NZ507692A - Retroamide chain benzofuran and benzothiophene compounds substituted by amides or carbamates for use in melatonergic system disorders - Google Patents
Retroamide chain benzofuran and benzothiophene compounds substituted by amides or carbamates for use in melatonergic system disordersInfo
- Publication number
- NZ507692A NZ507692A NZ507692A NZ50769299A NZ507692A NZ 507692 A NZ507692 A NZ 507692A NZ 507692 A NZ507692 A NZ 507692A NZ 50769299 A NZ50769299 A NZ 50769299A NZ 507692 A NZ507692 A NZ 507692A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- group
- compounds
- ethyl
- substituted
- Prior art date
Links
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title claims description 18
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title claims description 15
- 150000001408 amides Chemical group 0.000 title description 5
- 150000004657 carbamic acid derivatives Chemical group 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 337
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims description 445
- 239000007858 starting material Substances 0.000 claims description 217
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 167
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 134
- 238000000034 method Methods 0.000 claims description 84
- 239000002253 acid Substances 0.000 claims description 81
- 150000003839 salts Chemical class 0.000 claims description 74
- 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 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 60
- 125000004122 cyclic group Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 230000009471 action Effects 0.000 claims description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- -1 cyano, carboxy, nitro, amino Chemical group 0.000 claims description 36
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 33
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 18
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 239000005864 Sulphur Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 10
- 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 description 10
- 230000001193 melatoninergic effect Effects 0.000 claims description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 238000012360 testing method Methods 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 241000700159 Rattus Species 0.000 claims description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 8
- 125000005605 benzo group Chemical group 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000003367 polycyclic group Polymers 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 7
- 150000001540 azides Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001263 acyl chlorides Chemical class 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004366 heterocycloalkenyl 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
- 210000001367 artery Anatomy 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 5
- 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 description 4
- 229910015845 BBr3 Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000014509 gene expression Effects 0.000 claims description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003446 ligand Substances 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
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 150000003222 pyridines Chemical group 0.000 claims description 4
- 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 description 3
- 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 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 3
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 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 description 3
- VNBHAJFCYIDHKM-UHFFFAOYSA-N hexyl n-[8-(2-acetamidoethyl)-5,6,7,8-tetrahydronaphthalen-2-yl]carbamate Chemical compound C1CCC(CCNC(C)=O)C2=CC(NC(=O)OCCCCCC)=CC=C21 VNBHAJFCYIDHKM-UHFFFAOYSA-N 0.000 claims description 3
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- ZMQJWTSYMGTHFB-UHFFFAOYSA-N n-[2-[7-(methylsulfamoyl)naphthalen-1-yl]ethyl]furan-2-carboxamide Chemical compound C12=CC(S(=O)(=O)NC)=CC=C2C=CC=C1CCNC(=O)C1=CC=CO1 ZMQJWTSYMGTHFB-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- ZZSRQWOPFCQAGD-UHFFFAOYSA-N n-[8-[2-[(2-phenylacetyl)amino]ethyl]naphthalen-2-yl]butanamide Chemical compound C12=CC(NC(=O)CCC)=CC=C2C=CC=C1CCNC(=O)CC1=CC=CC=C1 ZZSRQWOPFCQAGD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- CKDITILKVSNWTR-UHFFFAOYSA-N tert-butyl n-[3-(2-acetamidoethyl)-1-benzofuran-5-yl]carbamate Chemical compound C1=C(NC(=O)OC(C)(C)C)C=C2C(CCNC(=O)C)=COC2=C1 CKDITILKVSNWTR-UHFFFAOYSA-N 0.000 claims description 3
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 229910019213 POCl3 Inorganic materials 0.000 claims description 2
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 claims description 2
- 238000007239 Wittig reaction Methods 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 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
- 229910002056 binary alloy Inorganic materials 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 239000007822 coupling agent Substances 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
- 230000017858 demethylation Effects 0.000 claims description 2
- 238000010520 demethylation reaction Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 230000022244 formylation Effects 0.000 claims description 2
- 238000006170 formylation reaction Methods 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
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 238000006138 lithiation reaction Methods 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- BGFIBWAZAGTWQA-UHFFFAOYSA-N methyl n-[8-(2-acetamidoethyl)-6-phenylnaphthalen-2-yl]carbamate Chemical compound C1=C(CCNC(C)=O)C2=CC(NC(=O)OC)=CC=C2C=C1C1=CC=CC=C1 BGFIBWAZAGTWQA-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- OYEDEXQOJRFSLF-UHFFFAOYSA-N n-[2-[5-(propylsulfamoyl)-1-benzofuran-3-yl]ethyl]acetamide Chemical compound CCCNS(=O)(=O)C1=CC=C2OC=C(CCNC(C)=O)C2=C1 OYEDEXQOJRFSLF-UHFFFAOYSA-N 0.000 claims description 2
- DVBNKCFZJHHJTL-UHFFFAOYSA-N n-[2-[7-(methylcarbamoyl)naphthalen-1-yl]ethyl]furan-2-carboxamide Chemical compound C12=CC(C(=O)NC)=CC=C2C=CC=C1CCNC(=O)C1=CC=CO1 DVBNKCFZJHHJTL-UHFFFAOYSA-N 0.000 claims description 2
- LMMCCCKILDSFAH-UHFFFAOYSA-N n-[2-[7-(methylsulfamoyl)naphthalen-1-yl]ethyl]acetamide Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(S(=O)(=O)NC)=CC=C21 LMMCCCKILDSFAH-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
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
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- 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
-
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- 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
- C07D333/74—Naphthothiophenes
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- 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
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- 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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- C07D335/08—Naphthothiopyrans; Hydrogenated naphthothiopyrans
-
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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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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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
- C07D405/12—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 chain containing hetero atoms as chain links
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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
- C07D471/04—Ortho-condensed systems
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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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- 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)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
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- Ceramic Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Inorganic Chemistry (AREA)
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- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9805957A FR2778662B1 (fr) | 1998-05-12 | 1998-05-12 | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR1999/001101 WO1999058496A1 (fr) | 1998-05-12 | 1999-05-10 | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
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| NZ507692A true NZ507692A (en) | 2002-06-28 |
Family
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Family Applications (2)
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| NZ507691A NZ507691A (en) | 1998-05-12 | 1999-05-10 | (Dihydro)benzothiophenes compounds suitable for treating melatonergic system disorders |
| NZ507692A NZ507692A (en) | 1998-05-12 | 1999-05-10 | Retroamide chain benzofuran and benzothiophene compounds substituted by amides or carbamates for use in melatonergic system disorders |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
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| NZ507691A NZ507691A (en) | 1998-05-12 | 1999-05-10 | (Dihydro)benzothiophenes compounds suitable for treating melatonergic system disorders |
Country Status (18)
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| EP (2) | EP1077927B1 (enExample) |
| JP (2) | JP2002514619A (enExample) |
| CN (2) | CN1300277A (enExample) |
| AT (2) | ATE312073T1 (enExample) |
| AU (2) | AU748567B2 (enExample) |
| BR (2) | BR9911783A (enExample) |
| CA (2) | CA2331870C (enExample) |
| DE (2) | DE69933147T2 (enExample) |
| DK (2) | DK1077928T3 (enExample) |
| ES (2) | ES2255260T3 (enExample) |
| FR (1) | FR2778662B1 (enExample) |
| HU (2) | HUP0101800A3 (enExample) |
| NO (2) | NO20005715L (enExample) |
| NZ (2) | NZ507691A (enExample) |
| PL (2) | PL195613B1 (enExample) |
| WO (2) | WO1999058496A1 (enExample) |
| ZA (2) | ZA200006529B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| 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 |
| 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 |
| BRPI0510642A (pt) * | 2004-05-05 | 2007-11-20 | Hoffmann La Roche | arilsulfonil benzodioxanos úteis para modulação do receptor de 5-ht6, do receptor de 5ht2a ou ambos |
| WO2006019497A2 (en) * | 2004-06-17 | 2006-02-23 | Neurocrine Biosciences, Inc. | Sleep-inducing compounds and methods related thereto |
| 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 |
| 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 |
| DE602005007064D1 (de) * | 2004-12-21 | 2008-07-03 | Hoffmann La Roche | Chromanderivate und ihre verwendung als liganden des 5-ht-rezeptors |
| RU2396255C2 (ru) * | 2004-12-21 | 2010-08-10 | Ф. Хоффманн-Ля Рош Аг | Производные тетралина и индана и их применения |
| EP1831203A1 (en) | 2004-12-21 | 2007-09-12 | F. Hoffmann-Roche AG | Chroman derivatives and uses thereof in the treatment of cns disorders |
| MX2007007482A (es) * | 2004-12-21 | 2007-07-20 | Hoffmann La Roche | Derivados de tetralina e indano y usos de los mismos como antagonistas de 5-ht. |
| CA2591793A1 (en) | 2004-12-21 | 2006-06-29 | F. Hoffmann-La Roche Ag | Tetralin and indane derivatives and uses thereof |
| WO2007051735A1 (en) * | 2005-11-03 | 2007-05-10 | F. Hoffmann-La Roche Ag | Arylsulfonylchromans as 5-ht6 inhibitors indolylmaleimide derivatives as protein kinase inhibitors |
| US8337721B2 (en) | 2005-12-02 | 2012-12-25 | Vanderbilt University | Broad-emission nanocrystals and methods of making and using same |
| JP5188988B2 (ja) * | 2006-02-10 | 2013-04-24 | トランステック ファーマ,インコーポレイティド | ベンゾアゾール誘導体、組成物、及びオーロラキナーゼ阻害剤としての使用方法 |
| KR101064001B1 (ko) * | 2006-06-20 | 2011-09-08 | 에프. 호프만-라 로슈 아게 | 아릴설폰아미딜 테트랄린 유도체 및 이의 용도 |
| 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 |
| MX2008015843A (es) * | 2006-06-20 | 2009-01-09 | Hoffmann La Roche | Derivados de tetralina e indano y usos de los mismos. |
| AU2008307575A1 (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 |
| KR102408261B1 (ko) | 2014-02-03 | 2022-06-10 | 비타이 파마슈티컬즈, 엘엘씨 | Ror-감마의 디하이드로피롤로피리딘 저해제 |
| 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 |
| UA118989C2 (uk) | 2014-10-14 | 2019-04-10 | Вітае Фармасьютікалс, Інк. | Дигідропіролопіридинові інгібітори ror-гамма |
| US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
| US9845308B2 (en) | 2014-11-05 | 2017-12-19 | Vitae Pharmaceuticals, Inc. | Isoindoline inhibitors of ROR-gamma |
| BR112017015510A2 (pt) | 2015-01-20 | 2018-01-30 | Xoc Pharmaceuticals Inc | composto de fórmula estrutural (i), método de tratamento e/ou prevenção, método de agonização do receptor d2 em um indivíduo, método de antagonização do receptor d3 em um indivíduo, método de agonização do receptor 5-ht1d em um indivíduo, método de agonização do receptor 5-ht1a em um indivíduo, método de agonização seletiva do receptor 5-ht1d em vez do receptor 5-ht1b em um indivíduo, método de agonização seletiva do re-ceptor 5-ht2c em vez do receptor 5-ht2a ou 5-ht2b em um indivíduo, método de agonização do receptor 5-ht2c em um indivíduo, método de fornecimento de atividade antagonista funcional no receptor 5-ht2b ou receptor 5-ht7, e, método de fornecimento de atividade antagonista funcional nos receptores adrenérgicos em um indivíduo |
| US9657020B2 (en) * | 2015-01-20 | 2017-05-23 | Xoc Pharmaceuticals, Inc. | Ergoline compounds and uses thereof |
| EP3331876B1 (en) | 2015-08-05 | 2020-10-07 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
| KR20180086221A (ko) | 2015-11-20 | 2018-07-30 | 비타이 파마슈티컬즈, 인코포레이티드 | Ror-감마의 조절물질 |
| TWI757266B (zh) | 2016-01-29 | 2022-03-11 | 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 |
| IL298639A (en) | 2017-07-24 | 2023-01-01 | Vitae Pharmaceuticals Llc | Inhibitors of gamma ror |
| 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 |
| KR20240035395A (ko) | 2021-06-14 | 2024-03-15 | 스코르피온 테라퓨틱스, 인코퍼레이티드 | 암 치료에 사용할 수 있는 요소 유도체 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| AU3399895A (en) * | 1994-09-12 | 1996-03-29 | Takeda Chemical Industries Ltd. | Benzocycloalkene compounds, their production and use |
| JP3908798B2 (ja) * | 1994-09-12 | 2007-04-25 | 武田薬品工業株式会社 | ベンゾシクロアルケン類、その製造法および剤 |
| AU4569496A (en) * | 1995-02-24 | 1996-09-05 | Bristol-Myers Squibb Company | Tetralinyl- and indanyl-ethylamides |
| 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 |
| ATE215540T1 (de) * | 1995-12-05 | 2002-04-15 | Darwin Discovery Ltd | 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
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1999
- 1999-05-10 CN CN99806053A patent/CN1300277A/zh active Pending
- 1999-05-10 NZ NZ507691A patent/NZ507691A/en unknown
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- 1999-05-10 WO PCT/FR1999/001100 patent/WO1999058495A1/fr not_active Ceased
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2003
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