IP Library › Granted Patent US 8,217,073

Granted Patent B2

US 8,217,073 · App. 12/775,253 · Granted Jul 10, 2012

Pyrrole derivatives as therapeutic compounds

Assignee: Myrexis, Inc.

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Patent No.: US 8,217,073
App. No.: 12/775,253
Granted: Jul 10, 2012
Kind: B2

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Abstract

Novel pyrrole derivatives are disclosed as Aβ 42 -lowering agents for the treatment and prevention of neurodegenerative disorders characterized by the formation or accumulation of amyloid plaques comprising the Aβ 42 peptide.

Claims (121)

1. A compound having a structure according to Formula I:

or a pharmaceutically acceptable salt thereof, wherein:

R 1 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, C 1-6 alkoxy or —(CH) q CO 2 R 10 , wherein R 10 is a hydrogen atom or C 1-6 alkyl, and q is the integer 0, 1, 2, 3, or 4;

R 2 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, C 1-6 alkoxy optionally substituted with 1, 2, or 3 halogens, hydroxyls or amino groups, or phenyl, optionally substituted with 1, 2, 3, 4, or 5 of the same or different substituents chosen from halogen, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, or —(CH) q CO 2 R 10 wherein R 10 is a hydrogen atom or a C 1-6 alkyl and q is the integer 0, 1, 2, 3, or 4;

R 3 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, C 1-6 alkoxy optionally substituted with 1, 2, or 3 halogens, hydroxyls or amino groups, when R 2 is an optionally substituted phenyl; or, when R 2 is not an optionally substituted phenyl, R 3 is —CH 2 CH 2 -phenyl, optionally substituted with 1, 2, 3, 4, or 5 of the same or different substituents chosen from halogen, C 1-6 alkyls optionally substituted with 1, 2, or 3 halogens or hydroxyls, or —(CH) q CO 2 R 10 , wherein R 10 is a hydrogen atom or a C 1-6 alkyl, and q is the integer 0, 1, 2, 3, or 4;

R 4 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, or C 1-6 alkoxy optionally substituted with 1, 2, or 3 halogens, hydroxyls or amino groups;

R 5 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, or C 1-6 alkoxy optionally substituted with 1, 2, or 3 halogens, hydroxyls or amino groups;

one of R 6 and R 7 is -L-C(═O)OH, -L-CH═CHC(═O)OH, -L-C(═)NH 2, -L-C(═)NH(C 1-3 alkyl), -L-C(═O)N(C 1-3 alkyl) 2 , -L-C(═O)NHOH, -L-C(═O)CH 2 NH 2 , -LC(═O)CH 2 OH, L-C(═O)CH 2 SH, -L-C(═O)NHCN, -L-sulfo, -L-(2,6 difluorophenol), -L-phosphono, and -L-tetrazolyl, wherein L is saturated, partially saturated, or unsaturated, and is selected from the group consisting of —(CH 2 ) n —(CH2) n —, —(CH 2 ) n C(═O)(CH 2 ) n —, —(CH 2 ) n NH(CH 2 ) n —, —(CH2) n O(CH 2 ) n —, and —(CH 2 ) n S(CH 2 ) n —, wherein each n is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8, wherein each carbon is optionally substituted with one or more C 1-3 alkyl or C 3-6 cycloalkyl;

while the other of R 6 and R 7 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens, C 1-6 alkoxy optionally substituted with 1, 2, or 3 halogens, hydroxyls, or amino groups;

R 8 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, or C 1-6 alkoxy optionally substituted with 1, 2, or 3 halogens, hydroxyls or amino groups; and

R 9 is independently 0, 1, 2, 3, 4, or 5 substituents, which are independently selected from a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl (optionally substituted with 1, 2, or 3 halogens or hydroxyl groups), C 1-6 haloalkyl, aryl, heteroaryl, heterocycle, —OR, —C(═O)R, —C(═O)OR, —C(═O)NRR, —NRR, —NRC(═O)R, —NRC(═O)OR, —NRC(═O)NRR, —OC(═O)R, —OC(═O)OR, —OC(═O)NRR, —SH, —SR, —SOR, —SO 2 R, —SO 2 NR 2 , —NRSO 2 R, —NR 2 SO 2 R, —Si(R) 3 , or —OP(OR) 3 , wherein each occurrence of R is the same or different and independently a hydrogen atom, C 1-6 alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl or substituted heterocyclealkyl, or wherein any two R groups attached to the same nitrogen atom, taken together with the nitrogen atom to which they are attached, form a heterocyclic ring or a substituted heterocyclic ring.

2. A compound of claim 1 , wherein R 1 , R 5 and R 8 are hydrogen atoms, and the compound has a structure according to Formula II:

or a pharmaceutically acceptable salt thereof, wherein:

R 3 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, C 1-6 alkoxy optionally substituted with 1, 2, or 3 halogens, hydroxyls or amino groups, when R 2 is an optionally substituted phenyl; or, when R 2 is not an optionally substituted phenyl, R 3 is —CH 2 CH 2 —phenyl, optionally substituted with 1, 2, 3, 4, or 5 of the same or different substituents chosen from halogen, C 1-6 alkyls optionally substituted with 1, 2, or 3 halogens or hydroxyls, or —(CH) q CO 2 R 10 , wherein R 10 is a hydrogen atom or a C 1-6 alkyl, and q is the integer 0, 1, 2, 3, or 4;

one of R 6 and R 7 is —(CH 2 ) n CO 2 R 11, —O(CH 2 ) n CO 2 R 11 , or —(CH 2 m O(CH 2 ) p CO 2 R 11 , wherein n is the integer 0, 1, 2, 3, 4, 5, or 6, wherein m is the integer 0, 1, 2, 3, or 4, and p is the integer from 0, 1, 2, 3, 4, 5, or 6, and R 11 is a hydrogen atom or C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens, or

one of R 6 and R 7 is -L-C(═O)OH, -L-CH═CHC(═O)OH, -L-C(═O)NH 2 , -L-C (═O)NH(C 1-3 alkyl), -L-C(═O)N(C 1-3 alkyl) 2 , -L-C(═O)NHOH, -L-C(═O)CH 2 NH 2 , -LC(═O)CH 2 OH, L-C(═O)CH 2 SH, -L-C(═O)NHCN, -L-sulfo, -L-(2,6 difluorophenol), -L-phosphono, and -L-tetrazolyl, wherein L is saturated, partially saturated, or unsaturated, and is selected from the group consisting of —(CH 2 ) n —(CH2) n ——(CH 2 ) n C(═O)(CH 2 ) n —, —(CH 2 ) n NH(CH 2 ) n —, —(CH2) n O(CH 2 ) n —, and —(CH 2 ) n S(CH 2 ) n —, wherein each n is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8, wherein each carbon is optionally substituted with one or more C 1-3 alkyl or C 3-6 cycloalkyl;

R 9 is independently 0, 1, 2, 3, 4, or 5 substituents, which are independently selected from a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl (optionally substituted with 1, 2, or 3 halogens or hydroxyl groups), C 1-6 haloalkyl, aryl, heteroaryl, heterocycle, —OR, —C(═O)R, —C(═O)OR, —C(═O)NRR, —NRR, —NRC(═O)R, —NRC(═O)OR, —NRC(═O)NRR, —OC(═O)OR, —OC(═O)OR, —OC(═O)NRR, —SH, —SR, —SOR, —SO 2 R, —SO 2 NR 2 , —NRSO 2 R, —NR 2 SO 2 R, —Si(R) 3 , or —OP(OR) 3 , wherein each occurrence of R is the same or different and independently a hydrogen atom, C 1-6 alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl or substituted heterocyclealkyl, or wherein any two R groups attached to the same nitrogen atom, taken together with the nitrogen atom to which they are attached, form a heterocyclic ring or a substituted heterocyclic ring.

3. A compound of claim 1 , having a structure according to Formula III:

or a pharmaceutically acceptable salt thereof, wherein:

one of R 6 and R 7 is -L-C(═O)OH, -L-CH═CHC(═O)OH, -L-C(═O)NH 2 , -L-C(═O)NH(C 1-3 alkyl), -L-C(═O)N(C 1-3 alkyl) 2 , -L-C(═O)NHOH, -L-C(═O)CH 2 NH 2 , -LC(═O)CH 2 OH, L-C(═O)CH 2 SH, -L-C(═O)NHCN, -L-sulfo, -L-(2,6 difluorophenol), -L-phosphono, and -L-tetrazolyl, wherein L is saturated, partially saturated, or unsaturated, and is selected from the group consisting of —(CH 2 ) n —(CH2) —, —(CH 2 ) n C(═O)(CH 2 ) n —, —(CH 2 ) n NH(CH 2 ) n —, —(CH2) n O(CH 2 ) n —, and —(CH 2 ) n S(CH 2 ) n —, wherein each n is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8, wherein each carbon is optionally substituted with one or more C 1-3 alkyl or C 3-6 cycloalkyl;

R 8 is a hydrogen atom, halogen hydroxyl C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls or C 1-6 alkoxy optionally substitued with 1, 2, or 3 halogens hydroxyls Or amino groups; and

R 9 and R 12 are independently 0, 1, 2, 3, 4, or 5 substituents, which are independently selected from a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl (optionally substituted with 1, 2, or 3 halogens or hydroxyl groups), C 1-6 haloalkyl, aryl, heteroaryl, heterocycle, —OR, —C(═O)R, —C(═O)OR, —C(═O)NRR, —NRR, —NRC(═O)R, —NRC(═O)OR, —NRC(═O)NRR, —OC(═O)R, —OC(═O)OR, —OC(═O)NRR, —SH, —SR, —SOR, —SO 2 R, —SO 2 NR 2 , —NRSO 2 R, —NR 2 SO 2 R, —Si(R) 3 , or —OP(OR) 3 , wherein each occurrence of R is the same or different and independently a hydrogen atom, C 1-6 alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl or substituted heterocyclealkyl, or wherein any two R groups attached to the same nitrogen atom, taken together with the nitrogen atom to which they are attached, form a heterocyclic ring or a substituted heterocyclic ring.

4. A compound of claim 3 , wherein R 1 , R 5 and R 8 are hydrogen atoms, and the compound has a structure according to Formula IV:

or a pharmaceutically acceptable salt thereof, wherein:

R 3 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, C 1-6 alkoxy optionally substituted with 1, 2, or 3 halogens, hydroxyls or amino groups, when R 2 is an optionally substituted phenyl; or, when R 2 is not an optionally substituted phenyl, R 3 is —CH 2 CH 2 —phenyl, optionally substituted with 1, 2, 3, 4, or 5 of the same or different substituents chosen from halogen, C 1-6 alkyls optionally substituted with 1, 2, or 3 halogens or hydroxyls, or —(CH) q CO 2 R 10 , wherein R 10 is a hydrogen atom or a C 1-6 alkyl, and q is the integer 0, 1, 2, 3, or 4;

one of R 6 and R 7 is -L-C(═O)OH, -L-CH═CHC(═O)OH, -L-C(═O)NH 2 , -L-C (═O)NH(C 1-3 alkyl), -L-C(═O)N(C 1-3 alkyl) 2 , -L-C(═O)CH 2 NH 2 , -LC(═O)CH 2 OH, L-C(═O)CH 2 SH, -L-C(═O)NHCN, -L-sulfo, -L-(2,6 difluorophenol), -L-phosphono, and -L-tetrazolyl, wherein L is saturated, partially saturated, or unsaturated, and is selected from the group consisting of —(CH 2 ) n —(CH2) n —, —(CH 2 ) n C(═O)(CH 2 ) n —, —(CH 2 ) n O(CH 2 ) n —, —(CH2) n O(CH 2 ) n —, and —(CH 2 ) n S(CH 2 ) n —, wherein each n is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8, wherein each carbon is optionally substituted with one or more C 1-3 alkyl or C 3-6 cycloalkyl;

5. A compound of claim 1 , having a structure according to Formula V:

or a pharmaceutically acceptable salt thereof, wherein:

one of R 6 and R 7 is -L-C(═O)OH, -L-CH═CHC(═O)OH, -L-C(═O)NH 2 , -L -C(═O)NH(C 1-3 alkyl), -L-C(═O)N(C 1-3 alkyl) 2 , -L-C(═O)NHOH, -L-C(═O)CH 2 NH 2 -LC(═O)CH 2 OH, L-C(═O)CH 2 SH, -L-C(═O)NHCN, -L-sulfo, -L-(2,6 difluorophenol), -L-phosphono, and -L-tetrazolyl, wherein L is saturated, partially saturated, or unsaturated, and is selected from the group consisting of —(CH 2 ) n —(CH2) n —,—(CH 2 ) n C(═O)(CH 2 ) n NH(CH 2 ) n —, —(CH2) n —, and —(CH 2 ) n S(CH 2 ) n —, wherein each n is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8, wherein each carbon is optionally substituted with one or more C 1-3 alkyl or C 3-6 cycloalkyl;

6. A compound of claim 5 , wherein R 1 , R 5 and R 8 are hydrogen atoms, and the compound has a structure according to Formula VI:

or a pharmaceutically acceptable salt thereof, wherein:

one of R 6 and R 7 is —(CH 2 ) n CO 2 R 11 , —O(CH 2 ) n CO 2 R 11 , or —(CH 2 ) m O(CH 2 ) p CO 2 R 11 , wherein n is the integer 0, 1, 2, 3, 4, 5, or 6, wherein m is the integer 0, 1, 2, 3, or 4, and p is the integer from 0, 1, 2, 3, 4, 5, or 6, and R 11 is a hydrogen atom or C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens, or one of R 6 and R 7 is -L-C(═O)OH, -L-CH═CHC(═O)OH, -L-C(═O)NH 2 , -L-C (═O)NH(C 1-3 alkyl), -L-C(═O)N(C 1-3 alkyl) 2 , -L-C(═O)NHOH, -L-C(═O)CH 2 NH 2 , -LC(═O)CH 2 OH, L-C(═O)CH 2 SH, -L-C(═O)NHCN, -L-sulfo, -L-(2,6 difluorophenol), -L-phosphono, and -L-tetrazolyl, wherein L is saturated, partially saturated, or unsaturated, and is selected from the group consisting of -(CH 2 ) n —(CH2) n —, —(CH 2 ) n C(═O)(CH 2 ) n —, —(CH 2 ) n NH(CH 2 ) n —, —(CH2) n O(CH 2 ) n —, and —(CH 2 ) n S(CH 2 ) n —, wherein each n is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8, wherein each carbon is optionally substituted with one or more C 1-3 alkyl or C 3-6 cycloalkyl;

R 9 and R 12 are independently 0, 1, 2, 3, 4, or 5 phenyl substituents, which are independently selected from a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl (optionally substituted with 1, 2, or 3 halogens or hydroxyl groups), C 1-6 haloalkyl, aryl, heteroaryl, heterocycle, —OR, —C(═O)R, —C(═O)OR, —C(═O)NRR, —NRR, —NRC(═O)R, —NRC(═O)OR, —NRC(═O)NRR, —OC(═O)R, —OC(═O)OR, —OC(═O)NRR, —SH, —SR, —SOR, —SO 2 R, —SO 2 NR 2 , —NRSO 2 R, —NR 2 SO 2 R, —Si(R) 3 , or —OP(OR) 3 , wherein each occurrence of R is the same or different and independently a hydrogen atom, C 1-6 alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl or substituted heterocyclealkyl, or wherein any two R groups attached to the same nitrogen atom, taken together with the nitrogen atom to which they are attached, form a heterocyclic ring or a substituted heterocyclic ring.

7. A pharmaceutical composition comprising a compound according to claim 1 in combination with a pharmaceutically acceptable carrier or excipient.

8. A method of making a compound of Formula III, comprising providing a compound having a Formula (VII)

and a compound having a Formula (VIII)

and reacting the two compounds under conditions to form a compound of Formula (III)

wherein

one of R 6 and R 7 is —(CH 2 ) n CO 2 R 11 , —O(CH 2 ) n CO 2 R 11 , or —(CH 2 ) m O(CH 2 ) p CO 2 R 11 , wherein n is the integer 0, 1, 2, 3, 4, 5, or 6, wherein m is the integer 0, 1, 2, 3, or 4, and p is the integer from 0, 1, 2, 3, 4, 5, or 6, and R 11 is a hydrogen atom or C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens, or one of R 6 and R 7 is -L-C(═O)OH, -L-CH═CHC(═O)OH, -L-C(═O)NH 2 , -L-C (═O)NH(C 1-3 alkyl), -L-C(═O)N(C 1-3 alkyl) 2 , -L-C(═O)NHOH, -L-C(═O)CH 2 NH 2 , -LC(═O)CH 2 OH, L-C(═O)CH 2 SH, -L-C(═O)NHCN, -L-sulfo, -L-(2,6 difluorophenol), -L-phosphono, and -L-tetrazolyl, wherein L is saturated, partially saturated, or unsaturated, and is selected from the group consisting of -(CH 2 ) n -(CH2) n —, —(CH 2 ) n C(═O)(CH 2 ) n —, —(CH 2 ) n NH(CH 2 ) n —, —(CH2) n O(CH 2 ) n —, and —(CH 2 ) n S(CH 2 ) n —, wherein each n is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8, wherein each carbon is optionally substituted with one or more C 1-3 alkyl or C 3-6 cycloalkyl;

9. A method of making a compound of Formula V, comprising providing a compound having a Formula (IX),

and a compound having a Formula (VIII)

and reacting the two compounds under conditions to form a compound of Formula (V),

wherein R 1 is a hydrogen atom, halogen, hydroxyl, C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens or hydroxyls, C 1-6 alkoxy —(CH) q CO 2 R 10 , wherein R 10 is a hydrogen atom or C 1-6 alkyl, and q is the integer 0, 1, 2, 3, or 4;

one of R 6 and R 7 is —(CH 2 ) n CO 2 R 11 , —O(CH 2 ) n CO 2 R 11 , or —(CH 2 ) m O(CH 2 ) p CO 2 R 11 , wherein n is the integer 0, 1, 2, 3, 4, 5, or 6, wherein m is the integer 0, 1, 2, 3, or 4, and p is the integer from 0, 1, 2, 3, 4, 5, or 6, and R 11 is a hydrogen atom or C 1-6 alkyl optionally substituted with 1, 2, or 3 halogens, or one of R 6 and R 7 is -L-C(═O)OH, -L-CH═CHC(═O)OH, -L-C(═O)NH 2 , -L-C (═O)NH(C 1-3 alkyl), -L-C(═O)N(C 1-3 alkyl) 2 , -L-C(═O)NHOH, -L-C(═O)CH 2 NH 2 -LC(═O)CH 2 OH, L-C(═O)CH 2 SH, -L-C (═O)NHCN, -L-sulfo, -L-(2,6 difluorophenol), -L-phosphono, and -L-tetrazolyl, wherein L is saturated, partially saturated, or unsaturated, and is selected from the group consisting of —(CH 2 ) n —(CH2) n —(CH 2 ) n C(═O)(CH 2 ) n —, —(CH 2 ) n NH(CH 2 ) n —, —(CH2) n O(CH 2 ) n —, and —(CH 2 ) n S(CH 2 ) n —, wherein each n is an integer independently selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8, wherein each carbon is optionally substituted with one or more C 1-3 alkyl or C 3-6 cycloalkyl;

10. A compound chosen from:

4-[4-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-butyric acid;

3-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-benzoic acid;

2-Chloro-5-(2-methyl-3,5-diphenyl-pyrrol-1-yl)-benzoic acid;

4-Methoxy-3-(2-methyl-3,5-diphenyl-pyrrol-1-yl)-benzoic acid;

3-[3-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-propionic acid;

3-(2,4-Diphenyl-pyrrol-1-yl)-benzoic acid;

4-[4-(2,4-Diphenyl-pyrrol-1-yl)-phenyl]-butyric acid;

3-[2-Methyl-5-phenyl-3-(3-trifluoromethyl-phenyl)-pyrrol-1-yl]-benzoic acid;

3-{3[2-Methyl-5-phenyl-3-(3-trifluoromethyl-phenyl)-pyrrol-1-yl]-phenyl}-propionic acid;

4-{4[2-Methyl-5-phenyl-3-(3-trifluoromethyl-phenyl)-pyrrol-1-yl]-phenyl}-butyric acid;

3-(2-Ethyl-3,5-diphenyl-pyrrol-1-yl)-benzoic acid;

3-[3-(2-Ethyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-propionic acid;

4-[4-(2-Ethyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-butyric acid;

3-[2-Methyl-3-phenyl-5-(4-trifluoromethyl-phenyl)-pyrrol-1-yl]-benzoic acid;

3-{3[2-Methyl-3-phenyl-5-(4-trifluoromethyl-phenyl)-pyrrol-1-yl]-phenyl}-propionic acid;

4-{4[2-Methyl-3-phenyl-5-(4-trifluoromethyl-phenyl)-pyrrol-1-yl]-phenyl}-butyric acid;

3-[5-(3,4-Dichloro-phenyl)-2-methyl-3-phenyl-pyrrol-1-yl]-benzoic acid;

3-{3-[5-(3,4-Dichloro-phenyl)-2-methyl-3-phenyl-pyrrol-1-yl]-phenyl}-propionic acid;

4-{4-[5-(3,4-Dichloro-phenyl)-2-methyl-3-phenyl-pyrrol-1-yl]-phenyl}-butyric acid;

1-(3-Carboxy-phenyl)-5-phenethyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester;

1[3-(2—Carboxy-ethyl)-phenyl]-5-phenethyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester;

1-[4-(3-Carboxy-propyl)-phenyl]-5-phenethyl-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester;

3-(2-Phenethyl-5-phenyl-pyrrol-1-yl)-benzoic acid;

3-[3-(2-Phenethyl-5-phenyl-pyrrol-1-yl)-phenyl]-propionic acid;

4-[4-(2-Phenethyl-5-phenyl-pyrrol-1-yl)-phenyl]-butyric acid;

[3-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-phenoxy]-acetic acid;

3-[4-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-phenoxy]-propionic acid methyl ester;

3-[4-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-phenoxy]-propionic acid;

4-[4-(2-Cyclohexyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-butyric acid;

3-(2-Isopropyl-3,5-diphenyl-pyrrol-1-yl)-benzoic acid;

3-[3-(2-Isopropyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-propionic acid;

4-[4-(2-Isopropyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-butyric acid;

3-(2-Cyclopropyl-3,5-diphenyl-pyrrol-1-yl)-benzoic acid;

3-[3-(2-Cyclopropyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-propionic acid;

4-[4-(2-Cyclopropyl-3,5-diphenyl-pyrrol-1-yl)-phenyl]-butyric acid;

3-[2-(2,2-Dimethyl-propyl)-3,5-diphenyl-pyrrol-1-yl]-benzoic acid;

3-{3-[2-(2,2-Dimethyl-propyl)-3,5-diphenyl-pyrrol-1-yl]-phenyl}-propionic acid;

4-{4[2-(2,2-Dimethyl-propyl)-3,5-diphenyl-pyrrol-1-yl]-phenyl}-butyric acid; or 4-(2-Methyl-3,5-diphenyl-pyrrol-1-yl)-benzoic acid.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2012

From: MYREXIS, INC.

To: MANFREDI, JOHN

Reel/Frame 028546/0950 →

CHANGE OF NAME Recorded Aug 3, 2010

From: MYRIAD PHARMACEUTICALS, INC.

To: MYREXIS, INC.

Reel/Frame 024780/0705 →

Continuity (5)

Continuation 12057140 · Mar 27, 2008

Continuation In Part PCTUS2006037903 · Sep 27, 2006

Provisional Application 60721415 · Sep 27, 2005

Provisional Application 60786556 · Mar 27, 2006

Related Publication 20100216862A1 · Aug 26, 2010