CA2692598A1 - Derives de l'uree et de diamines associees, leurs procedes de fabrication, et leurs utilisations - Google Patents
Derives de l'uree et de diamines associees, leurs procedes de fabrication, et leurs utilisations Download PDFInfo
- Publication number
- CA2692598A1 CA2692598A1 CA 2692598 CA2692598A CA2692598A1 CA 2692598 A1 CA2692598 A1 CA 2692598A1 CA 2692598 CA2692598 CA 2692598 CA 2692598 A CA2692598 A CA 2692598A CA 2692598 A1 CA2692598 A1 CA 2692598A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- diphenylpropyl
- thiazol
- amino
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 286
- 150000004985 diamines Chemical class 0.000 title description 3
- 150000003672 ureas Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 262
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
- 208000035475 disorder Diseases 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 10
- -1 dimethylene group Chemical group 0.000 claims description 190
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 77
- 150000003839 salts Chemical class 0.000 claims description 62
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 52
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 18
- 206010012735 Diarrhoea Diseases 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- ZACUJFIIPRZJOC-UHFFFAOYSA-N 3-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]benzoic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=C(C=CC=2)C(O)=O)=N1 ZACUJFIIPRZJOC-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 229940124530 sulfonamide Drugs 0.000 claims description 13
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 12
- 125000004442 acylamino group Chemical group 0.000 claims description 12
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 208000005475 Vascular calcification Diseases 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 10
- DCJWOUKIVOTXAW-UHFFFAOYSA-N 3-[5-chloro-4-[4-(hydroxymethyl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-[2-(oxan-4-yl)ethyl]urea Chemical compound C1=CC(CO)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC2CCOCC2)=N1 DCJWOUKIVOTXAW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 210000000557 podocyte Anatomy 0.000 claims description 8
- 125000001174 sulfone group Chemical group 0.000 claims description 8
- 125000004001 thioalkyl group Chemical group 0.000 claims description 8
- 230000002159 abnormal effect Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- NPGCSDOTXJJGOK-UHFFFAOYSA-N 3-[5-chloro-4-[4-(hydroxymethyl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-propan-2-ylurea Chemical compound N=1C(C=2C=CC(CO)=CC=2)=C(Cl)SC=1NC(=O)N(C(C)C)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 NPGCSDOTXJJGOK-UHFFFAOYSA-N 0.000 claims description 6
- PJADPCCRORXZQD-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-methylurea Chemical compound N=1C(C=2C=CC(NS(C)(=O)=O)=CC=2)=C(Cl)SC=1NC(=O)N(C)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 PJADPCCRORXZQD-UHFFFAOYSA-N 0.000 claims description 6
- NIIRFCZAPMBUDM-UHFFFAOYSA-N 4-[1,3-benzothiazol-2-ylcarbamoyl(3,3-diphenylpropyl)amino]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1N(C(=O)NC=1SC2=CC=CC=C2N=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 NIIRFCZAPMBUDM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003172 aldehyde group Chemical group 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- KCZVNTBBWQGMMJ-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-propan-2-ylurea Chemical compound N=1C(C=2C=CC(NS(C)(=O)=O)=CC=2)=CSC=1NC(=O)N(C(C)C)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 KCZVNTBBWQGMMJ-UHFFFAOYSA-N 0.000 claims description 5
- USLNXSDONWYRFN-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]phenyl]acetic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC(CC(O)=O)=CC=2)=N1 USLNXSDONWYRFN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000001965 increasing effect Effects 0.000 claims description 5
- 230000008991 intestinal motility Effects 0.000 claims description 5
- 208000015380 nutritional deficiency disease Diseases 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- HRGAURTYKULADY-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-methyl-3-(4-phenyl-1,3-thiazol-2-yl)urea Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1NC(=O)N(C)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 HRGAURTYKULADY-UHFFFAOYSA-N 0.000 claims description 4
- AZIFEQTWSIFKJM-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-(3-methoxyphenyl)-1-(2-methylpropyl)urea Chemical compound COC1=CC=CC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC(C)C)=C1 AZIFEQTWSIFKJM-UHFFFAOYSA-N 0.000 claims description 4
- RJESAVXJLXLTFB-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]-1-(2-piperidin-4-ylethyl)urea Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC2CCNCC2)=N1 RJESAVXJLXLTFB-UHFFFAOYSA-N 0.000 claims description 4
- OALHLQSZEVEJCB-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(2-piperidin-3-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC2CNCCC2)=N1 OALHLQSZEVEJCB-UHFFFAOYSA-N 0.000 claims description 4
- OLWYWDJFVLIKHG-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(2-piperidin-4-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC2CCNCC2)=N1 OLWYWDJFVLIKHG-UHFFFAOYSA-N 0.000 claims description 4
- UACHQPBDRSLWOF-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-propylurea Chemical compound N=1C(C=2C=CC(NS(C)(=O)=O)=CC=2)=CSC=1NC(=O)N(CCC)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 UACHQPBDRSLWOF-UHFFFAOYSA-N 0.000 claims description 4
- RPMBXBLTTFHWLJ-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[5-chloro-4-(4-sulfamoylphenyl)-1,3-thiazol-2-yl]-1-cyclopropylurea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)C2CC2)=N1 RPMBXBLTTFHWLJ-UHFFFAOYSA-N 0.000 claims description 4
- OLQKRTSHJBUICH-UHFFFAOYSA-N 1-cyclopropyl-1-(3,3-diphenylpropyl)-3-[4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CC2)=N1 OLQKRTSHJBUICH-UHFFFAOYSA-N 0.000 claims description 4
- AITMPYIQNVYIBL-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1-(3,3-diphenylpropyl)-1-propan-2-ylurea Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)N(C(C)C)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 AITMPYIQNVYIBL-UHFFFAOYSA-N 0.000 claims description 4
- UUIUELBLXNNIMF-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1-(3,3-diphenylpropyl)-1-propylurea Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)N(CCC)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 UUIUELBLXNNIMF-UHFFFAOYSA-N 0.000 claims description 4
- VTALQYIVQZDWRR-UHFFFAOYSA-N 3-[5-chloro-4-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-piperidin-4-ylethyl)urea Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC2CCNCC2)=N1 VTALQYIVQZDWRR-UHFFFAOYSA-N 0.000 claims description 4
- GTQRPYUBSCNURT-UHFFFAOYSA-N 3-[5-chloro-4-(4-sulfamoylphenyl)-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-pyridin-2-ylethyl)urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CC=2)=N1 GTQRPYUBSCNURT-UHFFFAOYSA-N 0.000 claims description 4
- CNIUALCPWIVVDR-UHFFFAOYSA-N 3-[5-chloro-4-(4-sulfamoylphenyl)-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-[2-(oxan-4-yl)ethyl]urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC2CCOCC2)=N1 CNIUALCPWIVVDR-UHFFFAOYSA-N 0.000 claims description 4
- XUFRZYADNMCTKR-UHFFFAOYSA-N 3-[5-chloro-4-(6-methylpyridin-3-yl)-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-piperidin-4-ylurea Chemical compound C1=NC(C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CCNCC2)=N1 XUFRZYADNMCTKR-UHFFFAOYSA-N 0.000 claims description 4
- DOYBEVPHIOZZNR-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(2-cyanoethyl)-1-(3,3-diphenylpropyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC#N)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 DOYBEVPHIOZZNR-UHFFFAOYSA-N 0.000 claims description 4
- JEOCZTFYUDFTEJ-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-piperidin-3-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC2CNCCC2)=N1 JEOCZTFYUDFTEJ-UHFFFAOYSA-N 0.000 claims description 4
- MXGKZYXCFFJDIO-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-pyridin-2-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CC=2)=N1 MXGKZYXCFFJDIO-UHFFFAOYSA-N 0.000 claims description 4
- FVMWKCAAGYSODJ-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-pyridin-3-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2C=NC=CC=2)=N1 FVMWKCAAGYSODJ-UHFFFAOYSA-N 0.000 claims description 4
- OVMAMDGPCNDIKV-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-pyridin-4-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2C=CN=CC=2)=N1 OVMAMDGPCNDIKV-UHFFFAOYSA-N 0.000 claims description 4
- UMIIJVFNCZOMCB-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(3-phenylpropyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCCC=2C=CC=CC=2)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 UMIIJVFNCZOMCB-UHFFFAOYSA-N 0.000 claims description 4
- HMWKDYDNYFKDQW-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-[2-(4-methoxyphenyl)ethyl]urea Chemical compound C1=CC(OC)=CC=C1CCN(C(=O)NC=1SC(Cl)=C(N=1)C=1C=CC(NS(C)(=O)=O)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 HMWKDYDNYFKDQW-UHFFFAOYSA-N 0.000 claims description 4
- VSRSWYHTUMCGAZ-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-phenylurea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 VSRSWYHTUMCGAZ-UHFFFAOYSA-N 0.000 claims description 4
- OKARARGFKYNAOK-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-cyclohexyl-1-(3,3-diphenylpropyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CCCCC2)=N1 OKARARGFKYNAOK-UHFFFAOYSA-N 0.000 claims description 4
- LBEAGSHXLDXIEU-UHFFFAOYSA-N 3-[5-chloro-4-[4-(morpholin-4-ylmethyl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(oxan-4-yl)urea Chemical compound N=1C(C=2C=CC(CN3CCOCC3)=CC=2)=C(Cl)SC=1NC(=O)N(C1CCOCC1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 LBEAGSHXLDXIEU-UHFFFAOYSA-N 0.000 claims description 4
- WOPQNHSLIVELFV-UHFFFAOYSA-N 3-[5-chloro-4-[4-(piperazin-1-ylmethyl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-propan-2-ylurea Chemical compound N=1C(C=2C=CC(CN3CCNCC3)=CC=2)=C(Cl)SC=1NC(=O)N(C(C)C)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 WOPQNHSLIVELFV-UHFFFAOYSA-N 0.000 claims description 4
- RKGNVZZXERDKIJ-UHFFFAOYSA-N 3-[5-chloro-4-[4-(triazol-1-yl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-pyridin-2-ylethyl)urea Chemical compound N=1C(C=2C=CC(=CC=2)N2N=NC=C2)=C(Cl)SC=1NC(=O)N(CCC=1N=CC=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 RKGNVZZXERDKIJ-UHFFFAOYSA-N 0.000 claims description 4
- YNGLWJYHGXXLQM-UHFFFAOYSA-N 3-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C(=O)NC=2SC(Cl)=C(N=2)C=2C=CC(NS(C)(=O)=O)=CC=2)=C1 YNGLWJYHGXXLQM-UHFFFAOYSA-N 0.000 claims description 4
- YSHHNIOKMSZXOI-UHFFFAOYSA-N 4-[2-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]ethyl]benzoic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2C=CC(=CC=2)C(O)=O)=N1 YSHHNIOKMSZXOI-UHFFFAOYSA-N 0.000 claims description 4
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- KAWDYMZZQISRHV-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[3-[4-(methanesulfonamido)phenyl]-1,2,4-thiadiazol-5-yl]-1-(oxan-4-yl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CCOCC2)=N1 KAWDYMZZQISRHV-UHFFFAOYSA-N 0.000 claims description 2
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- IHVWNPFIECNCBW-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[5-[4-(methanesulfonamido)phenyl]-1,2,4-thiadiazol-3-yl]-1-(2-pyridin-2-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=NC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CC=2)=NS1 IHVWNPFIECNCBW-UHFFFAOYSA-N 0.000 claims description 2
- LWSBRPGOCOQEMA-UHFFFAOYSA-N 1-[2-(4-chloropyridin-2-yl)ethyl]-1-(3,3-diphenylpropyl)-3-[3-[4-(triazol-1-yl)phenyl]-1,2,4-thiadiazol-5-yl]urea Chemical compound ClC1=CC=NC(CCN(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C(=O)NC=2SN=C(N=2)C=2C=CC(=CC=2)N2N=NC=C2)=C1 LWSBRPGOCOQEMA-UHFFFAOYSA-N 0.000 claims description 2
- AOKNTQVNBDYBGY-UHFFFAOYSA-N 1-[2-(5-chloropyridin-2-yl)ethyl]-3-[5-chloro-4-[4-(triazol-1-yl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)urea Chemical compound N=1C(C=2C=CC(=CC=2)N2N=NC=C2)=C(Cl)SC=1NC(=O)N(CCC=1N=CC(Cl)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 AOKNTQVNBDYBGY-UHFFFAOYSA-N 0.000 claims description 2
- AHCZNAKOFZKKBH-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-1-(2-pyrazin-2-ylethyl)-3-[3-(4-sulfamoylphenyl)-1,2,4-thiadiazol-5-yl]urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=NC=2)=N1 AHCZNAKOFZKKBH-UHFFFAOYSA-N 0.000 claims description 2
- DMZGMDYTANTJSC-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-1-(2-pyridin-2-ylethyl)-3-[3-(4-sulfamoylphenyl)-1,2,4-thiadiazol-5-yl]urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CC=2)=N1 DMZGMDYTANTJSC-UHFFFAOYSA-N 0.000 claims description 2
- NHGBBRKFZIWKNG-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-1-(2-pyridin-2-ylethyl)-3-[3-[4-(triazol-1-yl)phenyl]-1,2,4-thiadiazol-5-yl]urea Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCN(C(=O)NC=1SN=C(N=1)C=1C=CC(=CC=1)N1N=NC=C1)CCC1=CC=CC=N1 NHGBBRKFZIWKNG-UHFFFAOYSA-N 0.000 claims description 2
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- ADGAPAYEXWEBQW-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-1-cyclopropyl-3-[3-[4-(methanesulfonamido)phenyl]-1,2,4-thiadiazol-5-yl]urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)C2CC2)=N1 ADGAPAYEXWEBQW-UHFFFAOYSA-N 0.000 claims description 2
- NNBWJPWNZZBQFV-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[3-(4-methylsulfonylphenyl)-1,2,4-thiadiazol-5-yl]-1-(2-pyrazin-2-ylethyl)urea Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=NC=2)=N1 NNBWJPWNZZBQFV-UHFFFAOYSA-N 0.000 claims description 2
- DCPKYHGPQRGTLX-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[3-(4-methylsulfonylphenyl)-1,2,4-thiadiazol-5-yl]-1-(2-pyridin-2-ylethyl)urea Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CC=2)=N1 DCPKYHGPQRGTLX-UHFFFAOYSA-N 0.000 claims description 2
- QQTJMZKEZXQPBS-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[3-[4-(methanesulfonamido)phenyl]-1,2,4-thiadiazol-5-yl]-1-(2-pyrazin-2-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=NC=2)=N1 QQTJMZKEZXQPBS-UHFFFAOYSA-N 0.000 claims description 2
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- RWSMBLWKGJMXDJ-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[5-chloro-4-(4-sulfamoylphenyl)-1,3-thiazol-2-yl]-1-(2-pyridin-2-ylethyl)urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CC=2)=N1 RWSMBLWKGJMXDJ-UHFFFAOYSA-N 0.000 claims description 2
- OAOQSRBQWOLANF-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[5-chloro-4-(4-sulfamoylphenyl)-1,3-thiazol-2-yl]-1-(2-pyrimidin-2-ylethyl)urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CN=2)=N1 OAOQSRBQWOLANF-UHFFFAOYSA-N 0.000 claims description 2
- ZCCSRANATLOSRH-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(2-pyrazin-2-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=NC=2)=N1 ZCCSRANATLOSRH-UHFFFAOYSA-N 0.000 claims description 2
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- QQUZTLOUQPDQIC-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(2-pyrimidin-2-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CN=2)=N1 QQUZTLOUQPDQIC-UHFFFAOYSA-N 0.000 claims description 2
- DEGKBUOTALGDGP-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-3-[5-chloro-4-[4-(triazol-1-yl)phenyl]-1,3-thiazol-2-yl]-1-(2-pyrazin-2-ylethyl)urea Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCN(C(=O)NC=1SC(Cl)=C(N=1)C=1C=CC(=CC=1)N1N=NC=C1)CCC1=CN=CC=N1 DEGKBUOTALGDGP-UHFFFAOYSA-N 0.000 claims description 2
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- OEKLCVUTIHEXNR-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-pyrimidin-2-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CN=2)=N1 OEKLCVUTIHEXNR-UHFFFAOYSA-N 0.000 claims description 2
- SRFHFBZWBFEFPO-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(3-fluorophenyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=C(F)C=CC=2)=N1 SRFHFBZWBFEFPO-UHFFFAOYSA-N 0.000 claims description 2
- MQPZMBOPZKPPQU-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(4-hydroxycyclohexyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CCC(O)CC2)=N1 MQPZMBOPZKPPQU-UHFFFAOYSA-N 0.000 claims description 2
- FKGGGBNUSFSCNO-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(thian-4-yl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CCSCC2)=N1 FKGGGBNUSFSCNO-UHFFFAOYSA-N 0.000 claims description 2
- RWWSXCPKDFWDKS-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-piperidin-4-ylurea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CCNCC2)=N1 RWWSXCPKDFWDKS-UHFFFAOYSA-N 0.000 claims description 2
- XJJTYKINXCLOPS-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-pyridin-3-ylurea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=NC=CC=2)=N1 XJJTYKINXCLOPS-UHFFFAOYSA-N 0.000 claims description 2
- RRPSERKBVVOAME-UHFFFAOYSA-N 3-[5-chloro-4-[4-(triazol-1-yl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-pyrazin-2-ylethyl)urea Chemical compound N=1C(C=2C=CC(=CC=2)N2N=NC=C2)=C(Cl)SC=1NC(=O)N(CCC=1N=CC=NC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 RRPSERKBVVOAME-UHFFFAOYSA-N 0.000 claims description 2
- HCJZARHZENLTGL-UHFFFAOYSA-N 3-[5-chloro-4-[4-(triazol-1-yl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-pyrimidin-2-ylethyl)urea Chemical compound N=1C(C=2C=CC(=CC=2)N2N=NC=C2)=C(Cl)SC=1NC(=O)N(CCC=1N=CC=CN=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 HCJZARHZENLTGL-UHFFFAOYSA-N 0.000 claims description 2
- CGHACHUTMJCHDK-UHFFFAOYSA-N 4-[2-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]ethyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1CCN(C(=O)NC=1SC(Cl)=C(N=1)C=1C=CC(NS(C)(=O)=O)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 CGHACHUTMJCHDK-UHFFFAOYSA-N 0.000 claims description 2
- ORNHVSLQFISMCN-UHFFFAOYSA-N 4-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N(C(=O)NC=1SC(Cl)=C(N=1)C=1C=CC(NS(C)(=O)=O)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 ORNHVSLQFISMCN-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229930194542 Keto Natural products 0.000 claims description 2
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 2
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- CJTRILIRUZPVAV-UHFFFAOYSA-N ethyl 2-[4-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1N(C(=O)NC=1SC(Cl)=C(N=1)C=1C=CC(NS(C)(=O)=O)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 CJTRILIRUZPVAV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- QLPCTEDVWXNZBE-UHFFFAOYSA-N methyl 2-[4-[5-chloro-2-[[3,3-diphenylpropyl(propan-2-yl)carbamoyl]amino]-1,3-thiazol-4-yl]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C(C)C)=N1 QLPCTEDVWXNZBE-UHFFFAOYSA-N 0.000 claims description 2
- YSPKIPUCRPWKRT-UHFFFAOYSA-N methyl 4-[2-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]ethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCN(C(=O)NC=1SC(Cl)=C(N=1)C=1C=CC(NS(C)(=O)=O)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 YSPKIPUCRPWKRT-UHFFFAOYSA-N 0.000 claims description 2
- RGLRYPUEVNFTPR-UHFFFAOYSA-N methyl 4-[5-chloro-2-[[3,3-diphenylpropyl(oxan-4-yl)carbamoyl]amino]-1,3-thiazol-4-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CCOCC2)=N1 RGLRYPUEVNFTPR-UHFFFAOYSA-N 0.000 claims description 2
- VENYOVUKRBBZMS-UHFFFAOYSA-N methyl 4-[[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]carbamoyl-(3,3-diphenylpropyl)amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N(C(=O)NC=1SC(Cl)=C(N=1)C=1C=CC(NS(C)(=O)=O)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 VENYOVUKRBBZMS-UHFFFAOYSA-N 0.000 claims description 2
- XWYWCGYWTAOYOV-UHFFFAOYSA-N n-[4-[2-[[3,3-bis(4-fluorophenyl)propyl-(2-pyrazin-2-ylethyl)carbamoyl]amino]-5-chloro-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=NC=2)=N1 XWYWCGYWTAOYOV-UHFFFAOYSA-N 0.000 claims description 2
- HUMZRKFFHXSTGI-UHFFFAOYSA-N n-[4-[2-[[3,3-bis(4-fluorophenyl)propyl-(2-pyrimidin-2-ylethyl)carbamoyl]amino]-5-chloro-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CN=2)=N1 HUMZRKFFHXSTGI-UHFFFAOYSA-N 0.000 claims description 2
- FPUQHHQJGMJUKS-UHFFFAOYSA-N n-[4-[5-[[3,3-bis(4-fluorophenyl)propyl-(2-pyrazin-2-ylethyl)carbamoyl]amino]-1,2,4-thiadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=NC=2)=N1 FPUQHHQJGMJUKS-UHFFFAOYSA-N 0.000 claims description 2
- ZKNRKULQAVLXAS-UHFFFAOYSA-N n-[4-[5-[[3,3-bis(4-fluorophenyl)propyl-(2-pyridin-2-ylethyl)carbamoyl]amino]-1,2,4-thiadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CC=2)=N1 ZKNRKULQAVLXAS-UHFFFAOYSA-N 0.000 claims description 2
- DNTFNMGDELJHHD-UHFFFAOYSA-N n-[4-[5-[[3,3-bis(4-fluorophenyl)propyl-(2-pyrimidin-2-ylethyl)carbamoyl]amino]-1,2,4-thiadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CN=2)=N1 DNTFNMGDELJHHD-UHFFFAOYSA-N 0.000 claims description 2
- VHCSZTCEFSMADH-UHFFFAOYSA-N n-[4-[5-[[3,3-diphenylpropyl(2-pyrazin-2-ylethyl)carbamoyl]amino]-1,2,4-thiadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=NC=2)=N1 VHCSZTCEFSMADH-UHFFFAOYSA-N 0.000 claims description 2
- OKFMWWUHBDMHPC-UHFFFAOYSA-N n-[4-[5-[[3,3-diphenylpropyl(2-pyridin-2-ylethyl)carbamoyl]amino]-1,2,4-thiadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CC=2)=N1 OKFMWWUHBDMHPC-UHFFFAOYSA-N 0.000 claims description 2
- KKALLOQOWOIRTG-UHFFFAOYSA-N n-[4-[5-[[3,3-diphenylpropyl(2-pyrimidin-2-ylethyl)carbamoyl]amino]-1,2,4-thiadiazol-3-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CN=2)=N1 KKALLOQOWOIRTG-UHFFFAOYSA-N 0.000 claims description 2
- QAOOULCDWJQMER-UHFFFAOYSA-N n-[4-[5-chloro-2-[[3,3-diphenylpropyl(2-pyrazin-2-ylethyl)carbamoyl]amino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=NC=2)=N1 QAOOULCDWJQMER-UHFFFAOYSA-N 0.000 claims description 2
- GSEMXYIDGHREQA-UHFFFAOYSA-N n-[4-[5-chloro-2-[[3,3-diphenylpropyl(2-pyridin-2-ylethyl)carbamoyl]amino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CC=2)=N1 GSEMXYIDGHREQA-UHFFFAOYSA-N 0.000 claims description 2
- ATWMXBBFIAKTAW-UHFFFAOYSA-N n-[4-[5-chloro-2-[[3,3-diphenylpropyl(2-pyrimidin-2-ylethyl)carbamoyl]amino]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CN=2)=N1 ATWMXBBFIAKTAW-UHFFFAOYSA-N 0.000 claims description 2
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- OCOTWWSGPAHHQW-UHFFFAOYSA-N trifluoro(trifluoromethylsulfinyl)methane Chemical compound FC(F)(F)S(=O)C(F)(F)F OCOTWWSGPAHHQW-UHFFFAOYSA-N 0.000 claims description 2
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- ZKOIQFRAZPGWTR-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-(2-pyrazin-2-ylethyl)-3-[3-[4-(triazol-1-yl)phenyl]-1,2,4-thiadiazol-5-yl]urea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(CCC=1N=CC=NC=1)C(=O)NC(SN=1)=NC=1C(C=C1)=CC=C1N1C=CN=N1 ZKOIQFRAZPGWTR-UHFFFAOYSA-N 0.000 claims 1
- VMPOZNQNDXYDIV-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-(2-pyridin-2-ylethyl)-3-[3-(4-sulfamoylphenyl)-1,2,4-thiadiazol-5-yl]urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CC=2)=N1 VMPOZNQNDXYDIV-UHFFFAOYSA-N 0.000 claims 1
- MRUHDUYDKMHBIR-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-propan-2-yl-3-[3-(4-sulfamoylphenyl)-1,2,4-thiadiazol-5-yl]urea Chemical compound N=1C(C=2C=CC(=CC=2)S(N)(=O)=O)=NSC=1NC(=O)N(C(C)C)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 MRUHDUYDKMHBIR-UHFFFAOYSA-N 0.000 claims 1
- AGHZLKBRHCZXRK-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[3-[4-(methanesulfonamido)phenyl]-1,2,4-thiadiazol-5-yl]-1-(2-pyridin-2-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CC=2)=N1 AGHZLKBRHCZXRK-UHFFFAOYSA-N 0.000 claims 1
- SOFOCHPFTUZMAA-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[3-[4-(methanesulfonamido)phenyl]-1,2,4-thiadiazol-5-yl]-1-(2-pyrimidin-2-ylethyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=CN=2)=N1 SOFOCHPFTUZMAA-UHFFFAOYSA-N 0.000 claims 1
- RICOTEDGEZOJHU-UHFFFAOYSA-N 1-[2-(4-chloropyridin-2-yl)ethyl]-3-[5-chloro-4-(4-sulfamoylphenyl)-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2N=CC=C(Cl)C=2)=N1 RICOTEDGEZOJHU-UHFFFAOYSA-N 0.000 claims 1
- BLGAXXUIPVJQKY-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-1-(2-pyrimidin-2-ylethyl)-3-[3-(4-sulfamoylphenyl)-1,2,4-thiadiazol-5-yl]urea Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=NSC(NC(=O)N(CCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CCC=2N=CC=CN=2)=N1 BLGAXXUIPVJQKY-UHFFFAOYSA-N 0.000 claims 1
- RXHVXKCVQOWEIQ-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)propyl]-1-(2-pyrimidin-2-ylethyl)-3-[3-[4-(triazol-1-yl)phenyl]-1,2,4-thiadiazol-5-yl]urea Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCN(C(=O)NC=1SN=C(N=1)C=1C=CC(=CC=1)N1N=NC=C1)CCC1=NC=CC=N1 RXHVXKCVQOWEIQ-UHFFFAOYSA-N 0.000 claims 1
- QVALIFYIOOJTDC-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(4-fluorophenyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC(F)=CC=2)=N1 QVALIFYIOOJTDC-UHFFFAOYSA-N 0.000 claims 1
- MAYWFBUXGLYLNU-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(oxan-4-yl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CCOCC2)=N1 MAYWFBUXGLYLNU-UHFFFAOYSA-N 0.000 claims 1
- FKJOGWVEBMXGNE-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-[2-(2-fluorophenyl)ethyl]urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2C(=CC=CC=2)F)=N1 FKJOGWVEBMXGNE-UHFFFAOYSA-N 0.000 claims 1
- YLAICAYFOQYUFU-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-[2-(2-methoxyphenyl)ethyl]urea Chemical compound COC1=CC=CC=C1CCN(C(=O)NC=1SC(Cl)=C(N=1)C=1C=CC(NS(C)(=O)=O)=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 YLAICAYFOQYUFU-UHFFFAOYSA-N 0.000 claims 1
- BVBMZBACYGKCIM-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-[2-(3-fluorophenyl)ethyl]urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC=2C=C(F)C=CC=2)=N1 BVBMZBACYGKCIM-UHFFFAOYSA-N 0.000 claims 1
- OXOMQAJDEVHIDG-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-pyridin-2-ylurea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2N=CC=CC=2)=N1 OXOMQAJDEVHIDG-UHFFFAOYSA-N 0.000 claims 1
- XVEJSVVDHUKISZ-UHFFFAOYSA-N 3-[5-chloro-4-[4-(methanesulfonamido)phenyl]-1,3-thiazol-2-yl]-1-cyclopropyl-1-(3,3-diphenylpropyl)urea Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=C(Cl)SC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C2CC2)=N1 XVEJSVVDHUKISZ-UHFFFAOYSA-N 0.000 claims 1
- DCDUXJPWYNKQJH-UHFFFAOYSA-N 3-[5-chloro-4-[4-(triazol-1-yl)phenyl]-1,3-thiazol-2-yl]-1-(3,3-diphenylprop-2-enyl)-1-(2-pyrimidin-2-ylethyl)urea Chemical compound N=1C(C=2C=CC(=CC=2)N2N=NC=C2)=C(Cl)SC=1NC(=O)N(CC=C(C=1C=CC=CC=1)C=1C=CC=CC=1)CCC1=NC=CC=N1 DCDUXJPWYNKQJH-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
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- A—HUMAN NECESSITIES
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/02—Nutrients, e.g. vitamins, minerals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D277/32—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 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Nutrition Science (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US95905807P | 2007-07-10 | 2007-07-10 | |
US60/959,058 | 2007-07-10 | ||
PCT/US2008/008508 WO2009009122A2 (fr) | 2007-07-10 | 2008-07-10 | Dérivés de l'urée et de diamines associées, leurs procédés de fabrication, et leurs utilisations |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2692598A1 true CA2692598A1 (fr) | 2009-01-15 |
Family
ID=39884677
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA 2692598 Abandoned CA2692598A1 (fr) | 2007-07-10 | 2008-07-10 | Derives de l'uree et de diamines associees, leurs procedes de fabrication, et leurs utilisations |
Country Status (6)
Country | Link |
---|---|
US (1) | US8324396B2 (fr) |
EP (1) | EP2176247A2 (fr) |
JP (1) | JP5504484B2 (fr) |
AU (1) | AU2008275595B2 (fr) |
CA (1) | CA2692598A1 (fr) |
WO (1) | WO2009009122A2 (fr) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2885129B1 (fr) * | 2005-04-29 | 2007-06-15 | Proskelia Sas | Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation. |
AU2006316705B2 (en) * | 2005-11-25 | 2011-09-29 | Galapagos Sas | Urea derivatives useful as calcium receptor modulators |
ES2499015T3 (es) * | 2007-05-08 | 2014-09-26 | Ajinomoto Co., Inc. | Agente profiláctico o terapéutico para la diarrea |
WO2013138753A1 (fr) | 2012-03-16 | 2013-09-19 | Fox Chase Chemical Diversity Center, Inc. | Promédicaments de riluzole et leur méthode d'utilisation |
CN102701992B (zh) * | 2012-07-03 | 2014-01-15 | 重庆医科大学 | 一种抗肿瘤化合物及其药学上可接受的盐、及制备方法和应用 |
CN103992236B (zh) * | 2014-04-29 | 2016-05-18 | 于非 | 一种新型靶向性抗肿瘤药物及其制备方法与应用 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58109464A (ja) | 1981-12-23 | 1983-06-29 | Nippon Paint Co Ltd | アミノ酸化合物、その製法ならびに触媒 |
IL67417A (en) * | 1982-01-26 | 1989-10-31 | American Cyanamid Co | Antiatherosclerotic substituted ureas,process for their preparation and pharmaceutical compositions containing them |
US4994465A (en) * | 1989-02-17 | 1991-02-19 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic trisubstituted urea compounds |
US5153226A (en) | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
US6031003A (en) | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
US6011068A (en) | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
JPH0841006A (ja) | 1994-08-05 | 1996-02-13 | Nisshin Flour Milling Co Ltd | ジウレア誘導体 |
CZ290670B6 (cs) | 1994-10-21 | 2002-09-11 | Nps Pharmaceuticals, Inc. | Sloučeniny modulující receptory anorganických iontů a farmaceutický prostředek, který je obsahuje |
JPH10195037A (ja) | 1996-02-15 | 1998-07-28 | Tanabe Seiyaku Co Ltd | フェノール誘導体 |
JPH11139969A (ja) | 1997-08-07 | 1999-05-25 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
US6365617B1 (en) | 1999-06-29 | 2002-04-02 | Ortho-Mcneil Pharmaceutical, Inc. | Indole and indazole urea-peptoids as thrombin receptor antagonists |
FR2820136A1 (fr) * | 2001-01-26 | 2002-08-02 | Aventis Pharma Sa | Nouveaux derives de l'uree, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation |
FR2885129B1 (fr) * | 2005-04-29 | 2007-06-15 | Proskelia Sas | Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation. |
AU2006316705B2 (en) * | 2005-11-25 | 2011-09-29 | Galapagos Sas | Urea derivatives useful as calcium receptor modulators |
GB0613674D0 (en) * | 2006-07-10 | 2006-08-16 | Proskelia Sas | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
-
2008
- 2008-07-10 JP JP2010516062A patent/JP5504484B2/ja not_active Expired - Fee Related
- 2008-07-10 WO PCT/US2008/008508 patent/WO2009009122A2/fr active Application Filing
- 2008-07-10 CA CA 2692598 patent/CA2692598A1/fr not_active Abandoned
- 2008-07-10 EP EP08780119A patent/EP2176247A2/fr not_active Withdrawn
- 2008-07-10 AU AU2008275595A patent/AU2008275595B2/en not_active Ceased
- 2008-07-10 US US12/218,228 patent/US8324396B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
AU2008275595B2 (en) | 2013-11-14 |
US8324396B2 (en) | 2012-12-04 |
JP5504484B2 (ja) | 2014-05-28 |
US20090054463A1 (en) | 2009-02-26 |
AU2008275595A1 (en) | 2009-01-15 |
WO2009009122A2 (fr) | 2009-01-15 |
EP2176247A2 (fr) | 2010-04-21 |
WO2009009122A3 (fr) | 2009-06-25 |
JP2010533185A (ja) | 2010-10-21 |
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EEER | Examination request |
Effective date: 20130627 |
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FZDE | Dead |
Effective date: 20160204 |