CA3042707A1 - 3-substituted propionic acids as .alpha.v integrin inhibitors - Google Patents
3-substituted propionic acids as .alpha.v integrin inhibitors Download PDFInfo
- Publication number
- CA3042707A1 CA3042707A1 CA3042707A CA3042707A CA3042707A1 CA 3042707 A1 CA3042707 A1 CA 3042707A1 CA 3042707 A CA3042707 A CA 3042707A CA 3042707 A CA3042707 A CA 3042707A CA 3042707 A1 CA3042707 A1 CA 3042707A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydro
- naphthyridin
- propanoic acid
- propyl
- pyrazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 3-substituted propionic acids Chemical class 0.000 title claims description 135
- 102000006495 integrins Human genes 0.000 title abstract description 26
- 108010044426 integrins Proteins 0.000 title abstract description 26
- 239000003112 inhibitor Substances 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 195
- 238000000034 method Methods 0.000 claims abstract description 113
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 208000035475 disorder Diseases 0.000 claims abstract description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 16
- 230000004761 fibrosis Effects 0.000 claims abstract description 16
- 201000011510 cancer Diseases 0.000 claims abstract description 13
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- 230000001575 pathological effect Effects 0.000 claims abstract description 6
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 3
- 206010052779 Transplant rejections Diseases 0.000 claims abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 146
- 235000019260 propionic acid Nutrition 0.000 claims description 119
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 114
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 108
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 125000000623 heterocyclic group Chemical group 0.000 claims description 87
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000001188 haloalkyl group Chemical group 0.000 claims description 41
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 33
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 29
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 22
- 229940124530 sulfonamide Drugs 0.000 claims description 22
- 150000003456 sulfonamides Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 20
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 16
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 15
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 14
- 125000003368 amide group Chemical group 0.000 claims description 14
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 239000004475 Arginine Substances 0.000 claims description 12
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 210000004185 liver Anatomy 0.000 claims description 8
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 6
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 5
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 208000020832 chronic kidney disease Diseases 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 2
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 230000000747 cardiac effect Effects 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 210000003679 cervix uteri Anatomy 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 210000004696 endometrium Anatomy 0.000 claims description 2
- 210000003238 esophagus Anatomy 0.000 claims description 2
- 210000000232 gallbladder Anatomy 0.000 claims description 2
- 210000004392 genitalia Anatomy 0.000 claims description 2
- 210000003128 head Anatomy 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 210000002429 large intestine Anatomy 0.000 claims description 2
- 210000000867 larynx Anatomy 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 210000002200 mouth mucosa Anatomy 0.000 claims description 2
- 210000003205 muscle Anatomy 0.000 claims description 2
- 210000002850 nasal mucosa Anatomy 0.000 claims description 2
- 210000003739 neck Anatomy 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 230000002685 pulmonary effect Effects 0.000 claims description 2
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 2
- 210000003491 skin Anatomy 0.000 claims description 2
- 210000000813 small intestine Anatomy 0.000 claims description 2
- 210000000952 spleen Anatomy 0.000 claims description 2
- 210000001550 testis Anatomy 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- 210000001685 thyroid gland Anatomy 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- WEUQFTALWGFGGZ-UHFFFAOYSA-N 3-(5-morpholin-4-ylpyridin-3-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)CC(c1cncc(c1)N1CCOCC1)n1nccc1CCCc1ccc2CCCNc2n1 WEUQFTALWGFGGZ-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- LUNGOZZVVOHVRP-PKOBYXMFSA-N COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCC[C@@H]1NC2=NC=CC=C2CC1 Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCC[C@@H]1NC2=NC=CC=C2CC1 LUNGOZZVVOHVRP-PKOBYXMFSA-N 0.000 claims 2
- LUNGOZZVVOHVRP-IEBWSBKVSA-N COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCC[C@H]1NC2=NC=CC=C2CC1 Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCC[C@H]1NC2=NC=CC=C2CC1 LUNGOZZVVOHVRP-IEBWSBKVSA-N 0.000 claims 2
- LUNGOZZVVOHVRP-HKUYNNGSSA-N COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCC[C@@H]1NC2=NC=CC=C2CC1 Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCC[C@@H]1NC2=NC=CC=C2CC1 LUNGOZZVVOHVRP-HKUYNNGSSA-N 0.000 claims 2
- LUNGOZZVVOHVRP-MJGOQNOKSA-N COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCC[C@H]1NC2=NC=CC=C2CC1 Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCC[C@H]1NC2=NC=CC=C2CC1 LUNGOZZVVOHVRP-MJGOQNOKSA-N 0.000 claims 2
- RIQIKORYQBMUTL-HXUWFJFHSA-N (2R)-2-(3-fluoro-4-methoxyphenyl)-3-[5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ccc(cc1F)[C@@H](Cc1ncc(CCCCc2ccc3CCCNc3n2)s1)C(O)=O RIQIKORYQBMUTL-HXUWFJFHSA-N 0.000 claims 1
- RIQIKORYQBMUTL-FQEVSTJZSA-N (2S)-2-(3-fluoro-4-methoxyphenyl)-3-[5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ccc(cc1F)[C@H](Cc1ncc(CCCCc2ccc3CCCNc3n2)s1)C(O)=O RIQIKORYQBMUTL-FQEVSTJZSA-N 0.000 claims 1
- CNBKWJCVGKLONT-HXUWFJFHSA-N (3R)-3-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@@H](N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1)C1=CN=C2OCCOC2=C1 CNBKWJCVGKLONT-HXUWFJFHSA-N 0.000 claims 1
- JEWVDLUACRWTEW-HXUWFJFHSA-N (3R)-3-(2-ethoxypyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound CCOC1=NC=C(C=N1)[C@@H](CC(O)=O)N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1 JEWVDLUACRWTEW-HXUWFJFHSA-N 0.000 claims 1
- QMBVMQULMAFHDB-HXUWFJFHSA-N (3R)-3-(2-ethoxypyrimidin-5-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CCOC1=NC=C(C=N1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 QMBVMQULMAFHDB-HXUWFJFHSA-N 0.000 claims 1
- UBYJRGAFVQXRIU-LJQANCHMSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ncc(cn1)[C@@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 UBYJRGAFVQXRIU-LJQANCHMSA-N 0.000 claims 1
- CBEDCDMHOQWJRM-HXUWFJFHSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@@H](CC(=O)O)N1N=C(C=C1)CCCC=1C=CC2=C(NCCCC2)N=1 CBEDCDMHOQWJRM-HXUWFJFHSA-N 0.000 claims 1
- DAJVJLDTALOMRU-GOSISDBHSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 DAJVJLDTALOMRU-GOSISDBHSA-N 0.000 claims 1
- JEJVFRHYKOLBOR-GOSISDBHSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]triazol-2-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@@H](CC(=O)O)N1N=CC(=N1)CCCC1=NC=2NCCCC=2C=C1 JEJVFRHYKOLBOR-GOSISDBHSA-N 0.000 claims 1
- IFPMYGLSHXXRFZ-LJQANCHMSA-N (3R)-3-(2-methoxypyrimidin-5-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 IFPMYGLSHXXRFZ-LJQANCHMSA-N 0.000 claims 1
- ZKJMYZGFBDUOAC-HXUWFJFHSA-N (3R)-3-(2-methylpyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound Cc1ncc(cn1)[C@@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 ZKJMYZGFBDUOAC-HXUWFJFHSA-N 0.000 claims 1
- YZJQEJHDCYMNMO-OAQYLSRUSA-N (3R)-3-(2-methylpyrimidin-5-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound Cc1ncc(cn1)[C@@H](CC(O)=O)n1ccc(CCCc2ccc3CCCCNc3n2)n1 YZJQEJHDCYMNMO-OAQYLSRUSA-N 0.000 claims 1
- BCBRXDHPNAOLSW-LJQANCHMSA-N (3R)-3-(2-methylpyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound Cc1ncc(cn1)[C@@H](CC(O)=O)c1nc(CCCc2ccc3CCCNc3n2)cs1 BCBRXDHPNAOLSW-LJQANCHMSA-N 0.000 claims 1
- KOZUTVCXHZESNP-HXUWFJFHSA-N (3R)-3-(3,4-dimethoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(OC)C=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 KOZUTVCXHZESNP-HXUWFJFHSA-N 0.000 claims 1
- GDBNGKQEPUAMCI-OAQYLSRUSA-N (3R)-3-(3,4-dimethoxyphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC=1C=C(C=CC=1OC)[C@@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 GDBNGKQEPUAMCI-OAQYLSRUSA-N 0.000 claims 1
- HVDGUXVTAKZNCH-LJQANCHMSA-N (3R)-3-(3,5-dimethylpyrazol-1-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=NN(C(=C1)C)[C@H](CC(=O)O)C=1SC=C(N=1)CCCC1=NC=2NCCCC=2C=C1 HVDGUXVTAKZNCH-LJQANCHMSA-N 0.000 claims 1
- QGFWAHQPFIYBOM-OAQYLSRUSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[1-methyl-4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]imidazol-2-yl]propanoic acid Chemical compound FC=1C=C(C=CC=1OC)[C@@H](CC(=O)O)C=1N(C=C(N=1)CCCCC1=NC=2NCCCC=2C=C1)C QGFWAHQPFIYBOM-OAQYLSRUSA-N 0.000 claims 1
- ROKVLOGQHMXEJC-OAQYLSRUSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[1-methyl-5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]imidazol-2-yl]propanoic acid Chemical compound FC=1C=C(C=CC=1OC)[C@@H](CC(=O)O)C=1N(C(=CN=1)CCCCC1=NC=2NCCCC=2C=C1)C ROKVLOGQHMXEJC-OAQYLSRUSA-N 0.000 claims 1
- IRRAOOUFBQNPFO-GOSISDBHSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[2-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-4-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@@H](CC(O)=O)C1=CSC(CCCC2=CC=C3CCCNC3=N2)=N1 IRRAOOUFBQNPFO-GOSISDBHSA-N 0.000 claims 1
- DOUMICIFYPBLQH-LJQANCHMSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-oxazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CO1 DOUMICIFYPBLQH-LJQANCHMSA-N 0.000 claims 1
- ZDRWXUHIAQJLBM-LJQANCHMSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 ZDRWXUHIAQJLBM-LJQANCHMSA-N 0.000 claims 1
- YEVCJKDMMKTHNO-HXUWFJFHSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]triazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@@H](CC(O)=O)N1N=CC(CCCC2=CC=C3CCCNC3=N2)=N1 YEVCJKDMMKTHNO-HXUWFJFHSA-N 0.000 claims 1
- YXDUBNYLAAIZFB-HXUWFJFHSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 YXDUBNYLAAIZFB-HXUWFJFHSA-N 0.000 claims 1
- QMQQAYAICVRTEQ-LJQANCHMSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@@H](CC(O)=O)C1=NC=C(CCCC2=CC=C3CCCNC3=N2)S1 QMQQAYAICVRTEQ-LJQANCHMSA-N 0.000 claims 1
- ZPSSHXXWTPHCDU-LJQANCHMSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1H-pyrazol-3-yl]propanoic acid Chemical compound COc1ccc(cc1F)[C@@H](CC(O)=O)c1cc(CCCc2ccc3CCCNc3n2)[nH]n1 ZPSSHXXWTPHCDU-LJQANCHMSA-N 0.000 claims 1
- AATLLCJAZYCLSY-HXUWFJFHSA-N (3R)-3-(3-fluoro-4-methoxyphenyl)-3-[5-methyl-4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-oxazol-2-yl]propanoic acid Chemical compound COc1ccc(cc1F)[C@@H](CC(O)=O)c1nc(CCCCc2ccc3CCCNc3n2)c(C)o1 AATLLCJAZYCLSY-HXUWFJFHSA-N 0.000 claims 1
- LVZQWYRNDVVBAH-RUZDIDTESA-N (3R)-3-(3-morpholin-4-ylphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound OC(=O)C[C@@H](C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1)C1=CC(=CC=C1)N1CCOCC1 LVZQWYRNDVVBAH-RUZDIDTESA-N 0.000 claims 1
- XIVCRSBEVGNWMB-OAQYLSRUSA-N (3R)-3-(5-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1cncc(c1)[C@@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 XIVCRSBEVGNWMB-OAQYLSRUSA-N 0.000 claims 1
- REHWTMUCNPCVOK-HXUWFJFHSA-N (3R)-3-(5-methylpyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=CN=CC(=C1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 REHWTMUCNPCVOK-HXUWFJFHSA-N 0.000 claims 1
- IABHYNPYOQIKNL-HXUWFJFHSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[1-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-4-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@@H](CC(O)=O)c1cnn(CCCc2ccc3CCCNc3n2)c1 IABHYNPYOQIKNL-HXUWFJFHSA-N 0.000 claims 1
- QRQPTVHWXMVXDU-OAQYLSRUSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[1-methyl-5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]imidazol-2-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@@H](CC(O)=O)c1ncc(CCCCc2ccc3CCCNc3n2)n1C QRQPTVHWXMVXDU-OAQYLSRUSA-N 0.000 claims 1
- VXWFWYADNINHES-HXUWFJFHSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 VXWFWYADNINHES-HXUWFJFHSA-N 0.000 claims 1
- MBIIFYIIXDIURN-OAQYLSRUSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@@H](CC(O)=O)n1ccc(CCCc2ccc3CCCCNc3n2)n1 MBIIFYIIXDIURN-OAQYLSRUSA-N 0.000 claims 1
- WWVUBEGMDOTPPR-LJQANCHMSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@@H](CC(O)=O)c1nc(CCCc2ccc3CCCNc3n2)cs1 WWVUBEGMDOTPPR-LJQANCHMSA-N 0.000 claims 1
- MOSAYWZXWIYPJY-LJQANCHMSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]triazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](CC(O)=O)N1N=CC(CCCC2=CC=C3CCCNC3=N2)=N1 MOSAYWZXWIYPJY-LJQANCHMSA-N 0.000 claims 1
- CGAASNMVFHAXRP-HXUWFJFHSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 CGAASNMVFHAXRP-HXUWFJFHSA-N 0.000 claims 1
- SXFILBGBIGGRAC-LJQANCHMSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@@H](CC(O)=O)c1ncc(CCCc2ccc3CCCNc3n2)s1 SXFILBGBIGGRAC-LJQANCHMSA-N 0.000 claims 1
- KWQAOJZTPSJWFI-HXUWFJFHSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)C=1SC(=CN=1)CCCCC1=NC=2NCCCC=2C=C1 KWQAOJZTPSJWFI-HXUWFJFHSA-N 0.000 claims 1
- KZDCPPDMQHBFFY-JOCHJYFZSA-N (3R)-3-[3-(dimethylcarbamoyl)phenyl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=CC=CC(=C1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 KZDCPPDMQHBFFY-JOCHJYFZSA-N 0.000 claims 1
- GUDIIKKLVLPESU-HSZRJFAPSA-N (3R)-3-[3-(dimethylcarbamoyl)phenyl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=CC=CC(=C1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 GUDIIKKLVLPESU-HSZRJFAPSA-N 0.000 claims 1
- AABSHUYBOADMEL-OAQYLSRUSA-N (3R)-3-[4-(dimethylcarbamoyl)-3-fluorophenyl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=C(F)C=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 AABSHUYBOADMEL-OAQYLSRUSA-N 0.000 claims 1
- JKZIDGVTCMWTAT-JOCHJYFZSA-N (3R)-3-[4-(dimethylcarbamoyl)-3-fluorophenyl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=C(F)C=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 JKZIDGVTCMWTAT-JOCHJYFZSA-N 0.000 claims 1
- GMMYZPVASQTFFK-JOCHJYFZSA-N (3R)-3-[4-(dimethylcarbamoyl)phenyl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=CC=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 GMMYZPVASQTFFK-JOCHJYFZSA-N 0.000 claims 1
- VSDHMCYRFWUCLN-HSZRJFAPSA-N (3R)-3-[4-(dimethylcarbamoyl)phenyl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=CC=C(C=C1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 VSDHMCYRFWUCLN-HSZRJFAPSA-N 0.000 claims 1
- VSXGLLXIAOAFJK-HXUWFJFHSA-N (3R)-3-[4-fluoro-3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]-3-(2-methylpyrimidin-5-yl)propanoic acid Chemical compound FC=1C(=NN(C=1)[C@H](CC(=O)O)C=1C=NC(=NC=1)C)CCCC1=NC=2NCCCC=2C=C1 VSXGLLXIAOAFJK-HXUWFJFHSA-N 0.000 claims 1
- PMFSDJYOISLEPP-HXUWFJFHSA-N (3R)-3-[6-(dimethylamino)pyridin-3-yl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C1=CC=C(C=N1)[C@@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 PMFSDJYOISLEPP-HXUWFJFHSA-N 0.000 claims 1
- BADLBAKVUVGUCQ-OAQYLSRUSA-N (3R)-3-[6-(dimethylamino)pyridin-3-yl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C1=CC=C(C=N1)[C@@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 BADLBAKVUVGUCQ-OAQYLSRUSA-N 0.000 claims 1
- NILMFCZRJMTOOS-HSZRJFAPSA-N (3R)-3-quinolin-3-yl-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]triazol-2-yl]propanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@@H](CC(=O)O)N1N=CC(=N1)CCCC1=NC=2NCCCC=2C=C1 NILMFCZRJMTOOS-HSZRJFAPSA-N 0.000 claims 1
- XAEQBBHRFFMXHY-OAQYLSRUSA-N (3R)-3-quinoxalin-6-yl-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound N1=CC=NC2=CC(=CC=C12)[C@@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 XAEQBBHRFFMXHY-OAQYLSRUSA-N 0.000 claims 1
- ZBYRRNDJUHIXRU-SANMLTNESA-N (3S)-3-(1-benzyl-6-oxopyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@H](N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1)C1=CN(CC2=CC=CC=C2)C(=O)C=C1 ZBYRRNDJUHIXRU-SANMLTNESA-N 0.000 claims 1
- UANVLGXYBXOAKG-FQEVSTJZSA-N (3S)-3-(1-methyl-6-oxopyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound Cn1cc(ccc1=O)[C@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 UANVLGXYBXOAKG-FQEVSTJZSA-N 0.000 claims 1
- CNBKWJCVGKLONT-FQEVSTJZSA-N (3S)-3-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-7-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@@H](c1cnc2OCCOc2c1)n1ccc(CCCc2ccc3CCCNc3n2)n1 CNBKWJCVGKLONT-FQEVSTJZSA-N 0.000 claims 1
- JEWVDLUACRWTEW-FQEVSTJZSA-N (3S)-3-(2-ethoxypyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound CCOc1ncc(cn1)[C@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 JEWVDLUACRWTEW-FQEVSTJZSA-N 0.000 claims 1
- QMBVMQULMAFHDB-FQEVSTJZSA-N (3S)-3-(2-ethoxypyrimidin-5-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound C(C)OC1=NC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 QMBVMQULMAFHDB-FQEVSTJZSA-N 0.000 claims 1
- UBYJRGAFVQXRIU-IBGZPJMESA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ncc(cn1)[C@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 UBYJRGAFVQXRIU-IBGZPJMESA-N 0.000 claims 1
- CBEDCDMHOQWJRM-FQEVSTJZSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=C(C=C1)CCCC=1C=CC2=C(NCCCC2)N=1 CBEDCDMHOQWJRM-FQEVSTJZSA-N 0.000 claims 1
- YGUFEJBKMLSYAH-MJGOQNOKSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-[(2R)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=C(C=C1)CCC[C@H]1NC2=NC=CC=C2CC1 YGUFEJBKMLSYAH-MJGOQNOKSA-N 0.000 claims 1
- YGUFEJBKMLSYAH-HKUYNNGSSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[3-[3-[(2S)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ncc(cn1)[C@H](CC(O)=O)n1ccc(CCC[C@H]2CCc3cccnc3N2)n1 YGUFEJBKMLSYAH-HKUYNNGSSA-N 0.000 claims 1
- DAJVJLDTALOMRU-SFHVURJKSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ncc(cn1)[C@H](CC(O)=O)c1nc(CCCc2ccc3CCCNc3n2)cs1 DAJVJLDTALOMRU-SFHVURJKSA-N 0.000 claims 1
- JEJVFRHYKOLBOR-SFHVURJKSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]triazol-2-yl]propanoic acid Chemical compound COc1ncc(cn1)[C@H](CC(O)=O)n1ncc(CCCc2ccc3CCCNc3n2)n1 JEJVFRHYKOLBOR-SFHVURJKSA-N 0.000 claims 1
- IFPMYGLSHXXRFZ-IBGZPJMESA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 IFPMYGLSHXXRFZ-IBGZPJMESA-N 0.000 claims 1
- ZKJMYZGFBDUOAC-FQEVSTJZSA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 ZKJMYZGFBDUOAC-FQEVSTJZSA-N 0.000 claims 1
- YZJQEJHDCYMNMO-NRFANRHFSA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=C(C=C1)CCCC=1C=CC2=C(NCCCC2)N=1 YZJQEJHDCYMNMO-NRFANRHFSA-N 0.000 claims 1
- QUAIYNWNKTYYGL-QUCCMNQESA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[3-[3-[(2R)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound Cc1ncc(cn1)[C@H](CC(O)=O)n1ccc(CCC[C@@H]2CCc3cccnc3N2)n1 QUAIYNWNKTYYGL-QUCCMNQESA-N 0.000 claims 1
- QUAIYNWNKTYYGL-ICSRJNTNSA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[3-[3-[(2S)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](CC(O)=O)N1C=CC(CCC[C@H]2CCC3=CC=CN=C3N2)=N1 QUAIYNWNKTYYGL-ICSRJNTNSA-N 0.000 claims 1
- BCBRXDHPNAOLSW-IBGZPJMESA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 BCBRXDHPNAOLSW-IBGZPJMESA-N 0.000 claims 1
- WKRYSVJHDZTTJT-SFHVURJKSA-N (3S)-3-(2-oxo-1H-pyrimidin-5-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@H](N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1)C1=CN=C(O)N=C1 WKRYSVJHDZTTJT-SFHVURJKSA-N 0.000 claims 1
- KOZUTVCXHZESNP-FQEVSTJZSA-N (3S)-3-(3,4-dimethoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COc1ccc(cc1OC)[C@H](CC(O)=O)c1nc(CCCc2ccc3CCCNc3n2)cs1 KOZUTVCXHZESNP-FQEVSTJZSA-N 0.000 claims 1
- GDBNGKQEPUAMCI-NRFANRHFSA-N (3S)-3-(3,4-dimethoxyphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC=1C=C(C=CC=1OC)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 GDBNGKQEPUAMCI-NRFANRHFSA-N 0.000 claims 1
- HVDGUXVTAKZNCH-IBGZPJMESA-N (3S)-3-(3,5-dimethylpyrazol-1-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=NN([C@@H](CC(O)=O)C2=NC(CCCC3=CC=C4CCCNC4=N3)=CS2)C(C)=C1 HVDGUXVTAKZNCH-IBGZPJMESA-N 0.000 claims 1
- QGFWAHQPFIYBOM-NRFANRHFSA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[1-methyl-4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]imidazol-2-yl]propanoic acid Chemical compound FC=1C=C(C=CC=1OC)[C@H](CC(=O)O)C=1N(C=C(N=1)CCCCC1=NC=2NCCCC=2C=C1)C QGFWAHQPFIYBOM-NRFANRHFSA-N 0.000 claims 1
- ROKVLOGQHMXEJC-NRFANRHFSA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[1-methyl-5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]imidazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC=C(CCCCC2=CC=C3CCCNC3=N2)N1C ROKVLOGQHMXEJC-NRFANRHFSA-N 0.000 claims 1
- IRRAOOUFBQNPFO-SFHVURJKSA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[2-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-4-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=CSC(CCCC2=CC=C3CCCNC3=N2)=N1 IRRAOOUFBQNPFO-SFHVURJKSA-N 0.000 claims 1
- DOUMICIFYPBLQH-IBGZPJMESA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-oxazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CO1 DOUMICIFYPBLQH-IBGZPJMESA-N 0.000 claims 1
- ZDRWXUHIAQJLBM-IBGZPJMESA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 ZDRWXUHIAQJLBM-IBGZPJMESA-N 0.000 claims 1
- YEVCJKDMMKTHNO-FQEVSTJZSA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]triazol-2-yl]propanoic acid Chemical compound COc1ccc(cc1F)[C@H](CC(O)=O)n1ncc(CCCc2ccc3CCCNc3n2)n1 YEVCJKDMMKTHNO-FQEVSTJZSA-N 0.000 claims 1
- YXDUBNYLAAIZFB-FQEVSTJZSA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 YXDUBNYLAAIZFB-FQEVSTJZSA-N 0.000 claims 1
- QMQQAYAICVRTEQ-IBGZPJMESA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC=C(CCCC2=CC=C3CCCNC3=N2)S1 QMQQAYAICVRTEQ-IBGZPJMESA-N 0.000 claims 1
- ZPSSHXXWTPHCDU-IBGZPJMESA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1H-pyrazol-3-yl]propanoic acid Chemical compound COc1ccc(cc1F)[C@H](CC(O)=O)c1cc(CCCc2ccc3CCCNc3n2)[nH]n1 ZPSSHXXWTPHCDU-IBGZPJMESA-N 0.000 claims 1
- AATLLCJAZYCLSY-FQEVSTJZSA-N (3S)-3-(3-fluoro-4-methoxyphenyl)-3-[5-methyl-4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-oxazol-2-yl]propanoic acid Chemical compound COC1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=C(C)O1 AATLLCJAZYCLSY-FQEVSTJZSA-N 0.000 claims 1
- LVZQWYRNDVVBAH-VWLOTQADSA-N (3S)-3-(3-morpholin-4-ylphenyl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound OC(=O)C[C@H](c1nc(CCCCc2ccc3CCCNc3n2)cs1)c1cccc(c1)N1CCOCC1 LVZQWYRNDVVBAH-VWLOTQADSA-N 0.000 claims 1
- XIVCRSBEVGNWMB-NRFANRHFSA-N (3S)-3-(5-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=CN=CC(=C1)[C@H](CC(O)=O)N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1 XIVCRSBEVGNWMB-NRFANRHFSA-N 0.000 claims 1
- DDEPDVDAXZTTNI-NRFANRHFSA-N (3S)-3-(5-methylpyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound CC=1C=C(C=NC=1)[C@H](CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 DDEPDVDAXZTTNI-NRFANRHFSA-N 0.000 claims 1
- REHWTMUCNPCVOK-FQEVSTJZSA-N (3S)-3-(5-methylpyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CC1=CN=CC(=C1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 REHWTMUCNPCVOK-FQEVSTJZSA-N 0.000 claims 1
- IABHYNPYOQIKNL-FQEVSTJZSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[1-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-4-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@H](CC(O)=O)c1cnn(CCCc2ccc3CCCNc3n2)c1 IABHYNPYOQIKNL-FQEVSTJZSA-N 0.000 claims 1
- QRQPTVHWXMVXDU-NRFANRHFSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[1-methyl-5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]imidazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1N(C(=CN=1)CCCCC1=NC=2NCCCC=2C=C1)C QRQPTVHWXMVXDU-NRFANRHFSA-N 0.000 claims 1
- VXWFWYADNINHES-FQEVSTJZSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ccc(cn1)[C@H](CC(O)=O)n1ccc(CCCc2ccc3CCCNc3n2)n1 VXWFWYADNINHES-FQEVSTJZSA-N 0.000 claims 1
- ZVPFAVSYSYIDJI-LFABVHOISA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrrolidin-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(O)=O)N1CCC(CCCC2=CC=C3CCCNC3=N2)C1 ZVPFAVSYSYIDJI-LFABVHOISA-N 0.000 claims 1
- MBIIFYIIXDIURN-NRFANRHFSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(O)=O)N1C=CC(CCCC2=CC=C3CCCCNC3=N2)=N1 MBIIFYIIXDIURN-NRFANRHFSA-N 0.000 claims 1
- WWVUBEGMDOTPPR-IBGZPJMESA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 WWVUBEGMDOTPPR-IBGZPJMESA-N 0.000 claims 1
- MOSAYWZXWIYPJY-IBGZPJMESA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]triazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(O)=O)N1N=CC(CCCC2=CC=C3CCCNC3=N2)=N1 MOSAYWZXWIYPJY-IBGZPJMESA-N 0.000 claims 1
- CGAASNMVFHAXRP-FQEVSTJZSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 CGAASNMVFHAXRP-FQEVSTJZSA-N 0.000 claims 1
- SXFILBGBIGGRAC-IBGZPJMESA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC(=CN=1)CCCC1=NC=2NCCCC=2C=C1 SXFILBGBIGGRAC-IBGZPJMESA-N 0.000 claims 1
- KWQAOJZTPSJWFI-FQEVSTJZSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[5-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC(=CN=1)CCCCC1=NC=2NCCCC=2C=C1 KWQAOJZTPSJWFI-FQEVSTJZSA-N 0.000 claims 1
- VUCPJDQRPNKODR-IBGZPJMESA-N (3S)-3-(6-oxo-1H-pyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@@H](c1ccc(=O)[nH]c1)n1ccc(CCCc2ccc3CCCNc3n2)n1 VUCPJDQRPNKODR-IBGZPJMESA-N 0.000 claims 1
- ZGCLOBSDNFKPOK-SANMLTNESA-N (3S)-3-(6-phenylmethoxypyridin-3-yl)-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@H](N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1)C1=CC=C(OCC2=CC=CC=C2)N=C1 ZGCLOBSDNFKPOK-SANMLTNESA-N 0.000 claims 1
- CGNMIYRIWLHATI-QHCPKHFHSA-N (3S)-3-[1-(cyclopropylmethyl)-6-oxopyridin-3-yl]-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@H](N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1)C1=CN(CC2CC2)C(=O)C=C1 CGNMIYRIWLHATI-QHCPKHFHSA-N 0.000 claims 1
- KZDCPPDMQHBFFY-QFIPXVFZSA-N (3S)-3-[3-(dimethylcarbamoyl)phenyl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)c1cccc(c1)[C@H](CC(O)=O)c1nc(CCCc2ccc3CCCNc3n2)cs1 KZDCPPDMQHBFFY-QFIPXVFZSA-N 0.000 claims 1
- GUDIIKKLVLPESU-QHCPKHFHSA-N (3S)-3-[3-(dimethylcarbamoyl)phenyl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=CC=CC(=C1)[C@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 GUDIIKKLVLPESU-QHCPKHFHSA-N 0.000 claims 1
- AABSHUYBOADMEL-NRFANRHFSA-N (3S)-3-[4-(dimethylcarbamoyl)-3-fluorophenyl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 AABSHUYBOADMEL-NRFANRHFSA-N 0.000 claims 1
- JKZIDGVTCMWTAT-QFIPXVFZSA-N (3S)-3-[4-(dimethylcarbamoyl)-3-fluorophenyl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=C(F)C=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 JKZIDGVTCMWTAT-QFIPXVFZSA-N 0.000 claims 1
- GMMYZPVASQTFFK-QFIPXVFZSA-N (3S)-3-[4-(dimethylcarbamoyl)phenyl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=CC=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCC2=CC=C3CCCNC3=N2)=CS1 GMMYZPVASQTFFK-QFIPXVFZSA-N 0.000 claims 1
- VSDHMCYRFWUCLN-QHCPKHFHSA-N (3S)-3-[4-(dimethylcarbamoyl)phenyl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C(=O)C1=CC=C(C=C1)[C@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 VSDHMCYRFWUCLN-QHCPKHFHSA-N 0.000 claims 1
- SUMPEFHMPYZTQH-QHCPKHFHSA-N (3S)-3-[6-(cyclopropylmethoxy)pyridin-3-yl]-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)C[C@H](N1C=CC(CCCC2=CC=C3CCCNC3=N2)=N1)C1=CC=C(OCC2CC2)N=C1 SUMPEFHMPYZTQH-QHCPKHFHSA-N 0.000 claims 1
- PMFSDJYOISLEPP-FQEVSTJZSA-N (3S)-3-[6-(dimethylamino)pyridin-3-yl]-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C1=CC=C(C=N1)[C@H](CC(=O)O)C=1SC=C(N=1)CCCC1=NC=2NCCCC=2C=C1)C PMFSDJYOISLEPP-FQEVSTJZSA-N 0.000 claims 1
- BADLBAKVUVGUCQ-NRFANRHFSA-N (3S)-3-[6-(dimethylamino)pyridin-3-yl]-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound CN(C)C1=CC=C(C=N1)[C@H](CC(O)=O)C1=NC(CCCCC2=CC=C3CCCNC3=N2)=CS1 BADLBAKVUVGUCQ-NRFANRHFSA-N 0.000 claims 1
- NILMFCZRJMTOOS-QHCPKHFHSA-N (3S)-3-quinolin-3-yl-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]triazol-2-yl]propanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@H](CC(=O)O)N1N=CC(=N1)CCCC1=NC=2NCCCC=2C=C1 NILMFCZRJMTOOS-QHCPKHFHSA-N 0.000 claims 1
- XAEQBBHRFFMXHY-NRFANRHFSA-N (3S)-3-quinoxalin-6-yl-3-[4-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-thiazol-2-yl]propanoic acid Chemical compound N1=CC=NC2=CC(=CC=C12)[C@H](CC(=O)O)C=1SC=C(N=1)CCCCC1=NC=2NCCCC=2C=C1 XAEQBBHRFFMXHY-NRFANRHFSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- JUEJISWKTFLIGZ-DUSLRRAJSA-N 3-(2-methoxypyrimidin-5-yl)-3-[5-[3-[(2R)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)C(CC(=O)O)N1N=CC=C1CCC[C@H]1NC2=NC=CC=C2CC1 JUEJISWKTFLIGZ-DUSLRRAJSA-N 0.000 claims 1
- JUEJISWKTFLIGZ-KKFHFHRHSA-N 3-(2-methoxypyrimidin-5-yl)-3-[5-[3-[(2S)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound COc1ncc(cn1)C(CC(O)=O)n1nccc1CCC[C@H]1CCc2cccnc2N1 JUEJISWKTFLIGZ-KKFHFHRHSA-N 0.000 claims 1
- PBWFOTQLLPUBFH-QSVWIEALSA-N 3-(2-methylpyrimidin-5-yl)-3-[5-[3-[(2R)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound Cc1ncc(cn1)C(CC(O)=O)n1nccc1CCC[C@@H]1CCc2cccnc2N1 PBWFOTQLLPUBFH-QSVWIEALSA-N 0.000 claims 1
- PBWFOTQLLPUBFH-LROBGIAVSA-N 3-(2-methylpyrimidin-5-yl)-3-[5-[3-[(2S)-1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl]propyl]pyrazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)C(CC(O)=O)N1N=CC=C1CCC[C@H]1CCC2=CC=CN=C2N1 PBWFOTQLLPUBFH-LROBGIAVSA-N 0.000 claims 1
- PISFUPDRJUNJMG-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-3-[1-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]pyrazol-4-yl]propanoic acid Chemical compound FC=1C=C(C=CC=1OC)C(CC(=O)O)C=1C=NN(C=1)CCCCC1=NC=2NCCCC=2C=C1 PISFUPDRJUNJMG-UHFFFAOYSA-N 0.000 claims 1
- WETNDFFONPZIGS-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[1-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-3-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(O)=O)C1=NN(CCCC2=CC=C3CCCNC3=N2)C=C1 WETNDFFONPZIGS-UHFFFAOYSA-N 0.000 claims 1
- ZVUWHFQRZDKPAU-UHFFFAOYSA-N 3-[5-(2-methoxyethoxy)pyridin-3-yl]-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound COCCOC=1C=C(C=NC=1)C(CC(=O)O)N1N=C(C=C1)CCCC1=NC=2NCCCC=2C=C1 ZVUWHFQRZDKPAU-UHFFFAOYSA-N 0.000 claims 1
- MFXILPMGYBKQFH-UHFFFAOYSA-N 3-pyrimidin-5-yl-3-[3-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazol-1-yl]propanoic acid Chemical compound OC(=O)CC(c1cncnc1)n1ccc(CCCc2ccc3CCCNc3n2)n1 MFXILPMGYBKQFH-UHFFFAOYSA-N 0.000 claims 1
- 239000012453 solvate Substances 0.000 abstract description 23
- 239000005557 antagonist Substances 0.000 abstract description 5
- 230000008482 dysregulation Effects 0.000 abstract description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 220
- 241000282414 Homo sapiens Species 0.000 description 187
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 158
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| PCT/US2017/060376 WO2018089353A1 (en) | 2016-11-08 | 2017-11-07 | 3-substituted propionic acids as alpha v integrin inhibitors |
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| CN109996541A (zh) | 2016-09-07 | 2019-07-09 | 普利安特治疗公司 | N-酰基氨基酸化合物及其使用方法 |
| EA038164B1 (ru) * | 2016-11-08 | 2021-07-16 | Бристол-Маерс Сквибб Компани | 3-замещенные пропановые кислоты в качестве ингибиторов интегрина v |
| WO2018089355A1 (en) * | 2016-11-08 | 2018-05-17 | Bristol-Myers Squibb Company | Cyclobutane- and azetidine-containing mono and spirocyclic compounds as alpha v integrin inhibitors |
| WO2018089358A1 (en) * | 2016-11-08 | 2018-05-17 | Bristol-Myers Squibb Company | Azole amides and amines as alpha v integrin inhibitors |
| KR20190100232A (ko) | 2016-12-29 | 2019-08-28 | 세인트 루이스 유니버시티 | 인테그린 길항제 |
| EP4147698A1 (en) | 2017-02-28 | 2023-03-15 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| JP7092784B2 (ja) | 2017-02-28 | 2022-06-28 | モーフィック セラピューティック，インコーポレイテッド | αｖβ６インテグリン阻害剤 |
| JP2021535141A (ja) | 2018-08-29 | 2021-12-16 | モーフィック セラピューティック，インコーポレイテッド | αｖβ６インテグリンの阻害 |
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| CN112969504B (zh) | 2018-10-30 | 2024-04-09 | 吉利德科学公司 | 用于抑制α4β7整合素的化合物 |
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| CN109824495B (zh) * | 2019-02-02 | 2022-12-09 | 盐城师范学院 | 一种新型偶联反应在制备碳-碳键结构化合物中的应用 |
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| WO2011059839A1 (en) | 2009-10-29 | 2011-05-19 | Sirtris Pharmaceuticals, Inc. | Bicyclic pyridines and analogs as sirtuin modulators |
| ITFI20100019A1 (it) | 2010-02-12 | 2011-08-13 | Univ Firenze | Inibitori peptidomimetici di integrine basati sull'1,2,3-triazolo per la diagnosi e terapia dei tumori. |
| GB201305668D0 (en) | 2013-03-28 | 2013-05-15 | Glaxosmithkline Ip Dev Ltd | Avs6 Integrin Antagonists |
| TWI667233B (zh) | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| GB201417011D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417002D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| GB201417018D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417094D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| TWI736529B (zh) | 2015-02-19 | 2021-08-21 | 美商賽氟洛生命科學公司 | 氟化之四氫啶基壬酸衍生物及其用途 |
| JP2018515424A (ja) * | 2015-03-10 | 2018-06-14 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 抗アルファｖベータ１インテグリン阻害剤及び使用方法 |
| EA038164B1 (ru) * | 2016-11-08 | 2021-07-16 | Бристол-Маерс Сквибб Компани | 3-замещенные пропановые кислоты в качестве ингибиторов интегрина v |
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