JP2002514620A5 - - Google Patents
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- JP2002514620A5 JP2002514620A5 JP2000548300A JP2000548300A JP2002514620A5 JP 2002514620 A5 JP2002514620 A5 JP 2002514620A5 JP 2000548300 A JP2000548300 A JP 2000548300A JP 2000548300 A JP2000548300 A JP 2000548300A JP 2002514620 A5 JP2002514620 A5 JP 2002514620A5
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- 150000001875 compounds Chemical class 0.000 description 83
- 239000002253 acid Substances 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 20
- 229910052757 nitrogen Chemical group 0.000 description 18
- 230000009471 action Effects 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 16
- 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 description 14
- 150000007513 acids Chemical class 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 239000011593 sulfur Chemical group 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- -1 cyano, carboxy, nitro, amino Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000006685 (C1-C6) polyhaloalkyl group Chemical group 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 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 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003222 pyridines Chemical group 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical class C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 description 1
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- SAICYIJHJZKUJH-UHFFFAOYSA-N 3-ethylfuran-2-carboxamide Chemical compound CCC=1C=COC=1C(N)=O SAICYIJHJZKUJH-UHFFFAOYSA-N 0.000 description 1
- IEMRLVMQLSXWBI-UHFFFAOYSA-N 8-(acetamidomethyl)-n-propan-2-ylnaphthalene-2-carboxamide Chemical compound C1=CC=C(CNC(C)=O)C2=CC(C(=O)NC(C)C)=CC=C21 IEMRLVMQLSXWBI-UHFFFAOYSA-N 0.000 description 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 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- QWETUAVEDNSMMU-UHFFFAOYSA-N ethyl n-[3-(2-acetamidoethyl)-2,3-dihydro-1h-inden-5-yl]carbamate Chemical compound CCOC(=O)NC1=CC=C2CCC(CCNC(C)=O)C2=C1 QWETUAVEDNSMMU-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 1
- 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 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000003387 indolinyl group Chemical class N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OWRQGIILOGWMKK-UHFFFAOYSA-N methyl 3-(2-benzamidoethyl)-1-benzofuran-5-carboxylate Chemical group C12=CC(C(=O)OC)=CC=C2OC=C1CCNC(=O)C1=CC=CC=C1 OWRQGIILOGWMKK-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 1
- TXRRAONYRNIIJX-UHFFFAOYSA-N methyl n-[3-(2-acetamidoethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]carbamate Chemical compound COC(=O)NC1=CN=C2NC=C(CCNC(C)=O)C2=C1 TXRRAONYRNIIJX-UHFFFAOYSA-N 0.000 description 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 description 1
- ULPFFHCERVSEJV-UHFFFAOYSA-N methyl n-[3-(2-benzamidoethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]carbamate Chemical compound C12=CC(NC(=O)OC)=CN=C2NC=C1CCNC(=O)C1=CC=CC=C1 ULPFFHCERVSEJV-UHFFFAOYSA-N 0.000 description 1
- MUPLLDUULDSAQJ-UHFFFAOYSA-N methyl n-[3-(acetamidomethyl)-3,4-dihydro-2h-chromen-6-yl]carbamate Chemical compound O1CC(CNC(C)=O)CC2=CC(NC(=O)OC)=CC=C21 MUPLLDUULDSAQJ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 1
- JMWKRWJXCNQMPR-UHFFFAOYSA-N methyl n-[3-[2-(furan-2-carbonylamino)ethyl]-1h-pyrrolo[2,3-b]pyridin-5-yl]carbamate Chemical compound C12=CC(NC(=O)OC)=CN=C2NC=C1CCNC(=O)C1=CC=CO1 JMWKRWJXCNQMPR-UHFFFAOYSA-N 0.000 description 1
- MACRVFPGZJZGKT-UHFFFAOYSA-N methyl n-[5-(acetamidomethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]carbamate Chemical compound O1CCOC2=C(CNC(C)=O)C(NC(=O)OC)=CC=C21 MACRVFPGZJZGKT-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 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 description 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 description 1
- ACDJFBYGYHUWBE-UHFFFAOYSA-N n-[2-[5-[(4-ethoxyphenyl)sulfamoyl]-1h-indol-3-yl]ethyl]acetamide Chemical compound C1=CC(OCC)=CC=C1NS(=O)(=O)C1=CC=C(NC=C2CCNC(C)=O)C2=C1 ACDJFBYGYHUWBE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- ZZZMEMOYMVCOBE-UHFFFAOYSA-N n-[8-[2-[(2-bromoacetyl)amino]ethyl]naphthalen-2-yl]cyclohexanecarboxamide Chemical compound C1=C2C(CCNC(=O)CBr)=CC=CC2=CC=C1NC(=O)C1CCCCC1 ZZZMEMOYMVCOBE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- SMXMLMYFAJXOEI-UHFFFAOYSA-N n-benzyl-1-[2-[(2,2,2-trifluoroacetyl)amino]ethyl]naphthalene-2-carboxamide Chemical compound C1=CC2=CC=CC=C2C(CCNC(=O)C(F)(F)F)=C1C(=O)NCC1=CC=CC=C1 SMXMLMYFAJXOEI-UHFFFAOYSA-N 0.000 description 1
- MUQXMKNBPUPAAK-UHFFFAOYSA-N n-ethyl-8-[2-[(2-phenylacetyl)amino]ethyl]naphthalene-2-carboxamide Chemical compound C12=CC(C(=O)NCC)=CC=C2C=CC=C1CCNC(=O)CC1=CC=CC=C1 MUQXMKNBPUPAAK-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- LOGAFLFGWNBIIG-UHFFFAOYSA-N pyridin-3-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CN=C1 LOGAFLFGWNBIIG-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 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 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Applications Claiming Priority (3)
| 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 |
| FR98/05957 | 1998-05-12 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2002514620A JP2002514620A (ja) | 2002-05-21 |
| JP2002514620A5 true JP2002514620A5 (https=) | 2006-07-13 |
Family
ID=9526252
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000548299A Pending JP2002514619A (ja) | 1998-05-12 | 1999-05-10 | 新しい置換環状化合物、これらの製造方法及びこれらを含む薬剤組成物 |
| JP2000548300A Pending JP2002514620A (ja) | 1998-05-12 | 1999-05-10 | 新しい置換環状化合物、これらの製造方法及びこれらを含む薬剤組成物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000548299A Pending JP2002514619A (ja) | 1998-05-12 | 1999-05-10 | 新しい置換環状化合物、これらの製造方法及びこれらを含む薬剤組成物 |
Country Status (18)
| Country | Link |
|---|---|
| US (6) | US6872851B1 (https=) |
| EP (2) | EP1077928B1 (https=) |
| JP (2) | JP2002514619A (https=) |
| CN (2) | CN1300277A (https=) |
| AT (2) | ATE312073T1 (https=) |
| AU (2) | AU748567B2 (https=) |
| BR (2) | BR9911783A (https=) |
| CA (2) | CA2331870C (https=) |
| DE (2) | DE69933147T2 (https=) |
| DK (2) | DK1077927T3 (https=) |
| ES (2) | ES2255261T3 (https=) |
| FR (1) | FR2778662B1 (https=) |
| HU (2) | HUP0101800A3 (https=) |
| NO (2) | NO20005715L (https=) |
| NZ (2) | NZ507691A (https=) |
| PL (2) | PL195613B1 (https=) |
| WO (2) | WO1999058495A1 (https=) |
| ZA (2) | ZA200006529B (https=) |
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| AUPO274596A0 (en) * | 1996-10-04 | 1996-10-31 | Armstrong, Stuart Maxwell | Method for the treatment of neurological or neuropsychiatric disorders |
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| FR2814165B1 (fr) * | 2000-09-15 | 2002-11-22 | Adir | Nouveaux derives biphenyles substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| NZ526622A (en) * | 2000-12-11 | 2006-07-28 | Amgen Sf Llc | CXCR3 antagonists |
| 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 |
| CA2566196A1 (en) * | 2004-05-05 | 2005-11-10 | F. Hoffmann-La Roche Ag | Arylsulfonyl benzodioxanes useful for modulating the 5-ht6 receptor, the 5-ht2a receptor or both |
| 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 |
| BRPI0515835A (pt) | 2004-12-21 | 2008-08-12 | Hoffmann La Roche | derivados de tetralina e de indano e seus usos |
| ES2306275T3 (es) * | 2004-12-21 | 2008-11-01 | F. Hoffmann-La Roche Ag | Derivados de cromano y sus usos como ligandos dde receptores 5-ht. |
| RU2388748C2 (ru) * | 2004-12-21 | 2010-05-10 | Ф. Хоффманн-Ля Рош Аг | Производные тетралина и индана и их применения в качестве антагонистов 5-нт |
| CA2591810A1 (en) | 2004-12-21 | 2006-06-29 | F.Hoffmann-La Roche Ag | Chroman derivatives and uses thereof in the treatment of cns disorders |
| CA2628173A1 (en) * | 2005-11-03 | 2007-05-10 | F. Hoffmann-La Roche Ag | Arylsulfonylchromans as 5-ht6 inhibitors indolylmaleimide derivatives as protein kinase inhibitors |
| WO2007067257A2 (en) | 2005-12-02 | 2007-06-14 | Vanderbilt University | Broad-emission nanocrystals and methods of making and using same |
| CN101379060B (zh) * | 2006-02-10 | 2012-05-23 | 转化技术制药公司 | 作为Aurora激酶抑制剂的苯并唑系衍生物、组合物和使用方法 |
| MX2008015511A (es) | 2006-06-20 | 2008-12-18 | Hoffmann La Roche | Derivados de arilsulfonilnaftaleno y usos de los mismos. |
| BRPI0713736A2 (pt) * | 2006-06-20 | 2014-11-18 | Hoffmann La Roche | Derivados de tetralina e indano e emprego destes |
| AU2007263075A1 (en) * | 2006-06-20 | 2007-12-27 | F. Hoffmann-La Roche Ag | Arylsulfonamidyl tetralin derivatives and uses thereof |
| WO2009045385A1 (en) * | 2007-10-04 | 2009-04-09 | Merck & Co., Inc. | N-hydroxy-naphthalene dicarboxamide and n-hydroxy-biphenyl-dicarboxamide compounds as histone deacetylase inhibitors |
| EP2163551B1 (en) | 2008-09-08 | 2011-11-16 | Cadila Pharmaceuticals Ltd. | An improved process for the preparation of nebivolol hydrochloride |
| 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 |
| AU2015210833B2 (en) | 2014-02-03 | 2019-01-03 | 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 |
| JP6564029B2 (ja) | 2014-10-14 | 2019-08-21 | ヴァイティー ファーマシューティカルズ，エルエルシー | Ｒｏｒ−ガンマのジヒドロピロロピリジン阻害剤 |
| 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 |
| EP3247357A4 (en) | 2015-01-20 | 2018-07-11 | Xoc Pharmaceuticals, Inc | Isoergoline compounds and uses thereof |
| MX2017009405A (es) * | 2015-01-20 | 2018-01-18 | Xoc Pharmaceuticals Inc | Compuestos de tipo ergolina y usos de estos. |
| DK3331876T3 (da) | 2015-08-05 | 2021-01-11 | Vitae Pharmaceuticals Llc | Modulators of ror-gamma |
| MA53943A (fr) | 2015-11-20 | 2021-08-25 | Vitae Pharmaceuticals Llc | Modulateurs de ror-gamma |
| 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 |
| WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
| CN115650976A (zh) | 2017-07-24 | 2023-01-31 | 生命医药有限责任公司 | RORγ的抑制剂 |
| 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 |
| US20240300939A1 (en) | 2021-06-14 | 2024-09-12 | Scorpion Therapeutics, Inc. | Urea derivatives which can be used to treat cancer |
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| 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 |
| 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 |
| CZ292443B6 (cs) * | 1995-12-05 | 2003-09-17 | Darwin Discovery Limited | Benzofuransulfonamid, farmaceutický prostředek jej obsahující a jeho použití |
| 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 ES99918037T patent/ES2255261T3/es not_active Expired - Lifetime
- 1999-05-10 CN CN99806053A patent/CN1300277A/zh active Pending
- 1999-05-10 PL PL99344048A patent/PL195613B1/pl unknown
- 1999-05-10 EP EP99918037A patent/EP1077928B1/fr not_active Expired - Lifetime
- 1999-05-10 AU AU36103/99A patent/AU748567B2/en not_active Ceased
- 1999-05-10 NZ NZ507691A patent/NZ507691A/en unknown
- 1999-05-10 CA CA002331870A patent/CA2331870C/fr not_active Expired - Fee Related
- 1999-05-10 ES ES99918036T patent/ES2255260T3/es not_active Expired - Lifetime
- 1999-05-10 DE DE69933147T patent/DE69933147T2/de not_active Expired - Fee Related
- 1999-05-10 AT AT99918037T patent/ATE312073T1/de not_active IP Right Cessation
- 1999-05-10 JP JP2000548299A patent/JP2002514619A/ja active Pending
- 1999-05-10 NZ NZ507692A patent/NZ507692A/en unknown
- 1999-05-10 CA CA002331877A patent/CA2331877C/fr not_active Expired - Fee Related
- 1999-05-10 PL PL99344012A patent/PL344012A1/xx unknown
- 1999-05-10 DK DK99918036T patent/DK1077927T3/da active
- 1999-05-10 EP EP99918036A patent/EP1077927B1/fr not_active Expired - Lifetime
- 1999-05-10 HU HU0101800A patent/HUP0101800A3/hu unknown
- 1999-05-10 DK DK99918037T patent/DK1077928T3/da active
- 1999-05-10 AU AU36104/99A patent/AU747301B2/en not_active Ceased
- 1999-05-10 BR BR9911783-5A patent/BR9911783A/pt not_active Application Discontinuation
- 1999-05-10 JP JP2000548300A patent/JP2002514620A/ja active Pending
- 1999-05-10 HU HU0101813A patent/HUP0101813A3/hu unknown
- 1999-05-10 BR BR9911771-1A patent/BR9911771A/pt not_active Application Discontinuation
- 1999-05-10 AT AT99918036T patent/ATE312072T1/de not_active IP Right Cessation
- 1999-05-10 DE DE69933149T patent/DE69933149T2/de not_active Expired - Fee Related
- 1999-05-10 CN CN99806830A patent/CN1304400A/zh active Pending
- 1999-05-10 US US09/700,098 patent/US6872851B1/en not_active Expired - Fee Related
- 1999-05-10 WO PCT/FR1999/001100 patent/WO1999058495A1/fr not_active Ceased
- 1999-05-10 WO PCT/FR1999/001101 patent/WO1999058496A1/fr not_active Ceased
- 1999-05-10 US US09/700,056 patent/US6605632B1/en 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 NO20005715A patent/NO20005715L/no not_active Application Discontinuation
- 2000-11-13 NO NO20005714A patent/NO20005714D0/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 US10/947,757 patent/US7126012B2/en not_active Expired - Fee Related
- 2004-09-23 US US10/948,410 patent/US7115752B2/en not_active Expired - Fee Related
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