UA82853C2 - Carboxamide compounds having an mch-antagonistic effect, medicaments containing said compounds, and methods for the production thereof - Google Patents
Carboxamide compounds having an mch-antagonistic effect, medicaments containing said compounds, and methods for the production thereof Download PDFInfo
- Publication number
- UA82853C2 UA82853C2 UAA200502601A UA2005002601A UA82853C2 UA 82853 C2 UA82853 C2 UA 82853C2 UA A200502601 A UAA200502601 A UA A200502601A UA 2005002601 A UA2005002601 A UA 2005002601A UA 82853 C2 UA82853 C2 UA 82853C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- pyrrolidin
- phenyl
- carboxylic acid
- ylmethylphenyl
- Prior art date
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- -1 Carboxamide compounds Chemical class 0.000 title claims abstract description 332
- 150000001875 compounds Chemical class 0.000 title claims description 252
- 238000000034 method Methods 0.000 title abstract description 46
- 230000000694 effects Effects 0.000 title abstract description 7
- 239000003814 drug Substances 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 208000008589 Obesity Diseases 0.000 claims abstract description 38
- 235000020824 obesity Nutrition 0.000 claims abstract description 38
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 14
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 176
- VBYIYDQHYIBKLT-UHFFFAOYSA-N 2-[4-(pyrrolidin-1-ylmethyl)phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1CN1CCCC1 VBYIYDQHYIBKLT-UHFFFAOYSA-N 0.000 claims description 116
- 125000004432 carbon atom Chemical group C* 0.000 claims description 107
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 69
- NEPBQXJWEIOLAZ-UHFFFAOYSA-N 1-chloro-4-phenylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound C1=CC(C(=O)O)(Cl)CC=C1C1=CC=CC=C1 NEPBQXJWEIOLAZ-UHFFFAOYSA-N 0.000 claims description 65
- 125000004122 cyclic group Chemical group 0.000 claims description 58
- 239000013543 active substance Substances 0.000 claims description 51
- 150000001408 amides Chemical class 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 42
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 41
- 230000015572 biosynthetic process Effects 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 239000012634 fragment Substances 0.000 claims description 31
- 125000003277 amino group Chemical group 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 239000005557 antagonist Substances 0.000 claims description 24
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 22
- 229910052740 iodine Inorganic materials 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 14
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 14
- 229940126601 medicinal product Drugs 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- IUEUTXMLGUDPDJ-UHFFFAOYSA-N 2-[4-(diethylaminomethyl)phenyl]ethanamine Chemical compound CCN(CC)CC1=CC=C(CCN)C=C1 IUEUTXMLGUDPDJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- AIJGCTDSHNJSDC-UHFFFAOYSA-N 2-[4-(piperidin-1-ylmethyl)phenyl]ethanamine Chemical compound C1=CC(CCN)=CC=C1CN1CCCCC1 AIJGCTDSHNJSDC-UHFFFAOYSA-N 0.000 claims description 8
- 208000002249 Diabetes Complications Diseases 0.000 claims description 7
- 206010012655 Diabetic complications Diseases 0.000 claims description 7
- 208000037849 arterial hypertension Diseases 0.000 claims description 7
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
- 206010003246 arthritis Diseases 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 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 7
- 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 6
- ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 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
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- DKEMFXGBRIXHKX-UHFFFAOYSA-N o-[[4-(pyrrolidin-1-ylmethyl)phenyl]methyl]hydroxylamine Chemical compound C1=CC(CON)=CC=C1CN1CCCC1 DKEMFXGBRIXHKX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
- DUNRVWWMEJBGSG-UHFFFAOYSA-N 2-[3-methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]ethanamine Chemical compound COC1=CC(CCN)=CC=C1CN1CCCC1 DUNRVWWMEJBGSG-UHFFFAOYSA-N 0.000 claims description 5
- 208000020401 Depressive disease Diseases 0.000 claims description 5
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000000969 carrier Substances 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
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- MAFJBVICDDRHEM-UHFFFAOYSA-N 2-[4-(pyrrolidin-1-ylmethyl)cyclohexyl]ethanamine Chemical compound C1CC(CCN)CCC1CN1CCCC1 MAFJBVICDDRHEM-UHFFFAOYSA-N 0.000 claims description 4
- SIVJJSMEYQFYOE-UHFFFAOYSA-N 2-methyl-2-[4-(pyrrolidin-1-ylmethyl)phenyl]propan-1-amine Chemical compound C1=CC(C(C)(CN)C)=CC=C1CN1CCCC1 SIVJJSMEYQFYOE-UHFFFAOYSA-N 0.000 claims description 4
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical group C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 4
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl 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 3
- WTGDAWBHDAELDS-UHFFFAOYSA-N C1C=C(C=CC1(C(=O)O)Br)C2=CC=CC=C2 Chemical compound C1C=C(C=CC1(C(=O)O)Br)C2=CC=CC=C2 WTGDAWBHDAELDS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 150000002466 imines Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 3
- HIGFRFFUZFLUKH-UHFFFAOYSA-N 1-fluoro-4-phenylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound C1=CC(C(=O)O)(F)CC=C1C1=CC=CC=C1 HIGFRFFUZFLUKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- XMRWNSRWTRPXAB-UHFFFAOYSA-N 2-[2-bromo-4-(pyrrolidin-1-ylmethyl)phenyl]ethanamine Chemical compound C1=C(Br)C(CCN)=CC=C1CN1CCCC1 XMRWNSRWTRPXAB-UHFFFAOYSA-N 0.000 claims description 2
- FDYVTINCLQGBCS-UHFFFAOYSA-N 2-[2-methyl-4-(pyrrolidin-1-ylmethyl)phenyl]ethanamine Chemical compound C1=C(CCN)C(C)=CC(CN2CCCC2)=C1 FDYVTINCLQGBCS-UHFFFAOYSA-N 0.000 claims description 2
- HZJQLGXIWLZCKX-UHFFFAOYSA-N 2-[2-nitro-4-(pyrrolidin-1-ylmethyl)phenyl]ethanamine Chemical compound C1=C([N+]([O-])=O)C(CCN)=CC=C1CN1CCCC1 HZJQLGXIWLZCKX-UHFFFAOYSA-N 0.000 claims description 2
- LJIFTMWXMUVNHN-UHFFFAOYSA-N 2-[3-bromo-4-(pyrrolidin-1-ylmethyl)phenyl]ethanamine Chemical compound BrC1=CC(CCN)=CC=C1CN1CCCC1 LJIFTMWXMUVNHN-UHFFFAOYSA-N 0.000 claims description 2
- BICAMTKPFIWHKR-UHFFFAOYSA-N 2-[6-(pyrrolidin-1-ylmethyl)pyridin-3-yl]ethanamine Chemical compound N1=CC(CCN)=CC=C1CN1CCCC1 BICAMTKPFIWHKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 claims description 2
- FRIRBHKMNMAHAB-UHFFFAOYSA-N 4-(4-methoxyphenyl)piperazine-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(C(O)=O)CC1 FRIRBHKMNMAHAB-UHFFFAOYSA-N 0.000 claims description 2
- UDQTWLFHYHRSRF-UHFFFAOYSA-N 4-phenylpiperidine-1-carboxylic acid Chemical compound C1CN(C(=O)O)CCC1C1=CC=CC=C1 UDQTWLFHYHRSRF-UHFFFAOYSA-N 0.000 claims description 2
- BDVOWOWFIGJSGC-UHFFFAOYSA-N CC1=CC=C(C=C1)C1N(CCCC1)C(=O)O Chemical compound CC1=CC=C(C=C1)C1N(CCCC1)C(=O)O BDVOWOWFIGJSGC-UHFFFAOYSA-N 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003725 azepanyl group Chemical group 0.000 claims description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000004069 aziridinyl group Chemical group 0.000 claims description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 2
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
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- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
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- APHNQJPTVLEMPC-UHFFFAOYSA-N pyrrolidin-2-ylmethylcarbamic acid Chemical compound OC(=O)NCC1CCCN1 APHNQJPTVLEMPC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- OYTZLDDBAITPJB-UHFFFAOYSA-N 4-(4-chlorophenyl)-3,6-dihydro-2h-pyridine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=CC(Cl)=CC=2)=C1 OYTZLDDBAITPJB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VRILHLKPFHWWSD-UHFFFAOYSA-N 5-(4-chlorophenyl)pyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1 VRILHLKPFHWWSD-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 402
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 366
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- 238000001514 detection method Methods 0.000 description 184
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 141
- 239000000243 solution Substances 0.000 description 137
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 129
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 118
- 238000006243 chemical reaction Methods 0.000 description 112
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- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- 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)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Child & Adolescent Psychology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Emergency 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 |
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UA82853C2 true UA82853C2 (en) | 2008-05-26 |
Family
ID=31501914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UAA200502601A UA82853C2 (en) | 2002-08-24 | 2003-08-16 | 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 (pt) |
JP (1) | JP2006507246A (pt) |
KR (1) | KR20050040928A (pt) |
CN (1) | CN1678591A (pt) |
AR (1) | AR043046A1 (pt) |
AU (1) | AU2003258620A1 (pt) |
BR (1) | BR0313790A (pt) |
CA (1) | CA2496563A1 (pt) |
DE (1) | DE10238865A1 (pt) |
EA (1) | EA012834B1 (pt) |
EC (1) | ECSP055615A (pt) |
HR (1) | HRP20050179A2 (pt) |
MX (1) | MXPA05002158A (pt) |
NO (1) | NO20050068L (pt) |
PE (1) | PE20040974A1 (pt) |
PL (1) | PL375344A1 (pt) |
RS (1) | RS20050173A (pt) |
TW (1) | TW200413332A (pt) |
UA (1) | UA82853C2 (pt) |
WO (1) | WO2004024702A1 (pt) |
ZA (1) | ZA200500086B (pt) |
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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 |
KR20060060047A (ko) | 2003-10-01 | 2006-06-02 | 더 프록터 앤드 갬블 캄파니 | 멜라닌 농축 호르몬 길항제 |
CA2541949A1 (en) * | 2003-10-07 | 2005-05-26 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
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 |
US7524862B2 (en) | 2004-04-14 | 2009-04-28 | Boehringer Ingelheim International Gmbh | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
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 |
WO2005115389A2 (en) * | 2004-05-25 | 2005-12-08 | Pfizer Products Inc. | Specific ppar agonists for treating negative energy balance |
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 |
PL1836169T3 (pl) * | 2004-12-28 | 2012-07-31 | Kinex Pharmaceuticals Llc | Kompozycje i sposoby leczenia zaburzeń związanych z proliferacją komórek |
US7968574B2 (en) | 2004-12-28 | 2011-06-28 | Kinex Pharmaceuticals, Llc | Biaryl compositions and methods for modulating a kinase cascade |
WO2007021309A1 (en) * | 2005-08-12 | 2007-02-22 | Astrazeneca Ab | Substituted isoindolones and their use as metabotropic glutamate receptor potentiators |
US7807706B2 (en) | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
RU2008129679A (ru) | 2005-12-21 | 2010-01-27 | Янссен Фармацевтика Н.В. (Be) | Новые замещенные пиразиноновые производные для применения при мсн-1-опосредованных заболеваниях |
TW200804347A (en) | 2006-01-10 | 2008-01-16 | Janssen Pharmaceutica Nv | Urotensin II receptor antagonists |
CA2636879A1 (en) * | 2006-02-15 | 2007-08-23 | Sanofi-Aventis | Novel amino alcohol-substituted arylthienopyrimidinones, process for their preparation and their use as medicaments |
BRPI0707836A2 (pt) | 2006-02-15 | 2011-05-10 | Sanofi Aventis | arildiidroisoquinolininas aminoÁlcool substituÍdas, processo para sua preparaÇço e seu uso como medicamento, medicamento e processo para sua produÇço |
CN101384583A (zh) * | 2006-02-15 | 2009-03-11 | 塞诺菲-安万特股份有限公司 | 氮杂环基-取代的芳基二氢异喹啉酮、它们的制备方法和它们作为药物的用途 |
BRPI0707869A2 (pt) * | 2006-02-15 | 2011-05-10 | Sanofi Aventis | ariltienopirimidinonas substituÍdas com azaciclil, processo para a sua preparaÇço e seus usos como medicamentos |
AU2007265373B2 (en) | 2006-06-29 | 2013-02-21 | Atnx Spv, Llc | Biaryl compositions and methods for modulating a kinase cascade |
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 |
WO2008016534A1 (en) | 2006-07-31 | 2008-02-07 | Janssen Pharmaceutica, N.V. | Urotensin ii receptor antagonists |
EP2383259A1 (en) | 2006-08-25 | 2011-11-02 | Boehringer Ingelheim International GmbH | New pyridone derivatives with MCH antagonistic activity and medicaments comprising these compounds |
CA2664112C (en) | 2006-12-05 | 2015-02-17 | Janssen Pharmaceutica N.V. | Novel substituted diaza-spiro-pyridinone derivatives for use in mch-1 mediated diseases |
CL2007003580A1 (es) | 2006-12-11 | 2009-03-27 | Boehringer Ingelheim Int | Compuestos derivados de piridazina, antagonistas de mch; composicion farmaceutica que comprende a dicho compuesto; procedimiento de preparacion; y uso del compuesto en el tratamiento de trastornos metabolicos y/o trastornos alimentarios como obesidad, bulimia, anorexia, hiperfagia, diabetes. |
US7935697B2 (en) | 2006-12-28 | 2011-05-03 | Kinex Pharmaceuticals, Llc | Compositions for modulating a kinase cascade and methods of use thereof |
JP2010514837A (ja) * | 2007-01-03 | 2010-05-06 | コーテックス ファーマシューティカルズ, インコーポレイテッド | グルタミン酸作動性シナプス反応を強化するための3−置換−[1,2,3]ベンゾトリアジノン化合物 |
DK2124562T3 (en) | 2007-03-09 | 2016-08-01 | Second Genome Inc | BICYCLOHETEROARYLFORBINDELSER 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 |
CN104016980B (zh) * | 2008-04-23 | 2016-12-07 | 里格尔药品股份有限公司 | 用于治疗代谢障碍的甲酰胺化合物 |
SA109300358B1 (ar) | 2008-06-06 | 2012-11-03 | استرازينيكا ايه بي | مقويات مستقبل جلوتامات ذي انتحاء أيضي من أيزو إندولون |
US9079896B2 (en) | 2008-08-02 | 2015-07-14 | Janssen Pharmaceutica Nv | Urotensin II receptor antagonists |
TW201040153A (en) | 2009-02-13 | 2010-11-16 | Sanofi Aventis | Novel substituted tetrahydronaphthalenes, process for preparation thereof and use thereof as medicaments |
AR075401A1 (es) | 2009-02-13 | 2011-03-30 | Sanofi Aventis | Indanos sustituidos, procesos para su preparacion y uso de los mismos como un medicamento |
CA2796419C (en) | 2010-04-16 | 2018-11-06 | Kinex Pharmaceuticals, Llc | Compositions and methods for the prevention and treatment of cancer |
GB201009853D0 (en) | 2010-06-11 | 2010-07-21 | Chroma Therapeutics Ltd | HSP90 inhibitors |
ES2785475T3 (es) * | 2011-05-10 | 2020-10-07 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores de canales iónicos |
NO3175985T3 (pt) | 2011-07-01 | 2018-04-28 | ||
UY34171A (es) | 2011-07-01 | 2013-01-31 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal iónico |
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 |
LT2890680T (lt) | 2012-08-30 | 2018-05-10 | Athenex, Inc. | N-(3-fluorbenzil-2-(5-(4-morfolinofenil)piridin-2-il)acetamidas, kaip proteintirozinkinazės moduliatorius |
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 |
JP2022549227A (ja) * | 2019-09-17 | 2022-11-24 | バイアル-アールアンドディー インベストメンツ ソシエダッド アノニマ | 医学的障害の治療における使用のための置換された飽和および不飽和n-複素環式カルボキサミドおよび関連化合物 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1218336A2 (en) * | 1999-09-20 | 2002-07-03 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
WO2001087834A1 (fr) * | 2000-05-16 | 2001-11-22 | Takeda Chemical Industries, Ltd. | Antagoniste de l'hormone de concentration de la melanine |
EP1299362A4 (en) * | 2000-07-05 | 2004-11-03 | Synaptic Pharma Corp | SELECTIVE RECEPTOR ANTAGONISTS OF MELANINE CONCENTRATING HORMON-1 (MCH1) AND THEIR USE |
US20030022891A1 (en) * | 2000-12-01 | 2003-01-30 | Anandan Palani | MCH antagonists and their use in the treatment of obesity |
CA2431953A1 (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 RS YUP-2005/0173A patent/RS20050173A/sr unknown
- 2003-08-16 CN CNA038200767A patent/CN1678591A/zh active Pending
- 2003-08-16 WO PCT/EP2003/009099 patent/WO2004024702A1/de active Application Filing
- 2003-08-16 CA CA002496563A patent/CA2496563A1/en not_active Abandoned
- 2003-08-16 JP JP2004535098A patent/JP2006507246A/ja active Pending
- 2003-08-16 AU AU2003258620A patent/AU2003258620A1/en not_active Abandoned
- 2003-08-16 EA EA200500301A patent/EA012834B1/ru not_active IP Right Cessation
- 2003-08-16 KR KR1020057003110A patent/KR20050040928A/ko not_active Application Discontinuation
- 2003-08-16 PL PL03375344A patent/PL375344A1/xx not_active Application Discontinuation
- 2003-08-16 EP EP03794886A patent/EP1534689A1/de not_active Withdrawn
- 2003-08-16 BR BR0313790-2A patent/BR0313790A/pt not_active Expired - Fee Related
- 2003-08-16 MX MXPA05002158A patent/MXPA05002158A/es unknown
- 2003-08-16 UA UAA200502601A patent/UA82853C2/uk unknown
- 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 |
---|---|
ECSP055615A (es) | 2005-05-30 |
CA2496563A1 (en) | 2004-03-25 |
KR20050040928A (ko) | 2005-05-03 |
BR0313790A (pt) | 2005-07-12 |
AU2003258620A1 (en) | 2004-04-30 |
DE10238865A1 (de) | 2004-03-11 |
EP1534689A1 (de) | 2005-06-01 |
ZA200500086B (en) | 2006-07-26 |
JP2006507246A (ja) | 2006-03-02 |
AR043046A1 (es) | 2005-07-13 |
HRP20050179A2 (en) | 2006-05-31 |
MXPA05002158A (es) | 2005-05-23 |
EA200500301A1 (ru) | 2006-02-24 |
EA012834B1 (ru) | 2009-12-30 |
RS20050173A (en) | 2007-09-21 |
CN1678591A (zh) | 2005-10-05 |
PL375344A1 (en) | 2005-11-28 |
NO20050068L (no) | 2005-03-04 |
WO2004024702A1 (de) | 2004-03-25 |
TW200413332A (en) | 2004-08-01 |
PE20040974A1 (es) | 2005-01-12 |
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