CA2509042A1 - Novel mch receptor antagonists - Google Patents

Info

Publication number

CA2509042A1

CA2509042A1 CA002509042A CA2509042A CA2509042A1 CA 2509042 A1 CA2509042 A1 CA 2509042A1 CA 002509042 A CA002509042 A CA 002509042A CA 2509042 A CA2509042 A CA 2509042A CA 2509042 A1 CA2509042 A1 CA 2509042A1

Authority

CA

Canada

Prior art keywords

biphenyl

carboxylic acid

ethylsulfanylmethyl

phenoxy

dimethylamino

Prior art date

2002-12-11

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 102000029828 Melanin-concentrating hormone receptor Human genes 0.000 title description 15
• 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 15
• 229940044551 receptor antagonist Drugs 0.000 title description 2
• 239000002464 receptor antagonist Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 163
• 239000000203 mixture Substances 0.000 claims abstract description 65
• 101800002739 Melanin-concentrating hormone Proteins 0.000 claims abstract description 31
• ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 claims abstract description 31
• 208000008589 Obesity Diseases 0.000 claims abstract description 25
• 235000020824 obesity Nutrition 0.000 claims abstract description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
• 150000003839 salts Chemical class 0.000 claims abstract description 19
• 201000010099 disease Diseases 0.000 claims abstract description 17
• 238000011282 treatment Methods 0.000 claims abstract description 14
• 208000024891 symptom Diseases 0.000 claims abstract description 6
• 239000012453 solvate Substances 0.000 claims abstract description 5
• 102000047659 melanin-concentrating hormone Human genes 0.000 claims abstract 2
• -1 nitro, cyano, amino Chemical group 0.000 claims description 82
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• 238000000034 method Methods 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
• 125000003118 aryl group Chemical group 0.000 claims description 56
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 43
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 36
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 27
• 229910052717 sulfur Chemical group 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 23
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
• 125000005647 linker group Chemical group 0.000 claims description 18
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000004429 atom Chemical group 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 150000003891 oxalate salts Chemical class 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000001188 haloalkyl group Chemical group 0.000 claims description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
• 239000001301 oxygen Chemical group 0.000 claims description 8
• 239000011593 sulfur Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 208000035475 disorder Diseases 0.000 claims description 5
• WUPJWBCAEKWGDY-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 WUPJWBCAEKWGDY-UHFFFAOYSA-N 0.000 claims description 5
• LQOXGXQUSLMUTL-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 LQOXGXQUSLMUTL-UHFFFAOYSA-N 0.000 claims description 5
• JUSRMRJMSMPGEH-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound C1=CC(C(=O)NCCCN(C)C)=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 JUSRMRJMSMPGEH-UHFFFAOYSA-N 0.000 claims description 5
• 125000004043 oxo group Chemical group O=* 0.000 claims description 5
• 239000000651 prodrug Substances 0.000 claims description 5
• 229940002612 prodrug Drugs 0.000 claims description 5
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 4
• 208000025865 Ulcer Diseases 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 239000012634 fragment Substances 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• LNNOETJTMSDLFY-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCNC(=O)C1=CC=CC(C=2C(=CC=CC=2)CSCCOC=2C=CC=CC=2)=C1 LNNOETJTMSDLFY-UHFFFAOYSA-N 0.000 claims description 4
• GDKCWCCQFVKUNK-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(C(=O)NCCN(C)C)=CC=C1C(C=C1)=CC=C1CSCCOC1=CC=CC=C1 GDKCWCCQFVKUNK-UHFFFAOYSA-N 0.000 claims description 4
• GLNGDYFLXUBPNG-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC=C1C1=CC=CC(CSCCOC=2C=CC=CC=2)=C1 GLNGDYFLXUBPNG-UHFFFAOYSA-N 0.000 claims description 4
• DZPPHBRORYQXPB-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCNC(=O)C1=CC=CC(C=2C(=CC=CC=2)CSCCOC=2C=CC=CC=2)=C1 DZPPHBRORYQXPB-UHFFFAOYSA-N 0.000 claims description 4
• RWPAKUXYZGBFON-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCNC(=O)C1=CC=CC(C=2C=C(CSCCOC=3C=CC=CC=3)C=CC=2)=C1 RWPAKUXYZGBFON-UHFFFAOYSA-N 0.000 claims description 4
• AXCTUCCJQSBVCN-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(C(=O)NCCCN(C)C)=CC=C1C1=CC=CC(CSCCOC=2C=CC=CC=2)=C1 AXCTUCCJQSBVCN-UHFFFAOYSA-N 0.000 claims description 4
• DZMFIABOJLTCQP-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)NCCCN(C)C)=CC=C1C(C=C1)=CC=C1CSCCOC1=CC=CC=C1 DZMFIABOJLTCQP-UHFFFAOYSA-N 0.000 claims description 4
• FAOPHDMSPRHRBA-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-2-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCCNC(=O)C1=CC=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 FAOPHDMSPRHRBA-UHFFFAOYSA-N 0.000 claims description 4
• JCIWUZSRYDHNJP-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-4-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound C1=CC(C(=O)NCCCCN(C)C)=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 JCIWUZSRYDHNJP-UHFFFAOYSA-N 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 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 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 230000004064 dysfunction Effects 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 201000001421 hyperglycemia Diseases 0.000 claims description 3
• 125000001620 monocyclic carbocycle group Chemical group 0.000 claims description 3
• QDTQUWYRAOYVJL-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCNC(=O)C1=CC=CC=C1C1=CC=CC=C1CSCCOC1=CC=CC=C1 QDTQUWYRAOYVJL-UHFFFAOYSA-N 0.000 claims description 3
• DKSIJMRGMKTNBR-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCNC(=O)C1=CC=CC=C1C(C=C1)=CC=C1CSCCOC1=CC=CC=C1 DKSIJMRGMKTNBR-UHFFFAOYSA-N 0.000 claims description 3
• DLMBMQNMBCWDEE-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=CC=CC(CSCCOC=2C=CC=CC=2)=C1 DLMBMQNMBCWDEE-UHFFFAOYSA-N 0.000 claims description 3
• GHLHQSQJFBZQKJ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=CC=C1C(C=C1)=CC=C1CSCCOC1=CC=CC=C1 GHLHQSQJFBZQKJ-UHFFFAOYSA-N 0.000 claims description 3
• QDQOPHHTRAASDF-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-2-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide Chemical compound CN(C)CCCCNC(=O)C1=CC=CC=C1C1=CC=CC(CSCCOC=2C=CC=CC=2)=C1 QDQOPHHTRAASDF-UHFFFAOYSA-N 0.000 claims description 3
• MZVJGKABDKHPPE-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-2-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCCNC(=O)C1=CC=CC=C1C(C=C1)=CC=C1CSCCOC1=CC=CC=C1 MZVJGKABDKHPPE-UHFFFAOYSA-N 0.000 claims description 3
• ZCWRVBROAACMAC-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-3-[2-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCCNC(=O)C1=CC=CC(C=2C(=CC=CC=2)CSCCOC=2C=CC=CC=2)=C1 ZCWRVBROAACMAC-UHFFFAOYSA-N 0.000 claims description 3
• NHKIIMBGHFZVTB-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-3-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)CCCCNC(=O)C1=CC=CC(C=2C=CC(CSCCOC=3C=CC=CC=3)=CC=2)=C1 NHKIIMBGHFZVTB-UHFFFAOYSA-N 0.000 claims description 3
• DMCRKRFTAIJUNA-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-4-[3-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(C(=O)NCCCCN(C)C)=CC=C1C1=CC=CC(CSCCOC=2C=CC=CC=2)=C1 DMCRKRFTAIJUNA-UHFFFAOYSA-N 0.000 claims description 3
• OGPHAGKFDHGOLT-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-4-[4-(2-phenoxyethylsulfanylmethyl)phenyl]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(C(=O)NCCCCN(C)C)=CC=C1C(C=C1)=CC=C1CSCCOC1=CC=CC=C1 OGPHAGKFDHGOLT-UHFFFAOYSA-N 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
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• 238000006467 substitution reaction Methods 0.000 claims description 3
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• 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 2
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• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
• 125000005518 carboxamido group Chemical group 0.000 claims description 2
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• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical class OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
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• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
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• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
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