HRP20050179A2 - Novel carboxamide compounds having an mch-antagonistic effect, medicaments containing said compounds, and methods for the production thereof - Google Patents
Novel carboxamide compounds having an mch-antagonistic effect, medicaments containing said compounds, and methods for the production thereof Download PDFInfo
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- HRP20050179A2 HRP20050179A2 HR20050179A HRP20050179A HRP20050179A2 HR P20050179 A2 HRP20050179 A2 HR P20050179A2 HR 20050179 A HR20050179 A HR 20050179A HR P20050179 A HRP20050179 A HR P20050179A HR P20050179 A2 HRP20050179 A2 HR P20050179A2
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- Prior art keywords
- phenyl
- alkyl
- ethyl
- ylmethyl
- group
- Prior art date
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- -1 carboxamide compounds Chemical class 0.000 title claims abstract description 288
- 238000000034 method Methods 0.000 title claims abstract description 88
- 150000001875 compounds Chemical class 0.000 title claims description 104
- 239000003814 drug Substances 0.000 title abstract description 16
- 230000000694 effects Effects 0.000 title abstract description 10
- 238000004519 manufacturing process Methods 0.000 title description 13
- 238000011282 treatment Methods 0.000 claims abstract description 59
- 208000008589 Obesity Diseases 0.000 claims abstract description 39
- 235000020824 obesity Nutrition 0.000 claims abstract description 39
- 229910052796 boron Inorganic materials 0.000 claims abstract description 31
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 31
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 17
- 206010061428 decreased appetite Diseases 0.000 claims abstract description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 8
- 208000032841 Bulimia Diseases 0.000 claims abstract description 7
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims abstract description 7
- 208000022531 anorexia Diseases 0.000 claims abstract description 6
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 6
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 6
- 208000030814 Eating disease Diseases 0.000 claims abstract description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 5
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 5
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 5
- 206010020710 Hyperphagia Diseases 0.000 claims abstract description 4
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 116
- 239000002904 solvent Substances 0.000 claims description 100
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 88
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 70
- 239000013543 active substance Substances 0.000 claims description 52
- 125000004122 cyclic group Chemical group 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 50
- VBYIYDQHYIBKLT-UHFFFAOYSA-N 2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1CN1CCCC1 VBYIYDQHYIBKLT-UHFFFAOYSA-N 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 30
- 229920006395 saturated elastomer Polymers 0.000 claims description 29
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- FIMRRWLTRBEAOM-UHFFFAOYSA-N 4-(4-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1 FIMRRWLTRBEAOM-UHFFFAOYSA-N 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
- 239000005557 antagonist Substances 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 230000037396 body weight Effects 0.000 claims description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 230000002265 prevention Effects 0.000 claims description 16
- 239000012317 TBTU Substances 0.000 claims description 15
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 12
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 10
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 10
- 206010003246 arthritis Diseases 0.000 claims description 10
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical class C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 7
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 7
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 6
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 6
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 6
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 6
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 208000002249 Diabetes Complications Diseases 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 5
- UHBKRBDMZUQJBZ-UHFFFAOYSA-N 3-[2-[4-(3-azaspiro[5.5]undecan-3-ylmethyl)phenyl]ethyl]-7-(4-chlorophenyl)-1,2,3-benzotriazin-4-one Chemical compound C1=CC(Cl)=CC=C1C1=CC=C2C(=O)N(CCC=3C=CC(CN4CCC5(CCCCC5)CC4)=CC=3)N=NC2=C1 UHBKRBDMZUQJBZ-UHFFFAOYSA-N 0.000 claims description 5
- SXWGICMJWIPPTI-UHFFFAOYSA-N 4-(4-bromophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)C=C1 SXWGICMJWIPPTI-UHFFFAOYSA-N 0.000 claims description 5
- WLOGMDLGOQTBOB-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[2-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C=1C=C(CCNC(=O)C=2C=CC(=CC=2)C=2C=CC(Cl)=CC=2)C(F)=CC=1CN1CCCC1 WLOGMDLGOQTBOB-UHFFFAOYSA-N 0.000 claims description 5
- XNXMRTHXJJWSOI-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[3-methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C=1C=C(CN2CCCC2)C(OC)=CC=1CCNC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 XNXMRTHXJJWSOI-UHFFFAOYSA-N 0.000 claims description 5
- YLAZAKIYXJWIJT-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)cyclohexyl]ethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)NCCC2CCC(CN3CCCC3)CC2)C=C1 YLAZAKIYXJWIJT-UHFFFAOYSA-N 0.000 claims description 5
- XTLAJCBQIWYEEK-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]-3,6-dihydro-2h-pyridine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CCN(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)CC1 XTLAJCBQIWYEEK-UHFFFAOYSA-N 0.000 claims description 5
- HAKKERAGHOXDDR-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)C=C1 HAKKERAGHOXDDR-UHFFFAOYSA-N 0.000 claims description 5
- KVAJHLSBDDVJOR-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]piperidine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1CCN(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)CC1 KVAJHLSBDDVJOR-UHFFFAOYSA-N 0.000 claims description 5
- PNQYZKFFFUKYBK-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]propyl]benzamide Chemical compound C=1C=C(CN2CCCC2)C=CC=1C(C)CNC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 PNQYZKFFFUKYBK-UHFFFAOYSA-N 0.000 claims description 5
- OVOCPCKORZMCDI-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-methyl-2-[4-(pyrrolidin-1-ylmethyl)phenyl]propyl]benzamide Chemical compound C=1C=C(CN2CCCC2)C=CC=1C(C)(C)CNC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 OVOCPCKORZMCDI-UHFFFAOYSA-N 0.000 claims description 5
- NLVRNLUYDGRJTF-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[[4-(pyrrolidin-1-ylmethyl)phenyl]methoxy]benzamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)NOCC=2C=CC(CN3CCCC3)=CC=2)C=C1 NLVRNLUYDGRJTF-UHFFFAOYSA-N 0.000 claims description 5
- BBUQOQOCPWXCAH-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]piperidine-1-carboxamide Chemical compound C1CC(C2CCCCC2)CCN1C(=O)NCCC(C=C1)=CC=C1CN1CCCC1 BBUQOQOCPWXCAH-UHFFFAOYSA-N 0.000 claims description 5
- PXTGRFIHXMQYFA-UHFFFAOYSA-N 4-piperidin-1-yl-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C=1C=C(N2CCCCC2)C=CC=1C(=O)NCCC(C=C1)=CC=C1CN1CCCC1 PXTGRFIHXMQYFA-UHFFFAOYSA-N 0.000 claims description 5
- WOFBOMJPFBPUGR-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]-3h-isoindol-1-one Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)N(CCC=2C=CC(CN3CCCC3)=CC=2)C2)C2=C1 WOFBOMJPFBPUGR-UHFFFAOYSA-N 0.000 claims description 5
- GSNQAMUYAPMCRN-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]isoquinolin-1-one Chemical compound C1=CC(Cl)=CC=C1C1=CC=C2C(=O)N(CCC=3C=CC(CN4CCCC4)=CC=3)C=CC2=C1 GSNQAMUYAPMCRN-UHFFFAOYSA-N 0.000 claims description 5
- NEMZEOGGJZBCCY-UHFFFAOYSA-N 7-(4-chlorophenyl)-3-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]quinazolin-4-one Chemical compound C1=CC(Cl)=CC=C1C1=CC=C2C(=O)N(CCC=3C=CC(CN4CCCC4)=CC=3)C=NC2=C1 NEMZEOGGJZBCCY-UHFFFAOYSA-N 0.000 claims description 5
- JKPOEURLDWJJDS-UHFFFAOYSA-N 7-(4-chlorophenyl)-3-[2-[4-[(4-hydroxy-4-phenylpiperidin-1-yl)methyl]phenyl]ethyl]quinazolin-4-one Chemical compound C1CC(O)(C=2C=CC=CC=2)CCN1CC(C=C1)=CC=C1CCN(C(C1=CC=2)=O)C=NC1=CC=2C1=CC=C(Cl)C=C1 JKPOEURLDWJJDS-UHFFFAOYSA-N 0.000 claims description 5
- 206010012655 Diabetic complications Diseases 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
- 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
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical class C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 4
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 4
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 claims description 4
- VRWWCRNCXHQFSX-UHFFFAOYSA-N 2-(4-methylphenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]piperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1C1N(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)CCCC1 VRWWCRNCXHQFSX-UHFFFAOYSA-N 0.000 claims description 4
- BRYDLOYWASHVMM-UHFFFAOYSA-N 2-methyl-3-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]-7-[4-(trifluoromethyl)phenyl]quinazolin-4-one Chemical compound CC1=NC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2C(=O)N1CCC(C=C1)=CC=C1CN1CCCC1 BRYDLOYWASHVMM-UHFFFAOYSA-N 0.000 claims description 4
- NYDXOPYTOGGQKB-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[4-(piperidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C(=O)NCCC=2C=CC(CN3CCCCC3)=CC=2)C=C1 NYDXOPYTOGGQKB-UHFFFAOYSA-N 0.000 claims description 4
- QDJMMGIVDMMNRQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]cyclohexane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1CCC(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)CC1 QDJMMGIVDMMNRQ-UHFFFAOYSA-N 0.000 claims description 4
- JMLYYTPQHKHZIM-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]piperazine-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1CCN(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)CC1 JMLYYTPQHKHZIM-UHFFFAOYSA-N 0.000 claims description 4
- VETIKOKPOQQSDW-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]ethyl]benzamide Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1CCNC(=O)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 VETIKOKPOQQSDW-UHFFFAOYSA-N 0.000 claims description 4
- XCUHTSQIVYYDJW-UHFFFAOYSA-N 4-(4-ethylphenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C1=CC(CC)=CC=C1C1=CC=C(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)C=C1 XCUHTSQIVYYDJW-UHFFFAOYSA-N 0.000 claims description 4
- ZOYANYCYKPVGLQ-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)C=C1 ZOYANYCYKPVGLQ-UHFFFAOYSA-N 0.000 claims description 4
- YMMPMGCLFJXVMV-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]piperidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1C1CCN(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)CC1 YMMPMGCLFJXVMV-UHFFFAOYSA-N 0.000 claims description 4
- GXAFKYXIWVWSQZ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]piperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)NCCC=2C=CC(CN3CCCC3)=CC=2)CC1 GXAFKYXIWVWSQZ-UHFFFAOYSA-N 0.000 claims description 4
- XAVVMVUGDWOKQN-UHFFFAOYSA-N 4-[(4-oxocyclohexylidene)methyl]-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C=1C=C(C=C2CCC(=O)CC2)C=CC=1C(=O)NCCC(C=C1)=CC=C1CN1CCCC1 XAVVMVUGDWOKQN-UHFFFAOYSA-N 0.000 claims description 4
- SWLOGIYVRRDNGZ-UHFFFAOYSA-N 4-benzyl-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C=1C=C(CC=2C=CC=CC=2)C=CC=1C(=O)NCCC(C=C1)=CC=C1CN1CCCC1 SWLOGIYVRRDNGZ-UHFFFAOYSA-N 0.000 claims description 4
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- NSSNDZJIWHUMLB-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethyl]benzamide Chemical compound C=1C=C(C2CCCCC2)C=CC=1C(=O)NCCC(C=C1)=CC=C1CN1CCCC1 NSSNDZJIWHUMLB-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
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- Urology & Nephrology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10238865A DE10238865A1 (de) | 2002-08-24 | 2002-08-24 | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
PCT/EP2003/009099 WO2004024702A1 (de) | 2002-08-24 | 2003-08-16 | Neue carbonsäureamid-verbindungen mit mch-antagonistischer wirkung, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20050179A2 true HRP20050179A2 (en) | 2006-05-31 |
Family
ID=31501914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20050179A HRP20050179A2 (en) | 2002-08-24 | 2005-02-23 | Novel carboxamide compounds having an mch-antagonistic effect, medicaments containing said compounds, and methods for the production thereof |
Country Status (21)
Country | Link |
---|---|
EP (1) | EP1534689A1 (es) |
JP (1) | JP2006507246A (es) |
KR (1) | KR20050040928A (es) |
CN (1) | CN1678591A (es) |
AR (1) | AR043046A1 (es) |
AU (1) | AU2003258620A1 (es) |
BR (1) | BR0313790A (es) |
CA (1) | CA2496563A1 (es) |
DE (1) | DE10238865A1 (es) |
EA (1) | EA012834B1 (es) |
EC (1) | ECSP055615A (es) |
HR (1) | HRP20050179A2 (es) |
MX (1) | MXPA05002158A (es) |
NO (1) | NO20050068L (es) |
PE (1) | PE20040974A1 (es) |
PL (1) | PL375344A1 (es) |
RS (1) | RS20050173A (es) |
TW (1) | TW200413332A (es) |
UA (1) | UA82853C2 (es) |
WO (1) | WO2004024702A1 (es) |
ZA (1) | ZA200500086B (es) |
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US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
WO2004072018A1 (ja) | 2003-02-12 | 2004-08-26 | Takeda Pharmaceutical Company Limited | アミン誘導体 |
CA2540826A1 (en) | 2003-10-01 | 2005-04-14 | The Procter & Gamble Company | Melanin concentrating hormone antagonists |
JP4667384B2 (ja) * | 2003-10-07 | 2011-04-13 | レノビス, インコーポレイテッド | イオンチャネルリガンドとしてのアミド誘導体および薬学的組成物、ならびにこれらを使用する方法 |
US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
DE102004017934A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
US7524862B2 (en) | 2004-04-14 | 2009-04-28 | Boehringer Ingelheim International Gmbh | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
RU2353362C2 (ru) * | 2004-05-25 | 2009-04-27 | Пфайзер Продактс Инк. | Новое применение |
TW200613272A (en) * | 2004-08-13 | 2006-05-01 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
DE102004039789A1 (de) | 2004-08-16 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Arylsubstituierte polycyclische Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
CA2594345C (en) | 2004-12-28 | 2013-11-05 | Kinex Pharmaceuticals, Llc | Compositions and methods of treating cell proliferation disorders |
US7968574B2 (en) | 2004-12-28 | 2011-06-28 | Kinex Pharmaceuticals, Llc | Biaryl compositions and methods for modulating a kinase cascade |
WO2007021308A1 (en) * | 2005-08-12 | 2007-02-22 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
US7807706B2 (en) | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
ES2412007T3 (es) | 2005-12-21 | 2013-07-09 | Janssen Pharmaceutica, N.V. | Derivados de pirazinona sustituida novedosos para uso en enfermedades mediadas por MCH-1 |
TW200804347A (en) | 2006-01-10 | 2008-01-16 | Janssen Pharmaceutica Nv | Urotensin II receptor antagonists |
TW200800908A (en) * | 2006-02-15 | 2008-01-01 | Sanofi Aventis | Novel azacyclyl-substituted aryldihydroisoquinolinones, process for their preparation and their use as medicaments |
CN101384555A (zh) | 2006-02-15 | 2009-03-11 | 塞诺菲-安万特股份有限公司 | 新的氨基醇取代的芳基二氢异喹啉酮类、其制备方法以及其作为药物的用途 |
KR20080096670A (ko) * | 2006-02-15 | 2008-10-31 | 사노피-아벤티스 | 신규한 아미노 알콜-치환된 아릴티에노피리미디논, 이의 제조 방법 및 약제로서 이의 용도 |
BRPI0707869A2 (pt) * | 2006-02-15 | 2011-05-10 | Sanofi Aventis | ariltienopirimidinonas substituÍdas com azaciclil, processo para a sua preparaÇço e seus usos como medicamentos |
TWI398440B (zh) * | 2006-06-29 | 2013-06-11 | Kinex Pharmaceuticals Llc | 雙芳基組成物與調節激酶級聯之方法 |
EP2041071B1 (en) | 2006-06-29 | 2014-06-18 | Kinex Pharmaceuticals, LLC | Biaryl compositions and methods for modulating a kinase cascade |
EP2049120A4 (en) | 2006-07-31 | 2011-09-07 | Janssen Pharmaceutica Nv | UROTENSIN II RECEPTOR ANTAGONISTS |
KR20090047542A (ko) | 2006-08-25 | 2009-05-12 | 베링거 인겔하임 인터내셔날 게엠베하 | Mch 길항 활성을 갖는 신규한 피리돈 유도체 및 당해 화합물을 포함하는 의약 |
WO2008068265A1 (en) | 2006-12-05 | 2008-06-12 | Janssen Pharmaceutica N.V. | Novel substituted diaza spiro pyridinone derivatives for use in mch-1 mediated diseases |
WO2008071646A1 (en) | 2006-12-11 | 2008-06-19 | Boehringer Ingelheim International Gmbh | New pyridazine derivatives with mch antagonistic activity and medicaments comprising these compounds |
US7935697B2 (en) | 2006-12-28 | 2011-05-03 | Kinex Pharmaceuticals, Llc | Compositions for modulating a kinase cascade and methods of use thereof |
MX2009007209A (es) * | 2007-01-03 | 2009-10-12 | Cortex Pharma Inc | Compuestos de [1, 2, 3]-benzotriazinona-sustituidos en la posicion 3 para mejorar las respuestas sinapticas glutamatergicas. |
US8093265B2 (en) | 2007-03-09 | 2012-01-10 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
TWI417100B (zh) | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-842之用途 |
EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
CN101412682B (zh) * | 2007-10-19 | 2012-06-27 | 上海药明康德新药开发有限公司 | 芳基氨茴酸及其衍生物的合成方法 |
US8314107B2 (en) * | 2008-04-23 | 2012-11-20 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds and methods for using the same |
SA109300358B1 (ar) | 2008-06-06 | 2012-11-03 | استرازينيكا ايه بي | مقويات مستقبل جلوتامات ذي انتحاء أيضي من أيزو إندولون |
EP2326644B1 (en) | 2008-08-02 | 2012-02-22 | Janssen Pharmaceutica N.V. | Urotensin ii receptor antagonists |
AR075402A1 (es) | 2009-02-13 | 2011-03-30 | Sanofi Aventis | Derivados heterociclicos oxigenados y/o nitrogenados de tetrahidronaftaleno, medicamentos que los contienen y uso de los mismos en el tratamiento de trastornos metabolicos, tales como obesidad,entre otros. |
UY32442A (es) | 2009-02-13 | 2010-09-30 | Sanofi Aventis | Nuevos indanos sustituidos, procesos para su preparacion y uso de los mismos como un medicamento |
CN102905700A (zh) | 2010-04-16 | 2013-01-30 | 金克斯医药品有限公司 | 用于预防和治疗癌症的组合物以及方法 |
GB201009853D0 (en) | 2010-06-11 | 2010-07-21 | Chroma Therapeutics Ltd | HSP90 inhibitors |
NZ617987A (en) | 2011-05-10 | 2016-02-26 | Gilead Sciences Inc | Fused heterocyclic compounds as sodium channel modulators |
NO3175985T3 (es) | 2011-07-01 | 2018-04-28 | ||
TWI478908B (zh) | 2011-07-01 | 2015-04-01 | Gilead Sciences Inc | 作為離子通道調節劑之稠合雜環化合物 |
UY34194A (es) * | 2011-07-15 | 2013-02-28 | Astrazeneca Ab | ?(3-(4-(espiroheterocíclico)metil)fenoxi)azetidin-1-il)(5-(fenil)-1,3,4-oxadiazol-2-il)metanona en el tratamiento de la obesidad? |
US8933079B2 (en) * | 2012-03-07 | 2015-01-13 | Boehringer Ingelheim International Gmbh | Pyridone and pyridazinone derivatives as anti-obesity agents |
SI2890680T1 (en) | 2012-08-30 | 2018-08-31 | Athenex, Inc. Conventus Building | N- (3-FLUOROBENZYL) -2- (5- (4-MORFOLINOPHENYL) PIRIDIN-2-IL) ACETAMIDE AS PROTEIN TIROZINE KINASE PROTECTORS |
FR3000491B1 (fr) * | 2012-09-27 | 2015-08-28 | Univ Lille Ii Droit & Sante | Composes utilisables dans le traitement des infections mycobacteriennes |
CN110407824B (zh) * | 2019-08-08 | 2021-07-02 | 安徽医科大学 | 芳基甲酰胺类化合物及其制备方法、药物组合物及用途 |
US20220380314A1 (en) * | 2019-09-17 | 2022-12-01 | Bial - R&D Investments, S.A. | Substituted, saturated and unsaturated n-heterocyclic carboxamides and related compounds for their use in the treatment of medical disorders |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1218336A2 (en) * | 1999-09-20 | 2002-07-03 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
AU2001256733A1 (en) * | 2000-05-16 | 2001-11-26 | Takeda Chemical Industries Ltd. | Melanin-concentrating hormone antagonist |
WO2002006245A1 (en) * | 2000-07-05 | 2002-01-24 | Synaptic Pharmarceutical Corporation | Selective melanin concentrating hormone-1 (mch1) receptor antagonists and uses thereof |
US20030022891A1 (en) * | 2000-12-01 | 2003-01-30 | Anandan Palani | MCH antagonists and their use in the treatment of obesity |
WO2002051809A1 (en) * | 2000-12-22 | 2002-07-04 | Schering Corporation | Piperidine mch antagonists and their use in the treatment of obesity |
GB0124627D0 (en) * | 2001-10-15 | 2001-12-05 | Smithkline Beecham Plc | Novel compounds |
GB0124931D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
-
2002
- 2002-08-24 DE DE10238865A patent/DE10238865A1/de not_active Withdrawn
-
2003
- 2003-08-16 WO PCT/EP2003/009099 patent/WO2004024702A1/de active Application Filing
- 2003-08-16 BR BR0313790-2A patent/BR0313790A/pt not_active Expired - Fee Related
- 2003-08-16 PL PL03375344A patent/PL375344A1/xx not_active Application Discontinuation
- 2003-08-16 RS YUP-2005/0173A patent/RS20050173A/sr unknown
- 2003-08-16 MX MXPA05002158A patent/MXPA05002158A/es unknown
- 2003-08-16 JP JP2004535098A patent/JP2006507246A/ja active Pending
- 2003-08-16 EP EP03794886A patent/EP1534689A1/de not_active Withdrawn
- 2003-08-16 EA EA200500301A patent/EA012834B1/ru not_active IP Right Cessation
- 2003-08-16 CA CA002496563A patent/CA2496563A1/en not_active Abandoned
- 2003-08-16 AU AU2003258620A patent/AU2003258620A1/en not_active Abandoned
- 2003-08-16 CN CNA038200767A patent/CN1678591A/zh active Pending
- 2003-08-16 UA UAA200502601A patent/UA82853C2/uk unknown
- 2003-08-16 KR KR1020057003110A patent/KR20050040928A/ko not_active Application Discontinuation
- 2003-08-21 PE PE2003000849A patent/PE20040974A1/es not_active Application Discontinuation
- 2003-08-22 AR ARP030103034A patent/AR043046A1/es unknown
- 2003-08-22 TW TW092123197A patent/TW200413332A/zh unknown
-
2005
- 2005-01-05 ZA ZA200500086A patent/ZA200500086B/xx unknown
- 2005-01-06 NO NO20050068A patent/NO20050068L/no not_active Application Discontinuation
- 2005-02-18 EC EC2005005615A patent/ECSP055615A/es unknown
- 2005-02-23 HR HR20050179A patent/HRP20050179A2/hr not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
UA82853C2 (en) | 2008-05-26 |
PE20040974A1 (es) | 2005-01-12 |
BR0313790A (pt) | 2005-07-12 |
JP2006507246A (ja) | 2006-03-02 |
NO20050068L (no) | 2005-03-04 |
KR20050040928A (ko) | 2005-05-03 |
ECSP055615A (es) | 2005-05-30 |
AU2003258620A1 (en) | 2004-04-30 |
MXPA05002158A (es) | 2005-05-23 |
EA012834B1 (ru) | 2009-12-30 |
RS20050173A (en) | 2007-09-21 |
DE10238865A1 (de) | 2004-03-11 |
AR043046A1 (es) | 2005-07-13 |
EP1534689A1 (de) | 2005-06-01 |
PL375344A1 (en) | 2005-11-28 |
WO2004024702A1 (de) | 2004-03-25 |
TW200413332A (en) | 2004-08-01 |
ZA200500086B (en) | 2006-07-26 |
CA2496563A1 (en) | 2004-03-25 |
CN1678591A (zh) | 2005-10-05 |
EA200500301A1 (ru) | 2006-02-24 |
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