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US 10,604,520 B2Granted
N-acyl amino acid compounds and methods of use
AssigneePliant Therapeutics, Inc.
InventorsLan Jiang, David John Morgans, Jr., Gustave Bergnes, Chun Chen, Hui Li, Patrick Andre, Randall L. Halcomb, Jacob Cha, Timothy Hom
Life of this patent
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Abstract
The invention relates to compounds of formula (I): or a salt thereof, wherein R1, A, L, and R2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are αvβ1 integrin inhibitors that are useful for treating tissue specific fibrosis.
Claims52
A compound of formula (I):
- or a salt thereof, wherein:
- R1 is C6-C14 aryl or 5- to 10-membered heteroaryl, wherein the C6-C14 aryl and 5- to 10-membered heteroaryl of R1 are independently optionally substituted by R10;
- R2 is
- 5- to 10-membered heteroaryl containing at least 2 ring nitrogen atoms,
- 3- to 12-membered heterocyclyl containing at least 2 ring nitrogen atoms,
- —NH—R3,
- —R3—R10, or
- —R3—NR3aR3b,
- wherein the 5- to 10-membered heteroaryl and 3- to 12-membered heterocyclyl of R2 are independently optionally substituted by R10;
- R3 is 5- to 10-membered heteroaryl containing at least 1 ring nitrogen atom, or 3- to 12-membered heterocyclyl containing at least 1 ring nitrogen atom, wherein the 5- to 10-membered heteroaryl and 3- to 12-membered heterocyclyl of R3 are independently optionally substituted by R10;
- -A-L- is -A3-;
- or -A-L- is -A1-L1- or -A2-L2-, and R2 is 5- to 10-membered heteroaryl, 3- to 12-membered heterocyclyl, —NH-(5- to 10-membered heteroaryl), or —NH-(3- to 12-membered heterocyclyl), wherein the 5- to 10-membered heteroaryl and 3- to 12-membered heterocyclyl of R2 contain at least 2 ring nitrogen atoms and are independently optionally substituted by R10;
- A1 is C3-C8 cycloalkylene, C3-C8 cycloalkenylene, C6-C14 arylene, 5- to 10-membered heteroarylene or 3- to 12-membered heterocyclylene, wherein the C3-C8 cycloalkylene, C3-C8 cycloalkenylene, C6-C14 arylene, 5- to 10-membered heteroarylene and 3- to 12-membered heterocyclylene of A1 are independently optionally substituted by R10;
- A2 is C3-C8 alkylene or C3-C8 alkenylene, wherein the C3-C8 alkylene and C3-C8 alkenylene of A2 are independently optionally substituted by R9;
- A3 is C5-C10 alkylene or C5-C10 alkenylene, wherein the C5-C10 alkylene and C5-C10 alkenylene of A3 are independently optionally substituted by R9;
- L1
- is —O—Z—, —O—Z—X1—, —O—Y1—, —O—Y1—X1—, —O—Z—Y1—, —O—Z—Y1—X1—, —O—Z—X1—Y1—, —O—Z—X1—Y1—X1—, —Z—O—Z—, —X1—Z—O—Z—, —Z—O—Z—X1—, —X1—Z—O—Z—X1—, —Z—O—Y1—, —Z—O—Y1—X1—, —X1—Z—O—Y1—, —X1—Z—O—Y1—X1—, —N(R4)—Z—, —N(R4)—Z—X1—, X2, —X2—Y1—, Y2, or —Y2—X2—;
- L2 is C3-C6 cycloalkylene optionally substituted by R10;
- each X1 is independently C1-C6 alkylene or C2-C6 alkenylene, wherein the C1-C6 alkylene and C2-C6 alkenylene of X1 are independently optionally substituted by R10;
- each X2 is independently C1-C6 alkylene or C2-C6 alkenylene, wherein the C1-C6 alkylene and C2-C6 alkenylene of X2 are independently optionally substituted by R9;
- each Y1 is independently C3-C6 cycloalkylene optionally substituted by R10;
- each Y2 is independently saturated 3- to 4-membered heterocyclylene optionally substituted by R10;
- each Z is independently —CR5aR5b—;
- each R3a, R3b, R4, R5a and R5b is independently H or C1-C6 alkyl;
- each R9 is independently C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl,
- halogen, —CN, —OR11, —SR11, —NR12R13, —NO2, —C═NH(OR11), —C(O)R11, —OC(O)R11, —C(O)OR11, —C(O)NR12R13, —NR11C(O)R12, —NR11C(O)OR12, —NR11C(O)NR12R13, —S(O)R11, —S(O)2R11, —NR11S(O)R12, —NR11S(O)2R12, —S(O)NR12R13, —S(O)2NR12R13, —P(O)(OR12)(OR13), C3-C8 cycloalkyl, 3- to 12-membered heterocyclyl, 5- to 10-membered heteroaryl or C6-C14 aryl, wherein each R9 is independently optionally substituted by halogen,
- oxo, —OR14, —NR14R15, —C(O)R14, —CN, —S(O)R14, —S(O)2R14, —P(O)(OR14)(OR15), C3-C8 cycloalkyl, 3- to 12-membered heterocyclyl, 5- to 10-membered heteroaryl, C6-C14 aryl, or C1-C6 alkyl optionally substituted by oxo, —OH or halogen;
- each R10 is independently oxo or R9;
- R11 is independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C6-C14 aryl, 5- to 6-membered heteroaryl or 3- to 6-membered heterocyclyl, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C6-C14 aryl, 5- to 6-membered heteroaryl and 3- to 6-membered heterocyclyl are independently optionally substituted by halogen,
- oxo, —CN, —OR16, —NR16R17, —P(O)(OR16)(OR17), or C1-C6 alkyl optionally substituted by halogen, —OH or oxo;
- R12 and R13 are each independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C6-C14 aryl, 5- to 6-membered heteroaryl or 3- to 6-membered heterocyclyl, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C6-C14 aryl, 5- to 6-membered heteroaryl and 3- to 6-membered heterocyclyl are independently optionally substituted by halogen, oxo, —CN, —OR16, —NR16R17 or C1-C6 alkyl optionally substituted by halogen, —OH or oxo;
- or R12 and R13 are taken together with the atom to which they attached to form a 3- to 6-membered heterocyclyl optionally substituted by halogen, oxo, —OR16, —NR16R17 or C1-C6 alkyl optionally substituted by halogen, oxo or —OH;
- R14 and R15 are each independently hydrogen, C1-C6 alkyl optionally substituted by halogen or oxo, C2-C6 alkenyl optionally substituted by halogen or oxo, or C2-C6 alkynyl optionally substituted by halogen or oxo;
- or R14 and R15 are taken together with the atom to which they attached to form a 3- to 6-membered heterocyclyl optionally substituted by halogen, oxo or C1-C6 alkyl optionally substituted by halogen or oxo;
- and
- R16 and R17 are each independently hydrogen, C1-C6 alkyl optionally substituted by halogen or oxo, C2-C6 alkenyl optionally substituted by halogen or oxo, or C2-C6 alkynyl optionally substituted by halogen or oxo;
- or R16 and R17 are taken together with the atom to which they attached to form a 3-6 membered heterocyclyl optionally substituted by halogen, oxo or C1-C6 alkyl optionally substituted by oxo or halogen;
- provided that the compound is other than:
- L-Tyrosine, N-[(5-chloro-1,3-benzodioxol-4-yl)carbonyl]-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (3x);
- L-Tyrosine, N-[(3-chloro-1-methyl-1H-indol-2-yl)carbonyl]-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (4x);
- L-Tyrosine, N-[[1-cyclohexyl-2-(3-furanyl)-1H-benzimidazol-5-yl]carbonyl]-O-(1H-tetrazol-5-ylmethyl)- (5x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)methyl]- (6x);
- L-Tyrosine, N-(2-chloro-4-methoxybenzoyl)-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (7x);
- L-Tyrosine, N-(2-chloro-6-methylbenzoyl)-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (8x);
- L-Tyrosine, N-(2-fluoro-6-methylbenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (9x);
- L-Tyrosine, N-[(2-ethyl-3-thienyl)carbonyl]-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (10x);
- L-Tryptophan, N-benzoyl-5-[4-(1-piperazinyl)butoxyl- (11x);
- L-Tyrosine, N-(2-chlorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (12x);
- L-Tyrosine, N-[(3-chloro-2-thienyl)carbonyl]-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (13x);
- 2-Pyridinepropanoic acid, α-[(2,6-dichlorobenzoyl)amino]-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (14x);
- L-Tyrosine, N-(2-chloro-6-fluorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (15x);
- L-Tyrosine, N-[(3-chloro-4-pyridinyl)carbonyl]-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (16x),
- L-Tyrosine, O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]-N-(2,4,6-trimethylbenzoyl)- (17x);
- L-Tyrosine, N-[(3,5-dichloro-4-pyridinyl)carbonyl]-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (18x);
- L-Tyrosine, N-(2,4-dichlorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (19x);
- 2-Pyridinepropanoic acid, α-[(2-chloro-4-methoxybenzoyl)amino]-5-[2(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (20x);
- 2-Pyridinepropanoic acid, α-[(2-chlorobenzoyl)amino]-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (21x);
- L-Tyrosine, N-(2-chloro-6-fluoro-3-methylbenzoyl)-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (22x);
- 3-Pyridinepropanoic acid, α-[(2-chlorobenzoyl)amino]-6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (23x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (24x);
- L-Tyrosine, N-(2-chloro-6-fluorobenzoyl)-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (25x);
- L-Tyrosine, N-(2-chloro-5-fluorobenzoyl)-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (26x);
- 2-Naphthalenepropanoic acid, α-(benzoylamino)-6-[2-(1-piperazinyl)ethoxy]- (27x);
- L-Tyrosine, O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]-N-(2-ethyl-4-fluorobenzoyl)- (28x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-5-methyl-1,8-naphthyridin-2-yl)ethyl]- (29x);
- 2-Pyridinepropanoic acid, α-[[(3-chloro-2-thienyl)carbonyl]amino]-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (30x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[2-(1,2,3,4-tetrahydro-1-methylpyrido[2,3-b]pyrazin-6-yl)ethyl]- (31x);
- L-Tryptophan, N-benzoyl-5-[3-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]propoxy]- (32x),
- L-Tyrosine, N-(2,6-dimethylbenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (33x);
- L-Tyrosine, O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]-N-[(3-methyl-4-pyridinyl)carbonyl]- (34x);
- L-Tyrosine, N-(2-chloro-6-methylbenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (35x);
- L-Tyrosine, N-[(3-chloro-2-thienyl)carbonyl]-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (36x);
- 2-Thiophenepropanoic acid, α-[[(3,5-dichloro-4-pyridinyl)carbonyl]amino]-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (37x);
- L-Tyrosine, N-(2-chloro-3,6-difluorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (38x);
- 2-Pyridinepropanoic acid, α-[(2-fluoro-4-methylbenzoyl)amino]-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (39x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-4-methyl-1,8-naphthyridin-2-yl)ethyl]- (40x),
- 2-Pyridinepropanoic acid, α-[(2-chloro-4-fluorobenzoyl)amino]-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (41x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (42x);
- 3-Pyridinepropanoic acid, α-[(2-chloro-4-fluorobenzoyl)amino]-6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (43x);
- L-Tyrosine, N-(2-chlorobenzoyl)-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (44x);
- L-Tyrosine, O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]-N-(2-ethyl-5-fluorobenzoyl)- (45x);
- 1-Piperazinecarboxylic acid, 4-[2-[[6-[2-(benzoylamino)-2-carboxyethyl]-2-naphthalenyl]oxy]ethyl]-, 1-(1,1-dimethylethyl) ester (46x);
- L-Tyrosine, O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]-N-(2,4,6-trimethylbenzoyl)- (47x);
- L-Tyrosine, O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]-N-(2,6-dimethylbenzoyl)- (48x);
- 3-Pyridinepropanoic acid, α-[[(3-chloro-2-thienyl)carbonyl]amino]-6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (49x);
- L-Tryptophan, N-benzoyl-5-[4-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]butoxy]- (50x);
- L-Tyrosine, N-(2-methylbenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (51 x);
- L-Tyrosine, N-[(3,5-dichloro-4-pyridinyl)carbonyl]-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (52x),
- L-Tryptophan, N-benzoyl-5-[3-(1-piperazinyl)propoxy]- (53x);
- L-Tyrosine, N-(6-chloro-2-fluoro-3-methylbenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (54x);
- L-Tyrosine, N-[(4-methoxy-3-thienyl)carbonyl]-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (55x);
- L-Tyrosine, N-(2-chloro-4-fluorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (56x);
- L-Tyrosine, O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]-N-[(3,5-dimethyl-4-isoxazolyl)carbonyl]- (57x);
- L-Tyrosine, N-(2-chloro-5-methylbenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]- (58x);
- 2-Pyridinepropanoic acid, α-[(2-ethyl-4-fluorobenzoyl)amino]-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, αS)- (59x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-7-methyl-1,8-naphthyridin-2-yl)ethyl]- (60x);
- 2-Pyridinepropanoic acid, α-[(2-chloro-6-fluorobenzoyl)amino]-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxyl-, (αS)- (61x),
- 3-Pyridinepropanoic acid, α-(2-chloro-6-fluorobenzoyl)amino]-6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (62x);
- L-Tyrosine, N-(2-chloro-4-fluorobenzoyl)-O-[2-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)ethyl]- (63x),
- 3-Pyridinepropanoic acid, α-[(2,6-dichlorobenzoyl)amino]-6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]-, (αS)- (64x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl] (65x);
- L-Tyrosine, N-(2,6-dichlorobenzoyl)-O-[2-methyl-2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]- (66x);
- L-Tyrosine, O-[3-(4-pyrimidinylamino)propyl]-N-(2,4,6-trimethylbenzoyl)- (77x);
- L-Tyrosine, N-benzoyl-O-[4-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]butyl]- (81x);
- L-Tyrosine, O-[2-(2-benzothiazolylamino)ethyl]-N-(2,6-dichlorobenzoyl)- (89x);
- L-Tyrosine, O-[3-[(1,4,5,6-tetrahydro-2-pyrimidinyl)amino]propyl]-N-(2,4,6-trimethylbenzol)- (93x);
- L-Tyrosine, O-[3-(2-pyrimidinylamino)propyl]-N-(2,4,6-trimethylbenzoyl)- (95x);
- L-Tyrosine, O-[2-(1H-benzimidazol-2-ylamino)ethyl]-N-(2,6-dichlorobenzoyl)- (96x);
- L-Tyrosine, N-benzoyl-O-[4-(2-pyrimidinylamino)butyl]- (98x);
- L-Tyrosine, O-[3-[(1,4,5,6-tetrahydro-2-pyrazinyl)amino]propyl]-N-(2,4,6-trimethylbenzoyl)- (109x);
- L-Tyrosine, O-[3-(2-pyrazinylamino)propyl]-N-(2,4,6-trimethylbenzol)- (111 x);
- 2-Thiophenepropanoic acid, a-[(2-chloro-4-fluorobenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (126x);
- 2-Pyridinepropanoic acid, α-[(2-chlorobenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (127x);
- 3-Pyridinepropanoic acid, α-[(2-chloro-4-fluorobenzoyl)amino]-6-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (128x);
- 2-Thiophenepropanoic acid, α-[[(3,5-dichloro-4-pyridinyl)carbonyl]amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (129x);
- L-Phenylalanine, N-(2-chloro-4-fluorobenzoyl)-4-[3-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)propyl]- (130x);
- 2-Thiophenepropanoic acid, α-[(2-chloro-6-fluorobenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl], (αS)- (131x);
- 2-Pyridinepropanoic acid, α-[(2-fluoro-6-methylbenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (132x);
- 3-Pyridinepropanoic acid, α-[(2-chloro-6-fluorobenzoyl)amino]-6-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl-, (αS)- (133x);
- L-Phenylalanine, N-(2,6-dichlorobenzoyl)-4-[3-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)propyl]- (134x);
- 2-Thiophenepropanoic acid, α-(2,6-dichlorobenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl-, (αS)- (135x);
- 2-Pyridinepropanoic acid, α-(2-chloro-4-fluorobenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (136x);
- 2-Pyridinepropanoic acid, α-[[(3-chloro-2-thienyl)carbonyl]amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (137x);
- L-Phenylalanine, N-(2-chlorobenzoyl)-4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]- (138x);
- L-Phenylalanine, N-(2-chloro-6-fluorobenzoyl)-4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]- (139x);
- 2-Pyridinepropanoic acid, α-[(2-chloro-6-fluorobenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (140x);
- 2-Pyridinepropanoic acid, α-[(2,6-dichlorobenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (141x);
- L-Phenylalanine, N-(2,6-dichlorobenzoyl)-4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]- (142x);
- 3-Pyridinepropanoic acid, α-[(2,6-dichlorobenzoyl)amino]-6-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (143x);
- L-Phenylalanine, N-[(3,5-dimethyl-4-isoxazolyl)carbonyl]-4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]- (144x);
- L-Phenylalanine, N-(2-chlorobenzoyl)-4-[3-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)propyl]- (145x);
- 2-Thiophenepropanoic acid, α-[[3-[(dimethylamino)methyl]benzoyl]amino]-5-[(8-methyl-6,10-dioxo-7,9-diazaspiro[4.5]dec-7-en-9-yl)methyl]- (146x);
- 2-Thiophenepropanoic acid, α-[(2-chlorobenzoyl)amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (147x);
- L-Phenylalanine, N-(2-chloro-4-fluorobenzoyl)-4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]- (148x);
- 3-Pyridinepropanoic acid, α-[(2-chlorobenzoyl)amino]-6-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (149x);
- 2-Thiophenepropanoic acid, α-[[(3,5-dimethyl-4-isoxazolyl)carbonyl]amino]-5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (150x);
- L-Phenylalanine, N-(2-chloro-6-fluorobenzoyl)-4-[3-(3,4-dihydro-2H-pyrido[3,2-b]-1,4-oxazin-6-yl)propyl]- (151x);
- 3-Pyridinepropanoic acid, α-[[(3-chloro-2-thienyl)carbonyl]amino]-6-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-, (αS)- (152x);
- or
- 1,8-Naphthyridine-2-nonanoic acid, α-(benzoylamino)- 5,6,7,8-tetrahydro-, (αS)- (164x),
- or a salt thereof.
138 more elements
Dependencies are inferred from the claim text.