CA3042714A1 - Indazole derivatives as a .alpha.v integrin antagonists - Google Patents
Indazole derivatives as a .alpha.v integrin antagonists Download PDFInfo
- Publication number
- CA3042714A1 CA3042714A1 CA3042714A CA3042714A CA3042714A1 CA 3042714 A1 CA3042714 A1 CA 3042714A1 CA 3042714 A CA3042714 A CA 3042714A CA 3042714 A CA3042714 A CA 3042714A CA 3042714 A1 CA3042714 A1 CA 3042714A1
- Authority
- CA
- Canada
- Prior art keywords
- naphthyridin
- tetrahydro
- indazol
- propanoic acid
- ethoxy
- 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.)
- Abandoned
Links
- 102000006495 integrins Human genes 0.000 title abstract description 29
- 108010044426 integrins Proteins 0.000 title abstract description 29
- 239000005557 antagonist Substances 0.000 title abstract description 7
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title description 2
- 241000352333 Amegilla alpha Species 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 233
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 208000035475 disorder Diseases 0.000 claims abstract description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 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
- -1 cyano, hydroxyl Chemical group 0.000 claims description 139
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 91
- 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 90
- 235000019260 propionic acid Nutrition 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 75
- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 239000001257 hydrogen Substances 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 125000001188 haloalkyl group Chemical group 0.000 claims description 36
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 34
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 125000004043 oxo group Chemical group O=* 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 25
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000004475 Arginine Substances 0.000 claims description 17
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 13
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 13
- 229940124530 sulfonamide Drugs 0.000 claims description 13
- 150000003456 sulfonamides Chemical class 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 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
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 9
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 210000004185 liver Anatomy 0.000 claims description 7
- 201000009594 Systemic Scleroderma Diseases 0.000 claims description 6
- 206010042953 Systemic sclerosis Diseases 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000003627 8 membered carbocyclic group Chemical group 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
- 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 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- HKDFLJPTLIDIRY-UHFFFAOYSA-N 2-(phenylmethoxycarbonylamino)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(C1=CC=CC=C1)OC(=O)NC(C(=O)O)CN1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 HKDFLJPTLIDIRY-UHFFFAOYSA-N 0.000 claims description 2
- STMJTKHUFDVBKN-UHFFFAOYSA-N 3-phenyl-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propoxy]indazol-1-yl]propanoic acid Chemical compound C1(=CC=CC=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCCC1=NC=2NCCCC=2C=C1 STMJTKHUFDVBKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 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
- 125000004744 butyloxycarbonyl group Chemical group 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
- 230000002500 effect on skin Effects 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
- 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
- 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
- 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
- 210000001685 thyroid gland Anatomy 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 5
- OKIOBRYXBIOAJA-UHFFFAOYSA-N 3-quinolin-3-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OKIOBRYXBIOAJA-UHFFFAOYSA-N 0.000 claims 2
- GTCYHEBCPBFIIH-DEOSSOPVSA-N (2S)-2-(phenylmethoxycarbonylamino)-3-[5-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-ylmethoxy)indazol-2-yl]propanoic acid Chemical compound C(C1=CC=CC=C1)OC(=O)N[C@H](C(=O)O)CN1N=C2C=CC(=CC2=C1)OCC1=NC=2NCCCC=2C=C1 GTCYHEBCPBFIIH-DEOSSOPVSA-N 0.000 claims 1
- RPMSIYXXTCLZRK-HSZRJFAPSA-N (3R)-3-(2-ethoxypyrimidin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(C)OC1=NC=C(C=N1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 RPMSIYXXTCLZRK-HSZRJFAPSA-N 0.000 claims 1
- IEFLMLMYJYMEMG-HSZRJFAPSA-N (3R)-3-(2-methylpyrimidin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 IEFLMLMYJYMEMG-HSZRJFAPSA-N 0.000 claims 1
- IEVJUXBVPRRYJM-VOIUYBSRSA-N (3R)-3-(2-methylpyrimidin-5-yl)-3-[5-[2-[(7R)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]ethoxy]indazol-1-yl]propanoic acid Chemical compound C[C@@H]1CCC=2C=CC(=NC=2N1)CCOC=1C=C2C=NN(C2=CC=1)[C@H](CC(=O)O)C=1C=NC(=NC=1)C IEVJUXBVPRRYJM-VOIUYBSRSA-N 0.000 claims 1
- IEVJUXBVPRRYJM-UPCLLVRISA-N (3R)-3-(2-methylpyrimidin-5-yl)-3-[5-[2-[(7S)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]ethoxy]indazol-1-yl]propanoic acid Chemical compound C[C@H]1CCC=2C=CC(=NC=2N1)CCOC=1C=C2C=NN(C2=CC=1)[C@H](CC(=O)O)C=1C=NC(=NC=1)C IEVJUXBVPRRYJM-UPCLLVRISA-N 0.000 claims 1
- VDBKKEGWDIFKBU-XMMPIXPASA-N (3R)-3-(5-methylsulfonylpyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CS(=O)(=O)C=1C=C(C=NC=1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 VDBKKEGWDIFKBU-XMMPIXPASA-N 0.000 claims 1
- DXMOTFLMGAQNII-HSZRJFAPSA-N (3R)-3-(6-methoxypyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DXMOTFLMGAQNII-HSZRJFAPSA-N 0.000 claims 1
- DMSBKSXXSGRLQF-HHHXNRCGSA-N (3R)-3-[3-(2-oxopyrrolidin-1-yl)phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O=C1N(CCC1)C=1C=C(C=CC=1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DMSBKSXXSGRLQF-HHHXNRCGSA-N 0.000 claims 1
- XIGPNPDVLUFGKH-AREMUKBSSA-N (3R)-3-[3-(dimethylcarbamoyl)phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN(C(=O)C=1C=C(C=CC=1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C XIGPNPDVLUFGKH-AREMUKBSSA-N 0.000 claims 1
- OFYNULKNCZVTMF-RUZDIDTESA-N (3R)-3-[5-(1,3-dioxolan-2-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1C(OCC1)C=1C=C(C=NC=1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OFYNULKNCZVTMF-RUZDIDTESA-N 0.000 claims 1
- OKNQMULFPFESAF-RUZDIDTESA-N (3R)-3-[5-(2-hydroxypropan-2-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound OC(C)(C)C=1C=C(C=NC=1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OKNQMULFPFESAF-RUZDIDTESA-N 0.000 claims 1
- TXGWYHIXFKKFCJ-AREMUKBSSA-N (3R)-3-[5-(2-oxopyrrolidin-1-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O=C1N(CCC1)C=1C=C(C=NC=1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 TXGWYHIXFKKFCJ-AREMUKBSSA-N 0.000 claims 1
- LTMLALWUZPSFDF-XMMPIXPASA-N (3R)-3-[5-(hydroxymethyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound OCC=1C=C(C=NC=1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 LTMLALWUZPSFDF-XMMPIXPASA-N 0.000 claims 1
- IKIVIELJPRVCGD-RUZDIDTESA-N (3R)-3-[5-[(methoxycarbonylamino)methyl]pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC(=O)NCC=1C=C(C=NC=1)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 IKIVIELJPRVCGD-RUZDIDTESA-N 0.000 claims 1
- IRBNGLACBFFCAF-OAQYLSRUSA-N (3R)-3-[5-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)ethoxy]indazol-1-yl]-3-(6-methoxypyridin-3-yl)propanoic acid Chemical compound O1C2=C(NCC1)N=C(C=C2)CCOC=1C=C2C=NN(C2=CC=1)[C@H](CC(=O)O)C=1C=NC(=CC=1)OC IRBNGLACBFFCAF-OAQYLSRUSA-N 0.000 claims 1
- PUDHAUCMWPABIY-XMMPIXPASA-N (3R)-3-pyrido[2,3-b]pyrazin-7-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C2C(=NC=C1)N=CC(=C2)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 PUDHAUCMWPABIY-XMMPIXPASA-N 0.000 claims 1
- ZHYATRSIDLIEQO-AREMUKBSSA-N (3R)-3-quinoxalin-2-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C(C=NC2=CC=CC=C12)[C@@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 ZHYATRSIDLIEQO-AREMUKBSSA-N 0.000 claims 1
- RPMSIYXXTCLZRK-QHCPKHFHSA-N (3S)-3-(2-ethoxypyrimidin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(C)OC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 RPMSIYXXTCLZRK-QHCPKHFHSA-N 0.000 claims 1
- FKXIWHTZSAAXHT-QFIPXVFZSA-N (3S)-3-(2-methoxypyrimidin-5-yl)-3-[6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-2-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CCC1=NC=2NCCCC=2C=C1 FKXIWHTZSAAXHT-QFIPXVFZSA-N 0.000 claims 1
- IEFLMLMYJYMEMG-QHCPKHFHSA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 IEFLMLMYJYMEMG-QHCPKHFHSA-N 0.000 claims 1
- IEVJUXBVPRRYJM-GYCJOSAFSA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[5-[2-[(7R)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]ethoxy]indazol-1-yl]propanoic acid Chemical compound C[C@@H]1CCC=2C=CC(=NC=2N1)CCOC=1C=C2C=NN(C2=CC=1)[C@@H](CC(=O)O)C=1C=NC(=NC=1)C IEVJUXBVPRRYJM-GYCJOSAFSA-N 0.000 claims 1
- IEVJUXBVPRRYJM-FYSMJZIKSA-N (3S)-3-(2-methylpyrimidin-5-yl)-3-[5-[2-[(7S)-7-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl]ethoxy]indazol-1-yl]propanoic acid Chemical compound C[C@H]1CCC=2C=CC(=NC=2N1)CCOC=1C=C2C=NN(C2=CC=1)[C@@H](CC(=O)O)C=1C=NC(=NC=1)C IEVJUXBVPRRYJM-FYSMJZIKSA-N 0.000 claims 1
- VDBKKEGWDIFKBU-DEOSSOPVSA-N (3S)-3-(5-methylsulfonylpyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CS(=O)(=O)C=1C=C(C=NC=1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 VDBKKEGWDIFKBU-DEOSSOPVSA-N 0.000 claims 1
- DXMOTFLMGAQNII-QHCPKHFHSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DXMOTFLMGAQNII-QHCPKHFHSA-N 0.000 claims 1
- IBJMZQSYNARXOG-QHCPKHFHSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=CC(=CC2=C1)OCCC1=NC=2NCCCC=2C=C1 IBJMZQSYNARXOG-QHCPKHFHSA-N 0.000 claims 1
- YPOVJGJYFREUAA-QHCPKHFHSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=CC(=CC2=C1)CCC1=NC=2NCCCC=2C=C1 YPOVJGJYFREUAA-QHCPKHFHSA-N 0.000 claims 1
- MSEZJXWRCPWFRD-DEOSSOPVSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=CC(=CC2=C1)CCCC1=NC=2NCCCC=2C=C1 MSEZJXWRCPWFRD-DEOSSOPVSA-N 0.000 claims 1
- SEIOZNXVMKEXMV-QHCPKHFHSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[6-[(2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl]indazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CC=1C(=NC=2NCCCC=2C=1)C SEIOZNXVMKEXMV-QHCPKHFHSA-N 0.000 claims 1
- IKRDDHNDNMJKIW-DEOSSOPVSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[6-[2-(2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethyl]indazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CCC=1C(=NC=2NCCCC=2C=1)C IKRDDHNDNMJKIW-DEOSSOPVSA-N 0.000 claims 1
- BVLSVFVVONTYJD-QHCPKHFHSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)OCCC1=NC=2NCCCC=2C=C1 BVLSVFVVONTYJD-QHCPKHFHSA-N 0.000 claims 1
- QCJCXKWNJRTCGA-QHCPKHFHSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CCC1=NC=2NCCCC=2C=C1 QCJCXKWNJRTCGA-QHCPKHFHSA-N 0.000 claims 1
- MYPIWCRREWLBQK-DEOSSOPVSA-N (3S)-3-(6-methoxypyridin-3-yl)-3-[6-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-2-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CCCC1=NC=2NCCCC=2C=C1 MYPIWCRREWLBQK-DEOSSOPVSA-N 0.000 claims 1
- DMSBKSXXSGRLQF-MHZLTWQESA-N (3S)-3-[3-(2-oxopyrrolidin-1-yl)phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O=C1N(CCC1)C=1C=C(C=CC=1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DMSBKSXXSGRLQF-MHZLTWQESA-N 0.000 claims 1
- XIGPNPDVLUFGKH-SANMLTNESA-N (3S)-3-[3-(dimethylcarbamoyl)phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN(C(=O)C=1C=C(C=CC=1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C XIGPNPDVLUFGKH-SANMLTNESA-N 0.000 claims 1
- OFYNULKNCZVTMF-VWLOTQADSA-N (3S)-3-[5-(1,3-dioxolan-2-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1C(OCC1)C=1C=C(C=NC=1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OFYNULKNCZVTMF-VWLOTQADSA-N 0.000 claims 1
- TXGWYHIXFKKFCJ-SANMLTNESA-N (3S)-3-[5-(2-oxopyrrolidin-1-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O=C1N(CCC1)C=1C=C(C=NC=1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 TXGWYHIXFKKFCJ-SANMLTNESA-N 0.000 claims 1
- LTMLALWUZPSFDF-DEOSSOPVSA-N (3S)-3-[5-(hydroxymethyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound OCC=1C=C(C=NC=1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 LTMLALWUZPSFDF-DEOSSOPVSA-N 0.000 claims 1
- IKIVIELJPRVCGD-VWLOTQADSA-N (3S)-3-[5-[(methoxycarbonylamino)methyl]pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC(=O)NCC=1C=C(C=NC=1)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 IKIVIELJPRVCGD-VWLOTQADSA-N 0.000 claims 1
- IRBNGLACBFFCAF-NRFANRHFSA-N (3S)-3-[5-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)ethoxy]indazol-1-yl]-3-(6-methoxypyridin-3-yl)propanoic acid Chemical compound O1C2=C(NCC1)N=C(C=C2)CCOC=1C=C2C=NN(C2=CC=1)[C@@H](CC(=O)O)C=1C=NC(=CC=1)OC IRBNGLACBFFCAF-NRFANRHFSA-N 0.000 claims 1
- LNUIWROARKNGHL-MHZLTWQESA-N (3S)-3-[6-[(2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl]indazol-2-yl]-3-quinolin-3-ylpropanoic acid Chemical compound CC1=NC=2NCCCC=2C=C1CC=1C=CC2=CN(N=C2C=1)[C@@H](CC(=O)O)C=1C=NC2=CC=CC=C2C=1 LNUIWROARKNGHL-MHZLTWQESA-N 0.000 claims 1
- KRFCJODPBYWVKO-WKDCXCOVSA-N (3S)-3-quinolin-3-yl-3-[6-[2-(1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-2-yl]propanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CCC1NC2=NC=CC=C2CC1 KRFCJODPBYWVKO-WKDCXCOVSA-N 0.000 claims 1
- SBTKBLUWVQNIKH-MHZLTWQESA-N (3S)-3-quinolin-3-yl-3-[6-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-2-yl]propanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CCC1=NC=2NCCCC=2C=C1 SBTKBLUWVQNIKH-MHZLTWQESA-N 0.000 claims 1
- QAAGTQSOGRHDQE-NMXAJACMSA-N (3S)-3-quinolin-3-yl-3-[6-[3-(1,2,3,4-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-2-yl]propanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CCCC1NC2=NC=CC=C2CC1 QAAGTQSOGRHDQE-NMXAJACMSA-N 0.000 claims 1
- LBJKQHRCJJEDJK-NDEPHWFRSA-N (3S)-3-quinolin-3-yl-3-[6-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-2-yl]propanoic acid Chemical compound N1=CC(=CC2=CC=CC=C12)[C@H](CC(=O)O)N1N=C2C=C(C=CC2=C1)CCCC1=NC=2NCCCC=2C=C1 LBJKQHRCJJEDJK-NDEPHWFRSA-N 0.000 claims 1
- ZHYATRSIDLIEQO-SANMLTNESA-N (3S)-3-quinoxalin-2-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C(C=NC2=CC=CC=C12)[C@H](CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 ZHYATRSIDLIEQO-SANMLTNESA-N 0.000 claims 1
- HSELRENRQYYPCK-UHFFFAOYSA-N 2-[1-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]cyclopropyl]acetic acid Chemical compound N1=C(C=CC=2CCCNC1=2)CCOC=1C=C2C=NN(C2=CC=1)C1(CC1)CC(=O)O HSELRENRQYYPCK-UHFFFAOYSA-N 0.000 claims 1
- XXYULBPKRZIUFK-UHFFFAOYSA-N 3-(1,3-benzothiazol-6-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound S1C=NC2=C1C=C(C=C2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 XXYULBPKRZIUFK-UHFFFAOYSA-N 0.000 claims 1
- QGIATSGZIDXPHR-UHFFFAOYSA-N 3-(1,8-naphthyridin-2-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C(C=CC2=CC=CN=C12)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 QGIATSGZIDXPHR-UHFFFAOYSA-N 0.000 claims 1
- KGNAPRPMBDLDJJ-UHFFFAOYSA-N 3-(1,8-naphthyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=CC(=CC2=CC=CN=C12)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 KGNAPRPMBDLDJJ-UHFFFAOYSA-N 0.000 claims 1
- CAQOVHSOMOJYHF-UHFFFAOYSA-N 3-(1-methyl-2-oxopyridin-4-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1C(C=C(C=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)=O CAQOVHSOMOJYHF-UHFFFAOYSA-N 0.000 claims 1
- ZKURUCNKKIZWBE-UHFFFAOYSA-N 3-(1-methylimidazo[4,5-b]pyridin-6-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1C=NC2=NC=C(C=C21)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 ZKURUCNKKIZWBE-UHFFFAOYSA-N 0.000 claims 1
- RJQJOLGOPHKLFG-UHFFFAOYSA-N 3-(1-methylpyrazolo[3,4-b]pyridin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1N=CC=2C1=NC=C(C=2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 RJQJOLGOPHKLFG-UHFFFAOYSA-N 0.000 claims 1
- ICMQWGBRPJUPFL-UHFFFAOYSA-N 3-(1-methylpyrazolo[4,3-b]pyridin-6-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1N=CC2=NC=C(C=C21)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 ICMQWGBRPJUPFL-UHFFFAOYSA-N 0.000 claims 1
- ZDHPXUKSHNCHDZ-UHFFFAOYSA-N 3-(1-propylpyrazol-4-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(CC)N1N=CC(=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 ZDHPXUKSHNCHDZ-UHFFFAOYSA-N 0.000 claims 1
- NTRDSVUALLGMQR-UHFFFAOYSA-N 3-(1-pyridin-4-ylpyrazol-4-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=CC=C(C=C1)N1N=CC(=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 NTRDSVUALLGMQR-UHFFFAOYSA-N 0.000 claims 1
- BQJVTBGRPUGCCJ-UHFFFAOYSA-N 3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1N=CC=2C1=NC=C(C=2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 BQJVTBGRPUGCCJ-UHFFFAOYSA-N 0.000 claims 1
- KVZAZTYGJMIVGK-UHFFFAOYSA-N 3-(2,3-dihydro-1-benzofuran-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1CCC2=C1C=CC(=C2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 KVZAZTYGJMIVGK-UHFFFAOYSA-N 0.000 claims 1
- RPMSIYXXTCLZRK-UHFFFAOYSA-N 3-(2-ethoxypyrimidin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(C)OC1=NC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 RPMSIYXXTCLZRK-UHFFFAOYSA-N 0.000 claims 1
- XHOBSUQTPZREPF-UHFFFAOYSA-N 3-(2-methoxypyrimidin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC1=NC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 XHOBSUQTPZREPF-UHFFFAOYSA-N 0.000 claims 1
- XCUQZGBTJCSDEQ-UHFFFAOYSA-N 3-(2-methyl-1,3-benzothiazol-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CC=1SC2=C(N=1)C=C(C=C2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 XCUQZGBTJCSDEQ-UHFFFAOYSA-N 0.000 claims 1
- GPQGREXKGKUCER-UHFFFAOYSA-N 3-(2-methylpyrazolo[3,4-b]pyridin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1N=C2N=CC(=CC2=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 GPQGREXKGKUCER-UHFFFAOYSA-N 0.000 claims 1
- JQISWDRRXXBCJA-UHFFFAOYSA-N 3-(2-methylpyrazolo[4,3-b]pyridin-6-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1N=C2C(N=CC(=C2)C(CC(=O)O)N2N=CC3=CC(=CC=C23)OCCC2=NC=3NCCCC=3C=C2)=C1 JQISWDRRXXBCJA-UHFFFAOYSA-N 0.000 claims 1
- IEFLMLMYJYMEMG-UHFFFAOYSA-N 3-(2-methylpyrimidin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CC1=NC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 IEFLMLMYJYMEMG-UHFFFAOYSA-N 0.000 claims 1
- RFKRJFRHLLQYHE-UHFFFAOYSA-N 3-(2-morpholin-4-ylpyrimidin-5-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1CCN(CC1)C1=NC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 RFKRJFRHLLQYHE-UHFFFAOYSA-N 0.000 claims 1
- JGCSBOSYZVCQOH-UHFFFAOYSA-N 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1C2=C(NCC1)N=C(C=C2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 JGCSBOSYZVCQOH-UHFFFAOYSA-N 0.000 claims 1
- FKMGYZMPBIHKFW-UHFFFAOYSA-N 3-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1C2=C(NCC1)N=CC(=C2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 FKMGYZMPBIHKFW-UHFFFAOYSA-N 0.000 claims 1
- VVSKCIZJZJQFQR-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-3-[4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C(CC(=O)O)N1N=CC2=C(C=CC=C12)OCCC1=NC=2NCCCC=2C=C1 VVSKCIZJZJQFQR-UHFFFAOYSA-N 0.000 claims 1
- NKNNVSCSIJZXJB-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C(CC(=O)O)N1N=CC2=C(C=CC=C12)CCCC1=NC=2NCCCC=2C=C1 NKNNVSCSIJZXJB-UHFFFAOYSA-N 0.000 claims 1
- DVVAHSLSNWQJQY-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DVVAHSLSNWQJQY-UHFFFAOYSA-N 0.000 claims 1
- OPIRYWAINQEEHP-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C(CC(=O)O)N1N=CC2=CC(=CC=C12)CCC1=NC=2NCCCC=2C=C1 OPIRYWAINQEEHP-UHFFFAOYSA-N 0.000 claims 1
- NWNJQPRLFWFQHI-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-1-yl]propanoic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)C(CC(=O)O)N1N=CC2=CC(=CC=C12)CCCC1=NC=2NCCCC=2C=C1 NWNJQPRLFWFQHI-UHFFFAOYSA-N 0.000 claims 1
- MHKFCIIGKXYADZ-UHFFFAOYSA-N 3-(3-cyanophenyl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(#N)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 MHKFCIIGKXYADZ-UHFFFAOYSA-N 0.000 claims 1
- BZIRZFRTEKLIPT-UHFFFAOYSA-N 3-(3-fluoro-4-methoxyphenyl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound FC=1C=C(C=CC=1OC)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 BZIRZFRTEKLIPT-UHFFFAOYSA-N 0.000 claims 1
- QLWLYNGRKQWAKG-UHFFFAOYSA-N 3-(3-methylimidazo[4,5-b]pyridin-6-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1C=NC=2C1=NC=C(C=2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 QLWLYNGRKQWAKG-UHFFFAOYSA-N 0.000 claims 1
- JOBUPDOXJLDPFV-UHFFFAOYSA-N 3-(3-morpholin-4-ylphenyl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1CCN(CC1)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 JOBUPDOXJLDPFV-UHFFFAOYSA-N 0.000 claims 1
- WBBNQMAPQYJPDP-UHFFFAOYSA-N 3-(3-pyrrol-1-ylphenyl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1(C=CC=C1)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 WBBNQMAPQYJPDP-UHFFFAOYSA-N 0.000 claims 1
- QKCZEWBQGSLZDK-UHFFFAOYSA-N 3-(4,6-dimethylpyrimidin-2-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CC1=NC(=NC(=C1)C)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 QKCZEWBQGSLZDK-UHFFFAOYSA-N 0.000 claims 1
- LMFGACZJKSPAOE-UHFFFAOYSA-N 3-(4-phenoxyphenyl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 LMFGACZJKSPAOE-UHFFFAOYSA-N 0.000 claims 1
- MTKBXYWUGSKJKD-UHFFFAOYSA-N 3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C(C=CC=2CCCNC1=2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 MTKBXYWUGSKJKD-UHFFFAOYSA-N 0.000 claims 1
- LZNSCTVBCCNNSB-UHFFFAOYSA-N 3-(5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C(C=CC=2CCCNC1=2)CCOC=1C=C2C=NN(C2=CC=1)C(CC(=O)O)C=1C=NC=2NCCCC=2C=1 LZNSCTVBCCNNSB-UHFFFAOYSA-N 0.000 claims 1
- QKVSRGYSOTVNIK-UHFFFAOYSA-N 3-(5-chloropyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound ClC=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 QKVSRGYSOTVNIK-UHFFFAOYSA-N 0.000 claims 1
- WWJBLNXNICBYHK-UHFFFAOYSA-N 3-(5-cyclopropylpyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C1(CC1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 WWJBLNXNICBYHK-UHFFFAOYSA-N 0.000 claims 1
- BOPQEKRXULXHKQ-UHFFFAOYSA-N 3-(5-fluoro-6-methoxypyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound FC=1C=C(C=NC=1OC)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 BOPQEKRXULXHKQ-UHFFFAOYSA-N 0.000 claims 1
- XBTVXNPPMPBJDI-UHFFFAOYSA-N 3-(5-fluoropyridin-2-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound FC=1C=CC(=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 XBTVXNPPMPBJDI-UHFFFAOYSA-N 0.000 claims 1
- CYMMSYGHVRKYIX-UHFFFAOYSA-N 3-(5-methoxypyrazin-2-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC=1N=CC(=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 CYMMSYGHVRKYIX-UHFFFAOYSA-N 0.000 claims 1
- VDBKKEGWDIFKBU-UHFFFAOYSA-N 3-(5-methylsulfonylpyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CS(=O)(=O)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 VDBKKEGWDIFKBU-UHFFFAOYSA-N 0.000 claims 1
- AMGZORMJGHALFG-UHFFFAOYSA-N 3-(5-morpholin-4-ylpyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1CCN(CC1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 AMGZORMJGHALFG-UHFFFAOYSA-N 0.000 claims 1
- OVGNXGNNPINUCT-UHFFFAOYSA-N 3-(5-pyrazol-1-ylpyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1(N=CC=C1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OVGNXGNNPINUCT-UHFFFAOYSA-N 0.000 claims 1
- DSGCZHXBRPPHGI-UHFFFAOYSA-N 3-(5-pyrrolidin-1-ylpyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1(CCCC1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DSGCZHXBRPPHGI-UHFFFAOYSA-N 0.000 claims 1
- NNGRYLCDMNTMRH-UHFFFAOYSA-N 3-(6-methoxypyridazin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(N=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 NNGRYLCDMNTMRH-UHFFFAOYSA-N 0.000 claims 1
- VYPOTIXTGHOVOY-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[3-methyl-5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=C(C2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C VYPOTIXTGHOVOY-UHFFFAOYSA-N 0.000 claims 1
- WQDOASZSXXRUQZ-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC2=C(C=CC=C12)OCCC1=NC=2NCCCC=2C=C1 WQDOASZSXXRUQZ-UHFFFAOYSA-N 0.000 claims 1
- DLFAEACDGNDGJR-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[4-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC2=C(C=CC=C12)CCCC1=NC=2NCCCC=2C=C1 DLFAEACDGNDGJR-UHFFFAOYSA-N 0.000 claims 1
- QQVGFIHGWZQKKS-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[5-[2-(1-methyl-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-6-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC=1C=CC2=C(NCCN2C)N=1 QQVGFIHGWZQKKS-UHFFFAOYSA-N 0.000 claims 1
- DXMOTFLMGAQNII-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DXMOTFLMGAQNII-UHFFFAOYSA-N 0.000 claims 1
- BXPMWNWQYVVJET-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]pyrazolo[4,3-b]pyridin-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC2=NC(=CC=C21)OCCC1=NC=2NCCCC=2C=C1 BXPMWNWQYVVJET-UHFFFAOYSA-N 0.000 claims 1
- XWSAPZZBILUWPA-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)CCC1=NC=2NCCCC=2C=C1 XWSAPZZBILUWPA-UHFFFAOYSA-N 0.000 claims 1
- PVPRJDDNAIJPMM-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)CCCC1=NC=2NCCCC=2C=C1 PVPRJDDNAIJPMM-UHFFFAOYSA-N 0.000 claims 1
- XRGPSWUIMABLES-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]pyrazolo[4,3-b]pyridin-1-yl]propanoic acid Chemical compound COC1=CC=C(C=N1)C(CC(=O)O)N1N=CC2=NC(=CC=C21)CCCC1=NC=2NCCCC=2C=C1 XRGPSWUIMABLES-UHFFFAOYSA-N 0.000 claims 1
- ZFLUUTGCFYORAC-UHFFFAOYSA-N 3-(6-morpholin-4-ylpyrazin-2-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1CCN(CC1)C1=CN=CC(=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 ZFLUUTGCFYORAC-UHFFFAOYSA-N 0.000 claims 1
- YMAHMTBCXHIIJY-UHFFFAOYSA-N 3-(6-pyrazol-1-ylpyridin-2-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1(N=CC=C1)C1=CC=CC(=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 YMAHMTBCXHIIJY-UHFFFAOYSA-N 0.000 claims 1
- ASTNFTBTSFLTBU-UHFFFAOYSA-N 3-(7-ethyl-6,8-dihydro-5H-imidazo[1,2-a]pyrazin-3-yl)-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(C)N1CC=2N(CC1)C(=CN=2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 ASTNFTBTSFLTBU-UHFFFAOYSA-N 0.000 claims 1
- CVYLAKIKCZLOHC-UHFFFAOYSA-N 3-[1-(oxan-2-yl)pyrazolo[3,4-b]pyridin-5-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C(C=CC=2CCCNC1=2)CCOC=1C=C2C=NN(C2=CC=1)C(CC(=O)O)C=1C=C2C(=NC=1)N(N=C2)C1OCCCC1 CVYLAKIKCZLOHC-UHFFFAOYSA-N 0.000 claims 1
- CPVWBQSKHSLWTP-UHFFFAOYSA-N 3-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 CPVWBQSKHSLWTP-UHFFFAOYSA-N 0.000 claims 1
- GOOAKSHRRIUKTH-UHFFFAOYSA-N 3-[2-(2-oxopyrrolidin-1-yl)pyridin-4-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O=C1N(CCC1)C1=NC=CC(=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 GOOAKSHRRIUKTH-UHFFFAOYSA-N 0.000 claims 1
- SUJUSKSMUBILEO-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)pyrimidin-5-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1(CCC1)C1=NC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 SUJUSKSMUBILEO-UHFFFAOYSA-N 0.000 claims 1
- ZDYUDVAOUGUHGA-UHFFFAOYSA-N 3-[2-(methylamino)pyrimidin-5-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CNC1=NC=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 ZDYUDVAOUGUHGA-UHFFFAOYSA-N 0.000 claims 1
- DMSBKSXXSGRLQF-UHFFFAOYSA-N 3-[3-(2-oxopyrrolidin-1-yl)phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O=C1N(CCC1)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DMSBKSXXSGRLQF-UHFFFAOYSA-N 0.000 claims 1
- JPQLSZHXUXRPOQ-UHFFFAOYSA-N 3-[3-(3,5-dimethylpyrazol-1-yl)phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CC1=NN(C(=C1)C)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 JPQLSZHXUXRPOQ-UHFFFAOYSA-N 0.000 claims 1
- ZXIVWILLOLGGKK-UHFFFAOYSA-N 3-[3-(dimethylcarbamoyl)phenyl]-3-[4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN(C(=O)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=C(C=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C ZXIVWILLOLGGKK-UHFFFAOYSA-N 0.000 claims 1
- XIGPNPDVLUFGKH-UHFFFAOYSA-N 3-[3-(dimethylcarbamoyl)phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN(C(=O)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C XIGPNPDVLUFGKH-UHFFFAOYSA-N 0.000 claims 1
- OLIJCFGZJYGXIU-UHFFFAOYSA-N 3-[3-(dimethylcarbamoyl)phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-1-yl]propanoic acid Chemical compound CN(C(=O)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)CCC1=NC=2NCCCC=2C=C1)C OLIJCFGZJYGXIU-UHFFFAOYSA-N 0.000 claims 1
- WHUPTWMSKBMEHN-UHFFFAOYSA-N 3-[3-(dimethylcarbamoyl)phenyl]-3-[5-[3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl]indazol-1-yl]propanoic acid Chemical compound CN(C(=O)C=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)CCCC1=NC=2NCCCC=2C=C1)C WHUPTWMSKBMEHN-UHFFFAOYSA-N 0.000 claims 1
- NTUFZDNIMSFLSN-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN(C)CC=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 NTUFZDNIMSFLSN-UHFFFAOYSA-N 0.000 claims 1
- LOEIBVKVJSYXAF-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]phenyl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-1-yl]propanoic acid Chemical compound CN(C)CC=1C=C(C=CC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)CCC1=NC=2NCCCC=2C=C1 LOEIBVKVJSYXAF-UHFFFAOYSA-N 0.000 claims 1
- OFYNULKNCZVTMF-UHFFFAOYSA-N 3-[5-(1,3-dioxolan-2-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1C(OCC1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OFYNULKNCZVTMF-UHFFFAOYSA-N 0.000 claims 1
- QUPYERWVQPQYJA-UHFFFAOYSA-N 3-[5-(1,3-oxazol-5-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O1C=NC=C1C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 QUPYERWVQPQYJA-UHFFFAOYSA-N 0.000 claims 1
- IFTNTOYRWFIQOF-UHFFFAOYSA-N 3-[5-(1-methylpyrazol-4-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1N=CC(=C1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 IFTNTOYRWFIQOF-UHFFFAOYSA-N 0.000 claims 1
- AMGHLKOJWWOBGQ-UHFFFAOYSA-N 3-[5-(1H-pyrazol-5-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1N=CC=C1C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 AMGHLKOJWWOBGQ-UHFFFAOYSA-N 0.000 claims 1
- OKNQMULFPFESAF-UHFFFAOYSA-N 3-[5-(2-hydroxypropan-2-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound OC(C)(C)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OKNQMULFPFESAF-UHFFFAOYSA-N 0.000 claims 1
- TXGWYHIXFKKFCJ-UHFFFAOYSA-N 3-[5-(2-oxopyrrolidin-1-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound O=C1N(CCC1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 TXGWYHIXFKKFCJ-UHFFFAOYSA-N 0.000 claims 1
- VMJIQIVCJCPALO-UHFFFAOYSA-N 3-[5-(4-methylpiperazin-1-yl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1CCN(CC1)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 VMJIQIVCJCPALO-UHFFFAOYSA-N 0.000 claims 1
- AATUNLMIFMZODS-UHFFFAOYSA-N 3-[5-(4-methylpiperazine-1-carbonyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN1CCN(CC1)C(=O)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 AATUNLMIFMZODS-UHFFFAOYSA-N 0.000 claims 1
- UDKQLLFRYQMEBC-UHFFFAOYSA-N 3-[5-(acetamidomethyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C(C)(=O)NCC=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 UDKQLLFRYQMEBC-UHFFFAOYSA-N 0.000 claims 1
- FNWYQNUGWHFBLM-UHFFFAOYSA-N 3-[5-(aminomethyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound NCC=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 FNWYQNUGWHFBLM-UHFFFAOYSA-N 0.000 claims 1
- GNPPDFXXLIBLAT-UHFFFAOYSA-N 3-[5-(azetidine-1-carbonyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1(CCC1)C(=O)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 GNPPDFXXLIBLAT-UHFFFAOYSA-N 0.000 claims 1
- DEMDFFKBUBVBON-UHFFFAOYSA-N 3-[5-(dimethylamino)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN(C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C DEMDFFKBUBVBON-UHFFFAOYSA-N 0.000 claims 1
- BORSUYIRURXNTK-UHFFFAOYSA-N 3-[5-(dimethylcarbamoyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN(C(=O)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C BORSUYIRURXNTK-UHFFFAOYSA-N 0.000 claims 1
- LTMLALWUZPSFDF-UHFFFAOYSA-N 3-[5-(hydroxymethyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound OCC=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 LTMLALWUZPSFDF-UHFFFAOYSA-N 0.000 claims 1
- DEUJSLKVJRIQAM-UHFFFAOYSA-N 3-[5-(methanesulfonamidomethyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CS(=O)(=O)NCC=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 DEUJSLKVJRIQAM-UHFFFAOYSA-N 0.000 claims 1
- NJOYYKVELMZSLM-UHFFFAOYSA-N 3-[5-(morpholine-4-carbonyl)pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1(CCOCC1)C(=O)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 NJOYYKVELMZSLM-UHFFFAOYSA-N 0.000 claims 1
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- IKIVIELJPRVCGD-UHFFFAOYSA-N 3-[5-[(methoxycarbonylamino)methyl]pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound COC(=O)NCC=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 IKIVIELJPRVCGD-UHFFFAOYSA-N 0.000 claims 1
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- PTVXEJYPPBQOOR-UHFFFAOYSA-N 3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]-2-[(2,4,6-trimethylphenyl)sulfonylamino]propanoic acid Chemical compound N1=C(C=CC=2CCCNC1=2)CCOC=1C=C2C=NN(C2=CC=1)CC(C(=O)O)NS(=O)(=O)C1=C(C=C(C=C1C)C)C PTVXEJYPPBQOOR-UHFFFAOYSA-N 0.000 claims 1
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- VMNXFMTXIMLFRN-UHFFFAOYSA-N 3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]-3-thiophen-2-ylpropanoic acid Chemical compound N1=C(C=CC=2CCCNC1=2)CCOC=1C=C2C=NN(C2=CC=1)C(CC(=O)O)C=1SC=CC=1 VMNXFMTXIMLFRN-UHFFFAOYSA-N 0.000 claims 1
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- WAFRPEZPGRKJLO-UHFFFAOYSA-N 3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C(C=CC=2CCCNC1=2)CCOC=1C=C2C=NN(C2=CC=1)CCC(=O)O WAFRPEZPGRKJLO-UHFFFAOYSA-N 0.000 claims 1
- GYFGUFUFECQITP-UHFFFAOYSA-N 3-[5-[2-(dimethylamino)ethylcarbamoyl]pyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound CN(CCNC(=O)C=1C=C(C=NC=1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C GYFGUFUFECQITP-UHFFFAOYSA-N 0.000 claims 1
- DANPPVZFVMVCRA-UHFFFAOYSA-N 3-[6-(2-hydroxy-2-methylpropoxy)-5-methylpyridin-3-yl]-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound OC(COC1=C(C=C(C=N1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1)C)(C)C DANPPVZFVMVCRA-UHFFFAOYSA-N 0.000 claims 1
- VDTSLVCQPHHDAV-UHFFFAOYSA-N 3-cyclohexyl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C1(CCCCC1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 VDTSLVCQPHHDAV-UHFFFAOYSA-N 0.000 claims 1
- NPADYSPGSFQIKP-UHFFFAOYSA-N 3-cyclopropyl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C1(CC1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 NPADYSPGSFQIKP-UHFFFAOYSA-N 0.000 claims 1
- OPSMMPNZPIGRFH-UHFFFAOYSA-N 3-dibenzofuran-2-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C1=C(C=CC=2OC3=C(C=21)C=CC=C3)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OPSMMPNZPIGRFH-UHFFFAOYSA-N 0.000 claims 1
- OCSGCNOCIUXPTE-UHFFFAOYSA-N 3-dibenzofuran-3-yl-3-[4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C1=CC(=CC=2OC3=C(C=21)C=CC=C3)C(CC(=O)O)N1N=CC2=C(C=CC=C12)OCCC1=NC=2NCCCC=2C=C1 OCSGCNOCIUXPTE-UHFFFAOYSA-N 0.000 claims 1
- XLMYSMXHFBIJDT-UHFFFAOYSA-N 3-dibenzofuran-3-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl]indazol-1-yl]propanoic acid Chemical compound C1=CC(=CC=2OC3=C(C=21)C=CC=C3)C(CC(=O)O)N1N=CC2=CC(=CC=C12)CCC1=NC=2NCCCC=2C=C1 XLMYSMXHFBIJDT-UHFFFAOYSA-N 0.000 claims 1
- XSYIPTMSIMNQIY-UHFFFAOYSA-N 3-isoquinolin-6-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound C1=NC=CC2=CC(=CC=C12)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 XSYIPTMSIMNQIY-UHFFFAOYSA-N 0.000 claims 1
- NRMUPJOPMXBYNX-UHFFFAOYSA-N 3-pyridin-2-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C(C=CC=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 NRMUPJOPMXBYNX-UHFFFAOYSA-N 0.000 claims 1
- WZXKTGBMQOXCER-UHFFFAOYSA-N 3-pyridin-3-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=CC(=CC=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 WZXKTGBMQOXCER-UHFFFAOYSA-N 0.000 claims 1
- UEZKYPXNYUFRGT-UHFFFAOYSA-N 3-pyridin-4-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=CC=C(C=C1)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 UEZKYPXNYUFRGT-UHFFFAOYSA-N 0.000 claims 1
- PUDHAUCMWPABIY-UHFFFAOYSA-N 3-pyrido[2,3-b]pyrazin-7-yl-3-[5-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]indazol-1-yl]propanoic acid Chemical compound N1=C2C(=NC=C1)N=CC(=C2)C(CC(=O)O)N1N=CC2=CC(=CC=C12)OCCC1=NC=2NCCCC=2C=C1 PUDHAUCMWPABIY-UHFFFAOYSA-N 0.000 claims 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Immunology (AREA)
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- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Transplantation (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| PCT/US2017/060386 WO2018089357A1 (en) | 2016-11-08 | 2017-11-07 | INDAZOLE DERIVATIVES AS αV INTEGRIN ANTAGONISTS |
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| CA3042714A1 true CA3042714A1 (en) | 2018-05-17 |
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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 |
| EA201991123A1 (ru) * | 2016-11-08 | 2019-11-29 | ИНДАЗОЛОВЫЕ ПРОИЗВОДНЫЕ В КАЧЕСТВЕ АНТАГОНИСТОВ ИНТЕГРИНА αV | |
| CA3045491A1 (en) | 2016-12-29 | 2018-07-19 | Indalo Therapeutics, Inc. | Integrin antagonists |
| US11046685B2 (en) | 2017-02-28 | 2021-06-29 | Morphic Therapeutic, Inc. | Inhibitors of (α-v)(β-6) integrin |
| EP4159727B1 (en) | 2017-02-28 | 2026-04-08 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| PT3844162T (pt) | 2018-08-29 | 2025-03-28 | Morphic Therapeutic Inc | Inibidores da integrina alfa v beta6 |
| WO2020047208A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| AU2019327475B2 (en) | 2018-08-29 | 2025-06-05 | Morphic Therapeutic, Inc. | INHIBITING αV β6 INTEGRIN |
| WO2020092401A1 (en) | 2018-10-30 | 2020-05-07 | Gilead Sciences, Inc. | COMPOUNDS FOR INHIBITION OF ALPHA 4β7 INTEGRIN |
| WO2020092394A1 (en) | 2018-10-30 | 2020-05-07 | Gilead Sciences, Inc. | Imidazopyridine derivatives as alpha4beta7 integrin inhibitors |
| ES2987796T3 (es) | 2018-10-30 | 2024-11-18 | Gilead Sciences Inc | Derivados de N-benzoil-fenilalanina como inhibidores de la integrina alfa4beta7 para el tratamiento de enfermedades inflamatorias |
| DK3873884T3 (da) | 2018-10-30 | 2025-02-17 | Gilead Sciences Inc | 3-(quinolin-8-yl)-1,4-dihydropyrido[3,4-d]pyrimidin-2,4-dion-derivater som alpha4beta7-integrinhæmmere til behandling af inflammatoriske sygdomme |
| AU2020329207B2 (en) | 2019-08-14 | 2024-02-29 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| KR102048050B1 (ko) * | 2019-08-29 | 2020-01-22 | 대한민국 | Adb-푸비나카의 대사체 합성 방법 |
| EP4034236A1 (en) | 2019-09-26 | 2022-08-03 | Abionyx Pharma SA | Compounds useful for treating liver diseases |
| WO2022189856A1 (en) | 2021-03-08 | 2022-09-15 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
| EP4317145A4 (en) * | 2021-03-24 | 2025-03-12 | Shionogi & Co., Ltd | Pharmaceutical composition containing glp-1 receptor agonist having fused ring |
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| US5849736A (en) | 1993-11-24 | 1998-12-15 | The Dupont Merck Pharmaceutical Company | Isoxazoline and isoxazole fibrinogen receptor antagonists |
| CA2240439A1 (en) * | 1995-12-22 | 1997-07-03 | The Dupont Merck Pharmaceutical Company | Novel integrin receptor antagonists |
| ZA972195B (en) | 1996-03-15 | 1998-09-14 | Du Pont Merck Pharma | Spirocycle integrin inhibitors |
| JP2001524481A (ja) | 1997-11-26 | 2001-12-04 | デュポン ファーマシューティカルズ カンパニー | αＶβ３アンタゴニストとしての１，３，４−チアジアゾール類および１，３，４−オキサジアゾール類 |
| EP1047425A4 (en) | 1997-12-17 | 2009-04-22 | Merck & Co Inc | INTEGRIN RECEPTOR ANTAGONISTS |
| AU748621B2 (en) | 1998-08-13 | 2002-06-06 | Merck & Co., Inc. | Integrin receptor antagonists |
| US6921767B2 (en) | 2000-06-15 | 2005-07-26 | Pharmacia Corporation | Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives |
| WO2002060438A1 (en) * | 2001-01-29 | 2002-08-08 | 3-Dimensional Pharmaceuticals, Inc. | Substituted indoles and their use as integrin antagonists |
| US6872730B2 (en) * | 2001-04-27 | 2005-03-29 | 3-Dimensional Pharmaceuticals, Inc. | Substituted benzofurans and benzothiophenes, methods of making and methods of use as integrin antagonists |
| AU2002319282B2 (en) * | 2001-08-01 | 2007-06-28 | Merck Patent Gmbh | Integrin inhibitors for the treatment of eye diseases |
| WO2006108040A1 (en) | 2005-04-05 | 2006-10-12 | Janssen Pharmaceutica, N.V. | Substituted indoles and their use as integrin antagonists |
| JP2009539815A (ja) | 2006-06-09 | 2009-11-19 | アストラゼネカ アクチボラグ | 固形腫瘍の治療用のａ５ｂ１アンタゴニストとしてのＮ−（ベンゾイル）−Ｏ−［２−（ピリジン−２−イルアミノ）エチル］−Ｌ−チロシン誘導体と関連化合物 |
| WO2008125811A1 (en) | 2007-04-11 | 2008-10-23 | Astrazeneca Ab | N-[HETEROARYLCARBONYL]-S-THIENYL-L-ALANINE DERIVATIVES AS α5β1 ANTAGONISTS |
| 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 |
| JP6387100B2 (ja) | 2014-08-08 | 2018-09-05 | 株式会社Ｆｕｊｉ | スクリーン印刷装置 |
| 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 |
| GB201417002D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| GB201417011D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| EP3925959A1 (en) | 2015-02-19 | 2021-12-22 | OcuTerra Therapeutics, Inc. | Fluorinated derivatives of 3-(2-oxo-3-(3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)propyl)imidazolidin-1-yl)propanoic acid and uses thereof |
| AU2016228852A1 (en) | 2015-03-10 | 2017-10-19 | The Regents Of The University Of California | Anti-alphavbeta1 integrin inhibitors and methods of use |
| EA201991123A1 (ru) * | 2016-11-08 | 2019-11-29 | ИНДАЗОЛОВЫЕ ПРОИЗВОДНЫЕ В КАЧЕСТВЕ АНТАГОНИСТОВ ИНТЕГРИНА αV |
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| AU2017359027A1 (en) | 2019-06-20 |
| MX378565B (es) | 2025-03-10 |
| US20190256496A1 (en) | 2019-08-22 |
| JP7213804B2 (ja) | 2023-01-27 |
| JP2019536768A (ja) | 2019-12-19 |
| MX2019005243A (es) | 2019-08-05 |
| EP3538519B1 (en) | 2021-07-28 |
| CN110214137A (zh) | 2019-09-06 |
| ES2886650T3 (es) | 2021-12-20 |
| EA201991123A1 (ru) | 2019-11-29 |
| IL266472A (en) | 2019-07-31 |
| EP3538519A1 (en) | 2019-09-18 |
| KR102506327B1 (ko) | 2023-03-03 |
| MA46745A (fr) | 2021-03-31 |
| US11028071B2 (en) | 2021-06-08 |
| US10745384B2 (en) | 2020-08-18 |
| KR20190076033A (ko) | 2019-07-01 |
| WO2018089357A1 (en) | 2018-05-17 |
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