JP2007502862A5 - - Google Patents
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- Publication number
- JP2007502862A5 JP2007502862A5 JP2006532796A JP2006532796A JP2007502862A5 JP 2007502862 A5 JP2007502862 A5 JP 2007502862A5 JP 2006532796 A JP2006532796 A JP 2006532796A JP 2006532796 A JP2006532796 A JP 2006532796A JP 2007502862 A5 JP2007502862 A5 JP 2007502862A5
- Authority
- JP
- Japan
- Prior art keywords
- biphenyl
- amino
- carbonyl
- trans
- carboxylic acid
- 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.)
- Granted
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 66
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 18
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 18
- 125000001475 halogen functional group Chemical group 0.000 claims 18
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 13
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 13
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 10
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 9
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 9
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 239000003112 inhibitor Substances 0.000 claims 7
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- -1 4 ′-{[6- (trifluoromethoxy) -1,3-benzothiazol-2-yl] amino} -1,1′-biphenyl-4-yl Chemical group 0.000 claims 5
- 208000008589 Obesity Diseases 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 235000020824 obesity Nutrition 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 239000005973 Carvone Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 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 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 2
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 102000002808 Pituitary adenylate cyclase-activating polypeptide Human genes 0.000 claims 2
- 108010004684 Pituitary adenylate cyclase-activating polypeptide Proteins 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- OWMZNFCDEHGFEP-NFBCVYDUSA-N secretin human Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(N)=O)[C@@H](C)O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)C1=CC=CC=C1 OWMZNFCDEHGFEP-NFBCVYDUSA-N 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- IOQRTGZPCYYQLE-RTBURBONSA-N (1r,2r)-2-[4-[3-fluoro-4-[(6-fluoro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=C(F)C(NC=3SC4=CC(F)=CC=C4N=3)=CC=2)C=C1 IOQRTGZPCYYQLE-RTBURBONSA-N 0.000 claims 1
- VFKRRRPFLRUITM-WOJBJXKFSA-N (1r,2r)-2-[4-[3-fluoro-4-[(6-methoxy-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(C(=C1)F)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O VFKRRRPFLRUITM-WOJBJXKFSA-N 0.000 claims 1
- SQDFXCQUZPRWQC-QZTJIDSGSA-N (1r,2r)-2-[4-[3-fluoro-4-[(6-methoxy-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopropane-1-carboxylic acid Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(C(=C1)F)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1C[C@H]1C(O)=O SQDFXCQUZPRWQC-QZTJIDSGSA-N 0.000 claims 1
- WOQFPHQYISJISP-WOJBJXKFSA-N (1r,2r)-2-[4-[3-fluoro-4-[(6-methoxy-1,3-benzoxazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound O1C2=CC(OC)=CC=C2N=C1NC(C(=C1)F)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O WOQFPHQYISJISP-WOJBJXKFSA-N 0.000 claims 1
- WJLWQLZDOUBIRZ-QZTJIDSGSA-N (1r,2r)-2-[4-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenyl]benzoyl]cyclobutane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CC[C@H]1C(=O)C1=CC=C(C=2C=C(F)C(NC=3SC4=CC=CC=C4N=3)=CC=2)C=C1 WJLWQLZDOUBIRZ-QZTJIDSGSA-N 0.000 claims 1
- FSKCTGQMFDNLOF-RTBURBONSA-N (1r,2r)-2-[4-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=C(F)C(NC=3SC4=CC=CC=C4N=3)=CC=2)C=C1 FSKCTGQMFDNLOF-RTBURBONSA-N 0.000 claims 1
- HQYZCXUDFYUJCE-IAGOWNOFSA-N (1r,2r)-2-[4-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenyl]benzoyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H]1C(=O)C1=CC=C(C=2C=C(F)C(NC=3SC4=CC=CC=C4N=3)=CC=2)C=C1 HQYZCXUDFYUJCE-IAGOWNOFSA-N 0.000 claims 1
- GTTCDQBVIYYEQE-NHCUHLMSSA-N (1r,2r)-2-[4-[4-(1,3-benzothiazol-2-ylamino)phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=C1 GTTCDQBVIYYEQE-NHCUHLMSSA-N 0.000 claims 1
- JJAALGMOWHXNSJ-RTBURBONSA-N (1r,2r)-2-[4-[4-(1,3-benzothiazol-2-ylamino)phenyl]benzoyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=C1 JJAALGMOWHXNSJ-RTBURBONSA-N 0.000 claims 1
- RPPAOAPFKYSPEC-NHCUHLMSSA-N (1r,2r)-2-[4-[4-(1,3-benzoxazol-2-ylamino)phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3OC4=CC=CC=C4N=3)=CC=2)C=C1 RPPAOAPFKYSPEC-NHCUHLMSSA-N 0.000 claims 1
- JBRHHXXUUWWMLT-NHCUHLMSSA-N (1r,2r)-2-[4-[4-(1h-benzimidazol-2-ylamino)phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3NC4=CC=CC=C4N=3)=CC=2)C=C1 JBRHHXXUUWWMLT-NHCUHLMSSA-N 0.000 claims 1
- MQTBNDWDKDXDBV-WOJBJXKFSA-N (1r,2r)-2-[4-[4-[(4,6-difluoro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=CC(F)=CC(F)=C4N=3)=CC=2)C=C1 MQTBNDWDKDXDBV-WOJBJXKFSA-N 0.000 claims 1
- ZGRIRSYJGHEZPA-QZTJIDSGSA-N (1r,2r)-2-[4-[4-[(4,6-difluoro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=CC(F)=CC(F)=C4N=3)=CC=2)C=C1 ZGRIRSYJGHEZPA-QZTJIDSGSA-N 0.000 claims 1
- VNLWMJOYGWNDIP-WOJBJXKFSA-N (1r,2r)-2-[4-[4-[(4-chloro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=CC=CC(Cl)=C4N=3)=CC=2)C=C1 VNLWMJOYGWNDIP-WOJBJXKFSA-N 0.000 claims 1
- NOCDQRXRFAZSHH-NHCUHLMSSA-N (1r,2r)-2-[4-[4-[(4-methyl-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclobutane-1-carboxylic acid Chemical compound N=1C=2C(C)=CC=CC=2SC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CC[C@H]1C(O)=O NOCDQRXRFAZSHH-NHCUHLMSSA-N 0.000 claims 1
- QHIDAFDPLFSCAT-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(4-methyl-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound N=1C=2C(C)=CC=CC=2SC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O QHIDAFDPLFSCAT-FGZHOGPDSA-N 0.000 claims 1
- KFIDSUWBKWEUPD-WOJBJXKFSA-N (1r,2r)-2-[4-[4-[(4-methyl-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopropane-1-carboxylic acid Chemical compound N=1C=2C(C)=CC=CC=2SC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1C[C@H]1C(O)=O KFIDSUWBKWEUPD-WOJBJXKFSA-N 0.000 claims 1
- VZOWCNYXALKHKB-RTBURBONSA-N (1r,2r)-2-[4-[4-[(5,6-difluoro-1h-benzimidazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3NC4=CC(F)=C(F)C=C4N=3)=CC=2)C=C1 VZOWCNYXALKHKB-RTBURBONSA-N 0.000 claims 1
- NXEXOGHUXKSPKY-DHIUTWEWSA-N (1r,2r)-2-[4-[4-[(5,6-dimethyl-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound S1C=2C=C(C)C(C)=CC=2N=C1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O NXEXOGHUXKSPKY-DHIUTWEWSA-N 0.000 claims 1
- XTKPQNRIOJAORW-DHIUTWEWSA-N (1r,2r)-2-[4-[4-[(5,6-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound O1C=2C=C(C)C(C)=CC=2N=C1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O XTKPQNRIOJAORW-DHIUTWEWSA-N 0.000 claims 1
- IKJTYZKQVKNTNB-WOJBJXKFSA-N (1r,2r)-2-[4-[4-[(5,7-difluoro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=C(F)C=C(F)C=C4N=3)=CC=2)C=C1 IKJTYZKQVKNTNB-WOJBJXKFSA-N 0.000 claims 1
- GVIVCRISHRFJKX-QZTJIDSGSA-N (1r,2r)-2-[4-[4-[(5,7-difluoro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=C(F)C=C(F)C=C4N=3)=CC=2)C=C1 GVIVCRISHRFJKX-QZTJIDSGSA-N 0.000 claims 1
- RZUFJINKBGSBBW-DHIUTWEWSA-N (1r,2r)-2-[4-[4-[(5,7-dimethyl-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound N=1C2=CC(C)=CC(C)=C2SC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O RZUFJINKBGSBBW-DHIUTWEWSA-N 0.000 claims 1
- DGFABCQJVANUGA-NHCUHLMSSA-N (1r,2r)-2-[4-[4-[(5-chloro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=CC=C(Cl)C=C4N=3)=CC=2)C=C1 DGFABCQJVANUGA-NHCUHLMSSA-N 0.000 claims 1
- LWYIEOHYIIESJR-NHCUHLMSSA-N (1r,2r)-2-[4-[4-[(5-fluoro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=CC=C(F)C=C4N=3)=CC=2)C=C1 LWYIEOHYIIESJR-NHCUHLMSSA-N 0.000 claims 1
- HYDYRAMHCBQLFV-NHCUHLMSSA-N (1r,2r)-2-[4-[4-[(5-fluoro-1,3-benzoxazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3OC4=CC=C(F)C=C4N=3)=CC=2)C=C1 HYDYRAMHCBQLFV-NHCUHLMSSA-N 0.000 claims 1
- NIZGAMFZQQGTRM-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(5-methoxy-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound N=1C2=CC(OC)=CC=C2SC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O NIZGAMFZQQGTRM-FGZHOGPDSA-N 0.000 claims 1
- AOHBCGJOPIUWAT-DHIUTWEWSA-N (1r,2r)-2-[4-[4-[(5-methyl-1,3-benzoxazol-2-yl)amino]phenyl]benzoyl]cyclohexane-1-carboxylic acid Chemical compound N=1C2=CC(C)=CC=C2OC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCCC[C@H]1C(O)=O AOHBCGJOPIUWAT-DHIUTWEWSA-N 0.000 claims 1
- YOZJJRCGKFYMSR-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(5-methyl-1,3-benzoxazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound N=1C2=CC(C)=CC=C2OC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O YOZJJRCGKFYMSR-FGZHOGPDSA-N 0.000 claims 1
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- FFYOCPKBOVVSFL-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(6-methoxy-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O FFYOCPKBOVVSFL-FGZHOGPDSA-N 0.000 claims 1
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- FGBHNUUKYHCJGA-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(6-methoxy-1,3-benzoxazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound O1C2=CC(OC)=CC=C2N=C1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O FGBHNUUKYHCJGA-FGZHOGPDSA-N 0.000 claims 1
- KEHDTQPEHDUAIZ-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(6-methoxy-1h-benzimidazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound N=1C2=CC(OC)=CC=C2NC=1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O KEHDTQPEHDUAIZ-FGZHOGPDSA-N 0.000 claims 1
- ZZAMTZZJQQNKLK-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(6-methyl-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound S1C2=CC(C)=CC=C2N=C1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O ZZAMTZZJQQNKLK-FGZHOGPDSA-N 0.000 claims 1
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- BGLXNMBFRDEJQI-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(6-methyl-1,3-benzoxazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound O1C2=CC(C)=CC=C2N=C1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O BGLXNMBFRDEJQI-FGZHOGPDSA-N 0.000 claims 1
- ZBULGTQMIIYDPZ-FGZHOGPDSA-N (1r,2r)-2-[4-[4-[(6-methylsulfonyl-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound S1C2=CC(S(=O)(=O)C)=CC=C2N=C1NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)[C@@H]1CCC[C@H]1C(O)=O ZBULGTQMIIYDPZ-FGZHOGPDSA-N 0.000 claims 1
- SIDPBRCBTHAQJA-NHCUHLMSSA-N (1r,2r)-2-[4-[4-[(6-nitro-1,3-benzothiazol-2-yl)amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3SC4=CC(=CC=C4N=3)[N+]([O-])=O)=CC=2)C=C1 SIDPBRCBTHAQJA-NHCUHLMSSA-N 0.000 claims 1
- ITUCWJIAHUMBNZ-NHCUHLMSSA-N (1r,2r)-2-[4-[4-[[6-(trifluoromethyl)-1h-benzimidazol-2-yl]amino]phenyl]benzoyl]cyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(=O)C1=CC=C(C=2C=CC(NC=3NC4=CC=C(C=C4N=3)C(F)(F)F)=CC=2)C=C1 ITUCWJIAHUMBNZ-NHCUHLMSSA-N 0.000 claims 1
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 1
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 claims 1
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- SVSZGEFXGDXMRA-UHFFFAOYSA-N 4-[4-[4-[(6-chloro-1,3-benzothiazol-2-yl)amino]-3-fluorophenyl]phenyl]-4-oxo-2-(2-phenylethyl)butanoic acid Chemical compound C=1C=C(C=2C=C(F)C(NC=3SC4=CC(Cl)=CC=C4N=3)=CC=2)C=CC=1C(=O)CC(C(=O)O)CCC1=CC=CC=C1 SVSZGEFXGDXMRA-UHFFFAOYSA-N 0.000 claims 1
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- PDPGARTYIRCWIG-UHFFFAOYSA-N 4-[4-[4-[(6-chloro-1,3-benzothiazol-2-yl)amino]phenyl]phenyl]-2-[2-(dimethylamino)ethyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CC(CCN(C)C)C(O)=O)=CC=C1C(C=C1)=CC=C1NC1=NC2=CC=C(Cl)C=C2S1 PDPGARTYIRCWIG-UHFFFAOYSA-N 0.000 claims 1
- NDIPRIOGQSLBQK-UHFFFAOYSA-N 4-[4-[4-[(6-chloro-1,3-benzothiazol-2-yl)amino]phenyl]phenyl]-4-oxo-2-(2-phenylethyl)butanoic acid Chemical compound C=1C=C(C=2C=CC(NC=3SC4=CC(Cl)=CC=C4N=3)=CC=2)C=CC=1C(=O)CC(C(=O)O)CCC1=CC=CC=C1 NDIPRIOGQSLBQK-UHFFFAOYSA-N 0.000 claims 1
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- JAYLBCKQXIUQIB-UHFFFAOYSA-N 4-[4-[4-[(6-ethoxy-1,3-benzothiazol-2-yl)amino]phenyl]phenyl]-2,2-dimethyl-4-oxobutanoic acid Chemical compound S1C2=CC(OCC)=CC=C2N=C1NC(C=C1)=CC=C1C1=CC=C(C(=O)CC(C)(C)C(O)=O)C=C1 JAYLBCKQXIUQIB-UHFFFAOYSA-N 0.000 claims 1
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| EP4039676A4 (en) * | 2019-10-02 | 2024-04-03 | Klotho Sciences | COMPOUND FOR INDUCING THE EXPRESSION OF AN ANTI-AGEING GENE KLOTHO AND USE THEREOF |
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| DE2112840A1 (de) | 1971-03-17 | 1972-10-05 | Thomae Gmbh Dr K | Neue 4-(4-Biphenylyl)-buttersaeuren,ihre Salze und Ester |
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| US3997589A (en) * | 1971-03-17 | 1976-12-14 | Boehringer Ingelheim Gmbh | 4-(2'-Fluoro-4-biphenylylr-4-oxo-butyric acid and esters and salts thereof |
| DE2112716A1 (de) | 1971-03-17 | 1972-10-05 | Thomae Gmbh Dr K | Neue 4-(4-Biphenylyl)-4-oxobuttersaeuren,ihre Salze und ihre Ester |
| DE2112715A1 (de) | 1971-03-17 | 1972-10-05 | Thomae Gmbh Dr K | Neue 4-(4-Biphenylyl)-4-hydroxybuttersaeuren,ihre Salze,Ester und Lactone |
| US4021479A (en) * | 1971-03-17 | 1977-05-03 | Boehringer Ingelheim Gmbh | Derivatives of 4-(4-biphenylyl)-butyric acid |
| DE3825617C2 (de) | 1988-07-28 | 1993-11-18 | W D Schumacher | Einrichtung zur Entfernung von Schmutz oder anderen Verunreinigungen |
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2004
- 2004-04-30 AR ARP040101491A patent/AR044152A1/es unknown
- 2004-05-06 JP JP2006532796A patent/JP4759517B2/ja not_active Expired - Fee Related
- 2004-05-06 ES ES04751430T patent/ES2369220T3/es not_active Expired - Lifetime
- 2004-05-06 CA CA002524470A patent/CA2524470A1/en not_active Abandoned
- 2004-05-06 CN CNA2004800191925A patent/CN1816531A/zh active Pending
- 2004-05-06 AU AU2004238258A patent/AU2004238258A1/en not_active Abandoned
- 2004-05-06 MX MXPA05012061A patent/MXPA05012061A/es unknown
- 2004-05-06 AT AT04751430T patent/ATE518841T1/de not_active IP Right Cessation
- 2004-05-06 EP EP04751430A patent/EP1633722B1/en not_active Expired - Lifetime
- 2004-05-06 US US10/839,833 patent/US7091228B2/en not_active Expired - Fee Related
- 2004-05-06 CL CL200400969A patent/CL2004000969A1/es unknown
- 2004-05-06 KR KR1020057021232A patent/KR20060009916A/ko not_active Ceased
- 2004-05-06 RU RU2005138134/04A patent/RU2357959C2/ru not_active IP Right Cessation
- 2004-05-06 NZ NZ543993A patent/NZ543993A/en unknown
- 2004-05-06 WO PCT/US2004/014036 patent/WO2004100881A2/en not_active Ceased
- 2004-05-06 BR BRPI0410170-7A patent/BRPI0410170A/pt not_active IP Right Cessation
- 2004-05-07 UY UY28314A patent/UY28314A1/es not_active Application Discontinuation
- 2004-05-07 PE PE2004000471A patent/PE20050265A1/es not_active Application Discontinuation
- 2004-05-07 GT GT200400092A patent/GT200400092A/es unknown
- 2004-05-07 TW TW093112839A patent/TW200510334A/zh unknown
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2005
- 2005-11-24 MA MA28625A patent/MA27843A1/fr unknown
- 2005-12-06 ZA ZA200509883A patent/ZA200509883B/en unknown
- 2005-12-08 NO NO20055832A patent/NO20055832L/no not_active Application Discontinuation
- 2005-12-09 EC EC2005006210A patent/ECSP056210A/es unknown
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2006
- 2006-01-27 US US11/341,197 patent/US7423156B2/en not_active Expired - Fee Related
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2008
- 2008-08-04 US US12/185,813 patent/US20090197795A1/en not_active Abandoned
- 2008-09-05 US US12/231,878 patent/US8013166B2/en not_active Expired - Fee Related
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