MXPA06001638A

MXPA06001638A - Antagonistas del receptor de la hormona concentradora de melanina.

Antagonistas del receptor de la hormona concentradora de melanina.

Info

Publication number: MXPA06001638A
Authority: MX; Mexico
Prior art keywords: group; hydrogen; alkyl; nitrogen; ethyl
Prior art date: 2003-08-13

Application number

MXPA06001638A

Other languages

English (en)

Spanish (es)

Inventor

Vu Ma

Original Assignee

Amgen Inc

Priority date

2003-08-13

Filing date

2004-08-11

Publication date

2006-04-28

2004-08-11 Application filed by Amgen Inc filed Critical Amgen Inc

2006-04-28 Publication of MXPA06001638A publication Critical patent/MXPA06001638A/es

Links

102000029828 Melanin-concentrating hormone receptor Human genes 0.000 title description 31
108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 31
229940123502 Hormone receptor antagonist Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 72
150000003839 salts Chemical class 0.000 claims abstract description 46
101800002739 Melanin-concentrating hormone Proteins 0.000 claims abstract description 23
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 23
238000011282 treatment Methods 0.000 claims abstract description 21
239000000651 prodrug Substances 0.000 claims abstract description 19
229940002612 prodrug Drugs 0.000 claims abstract description 19
230000002265 prevention Effects 0.000 claims abstract description 10
230000001404 mediated effect Effects 0.000 claims abstract description 5
102000047659 melanin-concentrating hormone Human genes 0.000 claims abstract 2
-1 aralkenyl Chemical group 0.000 claims description 1852
125000000217 alkyl group Chemical group 0.000 claims description 239
229910052739 hydrogen Inorganic materials 0.000 claims description 192
239000001257 hydrogen Substances 0.000 claims description 192
125000003118 aryl group Chemical group 0.000 claims description 171
125000000753 cycloalkyl group Chemical group 0.000 claims description 160
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 158
229910052757 nitrogen Inorganic materials 0.000 claims description 149
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 149
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 145
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 139
125000003710 aryl alkyl group Chemical group 0.000 claims description 128
125000000623 heterocyclic group Chemical group 0.000 claims description 127
229910052736 halogen Inorganic materials 0.000 claims description 115
150000002367 halogens Chemical class 0.000 claims description 114
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 113
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 104
125000003545 alkoxy group Chemical group 0.000 claims description 104
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 103
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 102
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 102
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 100
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 98
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 96
125000004104 aryloxy group Chemical group 0.000 claims description 92
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 88
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 83
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
239000004305 biphenyl Substances 0.000 claims description 80
235000010290 biphenyl Nutrition 0.000 claims description 80
125000004181 carboxyalkyl group Chemical group 0.000 claims description 78
125000001424 substituent group Chemical group 0.000 claims description 78
125000004093 cyano group Chemical group *C#N 0.000 claims description 77
125000001624 naphthyl group Chemical group 0.000 claims description 73
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 72
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 71
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 70
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 69
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 68
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 67
125000000286 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 64
125000005982 diphenylmethyl 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] 0.000 claims description 56
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 54
229910052731 fluorine Chemical group 0.000 claims description 49
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 48
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 48
239000011737 fluorine Chemical group 0.000 claims description 48
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 47
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 47
229910052794 bromium Inorganic materials 0.000 claims description 46
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 46
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 45
125000005815 pentoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 45
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 43
125000004043 oxo group Chemical group O=* 0.000 claims description 42
125000001072 heteroaryl group Chemical group 0.000 claims description 41
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 39
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 38
125000006226 butoxyethyl group Chemical group 0.000 claims description 37
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 37
125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 37
125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 37
239000000460 chlorine Chemical group 0.000 claims description 33
229910052801 chlorine Inorganic materials 0.000 claims description 33
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 31
125000003386 piperidinyl group Chemical group 0.000 claims description 29
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 27
125000001041 indolyl group Chemical group 0.000 claims description 22
125000003226 pyrazolyl group Chemical group 0.000 claims description 22
125000001544 thienyl group Chemical group 0.000 claims description 22
125000001425 triazolyl group Chemical group 0.000 claims description 22
BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 21
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 21
125000002541 furyl group Chemical group 0.000 claims description 21
125000002971 oxazolyl group Chemical group 0.000 claims description 21
125000000168 pyrrolyl group Chemical group 0.000 claims description 21
125000003831 tetrazolyl group Chemical group 0.000 claims description 20
125000002883 imidazolyl group Chemical group 0.000 claims description 19
125000001715 oxadiazolyl group Chemical group 0.000 claims description 19
125000000335 thiazolyl group Chemical group 0.000 claims description 19
208000008589 Obesity Diseases 0.000 claims description 18
125000000842 isoxazolyl group Chemical group 0.000 claims description 18
235000020824 obesity Nutrition 0.000 claims description 18
125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 17
125000001786 isothiazolyl group Chemical group 0.000 claims description 17
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 16
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 16
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 16
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 15
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 12
125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 9
239000002671 adjuvant Substances 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 8
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 8
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 8
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
125000005935 hexyloxycarbonyl group Chemical group 0.000 claims description 8
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 8
125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 7
125000001148 pentyloxycarbonyl group Chemical group 0.000 claims description 7
125000005981 pentynyl group Chemical group 0.000 claims description 7
125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 claims description 7
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 7
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
125000005888 tetrahydroindolyl group Chemical group 0.000 claims description 7
206010006550 Bulimia nervosa Diseases 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
208000030814 Eating disease Diseases 0.000 claims description 5
208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 5
235000014632 disordered eating Nutrition 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000005980 hexynyl group Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
208000032841 Bulimia Diseases 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
235000013305 food Nutrition 0.000 claims description 3
CTAPFRYPJLPFDF-UHFFFAOYSA-O hydron;1,2-oxazole Chemical compound C=1C=[NH+]OC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-O 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
208000012201 sexual and gender identity disease Diseases 0.000 claims description 3
208000015891 sexual disease Diseases 0.000 claims description 3
208000019116 sleep disease Diseases 0.000 claims description 3
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
206010008111 Cerebral haemorrhage Diseases 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
230000001850 reproductive effect Effects 0.000 claims description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 16
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 14
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 8
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 claims 2
125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
ZPPXWZDJDIOJFP-UHFFFAOYSA-N 1,3-dihydroisoindole-2-carboxylic acid Chemical compound C1=CC=C2CN(C(=O)O)CC2=C1 ZPPXWZDJDIOJFP-UHFFFAOYSA-N 0.000 claims 1
NOJVDSZMTUASRT-UHFFFAOYSA-N 1-[2-(3,4-dimethylphenoxy)-5-(2-methyl-2-pyrrolidin-1-ylpyrrolidine-1-carbonyl)phenyl]-3-phenylurea Chemical compound C1=C(C)C(C)=CC=C1OC1=CC=C(C(=O)N2C(CCC2)(C)N2CCCC2)C=C1NC(=O)NC1=CC=CC=C1 NOJVDSZMTUASRT-UHFFFAOYSA-N 0.000 claims 1
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
LMJDWRWZTXQWTI-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-indole Chemical group C1CCC=C2NCCC21 LMJDWRWZTXQWTI-UHFFFAOYSA-N 0.000 claims 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 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
NXLQWOFWVPUYTQ-UHFFFAOYSA-N 3-[(2-chlorophenyl)carbamoylamino]-4-(3,4-dimethylphenoxy)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=C(C)C(C)=CC=C1OC1=CC=C(C(=O)NCCN2CCCC2)C=C1NC(=O)NC1=CC=CC=C1Cl NXLQWOFWVPUYTQ-UHFFFAOYSA-N 0.000 claims 1
HGHCTHIUUMCMGT-UHFFFAOYSA-N 3-[(3,5-dichlorophenyl)carbamoylamino]-4-(3,4-dimethylphenoxy)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=C(C)C(C)=CC=C1OC1=CC=C(C(=O)NCCN2CCCC2)C=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 HGHCTHIUUMCMGT-UHFFFAOYSA-N 0.000 claims 1
MRTUQOOKMVPGAR-UHFFFAOYSA-N 3-[(3-fluorophenyl)carbamoylamino]-4-phenoxy-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound FC1=CC=CC(NC(=O)NC=2C(=CC=C(C=2)C(=O)NCCN2CCCC2)OC=2C=CC=CC=2)=C1 MRTUQOOKMVPGAR-UHFFFAOYSA-N 0.000 claims 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
NOHYKQAGOKRKCR-UHFFFAOYSA-N 4-(3,4-dimethylphenoxy)-3-[(4-phenylphenyl)carbamoylamino]-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound C1=C(C)C(C)=CC=C1OC1=CC=C(C(=O)NCCN2CCCC2)C=C1NC(=O)NC1=CC=C(C=2C=CC=CC=2)C=C1 NOHYKQAGOKRKCR-UHFFFAOYSA-N 0.000 claims 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
RSHDIRFXFZZNNO-UHFFFAOYSA-N COClOC1=CC=CC=C1 Chemical compound COClOC1=CC=CC=C1 RSHDIRFXFZZNNO-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
206010010904 Convulsion Diseases 0.000 claims 1
SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical group O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 claims 1
NWWZMYOLXGROHZ-UHFFFAOYSA-N OCl(OCCC)(OCC)OC Chemical group OCl(OCCC)(OCC)OC NWWZMYOLXGROHZ-UHFFFAOYSA-N 0.000 claims 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical group BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
NYRXUFQAPFKBTJ-UHFFFAOYSA-N n-[2-(3,4-dimethylphenoxy)-5-(2-pyrrolidin-1-ylethylcarbamoyl)phenyl]naphthalene-2-carboxamide Chemical compound C1=C(C)C(C)=CC=C1OC1=CC=C(C(=O)NCCN2CCCC2)C=C1NC(=O)C1=CC=C(C=CC=C2)C2=C1 NYRXUFQAPFKBTJ-UHFFFAOYSA-N 0.000 claims 1
MWVPQZRIWVPJCA-UHFFFAOYSA-N propylcyclopropane Chemical compound CCCC1CC1 MWVPQZRIWVPJCA-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 abstract description 24
150000003254 radicals Chemical class 0.000 description 60
150000002431 hydrogen Chemical class 0.000 description 45
125000004432 carbon atom Chemical group C* 0.000 description 33
102400001132 Melanin-concentrating hormone Human genes 0.000 description 21
235000002639 sodium chloride Nutrition 0.000 description 21
102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 14
108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 14
229940044551 receptor antagonist Drugs 0.000 description 13
239000002464 receptor antagonist Substances 0.000 description 13
206010033307 Overweight Diseases 0.000 description 11
239000000203 mixture Substances 0.000 description 10
125000004433 nitrogen atom Chemical group N* 0.000 description 10
102000005962 receptors Human genes 0.000 description 10
108020003175 receptors Proteins 0.000 description 10
230000027455 binding Effects 0.000 description 9
125000004434 sulfur atom Chemical group 0.000 description 9
239000002253 acid Substances 0.000 description 8
125000004430 oxygen atom Chemical group O* 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
150000005840 aryl radicals Chemical class 0.000 description 6
230000037396 body weight Effects 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
101150104680 MCH1 gene Proteins 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
101100382379 Rattus norvegicus Cap1 gene Proteins 0.000 description 5
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