CA2550649A1 - 3-(4-piperidine-1ylmethyl-phenyl)-propion acid-phenylamide-derivatives and related compounds used in the form of mch antagonists (melanine concentrating hormone) for treating eating disorders - Google Patents
3-(4-piperidine-1ylmethyl-phenyl)-propion acid-phenylamide-derivatives and related compounds used in the form of mch antagonists (melanine concentrating hormone) for treating eating disorders Download PDFInfo
- Publication number
- CA2550649A1 CA2550649A1 CA002550649A CA2550649A CA2550649A1 CA 2550649 A1 CA2550649 A1 CA 2550649A1 CA 002550649 A CA002550649 A CA 002550649A CA 2550649 A CA2550649 A CA 2550649A CA 2550649 A1 CA2550649 A1 CA 2550649A1
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- CA
- Canada
- Prior art keywords
- alkyl
- phenyl
- group
- amino
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 161
- 239000005557 antagonist Substances 0.000 title claims abstract description 25
- 208000030814 Eating disease Diseases 0.000 title claims abstract description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 title claims abstract description 5
- 235000014632 disordered eating Nutrition 0.000 title claims abstract description 5
- 229940088597 hormone Drugs 0.000 title 1
- 239000005556 hormone Substances 0.000 title 1
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 18
- 206010061428 decreased appetite Diseases 0.000 claims abstract description 9
- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 8
- 230000000694 effects Effects 0.000 claims abstract description 6
- 208000032841 Bulimia Diseases 0.000 claims abstract description 5
- 206010020710 Hyperphagia Diseases 0.000 claims abstract description 4
- 208000022531 anorexia Diseases 0.000 claims abstract description 4
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 4
- -1 Amide compounds Chemical class 0.000 claims description 227
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 130
- 125000004432 carbon atom Chemical group C* 0.000 claims description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 55
- 239000013543 active substance Substances 0.000 claims description 53
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 53
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 208000008589 Obesity Diseases 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 235000020824 obesity Nutrition 0.000 claims description 38
- 229910052794 bromium Inorganic materials 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
- 125000004122 cyclic group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 229910052731 fluorine Inorganic materials 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 230000037396 body weight Effects 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 230000036961 partial effect Effects 0.000 claims description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 206010003246 arthritis Diseases 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
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- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 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
- 239000003085 diluting agent Substances 0.000 claims description 7
- 230000020595 eating behavior Effects 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 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
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 208000002249 Diabetes Complications Diseases 0.000 claims description 5
- 206010012655 Diabetic complications Diseases 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 208000021891 Micturition disease Diseases 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 208000030159 metabolic disease Diseases 0.000 claims description 4
- 230000001575 pathological effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- OCELZDDEJJBFSU-UHFFFAOYSA-N 2-chloro-5-[3-[4-(5-phenylpentylamino)phenyl]propanoylamino]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(NC(=O)CCC=2C=CC(NCCCCCC=3C=CC=CC=3)=CC=2)=C1 OCELZDDEJJBFSU-UHFFFAOYSA-N 0.000 claims description 3
- RQCSDMPDPILTRX-UHFFFAOYSA-N 2-methylsulfanyl-5-[3-[4-(octadecylamino)phenyl]propanoylamino]benzoic acid Chemical compound C1=CC(NCCCCCCCCCCCCCCCCCC)=CC=C1CCC(=O)NC1=CC=C(SC)C(C(O)=O)=C1 RQCSDMPDPILTRX-UHFFFAOYSA-N 0.000 claims description 3
- NPVONNZNIBNQBN-UHFFFAOYSA-N 3-(4-aminophenyl)-n-(4-hydroxy-3,5-dimethylphenyl)propanamide Chemical compound CC1=C(O)C(C)=CC(NC(=O)CCC=2C=CC(N)=CC=2)=C1 NPVONNZNIBNQBN-UHFFFAOYSA-N 0.000 claims description 3
- OOOPKDWRISJSLD-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-n-(4-hydroxy-3,5-dimethylphenyl)propanamide Chemical compound C1=CC(N(C)C)=CC=C1CCC(=O)NC1=CC(C)=C(O)C(C)=C1 OOOPKDWRISJSLD-UHFFFAOYSA-N 0.000 claims description 3
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 3
- LSFSTMXFFDNMJQ-UHFFFAOYSA-N 4-[3-[3-(2-anilino-1,3-benzoxazol-6-yl)propanoylamino]phenoxy]butanoic acid Chemical compound OC(=O)CCCOC1=CC=CC(NC(=O)CCC=2C=C3OC(NC=4C=CC=CC=4)=NC3=CC=2)=C1 LSFSTMXFFDNMJQ-UHFFFAOYSA-N 0.000 claims description 3
- 241001421185 Anomis Species 0.000 claims description 3
- 206010006895 Cachexia Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 206010007882 Cellulitis Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 208000027534 Emotional disease Diseases 0.000 claims description 3
- 208000008967 Enuresis Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
- 201000008736 Systemic mastocytosis Diseases 0.000 claims description 3
- 238000009825 accumulation Methods 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 230000003054 hormonal effect Effects 0.000 claims description 3
- 150000002466 imines Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 230000003211 malignant effect Effects 0.000 claims description 3
- 208000008585 mastocytosis Diseases 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- CYNDKGIQZOATHH-UHFFFAOYSA-N n-[2-[3-(dimethylamino)propylsulfanyl]phenyl]-3-phenylprop-2-ynamide Chemical compound CN(C)CCCSC1=CC=CC=C1NC(=O)C#CC1=CC=CC=C1 CYNDKGIQZOATHH-UHFFFAOYSA-N 0.000 claims description 3
- 206010029446 nocturia Diseases 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 230000001850 reproductive effect Effects 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
- YHCUZRJTNSWYCY-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-azepine Chemical compound C1CNCC=CC1 YHCUZRJTNSWYCY-UHFFFAOYSA-N 0.000 claims description 2
- SMOHMDMTVAYPAI-UHFFFAOYSA-N 2,3,6,7-tetrahydro-1h-azepine Chemical compound C1CC=CCCN1 SMOHMDMTVAYPAI-UHFFFAOYSA-N 0.000 claims description 2
- HOHMNKIRZPSFKU-UHFFFAOYSA-N 3-[2-[2-hydroxy-3-(4-naphthalen-1-ylpiperidin-1-yl)propoxy]phenyl]-n-methyl-n-phenylprop-2-enamide Chemical compound C=1C=CC=C(OCC(O)CN2CCC(CC2)C=2C3=CC=CC=C3C=CC=2)C=1C=CC(=O)N(C)C1=CC=CC=C1 HOHMNKIRZPSFKU-UHFFFAOYSA-N 0.000 claims description 2
- GNWONDUZVUZUOQ-UHFFFAOYSA-N 3-[2-[2-hydroxy-3-(4-naphthalen-2-yl-3,6-dihydro-2h-pyridin-1-yl)propoxy]phenyl]-n-methyl-n-phenylprop-2-enamide Chemical compound C=1C=CC=C(OCC(O)CN2CC=C(CC2)C=2C=C3C=CC=CC3=CC=2)C=1C=CC(=O)N(C)C1=CC=CC=C1 GNWONDUZVUZUOQ-UHFFFAOYSA-N 0.000 claims description 2
- ZXURMRFAXFYMAD-UHFFFAOYSA-N 3-[2-[2-hydroxy-3-(4-naphthalen-2-ylpiperidin-1-yl)propoxy]phenyl]-n-methyl-n-phenylprop-2-enamide Chemical compound C=1C=CC=C(OCC(O)CN2CCC(CC2)C=2C=C3C=CC=CC3=CC=2)C=1C=CC(=O)N(C)C1=CC=CC=C1 ZXURMRFAXFYMAD-UHFFFAOYSA-N 0.000 claims description 2
- TXLCWKXYBRECFJ-UHFFFAOYSA-N 3-[2-[2-hydroxy-3-(4-naphthalen-2-ylpiperidin-1-yl)propoxy]phenyl]-n-phenylprop-2-enamide Chemical compound C1CC(C=2C=C3C=CC=CC3=CC=2)CCN1CC(O)COC1=CC=CC=C1C=CC(=O)NC1=CC=CC=C1 TXLCWKXYBRECFJ-UHFFFAOYSA-N 0.000 claims description 2
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 2
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- 230000036506 anxiety Effects 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
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- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 2
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- VJNSFUXBIQJGSE-UHFFFAOYSA-N methyl 2-chloro-5-[3-[4-(5-phenylpentylamino)phenyl]propanoylamino]benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC(NC(=O)CCC=2C=CC(NCCCCCC=3C=CC=CC=3)=CC=2)=C1 VJNSFUXBIQJGSE-UHFFFAOYSA-N 0.000 claims description 2
- YAZGADZUKMSMOV-UHFFFAOYSA-N n-piperidin-4-ylidenehydroxylamine Chemical compound ON=C1CCNCC1 YAZGADZUKMSMOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
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- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 56
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 10
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
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- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
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- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 abstract description 10
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- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 abstract 1
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000002585 base Substances 0.000 description 19
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- ZJEMFURAGDYBTG-UHFFFAOYSA-N tert-butyl n-[1-(4-bromophenyl)cyclopropyl]carbamate Chemical compound C=1C=C(Br)C=CC=1C1(NC(=O)OC(C)(C)C)CC1 ZJEMFURAGDYBTG-UHFFFAOYSA-N 0.000 description 1
- CEXABDQWFYZLSS-UHFFFAOYSA-N tert-butyl n-[1-(4-iodophenyl)cyclopropyl]-n-methylcarbamate Chemical compound C=1C=C(I)C=CC=1C1(N(C(=O)OC(C)(C)C)C)CC1 CEXABDQWFYZLSS-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
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- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D487/04—Ortho-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
- C07D487/08—Bridged systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Gynecology & Obstetrics (AREA)
- Emergency Medicine (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10360745.5 | 2003-12-23 | ||
| DE10360745A DE10360745A1 (de) | 2003-12-23 | 2003-12-23 | Neue Amid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| PCT/EP2004/014378 WO2005063239A1 (de) | 2003-12-23 | 2004-12-17 | 3-(4-piperidin-1ylmethyl-phenyl) -propionsäure-phrnylamid-derivate und verwandte verbindungen als mch (melanine concentrating hormone) antagonisten zur behandlung von essstörungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2550649A1 true CA2550649A1 (en) | 2005-07-14 |
Family
ID=34706476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002550649A Abandoned CA2550649A1 (en) | 2003-12-23 | 2004-12-17 | 3-(4-piperidine-1ylmethyl-phenyl)-propion acid-phenylamide-derivatives and related compounds used in the form of mch antagonists (melanine concentrating hormone) for treating eating disorders |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1708698A1 (enExample) |
| JP (1) | JP2007520466A (enExample) |
| AR (1) | AR048019A1 (enExample) |
| CA (1) | CA2550649A1 (enExample) |
| DE (1) | DE10360745A1 (enExample) |
| PE (1) | PE20050678A1 (enExample) |
| TW (1) | TW200530180A (enExample) |
| UY (1) | UY28689A1 (enExample) |
| WO (1) | WO2005063239A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
| AU2006226775A1 (en) * | 2005-03-24 | 2006-09-28 | Janssen Pharmaceutica, N.V. | Biaryl derived amide modulators of vanilloid VR1 receptor |
| US20070111981A1 (en) * | 2005-10-26 | 2007-05-17 | Roth Gerald J | New (hetero)aryl compounds with MCH antagonistic activity and medicaments comprising these compounds |
| US7977346B2 (en) * | 2006-01-17 | 2011-07-12 | Guoqing Paul Chen | Spiro compounds and methods of use |
| CA2657183A1 (en) | 2006-08-25 | 2008-02-28 | Boehringer Ingelheim International Gmbh | New pyridone derivatives with mch antagonistic activity and medicaments comprising these compounds |
| TW200831485A (en) | 2006-12-11 | 2008-08-01 | Boehringer Ingelheim Int | New pyridazine derivatives with MCH antagonistic activity and medicaments comprising these compounds |
| JP5722892B2 (ja) | 2010-07-15 | 2015-05-27 | 武田薬品工業株式会社 | 複素環化合物 |
| WO2022165513A1 (en) | 2021-01-29 | 2022-08-04 | Cedilla Therapeutics, Inc. | Cdk2 inhibitors and methods of using the same |
| US12053459B2 (en) | 2021-06-26 | 2024-08-06 | Cedilla Therapeutics, Inc. | CDK2 inhibitors and methods of using the same |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8530507D0 (en) * | 1985-12-11 | 1986-01-22 | Glaxo Group Plc | Chemical compounds |
| JPH0454118A (ja) * | 1990-06-20 | 1992-02-21 | Tanabe Seiyaku Co Ltd | 5―リポキシゲナーゼ阻害剤 |
| EP0810220B1 (en) * | 1996-05-28 | 2001-12-12 | Pfizer Inc. | Arylacrylamide derivatives as 5HT1 agonists or antagonists |
| EP1037880B1 (en) * | 1997-12-11 | 2004-06-30 | Janssen Pharmaceutica N.V. | Retinoic acid mimetic anilides |
| JP2000143635A (ja) * | 1998-06-10 | 2000-05-26 | Takeda Chem Ind Ltd | 血管新生阻害剤 |
| JP2000086603A (ja) * | 1998-07-15 | 2000-03-28 | Yoshitomi Pharmaceut Ind Ltd | 桂皮酸アミド誘導体および3―フェニルプロピオン酸アミド誘導体 |
| WO2000005223A2 (en) * | 1998-07-23 | 2000-02-03 | Astrazeneca Ab | Heterocyclic derivatives and their use as integrin inhibitors |
| DK1153017T3 (da) * | 1999-02-16 | 2006-07-17 | Aventis Pharma Ltd | Bicykliske forbindelser og deres anvendelse som integrinreceptorligander |
| CA2376553A1 (en) * | 1999-07-01 | 2001-01-11 | Taisho Pharmaceutical Co., Ltd. | Aminobenzoic acid derivatives |
| JP2002003370A (ja) * | 1999-09-20 | 2002-01-09 | Takeda Chem Ind Ltd | メラニン凝集ホルモン拮抗剤 |
| DE10115994A1 (de) * | 2001-03-30 | 2002-10-10 | Wella Ag | (p-Amino-hydroxyphenyl)acrylamid-Derivate und diese Verbindungen enthaltende Färbemittel |
| EP1391199B1 (en) * | 2001-05-10 | 2008-12-10 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| US6897220B2 (en) * | 2001-09-14 | 2005-05-24 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| WO2003045920A1 (en) * | 2001-11-27 | 2003-06-05 | Merck & Co., Inc. | 4-aminoquinoline compounds |
| JP2005519876A (ja) * | 2001-11-27 | 2005-07-07 | メルク エンド カムパニー インコーポレーテッド | 2−アミノキノリン化合物 |
| CA2468544A1 (en) * | 2001-12-10 | 2003-06-19 | Amgen Inc. | Vanilloid receptor ligands |
| ES2444550T3 (es) * | 2002-08-29 | 2014-02-25 | Temple University - Of The Commonwealth System Of Higher Education | Arilpropenamidas y heteroarilpropenamidas, derivados de las mismas y usos terapéuticos de las mismas |
| CA2514940A1 (en) * | 2003-02-03 | 2004-08-19 | Janssen Pharmaceutica N.V. | Quinoline-derived amide modulators of vanilloid vr1 receptor |
| WO2004072018A1 (ja) * | 2003-02-12 | 2004-08-26 | Takeda Pharmaceutical Company Limited | アミン誘導体 |
| JP4630555B2 (ja) * | 2003-02-12 | 2011-02-09 | 武田薬品工業株式会社 | アミン誘導体 |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
-
2003
- 2003-12-23 DE DE10360745A patent/DE10360745A1/de not_active Withdrawn
-
2004
- 2004-12-17 EP EP04803987A patent/EP1708698A1/de not_active Withdrawn
- 2004-12-17 WO PCT/EP2004/014378 patent/WO2005063239A1/de not_active Ceased
- 2004-12-17 JP JP2006546009A patent/JP2007520466A/ja active Pending
- 2004-12-17 CA CA002550649A patent/CA2550649A1/en not_active Abandoned
- 2004-12-20 UY UY28689A patent/UY28689A1/es not_active Application Discontinuation
- 2004-12-22 TW TW093140144A patent/TW200530180A/zh unknown
- 2004-12-22 AR ARP040104840A patent/AR048019A1/es unknown
-
2005
- 2005-01-03 PE PE2005000007A patent/PE20050678A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE10360745A1 (de) | 2005-07-28 |
| WO2005063239A1 (de) | 2005-07-14 |
| PE20050678A1 (es) | 2005-10-27 |
| WO2005063239A9 (de) | 2006-03-09 |
| JP2007520466A (ja) | 2007-07-26 |
| EP1708698A1 (de) | 2006-10-11 |
| AR048019A1 (es) | 2006-03-22 |
| TW200530180A (en) | 2005-09-16 |
| UY28689A1 (es) | 2005-08-31 |
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