ZA200308024B - Inhibitors of integrin alphavbeta6. - Google Patents

Inhibitors of integrin alphavbeta6. Download PDF

Info

Publication number: ZA200308024B
Authority: ZA; South Africa
Prior art keywords: pyridin; ylamino; propionic acid; biphenyl; butanoylamino
Prior art date: 2001-03-16

Application number

ZA200308024A

Other languages

English (en)

Inventor

Oliver Schadt

Wolfgang Staehle

Alfred Jonczyk

Simon Goodman

Original Assignee

Merck Patent Gmbh

Priority date (The priority date 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 date listed.)

2001-03-16

Filing date

2003-10-15

Publication date

2005-01-17

2003-10-15 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2005-01-17 Publication of ZA200308024B publication Critical patent/ZA200308024B/en

Links

239000003112 inhibitor Substances 0.000 title claims description 9
108010004788 integrin alphavbeta6 Proteins 0.000 title description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 376
235000019260 propionic acid Nutrition 0.000 claims description 188
-1 pyridin-2-ylamino Chemical group 0.000 claims description 82
150000001875 compounds Chemical class 0.000 claims description 65
108010044426 integrins Proteins 0.000 claims description 50
102000006495 integrins Human genes 0.000 claims description 50
125000006239 protecting group Chemical group 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
206010028980 Neoplasm Diseases 0.000 claims description 19
239000012453 solvate Substances 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 18
125000003277 amino group Chemical group 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
230000004761 fibrosis Effects 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
206010016654 Fibrosis Diseases 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 6
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
230000004054 inflammatory process Effects 0.000 claims description 5
230000001575 pathological effect Effects 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
206010041823 squamous cell carcinoma Diseases 0.000 claims description 5
230000029663 wound healing Effects 0.000 claims description 5
241000193738 Bacillus anthracis Species 0.000 claims description 4
206010061218 Inflammation Diseases 0.000 claims description 4
206010027476 Metastases Diseases 0.000 claims description 4
230000002152 alkylating effect Effects 0.000 claims description 4
230000033115 angiogenesis Effects 0.000 claims description 4
210000004369 blood Anatomy 0.000 claims description 4
239000008280 blood Substances 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
208000035475 disorder Diseases 0.000 claims description 4
210000004072 lung Anatomy 0.000 claims description 4
230000009401 metastasis Effects 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
235000010290 biphenyl Nutrition 0.000 claims description 3
239000004305 biphenyl Substances 0.000 claims description 3
210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
230000035755 proliferation Effects 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
210000001519 tissue Anatomy 0.000 claims description 3
XFCNBBOOZVDUCY-CGAIIQECSA-N (3s)-4-[[2-carboxy-1-(4-phenylphenyl)ethyl]amino]-4-oxo-3-[5-(pyridin-2-ylamino)pentanoylamino]butanoic acid Chemical compound N([C@@H](CC(=O)O)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 XFCNBBOOZVDUCY-CGAIIQECSA-N 0.000 claims description 2
ZMDCJXOUGZUCBC-PMCHYTPCSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[5-(pyridin-2-ylamino)pentanoylamino]pentanoyl]amino]propanoic acid Chemical compound N([C@@H](CCC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 ZMDCJXOUGZUCBC-PMCHYTPCSA-N 0.000 claims description 2
BNIWUUGFRYMHJB-QMCAYLGFSA-N 3-[[(2r)-3-hydroxy-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](C(O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 BNIWUUGFRYMHJB-QMCAYLGFSA-N 0.000 claims description 2
HSKBQDBAQCEPLF-DCWQJPKNSA-N 3-[[(2r)-5-(diaminomethylideneamino)-2-[5-(pyridin-2-ylamino)pentanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCCNC(=N)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 HSKBQDBAQCEPLF-DCWQJPKNSA-N 0.000 claims description 2
RDSUIWIICBEWHT-DCWQJPKNSA-N 3-[[(2r)-5-amino-2-[5-(pyridin-2-ylamino)pentanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCCN)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 RDSUIWIICBEWHT-DCWQJPKNSA-N 0.000 claims description 2
FNDSFJFNWGELLU-SSYAZFEXSA-N 3-[[(2s)-3-(acetamidomethylsulfanyl)-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CSCNC(=O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 FNDSFJFNWGELLU-SSYAZFEXSA-N 0.000 claims description 2
VBGFEPPITRDCAJ-FXDYGKIASA-N 3-[[(2s)-3-ethylsulfanyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CSCC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 VBGFEPPITRDCAJ-FXDYGKIASA-N 0.000 claims description 2
FSXOYTMPYWLBLF-CGAIIQECSA-N 3-[[(2s)-3-hydroxy-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 FSXOYTMPYWLBLF-CGAIIQECSA-N 0.000 claims description 2
KZKUJOPZSWGYCY-SKCDSABHSA-N 3-[[(2s)-4-hydroxy-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 KZKUJOPZSWGYCY-SKCDSABHSA-N 0.000 claims description 2
IAVZHVRNCXXFIQ-MBMZGMDYSA-N 3-[[(2s)-6-(carbamoylamino)-2-[6-(pyridin-2-ylamino)hexanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCCNC(=O)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCCNC1=CC=CC=N1 IAVZHVRNCXXFIQ-MBMZGMDYSA-N 0.000 claims description 2
YKTPPPDELUIVHI-QBHOUYDASA-N 3-[[(2s)-6-amino-2-[5-(pyridin-2-ylamino)pentanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCCN)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 YKTPPPDELUIVHI-QBHOUYDASA-N 0.000 claims description 2
206010019668 Hepatic fibrosis Diseases 0.000 claims description 2
201000004681 Psoriasis Diseases 0.000 claims description 2
238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
208000007536 Thrombosis Diseases 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
230000002491 angiogenic effect Effects 0.000 claims description 2
125000005427 anthranyl group Chemical group 0.000 claims description 2
150000001499 aryl bromides Chemical class 0.000 claims description 2
150000007514 bases Chemical class 0.000 claims description 2
125000005620 boronic acid group Chemical class 0.000 claims description 2
230000009787 cardiac fibrosis Effects 0.000 claims description 2
230000008878 coupling Effects 0.000 claims description 2
238000010168 coupling process Methods 0.000 claims description 2
238000005859 coupling reaction Methods 0.000 claims description 2
238000011161 development Methods 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
210000000987 immune system Anatomy 0.000 claims description 2
201000011486 lichen planus Diseases 0.000 claims description 2
210000003205 muscle Anatomy 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
210000000056 organ Anatomy 0.000 claims description 2
201000002793 renal fibrosis Diseases 0.000 claims description 2
238000012360 testing method Methods 0.000 claims description 2
208000007212 Foot-and-Mouth Disease Diseases 0.000 claims 2
241000710198 Foot-and-mouth disease virus Species 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
YZXXIKCLBLMVTJ-IKOFQBKESA-N (4r)-5-[[2-carboxy-1-(4-phenylphenyl)ethyl]amino]-5-oxo-4-[5-(pyridin-2-ylamino)pentanoylamino]pentanoic acid Chemical compound N([C@H](CCC(=O)O)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 YZXXIKCLBLMVTJ-IKOFQBKESA-N 0.000 claims 1
MPOIJBCQWRETSO-UXMRNZNESA-N (4s)-5-[[2-carboxy-1-(4-phenylphenyl)ethyl]amino]-5-oxo-4-[4-(pyridin-2-ylamino)butanoylamino]pentanoic acid Chemical compound N([C@@H](CCC(=O)O)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 MPOIJBCQWRETSO-UXMRNZNESA-N 0.000 claims 1
BPBNVJUUBUTFCD-UHFFFAOYSA-N 3-(3-bromophenyl)-3-[[3-phenylmethoxy-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C=1C=CC(Br)=CC=1C(CC(=O)O)NC(=O)C(NC(=O)CCCCNC=1N=CC=CC=1)COCC1=CC=CC=C1 BPBNVJUUBUTFCD-UHFFFAOYSA-N 0.000 claims 1
QILMETWBQMEBAZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-[[3-phenylmethoxy-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C=1C=CC(Cl)=CC=1C(CC(=O)O)NC(=O)C(NC(=O)CCCCNC=1N=CC=CC=1)COCC1=CC=CC=C1 QILMETWBQMEBAZ-UHFFFAOYSA-N 0.000 claims 1
SZNCTGONOTXZQF-DDAUYOFQSA-N 3-(4-hydroxy-n-[(2r)-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]anilino)-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](C)C(=O)N(C(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC(O)=CC=1)C(=O)CCCCNC1=CC=CC=N1 SZNCTGONOTXZQF-DDAUYOFQSA-N 0.000 claims 1
DJBGPUVXNUYDND-CGHJUBPDSA-N 3-(4-phenylphenyl)-3-[[(2r)-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound N([C@H](C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 DJBGPUVXNUYDND-CGHJUBPDSA-N 0.000 claims 1
OUEDEYHFICOQAL-VCHQGTEKSA-N 3-(4-phenylphenyl)-3-[[(2r)-2-phenyl-2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoic acid Chemical compound N([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 OUEDEYHFICOQAL-VCHQGTEKSA-N 0.000 claims 1
AIODABPXAVUICN-BDCODIICSA-N 3-(4-phenylphenyl)-3-[[(2r)-3-phenyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1=CC=CC=C1 AIODABPXAVUICN-BDCODIICSA-N 0.000 claims 1
HWAMMTZNTCKXIB-PUOOBJKZSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[4-(pyridin-2-ylamino)butanoylamino]-3-tritylsulfanylpropanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HWAMMTZNTCKXIB-PUOOBJKZSA-N 0.000 claims 1
DJBGPUVXNUYDND-QHELBMECSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound N([C@@H](C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 DJBGPUVXNUYDND-QHELBMECSA-N 0.000 claims 1
AIODABPXAVUICN-ZSXSBBPPSA-N 3-(4-phenylphenyl)-3-[[(2s)-3-phenyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1=CC=CC=C1 AIODABPXAVUICN-ZSXSBBPPSA-N 0.000 claims 1
VINDNIBCWUZHNG-DYJLHVNUSA-N 3-(4-phenylphenyl)-3-[sulfanyl-[(2s)-5,5,5-triphenyl-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)N(S)C(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)CC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VINDNIBCWUZHNG-DYJLHVNUSA-N 0.000 claims 1
FZPSMXJOSFPGSK-YPJJGMIRSA-N 3-[[(2r)-3-cyclohexyl-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)C1CCCCC1 FZPSMXJOSFPGSK-YPJJGMIRSA-N 0.000 claims 1
VDDPDNSCNONJFV-OZAIVSQSSA-N 3-[[(2r)-3-hydroxy-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 VDDPDNSCNONJFV-OZAIVSQSSA-N 0.000 claims 1
REJVOUKDMBDPGM-MIHMCVIASA-N 3-[[(2r)-4-hydroxy-2-[4-(pyridin-2-ylamino)butanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 REJVOUKDMBDPGM-MIHMCVIASA-N 0.000 claims 1
KZKUJOPZSWGYCY-IKOFQBKESA-N 3-[[(2r)-4-hydroxy-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 KZKUJOPZSWGYCY-IKOFQBKESA-N 0.000 claims 1
ARAXKGCCMWKXJQ-MIHMCVIASA-N 3-[[(2r)-5-amino-5-oxo-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCC(=O)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 ARAXKGCCMWKXJQ-MIHMCVIASA-N 0.000 claims 1
TWBPUTGOWCRJBA-IKOFQBKESA-N 3-[[(2r)-5-amino-5-oxo-2-[5-(pyridin-2-ylamino)pentanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCC(=O)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 TWBPUTGOWCRJBA-IKOFQBKESA-N 0.000 claims 1
YKTPPPDELUIVHI-AVJYQCBHSA-N 3-[[(2r)-6-amino-2-[5-(pyridin-2-ylamino)pentanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCCCN)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 YKTPPPDELUIVHI-AVJYQCBHSA-N 0.000 claims 1
WGRRSEHXNFVIDM-AMVUTOCUSA-N 3-[[(2s)-3-(1h-imidazol-5-yl)-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)C1=CNC=N1 WGRRSEHXNFVIDM-AMVUTOCUSA-N 0.000 claims 1
PRIZFANURVSDFS-GEVKEYJPSA-N 3-[[(2s)-3-(1h-imidazol-5-yl)-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1=CNC=N1 PRIZFANURVSDFS-GEVKEYJPSA-N 0.000 claims 1
FZPSMXJOSFPGSK-XIJSCUBXSA-N 3-[[(2s)-3-cyclohexyl-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)C1CCCCC1 FZPSMXJOSFPGSK-XIJSCUBXSA-N 0.000 claims 1
AGQGJTYKWJWFGZ-ZSXSBBPPSA-N 3-[[(2s)-3-cyclohexyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1CCCCC1 AGQGJTYKWJWFGZ-ZSXSBBPPSA-N 0.000 claims 1
VYROGZDKKNJLIE-ZSXSBBPPSA-N 3-[[(2s)-3-phenylmethoxy-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)OCC1=CC=CC=C1 VYROGZDKKNJLIE-ZSXSBBPPSA-N 0.000 claims 1
BGWIHQNBKMIFRR-SSYAZFEXSA-N 3-[[(2s)-3-tert-butylsulfanyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CSC(C)(C)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 BGWIHQNBKMIFRR-SSYAZFEXSA-N 0.000 claims 1
ZFWLBSNVAFEFSD-WMBILQROSA-N 3-[[(2s)-4-methylsulfinyl-2-[4-(pyridin-2-ylamino)butanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCS(=O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 ZFWLBSNVAFEFSD-WMBILQROSA-N 0.000 claims 1
YLUUMQCBWLIIEF-SKCDSABHSA-N 3-[[(2s)-4-methylsulfonyl-2-[4-(pyridin-2-ylamino)butanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCS(=O)(=O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 YLUUMQCBWLIIEF-SKCDSABHSA-N 0.000 claims 1
WNZSYBGAEJKOHR-PMCHYTPCSA-N 3-[[(2s)-4-methylsulfonyl-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCS(=O)(=O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 WNZSYBGAEJKOHR-PMCHYTPCSA-N 0.000 claims 1
XUNGXUSJRZYCRO-QBHOUYDASA-N 3-[[(2s)-4-methylsulfonyl-2-[6-(pyridin-2-ylamino)hexanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCS(=O)(=O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCCNC1=CC=CC=N1 XUNGXUSJRZYCRO-QBHOUYDASA-N 0.000 claims 1
HSKBQDBAQCEPLF-PMCHYTPCSA-N 3-[[(2s)-5-(diaminomethylideneamino)-2-[5-(pyridin-2-ylamino)pentanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCNC(=N)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 HSKBQDBAQCEPLF-PMCHYTPCSA-N 0.000 claims 1
VODKZXWYJNBSTC-SKCDSABHSA-N 3-[[(2s)-5-amino-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCN)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 VODKZXWYJNBSTC-SKCDSABHSA-N 0.000 claims 1
ZKYZWVVVNUMBMM-QBHOUYDASA-N 3-[[(2s)-6-(carbamoylamino)-2-[5-(pyridin-2-ylamino)pentanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCCNC(=O)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 ZKYZWVVVNUMBMM-QBHOUYDASA-N 0.000 claims 1
HYNNAXVPIRXYMA-SFCXHYMASA-N 3-[[(2s)-6-(phenylmethoxycarbonylamino)-2-[6-(pyridin-2-ylamino)hexanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCCNC=1N=CC=CC=1)CCCNC(=O)OCC1=CC=CC=C1 HYNNAXVPIRXYMA-SFCXHYMASA-N 0.000 claims 1
YJLRLCMUUNNEHH-PMCHYTPCSA-N 3-[[(2s)-6-amino-2-[4-(pyridin-2-ylamino)butanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCCN)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 YJLRLCMUUNNEHH-PMCHYTPCSA-N 0.000 claims 1
IHQMJBDOMSWBGC-UHFFFAOYSA-N 3-[[2-methyl-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(O)=O)NC(=O)C(C)(C)NC(=O)CCCNC1=CC=CC=N1 IHQMJBDOMSWBGC-UHFFFAOYSA-N 0.000 claims 1
IJHBVAAHWUGTOU-UHFFFAOYSA-N 3-[[2-methyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(O)=O)NC(=O)C(C)(C)NC(=O)CCCCNC1=CC=CC=N1 IJHBVAAHWUGTOU-UHFFFAOYSA-N 0.000 claims 1
208000009304 Acute Kidney Injury Diseases 0.000 claims 1
206010002329 Aneurysm Diseases 0.000 claims 1
206010002383 Angina Pectoris Diseases 0.000 claims 1
206010003210 Arteriosclerosis Diseases 0.000 claims 1
201000001320 Atherosclerosis Diseases 0.000 claims 1
208000035143 Bacterial infection Diseases 0.000 claims 1
241000222122 Candida albicans Species 0.000 claims 1
206010009900 Colitis ulcerative Diseases 0.000 claims 1
208000011231 Crohn disease Diseases 0.000 claims 1
201000003883 Cystic fibrosis Diseases 0.000 claims 1
206010051055 Deep vein thrombosis Diseases 0.000 claims 1
206010012689 Diabetic retinopathy Diseases 0.000 claims 1
206010014664 Endocardial fibrosis Diseases 0.000 claims 1
206010017533 Fungal infection Diseases 0.000 claims 1
208000010412 Glaucoma Diseases 0.000 claims 1
201000002563 Histoplasmosis Diseases 0.000 claims 1
208000037147 Hypercalcaemia Diseases 0.000 claims 1
201000002980 Hyperparathyroidism Diseases 0.000 claims 1
206010061216 Infarction Diseases 0.000 claims 1
206010061217 Infestation Diseases 0.000 claims 1
208000031888 Mycoses Diseases 0.000 claims 1
208000010191 Osteitis Deformans Diseases 0.000 claims 1
208000001132 Osteoporosis Diseases 0.000 claims 1
208000027868 Paget disease Diseases 0.000 claims 1
208000010378 Pulmonary Embolism Diseases 0.000 claims 1
208000033626 Renal failure acute Diseases 0.000 claims 1
241000580858 Simian-Human immunodeficiency virus Species 0.000 claims 1
208000032109 Transient ischaemic attack Diseases 0.000 claims 1
201000006704 Ulcerative Colitis Diseases 0.000 claims 1
208000007814 Unstable Angina Diseases 0.000 claims 1
206010047249 Venous thrombosis Diseases 0.000 claims 1
208000036142 Viral infection Diseases 0.000 claims 1
201000011040 acute kidney failure Diseases 0.000 claims 1
238000002399 angioplasty Methods 0.000 claims 1
208000011775 arteriosclerosis disease Diseases 0.000 claims 1
208000022362 bacterial infectious disease Diseases 0.000 claims 1
210000004204 blood vessel Anatomy 0.000 claims 1
210000000988 bone and bone Anatomy 0.000 claims 1
210000004556 brain Anatomy 0.000 claims 1
210000000481 breast Anatomy 0.000 claims 1
229940095731 candida albicans Drugs 0.000 claims 1
230000000747 cardiac effect Effects 0.000 claims 1
208000019425 cirrhosis of liver Diseases 0.000 claims 1
230000035876 healing Effects 0.000 claims 1
230000000148 hypercalcaemia Effects 0.000 claims 1
230000007574 infarction Effects 0.000 claims 1
210000003734 kidney Anatomy 0.000 claims 1
210000004185 liver Anatomy 0.000 claims 1
208000002780 macular degeneration Diseases 0.000 claims 1
208000027202 mammary Paget disease Diseases 0.000 claims 1
201000006417 multiple sclerosis Diseases 0.000 claims 1
208000001491 myopia Diseases 0.000 claims 1
230000004379 myopia Effects 0.000 claims 1
201000008482 osteoarthritis Diseases 0.000 claims 1
230000000010 osteolytic effect Effects 0.000 claims 1
210000001672 ovary Anatomy 0.000 claims 1
210000000496 pancreas Anatomy 0.000 claims 1
230000003071 parasitic effect Effects 0.000 claims 1
230000035935 pregnancy Effects 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
208000037803 restenosis Diseases 0.000 claims 1
201000003068 rheumatic fever Diseases 0.000 claims 1
210000000952 spleen Anatomy 0.000 claims 1
210000001550 testis Anatomy 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
210000001215 vagina Anatomy 0.000 claims 1
230000009385 viral infection Effects 0.000 claims 1
210000004027 cell Anatomy 0.000 description 22
229910052760 oxygen Inorganic materials 0.000 description 14
239000007790 solid phase Substances 0.000 description 12
229910052717 sulfur Inorganic materials 0.000 description 12
239000005557 antagonist Substances 0.000 description 10
230000014509 gene expression Effects 0.000 description 10
108010021309 integrin beta6 Proteins 0.000 description 9
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 7
239000000556 agonist Substances 0.000 description 7
230000027455 binding Effects 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
125000004076 pyridyl group Chemical group 0.000 description 7
239000000126 substance Substances 0.000 description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
210000004881 tumor cell Anatomy 0.000 description 6
102000009618 Transforming Growth Factors Human genes 0.000 description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
230000004913 activation Effects 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000003993 interaction Effects 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 4
108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
210000000981 epithelium Anatomy 0.000 description 4
239000003446 ligand Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
210000003491 skin Anatomy 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 3
206010009944 Colon cancer Diseases 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
102100037362 Fibronectin Human genes 0.000 description 3
108010067306 Fibronectins Proteins 0.000 description 3
102000003886 Glycoproteins Human genes 0.000 description 3
108090000288 Glycoproteins Proteins 0.000 description 3
102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
206010052428 Wound Diseases 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
229960000846 camphor Drugs 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
125000001041 indolyl group Chemical group 0.000 description 3
208000002741 leukoplakia Diseases 0.000 description 3
230000001404 mediated effect Effects 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
230000028327 secretion Effects 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
230000002792 vascular Effects 0.000 description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000723346 Cinnamomum camphora Species 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
108010037362 Extracellular Matrix Proteins Proteins 0.000 description 2
102000010834 Extracellular Matrix Proteins Human genes 0.000 description 2
108060003393 Granulin Proteins 0.000 description 2
102100022337 Integrin alpha-V Human genes 0.000 description 2
102000000424 Matrix Metalloproteinase 2 Human genes 0.000 description 2
108010016165 Matrix Metalloproteinase 2 Proteins 0.000 description 2
102000005741 Metalloproteases Human genes 0.000 description 2
108010006035 Metalloproteases Proteins 0.000 description 2
206010061309 Neoplasm progression Diseases 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
206010035664 Pneumonia Diseases 0.000 description 2
102000007000 Tenascin Human genes 0.000 description 2
108010008125 Tenascin Proteins 0.000 description 2
108010031318 Vitronectin Proteins 0.000 description 2
102100035140 Vitronectin Human genes 0.000 description 2
230000009471 action Effects 0.000 description 2
125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 2
230000006907 apoptotic process Effects 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
230000033228 biological regulation Effects 0.000 description 2
210000001772 blood platelet Anatomy 0.000 description 2
LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229930008380 camphor Natural products 0.000 description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
230000021164 cell adhesion Effects 0.000 description 2
210000000170 cell membrane Anatomy 0.000 description 2
208000029742 colonic neoplasm Diseases 0.000 description 2
210000002808 connective tissue Anatomy 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
210000002919 epithelial cell Anatomy 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
210000002950 fibroblast Anatomy 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
230000006870 function Effects 0.000 description 2
230000004941 influx Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
210000002510 keratinocyte Anatomy 0.000 description 2
125000005647 linker group Chemical group 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
210000000440 neutrophil Anatomy 0.000 description 2
CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
230000008506 pathogenesis Effects 0.000 description 2
XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
238000012552 review Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
230000017423 tissue regeneration Effects 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
239000003053 toxin Substances 0.000 description 2
231100000765 toxin Toxicity 0.000 description 2
108700012359 toxins Proteins 0.000 description 2
102100036537 von Willebrand factor Human genes 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
MPOIJBCQWRETSO-MIHMCVIASA-N (4r)-5-[[2-carboxy-1-(4-phenylphenyl)ethyl]amino]-5-oxo-4-[4-(pyridin-2-ylamino)butanoylamino]pentanoic acid Chemical compound N([C@H](CCC(=O)O)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 MPOIJBCQWRETSO-MIHMCVIASA-N 0.000 description 1
YZXXIKCLBLMVTJ-SKCDSABHSA-N (4s)-5-[[2-carboxy-1-(4-phenylphenyl)ethyl]amino]-5-oxo-4-[5-(pyridin-2-ylamino)pentanoylamino]pentanoic acid Chemical compound N([C@@H](CCC(=O)O)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 YZXXIKCLBLMVTJ-SKCDSABHSA-N 0.000 description 1
HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 1
229930007886 (R)-camphor Natural products 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
YRUBJDXEYFCYCX-UHFFFAOYSA-N 2-(3-chlorophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(Cl)=C1 YRUBJDXEYFCYCX-UHFFFAOYSA-N 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
XPTVXCGPHUFVKZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-[[3-phenylmethoxy-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C=1C=C(Cl)C=CC=1C(CC(=O)O)NC(=O)C(NC(=O)CCCCNC=1N=CC=CC=1)COCC1=CC=CC=C1 XPTVXCGPHUFVKZ-UHFFFAOYSA-N 0.000 description 1
YLEXZBLVFOGISN-UHFFFAOYSA-N 3-(4-phenylphenyl)-3-[2-[4-(pyridin-2-ylamino)pentanoylamino]pentanoylamino]propanoic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC(O)=O)NC(=O)C(CCC)NC(=O)CCC(C)NC1=CC=CC=N1 YLEXZBLVFOGISN-UHFFFAOYSA-N 0.000 description 1
HWAMMTZNTCKXIB-ABUZLUSGSA-N 3-(4-phenylphenyl)-3-[[(2r)-2-[4-(pyridin-2-ylamino)butanoylamino]-3-tritylsulfanylpropanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HWAMMTZNTCKXIB-ABUZLUSGSA-N 0.000 description 1
AKYNDMZJZIHGOQ-DCWQJPKNSA-N 3-(4-phenylphenyl)-3-[[(2r)-2-[4-(pyridin-2-ylamino)butanoylamino]hexanoyl]amino]propanoic acid Chemical compound N([C@H](CCCC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 AKYNDMZJZIHGOQ-DCWQJPKNSA-N 0.000 description 1
SUPWJJGZLTYHCP-IKOFQBKESA-N 3-(4-phenylphenyl)-3-[[(2r)-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]propanoic acid Chemical compound N([C@H](CCC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 SUPWJJGZLTYHCP-IKOFQBKESA-N 0.000 description 1
XDCSNKQPORHGSP-YPJJGMIRSA-N 3-(4-phenylphenyl)-3-[[(2r)-3-pyridin-4-yl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1=CC=NC=C1 XDCSNKQPORHGSP-YPJJGMIRSA-N 0.000 description 1
VOENVFOYYDMCFA-GEVKEYJPSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[4-(pyridin-2-ylamino)butanoylamino]-3-thiophen-2-ylpropanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCNC=1N=CC=CC=1)C1=CC=CS1 VOENVFOYYDMCFA-GEVKEYJPSA-N 0.000 description 1
OMPUEUPFXTXVMW-UXMRNZNESA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[4-(pyridin-2-ylamino)butanoylamino]butanoyl]amino]propanoic acid Chemical compound N([C@@H](CC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 OMPUEUPFXTXVMW-UXMRNZNESA-N 0.000 description 1
AKYNDMZJZIHGOQ-PMCHYTPCSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[4-(pyridin-2-ylamino)butanoylamino]hexanoyl]amino]propanoic acid Chemical compound N([C@@H](CCCC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 AKYNDMZJZIHGOQ-PMCHYTPCSA-N 0.000 description 1
LXMKMDOYTGHUQK-FBUHDGFBSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[5-(pyridin-2-ylamino)pentanoylamino]-3-tritylsulfanylpropanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LXMKMDOYTGHUQK-FBUHDGFBSA-N 0.000 description 1
IWRGWSKVGRONEP-ZAGGQVEOSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[5-(pyridin-2-ylamino)pentanoylamino]-4-tritylsulfanylbutanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)CSC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IWRGWSKVGRONEP-ZAGGQVEOSA-N 0.000 description 1
NIDKKNKVEVPZID-QBHOUYDASA-N 3-(4-phenylphenyl)-3-[[(2s)-2-[5-(pyridin-2-ylamino)pentanoylamino]hexanoyl]amino]propanoic acid Chemical compound N([C@@H](CCCC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 NIDKKNKVEVPZID-QBHOUYDASA-N 0.000 description 1
OUEDEYHFICOQAL-YYMSGCCCSA-N 3-(4-phenylphenyl)-3-[[(2s)-2-phenyl-2-[5-(pyridin-2-ylamino)pentanoylamino]acetyl]amino]propanoic acid Chemical compound N([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 OUEDEYHFICOQAL-YYMSGCCCSA-N 0.000 description 1
XDCSNKQPORHGSP-XIJSCUBXSA-N 3-(4-phenylphenyl)-3-[[(2s)-3-pyridin-4-yl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1=CC=NC=C1 XDCSNKQPORHGSP-XIJSCUBXSA-N 0.000 description 1
YMMAYLSUMNVWPX-ZAGGQVEOSA-N 3-(4-phenylphenyl)-3-[[(2s)-5,5,5-triphenyl-2-[5-(pyridin-2-ylamino)pentanoylamino]pentanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)CC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YMMAYLSUMNVWPX-ZAGGQVEOSA-N 0.000 description 1
FSXOYTMPYWLBLF-XMMISQBUSA-N 3-[[(2r)-3-hydroxy-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 FSXOYTMPYWLBLF-XMMISQBUSA-N 0.000 description 1
QABVNMIXXBBMFV-FXDYGKIASA-N 3-[[(2r)-4-methyl-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CC(C)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 QABVNMIXXBBMFV-FXDYGKIASA-N 0.000 description 1
CKXRJHLIUKWLAV-DCWQJPKNSA-N 3-[[(2r)-4-methylsulfanyl-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCSC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 CKXRJHLIUKWLAV-DCWQJPKNSA-N 0.000 description 1
SOCFZCXOYOGPBA-IKOFQBKESA-N 3-[[(2r)-5-(diaminomethylideneamino)-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCCNC(=N)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 SOCFZCXOYOGPBA-IKOFQBKESA-N 0.000 description 1
VODKZXWYJNBSTC-IKOFQBKESA-N 3-[[(2r)-5-amino-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@H](CCCN)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 VODKZXWYJNBSTC-IKOFQBKESA-N 0.000 description 1
PFEBGBYPGNEUIZ-FLDQDSGZSA-N 3-[[(2s)-3-(1h-indol-2-yl)-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CC=1NC2=CC=CC=C2C=1)C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 PFEBGBYPGNEUIZ-FLDQDSGZSA-N 0.000 description 1
BAWUTRSYXWMVPD-ZSXSBBPPSA-N 3-[[(2s)-3-(4-hydroxyphenyl)-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)C1=CC=C(O)C=C1 BAWUTRSYXWMVPD-ZSXSBBPPSA-N 0.000 description 1
NEFSOHJSDPAWSQ-BEBVUIBBSA-N 3-[[(2s)-3-benzhydrylsulfanyl-2-[5-(pyridin-2-ylamino)pentanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)SC(C=1C=CC=CC=1)C1=CC=CC=C1 NEFSOHJSDPAWSQ-BEBVUIBBSA-N 0.000 description 1
VDDPDNSCNONJFV-WCSIJFPASA-N 3-[[(2s)-3-hydroxy-2-[4-(pyridin-2-ylamino)butanoylamino]propanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CO)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 VDDPDNSCNONJFV-WCSIJFPASA-N 0.000 description 1
BNIWUUGFRYMHJB-MQBAUGIOSA-N 3-[[(2s)-3-hydroxy-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](C(O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 BNIWUUGFRYMHJB-MQBAUGIOSA-N 0.000 description 1
NODBRHWQWQOCEA-QFCCLOIZSA-N 3-[[(2s)-3-methyl-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](C(C)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 NODBRHWQWQOCEA-QFCCLOIZSA-N 0.000 description 1
YGYAXILWUZIZBC-QBHOUYDASA-N 3-[[(2s)-4-methoxy-2-[6-(pyridin-2-ylamino)hexanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCOC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCCNC1=CC=CC=N1 YGYAXILWUZIZBC-QBHOUYDASA-N 0.000 description 1
CKXRJHLIUKWLAV-PMCHYTPCSA-N 3-[[(2s)-4-methylsulfanyl-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCSC)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 CKXRJHLIUKWLAV-PMCHYTPCSA-N 0.000 description 1
VSVBBLXZTKWPKH-NSNGHSJKSA-N 3-[[(2s)-4-methylsulfinyl-2-[5-(pyridin-2-ylamino)pentanoylamino]butanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCS(=O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 VSVBBLXZTKWPKH-NSNGHSJKSA-N 0.000 description 1
RDSUIWIICBEWHT-PMCHYTPCSA-N 3-[[(2s)-5-amino-2-[5-(pyridin-2-ylamino)pentanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCN)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 RDSUIWIICBEWHT-PMCHYTPCSA-N 0.000 description 1
ARAXKGCCMWKXJQ-UXMRNZNESA-N 3-[[(2s)-5-amino-5-oxo-2-[4-(pyridin-2-ylamino)butanoylamino]pentanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCC(=O)N)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCNC1=CC=CC=N1 ARAXKGCCMWKXJQ-UXMRNZNESA-N 0.000 description 1
NDDZONOAMPYGAV-CDRRMRQFSA-N 3-[[(2s)-6-(phenylmethoxycarbonylamino)-2-[5-(pyridin-2-ylamino)pentanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)NC(CC(=O)O)C=1C=CC(=CC=1)C=1C=CC=CC=1)NC(=O)CCCCNC=1N=CC=CC=1)CCCNC(=O)OCC1=CC=CC=C1 NDDZONOAMPYGAV-CDRRMRQFSA-N 0.000 description 1
OEIRAAZJDJMYOR-XLTVJXRZSA-N 3-[[(2s)-6-acetamido-2-[5-(pyridin-2-ylamino)pentanoylamino]hexanoyl]amino]-3-(4-phenylphenyl)propanoic acid Chemical compound N([C@@H](CCCCNC(=O)C)C(=O)NC(CC(O)=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C(=O)CCCCNC1=CC=CC=N1 OEIRAAZJDJMYOR-XLTVJXRZSA-N 0.000 description 1
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000004580 4,5-dihydroimidazol-2-yl group Chemical group N1C(=NCC1)* 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
108010064733 Angiotensins Proteins 0.000 description 1
102000015427 Angiotensins Human genes 0.000 description 1
102100031323 Anthrax toxin receptor 1 Human genes 0.000 description 1
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
102000016289 Cell Adhesion Molecules Human genes 0.000 description 1
108010067225 Cell Adhesion Molecules Proteins 0.000 description 1
108010069514 Cyclic Peptides Proteins 0.000 description 1
102000001189 Cyclic Peptides Human genes 0.000 description 1
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
108700021041 Disintegrin Proteins 0.000 description 1
240000006890 Erythroxylum coca Species 0.000 description 1
108010049003 Fibrinogen Proteins 0.000 description 1
102000008946 Fibrinogen Human genes 0.000 description 1
108010012088 Fibrinogen Receptors Proteins 0.000 description 1
206010018338 Glioma Diseases 0.000 description 1
101001015064 Homo sapiens Integrin beta-6 Proteins 0.000 description 1
108010040765 Integrin alphaV Proteins 0.000 description 1
102100033011 Integrin beta-6 Human genes 0.000 description 1
102000017347 Integrin beta-6 subunit Human genes 0.000 description 1
102400000401 Latency-associated peptide Human genes 0.000 description 1
102000002274 Matrix Metalloproteinases Human genes 0.000 description 1
108010000684 Matrix Metalloproteinases Proteins 0.000 description 1
102000018697 Membrane Proteins Human genes 0.000 description 1
108010052285 Membrane Proteins Proteins 0.000 description 1
108010038807 Oligopeptides Proteins 0.000 description 1
102000015636 Oligopeptides Human genes 0.000 description 1
208000004179 Oral Leukoplakia Diseases 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
241000243142 Porifera Species 0.000 description 1
241000288906 Primates Species 0.000 description 1
101710194807 Protective antigen Proteins 0.000 description 1
102000001708 Protein Isoforms Human genes 0.000 description 1
108010029485 Protein Isoforms Proteins 0.000 description 1
208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 description 1
101000815632 Streptococcus suis (strain 05ZYH33) Rqc2 homolog RqcH Proteins 0.000 description 1
102000004887 Transforming Growth Factor beta Human genes 0.000 description 1
108090001012 Transforming Growth Factor beta Proteins 0.000 description 1
108010048673 Vitronectin Receptors Proteins 0.000 description 1
239000003875 Wang resin Substances 0.000 description 1
NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
102000019997 adhesion receptor Human genes 0.000 description 1
108010013985 adhesion receptor Proteins 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000005103 alkyl silyl group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
108010039069 anthrax toxin receptors Proteins 0.000 description 1
230000002001 anti-metastasis Effects 0.000 description 1
239000002257 antimetastatic agent Substances 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
238000003782 apoptosis assay Methods 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000008468 bone growth Effects 0.000 description 1
210000002805 bone matrix Anatomy 0.000 description 1
BEWYHVAWEKZDPP-UHFFFAOYSA-N bornane Chemical compound C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 description 1
229930006742 bornane Natural products 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
230000012292 cell migration Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
230000008614 cellular interaction Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
235000008957 cocaer Nutrition 0.000 description 1
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
238000004891 communication Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000001086 cytosolic effect Effects 0.000 description 1
230000006378 damage Effects 0.000 description 1
101150047356 dec-1 gene Proteins 0.000 description 1
238000013461 design Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
210000002889 endothelial cell Anatomy 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
210000002744 extracellular matrix Anatomy 0.000 description 1
230000001605 fetal effect Effects 0.000 description 1
229940012952 fibrinogen Drugs 0.000 description 1
102000036072 fibronectin binding proteins Human genes 0.000 description 1
238000009472 formulation Methods 0.000 description 1
210000004392 genitalia Anatomy 0.000 description 1
230000012010 growth Effects 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
230000023597 hemostasis Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000002519 immonomodulatory effect Effects 0.000 description 1
230000037189 immune system physiology Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
210000004347 intestinal mucosa Anatomy 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
230000009545 invasion Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000029774 keratinocyte migration Effects 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
238000011813 knockout mouse model Methods 0.000 description 1
238000003771 laboratory diagnosis Methods 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
230000036212 malign transformation Effects 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
210000004379 membrane Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
102000006240 membrane receptors Human genes 0.000 description 1
108020004084 membrane receptors Proteins 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
108020004999 messenger RNA Proteins 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
210000000214 mouth Anatomy 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000009826 neoplastic cell growth Effects 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
201000008557 oral mucosa leukoplakia Diseases 0.000 description 1
201000002740 oral squamous cell carcinoma Diseases 0.000 description 1
210000002997 osteoclast Anatomy 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
229930004008 p-menthane Natural products 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229930006728 pinane Natural products 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
230000005522 programmed cell death Effects 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
230000002633 protecting effect Effects 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000007634 remodeling Methods 0.000 description 1
230000008439 repair process Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
230000011664 signaling Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
235000012461 sponges Nutrition 0.000 description 1
230000007480 spreading Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
210000000434 stratum corneum Anatomy 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DVFXLNFDWATPMW-IWOKLKJTSA-N tert-butyldiphenylsilyl Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C(C)(C)C)[C@@H](OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)OP(O)(=O)OC[C@@H]2[C@H](CC(O2)N2C3=NC=NC(N)=C3N=C2)OP(O)(=O)OC[C@@H]2[C@H](C[C@@H](O2)N2C3=C(C(NC(N)=N3)=O)N=C2)O)C1 DVFXLNFDWATPMW-IWOKLKJTSA-N 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000005167 vascular cell Anatomy 0.000 description 1
230000037314 wound repair Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Diabetes (AREA)
Physical Education & Sports Medicine (AREA)
Virology (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Urology & Nephrology (AREA)
Dermatology (AREA)
Hematology (AREA)
Ophthalmology & Optometry (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Biomedical Technology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Neurosurgery (AREA)
Emergency Medicine (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Obesity (AREA)
Gastroenterology & Hepatology (AREA)

ZA200308024A 2001-03-16 2003-10-15 Inhibitors of integrin alphavbeta6. ZA200308024B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10112771A DE10112771A1 (de)	2001-03-16	2001-03-16	Inhibitoren des Integrins alpha¶v¶beta¶6¶

Publications (1)

Publication Number	Publication Date
ZA200308024B true ZA200308024B (en)	2005-01-17

Family

ID=7677763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200308024A ZA200308024B (en)	2001-03-16	2003-10-15	Inhibitors of integrin alphavbeta6.

Country Status (13)

Country	Link
US (1)	US7632951B2 (de)
EP (1)	EP1377540B1 (de)
JP (1)	JP4327461B2 (de)
CN (1)	CN1582271A (de)
AT (1)	ATE416157T1 (de)
AU (1)	AU2002254900B2 (de)
CA (1)	CA2440644C (de)
DE (2)	DE10112771A1 (de)
ES (1)	ES2316556T3 (de)
HU (1)	HUP0303514A2 (de)
MX (1)	MXPA03008215A (de)
WO (1)	WO2002074730A1 (de)
ZA (1)	ZA200308024B (de)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1641759B1 (de) *	2003-07-07	2014-03-12	Merck Patent GmbH	Malonamidderivate
ATE399542T1 (de) *	2003-10-01	2008-07-15	Merck Patent Gmbh	Alfavbeta3 und alfavbeta6 integrin antagonisten als antifibrotische mittel
JP4634303B2 (ja) *	2003-10-10	2011-02-16	興和株式会社	血管新生抑制薬
AU2005251745A1 (en)	2004-06-04	2005-12-22	The Regents Of The University Of California	Compounds having activity in increasing ion transport by mutant-CFTR and uses thereof
US7838252B2 (en) *	2005-02-17	2010-11-23	The Board Of Trustees Of The Leland Stanford Junior University	Methods and compositions for treating a subject having an anthrax toxin mediated condition
WO2009048541A2 (en) *	2007-10-05	2009-04-16	Purdue Research Foundation	Compounds and methods for use in treating neoplasia and cancer
WO2009051910A1 (en) *	2007-10-16	2009-04-23	The Regents Of The University Of California	Compounds having activity in increasing ion transport by mutant-cftr and uses thereof
EP2730282A1 (de)	2007-11-08	2014-05-14	The General Hospital Corporation	Verfahren und Zusammensetzung zur Behandlung von Proteinurie-Erkrankungen
GB0922014D0 (en) *	2009-12-17	2010-02-03	Ge Healthcare Ltd	Novel integrin binders
WO2013016531A2 (en) *	2011-07-26	2013-01-31	Purdue Research Foundation	Compounds and methods for use in treating neoplasia and cancer
GB201305668D0 (en) *	2013-03-28	2013-05-15	Glaxosmithkline Ip Dev Ltd	Avs6 Integrin Antagonists
WO2015179823A2 (en) *	2014-05-23	2015-11-26	The California Institute For Biomedical Research	Lung localized inhibitors of alpha(v)beta 6
GB201417018D0 (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
GB201417094D0 (en)	2014-09-26	2014-11-12	Glaxosmithkline Ip Dev Ltd	Novel compounds
GB201417011D0 (en)	2014-09-26	2014-11-12	Glaxosmithkline Ip Dev Ltd	Novel compounds
WO2016154369A1 (en) *	2015-03-26	2016-09-29	Merck Sharp & Dohme Corp.	Composition and methods for treating chronic kidney disease
GB201604680D0 (en)	2016-03-21	2016-05-04	Glaxosmithkline Ip Dev Ltd	Chemical Compounds
US10696672B2 (en)	2016-12-23	2020-06-30	Pliant Therapeutics, Inc.	Amino acid compounds and methods of use
MA52117A (fr)	2017-02-28	2022-04-06	Morphic Therapeutic Inc	Inhibiteurs de l'intégrine (alpha-v) (bêta-6)
MX394210B (es)	2017-02-28	2025-03-04	Morphic Therapeutic Inc	INHIBIDORES DE INTEGRINA AVß6.
WO2019089765A1 (en) *	2017-11-01	2019-05-09	Arrowhead Pharmcaceuticals, Inc.	Integrin ligands and uses thereof
WO2020047208A1 (en)	2018-08-29	2020-03-05	Morphic Therapeutic, Inc.	Inhibitors of (alpha-v)(beta-6) integrin
WO2020047239A1 (en)	2018-08-29	2020-03-05	Morphic Therapeutic, Inc.	INHIBITING αV β6 INTEGRIN
SI3844162T1 (sl)	2018-08-29	2025-06-30	Morphic Therapeutic, Inc.	Zaviralci integrina alfa v beta6
US20240209034A1 (en) *	2021-04-12	2024-06-27	University Of Washington	Engineering peptides for a a vb6 integrin binding and related methods of use and synthesis
CN121335883A (zh) *	2023-04-17	2026-01-13	埃沃特克国际有限责任公司	作为α4β7抑制剂的新型化合物
CN120309684A (zh) *	2024-01-15	2025-07-15	武汉人福创新药物研发中心有限公司	靶向化合物及其用途

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6306840B1 (en) *	1995-01-23	2001-10-23	Biogen, Inc.	Cell adhesion inhibitors
PL350057A1 (en) *	1999-02-20	2002-11-04	Merck Patent Gmbh	β-ALANINE DERIVATIVES
DE10041423A1 (de)	2000-08-23	2002-03-07	Merck Patent Gmbh	Biphenylderivate
DE10204789A1 (de) *	2002-02-06	2003-08-14	Merck Patent Gmbh	Inhibitoren des Integrins alpha¶v¶beta6

2001
- 2001-03-16 DE DE10112771A patent/DE10112771A1/de not_active Withdrawn
2002
- 2002-02-21 HU HU0303514A patent/HUP0303514A2/hu unknown
- 2002-02-21 EP EP02724175A patent/EP1377540B1/de not_active Expired - Lifetime
- 2002-02-21 WO PCT/EP2002/001836 patent/WO2002074730A1/en not_active Ceased
- 2002-02-21 US US10/471,836 patent/US7632951B2/en not_active Expired - Fee Related
- 2002-02-21 CA CA2440644A patent/CA2440644C/en not_active Expired - Fee Related
- 2002-02-21 JP JP2002573739A patent/JP4327461B2/ja not_active Expired - Fee Related
- 2002-02-21 MX MXPA03008215A patent/MXPA03008215A/es unknown
- 2002-02-21 AU AU2002254900A patent/AU2002254900B2/en not_active Ceased
- 2002-02-21 AT AT02724175T patent/ATE416157T1/de not_active IP Right Cessation
- 2002-02-21 ES ES02724175T patent/ES2316556T3/es not_active Expired - Lifetime
- 2002-02-21 CN CNA028067061A patent/CN1582271A/zh active Pending
- 2002-02-21 DE DE60230127T patent/DE60230127D1/de not_active Expired - Lifetime
2003
- 2003-10-15 ZA ZA200308024A patent/ZA200308024B/en unknown

Also Published As

Publication number	Publication date
MXPA03008215A (es)	2004-01-29
DE60230127D1 (de)	2009-01-15
JP2004525925A (ja)	2004-08-26
US20040092454A1 (en)	2004-05-13
DE10112771A1 (de)	2002-09-26
CA2440644A1 (en)	2002-09-26
AU2002254900B2 (en)	2008-04-10
EP1377540B1 (de)	2008-12-03
EP1377540A1 (de)	2004-01-07
CN1582271A (zh)	2005-02-16
HUP0303514A2 (hu)	2004-01-28
CA2440644C (en)	2011-10-18
ATE416157T1 (de)	2008-12-15
ES2316556T3 (es)	2009-04-16
US7632951B2 (en)	2009-12-15
JP4327461B2 (ja)	2009-09-09
WO2002074730A1 (en)	2002-09-26

Publication	Publication Date	Title
ZA200308024B (en)	2005-01-17	Inhibitors of integrin alphavbeta6.
AU2002254900A1 (en)	2003-03-27	Inhibitors of integrin AlphavBeta6
US7138417B2 (en)	2006-11-21	Inhibitors of integrin αvβ6
EP1343764B1 (de)	2004-08-25	Harnstoff- und urethanderivate als integrin inhibitoren
US20040142877A1 (en)	2004-07-22	Ligands of the $g(a)v$g(b)6 integrin
ZA200302256B (en)	2004-07-26	Biphenyl derivatives and the use thereof as integrin inhibitors.
US20030187289A1 (en)	2003-10-02	Biphenyl derivatives and the use thereof as integrin inhibitors