of the CB2 receptor, and are useful for treating inflammation. Those compounds which are agonists are additionally useful for treating pain.

Claims (345)

1. A compound of the formula (IIA)

wherein

Ar 1 is chosen from phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrothiopyran-1,1-dioxide, tetrahydrothiofuranyl, tetrahydrothiofuran-1,1-dioxide, thiomorpholinyl, 1-oxo-1λ 4 -thiomorpholinyl, 1,1-dioxo-1λ 6 -thiomorpholinyl, pyridinyl, pyrrolidinyl, piperidinyl and piperazinyl, each optionally substituted by 1-3 C 1-6 alkyl, trifluoromethyl, C 1-2 alkoxy, halogen, oxo, —C(O)—C 1-10 alkyl, —S(O) 2 —C 1-3 alkyl or —CO 2 —C 1-4 alkyl;

Ar 2 is chosen from cyclohexyl, benzothiazolyl, benzimidazolyl, oxazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, triazolyl and pyridinyl, each optionally substituted by 1-3 C 1-6 alkyl, trifluoromethyl, cyclopropyl, cyclopentyl, cyclohexyl, phenyl optionally substituted by halogens, CN or halogen;

L 1 is chosen from a bond or C 1-3 alkyl chain wherein each —CH 2 — of said chain is optionally replaced by C(O) or S(O) 2 ;

L 2 is chosen bond or C 2-3 alkyl chain wherein each —CH 2 — of said chain is optionally replaced by S;

R 1 is chosen from hydrogen and oxo (═O);

or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 and wherein:

R 1 is hydrogen.

3. A compound of the formula (IVA)

wherein

of the formula (IVA) is chosen from A1-A53 of Table II, and

of the formula (IVA) is chosen from B1-B39 of Table II,

TABLE II

A10

A11

A12

A13

A14

A15

A16

A17

A18

A19

A20

A21

A22

A23

A24

A25

A26

A27

A28

A29

A30

A31

A32

A33

A34

A35

A36

A37

A38

A39

A40

A41

A42

A43

A44

A45

A46

A47

A48

A49

A50

A51

A52

A53

B10

B11

B12

B13

B14

B15

B16

B17

B18

B19

B20

B21

B22

B23

B24

B25

B26

B27

B28

B29

B30

B31

B32

B33

B34

B35

B36

B37

B38

B39

or a pharmaceutically acceptable salt thereof.

4. The compounds according to claim 3 wherein the stereogenic carbon indicated with an arrow is in the (S) configuration.

5. The compound according to claim 1 wherein:

Ar 2 is isoxazolyl substituted by 1-3 C 1-6 alkyl group.

6. The compound according to claim 1 wherein:

L 1 is a bond or C 1-3 alkyl chain wherein each —CH 2 — of said chain is optionally replaced by C(O);

L 2 is a bond.

7. The compound according to claim 1 wherein:

Ar 1 is chosen from phenyl, tetrahydropyranyl, thiomorpholinyl, 1-Oxo-1λ 4 -thiomorpholinyl, and 1,1-dioxo-1λ 6 -thiomorpholinyl, each optionally substituted chloro;

Ar 2 is isoxazolyl substituted by 1-3 C 1-6 alkyl group;

L 1 is a bond or C 1-2 alkyl chain wherein each —CH 2 — of said chain is optionally replaced by C(O);

L 2 is a bond.

8. The compound according to claim 1 , wherein:

Ar 2 is

9. The compound according to claim 1 wherein:

Ar 1 is chosen from phenyl optionally substituted chloro, tetrahydropyranyl, and 1,1-dioxo-1λ 6 -thiomorpholinyl;

L 1 is a bond or —CH 2 —;

L 2 is a bond.

10. A compound chosen from

1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

1-(Tetrahydro-pyran-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

1-(4-Trifluoromethyl-benzoyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-

3-yl)-amide

1-(4,4-Difluoro-cyclohexanecarbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(R)-1-(4,4-Difluoro-cyclohexanecarbonyl)-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-1-(4,4-Difluoro-cyclohexanecarbonyl)-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(R)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid

(5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(4,4-Difluoro-cyclohexanecarbonyl)-piperidine-2-carboxylic acid (3-tert-

butyl-isoxazol-5-yl)-amide

(S)-3′-Chloro-5′-trifluoromethyl-3,4,5,6-tetrahydro-2H-1,2′-bipyridinyl-2-

carboxylic acid (3-phenyl-1,2,4-thiadiazol-5-yl)-amide

(S)-1-(4,4-Difluoro-cyclohexanecarbonyl)-piperidine-2-carboxylic acid (5-

trifluoromethyl-pyridin-2-yl)-amide

(S)-1-Benzoyl-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(4-Fluoro-benzoyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-

amide

S)-1-Cyclohexanecarbonyl-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-

yl)-amide

(S)-1-Cyclopentanecarbonyl-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-

yl)-amide

S)-1-Cycloheptanecarbonyl-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-

yl)-amide

(S)-1-(3-Chloro-benzoyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-

yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-

butyl-1,3,4-thiadiazol-2-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-

chloro-1H-benzimidazol-2-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (3-sec-

butyl-isoxazol-5-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (3-

isopropyl-isoxazol-5-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (4-

phenyl-thiazol-2-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [2-

(2-chloro-6-fluoro-benzylsulfanyl)-ethyl]-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (3-

cyclohexyl-isoxazol-5-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [3-

(1-methyl-cyclopropyl)-isoxazol-5-yl]-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-

chloro-benzothiazol-2-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (3-

cyclopentyl-isoxazol-5-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (4-tert-butyl-

oxazol-2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (3-phenyl-

1,2,4-thiadiazol-5-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (4-fluoro-3-

trifluoromethyl-phenyl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (3-fluoro-4-

trifluoromethyl-phenyl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (3-isopropyl-

1,2,4-thiadiazol-5-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (4-cyclohexyl-thiazol-

2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-yl)-piperidine-2-carboxylic acid (5-chloro-

benzothiazol-2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-yl)-piperidine-2-carboxylic acid (4-cyclohexyl-thiazol-

2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (3-tert-butyl-

isothiazol-5-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (3-tert-butyl-

1,2,4-thiadiazol-5-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (4-tert-butyl-

thiazol-2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid [4-(3,4-

difluoro-phenyl)-thiazol-2-yl]-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (5-phenyl-

1,2,4-thiadiazol-3-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (4-fluoro-

benzothiazol-2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (4-phenyl-thiazol-

2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (5-

trifluoromethyl-pyridin-2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (6-chloro-

benzothiazol-2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (4-

trifluoromethyl-pyridin-2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (5-chloro-

benzothiazol-2-yl)-amide

(S)-1-(Thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-(Piperidine-1-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-

3-yl)-amide

(S)-1-(1-Oxo-1λ 4 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-1-(4-Acetyl-piperazine-1-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-(4-Propionyl-piperazine-1-carbonyl)-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-2-(5-tert-Butyl-isoxazol-3-ylcarbamoyl)-piperidine-1-carboxylic acid tert-

butyl ester

(S)-5′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-2-carboxylic acid

(5-tert-butyl-isoxazol-3-yl)-amide

(S)-3′-Chloro-5′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-2-

carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(Tetrahydro-pyran-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-[2-(1,1-Dioxo-1λ 6 -thiomorpholin-4-yl)-acetyl]-piperidine-2-carboxylic acid

(5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(4-Chloro-phenyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-

amide

(S)-1-(2-Pyrrolidin-1-yl-acetyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-(2-Morpholin-4-yl-acetyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(2S,4S)-3′-Chloro-4-hydroxy-5′-trifluoromethyl-3,4,5,6-tetrahydro-2H-

[1,2′]bipyridinyl-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(4-cis-Methoxy-cyclohexanecarbonyl)-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-1-(4-Chloro-benzenesulfonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-[2-(4,4-Difluoro-piperidin-1-yl)-acetyl]-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-1-(Tetrahydro-pyran-4-yl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-

3-yl)-amide

(S)-1-(2-Tetrahydro-pyran-4-yl-acetyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-((R)-2-Tetrahydro-furan-2-yl-acetyl)-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (3-

tert-butyl-isoxazol-5-yl)-amide

(S)-1-(4-Chloro-benzoyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-

yl)-amide

(S)-1-(4,4-Difluoro-piperidine-1-carbonyl)-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-1-(1,1-Dioxo-hexahydro-1λ6-thiopyran-4-carbonyl)-piperidine-2-carboxylic

acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(4-Methoxy-benzenesulfonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-[2-(4-Fluoro-piperidin-1-yl)-acetyl]-piperidine-2-carboxylic acid (5-tert-

butyl-isoxazol-3-yl)-amide

(S)-1-[2-(3,3-Difluoro-pyrrolidin-1-yl)-acetyl]-piperidine-2-carboxylic acid (5-

tert-butyl-isoxazol-3-yl)-amide

(S)-2-(5-Ethyl-4-phenyl-thiazol-2-ylcarbamoyl)-piperidine-1-carboxylic acid tert-

butyl ester

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-

ethyl-4-phenyl-thiazol-2-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (5-ethyl-4-

phenyl-thiazol-2-yl)-amide

(S)-1-Isobutyl-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-Cyclopropylmethyl-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-

yl)-amide

(S)-1-Cyclopropyl-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-Cyclopentyl-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(Morpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-tert-butyl-

isoxazol-3-yl)-amide

(S)-1-(benzyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(4-Chloro-benzyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-

amide

(S)-1-(3,4-Difluoro-benzyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-

yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (5-ethyl-1-

phenyl-1H-1,2,4-triazol-3-yl)-amide

(S)-1-(1,1-Dioxo-tetrahydro-1λ 6 -thiophene-3-carbonyl)-piperidine-2-carboxylic

acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-[2-(1,1-Dioxo-tetrahydro-1λ 6 -thiophen-3-yl)-acetyl]-piperidine-2-carboxylic

acid (5-tert-butyl-isoxazol-3-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (1-

ethyl-5-phenyl-1H-1,2,4-triazol-3-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (1-ethyl-5-

phenyl-1H-1,2,4-triazol-3-yl)-amide

(S)-1-(Tetrahydro-pyran-4-ylmethyl)-piperidine-2-carboxylic acid (5-tert-butyl-

1,3,4-thiadiazol-2-yl)-amide

(S)-1-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (3-tert-butyl-

isoxazol-5-yl)-amide

(S)-1-[2-(1,1-Dioxo-tetrahydro-1λ 6 -thiophen-3-yl)-acetyl]-piperidine-2-carboxylic

acid (1-ethyl-5-phenyl-1H-1,2,4-triazol-3-yl)-amide

(S)-1-(2,2,2-Trifluoro-acetyl)-piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-

3-yl)-amide

(S)-2-(5-tert-Butyl-1,3,4-thiadiazol-2-ylcarbamoyl)-piperidine-1-carboxylic acid

tert-butyl ester

(S)-1-Cyclobutyl-piperidine-2-carboxylic acid (5-tert-butyl-1,3,4-thiadiazol-2-yl)-

amide

(S)-1-Cyclopropyl-piperidine-2-carboxylic acid (5-tert-butyl-1,3,4-thiadiazol-2-

yl)-amide

(S)-1-[2-(3,3-Difluoro-pyrrolidin-1-yl)-acetyl]-piperidine-2-carboxylic acid (1-

ethyl-5-phenyl-1H-1,2,4-triazol-3-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [5-

(2-methoxy-1,1-dimethyl-ethyl)-isoxazol-3-yl]-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid

(3-phenyl-1,2,4-thiadiazol-5-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [3-

(4-methoxy-phenyl)-[1,2,4]thiadiazol-5-yl]-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [3-

(4-fluoro-phenyl)-[1,2,4]thiadiazol-5-yl]-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (5-

fluoro-benzothiazol-2-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid

(5,6-difluoro-benzothiazol-2-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (4-

chloro-benzothiazol-2-yl)-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [4-

(4-chloro-phenyl)-thiazol-2-yl]-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [4-

(3,4-difluoro-phenyl)-thiazol-2-yl]-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [4-

(2,4-difluoro-phenyl)-thiazol-2-yl]-amide

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid [4-

(4-fluoro-phenyl)-thiazol-2-yl]-amide and

(S)-1-(1,1-Dioxo-1λ 6 -thiomorpholine-4-carbonyl)-piperidine-2-carboxylic acid (4-

fluoro-benzothiazol-2-yl)-amide

or a pharmaceutically acceptable salt thereof.

11. A pharmaceutical composition comprising a therapeutically effective amount of a compound according to claim 1 , and one or more pharmaceutically acceptable carriers and/or adjuvants.

12. A method of treating pain comprising administering a therapeutically effective amount of a compound according to 1 .

13. The method according to claim 12 wherein the pain is acute pain, visceral pain, neuropathic pain, inflammatory and nociceptive pain, cancer pain and headache.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 24, 2011

From: BARTOLOZZI, ALESSANDRA; BERRY, ANGELA; CIRILLO, PIER FRANCESCO; HICKEY, EUGENE RICHARD; RIETHER, DORIS; WU, LIFEN; ZINDELL, RENEE M.

To: BOEHRINGER INGELHEIM INTERNATIONAL GMBH

Reel/Frame 026796/0496 →

Continuity (2)

Provisional Application 61153333 · Feb 18, 2009

Related Publication 20110312944A1 · Dec 22, 2011