NO329742B1 - Substituerte metylenamidderivater, anvendelse av metylenamidderivatene for fremstilling av medikamenter og farmasoytiske sammensetninger, farmasoytiske sammensetninger som innholder metylenamidderivatene og fremgangsmater for fremstilling av de substituerte mtylenamidderivatene - Google Patents
Substituerte metylenamidderivater, anvendelse av metylenamidderivatene for fremstilling av medikamenter og farmasoytiske sammensetninger, farmasoytiske sammensetninger som innholder metylenamidderivatene og fremgangsmater for fremstilling av de substituerte mtylenamidderivatene Download PDFInfo
- Publication number
- NO329742B1 NO329742B1 NO20043520A NO20043520A NO329742B1 NO 329742 B1 NO329742 B1 NO 329742B1 NO 20043520 A NO20043520 A NO 20043520A NO 20043520 A NO20043520 A NO 20043520A NO 329742 B1 NO329742 B1 NO 329742B1
- Authority
- NO
- Norway
- Prior art keywords
- amino
- benzyl
- oxo
- acetic acid
- carbonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 273
- 238000002360 preparation method Methods 0.000 title claims abstract description 239
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical class N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 title claims abstract description 78
- 239000003814 drug Substances 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 30
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 27
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 26
- 208000008589 Obesity Diseases 0.000 claims abstract description 17
- 235000020824 obesity Nutrition 0.000 claims abstract description 17
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims abstract description 16
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 14
- 239000008103 glucose Substances 0.000 claims abstract description 14
- 230000000694 effects Effects 0.000 claims abstract description 13
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 6
- 208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 6
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 6
- -1 cyano, hydroxy, mercapto Chemical class 0.000 claims description 406
- 150000001875 compounds Chemical class 0.000 claims description 333
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 168
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 158
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 153
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 142
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 113
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 31
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 26
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 125000006239 protecting group Chemical group 0.000 claims description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 20
- 239000004305 biphenyl Chemical group 0.000 claims description 20
- 125000001544 thienyl group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 15
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 239000005711 Benzoic acid Substances 0.000 claims description 11
- 235000010233 benzoic acid Nutrition 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 10
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 10
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000006267 biphenyl group Chemical group 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 8
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- SLXTWXQUEZSSTJ-UHFFFAOYSA-N 6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1(C=2N=CC(=CC=2)C(O)=O)CC1 SLXTWXQUEZSSTJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 201000001421 hyperglycemia Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 6
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 229960000281 trometamol Drugs 0.000 claims description 5
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 4
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000003431 oxalo group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 150000007854 aminals Chemical class 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 125000002958 pentadecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 150000003555 thioacetals Chemical class 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- GIYSNBAGZMHXBD-UHFFFAOYSA-N 2-[4-(dodecylcarbamoyl)-n-[(2-methoxycarbonylphenyl)methyl]anilino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1N(C(=O)C(O)=O)CC1=CC=CC=C1C(=O)OC GIYSNBAGZMHXBD-UHFFFAOYSA-N 0.000 claims description 2
- SACDNBISSDLRJL-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[(4-iodophenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC(Br)=C1CN(C(=O)C(O)=O)CC1=CC=C(I)C=C1 SACDNBISSDLRJL-UHFFFAOYSA-N 0.000 claims description 2
- ANHLFBREFORGGL-UHFFFAOYSA-N 2-[benzyl-[[4-[dodecyl(methyl)carbamoyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)N(C)CCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1 ANHLFBREFORGGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 235000021229 appetite regulation Nutrition 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 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 claims description 2
- GXADYWWQURNZLE-UHFFFAOYSA-N 2-[(4-dec-1-ynylphenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 GXADYWWQURNZLE-UHFFFAOYSA-N 0.000 claims 4
- 125000006481 2-iodobenzyl group Chemical group [H]C1=C([H])C(I)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- RBGXSZACMCUXDN-UHFFFAOYSA-N 2-[(3,5-dichlorophenyl)methyl-[[4-(tridecanoylamino)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(NC(=O)CCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC(Cl)=CC(Cl)=C1 RBGXSZACMCUXDN-UHFFFAOYSA-N 0.000 claims 2
- LDGBYTHFGXYESV-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl-[(4-dec-1-ynylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC(Cl)=C1 LDGBYTHFGXYESV-UHFFFAOYSA-N 0.000 claims 2
- HZFAXULAQMUCMO-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C=C(Cl)C=CC=3)C(=O)C(O)=O)=CC=2)=N1 HZFAXULAQMUCMO-UHFFFAOYSA-N 0.000 claims 2
- QQCNLKLBUUJHNN-UHFFFAOYSA-N 2-[(4-dec-1-ynylnaphthalen-1-yl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C12=CC=CC=C2C(C#CCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 QQCNLKLBUUJHNN-UHFFFAOYSA-N 0.000 claims 2
- VIWJRYWUCVSZRN-UHFFFAOYSA-N 2-[(4-dodecoxynaphthalen-1-yl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C12=CC=CC=C2C(OCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 VIWJRYWUCVSZRN-UHFFFAOYSA-N 0.000 claims 2
- YTEKIWCHDJVHMJ-UHFFFAOYSA-N 2-[(4-dodecylphenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 YTEKIWCHDJVHMJ-UHFFFAOYSA-N 0.000 claims 2
- PJYWPFIWBMEOOK-UHFFFAOYSA-N 2-[(4-octoxyphenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 PJYWPFIWBMEOOK-UHFFFAOYSA-N 0.000 claims 2
- DLYCADZOXBEKSO-UHFFFAOYSA-N 2-[1-[4-(dodecylcarbamoyl)phenyl]ethyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1C(C)N(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 DLYCADZOXBEKSO-UHFFFAOYSA-N 0.000 claims 2
- BTGJVYOHBIOMKK-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)ethyl-[(4-dodec-1-ynylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC(Cl)=C1 BTGJVYOHBIOMKK-UHFFFAOYSA-N 0.000 claims 2
- AXHBAIVLWPDEOY-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)ethyl-[(4-oct-1-ynylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC(Cl)=C1 AXHBAIVLWPDEOY-UHFFFAOYSA-N 0.000 claims 2
- RZZIKQOCRPBOKW-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)ethyl-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(CCC=3C=C(Cl)C=CC=3)C(=O)C(O)=O)=CC=2)=N1 RZZIKQOCRPBOKW-UHFFFAOYSA-N 0.000 claims 2
- CBKVGUUFNMOQCO-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)ethyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CCC=3C=C(Cl)C=CC=3)C(=O)C(O)=O)=CC=2)=N1 CBKVGUUFNMOQCO-UHFFFAOYSA-N 0.000 claims 2
- SVJNQETZYZCONZ-UHFFFAOYSA-N 2-[[1-(4-octylbenzoyl)piperidin-4-yl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1C(=O)N1CCC(CN(CC=2C=CC(=CC=2)C(F)(F)F)C(=O)C(O)=O)CC1 SVJNQETZYZCONZ-UHFFFAOYSA-N 0.000 claims 2
- GLJQFJZILCHRPC-UHFFFAOYSA-N 2-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=N1 GLJQFJZILCHRPC-UHFFFAOYSA-N 0.000 claims 2
- MZBSKTMATWHSRX-UHFFFAOYSA-N 2-[[4-[(4-octylbenzoyl)amino]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1C(=O)NC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 MZBSKTMATWHSRX-UHFFFAOYSA-N 0.000 claims 2
- UDGPVEVIOSLBFV-UHFFFAOYSA-N 2-[[4-[2-(3-octyl-1,2,4-oxadiazol-5-yl)ethyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(CCC=2C=CC(CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=N1 UDGPVEVIOSLBFV-UHFFFAOYSA-N 0.000 claims 2
- XWEDCFRXPKNCFN-UHFFFAOYSA-N 2-[[4-[2-(4-hexylphenyl)ethyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCC)=CC=C1CCC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 XWEDCFRXPKNCFN-UHFFFAOYSA-N 0.000 claims 2
- NWAHBKILAVNPFN-UHFFFAOYSA-N 2-[[4-[2-(4-hexylphenyl)ethynyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCC)=CC=C1C#CC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 NWAHBKILAVNPFN-UHFFFAOYSA-N 0.000 claims 2
- FEAIVHWISJQSHE-UHFFFAOYSA-N 2-[[cyclopentyl-[4-(trifluoromethyl)phenyl]methyl]-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(C(C3CCCC3)C=3C=CC(=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=N1 FEAIVHWISJQSHE-UHFFFAOYSA-N 0.000 claims 2
- HRHDYNGGLNBCBM-UHFFFAOYSA-N 2-[n-[(4-dodec-1-ynylphenyl)methyl]-4-(trifluoromethyl)anilino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)C1=CC=C(C(F)(F)F)C=C1 HRHDYNGGLNBCBM-UHFFFAOYSA-N 0.000 claims 2
- XOWSYVQYHPTSGW-UHFFFAOYSA-N 2-oxo-2-[2-[4-(trifluoromethyl)phenyl]propan-2-yl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]acetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(C(=O)C(O)=O)C(C)(C)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)=N1 XOWSYVQYHPTSGW-UHFFFAOYSA-N 0.000 claims 2
- ZHUMWUSIWQXTSQ-UHFFFAOYSA-N 2-oxo-2-[[4-(trifluoromethyl)phenyl]methyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)naphthalen-1-yl]methyl]amino]acetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C3=CC=CC=C3C(CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=N1 ZHUMWUSIWQXTSQ-UHFFFAOYSA-N 0.000 claims 2
- GLJMZTUTZOFEDJ-UHFFFAOYSA-N 2-oxo-2-[[4-(trifluoromethyl)phenyl]methyl-[[4-[2-(3-undecyl-1,2,4-oxadiazol-5-yl)ethyl]phenyl]methyl]amino]acetic acid Chemical compound CCCCCCCCCCCC1=NOC(CCC=2C=CC(CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=N1 GLJMZTUTZOFEDJ-UHFFFAOYSA-N 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 2
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- LJZSXYPLOATEFB-UHFFFAOYSA-N 11-[4-[[oxalo-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]phenyl]undec-10-ynoic acid Chemical compound C1=CC(C#CCCCCCCCCC(=O)O)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 LJZSXYPLOATEFB-UHFFFAOYSA-N 0.000 claims 1
- AHPFWFWNZWBTJU-UHFFFAOYSA-N 11-[4-[[oxalo-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]phenyl]undecanoic acid Chemical compound C1=CC(CCCCCCCCCCC(=O)O)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 AHPFWFWNZWBTJU-UHFFFAOYSA-N 0.000 claims 1
- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- FLOGMJXZWICQJI-UHFFFAOYSA-N 2-[(2-dec-1-ynylphenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC#CC1=CC=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 FLOGMJXZWICQJI-UHFFFAOYSA-N 0.000 claims 1
- OPROHMRMQPERQH-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl-[[3-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=C(CN(CC=3C(=CC=CC=3)OC)C(=O)C(O)=O)C=CC=2)=N1 OPROHMRMQPERQH-UHFFFAOYSA-N 0.000 claims 1
- DMRMEXGVRWCBJG-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C(=CC=CC=3)OC)C(=O)C(O)=O)=CC=2)=N1 DMRMEXGVRWCBJG-UHFFFAOYSA-N 0.000 claims 1
- LNGCCQGQZMAVHM-UHFFFAOYSA-N 2-[(2-methoxyphenyl)methyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C(=CC=CC=3)OC)C(=O)C(O)=O)=CC=2)=N1 LNGCCQGQZMAVHM-UHFFFAOYSA-N 0.000 claims 1
- YRGBCWCDMFYDBL-UHFFFAOYSA-N 2-[(3,5-dichlorophenyl)methyl-[[4-[2-(4-phenylphenyl)ethylcarbamoyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C(Cl)=CC(Cl)=CC=1CN(C(=O)C(=O)O)CC(C=C1)=CC=C1C(=O)NCCC(C=C1)=CC=C1C1=CC=CC=C1 YRGBCWCDMFYDBL-UHFFFAOYSA-N 0.000 claims 1
- VTJWHBBWMSLPBI-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl-[[5-(3,3-diphenylpropylsulfamoyl)thiophen-2-yl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=CC(Cl)=CC=1CN(C(=O)C(=O)O)CC(S1)=CC=C1S(=O)(=O)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 VTJWHBBWMSLPBI-UHFFFAOYSA-N 0.000 claims 1
- UXDRBFWUTSMYIO-UHFFFAOYSA-N 2-[(3-cyanophenyl)methyl-[[4-[3-(2,2-diphenylethylcarbamoyl)phenyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=CC(C#N)=CC=1CN(C(=O)C(=O)O)CC(C=C1)=CC=C1C(C=1)=CC=CC=1C(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 UXDRBFWUTSMYIO-UHFFFAOYSA-N 0.000 claims 1
- OKLKZPMMEUTLRC-UHFFFAOYSA-N 2-[(3-cyanophenyl)methyl-[[4-[3-(3-phenylpropylcarbamoyl)phenyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=CC(C#N)=CC=1CN(C(=O)C(=O)O)CC(C=C1)=CC=C1C(C=1)=CC=CC=1C(=O)NCCCC1=CC=CC=C1 OKLKZPMMEUTLRC-UHFFFAOYSA-N 0.000 claims 1
- DJEJYFBSXQKZTC-UHFFFAOYSA-N 2-[(3-cyanophenyl)methyl-[[4-[3-(dodecylcarbamoyl)phenyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC(C=2C=CC(CN(CC=3C=C(C=CC=3)C#N)C(=O)C(O)=O)=CC=2)=C1 DJEJYFBSXQKZTC-UHFFFAOYSA-N 0.000 claims 1
- FUFARIZFGMIJKI-UHFFFAOYSA-N 2-[(3-cyanophenyl)methyl-[[4-[3-(octylcarbamoyl)phenyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCNC(=O)C1=CC=CC(C=2C=CC(CN(CC=3C=C(C=CC=3)C#N)C(=O)C(O)=O)=CC=2)=C1 FUFARIZFGMIJKI-UHFFFAOYSA-N 0.000 claims 1
- WJNBDTDWDPUFJF-UHFFFAOYSA-N 2-[(3-dec-1-ynyl-1-benzofuran-5-yl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=C2C(C#CCCCCCCCC)=COC2=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 WJNBDTDWDPUFJF-UHFFFAOYSA-N 0.000 claims 1
- ZTANRILDLXIPJX-UHFFFAOYSA-N 2-[(3-dodec-1-ynyl-1-benzofuran-5-yl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=C2C(C#CCCCCCCCCCC)=COC2=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 ZTANRILDLXIPJX-UHFFFAOYSA-N 0.000 claims 1
- QQGSQQDGUATWGJ-UHFFFAOYSA-N 2-[(3-dodec-1-ynylphenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCC#CC1=CC=CC(CN(CC=2C=CC(=CC=2)C(F)(F)F)C(=O)C(O)=O)=C1 QQGSQQDGUATWGJ-UHFFFAOYSA-N 0.000 claims 1
- QEFGLGISUDUOQS-UHFFFAOYSA-N 2-[(4-bromophenyl)methyl-[(4-oct-1-ynylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(Br)C=C1 QEFGLGISUDUOQS-UHFFFAOYSA-N 0.000 claims 1
- HUHHBFNLLSWYST-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl-[[4-[3-(2,2-diphenylethylcarbamoyl)phenyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=C(C=2C=C(C=CC=2)C(=O)NCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1CN(C(=O)C(=O)O)CC1=CC=C(Cl)C=C1 HUHHBFNLLSWYST-UHFFFAOYSA-N 0.000 claims 1
- XHPNCJJQAMVIFJ-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl-[[4-[3-(dodecylcarbamoyl)phenyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC(C=2C=CC(CN(CC=3C=CC(Cl)=CC=3)C(=O)C(O)=O)=CC=2)=C1 XHPNCJJQAMVIFJ-UHFFFAOYSA-N 0.000 claims 1
- XRZVCTVTMKLLCK-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl-[[4-[3-(octylcarbamoyl)phenyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCNC(=O)C1=CC=CC(C=2C=CC(CN(CC=3C=CC(Cl)=CC=3)C(=O)C(O)=O)=CC=2)=C1 XRZVCTVTMKLLCK-UHFFFAOYSA-N 0.000 claims 1
- BUZMULQKYJZENH-UHFFFAOYSA-N 2-[(4-dec-1-ynylphenyl)methyl-[2-(2-fluorophenyl)ethyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC=C1F BUZMULQKYJZENH-UHFFFAOYSA-N 0.000 claims 1
- CQOXRYXJDZCBRU-UHFFFAOYSA-N 2-[(4-dec-1-ynylphenyl)methyl-[2-(3,4-dichlorophenyl)ethyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=C(Cl)C(Cl)=C1 CQOXRYXJDZCBRU-UHFFFAOYSA-N 0.000 claims 1
- NKTWUXQNHHTFLY-UHFFFAOYSA-N 2-[(4-dec-1-ynylphenyl)methyl-[[2-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1C(F)(F)F NKTWUXQNHHTFLY-UHFFFAOYSA-N 0.000 claims 1
- IQMKGHOKIYBUBW-UHFFFAOYSA-N 2-[(4-dodec-1-ynylnaphthalen-1-yl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C12=CC=CC=C2C(C#CCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 IQMKGHOKIYBUBW-UHFFFAOYSA-N 0.000 claims 1
- IGMGHQLOMREYTO-UHFFFAOYSA-N 2-[(4-dodec-1-ynylphenyl)methyl-[(4-fluorophenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(F)C=C1 IGMGHQLOMREYTO-UHFFFAOYSA-N 0.000 claims 1
- ZLHWBHAOLBSKTE-UHFFFAOYSA-N 2-[(4-dodec-1-ynylphenyl)methyl-[2-(2-fluorophenyl)ethyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC=C1F ZLHWBHAOLBSKTE-UHFFFAOYSA-N 0.000 claims 1
- OFDPVLHTJQJUSM-UHFFFAOYSA-N 2-[(4-dodec-1-ynylphenyl)methyl-[[2-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1C(F)(F)F OFDPVLHTJQJUSM-UHFFFAOYSA-N 0.000 claims 1
- IIRDWUFDUKIAQO-UHFFFAOYSA-N 2-[(4-dodecoxynaphthalen-1-yl)methyl-[2-(2-fluorophenyl)ethyl]amino]-2-oxoacetic acid Chemical compound C12=CC=CC=C2C(OCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC=C1F IIRDWUFDUKIAQO-UHFFFAOYSA-N 0.000 claims 1
- IXSJKAJINKFVDU-UHFFFAOYSA-N 2-[(4-dodecoxynaphthalen-1-yl)methyl-[[2-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C12=CC=CC=C2C(OCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1C(F)(F)F IXSJKAJINKFVDU-UHFFFAOYSA-N 0.000 claims 1
- POEMXMURDLCFDH-UHFFFAOYSA-N 2-[(4-oct-1-ynylphenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 POEMXMURDLCFDH-UHFFFAOYSA-N 0.000 claims 1
- IJOGKIFRKSWELU-UHFFFAOYSA-N 2-[(4-octoxyphenyl)methyl-[[2-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1C(F)(F)F IJOGKIFRKSWELU-UHFFFAOYSA-N 0.000 claims 1
- TVOPLKCKQZTIII-UHFFFAOYSA-N 2-[(6-dodec-1-ynylpyridin-3-yl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=NC(C#CCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 TVOPLKCKQZTIII-UHFFFAOYSA-N 0.000 claims 1
- ATUXGXZPOYRNHM-UHFFFAOYSA-N 2-[1,3-benzodioxol-5-yl-[[3-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=C(CN(C(=O)C(O)=O)C=3C=C4OCOC4=CC=3)C=CC=2)=N1 ATUXGXZPOYRNHM-UHFFFAOYSA-N 0.000 claims 1
- QUXMHSNKYOAQJQ-UHFFFAOYSA-N 2-[1,3-benzodioxol-5-yl-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(C(=O)C(O)=O)C=3C=C4OCOC4=CC=3)=CC=2)=N1 QUXMHSNKYOAQJQ-UHFFFAOYSA-N 0.000 claims 1
- LNQFCBSIYYHJMX-UHFFFAOYSA-N 2-[1,3-benzodioxol-5-yl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(C(=O)C(O)=O)C=3C=C4OCOC4=CC=3)=CC=2)=N1 LNQFCBSIYYHJMX-UHFFFAOYSA-N 0.000 claims 1
- XZTAFXGSZGNIIU-UHFFFAOYSA-N 2-[1-benzothiophen-3-ylmethyl-[[3-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=C(CN(CC=3C4=CC=CC=C4SC=3)C(=O)C(O)=O)C=CC=2)=N1 XZTAFXGSZGNIIU-UHFFFAOYSA-N 0.000 claims 1
- OYZKGECBPALYOL-UHFFFAOYSA-N 2-[1-benzothiophen-3-ylmethyl-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C4=CC=CC=C4SC=3)C(=O)C(O)=O)=CC=2)=N1 OYZKGECBPALYOL-UHFFFAOYSA-N 0.000 claims 1
- QYJQCOUVVPJSOC-UHFFFAOYSA-N 2-[1-benzothiophen-3-ylmethyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C4=CC=CC=C4SC=3)C(=O)C(O)=O)=CC=2)=N1 QYJQCOUVVPJSOC-UHFFFAOYSA-N 0.000 claims 1
- KXEXRDJCQVNXQT-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)ethyl-[(4-octoxyphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC=C1F KXEXRDJCQVNXQT-UHFFFAOYSA-N 0.000 claims 1
- WNJOFKAAEKGDKD-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)ethyl-[[3-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=C(CN(CCC=3C(=CC=CC=3)F)C(=O)C(O)=O)C=CC=2)=N1 WNJOFKAAEKGDKD-UHFFFAOYSA-N 0.000 claims 1
- ODFNPHVWFFAQAO-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)ethyl-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(CCC=3C(=CC=CC=3)F)C(=O)C(O)=O)=CC=2)=N1 ODFNPHVWFFAQAO-UHFFFAOYSA-N 0.000 claims 1
- HJTHSPVKNUHHET-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)ethyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CCC=3C(=CC=CC=3)F)C(=O)C(O)=O)=CC=2)=N1 HJTHSPVKNUHHET-UHFFFAOYSA-N 0.000 claims 1
- BKAHQDBARANLIX-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)ethyl-[(4-octoxyphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=C(Cl)C(Cl)=C1 BKAHQDBARANLIX-UHFFFAOYSA-N 0.000 claims 1
- UTGAOOFPBDBGSZ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)ethyl-[[3-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=C(CN(CCC=3C=C(Cl)C(Cl)=CC=3)C(=O)C(O)=O)C=CC=2)=N1 UTGAOOFPBDBGSZ-UHFFFAOYSA-N 0.000 claims 1
- RYALQRJCWKTSGI-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)ethyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CCC=3C=C(Cl)C(Cl)=CC=3)C(=O)C(O)=O)=CC=2)=N1 RYALQRJCWKTSGI-UHFFFAOYSA-N 0.000 claims 1
- GZENBTXITIJEHG-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)ethyl-[(4-dec-1-ynylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC(Cl)=C1 GZENBTXITIJEHG-UHFFFAOYSA-N 0.000 claims 1
- BMPKTMUWFKVWLS-UHFFFAOYSA-N 2-[4-dibenzofuran-4-yl-n-[[4-(trifluoromethyl)phenyl]methyl]anilino]-2-oxoacetic acid Chemical compound C=1C=C(C=2C3=C(C4=CC=CC=C4O3)C=CC=2)C=CC=1N(C(=O)C(=O)O)CC1=CC=C(C(F)(F)F)C=C1 BMPKTMUWFKVWLS-UHFFFAOYSA-N 0.000 claims 1
- SFCKIDVMBUKNIY-WZTVWXICSA-N 2-[4-dibenzofuran-4-yl-n-[[4-(trifluoromethyl)phenyl]methyl]anilino]-2-oxoacetic acid;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C=1C=C(C=2C=3OC4=CC=CC=C4C=3C=CC=2)C=CC=1N(C(=O)C(=O)O)CC1=CC=C(C(F)(F)F)C=C1 SFCKIDVMBUKNIY-WZTVWXICSA-N 0.000 claims 1
- UHFIRJRDSGHQDB-UHFFFAOYSA-N 2-[N-[[4-(dodecylcarbamoyl)phenyl]methyl]-4-(trifluoromethyl)anilino]-2-oxoacetic acid 2-[(4-dodec-1-ynylphenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C(CCCCCCCCCCC)NC(=O)C1=CC=C(CN(C2=CC=C(C=C2)C(F)(F)F)C(C(=O)O)=O)C=C1.C(#CCCCCCCCCCC)C1=CC=C(CN(CC2=CC=C(C=C2)C(F)(F)F)C(C(=O)O)=O)C=C1 UHFIRJRDSGHQDB-UHFFFAOYSA-N 0.000 claims 1
- PYNZGJNLVSAYDA-UHFFFAOYSA-N 2-[[2,6-dibromo-4-(dodecylcarbamoyl)phenyl]methyl-[[3-(4-fluorophenyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound BrC1=CC(C(=O)NCCCCCCCCCCCC)=CC(Br)=C1CN(C(=O)C(O)=O)CC1=CC=CC(C=2C=CC(F)=CC=2)=C1 PYNZGJNLVSAYDA-UHFFFAOYSA-N 0.000 claims 1
- ABSVCSVZOMFQKX-UHFFFAOYSA-N 2-[[2,6-dibromo-4-(dodecylcarbamoyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound BrC1=CC(C(=O)NCCCCCCCCCCCC)=CC(Br)=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 ABSVCSVZOMFQKX-UHFFFAOYSA-N 0.000 claims 1
- YRWWCHFMZVZJOE-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[(2-phenylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC(Br)=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1C1=CC=CC=C1 YRWWCHFMZVZJOE-UHFFFAOYSA-N 0.000 claims 1
- LFUGXILZSCEPNZ-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[(4-phenoxyphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC(Br)=C1CN(C(=O)C(O)=O)CC(C=C1)=CC=C1OC1=CC=CC=C1 LFUGXILZSCEPNZ-UHFFFAOYSA-N 0.000 claims 1
- BVJUCQFTWLCVTH-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[[2-(trifluoromethoxy)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC(Br)=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1OC(F)(F)F BVJUCQFTWLCVTH-UHFFFAOYSA-N 0.000 claims 1
- BRWHOLHIJITTMG-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[[3-(4-fluorophenyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC(Br)=C1CN(C(=O)C(O)=O)CC1=CC=CC(C=2C=CC(F)=CC=2)=C1 BRWHOLHIJITTMG-UHFFFAOYSA-N 0.000 claims 1
- VWWVYHLYDPAUEE-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[[4-(trifluoromethoxy)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC(Br)=C1CN(C(=O)C(O)=O)CC1=CC=C(OC(F)(F)F)C=C1 VWWVYHLYDPAUEE-UHFFFAOYSA-N 0.000 claims 1
- NWAWHUUTUUMFGK-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC(Br)=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 NWAWHUUTUUMFGK-UHFFFAOYSA-N 0.000 claims 1
- KUCODPDMTQFAEK-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[2-(4-phenoxyphenyl)ethylcarbamoyl]phenyl]methyl-[(3-phenoxyphenyl)methyl]amino]-2-oxoacetic acid Chemical compound BrC=1C=C(C(=O)NCCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC(C=1)=CC=CC=1OC1=CC=CC=C1 KUCODPDMTQFAEK-UHFFFAOYSA-N 0.000 claims 1
- GIHQSEGZUBFGQP-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[2-(4-phenoxyphenyl)ethylcarbamoyl]phenyl]methyl-[[3-(4-fluorophenyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound BrC=1C=C(C(=O)NCCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC(C=1)=CC=CC=1C1=CC=C(F)C=C1 GIHQSEGZUBFGQP-UHFFFAOYSA-N 0.000 claims 1
- BUZZVNVWJSCFDB-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[2-(4-phenylphenyl)ethylcarbamoyl]phenyl]methyl-[(2-phenylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound BrC=1C=C(C(=O)NCCC=2C=CC(=CC=2)C=2C=CC=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC1=CC=CC=C1C1=CC=CC=C1 BUZZVNVWJSCFDB-UHFFFAOYSA-N 0.000 claims 1
- JXKXZKUZGPGNEG-UHFFFAOYSA-N 2-[[2,6-dibromo-4-[2-(4-phenylphenyl)ethylcarbamoyl]phenyl]methyl-[(3-phenoxyphenyl)methyl]amino]-2-oxoacetic acid Chemical compound BrC=1C=C(C(=O)NCCC=2C=CC(=CC=2)C=2C=CC=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC(C=1)=CC=CC=1OC1=CC=CC=C1 JXKXZKUZGPGNEG-UHFFFAOYSA-N 0.000 claims 1
- QNVXSPMPOWRWKJ-UHFFFAOYSA-N 2-[[2-bromo-4-(dodecylcarbamoyl)phenyl]methyl-[[3-(trifluoromethoxy)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound BrC1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC(OC(F)(F)F)=C1 QNVXSPMPOWRWKJ-UHFFFAOYSA-N 0.000 claims 1
- QINVYXVZKNUJQY-UHFFFAOYSA-N 2-[[2-bromo-4-(dodecylcarbamoyl)phenyl]methyl-[[4-(trifluoromethoxy)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound BrC1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(OC(F)(F)F)C=C1 QINVYXVZKNUJQY-UHFFFAOYSA-N 0.000 claims 1
- UJGKGQZVIFAWHD-UHFFFAOYSA-N 2-[[2-bromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[(2-phenylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1C1=CC=CC=C1 UJGKGQZVIFAWHD-UHFFFAOYSA-N 0.000 claims 1
- DJPAOLMZZCLWDE-UHFFFAOYSA-N 2-[[2-bromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[[2-(trifluoromethoxy)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1OC(F)(F)F DJPAOLMZZCLWDE-UHFFFAOYSA-N 0.000 claims 1
- JOOQARYLDZMRMR-UHFFFAOYSA-N 2-[[2-bromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[[3-(4-fluorophenyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC(C=2C=CC(F)=CC=2)=C1 JOOQARYLDZMRMR-UHFFFAOYSA-N 0.000 claims 1
- HNLSBXNTEAGZBO-UHFFFAOYSA-N 2-[[2-bromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[[3-(trifluoromethoxy)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC(OC(F)(F)F)=C1 HNLSBXNTEAGZBO-UHFFFAOYSA-N 0.000 claims 1
- BKDGHDKKBHONCD-UHFFFAOYSA-N 2-[[2-bromo-4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[[4-(trifluoromethoxy)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1Br)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(OC(F)(F)F)C=C1 BKDGHDKKBHONCD-UHFFFAOYSA-N 0.000 claims 1
- BWMBCMGKMDVNBU-UHFFFAOYSA-N 2-[[2-bromo-4-[2-(4-phenoxyphenyl)ethylcarbamoyl]phenyl]methyl-[(4-phenoxyphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C=1C=C(C(=O)NCCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC(C=C1)=CC=C1OC1=CC=CC=C1 BWMBCMGKMDVNBU-UHFFFAOYSA-N 0.000 claims 1
- MXXVDJGUOFWNJV-UHFFFAOYSA-N 2-[[2-bromo-4-[2-(4-phenoxyphenyl)ethylcarbamoyl]phenyl]methyl-[[3-(4-fluorophenyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=C(C(=O)NCCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC(C=1)=CC=CC=1C1=CC=C(F)C=C1 MXXVDJGUOFWNJV-UHFFFAOYSA-N 0.000 claims 1
- KQACVEFZUXZERH-UHFFFAOYSA-N 2-[[2-bromo-4-[2-(4-phenylphenyl)ethylcarbamoyl]phenyl]methyl-[(4-phenoxyphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C=1C=C(C(=O)NCCC=2C=CC(=CC=2)C=2C=CC=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC(C=C1)=CC=C1OC1=CC=CC=C1 KQACVEFZUXZERH-UHFFFAOYSA-N 0.000 claims 1
- HUKNFYCNNOFCFE-UHFFFAOYSA-N 2-[[2-bromo-4-[2-(4-phenylphenyl)ethylcarbamoyl]phenyl]methyl-[[3-(4-fluorophenyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=C(C(=O)NCCC=2C=CC(=CC=2)C=2C=CC=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC(C=1)=CC=CC=1C1=CC=C(F)C=C1 HUKNFYCNNOFCFE-UHFFFAOYSA-N 0.000 claims 1
- ZZNPMWHYVREKJI-UHFFFAOYSA-N 2-[[2-bromo-4-[2-(4-phenylphenyl)ethylcarbamoyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=C(C(=O)NCCC=2C=CC(=CC=2)C=2C=CC=CC=2)C=C(Br)C=1CN(C(=O)C(=O)O)CC1=CC=C(C(F)(F)F)C=C1 ZZNPMWHYVREKJI-UHFFFAOYSA-N 0.000 claims 1
- WYQXATNHFKEECI-UHFFFAOYSA-N 2-[[3-[2-(4-hexylphenyl)ethynyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCC)=CC=C1C#CC1=CC=CC(CN(CC=2C=CC(=CC=2)C(F)(F)F)C(=O)C(O)=O)=C1 WYQXATNHFKEECI-UHFFFAOYSA-N 0.000 claims 1
- DVEMXNHOAXXIAS-UHFFFAOYSA-N 2-[[4-(11-hydroxyundec-1-ynyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCCCO)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 DVEMXNHOAXXIAS-UHFFFAOYSA-N 0.000 claims 1
- QHOLALODSGEVIM-UHFFFAOYSA-N 2-[[4-(11-hydroxyundecyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCCCCCCCO)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 QHOLALODSGEVIM-UHFFFAOYSA-N 0.000 claims 1
- WUMQKLFRDNGXOK-UHFFFAOYSA-N 2-[[4-(11-methoxy-11-oxoundec-1-ynyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCCC(=O)OC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 WUMQKLFRDNGXOK-UHFFFAOYSA-N 0.000 claims 1
- BRVGHMFYSBKRKH-UHFFFAOYSA-N 2-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl-(5,6,7,8-tetrahydronaphthalen-1-yl)amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(C(=O)C(O)=O)C=3C=4CCCCC=4C=CC=3)=CC=2)=N1 BRVGHMFYSBKRKH-UHFFFAOYSA-N 0.000 claims 1
- CBFPSJVSMPHHEO-UHFFFAOYSA-N 2-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl-[(3-phenylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C=C(C=CC=3)C=3C=CC=CC=3)C(=O)C(O)=O)=CC=2)=N1 CBFPSJVSMPHHEO-UHFFFAOYSA-N 0.000 claims 1
- URONZOAOIJTGNM-UHFFFAOYSA-N 2-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl-[[2-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C(=CC=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=N1 URONZOAOIJTGNM-UHFFFAOYSA-N 0.000 claims 1
- NTODQVBAWKYNCB-UHFFFAOYSA-N 2-[[4-(3-octyl-1,2,4-oxadiazol-5-yl)phenyl]methyl-[[3-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C=C(C=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=N1 NTODQVBAWKYNCB-UHFFFAOYSA-N 0.000 claims 1
- MHAKAOQJVSTHFQ-UHFFFAOYSA-N 2-[[4-(4-ethyl-3-hydroxyoct-1-ynyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CC(O)C(CC)CCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 MHAKAOQJVSTHFQ-UHFFFAOYSA-N 0.000 claims 1
- KLWCGMGMTZTCTP-UHFFFAOYSA-N 2-[[4-(5-cyclohexylpent-1-ynyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)C(=O)O)CC(C=C1)=CC=C1C#CCCCC1CCCCC1 KLWCGMGMTZTCTP-UHFFFAOYSA-N 0.000 claims 1
- RPBKJEXFMPGWFS-UHFFFAOYSA-N 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[(1-hexanoylpiperidin-4-yl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1CCN(C(=O)CCCCC)CC1 RPBKJEXFMPGWFS-UHFFFAOYSA-N 0.000 claims 1
- NKDPAGKMBWMOAI-DEOSSOPVSA-N 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[(1s)-1-phenylethyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)[C@@H](C)C1=CC=CC=C1 NKDPAGKMBWMOAI-DEOSSOPVSA-N 0.000 claims 1
- XCEUXYLZJPDMOV-UHFFFAOYSA-N 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[2-(3-fluorophenyl)ethyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC(F)=C1 XCEUXYLZJPDMOV-UHFFFAOYSA-N 0.000 claims 1
- DLNFSDDVWQFEBN-UHFFFAOYSA-N 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[2-(3-methoxyphenyl)ethyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CCC1=CC=CC(OC)=C1 DLNFSDDVWQFEBN-UHFFFAOYSA-N 0.000 claims 1
- RNGXAZZJSAMBFT-LVZFUZTISA-N 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[[1-[(e)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl]piperidin-4-yl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1CCN(C(=O)\C=C\C=2C=C(C=CC=2)C(F)(F)F)CC1 RNGXAZZJSAMBFT-LVZFUZTISA-N 0.000 claims 1
- NHLMJKBBFKZGMH-UHFFFAOYSA-N 2-[[4-[(2-butyl-1-benzofuran-3-yl)methylcarbamoyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCC=1OC2=CC=CC=C2C=1CNC(=O)C(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 NHLMJKBBFKZGMH-UHFFFAOYSA-N 0.000 claims 1
- NUUPMMPUBKQEBT-UHFFFAOYSA-N 2-[[4-[(4-octylphenyl)carbamoyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1NC(=O)C(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 NUUPMMPUBKQEBT-UHFFFAOYSA-N 0.000 claims 1
- HLZWHARKIJBIPZ-UHFFFAOYSA-N 2-[[4-[2-(4-butylphenyl)ethyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCC)=CC=C1CCC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 HLZWHARKIJBIPZ-UHFFFAOYSA-N 0.000 claims 1
- HGABFWZGSXZNLW-UHFFFAOYSA-N 2-[[4-[2-(4-butylphenyl)ethynyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCC)=CC=C1C#CC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 HGABFWZGSXZNLW-UHFFFAOYSA-N 0.000 claims 1
- HEMSQIYUELJBSF-UHFFFAOYSA-N 2-[[4-[2-(4-heptoxyphenyl)ethyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(OCCCCCCC)=CC=C1CCC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 HEMSQIYUELJBSF-UHFFFAOYSA-N 0.000 claims 1
- SSGRHDMIGUJTHT-UHFFFAOYSA-N 2-[[4-[2-(4-heptoxyphenyl)ethynyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(OCCCCCCC)=CC=C1C#CC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 SSGRHDMIGUJTHT-UHFFFAOYSA-N 0.000 claims 1
- VFFWWXFOHRLZSL-UHFFFAOYSA-N 2-[[4-[2-(4-octylphenyl)ethyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1CCC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 VFFWWXFOHRLZSL-UHFFFAOYSA-N 0.000 claims 1
- QGLGCJBOIXMCOW-UHFFFAOYSA-N 2-[[4-[2-(4-octylphenyl)ethynyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1C#CC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 QGLGCJBOIXMCOW-UHFFFAOYSA-N 0.000 claims 1
- QSZIOYRKGCRTCD-UHFFFAOYSA-N 2-[[4-[3-(dodecylcarbamoyl)phenyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC(C=2C=CC(CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=C1 QSZIOYRKGCRTCD-UHFFFAOYSA-N 0.000 claims 1
- LEOOGXLRDCNVKU-UHFFFAOYSA-N 2-[[4-[3-(octylcarbamoyl)phenyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCNC(=O)C1=CC=CC(C=2C=CC(CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(O)=O)=CC=2)=C1 LEOOGXLRDCNVKU-UHFFFAOYSA-N 0.000 claims 1
- SYYSPOWBNFNTDK-UHFFFAOYSA-N 2-[[4-[3-[2-(4-phenoxyphenyl)ethylcarbamoyl]phenyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]acetic acid Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)CCNC(=O)C=1C=C(C=CC=1)C1=CC=C(C=C1)CN(CC1=CC=C(C=C1)C(F)(F)F)CC(=O)O SYYSPOWBNFNTDK-UHFFFAOYSA-N 0.000 claims 1
- FZOBPFVTELLQKM-UHFFFAOYSA-N 2-[[4-[4-(dodecylcarbamoyl)phenyl]phenyl]methyl-[[3-(4-fluorophenyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1C(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC(C=2C=CC(F)=CC=2)=C1 FZOBPFVTELLQKM-UHFFFAOYSA-N 0.000 claims 1
- MMLRKABZYSLRRY-UHFFFAOYSA-N 2-[[4-[4-(dodecylcarbamoyl)phenyl]phenyl]methyl-[[3-(trifluoromethoxy)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1C(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC(OC(F)(F)F)=C1 MMLRKABZYSLRRY-UHFFFAOYSA-N 0.000 claims 1
- PQXDFVISMWQISR-UHFFFAOYSA-N 2-[[4-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]phenyl]methyl-[[3-(trifluoromethyl)phenyl]methyl]amino]acetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2C=CC(CN(CC(O)=O)CC=3C=C(C=CC=3)C(F)(F)F)=CC=2)C=C1 PQXDFVISMWQISR-UHFFFAOYSA-N 0.000 claims 1
- OATDSSGGVIZGQV-UHFFFAOYSA-N 2-[[4-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]acetic acid Chemical compound C(CCCC)C1=CC=C(CNC(=O)C2=CC=C(C=C2)C2=CC=C(C=C2)CN(CC2=CC=C(C=C2)C(F)(F)F)CC(=O)O)C=C1 OATDSSGGVIZGQV-UHFFFAOYSA-N 0.000 claims 1
- IYCDQKGHMSOIRF-UHFFFAOYSA-N 2-[[4-[4-[2-(4-phenoxyphenyl)ethylcarbamoyl]phenyl]phenyl]methyl-[[2-(trifluoromethoxy)phenyl]methyl]amino]acetic acid Chemical compound C=1C=CC=C(OC(F)(F)F)C=1CN(CC(=O)O)CC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NCCC(C=C1)=CC=C1OC1=CC=CC=C1 IYCDQKGHMSOIRF-UHFFFAOYSA-N 0.000 claims 1
- UKLPFPQBWYCWBT-UHFFFAOYSA-N 2-[[5-(3,3-diphenylpropylsulfamoyl)thiophen-2-yl]methyl-[[3-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C=1C=CC(C(F)(F)F)=CC=1CN(C(=O)C(=O)O)CC(S1)=CC=C1S(=O)(=O)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 UKLPFPQBWYCWBT-UHFFFAOYSA-N 0.000 claims 1
- YKOLOJYNMYGMLZ-UHFFFAOYSA-N 2-[[cyclopentyl-[4-(trifluoromethyl)phenyl]methyl]-[[4-(tridecanoylamino)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(NC(=O)CCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)C(C=1C=CC(=CC=1)C(F)(F)F)C1CCCC1 YKOLOJYNMYGMLZ-UHFFFAOYSA-N 0.000 claims 1
- WCXSXCMXAUTJFL-UHFFFAOYSA-N 2-[benzyl-[[4-(tridecanoylamino)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(NC(=O)CCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1 WCXSXCMXAUTJFL-UHFFFAOYSA-N 0.000 claims 1
- FFTWTWFUQGERKQ-UHFFFAOYSA-N 2-[benzyl-[[4-[3-[(4-pentylphenyl)methylcarbamoyl]phenyl]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=CC(C=2C=CC(CN(CC=3C=CC=CC=3)C(=O)C(O)=O)=CC=2)=C1 FFTWTWFUQGERKQ-UHFFFAOYSA-N 0.000 claims 1
- ZMTSKQJIPAEOQZ-UHFFFAOYSA-N 2-[bis[(4-oct-1-ynylphenyl)methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C#CCCCCCC)C=C1 ZMTSKQJIPAEOQZ-UHFFFAOYSA-N 0.000 claims 1
- FOLKJQWHHFNXIK-UHFFFAOYSA-N 2-[n-[(4-dec-1-ynylphenyl)methyl]-4-(trifluoromethyl)anilino]-2-oxoacetic acid Chemical compound C1=CC(C#CCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)C1=CC=C(C(F)(F)F)C=C1 FOLKJQWHHFNXIK-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- GTESLIHEKNMAKX-UHFFFAOYSA-N 2-oxo-2-[(3-phenylphenyl)methyl-[[3-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]acetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=C(CN(CC=3C=C(C=CC=3)C=3C=CC=CC=3)C(=O)C(O)=O)C=CC=2)=N1 GTESLIHEKNMAKX-UHFFFAOYSA-N 0.000 claims 1
- XBIDOZVNXQYBSC-UHFFFAOYSA-N 2-oxo-2-[2-(4-phenylphenyl)ethyl-[[3-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]acetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=C(CN(CCC=3C=CC(=CC=3)C=3C=CC=CC=3)C(=O)C(O)=O)C=CC=2)=N1 XBIDOZVNXQYBSC-UHFFFAOYSA-N 0.000 claims 1
- IQBRMURBBATTDF-UHFFFAOYSA-N 2-oxo-2-[2-(4-phenylphenyl)ethyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]acetic acid Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CCC=3C=CC(=CC=3)C=3C=CC=CC=3)C(=O)C(O)=O)=CC=2)=N1 IQBRMURBBATTDF-UHFFFAOYSA-N 0.000 claims 1
- LDPXBXLXAZQEJJ-UHFFFAOYSA-N 2-oxo-2-[[4-[(4-phenylmethoxybenzoyl)amino]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]acetic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)C(=O)O)CC(C=C1)=CC=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 LDPXBXLXAZQEJJ-UHFFFAOYSA-N 0.000 claims 1
- MPFDWPOBNCZWBI-UHFFFAOYSA-N 2-oxo-2-[[4-[2-(4-phenylmethoxyphenyl)ethynyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]acetic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)C(=O)O)CC(C=C1)=CC=C1C#CC(C=C1)=CC=C1OCC1=CC=CC=C1 MPFDWPOBNCZWBI-UHFFFAOYSA-N 0.000 claims 1
- RRYXPTCOZVVPOW-UHFFFAOYSA-N 2-oxo-2-[[5-[2-(4-phenylphenyl)ethylsulfamoyl]thiophen-2-yl]methyl-[[3-(trifluoromethyl)phenyl]methyl]amino]acetic acid Chemical compound C=1C=CC(C(F)(F)F)=CC=1CN(C(=O)C(=O)O)CC(S1)=CC=C1S(=O)(=O)NCCC(C=C1)=CC=C1C1=CC=CC=C1 RRYXPTCOZVVPOW-UHFFFAOYSA-N 0.000 claims 1
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- UJACWTJPCDVHPR-UHFFFAOYSA-N 4-[[[5-(dodecylsulfamoyl)thiophen-2-yl]methyl-oxaloamino]methyl]benzoic acid Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(O)=O)C=C1 UJACWTJPCDVHPR-UHFFFAOYSA-N 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- PXLSNEKMNNKRFE-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC1=CC=C(CN(CC2=CC=C(C=C2)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O)C=C1.C(C1=CC=CC=C1)OC=1C=C(N(CC2=CC=C(C=C2)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O)C=CC1 Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=C(CN(CC2=CC=C(C=C2)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O)C=C1.C(C1=CC=CC=C1)OC=1C=C(N(CC2=CC=C(C=C2)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O)C=CC1 PXLSNEKMNNKRFE-UHFFFAOYSA-N 0.000 claims 1
- RNLSXFHVSPHFCT-UHFFFAOYSA-N C(C1=CC=CC=C1)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCCC)C(C(=O)O)=O.C(C1=CC=CC=C1)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCCCCC)C(C(=O)O)=O Chemical compound C(C1=CC=CC=C1)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCCC)C(C(=O)O)=O.C(C1=CC=CC=C1)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCCCCC)C(C(=O)O)=O RNLSXFHVSPHFCT-UHFFFAOYSA-N 0.000 claims 1
- UXJIVVPVAOEYMQ-UHFFFAOYSA-N C(CCCCCCCCCCC)NC(=O)C1=CC=C(CN(C2=CC=CC=C2)C(C(=O)O)=O)C=C1.BrC1=CC=C(N(CC2=CC=C(C=C2)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O)C=C1 Chemical compound C(CCCCCCCCCCC)NC(=O)C1=CC=C(CN(C2=CC=CC=C2)C(C(=O)O)=O)C=C1.BrC1=CC=C(N(CC2=CC=C(C=C2)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O)C=C1 UXJIVVPVAOEYMQ-UHFFFAOYSA-N 0.000 claims 1
- WUFPQBZVOVNPDA-UHFFFAOYSA-N C(CCCCCCCCCCC)NC(=O)C1=CC=C(CN(CC2=CC=C(C=C2)C=2N=NSC2)C(C(=O)O)=O)C=C1.C(=O)(O)C(=O)N(C(CC(=O)O)C1=CC=CC=C1)CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCC Chemical compound C(CCCCCCCCCCC)NC(=O)C1=CC=C(CN(CC2=CC=C(C=C2)C=2N=NSC2)C(C(=O)O)=O)C=C1.C(=O)(O)C(=O)N(C(CC(=O)O)C1=CC=CC=C1)CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCC WUFPQBZVOVNPDA-UHFFFAOYSA-N 0.000 claims 1
- ULBVTRQOGZRISK-UHFFFAOYSA-N C1(CCC2=CC=CC=C12)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O.O1COC2=C1C=CC(=C2)CN(CC2=CC=C(C=C2)C(=O)NCCC2=CC=C(C=C2)C2=CC=CC=C2)C(C(=O)O)=O Chemical compound C1(CCC2=CC=CC=C12)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O.O1COC2=C1C=CC(=C2)CN(CC2=CC=C(C=C2)C(=O)NCCC2=CC=C(C=C2)C2=CC=CC=C2)C(C(=O)O)=O ULBVTRQOGZRISK-UHFFFAOYSA-N 0.000 claims 1
- ZDKKNSSGHRWKRS-UHFFFAOYSA-N C1(CCCC1)N(CC=1SC(=CC1)S(=O)(=O)NCCCCCCCCCCCC)C(C(=O)O)=O.C(=O)(O)C(=O)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCC)CC=1C=C(C(=O)O)C=CC1 Chemical compound C1(CCCC1)N(CC=1SC(=CC1)S(=O)(=O)NCCCCCCCCCCCC)C(C(=O)O)=O.C(=O)(O)C(=O)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCC)CC=1C=C(C(=O)O)C=CC1 ZDKKNSSGHRWKRS-UHFFFAOYSA-N 0.000 claims 1
- HNIBMQRFHHORFF-UHFFFAOYSA-N C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(CN(CC2=CC=C(C=C2)C(F)(F)F)C(C(=O)O)=O)C=C3.C3=CC=C(C=2OC1=C(C23)C=CC=C1)C1=CC=C(CN(CC2=CC=C(C=C2)C(F)(F)F)C(C(=O)O)=O)C=C1 Chemical compound C1=CC=C(C=2OC3=C(C21)C=CC=C3)C3=CC=C(CN(CC2=CC=C(C=C2)C(F)(F)F)C(C(=O)O)=O)C=C3.C3=CC=C(C=2OC1=C(C23)C=CC=C1)C1=CC=C(CN(CC2=CC=C(C=C2)C(F)(F)F)C(C(=O)O)=O)C=C1 HNIBMQRFHHORFF-UHFFFAOYSA-N 0.000 claims 1
- WYZWJULLKAXWBC-UHFFFAOYSA-N ClC=1C(=C(C=CC1)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O)C.C(CCCCCCCCCCC)NC(=O)C1=CC=C(CN(CC2=CC(=C(C=C2)C(F)(F)F)F)C(C(=O)O)=O)C=C1 Chemical compound ClC=1C(=C(C=CC1)N(CC1=CC=C(C=C1)C(=O)NCCCCCCCCCCCC)C(C(=O)O)=O)C.C(CCCCCCCCCCC)NC(=O)C1=CC=C(CN(CC2=CC(=C(C=C2)C(F)(F)F)F)C(C(=O)O)=O)C=C1 WYZWJULLKAXWBC-UHFFFAOYSA-N 0.000 claims 1
- 125000002059 L-arginyl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 claims 1
- 125000001176 L-lysyl group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 229960005190 phenylalanine Drugs 0.000 claims 1
- UAPVLCBXIOCNSX-UHFFFAOYSA-M sodium;2-[(4-dec-1-ynylphenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound [Na+].C1=CC(C#CCCCCCCCC)=CC=C1CN(C(=O)C([O-])=O)CC1=CC=C(C(F)(F)F)C=C1 UAPVLCBXIOCNSX-UHFFFAOYSA-M 0.000 claims 1
- 230000002265 prevention Effects 0.000 abstract description 4
- 241000124008 Mammalia Species 0.000 abstract description 3
- 235000019789 appetite Nutrition 0.000 abstract description 2
- 230000036528 appetite Effects 0.000 abstract description 2
- 230000001404 mediated effect Effects 0.000 abstract 1
- 229920001469 poly(aryloxy)thionylphosphazene Polymers 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 376
- 238000000132 electrospray ionisation Methods 0.000 description 309
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 276
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 219
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
- 239000011347 resin Substances 0.000 description 122
- 229920005989 resin Polymers 0.000 description 122
- 230000015572 biosynthetic process Effects 0.000 description 120
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 103
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 79
- 239000000243 solution Substances 0.000 description 78
- 150000001412 amines Chemical class 0.000 description 71
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 68
- 239000003921 oil Substances 0.000 description 66
- 235000019198 oils Nutrition 0.000 description 66
- 239000012230 colorless oil Substances 0.000 description 64
- 239000011541 reaction mixture Substances 0.000 description 64
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
- 238000005481 NMR spectroscopy Methods 0.000 description 58
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 52
- 239000007787 solid Substances 0.000 description 50
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 46
- 239000002904 solvent Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 41
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 235000011054 acetic acid Nutrition 0.000 description 34
- 239000007864 aqueous solution Substances 0.000 description 29
- 239000012043 crude product Substances 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 28
- VODSFAVGEJUBHO-UHFFFAOYSA-N 3-[(9h-fluoren-9-ylmethoxycarbonylamino)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CNC(=O)OCC2C3=CC=CC=C3C3=CC=CC=C32)=C1 VODSFAVGEJUBHO-UHFFFAOYSA-N 0.000 description 27
- 102100028516 Receptor-type tyrosine-protein phosphatase U Human genes 0.000 description 26
- 230000000875 corresponding effect Effects 0.000 description 26
- 102000004877 Insulin Human genes 0.000 description 25
- 108090001061 Insulin Proteins 0.000 description 25
- 239000012044 organic layer Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- ISKYVDSKLGPEGI-UHFFFAOYSA-N 3-[4-[(9h-fluoren-9-ylmethoxycarbonylamino)methyl]phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC(CNC(=O)OCC3C4=CC=CC=C4C4=CC=CC=C43)=CC=2)=C1 ISKYVDSKLGPEGI-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 24
- 239000000843 powder Substances 0.000 description 24
- 229910001868 water Inorganic materials 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 21
- 150000001934 cyclohexanes Chemical class 0.000 description 21
- JRHUROPSUJVMNH-UHFFFAOYSA-N 4-[(9h-fluoren-9-ylmethoxycarbonylamino)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CNC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 JRHUROPSUJVMNH-UHFFFAOYSA-N 0.000 description 20
- 229940125396 insulin Drugs 0.000 description 19
- 238000004587 chromatography analysis Methods 0.000 description 18
- 238000004007 reversed phase HPLC Methods 0.000 description 18
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 235000019502 Orange oil Nutrition 0.000 description 13
- 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 description 13
- 239000006260 foam Substances 0.000 description 13
- 239000010502 orange oil Substances 0.000 description 13
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 13
- 108020000494 protein-tyrosine phosphatase Proteins 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000003335 secondary amines Chemical class 0.000 description 11
- 102000003746 Insulin Receptor Human genes 0.000 description 10
- 108010001127 Insulin Receptor Proteins 0.000 description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 9
- HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 description 9
- RCOVTJVRTZGSBP-UHFFFAOYSA-N 4-(chloromethyl)benzoyl chloride Chemical compound ClCC1=CC=C(C(Cl)=O)C=C1 RCOVTJVRTZGSBP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 9
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- YKYLFYOEGHUVPA-UHFFFAOYSA-N (4-pentylphenyl)methanamine;hydrochloride Chemical compound Cl.CCCCCC1=CC=C(CN)C=C1 YKYLFYOEGHUVPA-UHFFFAOYSA-N 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 8
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 8
- 238000010511 deprotection reaction Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
- JNHPLGDXCJAUBX-UHFFFAOYSA-N 2-(4-phenoxyphenyl)ethanamine Chemical compound C1=CC(CCN)=CC=C1OC1=CC=CC=C1 JNHPLGDXCJAUBX-UHFFFAOYSA-N 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 7
- 230000007017 scission Effects 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 6
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 6
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 101001087394 Homo sapiens Tyrosine-protein phosphatase non-receptor type 1 Proteins 0.000 description 6
- 102000016267 Leptin Human genes 0.000 description 6
- 108010092277 Leptin Proteins 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000004026 insulin derivative Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical group O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 6
- 229940039781 leptin Drugs 0.000 description 6
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 6
- 235000018102 proteins Nutrition 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- WMSUFWLPZLCIHP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 9h-fluoren-9-ylmethyl carbonate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)ON1C(=O)CCC1=O WMSUFWLPZLCIHP-UHFFFAOYSA-N 0.000 description 5
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 5
- RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 5
- WHPLBPSDTIZFSX-UHFFFAOYSA-N 2-(4-phenylphenyl)ethanamine Chemical compound C1=CC(CCN)=CC=C1C1=CC=CC=C1 WHPLBPSDTIZFSX-UHFFFAOYSA-N 0.000 description 5
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 5
- CANVYXIWNUMSCX-UHFFFAOYSA-N 5-(aminomethyl)-n-dodecylthiophene-2-sulfonamide Chemical compound CCCCCCCCCCCCNS(=O)(=O)C1=CC=C(CN)S1 CANVYXIWNUMSCX-UHFFFAOYSA-N 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- 101150041968 CDC13 gene Proteins 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 5
- 229950010170 epalrestat Drugs 0.000 description 5
- OPDJOMDAMOLNRS-UHFFFAOYSA-N ethyl 2-[(4-aminophenyl)methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)C(=O)OCC)CC1=CC=C(N)C=C1 OPDJOMDAMOLNRS-UHFFFAOYSA-N 0.000 description 5
- OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 230000011664 signaling Effects 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- LXANPKRCLVQAOG-NSHDSACASA-N sorbinil Chemical compound C12=CC(F)=CC=C2OCC[C@@]21NC(=O)NC2=O LXANPKRCLVQAOG-NSHDSACASA-N 0.000 description 5
- OMTBALPNZSJEBS-UHFFFAOYSA-N tert-butyl 4-[[[4-(dodecylcarbamoyl)phenyl]methyl-(2-ethoxy-2-oxoacetyl)amino]methyl]piperidine-1-carboxylate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1CCN(C(=O)OC(C)(C)C)CC1 OMTBALPNZSJEBS-UHFFFAOYSA-N 0.000 description 5
- GANNALTZZWCKFX-UHFFFAOYSA-N (2-bromo-4-carbonochloridoylphenyl)methyl-(9H-fluoren-9-ylmethoxycarbonyl)carbamic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)N(C(=O)O)CC1=CC=C(C(Cl)=O)C=C1Br GANNALTZZWCKFX-UHFFFAOYSA-N 0.000 description 4
- ICIJWOWQUHHETJ-UHFFFAOYSA-N (3,5-dichlorophenyl)methanamine Chemical compound NCC1=CC(Cl)=CC(Cl)=C1 ICIJWOWQUHHETJ-UHFFFAOYSA-N 0.000 description 4
- QUIIKTQSGAWIAC-UHFFFAOYSA-N 2-(2,4,6-trimethylphenyl)ethanamine Chemical compound CC1=CC(C)=C(CCN)C(C)=C1 QUIIKTQSGAWIAC-UHFFFAOYSA-N 0.000 description 4
- LKBFFDOJUKLQNY-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-4-oxo-1-phthalazinyl]acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=CC=C(Br)C=C1F LKBFFDOJUKLQNY-UHFFFAOYSA-N 0.000 description 4
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 4
- KISZTEOELCMZPY-UHFFFAOYSA-N 3,3-diphenylpropylamine Chemical compound C=1C=CC=CC=1C(CCN)C1=CC=CC=C1 KISZTEOELCMZPY-UHFFFAOYSA-N 0.000 description 4
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 4
- HFLFFRTWPLSPSN-UHFFFAOYSA-N 4-(aminomethyl)-3-bromobenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1Br HFLFFRTWPLSPSN-UHFFFAOYSA-N 0.000 description 4
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 4
- NIEBHDXUIJSHSL-UHFFFAOYSA-N 4-iodobenzaldehyde Chemical compound IC1=CC=C(C=O)C=C1 NIEBHDXUIJSHSL-UHFFFAOYSA-N 0.000 description 4
- LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 4
- QWLHJVDRPZNVBS-UHFFFAOYSA-N 4-phenoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OC1=CC=CC=C1 QWLHJVDRPZNVBS-UHFFFAOYSA-N 0.000 description 4
- MRPAGRCGPAXOGS-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carbaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=N1 MRPAGRCGPAXOGS-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012317 TBTU Substances 0.000 description 4
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 4
- 230000002152 alkylating effect Effects 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- ICUQZENIVHWUNV-UHFFFAOYSA-N benzyl 4-[(benzylamino)methyl]benzoate Chemical compound C=1C=C(CNCC=2C=CC=CC=2)C=CC=1C(=O)OCC1=CC=CC=C1 ICUQZENIVHWUNV-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- ZNDXMRCCHWURAG-UHFFFAOYSA-N ethyl 2-[benzyl-[[4-(tridecylcarbamoyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=CC=C1 ZNDXMRCCHWURAG-UHFFFAOYSA-N 0.000 description 4
- OVTXSTYAHWQYJI-UHFFFAOYSA-N ethyl 2-[cyclopentyl-[[5-(dodecylsulfamoyl)thiophen-2-yl]methyl]amino]-2-oxoacetate Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)C1CCCC1 OVTXSTYAHWQYJI-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 4
- 201000008980 hyperinsulinism Diseases 0.000 description 4
- 230000004060 metabolic process Effects 0.000 description 4
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 4
- 230000026731 phosphorylation Effects 0.000 description 4
- 238000006366 phosphorylation reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 4
- 229960003069 tolrestat Drugs 0.000 description 4
- 235000002374 tyrosine Nutrition 0.000 description 4
- SEAQTHCVAGBRFY-INWYIAFRSA-N (2r,4s)-6-fluoro-2-methylspiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C([C@H](OC1=CC=C(F)C=C11)C)[C@@]21NC(=O)NC2=O SEAQTHCVAGBRFY-INWYIAFRSA-N 0.000 description 3
- BSVHTRRLCAVQCZ-JDEXMCKMSA-N (2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-1-[(2s)-2-[[(2s)-1-[(2s)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-carboxypropanoyl]pyrrolidine-2-carbonyl]amino]propanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrro Chemical compound C([C@H](N)C(=O)N[C@@H](CC(O)=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CC=C(O)C=C1 BSVHTRRLCAVQCZ-JDEXMCKMSA-N 0.000 description 3
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 3
- CCAZAGUSBMVSAR-UHFFFAOYSA-N (4-phenoxyphenyl)methanamine Chemical compound C1=CC(CN)=CC=C1OC1=CC=CC=C1 CCAZAGUSBMVSAR-UHFFFAOYSA-N 0.000 description 3
- HGQSKTQYEWJJRZ-SNAWJCMRSA-N (e)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl chloride Chemical compound FC(F)(F)C1=CC=CC(\C=C\C(Cl)=O)=C1 HGQSKTQYEWJJRZ-SNAWJCMRSA-N 0.000 description 3
- ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 3
- ZJSUDHQFSBHLDV-UHFFFAOYSA-N 1-[(3-bromo-1-benzofuran-2-yl)sulfonyl]imidazolidine-2,4-dione Chemical compound O1C2=CC=CC=C2C(Br)=C1S(=O)(=O)N1CC(=O)NC1=O ZJSUDHQFSBHLDV-UHFFFAOYSA-N 0.000 description 3
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 3
- QCCHBHSAIQIQGO-UHFFFAOYSA-N 2,7-difluorospiro[fluorene-9,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2C2=CC=C(F)C=C2C21NC(=O)NC2=O QCCHBHSAIQIQGO-UHFFFAOYSA-N 0.000 description 3
- CLDJCRWXLDLJLO-UHFFFAOYSA-N 2-[2,8-di(propan-2-yl)-3-sulfanylidene-1,4-benzoxazin-4-yl]acetic acid Chemical compound C1=CC=C2N(CC(O)=O)C(=S)C(C(C)C)OC2=C1C(C)C CLDJCRWXLDLJLO-UHFFFAOYSA-N 0.000 description 3
- YREIRIKJAMPPHC-UHFFFAOYSA-N 2-[3-[(3-nitrophenyl)methyl]-2,4,5-trioxoimidazolidin-1-yl]acetic acid Chemical compound O=C1C(=O)N(CC(=O)O)C(=O)N1CC1=CC=CC([N+]([O-])=O)=C1 YREIRIKJAMPPHC-UHFFFAOYSA-N 0.000 description 3
- MBPMSWHKSOGXHS-UHFFFAOYSA-N 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[[3-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC(C(F)(F)F)=C1 MBPMSWHKSOGXHS-UHFFFAOYSA-N 0.000 description 3
- ZIJBZIPNUGLIDD-UHFFFAOYSA-N 2-[benzyl-[[3-(dodecylcarbamoyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC(CN(CC=2C=CC=CC=2)C(=O)C(O)=O)=C1 ZIJBZIPNUGLIDD-UHFFFAOYSA-N 0.000 description 3
- RMTYNPFEAIDCJK-UHFFFAOYSA-N 2-[benzyl-[[4-(dodecylcarbamoyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1 RMTYNPFEAIDCJK-UHFFFAOYSA-N 0.000 description 3
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 3
- VDZWHWVAMDQEBT-UHFFFAOYSA-N 2-morpholin-4-yl-1,3-thiazole-5-carbaldehyde Chemical compound S1C(C=O)=CN=C1N1CCOCC1 VDZWHWVAMDQEBT-UHFFFAOYSA-N 0.000 description 3
- RIIVBOIBIOLLPO-UHFFFAOYSA-N 2-phthalazin-1-ylacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=NN=CC2=C1 RIIVBOIBIOLLPO-UHFFFAOYSA-N 0.000 description 3
- BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-dihydro-4-oxo-3-((5-trifluoromethyl-2-benzothiazolyl)methyl)-1-phthalazine acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 description 3
- FXWLTHMYNSCDFI-UHFFFAOYSA-N 3,5-dibromo-4-[(9h-fluoren-9-ylmethoxycarbonylamino)methyl]benzoic acid Chemical compound BrC1=CC(C(=O)O)=CC(Br)=C1CNC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 FXWLTHMYNSCDFI-UHFFFAOYSA-N 0.000 description 3
- UHDNUPHSDMOGCR-UHFFFAOYSA-N 3-Formylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=O)=C1 UHDNUPHSDMOGCR-UHFFFAOYSA-N 0.000 description 3
- RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 3
- DTELTOREECFDBC-UHFFFAOYSA-N 3-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(I)=C1 DTELTOREECFDBC-UHFFFAOYSA-N 0.000 description 3
- CTUJRWNKQFXVNI-UHFFFAOYSA-N 4-(aminomethyl)-3,5-dibromobenzamide Chemical compound NCC1=C(Br)C=C(C(N)=O)C=C1Br CTUJRWNKQFXVNI-UHFFFAOYSA-N 0.000 description 3
- UNFDWXYUGDBUKL-UHFFFAOYSA-N 4-(aminomethyl)-3,5-dibromobenzoic acid Chemical compound NCC1=C(Br)C=C(C(O)=O)C=C1Br UNFDWXYUGDBUKL-UHFFFAOYSA-N 0.000 description 3
- VCPLNCTYZAIBPE-UHFFFAOYSA-N 4-(aminomethyl)-3-bromobenzamide Chemical compound NCC1=CC=C(C(N)=O)C=C1Br VCPLNCTYZAIBPE-UHFFFAOYSA-N 0.000 description 3
- WYPOMHXSGAVSOG-UHFFFAOYSA-N 4-(chloromethyl)-n-dodecylbenzamide Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=C(CCl)C=C1 WYPOMHXSGAVSOG-UHFFFAOYSA-N 0.000 description 3
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 3
- DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 3
- PSVPUHBSBYJSMQ-UHFFFAOYSA-N 4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1 PSVPUHBSBYJSMQ-UHFFFAOYSA-N 0.000 description 3
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 3
- VFEAMMGYJFFXKV-UHFFFAOYSA-N 5-formylthiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C=O)S1 VFEAMMGYJFFXKV-UHFFFAOYSA-N 0.000 description 3
- 101100248451 Arabidopsis thaliana RICE2 gene Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 240000001414 Eucalyptus viminalis Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 3
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 108010077495 Peptide oostatic hormone Proteins 0.000 description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- PRDBLLIPPDOICK-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=C(C(F)(F)F)C=C1 PRDBLLIPPDOICK-UHFFFAOYSA-N 0.000 description 3
- 239000003288 aldose reductase inhibitor Substances 0.000 description 3
- 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 3
- 230000003143 atherosclerotic effect Effects 0.000 description 3
- HFAXDENKQHZISQ-UHFFFAOYSA-N benzyl 4-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]benzoate Chemical compound C1=CC(C(F)(F)F)=CC=C1CNCC1=CC=C(C(=O)OCC=2C=CC=CC=2)C=C1 HFAXDENKQHZISQ-UHFFFAOYSA-N 0.000 description 3
- JCYUVFOJNQNFQF-UHFFFAOYSA-N benzyl 4-formylbenzoate Chemical compound C1=CC(C=O)=CC=C1C(=O)OCC1=CC=CC=C1 JCYUVFOJNQNFQF-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- CHNUOJQWGUIOLD-UHFFFAOYSA-N epalrestate Natural products C=1C=CC=CC=1C=C(C)C=C1SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-UHFFFAOYSA-N 0.000 description 3
- WQTOWXISVNIHGB-UHFFFAOYSA-N ethyl 2-[(4-aminophenyl)methyl-benzylamino]-2-oxoacetate Chemical compound C=1C=C(N)C=CC=1CN(C(=O)C(=O)OCC)CC1=CC=CC=C1 WQTOWXISVNIHGB-UHFFFAOYSA-N 0.000 description 3
- PMZOAFKOEVNMAI-UHFFFAOYSA-N ethyl 2-oxo-2-[[4-(trifluoromethyl)phenyl]methyl-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]amino]acetate Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)C(=O)OCC)=CC=2)=N1 PMZOAFKOEVNMAI-UHFFFAOYSA-N 0.000 description 3
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 229960002449 glycine Drugs 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 229950007327 imirestat Drugs 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- CHYJSLZNYDHTHE-UHFFFAOYSA-N methyl 3,5-dibromo-4-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC(Br)=C(CBr)C(Br)=C1 CHYJSLZNYDHTHE-UHFFFAOYSA-N 0.000 description 3
- CFJQBNFFHMBNKQ-UHFFFAOYSA-N methyl 3-bromo-4-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C(Br)=C1 CFJQBNFFHMBNKQ-UHFFFAOYSA-N 0.000 description 3
- MASRAGFWFYHMFI-UHFFFAOYSA-N methyl 3-bromo-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(Br)=C1 MASRAGFWFYHMFI-UHFFFAOYSA-N 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 3
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 3
- 229940081310 piperonal Drugs 0.000 description 3
- 229950010884 ponalrestat Drugs 0.000 description 3
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 3
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 238000006268 reductive amination reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CRPGRUONUFDYBG-UHFFFAOYSA-N risarestat Chemical compound C1=C(OCC)C(OCCCCC)=CC=C1C1C(=O)NC(=O)S1 CRPGRUONUFDYBG-UHFFFAOYSA-N 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 229950004311 sorbinil Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- HMBPKCRKOXMOSQ-UHFFFAOYSA-N tert-butyl 4-(4-methylphenyl)benzoate Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(=O)OC(C)(C)C)C=C1 HMBPKCRKOXMOSQ-UHFFFAOYSA-N 0.000 description 3
- KLKBCNDBOVRQIJ-UHFFFAOYSA-N tert-butyl 4-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CN)CC1 KLKBCNDBOVRQIJ-UHFFFAOYSA-N 0.000 description 3
- SLKAPMOHLJOIKQ-UHFFFAOYSA-N tert-butyl 4-[[(2-ethoxy-2-oxoacetyl)-[(4-phenylmethoxycarbonylphenyl)methyl]amino]methyl]piperidine-1-carboxylate Chemical compound C=1C=C(C(=O)OCC=2C=CC=CC=2)C=CC=1CN(C(=O)C(=O)OCC)CC1CCN(C(=O)OC(C)(C)C)CC1 SLKAPMOHLJOIKQ-UHFFFAOYSA-N 0.000 description 3
- IXXNEUFRDMMLNB-UHFFFAOYSA-N tert-butyl 4-[[4-(dodecylcarbamoyl)phenyl]methyl-(2-ethoxy-2-oxoacetyl)amino]piperidine-1-carboxylate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)C1CCN(C(=O)OC(C)(C)C)CC1 IXXNEUFRDMMLNB-UHFFFAOYSA-N 0.000 description 3
- URXUHALBOWYXJZ-UHFFFAOYSA-N tert-butyl n-[4-(aminomethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(CN)C=C1 URXUHALBOWYXJZ-UHFFFAOYSA-N 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 125000005309 thioalkoxy group Chemical group 0.000 description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
- SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 3
- 229950006343 zenarestat Drugs 0.000 description 3
- 229950005346 zopolrestat Drugs 0.000 description 3
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 2
- WAAPEIZFCHNLKK-UFBFGSQYSA-N (2s,4s)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide Chemical compound C([C@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-UFBFGSQYSA-N 0.000 description 2
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 2
- QIEDWVJRICQSAL-UHFFFAOYSA-N (4-pentylphenyl)methanamine Chemical compound CCCCCC1=CC=C(CN)C=C1 QIEDWVJRICQSAL-UHFFFAOYSA-N 0.000 description 2
- BMHZAHGTGIZZCT-LJQANCHMSA-N (4r)-2-[(4-bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4,3'-pyrrolidine]-1,2',3,5'-tetrone Chemical compound C1([C@]2(C(NC(=O)C2)=O)C2=O)=CC(F)=CC=C1C(=O)N2CC1=CC=C(Br)C=C1F BMHZAHGTGIZZCT-LJQANCHMSA-N 0.000 description 2
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 2
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 2
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 2
- YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 2
- NXMXETCTWNXSFG-UHFFFAOYSA-N 1-methoxypropan-2-amine Chemical compound COCC(C)N NXMXETCTWNXSFG-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 2
- GEJBGTIMCSAZDW-UHFFFAOYSA-N 2-(1,3-thiazolidin-3-yl)acetic acid Chemical compound OC(=O)CN1CCSC1 GEJBGTIMCSAZDW-UHFFFAOYSA-N 0.000 description 2
- OZUNHSMQAVTNLW-UHFFFAOYSA-N 2-(2-phenoxyphenyl)ethanamine Chemical compound NCCC1=CC=CC=C1OC1=CC=CC=C1 OZUNHSMQAVTNLW-UHFFFAOYSA-N 0.000 description 2
- NRHVNPYOTNGECT-UHFFFAOYSA-N 2-(3-chlorophenyl)ethanamine Chemical compound NCCC1=CC=CC(Cl)=C1 NRHVNPYOTNGECT-UHFFFAOYSA-N 0.000 description 2
- WJBMRZAHTUFBGE-UHFFFAOYSA-N 2-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC(CCN)=C1 WJBMRZAHTUFBGE-UHFFFAOYSA-N 0.000 description 2
- FRBDLDNQZCDPOB-UHFFFAOYSA-N 2-(thiophen-2-ylmethyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC=CS1 FRBDLDNQZCDPOB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- BEGJKQPWVJRBPU-UHFFFAOYSA-N 2-[3-methyl-5-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]phenyl]acetic acid Chemical compound CC1=CC(CC(O)=O)=CC(CC=2SC3=C(F)C=C(F)C(F)=C3N=2)=C1 BEGJKQPWVJRBPU-UHFFFAOYSA-N 0.000 description 2
- BUYWFAJWTSIACV-UHFFFAOYSA-N 2-[3-oxo-4-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]-1,4-benzothiazin-2-yl]acetic acid Chemical compound FC1=CC(F)=C2SC(CN3C4=CC=CC=C4SC(C3=O)CC(=O)O)=NC2=C1F BUYWFAJWTSIACV-UHFFFAOYSA-N 0.000 description 2
- XKUNZBICRPNZNL-UHFFFAOYSA-N 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 XKUNZBICRPNZNL-UHFFFAOYSA-N 0.000 description 2
- YVMKFWBOYMCFFJ-UHFFFAOYSA-N 2-[[5-(dodecylsulfamoyl)thiophen-2-yl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 YVMKFWBOYMCFFJ-UHFFFAOYSA-N 0.000 description 2
- RFDMSFMGPGPLKJ-UHFFFAOYSA-N 2-[benzyl-[[5-(dodecylsulfamoyl)thiophen-2-yl]methyl]amino]-2-oxoacetic acid Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1 RFDMSFMGPGPLKJ-UHFFFAOYSA-N 0.000 description 2
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 2
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 2
- HCTJDUDDYVEIAZ-UHFFFAOYSA-N 3-[(benzylamino)methyl]-n-dodecylbenzamide Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC(CNCC=2C=CC=CC=2)=C1 HCTJDUDDYVEIAZ-UHFFFAOYSA-N 0.000 description 2
- SNBRFTBVKYFJHX-UHFFFAOYSA-N 3-[4-(aminomethyl)phenyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(CN)=CC=C1C1=CC=CC(C(O)=O)=C1 SNBRFTBVKYFJHX-UHFFFAOYSA-N 0.000 description 2
- UJOYFRCOTPUKAK-UHFFFAOYSA-N 3-ammonio-3-phenylpropanoate Chemical compound [O-]C(=O)CC([NH3+])C1=CC=CC=C1 UJOYFRCOTPUKAK-UHFFFAOYSA-N 0.000 description 2
- RDVKYLZMXMNZTC-UHFFFAOYSA-N 3-bromo-4-[(9h-fluoren-9-ylmethoxycarbonylamino)methyl]benzoic acid Chemical compound BrC1=CC(C(=O)O)=CC=C1CNC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 RDVKYLZMXMNZTC-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 2
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 2
- ZBIAHIYQFFLIGR-UHFFFAOYSA-N 4-[4-(aminomethyl)phenyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(CN)=CC=C1C1=CC=C(C(O)=O)C=C1 ZBIAHIYQFFLIGR-UHFFFAOYSA-N 0.000 description 2
- JFQVFSHBCMGXJB-UHFFFAOYSA-N 4-[[(2-ethoxy-2-oxoacetyl)-(piperidin-4-ylmethyl)amino]methyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1CN(C(=O)C(=O)OCC)CC1CCNCC1 JFQVFSHBCMGXJB-UHFFFAOYSA-N 0.000 description 2
- UDDOYQYRCVDRQC-UHFFFAOYSA-N 4-[[(2-ethoxy-2-oxoacetyl)-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]benzoic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)C(=O)OCC)CC1=CC=C(C(O)=O)C=C1 UDDOYQYRCVDRQC-UHFFFAOYSA-N 0.000 description 2
- OQQVJUXELVBHQQ-UHFFFAOYSA-N 4-amino-n-dodecylbenzamide Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=C(N)C=C1 OQQVJUXELVBHQQ-UHFFFAOYSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- GOUHYARYYWKXHS-UHFFFAOYSA-M 4-formylbenzoate Chemical compound [O-]C(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-M 0.000 description 2
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 2
- AGNFWIZBEATIAK-UHFFFAOYSA-N 4-phenylbutylamine Chemical compound NCCCCC1=CC=CC=C1 AGNFWIZBEATIAK-UHFFFAOYSA-N 0.000 description 2
- LDBKJZNVHQGUON-UHFFFAOYSA-N 5-[(1,3-dioxoisoindol-2-yl)methyl]-n-dodecylthiophene-2-sulfonamide Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CN1C(=O)C2=CC=CC=C2C1=O LDBKJZNVHQGUON-UHFFFAOYSA-N 0.000 description 2
- KZRZSNJPWGKGQU-UHFFFAOYSA-N 5-[(1,3-dioxoisoindol-2-yl)methyl]thiophene-2-sulfonyl chloride Chemical compound S1C(S(=O)(=O)Cl)=CC=C1CN1C(=O)C2=CC=CC=C2C1=O KZRZSNJPWGKGQU-UHFFFAOYSA-N 0.000 description 2
- BUMXZWZSHQQCAP-UHFFFAOYSA-N 5-[(benzylamino)methyl]-n-dodecylthiophene-2-sulfonamide Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CNCC1=CC=CC=C1 BUMXZWZSHQQCAP-UHFFFAOYSA-N 0.000 description 2
- MUSSATMWVRCVJZ-UHFFFAOYSA-N 5-[(cyclopentylamino)methyl]-n-dodecylthiophene-2-sulfonamide Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CNC1CCCC1 MUSSATMWVRCVJZ-UHFFFAOYSA-N 0.000 description 2
- AYSITEYZYGZKOJ-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl 4-[[[4-(dodecylcarbamoyl)phenyl]methyl-(2-ethoxy-2-oxoacetyl)amino]methyl]piperidine-1-carboxylate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1CCN(C(=O)OCC2C3=CC=CC=C3C3=CC=CC=C32)CC1 AYSITEYZYGZKOJ-UHFFFAOYSA-N 0.000 description 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 102100039663 Receptor-type tyrosine-protein phosphatase F Human genes 0.000 description 2
- 101710138741 Receptor-type tyrosine-protein phosphatase F Proteins 0.000 description 2
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 2
- 102000001332 SRC Human genes 0.000 description 2
- 108060006706 SRC Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
- 102100033019 Tyrosine-protein phosphatase non-receptor type 11 Human genes 0.000 description 2
- 101710116241 Tyrosine-protein phosphatase non-receptor type 11 Proteins 0.000 description 2
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 2
- 229960002632 acarbose Drugs 0.000 description 2
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 238000011914 asymmetric synthesis Methods 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- QJAWGGHVEDUJMF-UHFFFAOYSA-N benzyl 4-[[(2-methylpropan-2-yl)oxycarbonyl-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]benzoate Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)OC(C)(C)C)CC(C=C1)=CC=C1C(=O)OCC1=CC=CC=C1 QJAWGGHVEDUJMF-UHFFFAOYSA-N 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 229960001761 chlorpropamide Drugs 0.000 description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- OKQSSSVVBOUMNZ-UHFFFAOYSA-N diminazene diaceturate Chemical compound CC(=O)NCC(O)=O.CC(=O)NCC(O)=O.C1=CC(C(=N)N)=CC=C1NN=NC1=CC=C(C(N)=N)C=C1 OKQSSSVVBOUMNZ-UHFFFAOYSA-N 0.000 description 2
- JCGDOKGJPQJKOP-UHFFFAOYSA-N ethyl 2-[[4-(2-hydroxydodecylamino)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(NCC(O)CCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=C(C(F)(F)F)C=C1 JCGDOKGJPQJKOP-UHFFFAOYSA-N 0.000 description 2
- XYGYADJOYMEFMH-UHFFFAOYSA-N ethyl 2-[[4-(dodecylcarbamoyl)phenyl]methyl-(piperidin-4-ylmethyl)amino]-2-oxoacetate;hydrochloride Chemical compound Cl.C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1CCNCC1 XYGYADJOYMEFMH-UHFFFAOYSA-N 0.000 description 2
- WEIRNNWIAULZRW-UHFFFAOYSA-N ethyl 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[[1-(4-methoxyphenyl)sulfonylpiperidin-4-yl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1CCN(S(=O)(=O)C=2C=CC(OC)=CC=2)CC1 WEIRNNWIAULZRW-UHFFFAOYSA-N 0.000 description 2
- SCHGSPBVUFQABV-UHFFFAOYSA-N ethyl 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=C(C(F)(F)F)C=C1 SCHGSPBVUFQABV-UHFFFAOYSA-N 0.000 description 2
- ZUEOXIMDIISMEI-UHFFFAOYSA-N ethyl 2-[[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)C(=O)OCC)CC1=CC=C(NC(=O)OC(C)(C)C)C=C1 ZUEOXIMDIISMEI-UHFFFAOYSA-N 0.000 description 2
- RRGLMLFUKRFGON-UHFFFAOYSA-N ethyl 2-[[4-[dodecyl(methyl)carbamoyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(C(=O)N(C)CCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=C(C(F)(F)F)C=C1 RRGLMLFUKRFGON-UHFFFAOYSA-N 0.000 description 2
- LYXZRZCKIZFWKN-UHFFFAOYSA-N ethyl 2-[benzyl-[[4-(tridecanoylamino)phenyl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(NC(=O)CCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=CC=C1 LYXZRZCKIZFWKN-UHFFFAOYSA-N 0.000 description 2
- BWTOCQCKVZVKIR-UHFFFAOYSA-N ethyl 2-[benzyl-[[5-(dodecylsulfamoyl)thiophen-2-yl]methyl]amino]-2-oxoacetate Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=CC=C1 BWTOCQCKVZVKIR-UHFFFAOYSA-N 0.000 description 2
- FNNXQLSKQSVNLL-UHFFFAOYSA-N ethyl 2-amino-2-phenylacetate;hydrochloride Chemical compound Cl.CCOC(=O)C(N)C1=CC=CC=C1 FNNXQLSKQSVNLL-UHFFFAOYSA-N 0.000 description 2
- XPROVVDUZLYCIE-UHFFFAOYSA-N ethyl 2-oxo-2-[[4-(tridecanoylamino)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]acetate Chemical compound C1=CC(NC(=O)CCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=C(C(F)(F)F)C=C1 XPROVVDUZLYCIE-UHFFFAOYSA-N 0.000 description 2
- SRCCTOUGTGTEJB-UHFFFAOYSA-N ethyl 2-oxo-2-[[4-(trifluoromethyl)phenyl]methyl-[[4-(undec-10-enoylamino)phenyl]methyl]amino]acetate Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)C(=O)OCC)CC1=CC=C(NC(=O)CCCCCCCCC=C)C=C1 SRCCTOUGTGTEJB-UHFFFAOYSA-N 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 2
- 229960004346 glimepiride Drugs 0.000 description 2
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 2
- 229960001381 glipizide Drugs 0.000 description 2
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 2
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007972 injectable composition Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 2
- 229960003105 metformin Drugs 0.000 description 2
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 229960001110 miglitol Drugs 0.000 description 2
- 229950002259 minalrestat Drugs 0.000 description 2
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 2
- KVACUYQANHDHQF-UHFFFAOYSA-N n'-hydroxydodecanimidamide Chemical compound CCCCCCCCCCCC(N)=NO KVACUYQANHDHQF-UHFFFAOYSA-N 0.000 description 2
- LNIJTMGXVKXZQY-UHFFFAOYSA-N n-[4-(aminomethyl)phenyl]benzamide Chemical compound C1=CC(CN)=CC=C1NC(=O)C1=CC=CC=C1 LNIJTMGXVKXZQY-UHFFFAOYSA-N 0.000 description 2
- PPDMFPAUYMHVCY-UHFFFAOYSA-N n-dodecyl-4-[[[3-(trifluoromethyl)phenyl]methylamino]methyl]benzamide Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CNCC1=CC=CC(C(F)(F)F)=C1 PPDMFPAUYMHVCY-UHFFFAOYSA-N 0.000 description 2
- UUGYWVGDIGNFTK-UHFFFAOYSA-N n-dodecyl-4-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]benzamide Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CNCC1=CC=C(C(F)(F)F)C=C1 UUGYWVGDIGNFTK-UHFFFAOYSA-N 0.000 description 2
- IYTAVFWBJIHCTM-UHFFFAOYSA-N n-dodecyl-4-formylbenzamide Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=C(C=O)C=C1 IYTAVFWBJIHCTM-UHFFFAOYSA-N 0.000 description 2
- LBMIQTNISHUWON-UHFFFAOYSA-N n-dodecyl-4-nitrobenzamide Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=C([N+]([O-])=O)C=C1 LBMIQTNISHUWON-UHFFFAOYSA-N 0.000 description 2
- NSZZCDXVJKWBSF-UHFFFAOYSA-N n-dodecyl-5-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]thiophene-2-sulfonamide Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CNCC1=CC=C(C(F)(F)F)C=C1 NSZZCDXVJKWBSF-UHFFFAOYSA-N 0.000 description 2
- OMEMQVZNTDHENJ-UHFFFAOYSA-N n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCNC OMEMQVZNTDHENJ-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- SOPDQKNXOCUBSR-UHFFFAOYSA-N quinoxaline-2-carbonyl chloride Chemical compound C1=CC=CC2=NC(C(=O)Cl)=CN=C21 SOPDQKNXOCUBSR-UHFFFAOYSA-N 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 238000011808 rodent model Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000010532 solid phase synthesis reaction Methods 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- JIOJNZNLKIBVJJ-UHFFFAOYSA-N tert-butyl 3-[4-(bromomethyl)phenyl]benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC(C=2C=CC(CBr)=CC=2)=C1 JIOJNZNLKIBVJJ-UHFFFAOYSA-N 0.000 description 2
- NPVLZVSAZXTBSR-UHFFFAOYSA-N tert-butyl 3-bromobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC(Br)=C1 NPVLZVSAZXTBSR-UHFFFAOYSA-N 0.000 description 2
- RXFRQCIRTWTCRE-UHFFFAOYSA-N tert-butyl 4-[(2-ethoxy-2-oxoacetyl)-[(4-phenylmethoxycarbonylphenyl)methyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N(C(=O)C(=O)OCC)CC(C=C1)=CC=C1C(=O)OCC1=CC=CC=C1 RXFRQCIRTWTCRE-UHFFFAOYSA-N 0.000 description 2
- NQYFCRNMUUQFGI-UHFFFAOYSA-N tert-butyl 4-[(4-phenylmethoxycarbonylphenyl)methylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NCC1=CC=C(C(=O)OCC=2C=CC=CC=2)C=C1 NQYFCRNMUUQFGI-UHFFFAOYSA-N 0.000 description 2
- KMEBJAHJKKYYAF-UHFFFAOYSA-N tert-butyl 4-[4-(bromomethyl)phenyl]benzoate Chemical compound C1=CC(C(=O)OC(C)(C)C)=CC=C1C1=CC=C(CBr)C=C1 KMEBJAHJKKYYAF-UHFFFAOYSA-N 0.000 description 2
- HFSXRCBIMXFVDR-UHFFFAOYSA-N tert-butyl n-[4-[(benzylamino)methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1CNCC1=CC=CC=C1 HFSXRCBIMXFVDR-UHFFFAOYSA-N 0.000 description 2
- BMUVKCZVKDGBDM-UHFFFAOYSA-N tert-butyl n-[4-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1CNCC1=CC=C(C(F)(F)F)C=C1 BMUVKCZVKDGBDM-UHFFFAOYSA-N 0.000 description 2
- DASVVQIZDOMPOO-UHFFFAOYSA-N tert-butyl n-[[4-(trifluoromethyl)phenyl]methyl]-n-[[4-(3-undecyl-1,2,4-oxadiazol-5-yl)phenyl]methyl]carbamate Chemical compound CCCCCCCCCCCC1=NOC(C=2C=CC(CN(CC=3C=CC(=CC=3)C(F)(F)F)C(=O)OC(C)(C)C)=CC=2)=N1 DASVVQIZDOMPOO-UHFFFAOYSA-N 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 2
- 229960002277 tolazamide Drugs 0.000 description 2
- 229960005371 tolbutamide Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- FJRPWCNFWGBGOF-UHFFFAOYSA-N tridecanoyl chloride Chemical compound CCCCCCCCCCCCC(Cl)=O FJRPWCNFWGBGOF-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000000825 ultraviolet detection Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- NMMOIQHIWAYSGF-UHFFFAOYSA-N (1-aminododecylideneamino) 4-[[(2-methylpropan-2-yl)oxycarbonyl-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]benzoate Chemical compound C1=CC(C(=O)ONC(=N)CCCCCCCCCCC)=CC=C1CN(C(=O)OC(C)(C)C)CC1=CC=C(C(F)(F)F)C=C1 NMMOIQHIWAYSGF-UHFFFAOYSA-N 0.000 description 1
- ZPEFMSTTZXJOTM-OULXEKPRSA-N (1R,2S)-tranylcypromine hydrochloride Chemical compound Cl.N[C@@H]1C[C@H]1C1=CC=CC=C1 ZPEFMSTTZXJOTM-OULXEKPRSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- WKHABRRJMGVELW-UHFFFAOYSA-N (3-phenylphenyl)methanamine Chemical compound NCC1=CC=CC(C=2C=CC=CC=2)=C1 WKHABRRJMGVELW-UHFFFAOYSA-N 0.000 description 1
- OAIGWGVWGSHPFS-UHFFFAOYSA-N (3-phenylphenyl)methanamine;hydrobromide Chemical compound Br.NCC1=CC=CC(C=2C=CC=CC=2)=C1 OAIGWGVWGSHPFS-UHFFFAOYSA-N 0.000 description 1
- DQVXWCCLFKMJTQ-UHFFFAOYSA-N (4-methylphenoxy)boronic acid Chemical compound CC1=CC=C(OB(O)O)C=C1 DQVXWCCLFKMJTQ-UHFFFAOYSA-N 0.000 description 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- 125000005964 1,2,4-oxadiazolidinyl group Chemical group 0.000 description 1
- 125000005965 1,3,4-oxadiazolidinyl group Chemical group 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- RTCUCQWIICFPOD-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(C(N)C)=CC=CC2=C1 RTCUCQWIICFPOD-UHFFFAOYSA-N 0.000 description 1
- VUEWYZJJYGPJDC-UHFFFAOYSA-N 1-oxaspiro[2.5]octane Chemical compound C1OC11CCCCC1 VUEWYZJJYGPJDC-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 1
- SNTGHASAODNGHV-UHFFFAOYSA-N 2-(1,2-dihydroquinazolin-2-yl)acetic acid Chemical compound C1=CC=C2C=NC(CC(=O)O)NC2=C1 SNTGHASAODNGHV-UHFFFAOYSA-N 0.000 description 1
- DLUNBMFXZPHTDJ-UHFFFAOYSA-N 2-(1,4-benzoxazin-4-yl)acetic acid Chemical compound C1=CC=C2N(CC(=O)O)C=COC2=C1 DLUNBMFXZPHTDJ-UHFFFAOYSA-N 0.000 description 1
- PVCBNTQFUNMPTC-UHFFFAOYSA-N 2-(2h-1,4-benzothiazin-2-yl)acetic acid Chemical compound C1=CC=C2N=CC(CC(=O)O)SC2=C1 PVCBNTQFUNMPTC-UHFFFAOYSA-N 0.000 description 1
- PQHQBRJAAZQXHL-GQCOAOBCSA-N 2-(4-iodanyl-2,5-dimethoxyphenyl)ethanamine Chemical compound COC1=CC(CCN)=C(OC)C=C1[125I] PQHQBRJAAZQXHL-GQCOAOBCSA-N 0.000 description 1
- SXDYWXILYKTCNW-UHFFFAOYSA-N 2-[(7-fluoro-9-oxoxanthen-2-yl)sulfonyl-methylamino]acetic acid Chemical compound C1=C(F)C=C2C(=O)C3=CC(S(=O)(=O)N(CC(O)=O)C)=CC=C3OC2=C1 SXDYWXILYKTCNW-UHFFFAOYSA-N 0.000 description 1
- MYZVYSAJIWPJQM-UHFFFAOYSA-N 2-[2,3-dihydro-1h-inden-1-yl-[[4-(dodecylcarbamoyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)C1C2=CC=CC=C2CC1 MYZVYSAJIWPJQM-UHFFFAOYSA-N 0.000 description 1
- PCZNQZFRVCZPHG-UHFFFAOYSA-N 2-[[4-(2-hydroxydodecylamino)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(NCC(O)CCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 PCZNQZFRVCZPHG-UHFFFAOYSA-N 0.000 description 1
- LCBOYAOAHZUZTI-UHFFFAOYSA-N 2-[[4-(dodecylcarbamoyl)phenyl]methyl-(1-naphthalen-1-ylethyl)amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)C(C)C1=CC=CC2=CC=CC=C12 LCBOYAOAHZUZTI-UHFFFAOYSA-N 0.000 description 1
- RVXZFUGODRYVKN-UHFFFAOYSA-N 2-[[4-[dodecyl(methyl)carbamoyl]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)N(C)CCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 RVXZFUGODRYVKN-UHFFFAOYSA-N 0.000 description 1
- IERNOVLNWQROTN-UHFFFAOYSA-N 2-[benzyl-[[4-(pentadecylcarbamoyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical group C1=CC(C(=O)NCCCCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1 IERNOVLNWQROTN-UHFFFAOYSA-N 0.000 description 1
- SHQBSMFUXBZSBC-UHFFFAOYSA-N 2-[benzyl-[[4-(tridecylcarbamoyl)phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(C(=O)NCCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1 SHQBSMFUXBZSBC-UHFFFAOYSA-N 0.000 description 1
- FTIHOVWXUHDSKE-UHFFFAOYSA-N 2-[benzyl-[[4-[(4-hexoxybenzoyl)amino]phenyl]methyl]amino]-2-oxoacetic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NC(C=C1)=CC=C1CN(C(=O)C(O)=O)CC1=CC=CC=C1 FTIHOVWXUHDSKE-UHFFFAOYSA-N 0.000 description 1
- PIHRYUCSBRJHRN-UHFFFAOYSA-N 2-[cyclopentyl-[[5-(dodecylsulfamoyl)thiophen-2-yl]methyl]amino]-2-oxoacetic acid Chemical compound S1C(S(=O)(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(O)=O)C1CCCC1 PIHRYUCSBRJHRN-UHFFFAOYSA-N 0.000 description 1
- CSDKWJMVTKFZLG-UHFFFAOYSA-N 2-bromo-4-tert-butyl-3-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=C(Br)C(C(O)=O)=CC=C1C(C)(C)C CSDKWJMVTKFZLG-UHFFFAOYSA-N 0.000 description 1
- QTTURWMCQQIIEJ-UHFFFAOYSA-N 2-imidazolidin-1-ylacetic acid Chemical compound OC(=O)CN1CCNC1 QTTURWMCQQIIEJ-UHFFFAOYSA-N 0.000 description 1
- QFHAXFPGCYZDAD-UHFFFAOYSA-N 2-oxo-2-[[3-(trifluoromethyl)phenyl]methylamino]acetic acid Chemical compound OC(=O)C(=O)NCC1=CC=CC(C(F)(F)F)=C1 QFHAXFPGCYZDAD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- KEFRQGFIIINVOP-UHFFFAOYSA-N 3-(aminomethyl)-n-dodecylbenzamide Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC(CN)=C1 KEFRQGFIIINVOP-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- LZYNHEOVZMLXIO-UHFFFAOYSA-N 3-(trifluoromethylsulfonyl)aniline Chemical compound NC1=CC=CC(S(=O)(=O)C(F)(F)F)=C1 LZYNHEOVZMLXIO-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- BTWQAVQYOVBTDD-UHFFFAOYSA-N 3-[4-(aminomethyl)phenyl]benzoic acid Chemical compound C1=CC(CN)=CC=C1C1=CC=CC(C(O)=O)=C1 BTWQAVQYOVBTDD-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZFJOMUKPDWNRFI-UHFFFAOYSA-N 3-bromo-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1Br ZFJOMUKPDWNRFI-UHFFFAOYSA-N 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- IGPFOKFDBICQMC-UHFFFAOYSA-N 3-phenylmethoxyaniline Chemical compound NC1=CC=CC(OCC=2C=CC=CC=2)=C1 IGPFOKFDBICQMC-UHFFFAOYSA-N 0.000 description 1
- 125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 description 1
- UVUKURYJAWCRJP-UHFFFAOYSA-N 4-[[(2-ethoxy-2-oxoacetyl)-[[1-(9h-fluoren-9-ylmethoxycarbonyl)piperidin-4-yl]methyl]amino]methyl]benzoic acid Chemical compound C1CN(C(=O)OCC2C3=CC=CC=C3C3=CC=CC=C32)CCC1CN(C(=O)C(=O)OCC)CC1=CC=C(C(O)=O)C=C1 UVUKURYJAWCRJP-UHFFFAOYSA-N 0.000 description 1
- ZYINOLOQOXJYKK-UHFFFAOYSA-N 4-[[(2-ethoxy-2-oxoacetyl)-[[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]methyl]amino]methyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1CN(C(=O)C(=O)OCC)CC1CCN(C(=O)OC(C)(C)C)CC1 ZYINOLOQOXJYKK-UHFFFAOYSA-N 0.000 description 1
- DWRCTDHBDGMIHS-UHFFFAOYSA-N 4-[[(2-methylpropan-2-yl)oxycarbonyl-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]benzoic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)OC(C)(C)C)CC1=CC=C(C(O)=O)C=C1 DWRCTDHBDGMIHS-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- YZEHDFBYSOKBED-UHFFFAOYSA-N 4-isocyanato-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(N=C=O)C=C1 YZEHDFBYSOKBED-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910014585 C2-Ce Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical class C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VXCUURYYWGCLIH-UHFFFAOYSA-N Dodecanenitrile Chemical compound CCCCCCCCCCCC#N VXCUURYYWGCLIH-UHFFFAOYSA-N 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- 108010074860 Factor Xa Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 description 1
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000606506 Homo sapiens Receptor-type tyrosine-protein phosphatase eta Proteins 0.000 description 1
- 102100025087 Insulin receptor substrate 1 Human genes 0.000 description 1
- 101710201824 Insulin receptor substrate 1 Proteins 0.000 description 1
- 229940122254 Intermediate acting insulin Drugs 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 102000016261 Long-Acting Insulin Human genes 0.000 description 1
- 108010092217 Long-Acting Insulin Proteins 0.000 description 1
- 229940100066 Long-acting insulin Drugs 0.000 description 1
- 101710186835 Low molecular weight phosphotyrosine protein phosphatase Proteins 0.000 description 1
- 102100040323 Low molecular weight phosphotyrosine protein phosphatase Human genes 0.000 description 1
- 101710084451 Low molecular weight protein-tyrosine phosphatase A Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 210000005156 Müller Glia Anatomy 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- NNOPDLNHPOLRRE-UHFFFAOYSA-N Nequinate Chemical group CCCCC1=CC(C(C(C(=O)OC)=CN2)=O)=C2C=C1OCC1=CC=CC=C1 NNOPDLNHPOLRRE-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 108010015832 Non-Receptor Type 2 Protein Tyrosine Phosphatase Proteins 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 102000038030 PI3Ks Human genes 0.000 description 1
- 108091007960 PI3Ks Proteins 0.000 description 1
- 108010011536 PTEN Phosphohydrolase Proteins 0.000 description 1
- 102000014160 PTEN Phosphohydrolase Human genes 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 206010036049 Polycystic ovaries Diseases 0.000 description 1
- 108010020346 Polyglutamic Acid Proteins 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 229910019020 PtO2 Inorganic materials 0.000 description 1
- 229940123452 Rapid-acting insulin Drugs 0.000 description 1
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 1
- 108091005682 Receptor kinases Proteins 0.000 description 1
- 102100039808 Receptor-type tyrosine-protein phosphatase eta Human genes 0.000 description 1
- 108010026951 Short-Acting Insulin Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 102100033141 Tyrosine-protein phosphatase non-receptor type 2 Human genes 0.000 description 1
- 102100021657 Tyrosine-protein phosphatase non-receptor type 6 Human genes 0.000 description 1
- 101710128901 Tyrosine-protein phosphatase non-receptor type 6 Proteins 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- YKNZTUQUXUXTLE-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(C(F)(F)F)=C1 YKNZTUQUXUXTLE-UHFFFAOYSA-N 0.000 description 1
- WUUGGOQPXZDQNW-UHFFFAOYSA-N [4-(thiadiazol-4-yl)phenyl]methanamine;hydrochloride Chemical compound Cl.C1=CC(CN)=CC=C1C1=CSN=N1 WUUGGOQPXZDQNW-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- WSLOHMLGIVSUPR-UHFFFAOYSA-N adn-138 Chemical compound C1COC2=CC(Cl)=CC3=C2N1C(=O)C31CC(=O)NC1=O WSLOHMLGIVSUPR-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940127003 anti-diabetic drug Drugs 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000035578 autophosphorylation Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- WLSHPBJFIDPHOZ-UHFFFAOYSA-N benzyl 4-[[(2-ethoxy-2-oxoacetyl)-[[4-(trifluoromethyl)phenyl]methyl]amino]methyl]benzoate Chemical compound C=1C=C(C(F)(F)F)C=CC=1CN(C(=O)C(=O)OCC)CC(C=C1)=CC=C1C(=O)OCC1=CC=CC=C1 WLSHPBJFIDPHOZ-UHFFFAOYSA-N 0.000 description 1
- XOEIKJVLLHUKCE-UHFFFAOYSA-N benzyl 4-[[benzyl-(2-ethoxy-2-oxoacetyl)amino]methyl]benzoate Chemical compound C=1C=C(C(=O)OCC=2C=CC=CC=2)C=CC=1CN(C(=O)C(=O)OCC)CC1=CC=CC=C1 XOEIKJVLLHUKCE-UHFFFAOYSA-N 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000023402 cell communication Effects 0.000 description 1
- 230000017455 cell-cell adhesion Effects 0.000 description 1
- 230000035289 cell-matrix adhesion Effects 0.000 description 1
- 210000003570 cell-matrix junction Anatomy 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 150000003841 chloride salts Chemical group 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000030609 dephosphorylation Effects 0.000 description 1
- 238000006209 dephosphorylation reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 239000003596 drug target Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 210000002472 endoplasmic reticulum Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MMMPWWNMCWRCKX-UHFFFAOYSA-N ethyl 2-[[4-(dodecylcarbamoyl)phenyl]methyl-[[3-(trifluoromethyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=CC(C(F)(F)F)=C1 MMMPWWNMCWRCKX-UHFFFAOYSA-N 0.000 description 1
- FETSCABRENJBFX-UHFFFAOYSA-N ethyl 2-[benzyl-[[3-(dodecylcarbamoyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound CCCCCCCCCCCCNC(=O)C1=CC=CC(CN(CC=2C=CC=CC=2)C(=O)C(=O)OCC)=C1 FETSCABRENJBFX-UHFFFAOYSA-N 0.000 description 1
- BAGPJSVKOCGIAV-UHFFFAOYSA-N ethyl 2-[benzyl-[[4-(pentadecylcarbamoyl)phenyl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=CC=C1 BAGPJSVKOCGIAV-UHFFFAOYSA-N 0.000 description 1
- CNYLMPHGXNHDKC-UHFFFAOYSA-N ethyl 2-[benzyl-[[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]methyl]amino]-2-oxoacetate Chemical compound C=1C=C(NC(=O)OC(C)(C)C)C=CC=1CN(C(=O)C(=O)OCC)CC1=CC=CC=C1 CNYLMPHGXNHDKC-UHFFFAOYSA-N 0.000 description 1
- XKUNKTSCEAGVNT-UHFFFAOYSA-N ethyl 2-[benzyl-[[4-[(4-hexoxybenzoyl)amino]phenyl]methyl]amino]-2-oxoacetate Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)NC(C=C1)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=CC=C1 XKUNKTSCEAGVNT-UHFFFAOYSA-N 0.000 description 1
- MKORAPFNCCZBKJ-UHFFFAOYSA-N ethyl 2-oxo-2-[[4-(pentadecylcarbamoyl)phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]acetate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCCCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=C(C(F)(F)F)C=C1 MKORAPFNCCZBKJ-UHFFFAOYSA-N 0.000 description 1
- PIBQVQCGPYWWIU-BQYQJAHWSA-N ethyl 2-oxo-2-[[4-[[(e)-tetradec-9-enoyl]amino]phenyl]methyl-[[4-(trifluoromethyl)phenyl]methyl]amino]acetate Chemical compound C1=CC(NC(=O)CCCCCCC/C=C/CCCC)=CC=C1CN(C(=O)C(=O)OCC)CC1=CC=C(C(F)(F)F)C=C1 PIBQVQCGPYWWIU-BQYQJAHWSA-N 0.000 description 1
- DBPFRRFGLYGEJI-UHFFFAOYSA-N ethyl glyoxylate Chemical compound CCOC(=O)C=O DBPFRRFGLYGEJI-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960004580 glibenclamide Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 201000010066 hyperandrogenism Diseases 0.000 description 1
- 230000035879 hyperinsulinaemia Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000004155 insulin signaling pathway Effects 0.000 description 1
- 208000023589 ischemic disease Diseases 0.000 description 1
- 210000004153 islets of langerhan Anatomy 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
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DYIFGWMFPGRQPY-UHFFFAOYSA-N methyl 2-[[4-(dodecylcarbamoyl)-n-(2-ethoxy-2-oxoacetyl)anilino]methyl]benzoate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1N(C(=O)C(=O)OCC)CC1=CC=CC=C1C(=O)OC DYIFGWMFPGRQPY-UHFFFAOYSA-N 0.000 description 1
- DMADTFFYXDOGQW-UHFFFAOYSA-N methyl 2-[[4-(dodecylcarbamoyl)anilino]methyl]benzoate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1NCC1=CC=CC=C1C(=O)OC DMADTFFYXDOGQW-UHFFFAOYSA-N 0.000 description 1
- YRMODRRGEUGHTF-UHFFFAOYSA-N methyl 2-formylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C=O YRMODRRGEUGHTF-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GZCNKQPANHRSAJ-UHFFFAOYSA-N n-[3,5-dimethyl-4-(nitromethylsulfonyl)phenyl]-2-(2-methylphenyl)acetamide Chemical compound CC1=CC=CC=C1CC(=O)NC1=CC(C)=C(S(=O)(=O)C[N+]([O-])=O)C(C)=C1 GZCNKQPANHRSAJ-UHFFFAOYSA-N 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
- RHWSJHVQADQCGW-UHFFFAOYSA-N n-dodecyl-4-[(1-naphthalen-1-ylethylamino)methyl]benzamide Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CNC(C)C1=CC=CC2=CC=CC=C12 RHWSJHVQADQCGW-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- YXMXAXHPRPWBJB-UHFFFAOYSA-N n-phenoxy-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CNOC1=CC=CC=C1 YXMXAXHPRPWBJB-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000003061 neural cell Anatomy 0.000 description 1
- 210000002241 neurite Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000007410 oral glucose tolerance test Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000369 oxido group Chemical group [*]=O 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000005475 oxolanyl group Chemical group 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000012660 pharmacological inhibitor Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- JBMJCQARHLHKRJ-UHFFFAOYSA-N spiro[9-oxa-1-azatricyclo[6.3.1.04,12]dodeca-4(12),5,7,10-tetraene-3,3'-pyrrolidine]-2,2',5'-trione Chemical compound O=C1NC(=O)CC21C(C=CC=C1OC=C3)=C1N3C2=O JBMJCQARHLHKRJ-UHFFFAOYSA-N 0.000 description 1
- LQQTXLXDYXLCCG-UHFFFAOYSA-N spiro[chromene-4,5'-imidazolidine]-2',4'-dione Chemical compound N1C(=O)NC(=O)C21C1=CC=CC=C1OC=C2 LQQTXLXDYXLCCG-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WOQMYWUAPXRZQS-UHFFFAOYSA-N tert-butyl 3-(4-methylphenyl)benzoate Chemical compound C1=CC(C)=CC=C1C1=CC=CC(C(=O)OC(C)(C)C)=C1 WOQMYWUAPXRZQS-UHFFFAOYSA-N 0.000 description 1
- NKXTVJYWJFHXNB-UHFFFAOYSA-N tert-butyl 4-[[[4-(dodecylcarbamoyl)phenyl]methylamino]methyl]piperidine-1-carboxylate Chemical compound C1=CC(C(=O)NCCCCCCCCCCCC)=CC=C1CNCC1CCN(C(=O)OC(C)(C)C)CC1 NKXTVJYWJFHXNB-UHFFFAOYSA-N 0.000 description 1
- BFJJYXUCGYOXDM-UHFFFAOYSA-N tert-butyl 4-bromobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(Br)C=C1 BFJJYXUCGYOXDM-UHFFFAOYSA-N 0.000 description 1
- WJFWIRWHYIDBAQ-UHFFFAOYSA-N tert-butyl 5-amino-1,3-dihydroisoindole-2-carboxylate Chemical compound C1=C(N)C=C2CN(C(=O)OC(C)(C)C)CC2=C1 WJFWIRWHYIDBAQ-UHFFFAOYSA-N 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LRNOJDNYMHAKLY-UHFFFAOYSA-N tetradec-9-enoyl chloride Chemical compound CCCCC=CCCCCCCCC(Cl)=O LRNOJDNYMHAKLY-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 230000035924 thermogenesis Effects 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000014348 vinaigrettes Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/56—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having carbon atoms of carboxamide groups bound to carbon atoms of carboxyl groups, e.g. oxamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D401/04—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Child & Adolescent Psychology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02100078 | 2002-01-29 | ||
EP02100410 | 2002-04-25 | ||
PCT/EP2003/000808 WO2003064376A1 (en) | 2002-01-29 | 2003-01-27 | Substituted methylene amide derivatives as modulators of protein tyrosine phosphatases (ptps) |
Publications (2)
Publication Number | Publication Date |
---|---|
NO20043520L NO20043520L (no) | 2004-10-05 |
NO329742B1 true NO329742B1 (no) | 2010-12-13 |
Family
ID=27664997
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20043520A NO329742B1 (no) | 2002-01-29 | 2004-08-24 | Substituerte metylenamidderivater, anvendelse av metylenamidderivatene for fremstilling av medikamenter og farmasoytiske sammensetninger, farmasoytiske sammensetninger som innholder metylenamidderivatene og fremgangsmater for fremstilling av de substituerte mtylenamidderivatene |
Country Status (24)
Country | Link |
---|---|
US (1) | US7592477B2 (zh) |
EP (1) | EP1470102B1 (zh) |
JP (2) | JP4828793B2 (zh) |
KR (1) | KR100922041B1 (zh) |
CN (1) | CN100410236C (zh) |
AT (1) | ATE510817T1 (zh) |
AU (1) | AU2003239296B2 (zh) |
BR (1) | BR0307394A (zh) |
CA (1) | CA2472021C (zh) |
CY (1) | CY1111576T1 (zh) |
DK (1) | DK1470102T3 (zh) |
EA (1) | EA012260B1 (zh) |
HK (1) | HK1073649A1 (zh) |
HR (1) | HRP20040612A2 (zh) |
IL (1) | IL163144A (zh) |
MX (1) | MXPA04007253A (zh) |
NO (1) | NO329742B1 (zh) |
PL (1) | PL207295B1 (zh) |
PT (1) | PT1470102E (zh) |
RS (1) | RS51865B (zh) |
SI (1) | SI1470102T1 (zh) |
UA (1) | UA82661C2 (zh) |
WO (1) | WO2003064376A1 (zh) |
ZA (1) | ZA200405179B (zh) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5198768B2 (ja) | 2003-07-21 | 2013-05-15 | メルク セローノ ソシエテ アノニム | アルキニルアリールカルボキサミド |
JP2006528157A (ja) * | 2003-07-21 | 2006-12-14 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | アリールジカルボキシアミド |
CA2539155C (en) | 2003-10-13 | 2012-08-07 | Applied Research Systems Ars Holding N.V. | Method for preparing para-phenyl alkynyl benzaldehydes |
AU2005216649B2 (en) * | 2004-02-27 | 2010-09-09 | Merck Serono Sa | Use of methylene amide derivatives in cardiovascular disorders |
CN1997638B (zh) | 2004-04-07 | 2011-07-06 | 默克雪兰诺有限公司 | 作为ptp1-b抑制剂的1,1'-(1,2-乙炔二基)双苯衍生物 |
EP1737811B1 (en) * | 2004-04-13 | 2016-08-10 | Merck Sharp & Dohme Corp. | Cetp inhibitors |
US7517991B2 (en) * | 2004-10-12 | 2009-04-14 | Bristol-Myers Squibb Company | N-sulfonylpiperidine cannabinoid receptor 1 antagonists |
EP1904048B1 (en) * | 2005-07-15 | 2011-11-23 | Merck Serono SA | Glepp-1 inhibitors in the treatment of autoimmune and/or inflammatory disorders |
WO2007028145A2 (en) * | 2005-09-02 | 2007-03-08 | Dara Biosciences, Inc. | Agents and methods for reducing protein tyrosine phosphatase 1b activity in the central nervous system |
US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
CN101378731B (zh) | 2006-02-09 | 2014-03-05 | 默沙东公司 | Cetp抑制剂的聚合物制剂 |
US20090018169A1 (en) * | 2006-02-13 | 2009-01-15 | Laboratoires Serono Sa | Sulfonamide Derivatives for the Treatment of Bacterial Infections |
AU2007307599A1 (en) * | 2006-10-12 | 2008-04-17 | Institute Of Medicinal Molecular Design. Inc. | N-phenyloxamic acid derivatives |
US8633245B2 (en) * | 2008-04-11 | 2014-01-21 | Institute Of Medicinal Molecular Design, Inc. | PAI-1 inhibitor |
TW201213502A (en) | 2010-08-05 | 2012-04-01 | Idemitsu Kosan Co | Organic electroluminescent element |
CN102512407B (zh) * | 2011-11-23 | 2014-05-21 | 中山大学 | 一种β-苯丙氨酸类化合物作为醛糖还原酶抑制剂的应用 |
WO2014074365A1 (en) * | 2012-11-06 | 2014-05-15 | Eli Lilly And Company | Novel benzyl sulfonamide compounds useful as mogat-2 inhibitors |
CA2921427A1 (en) * | 2013-08-16 | 2015-02-19 | Duke University | Substituted hydroxamic acid compounds |
EP3883574A1 (en) * | 2018-11-23 | 2021-09-29 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Use of shp2 inhibitors for the treatment of insulin resistance |
CN115297860B (zh) * | 2020-04-06 | 2024-10-15 | 普渡研究基金会 | 新型n-芳基草氨酸 |
CN114478522B (zh) * | 2022-01-25 | 2023-07-28 | 山东大学 | 一种吡啶并咪唑类衍生物及其制备方法与应用 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5217482A (en) * | 1975-07-25 | 1977-02-09 | Sumitomo Chem Co Ltd | Preparation of quinazolinone derivatives |
CA2054339C (en) * | 1990-11-02 | 2002-12-24 | Francesco G. Salituro | 3-amidoindolyl derivatives |
ATE233240T1 (de) | 1994-12-02 | 2003-03-15 | Yamanouchi Pharma Co Ltd | Neues amidinonaphthylderivat oder dessen salz |
JPH08295667A (ja) * | 1995-04-27 | 1996-11-12 | Takeda Chem Ind Ltd | 複素環化合物、その製造法および剤 |
JP3283485B2 (ja) * | 1998-04-10 | 2002-05-20 | 日本たばこ産業株式会社 | アミジン化合物 |
US6488973B1 (en) * | 1998-10-05 | 2002-12-03 | Food Talk, Inc. | Method of making a cooking pouch containing a raw protein portion, a raw or blanched vegetable portion and a sauce |
WO2000023428A1 (fr) * | 1998-10-20 | 2000-04-27 | Takeda Chemical Industries, Ltd. | Composes de 1,5-benzodiazepine, procede de production de ces composes, et medicament |
DE60028791T2 (de) | 1999-09-10 | 2007-05-24 | Novo Nordisk A/S | Modulatoren der protein tyrosin phosphatase (ptpases) |
US6627767B2 (en) * | 2000-08-29 | 2003-09-30 | Abbott Laboratories | Amino(oxo) acetic acid protein tyrosine phosphatase inhibitors |
WO2002018321A2 (en) * | 2000-08-29 | 2002-03-07 | Abbott Laboratories | Amino(oxo)acetic acid protein tyrosine phosphatase inhibitors |
WO2002100396A1 (en) | 2001-06-07 | 2002-12-19 | Wyeth | COMBINATION OF A PTPase INHIBITOR AND A THIAZOLIDINEDIONE AGENT |
AU2005216649B2 (en) * | 2004-02-27 | 2010-09-09 | Merck Serono Sa | Use of methylene amide derivatives in cardiovascular disorders |
-
2003
- 2003-01-27 CN CNB038070367A patent/CN100410236C/zh not_active Expired - Fee Related
- 2003-01-27 EP EP03734697A patent/EP1470102B1/en not_active Expired - Lifetime
- 2003-01-27 MX MXPA04007253A patent/MXPA04007253A/es active IP Right Grant
- 2003-01-27 CA CA2472021A patent/CA2472021C/en not_active Expired - Fee Related
- 2003-01-27 RS YU65304A patent/RS51865B/sr unknown
- 2003-01-27 WO PCT/EP2003/000808 patent/WO2003064376A1/en active Application Filing
- 2003-01-27 SI SI200332010T patent/SI1470102T1/sl unknown
- 2003-01-27 AT AT03734697T patent/ATE510817T1/de active
- 2003-01-27 AU AU2003239296A patent/AU2003239296B2/en not_active Ceased
- 2003-01-27 JP JP2003564000A patent/JP4828793B2/ja not_active Expired - Fee Related
- 2003-01-27 DK DK03734697.0T patent/DK1470102T3/da active
- 2003-01-27 UA UA20040706337A patent/UA82661C2/uk unknown
- 2003-01-27 KR KR1020047011772A patent/KR100922041B1/ko not_active IP Right Cessation
- 2003-01-27 US US10/501,344 patent/US7592477B2/en not_active Expired - Fee Related
- 2003-01-27 EA EA200400882A patent/EA012260B1/ru not_active IP Right Cessation
- 2003-01-27 BR BR0307394-7A patent/BR0307394A/pt not_active IP Right Cessation
- 2003-01-27 PT PT03734697T patent/PT1470102E/pt unknown
- 2003-01-27 PL PL371198A patent/PL207295B1/pl not_active IP Right Cessation
-
2004
- 2004-06-29 ZA ZA2004/05179A patent/ZA200405179B/en unknown
- 2004-07-06 HR HR20040612A patent/HRP20040612A2/xx not_active Application Discontinuation
- 2004-07-22 IL IL163144A patent/IL163144A/en not_active IP Right Cessation
- 2004-08-24 NO NO20043520A patent/NO329742B1/no not_active IP Right Cessation
-
2005
- 2005-08-30 HK HK05107572A patent/HK1073649A1/xx not_active IP Right Cessation
-
2011
- 2011-06-16 CY CY20111100576T patent/CY1111576T1/el unknown
- 2011-06-30 JP JP2011146082A patent/JP2011256174A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
KR20040104953A (ko) | 2004-12-13 |
EP1470102B1 (en) | 2011-05-25 |
SI1470102T1 (sl) | 2011-08-31 |
DK1470102T3 (da) | 2011-06-20 |
ZA200405179B (en) | 2005-08-31 |
US20050124656A1 (en) | 2005-06-09 |
US7592477B2 (en) | 2009-09-22 |
WO2003064376A1 (en) | 2003-08-07 |
EP1470102A1 (en) | 2004-10-27 |
MXPA04007253A (es) | 2004-10-29 |
JP4828793B2 (ja) | 2011-11-30 |
JP2011256174A (ja) | 2011-12-22 |
PL371198A1 (en) | 2005-06-13 |
EA012260B1 (ru) | 2009-08-28 |
CN1633410A (zh) | 2005-06-29 |
IL163144A (en) | 2012-07-31 |
CA2472021A1 (en) | 2003-08-07 |
ATE510817T1 (de) | 2011-06-15 |
PL207295B1 (pl) | 2010-11-30 |
PT1470102E (pt) | 2011-06-06 |
RS51865B (sr) | 2012-02-29 |
JP2005516061A (ja) | 2005-06-02 |
HRP20040612A2 (en) | 2005-04-30 |
HK1073649A1 (en) | 2005-10-14 |
CN100410236C (zh) | 2008-08-13 |
UA82661C2 (uk) | 2008-05-12 |
CY1111576T1 (el) | 2015-10-07 |
NO20043520L (no) | 2004-10-05 |
BR0307394A (pt) | 2004-11-09 |
CA2472021C (en) | 2012-08-14 |
EA200400882A1 (ru) | 2005-04-28 |
RS65304A (en) | 2007-02-05 |
AU2003239296B2 (en) | 2008-10-23 |
KR100922041B1 (ko) | 2009-10-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO329742B1 (no) | Substituerte metylenamidderivater, anvendelse av metylenamidderivatene for fremstilling av medikamenter og farmasoytiske sammensetninger, farmasoytiske sammensetninger som innholder metylenamidderivatene og fremgangsmater for fremstilling av de substituerte mtylenamidderivatene | |
JP5043645B2 (ja) | カルボン酸 | |
AU2003239296A1 (en) | Substituted methylene amide derivatives as Modulators of Protein Tyrosine Phosphatases (PTPs) | |
AU2010200531A1 (en) | Glycogen phosphorylase inhibitor compounds and pharmaceutical compositions thereof | |
EP1654247B1 (en) | Alkynyl aryl carboxamides | |
EP1656139B1 (en) | Aryl dicarboxamides | |
JP2006528157A5 (zh) | ||
ES2366905T3 (es) | Derivados de metilenamida sustituidos en calidad de moduladores de proteína tirosina fosfatasas (ptps). |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
CREP | Change of representative |
Representative=s name: ONSAGERS AS, POSTBOKS 6963 ST OLAVS PLASS, 0130 OS |
|
MM1K | Lapsed by not paying the annual fees |