CA2331870C - Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent - Google Patents
Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent Download PDFInfo
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- CA2331870C CA2331870C CA002331870A CA2331870A CA2331870C CA 2331870 C CA2331870 C CA 2331870C CA 002331870 A CA002331870 A CA 002331870A CA 2331870 A CA2331870 A CA 2331870A CA 2331870 C CA2331870 C CA 2331870C
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- ethyl
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- acid
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- 238000002360 preparation method Methods 0.000 title claims description 570
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 150000001923 cyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 211
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 32
- 239000003814 drug Substances 0.000 claims abstract description 3
- -1 atoms halogen Chemical class 0.000 claims description 165
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 130
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 127
- 239000002253 acid Substances 0.000 claims description 88
- 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
- 238000000034 method Methods 0.000 claims description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 229910052717 sulfur Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 230000009471 action Effects 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000003573 thiols Chemical class 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 229910052736 halogen Inorganic materials 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
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 5
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims description 4
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical group C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 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
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- IHFOOJPQLJKXMS-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-(7-methylsulfanylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=CC=C(CCNC(=O)C(F)(F)F)C2=CC(SC)=CC=C21 IHFOOJPQLJKXMS-UHFFFAOYSA-N 0.000 claims description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QOOZHYPNCOMUGU-UHFFFAOYSA-N n-[2-(2-benzyl-5-sulfanyl-1-benzofuran-3-yl)ethyl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)NCCC=1C2=CC(S)=CC=C2OC=1CC1=CC=CC=C1 QOOZHYPNCOMUGU-UHFFFAOYSA-N 0.000 claims description 3
- BGPWBOCDXZAVMY-UHFFFAOYSA-N n-[2-(3-benzyl-7-sulfanylnaphthalen-1-yl)ethyl]cyclohexanecarboxamide Chemical compound C1=C(CCNC(=O)C2CCCCC2)C2=CC(S)=CC=C2C=C1CC1=CC=CC=C1 BGPWBOCDXZAVMY-UHFFFAOYSA-N 0.000 claims description 3
- RBDVGQGLCRUMHS-UHFFFAOYSA-N n-[2-(5-sulfanyl-1-benzofuran-3-yl)ethyl]acetamide Chemical compound C1=C(S)C=C2C(CCNC(=O)C)=COC2=C1 RBDVGQGLCRUMHS-UHFFFAOYSA-N 0.000 claims description 3
- VNFOEJMDQTWJKD-UHFFFAOYSA-N n-[2-(7-benzylsulfanylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C2C(CCNC(=O)C)=CC=CC2=CC=C1SCC1=CC=CC=C1 VNFOEJMDQTWJKD-UHFFFAOYSA-N 0.000 claims description 3
- MCDZFOHNKRGHNW-UHFFFAOYSA-N n-[2-(7-benzylsulfanylnaphthalen-1-yl)ethyl]heptanamide Chemical compound C1=C2C(CCNC(=O)CCCCCC)=CC=CC2=CC=C1SCC1=CC=CC=C1 MCDZFOHNKRGHNW-UHFFFAOYSA-N 0.000 claims description 3
- VUVZFIMHVADDLL-UHFFFAOYSA-N n-[2-(7-benzylsulfinylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C2C(CCNC(=O)C)=CC=CC2=CC=C1S(=O)CC1=CC=CC=C1 VUVZFIMHVADDLL-UHFFFAOYSA-N 0.000 claims description 3
- ZMDWAOWABWHEJS-UHFFFAOYSA-N n-[2-(7-methylsulfanyl-1,2,3,4-tetrahydronaphthalen-1-yl)ethyl]acetamide Chemical compound C1CCC(CCNC(C)=O)C2=CC(SC)=CC=C21 ZMDWAOWABWHEJS-UHFFFAOYSA-N 0.000 claims description 3
- TYFWDOQGHVONSS-UHFFFAOYSA-N n-[2-(7-methylsulfanylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(SC)=CC=C21 TYFWDOQGHVONSS-UHFFFAOYSA-N 0.000 claims description 3
- YWUASSYRKBAKKI-UHFFFAOYSA-N n-[2-(7-methylsulfinyl-1,2,3,4-tetrahydronaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C(S(C)=O)C=C2C(CCNC(=O)C)CCCC2=C1 YWUASSYRKBAKKI-UHFFFAOYSA-N 0.000 claims description 3
- VHUITCKFPJTFHR-UHFFFAOYSA-N n-[2-(7-methylsulfinylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C(S(C)=O)C=C2C(CCNC(=O)C)=CC=CC2=C1 VHUITCKFPJTFHR-UHFFFAOYSA-N 0.000 claims description 3
- CVHICHLEOMYVIL-UHFFFAOYSA-N n-[2-(7-methylsulfonyl-1,2,3,4-tetrahydronaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C(S(C)(=O)=O)C=C2C(CCNC(=O)C)CCCC2=C1 CVHICHLEOMYVIL-UHFFFAOYSA-N 0.000 claims description 3
- MZUIKFQBGPXOJR-UHFFFAOYSA-N n-[2-(7-methylsulfonylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C(S(C)(=O)=O)C=C2C(CCNC(=O)C)=CC=CC2=C1 MZUIKFQBGPXOJR-UHFFFAOYSA-N 0.000 claims description 3
- VRCDMNPLOIQWJT-UHFFFAOYSA-N n-[2-(7-sulfanylnaphthalen-1-yl)ethyl]benzamide Chemical compound C12=CC(S)=CC=C2C=CC=C1CCNC(=O)C1=CC=CC=C1 VRCDMNPLOIQWJT-UHFFFAOYSA-N 0.000 claims description 3
- HNSXAIJTBIYBHA-UHFFFAOYSA-N n-[2-[7-(hexylamino)-1,2,3,4-tetrahydronaphthalen-1-yl]ethyl]acetamide Chemical compound C1CCC(CCNC(C)=O)C2=CC(NCCCCCC)=CC=C21 HNSXAIJTBIYBHA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 3
- 238000007280 thionation reaction Methods 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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- 238000007239 Wittig reaction Methods 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 230000017858 demethylation Effects 0.000 claims description 2
- 238000010520 demethylation reaction Methods 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 2
- 230000022244 formylation Effects 0.000 claims description 2
- 238000006170 formylation reaction Methods 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002475 indoles Chemical group 0.000 claims description 2
- 238000006138 lithiation reaction Methods 0.000 claims description 2
- FCEZAIOOMFGMKT-UHFFFAOYSA-N n-[(6-morpholin-4-yl-2-phenyl-2h-chromen-3-yl)methyl]acetamide Chemical compound CC(=O)NCC1=CC2=CC(N3CCOCC3)=CC=C2OC1C1=CC=CC=C1 FCEZAIOOMFGMKT-UHFFFAOYSA-N 0.000 claims description 2
- KWJZDCYCZTVANE-UHFFFAOYSA-N n-[2-(2-phenyl-5-propylsulfanyl-1-benzothiophen-3-yl)ethyl]acetamide Chemical compound CC(=O)NCCC=1C2=CC(SCCC)=CC=C2SC=1C1=CC=CC=C1 KWJZDCYCZTVANE-UHFFFAOYSA-N 0.000 claims description 2
- FRIKDVFYQMYXKY-UHFFFAOYSA-N n-[2-(3-benzoyl-7-methylsulfanylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C(CCNC(C)=O)C2=CC(SC)=CC=C2C=C1C(=O)C1=CC=CC=C1 FRIKDVFYQMYXKY-UHFFFAOYSA-N 0.000 claims description 2
- UIWVJTHHRPYGHX-UHFFFAOYSA-N n-[2-(3-benzyl-7-methylsulfanylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C(CCNC(C)=O)C2=CC(SC)=CC=C2C=C1CC1=CC=CC=C1 UIWVJTHHRPYGHX-UHFFFAOYSA-N 0.000 claims description 2
- JICNOTFGSVBSSV-UHFFFAOYSA-N n-[2-(7-benzylsulfanyl-3-phenylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C2C(CCNC(=O)C)=CC(C=3C=CC=CC=3)=CC2=CC=C1SCC1=CC=CC=C1 JICNOTFGSVBSSV-UHFFFAOYSA-N 0.000 claims description 2
- PDZOLEHADYMJAF-UHFFFAOYSA-N n-[2-(7-benzylsulfonylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=C2C(CCNC(=O)C)=CC=CC2=CC=C1S(=O)(=O)CC1=CC=CC=C1 PDZOLEHADYMJAF-UHFFFAOYSA-N 0.000 claims description 2
- HIXXCXUIVMDINM-UHFFFAOYSA-N n-[2-(7-methylsulfanylnaphthalen-1-yl)ethyl]cyclopropanecarboxamide Chemical compound C12=CC(SC)=CC=C2C=CC=C1CCNC(=O)C1CC1 HIXXCXUIVMDINM-UHFFFAOYSA-N 0.000 claims description 2
- MTRBAXYNLVSFDY-UHFFFAOYSA-N n-[2-[5-(3-methylbutylsulfanyl)-1-benzothiophen-3-yl]ethyl]prop-2-enamide Chemical compound CC(C)CCSC1=CC=C2SC=C(CCNC(=O)C=C)C2=C1 MTRBAXYNLVSFDY-UHFFFAOYSA-N 0.000 claims description 2
- QTWDGEJYGSFEMZ-UHFFFAOYSA-N n-[2-[7-(diethylamino)naphthalen-1-yl]ethyl]-2-phenylacetamide Chemical compound C12=CC(N(CC)CC)=CC=C2C=CC=C1CCNC(=O)CC1=CC=CC=C1 QTWDGEJYGSFEMZ-UHFFFAOYSA-N 0.000 claims description 2
- GUDUGNAYAMEGNW-UHFFFAOYSA-N n-[2-[7-amino-3-(cyclopropylmethyl)naphthalen-1-yl]ethyl]acetamide Chemical compound C=1C2=CC=C(N)C=C2C(CCNC(=O)C)=CC=1CC1CC1 GUDUGNAYAMEGNW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- 238000005949 ozonolysis reaction Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- NNWLHBCKEQMHKH-UHFFFAOYSA-N 1-methyl-3-[2-(7-methylsulfanylnaphthalen-1-yl)ethyl]urea Chemical compound C1=C(SC)C=C2C(CCNC(=O)NC)=CC=CC2=C1 NNWLHBCKEQMHKH-UHFFFAOYSA-N 0.000 claims 1
- ZPXJKIVGYVDEDN-UHFFFAOYSA-N 2-(7-cyclopentylsulfanylnaphthalen-1-yl)-n-methylacetamide Chemical compound C1=C2C(CC(=O)NC)=CC=CC2=CC=C1SC1CCCC1 ZPXJKIVGYVDEDN-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- IWNRYVPWHCQKSK-UHFFFAOYSA-N 2-acetamido-3-[2,7-bis(2-hydroxyethylsulfanyl)-1h-indol-3-yl]propanamide Chemical compound C1=CC=C2C(CC(NC(=O)C)C(N)=O)=C(SCCO)NC2=C1SCCO IWNRYVPWHCQKSK-UHFFFAOYSA-N 0.000 claims 1
- HWFYLNQHHRMDHQ-UHFFFAOYSA-N 2-acetamido-3-[7-(2-hydroxyethylsulfanyl)-1h-indol-3-yl]propanamide Chemical compound C1=CC=C2C(CC(NC(=O)C)C(N)=O)=CNC2=C1SCCO HWFYLNQHHRMDHQ-UHFFFAOYSA-N 0.000 claims 1
- 229910019213 POCl3 Inorganic materials 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 1
- RYHHJKDZGCJFNO-UHFFFAOYSA-N n-[(2-benzyl-5-but-3-enylsulfanyl-1-benzothiophen-3-yl)methyl]acetamide Chemical compound S1C2=CC=C(SCCC=C)C=C2C(CNC(=O)C)=C1CC1=CC=CC=C1 RYHHJKDZGCJFNO-UHFFFAOYSA-N 0.000 claims 1
- NPWWYRGHXLWMAW-UHFFFAOYSA-N n-[2-(5-pyridin-2-ylsulfanyl-1-benzofuran-3-yl)ethyl]acetamide Chemical compound C1=C2C(CCNC(=O)C)=COC2=CC=C1SC1=CC=CC=N1 NPWWYRGHXLWMAW-UHFFFAOYSA-N 0.000 claims 1
- IJBYSBWGZKMBMG-UHFFFAOYSA-N n-[2-(7-ethylsulfanylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(SCC)=CC=C21 IJBYSBWGZKMBMG-UHFFFAOYSA-N 0.000 claims 1
- DWNGHLJHDQQWIL-UHFFFAOYSA-N n-[2-(7-methylsulfanylnaphthalen-1-yl)ethyl]butanamide Chemical compound C1=C(SC)C=C2C(CCNC(=O)CCC)=CC=CC2=C1 DWNGHLJHDQQWIL-UHFFFAOYSA-N 0.000 claims 1
- VIMNEBUQXGHMFF-UHFFFAOYSA-N n-[2-(7-propylsulfanylnaphthalen-1-yl)ethyl]acetamide Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(SCCC)=CC=C21 VIMNEBUQXGHMFF-UHFFFAOYSA-N 0.000 claims 1
- IARKOECUOPUDRJ-UHFFFAOYSA-N n-[3-(7-prop-1-enylsulfanyl-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]acetamide Chemical compound C1CCC(CCCNC(C)=O)C2=CC(SC=CC)=CC=C21 IARKOECUOPUDRJ-UHFFFAOYSA-N 0.000 claims 1
- LNYZRYGIRNMZKY-UHFFFAOYSA-N n-[[2-(furan-2-ylmethyl)-5-prop-2-ynylsulfanyl-1-benzofuran-3-yl]methyl]acetamide Chemical compound O1C2=CC=C(SCC#C)C=C2C(CNC(=O)C)=C1CC1=CC=CO1 LNYZRYGIRNMZKY-UHFFFAOYSA-N 0.000 claims 1
- IBYCIBCRTYGCPG-UHFFFAOYSA-N n-cyclohexyl-4-(7-phenylsulfanylnaphthalen-1-yl)butanamide Chemical compound C1CCCCC1NC(=O)CCCC(C1=C2)=CC=CC1=CC=C2SC1=CC=CC=C1 IBYCIBCRTYGCPG-UHFFFAOYSA-N 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 330
- 239000007858 starting material Substances 0.000 description 160
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- PLARSOSNLHDVBY-UHFFFAOYSA-N n-[3-[7-(4-methylpent-1-yn-3-ylsulfanyl)naphthalen-1-yl]propyl]acetamide Chemical compound C1=CC=C(CCCNC(C)=O)C2=CC(SC(C(C)C)C#C)=CC=C21 PLARSOSNLHDVBY-UHFFFAOYSA-N 0.000 description 1
- VPVJBLTZGHYPGR-UHFFFAOYSA-N n-[3-[7-[benzyl(ethynyl)amino]naphthalen-1-yl]propyl]cyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NCCCC(C1=C2)=CC=CC1=CC=C2N(C#C)CC1=CC=CC=C1 VPVJBLTZGHYPGR-UHFFFAOYSA-N 0.000 description 1
- LSOOBMQHVJYUGB-UHFFFAOYSA-N n-[4,9-bis(tert-butylsulfanyl)-2,3-dihydro-1h-phenalen-2-yl]acetamide Chemical compound C1=C(SC(C)(C)C)C(CC(NC(=O)C)C2)=C3C2=C(SC(C)(C)C)C=CC3=C1 LSOOBMQHVJYUGB-UHFFFAOYSA-N 0.000 description 1
- HQFRIFPCNASGAC-UHFFFAOYSA-N n-[4,9-bis(tert-butylsulfinyl)-2,3-dihydro-1h-phenalen-2-yl]acetamide Chemical compound C1=C(S(=O)C(C)(C)C)C(CC(NC(=O)C)C2)=C3C2=C(S(=O)C(C)(C)C)C=CC3=C1 HQFRIFPCNASGAC-UHFFFAOYSA-N 0.000 description 1
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- ZTAQYDKJSASZDZ-UHFFFAOYSA-N n-[[2-phenyl-6-(3-phenylprop-2-enylsulfanyl)-1,4-benzodioxin-3-yl]methyl]acetamide Chemical compound C1=C2OC(CNC(=O)C)=C(C=3C=CC=CC=3)OC2=CC=C1SCC=CC1=CC=CC=C1 ZTAQYDKJSASZDZ-UHFFFAOYSA-N 0.000 description 1
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- AHCAJLNUUUCMFV-UHFFFAOYSA-N n-[[7-(4-propan-2-ylphenyl)sulfanyl-3-thiophen-2-ylnaphthalen-1-yl]methyl]butanamide Chemical compound C1=C2C(CNC(=O)CCC)=CC(C=3SC=CC=3)=CC2=CC=C1SC1=CC=C(C(C)C)C=C1 AHCAJLNUUUCMFV-UHFFFAOYSA-N 0.000 description 1
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- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
- IHPHPGLJYCDONF-UHFFFAOYSA-N n-propylacetamide Chemical compound CCCNC(C)=O IHPHPGLJYCDONF-UHFFFAOYSA-N 0.000 description 1
- XABQSRSGMZTGPZ-UHFFFAOYSA-N naphthalene;1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2CCCCC2=C1.C1=CC=CC2=CC=CC=C21 XABQSRSGMZTGPZ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- UTRGDXSNAXJPJU-UHFFFAOYSA-N o-[3-(2-acetamidoethyl)-2-phenyl-1h-pyrrolo[2,3-b]pyridin-5-yl] cyclopentanecarbothioate Chemical compound C1=C2C(CCNC(=O)C)=C(C=3C=CC=CC=3)NC2=NC=C1OC(=S)C1CCCC1 UTRGDXSNAXJPJU-UHFFFAOYSA-N 0.000 description 1
- KPYYKHVQJNEMGK-UHFFFAOYSA-N o-[8-(2-benzamidoethyl)naphthalen-2-yl] propanethioate Chemical compound C12=CC(OC(=S)CC)=CC=C2C=CC=C1CCNC(=O)C1=CC=CC=C1 KPYYKHVQJNEMGK-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
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- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- RIZGKEIRSQLIBK-UHFFFAOYSA-N prop-1-ene-1-thiol Chemical compound CC=CS RIZGKEIRSQLIBK-UHFFFAOYSA-N 0.000 description 1
- AWRYQBZTGRGDHR-UHFFFAOYSA-N prop-1-yne-1-thiol Chemical compound CC#CS AWRYQBZTGRGDHR-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
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- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 1
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 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
- 230000001052 transient effect Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- 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
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- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
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- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
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- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- Hematology (AREA)
- Reproductive Health (AREA)
- Inorganic Chemistry (AREA)
- Emergency Medicine (AREA)
- Pregnancy & Childbirth (AREA)
- Gynecology & Obstetrics (AREA)
- 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 (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/FR1999/001100 WO1999058495A1 (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 |
|---|---|
| CA2331870A1 CA2331870A1 (fr) | 1999-11-18 |
| CA2331870C true CA2331870C (fr) | 2007-05-08 |
Family
ID=9526252
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002331870A Expired - Fee Related CA2331870C (fr) | 1998-05-12 | 1999-05-10 | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CA002331877A Expired - Fee Related CA2331877C (fr) | 1998-05-12 | 1999-05-10 | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002331877A Expired - Fee Related CA2331877C (fr) | 1998-05-12 | 1999-05-10 | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
-
1999
- 1999-05-10 CN CN99806053A patent/CN1300277A/zh active Pending
- 1999-05-10 NZ NZ507691A patent/NZ507691A/en unknown
- 1999-05-10 AU AU36103/99A patent/AU748567B2/en not_active Ceased
- 1999-05-10 AU AU36104/99A patent/AU747301B2/en not_active Ceased
- 1999-05-10 AT AT99918037T patent/ATE312073T1/de not_active IP Right Cessation
- 1999-05-10 ES ES99918036T patent/ES2255260T3/es not_active Expired - Lifetime
- 1999-05-10 ES ES99918037T patent/ES2255261T3/es not_active Expired - Lifetime
- 1999-05-10 HU HU0101800A patent/HUP0101800A3/hu unknown
- 1999-05-10 BR BR9911783-5A patent/BR9911783A/pt not_active Application Discontinuation
- 1999-05-10 CA CA002331870A patent/CA2331870C/fr not_active Expired - Fee Related
- 1999-05-10 US US09/700,098 patent/US6872851B1/en not_active Expired - Fee Related
- 1999-05-10 WO PCT/FR1999/001101 patent/WO1999058496A1/fr not_active Ceased
- 1999-05-10 JP JP2000548299A patent/JP2002514619A/ja active Pending
- 1999-05-10 DK DK99918037T patent/DK1077928T3/da active
- 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 NZ NZ507692A patent/NZ507692A/en unknown
- 1999-05-10 DK DK99918036T patent/DK1077927T3/da active
- 1999-05-10 BR BR9911771-1A patent/BR9911771A/pt not_active Application Discontinuation
- 1999-05-10 DE DE69933147T patent/DE69933147T2/de not_active Expired - Fee Related
- 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 US US09/700,056 patent/US6605632B1/en not_active Expired - Fee Related
- 1999-05-10 CN CN99806830A patent/CN1304400A/zh active Pending
- 1999-05-10 PL PL99344048A patent/PL195613B1/pl unknown
- 1999-05-10 PL PL99344012A patent/PL344012A1/xx unknown
- 1999-05-10 WO PCT/FR1999/001100 patent/WO1999058495A1/fr not_active Ceased
- 1999-05-10 EP EP99918036A patent/EP1077927B1/fr not_active Expired - Lifetime
- 1999-05-10 EP EP99918037A patent/EP1077928B1/fr not_active Expired - Lifetime
- 1999-05-10 JP JP2000548300A patent/JP2002514620A/ja active Pending
-
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/NO20005714L/no not_active Application Discontinuation
-
2003
- 2003-06-16 US US10/462,331 patent/US7183318B2/en not_active Expired - Fee Related
- 2003-06-16 US US10/462,326 patent/US20040002490A1/en not_active Abandoned
-
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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