ZA200006529B - Novel substituted cyclic compounds, preparation method and pharmaceutical compositions containing them. - Google Patents
Novel substituted cyclic compounds, preparation method and pharmaceutical compositions containing them. Download PDFInfo
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- ZA200006529B ZA200006529B ZA200006529A ZA200006529A ZA200006529B ZA 200006529 B ZA200006529 B ZA 200006529B ZA 200006529 A ZA200006529 A ZA 200006529A ZA 200006529 A ZA200006529 A ZA 200006529A ZA 200006529 B ZA200006529 B ZA 200006529B
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- ZA
- South Africa
- Prior art keywords
- formula
- group
- compounds
- substituted
- pharmaceutically acceptable
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000001923 cyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 170
- 239000002253 acid Substances 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 75
- 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 72
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000004122 cyclic group Chemical group 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- -1 cyano, carboxy, nitro, amino Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 16
- 239000005864 Sulphur Substances 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 125000003367 polycyclic group Polymers 0.000 claims description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 7
- 125000006267 biphenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000002475 indoles Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 claims description 5
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
- 230000001193 melatoninergic effect Effects 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 230000014509 gene expression Effects 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- 150000003222 pyridines Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- STSHBXBCKMTFLA-UHFFFAOYSA-N n-[2-[7-(ethylsulfamoyl)naphthalen-1-yl]ethyl]benzamide Chemical compound C12=CC(S(=O)(=O)NCC)=CC=C2C=CC=C1CCNC(=O)C1=CC=CC=C1 STSHBXBCKMTFLA-UHFFFAOYSA-N 0.000 claims description 2
- SUSDQVARBLWNKJ-UHFFFAOYSA-N n-[3-(2-acetamidoethyl)-1-benzofuran-5-yl]-2,2,2-trifluoroacetamide Chemical compound C1=C(NC(=O)C(F)(F)F)C=C2C(CCNC(=O)C)=COC2=C1 SUSDQVARBLWNKJ-UHFFFAOYSA-N 0.000 claims description 2
- GNUQAUBMPNTEQQ-UHFFFAOYSA-N n-[8-(acetamidomethyl)naphthalen-2-yl]-2-methylpropanamide Chemical compound C1=CC=C(CNC(C)=O)C2=CC(NC(=O)C(C)C)=CC=C21 GNUQAUBMPNTEQQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims 18
- 239000003795 chemical substances by application Substances 0.000 claims 6
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims 4
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical class C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 claims 4
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 4
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 claims 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 3
- 150000001263 acyl chlorides Chemical class 0.000 claims 3
- 150000008064 anhydrides Chemical class 0.000 claims 3
- 239000007858 starting material Substances 0.000 claims 3
- 150000001540 azides Chemical class 0.000 claims 2
- 125000005605 benzo group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- VIEBSWGQQLTIQK-UHFFFAOYSA-N 3-(2-acetamidoethyl)-1-benzofuran-5-carboxamide Chemical compound C1=C(C(N)=O)C=C2C(CCNC(=O)C)=COC2=C1 VIEBSWGQQLTIQK-UHFFFAOYSA-N 0.000 claims 1
- FGUNVBUATYZLQB-UHFFFAOYSA-N 3-(2-acetamidoethyl)-n-methyl-1-benzofuran-5-carboxamide Chemical compound CNC(=O)C1=CC=C2OC=C(CCNC(C)=O)C2=C1 FGUNVBUATYZLQB-UHFFFAOYSA-N 0.000 claims 1
- LJLMSSPJRKZNDS-UHFFFAOYSA-N 3-(2-benzamidoethyl)-1-benzofuran-5-carboxamide Chemical compound C12=CC(C(=O)N)=CC=C2OC=C1CCNC(=O)C1=CC=CC=C1 LJLMSSPJRKZNDS-UHFFFAOYSA-N 0.000 claims 1
- FHNYMXTZNBYGGU-UHFFFAOYSA-N 3-(2-benzamidoethyl)-n-ethyl-1-benzofuran-5-carboxamide Chemical compound C12=CC(C(=O)NCC)=CC=C2OC=C1CCNC(=O)C1=CC=CC=C1 FHNYMXTZNBYGGU-UHFFFAOYSA-N 0.000 claims 1
- QKDSCYPFRPNVIJ-UHFFFAOYSA-N 3-(2-benzamidoethyl)-n-methyl-1-benzofuran-5-carboxamide Chemical compound C12=CC(C(=O)NC)=CC=C2OC=C1CCNC(=O)C1=CC=CC=C1 QKDSCYPFRPNVIJ-UHFFFAOYSA-N 0.000 claims 1
- NGXHGMQVPFQMFQ-UHFFFAOYSA-N 3-[2-(cyclopentanecarbonylamino)ethyl]-n-methyl-1-benzofuran-5-carboxamide Chemical compound C12=CC(C(=O)NC)=CC=C2OC=C1CCNC(=O)C1CCCC1 NGXHGMQVPFQMFQ-UHFFFAOYSA-N 0.000 claims 1
- JJSYMZXVGUMILK-UHFFFAOYSA-N 3-[2-(cyclopropanecarbonylamino)ethyl]-1-benzofuran-5-carboxamide Chemical compound C12=CC(C(=O)N)=CC=C2OC=C1CCNC(=O)C1CC1 JJSYMZXVGUMILK-UHFFFAOYSA-N 0.000 claims 1
- BFROOJUQXPJWQV-UHFFFAOYSA-N 3-[2-(cyclopropanecarbonylamino)ethyl]-n-ethyl-1-benzofuran-5-carboxamide Chemical compound C12=CC(C(=O)NCC)=CC=C2OC=C1CCNC(=O)C1CC1 BFROOJUQXPJWQV-UHFFFAOYSA-N 0.000 claims 1
- HPNFNZLUXKUCMM-UHFFFAOYSA-N 3-[2-(cyclopropanecarbonylamino)ethyl]-n-methyl-1-benzofuran-5-carboxamide Chemical compound C12=CC(C(=O)NC)=CC=C2OC=C1CCNC(=O)C1CC1 HPNFNZLUXKUCMM-UHFFFAOYSA-N 0.000 claims 1
- XSVQVVXJSFYREP-UHFFFAOYSA-N 3-[2-(furan-2-carbonylamino)ethyl]-1-benzofuran-5-carboxamide Chemical compound C12=CC(C(=O)N)=CC=C2OC=C1CCNC(=O)C1=CC=CO1 XSVQVVXJSFYREP-UHFFFAOYSA-N 0.000 claims 1
- SRNXYTCFHFUHFG-UHFFFAOYSA-N 8-[2-[methyl(propylcarbamoyl)amino]ethyl]-n-phenylnaphthalene-2-carboxamide Chemical compound C1=C2C(CCN(C)C(=O)NCCC)=CC=CC2=CC=C1C(=O)NC1=CC=CC=C1 SRNXYTCFHFUHFG-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 101100323029 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alc-1 gene Proteins 0.000 claims 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims 1
- 229910002056 binary alloy Inorganic materials 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 230000017858 demethylation Effects 0.000 claims 1
- 238000010520 demethylation reaction Methods 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- QWETUAVEDNSMMU-UHFFFAOYSA-N ethyl n-[3-(2-acetamidoethyl)-2,3-dihydro-1h-inden-5-yl]carbamate Chemical group CCOC(=O)NC1=CC=C2CCC(CCNC(C)=O)C2=C1 QWETUAVEDNSMMU-UHFFFAOYSA-N 0.000 claims 1
- QOSYUBJFWXZYIK-UHFFFAOYSA-N ethyl n-[8-[2-[(2-bromoacetyl)amino]ethyl]naphthalen-2-yl]carbamate Chemical compound C1=CC=C(CCNC(=O)CBr)C2=CC(NC(=O)OCC)=CC=C21 QOSYUBJFWXZYIK-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 238000006138 lithiation reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OWRQGIILOGWMKK-UHFFFAOYSA-N methyl 3-(2-benzamidoethyl)-1-benzofuran-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2OC=C1CCNC(=O)C1=CC=CC=C1 OWRQGIILOGWMKK-UHFFFAOYSA-N 0.000 claims 1
- FLAWKNVNRSLTFM-UHFFFAOYSA-N methyl 3-[2-(2-methylpropylamino)ethyl]-1-benzofuran-5-carboxylate Chemical compound COC(=O)C1=CC=C2OC=C(CCNCC(C)C)C2=C1 FLAWKNVNRSLTFM-UHFFFAOYSA-N 0.000 claims 1
- WLSXCCSVAWMDJD-UHFFFAOYSA-N methyl 3-[2-(but-3-enoylamino)ethyl]-1-benzofuran-5-carboxylate Chemical compound COC(=O)C1=CC=C2OC=C(CCNC(=O)CC=C)C2=C1 WLSXCCSVAWMDJD-UHFFFAOYSA-N 0.000 claims 1
- CUUQICZMRYXTLF-UHFFFAOYSA-N methyl 3-[2-(cyclopentanecarbonylamino)ethyl]-1-benzofuran-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2OC=C1CCNC(=O)C1CCCC1 CUUQICZMRYXTLF-UHFFFAOYSA-N 0.000 claims 1
- LCDXMAJZSYFXNU-UHFFFAOYSA-N methyl 3-[2-(cyclopropanecarbonylamino)ethyl]-1-benzofuran-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2OC=C1CCNC(=O)C1CC1 LCDXMAJZSYFXNU-UHFFFAOYSA-N 0.000 claims 1
- NIGQQTBPLPXWSP-UHFFFAOYSA-N methyl 3-[2-(furan-2-carbonylamino)ethyl]-1-benzofuran-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2OC=C1CCNC(=O)C1=CC=CO1 NIGQQTBPLPXWSP-UHFFFAOYSA-N 0.000 claims 1
- YNHBPUMTCUKQHD-UHFFFAOYSA-N methyl n-[3-(2-benzamidoethyl)-1-benzofuran-5-yl]carbamate Chemical compound C12=CC(NC(=O)OC)=CC=C2OC=C1CCNC(=O)C1=CC=CC=C1 YNHBPUMTCUKQHD-UHFFFAOYSA-N 0.000 claims 1
- MUPLLDUULDSAQJ-UHFFFAOYSA-N methyl n-[3-(acetamidomethyl)-3,4-dihydro-2h-chromen-6-yl]carbamate Chemical group O1CC(CNC(C)=O)CC2=CC(NC(=O)OC)=CC=C21 MUPLLDUULDSAQJ-UHFFFAOYSA-N 0.000 claims 1
- CQWNTRFWWAONMJ-UHFFFAOYSA-N methyl n-[3-[2-(2-methylpropanoylamino)ethyl]-1-benzofuran-5-yl]carbamate Chemical compound COC(=O)NC1=CC=C2OC=C(CCNC(=O)C(C)C)C2=C1 CQWNTRFWWAONMJ-UHFFFAOYSA-N 0.000 claims 1
- WPUVYHBPRBDQLZ-UHFFFAOYSA-N methyl n-[3-[2-(cyclopentanecarbonylamino)ethyl]-1-benzofuran-5-yl]carbamate Chemical compound C12=CC(NC(=O)OC)=CC=C2OC=C1CCNC(=O)C1CCCC1 WPUVYHBPRBDQLZ-UHFFFAOYSA-N 0.000 claims 1
- KYSCWFKYUJDVHS-UHFFFAOYSA-N methyl n-[3-[2-(cyclopropanecarbonylamino)ethyl]-1-benzofuran-5-yl]carbamate Chemical compound C12=CC(NC(=O)OC)=CC=C2OC=C1CCNC(=O)C1CC1 KYSCWFKYUJDVHS-UHFFFAOYSA-N 0.000 claims 1
- VFPAHXTUSUVJEM-UHFFFAOYSA-N methyl n-[3-[2-(furan-2-carbonylamino)ethyl]-1-benzofuran-5-yl]carbamate Chemical compound C12=CC(NC(=O)OC)=CC=C2OC=C1CCNC(=O)C1=CC=CO1 VFPAHXTUSUVJEM-UHFFFAOYSA-N 0.000 claims 1
- SHZBHGJUHWSBAF-UHFFFAOYSA-N methyl n-[8-(2-acetamidoethyl)naphthalen-2-yl]carbamate Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(NC(=O)OC)=CC=C21 SHZBHGJUHWSBAF-UHFFFAOYSA-N 0.000 claims 1
- GCBBVRLFMIQTAY-UHFFFAOYSA-N n-[2-(5-acetamido-1-benzofuran-3-yl)ethyl]cyclopropanecarboxamide Chemical compound C12=CC(NC(=O)C)=CC=C2OC=C1CCNC(=O)C1CC1 GCBBVRLFMIQTAY-UHFFFAOYSA-N 0.000 claims 1
- UZFMTPZFMOXXAE-UHFFFAOYSA-N n-[2-(5-acetamido-1-benzothiophen-3-yl)ethyl]benzamide Chemical compound C12=CC(NC(=O)C)=CC=C2SC=C1CCNC(=O)C1=CC=CC=C1 UZFMTPZFMOXXAE-UHFFFAOYSA-N 0.000 claims 1
- HUSHLBGTHCPYEJ-UHFFFAOYSA-N n-[2-(6-acetamido-2,3-dihydro-1h-inden-1-yl)ethyl]acetamide Chemical group C1=C(NC(C)=O)C=C2C(CCNC(=O)C)CCC2=C1 HUSHLBGTHCPYEJ-UHFFFAOYSA-N 0.000 claims 1
- TXEOZOYTOBMLJS-UHFFFAOYSA-N n-[2-(7-acetamidonaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C(NC(C)=O)C=C2C(CCNC(=O)C)=CC=CC2=C1 TXEOZOYTOBMLJS-UHFFFAOYSA-N 0.000 claims 1
- VUCSLISILBVLDV-UHFFFAOYSA-N n-[2-(7-sulfamoylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C(S(N)(=O)=O)C=C2C(CCNC(=O)C)=CC=CC2=C1 VUCSLISILBVLDV-UHFFFAOYSA-N 0.000 claims 1
- OPDMHFFABBXHHY-UHFFFAOYSA-N n-[2-[2-benzyl-5-(methylsulfamoyl)-1-benzothiophen-3-yl]ethyl]acetamide Chemical compound CC(=O)NCCC=1C2=CC(S(=O)(=O)NC)=CC=C2SC=1CC1=CC=CC=C1 OPDMHFFABBXHHY-UHFFFAOYSA-N 0.000 claims 1
- XLFVNRCXTJVXLZ-UHFFFAOYSA-N n-[2-[5-(cyclopropylsulfamoyl)-1-benzofuran-3-yl]ethyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCC(C1=C2)=COC1=CC=C2S(=O)(=O)NC1CC1 XLFVNRCXTJVXLZ-UHFFFAOYSA-N 0.000 claims 1
- ZPZCORKPVQDFIR-UHFFFAOYSA-N n-[2-[5-(methylsulfamoyl)-1-benzofuran-3-yl]ethyl]cyclopropanecarboxamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2OC=C1CCNC(=O)C1CC1 ZPZCORKPVQDFIR-UHFFFAOYSA-N 0.000 claims 1
- FHDPYJAEZVYUGP-UHFFFAOYSA-N n-[2-[5-(methylsulfamoyl)-1-benzofuran-3-yl]ethyl]furan-2-carboxamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2OC=C1CCNC(=O)C1=CC=CO1 FHDPYJAEZVYUGP-UHFFFAOYSA-N 0.000 claims 1
- BWGVRCMWDBJXQM-UHFFFAOYSA-N n-[2-[5-(methylsulfamoyl)-1h-pyrrolo[2,3-b]pyridin-3-yl]ethyl]acetamide Chemical compound CNS(=O)(=O)C1=CN=C2NC=C(CCNC(C)=O)C2=C1 BWGVRCMWDBJXQM-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/74—Naphthothiophenes
-
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
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- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
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- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
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-
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- C07D495/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Ceramic Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Reproductive Health (AREA)
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- Hematology (AREA)
- Gynecology & Obstetrics (AREA)
- Emergency Medicine (AREA)
- Anesthesiology (AREA)
- Pregnancy & Childbirth (AREA)
- Psychology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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FR9805957A FR2778662B1 (fr) | 1998-05-12 | 1998-05-12 | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
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ZA200006529B true ZA200006529B (en) | 2001-05-22 |
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ZA200006529A ZA200006529B (en) | 1998-05-12 | 2000-11-10 | Novel substituted cyclic compounds, preparation method and pharmaceutical compositions containing them. |
ZA200006528A ZA200006528B (en) | 1998-05-12 | 2000-11-10 | Novel substituted cyclic compounds, preparation method and pharmaceutical compositions containing them. |
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ZA200006528A ZA200006528B (en) | 1998-05-12 | 2000-11-10 | Novel substituted cyclic compounds, preparation method and pharmaceutical compositions containing them. |
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US (6) | US6605632B1 (pt) |
EP (2) | EP1077928B1 (pt) |
JP (2) | JP2002514619A (pt) |
CN (2) | CN1304400A (pt) |
AT (2) | ATE312073T1 (pt) |
AU (2) | AU747301B2 (pt) |
BR (2) | BR9911783A (pt) |
CA (2) | CA2331877C (pt) |
DE (2) | DE69933149T2 (pt) |
DK (2) | DK1077928T3 (pt) |
ES (2) | ES2255260T3 (pt) |
FR (1) | FR2778662B1 (pt) |
HU (2) | HUP0101813A3 (pt) |
NO (2) | NO20005714D0 (pt) |
NZ (2) | NZ507691A (pt) |
PL (2) | PL195613B1 (pt) |
WO (2) | WO1999058496A1 (pt) |
ZA (2) | ZA200006529B (pt) |
Families Citing this family (45)
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AUPO274596A0 (en) * | 1996-10-04 | 1996-10-31 | Armstrong, Stuart Maxwell | Method for the treatment of neurological or neuropsychiatric disorders |
FR2778662B1 (fr) * | 1998-05-12 | 2000-06-16 | Adir | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
US6569879B2 (en) * | 2000-02-18 | 2003-05-27 | Merck & Co., Inc. | Aryloxyacetic acids for diabetes and lipid disorders |
FR2814165B1 (fr) * | 2000-09-15 | 2002-11-22 | Adir | Nouveaux derives biphenyles substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
CZ20031910A3 (cs) | 2000-12-11 | 2003-12-17 | Tularik Inc. | Sloučenina s antagonistickými účinky na CXCR3 a farmaceutický postředek |
US6794379B2 (en) * | 2001-06-06 | 2004-09-21 | Tularik Inc. | CXCR3 antagonists |
FR2853649B1 (fr) * | 2003-04-09 | 2006-07-14 | Servier Lab | Nouveaux derives d'isoquinoleine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
FR2857011B1 (fr) * | 2003-07-04 | 2005-09-16 | Servier Lab | Nouveaux derives du benzothiophene 2-thiosubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
GB0330043D0 (en) | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions comprising them |
GB0330042D0 (en) | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions them |
DE602005019562D1 (de) * | 2004-05-05 | 2010-04-08 | Hoffmann La Roche | Zur modulation des 5-ht6-rezeptors, des 5-ht2a-rezeptors oder beider rezeptoren geeignete arylsulfonylbenzodioxane |
WO2006019497A2 (en) * | 2004-06-17 | 2006-02-23 | Neurocrine Biosciences, Inc. | Sleep-inducing compounds and methods related thereto |
US7375102B2 (en) | 2004-06-28 | 2008-05-20 | Amgen Sf, Llc | Tetrahydroquinazolin-4(3H)-one-related and tetrahydropyrido[2,3-D]pyrimidin-4(3H)-one-related compounds, compositions and methods for their use |
US7271271B2 (en) | 2004-06-28 | 2007-09-18 | Amgen Sf, Llc | Imidazolo-related compounds, compositions and methods for their use |
US7939538B2 (en) | 2004-06-28 | 2011-05-10 | Amgen Inc. | Compounds, compositions and methods for prevention and treatment of inflammatory and immunoregulatory disorders and diseases |
SI1831159T1 (sl) * | 2004-12-21 | 2010-04-30 | Hoffmann La Roche | Derivati tetralina in indana ter njune uporabe |
EP1831152B1 (en) * | 2004-12-21 | 2008-09-24 | F. Hoffmann-La Roche AG | Tetralin and indane derivatives and uses thereof as 5-ht antagonists |
WO2006066756A1 (en) | 2004-12-21 | 2006-06-29 | F. Hoffmann-La Roche Ag | Chroman derivatives and uses thereof in the treatment of cns disorders |
JP2008524275A (ja) * | 2004-12-21 | 2008-07-10 | エフ.ホフマン−ラ ロシュ アーゲー | クロマン誘導体及び5−htレセプターリガンドとしてのそれらの使用 |
CA2591793A1 (en) | 2004-12-21 | 2006-06-29 | F. Hoffmann-La Roche Ag | Tetralin and indane derivatives and uses thereof |
KR100984897B1 (ko) * | 2005-11-03 | 2010-10-01 | 에프. 호프만-라 로슈 아게 | 5-ht6 억제제로서 아릴설포닐 크로만 |
WO2007067257A2 (en) | 2005-12-02 | 2007-06-14 | Vanderbilt University | Broad-emission nanocrystals and methods of making and using same |
CA2641744C (en) * | 2006-02-10 | 2012-09-25 | Transtech Pharma, Inc. | Benzazole derivatives, compositions, and methods of use as aurora kinase inhibitors |
JP2009541248A (ja) * | 2006-06-20 | 2009-11-26 | エフ.ホフマン−ラ ロシュ アーゲー | アリールスルホンアミジルテトラリン誘導体及びそれらの使用 |
JP2009541252A (ja) * | 2006-06-20 | 2009-11-26 | エフ.ホフマン−ラ ロシュ アーゲー | テトラリン及びインダン誘導体ならびにそれらの使用 |
JP2009541249A (ja) | 2006-06-20 | 2009-11-26 | エフ.ホフマン−ラ ロシュ アーゲー | アリールスルホニルナフタレン誘導体およびその使用 |
CA2701115A1 (en) * | 2007-10-04 | 2009-04-09 | Merck Sharp & Dohme Corp. | N-hydroxy-naphthalene dicarboxamide and n-hydroxy-biphenyl-dicarboxamide compounds as histone deacetylase inhibitors |
ATE533752T1 (de) | 2008-09-08 | 2011-12-15 | Cadila Pharmaceuticals Ltd | Verbesserter herstellungsprozess für nebivolol- hydrocholorid |
CN101481321B (zh) * | 2009-02-27 | 2012-04-18 | 上海医药工业研究院 | 阿戈美拉汀卤化氢复合物及其制备方法 |
EP3102576B8 (en) | 2014-02-03 | 2019-06-19 | Vitae Pharmaceuticals, LLC | Dihydropyrrolopyridine inhibitors of ror-gamma |
CN104292125B (zh) * | 2014-08-14 | 2016-06-01 | 广东东阳光药业有限公司 | 萘衍生物及其在药物上的应用 |
PT3207043T (pt) | 2014-10-14 | 2019-03-25 | Vitae Pharmaceuticals Llc | Inibidores de di-hidropirrolopiridina de ror-gama |
US9845308B2 (en) | 2014-11-05 | 2017-12-19 | Vitae Pharmaceuticals, Inc. | Isoindoline inhibitors of ROR-gamma |
US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
JP2018502889A (ja) | 2015-01-20 | 2018-02-01 | エックスオーシー ファーマシューティカルズ インコーポレイテッドXoc Pharmaceuticals, Inc | イソエルゴリン化合物およびその使用 |
BR112017015487A2 (pt) * | 2015-01-20 | 2018-01-30 | Xoc Pharmaceuticals Inc | Composto; composição; método de tratamento e/ou prevenção de enxaqueca, als, doença de alzheimer, doença de parkinson, distúrbios extrapirimidais, depressão, náusea, êmese, síndrome das pernas inquietas, insônia, agressão, doença de huntington, doença cardiopulmonar, fibrogênese, hipertensão arterial pulmonar, ansiedade, dependências a drogas, distonia, parassonia ou hiperlactinemia em um indivíduo; métodos de agonização dos receptores d2, 5-ht1d, 5-ht1a e 5-ht2c, em um indivíduo; método de antagonização do receptor d3 em um indivíduo; métodos de agonização seletiva dos receptores 5 -ht1d, e 5-ht2c, método de fornecimento de atividade de antagonista funcional no receptor 5 -ht2b ou no receptor 5-ht7, ou em ambos, em um indivíduo; método de fornecimento de atividade de antagonista funcional nos receptores adrenérgicos em um indivíduo |
US10301261B2 (en) | 2015-08-05 | 2019-05-28 | Vitae Pharmaceuticals, Llc | Substituted indoles as modulators of ROR-gamma |
MA53943A (fr) | 2015-11-20 | 2021-08-25 | Vitae Pharmaceuticals Llc | Modulateurs de ror-gamma |
TW202220968A (zh) | 2016-01-29 | 2022-06-01 | 美商維它藥物有限責任公司 | ROR-γ調節劑 |
US9481674B1 (en) | 2016-06-10 | 2016-11-01 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
WO2018223065A1 (en) | 2017-06-01 | 2018-12-06 | Xoc Pharmaceuticals, Inc. | Ergoline derivatives for use in medicine |
AU2018307919B2 (en) | 2017-07-24 | 2022-12-01 | Vitae Pharmaceuticals, Llc | Inhibitors of RORϒ |
WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
CN108156986A (zh) * | 2018-01-04 | 2018-06-15 | 山东农业大学 | 外源褪黑素对苹果矮化自根砧木幼苗臭氧胁迫缓解效应的应用 |
CR20230576A (es) | 2021-06-14 | 2024-04-05 | Scorpion Therapeutics Inc | Derivados de la urea que pueden ser utilizados para tratar el cáncer |
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US4663347A (en) * | 1983-10-31 | 1987-05-05 | Merck Frosst Canada, Inc. | Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis |
FR2680507B1 (fr) * | 1991-08-23 | 1993-10-08 | Adir Cie | Nouvelles naphtylethylurees et naphtylethylthiourees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
FR2689124A1 (fr) * | 1992-03-27 | 1993-10-01 | Adir | Nouvelles naphtylalkylamines, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
FR2705095B1 (fr) * | 1993-05-12 | 1995-06-23 | Adir | Nouveaux indoles substitués, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
GB9313913D0 (en) * | 1993-07-06 | 1993-08-18 | Smithkline Beecham Plc | Novel compounds |
US5350748A (en) * | 1993-08-18 | 1994-09-27 | Warner-Lambert Company | 3-thio or amino substituted-benzo[b]thiophene-2-carboxamides and 3-oxygen, thio, or amino substituted-benzofuran-2-carboxamides as inhibitors of cell adhesion |
FR2713636B1 (fr) * | 1993-12-07 | 1996-01-05 | Adir | Nouveaux dérivés naphtaléniques, leur procédé de préparation, et les compositions pharmaceutiques qui les contiennent. |
WO1996008466A1 (en) * | 1994-09-12 | 1996-03-21 | Takeda Chemical Industries, Ltd. | Benzocycloalkene compounds, their production and use |
JPH08268987A (ja) * | 1995-02-24 | 1996-10-15 | Bristol Myers Squibb Co | テトラリニル−,及びインダニル−エチルアミド誘導体 |
US5863936A (en) * | 1995-04-18 | 1999-01-26 | Geron Corporation | Telomerase inhibitors |
FR2734815B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes arylalkyl (thio) carboxamides, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
FR2734814B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes alkoxy-aryles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
DE69620458T2 (de) * | 1995-12-05 | 2002-10-02 | Darwin Discovery Ltd., Cambridge | Benzofuran-carboxamide und -sulfonamide |
FR2778662B1 (fr) * | 1998-05-12 | 2000-06-16 | Adir | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
KR101012391B1 (ko) | 2008-11-11 | 2011-02-09 | 엘지전자 주식회사 | 무선 통신 시스템에 있어서, 하향링크로 서브프레임 지정 정보를 전송하는 방법 |
-
1998
- 1998-05-12 FR FR9805957A patent/FR2778662B1/fr not_active Expired - Fee Related
-
1999
- 1999-05-10 ES ES99918036T patent/ES2255260T3/es not_active Expired - Lifetime
- 1999-05-10 DK DK99918037T patent/DK1077928T3/da active
- 1999-05-10 AU AU36104/99A patent/AU747301B2/en not_active Ceased
- 1999-05-10 EP EP99918037A patent/EP1077928B1/fr not_active Expired - Lifetime
- 1999-05-10 CN CN99806830A patent/CN1304400A/zh active Pending
- 1999-05-10 AT AT99918037T patent/ATE312073T1/de not_active IP Right Cessation
- 1999-05-10 NZ NZ507691A patent/NZ507691A/en unknown
- 1999-05-10 HU HU0101813A patent/HUP0101813A3/hu unknown
- 1999-05-10 CA CA002331877A patent/CA2331877C/fr not_active Expired - Fee Related
- 1999-05-10 WO PCT/FR1999/001101 patent/WO1999058496A1/fr active IP Right Grant
- 1999-05-10 AT AT99918036T patent/ATE312072T1/de not_active IP Right Cessation
- 1999-05-10 BR BR9911783-5A patent/BR9911783A/pt not_active Application Discontinuation
- 1999-05-10 DE DE69933149T patent/DE69933149T2/de not_active Expired - Fee Related
- 1999-05-10 AU AU36103/99A patent/AU748567B2/en not_active Ceased
- 1999-05-10 ES ES99918037T patent/ES2255261T3/es not_active Expired - Lifetime
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- 1999-05-10 US US09/700,056 patent/US6605632B1/en not_active Expired - Fee Related
- 1999-05-10 BR BR9911771-1A patent/BR9911771A/pt not_active Application Discontinuation
- 1999-05-10 NZ NZ507692A patent/NZ507692A/en unknown
- 1999-05-10 DK DK99918036T patent/DK1077927T3/da active
- 1999-05-10 HU HU0101800A patent/HUP0101800A3/hu unknown
- 1999-05-10 EP EP99918036A patent/EP1077927B1/fr not_active Expired - Lifetime
- 1999-05-10 PL PL99344048A patent/PL195613B1/pl unknown
- 1999-05-10 WO PCT/FR1999/001100 patent/WO1999058495A1/fr active IP Right Grant
- 1999-05-10 US US09/700,098 patent/US6872851B1/en not_active Expired - Fee Related
- 1999-05-10 CN CN99806053A patent/CN1300277A/zh active Pending
- 1999-05-10 CA CA002331870A patent/CA2331870C/fr not_active Expired - Fee Related
- 1999-05-10 PL PL99344012A patent/PL344012A1/xx unknown
- 1999-05-10 JP JP2000548300A patent/JP2002514620A/ja active Pending
- 1999-05-10 DE DE69933147T patent/DE69933147T2/de not_active Expired - Fee Related
-
2000
- 2000-11-10 ZA ZA200006529A patent/ZA200006529B/en unknown
- 2000-11-10 ZA ZA200006528A patent/ZA200006528B/en unknown
- 2000-11-13 NO NO20005714A patent/NO20005714D0/no not_active Application Discontinuation
- 2000-11-13 NO NO20005715A patent/NO20005715D0/no not_active Application Discontinuation
-
2003
- 2003-06-16 US US10/462,326 patent/US20040002490A1/en not_active Abandoned
- 2003-06-16 US US10/462,331 patent/US7183318B2/en not_active Expired - Fee Related
-
2004
- 2004-09-23 US US10/948,410 patent/US7115752B2/en not_active Expired - Fee Related
- 2004-09-23 US US10/947,757 patent/US7126012B2/en not_active Expired - Fee Related
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