OA12846A - N,N'-substituted-1,3-diamino-2-hydroxypropane derivatives. - Google Patents
N,N'-substituted-1,3-diamino-2-hydroxypropane derivatives. Download PDFInfo
- Publication number
- OA12846A OA12846A OA1200400138A OA1200400138A OA12846A OA 12846 A OA12846 A OA 12846A OA 1200400138 A OA1200400138 A OA 1200400138A OA 1200400138 A OA1200400138 A OA 1200400138A OA 12846 A OA12846 A OA 12846A
- Authority
- OA
- OAPI
- Prior art keywords
- alkyl
- phenyl
- optionally substituted
- alkoxy
- independently
- Prior art date
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- 229910052757 nitrogen Inorganic materials 0.000 title claims description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 410
- 125000000217 alkyl group Chemical group 0.000 claims description 1648
- -1 dihydronaphthayl Chemical group 0.000 claims description 621
- 229910052736 halogen Inorganic materials 0.000 claims description 374
- 150000002367 halogens Chemical class 0.000 claims description 354
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 256
- 229910052739 hydrogen Inorganic materials 0.000 claims description 224
- 239000001257 hydrogen Substances 0.000 claims description 202
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 189
- 125000003545 alkoxy group Chemical group 0.000 claims description 186
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 174
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 146
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 137
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 137
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 134
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 128
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 115
- 125000003282 alkyl amino group Chemical group 0.000 claims description 96
- 125000001246 bromo group Chemical group Br* 0.000 claims description 94
- 125000000304 alkynyl group Chemical group 0.000 claims description 91
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 87
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 85
- 125000001424 substituent group Chemical group 0.000 claims description 82
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 81
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 75
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 74
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 71
- 125000003342 alkenyl group Chemical group 0.000 claims description 65
- 125000005843 halogen group Chemical group 0.000 claims description 65
- 229910052799 carbon Inorganic materials 0.000 claims description 59
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 51
- 125000002541 furyl group Chemical group 0.000 claims description 51
- 125000004076 pyridyl group Chemical group 0.000 claims description 49
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 47
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 47
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 46
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 45
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 44
- 125000001544 thienyl group Chemical group 0.000 claims description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 39
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 39
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 36
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 33
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 32
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 27
- 125000000335 thiazolyl group Chemical group 0.000 claims description 27
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 24
- 150000001721 carbon Chemical group 0.000 claims description 24
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 24
- 125000003386 piperidinyl group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000002971 oxazolyl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 20
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 17
- 125000002883 imidazolyl group Chemical group 0.000 claims description 17
- 125000004193 piperazinyl group Chemical group 0.000 claims description 17
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 17
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 16
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 15
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 14
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 13
- 229910052707 ruthenium Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 11
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 11
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 10
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 10
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 9
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 9
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- NKPTVQFJWGCELJ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)CCC2=C1 NKPTVQFJWGCELJ-UHFFFAOYSA-N 0.000 claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 8
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000005959 diazepanyl group Chemical group 0.000 claims description 7
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 7
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- KOAMXHRRVFDWRQ-UHFFFAOYSA-N 4,4-dimethyl-5h-1,3-oxazole Chemical compound CC1(C)COC=N1 KOAMXHRRVFDWRQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003725 azepanyl group Chemical group 0.000 claims description 6
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000005992 dihydrobenzisothiazinyl group Chemical group 0.000 claims description 6
- 125000005993 dihydrobenzisoxazinyl group Chemical group 0.000 claims description 6
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 6
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000005994 isobenzotetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000005995 isobenzotetrahydrothienyl group Chemical group 0.000 claims description 6
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 6
- 125000003151 isocoumarinyl group Chemical group C1(=O)OC(=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001475 halogen functional group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 5
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 5
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 5
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 claims description 5
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 5
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 5
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 5
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 4
- FRJNKYGTHPUSJR-UHFFFAOYSA-N 1-benzothiophene 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)C=CC2=C1 FRJNKYGTHPUSJR-UHFFFAOYSA-N 0.000 claims description 4
- GVYVHZKTSVDMNT-UHFFFAOYSA-N 2,3-dihydro-1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)NCC2=C1 GVYVHZKTSVDMNT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
- YHBTXTFFTYXOFV-UHFFFAOYSA-N Liquid thiophthene Chemical compound C1=CSC2=C1C=CS2 YHBTXTFFTYXOFV-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 4
- 125000005051 dihydropyrazinyl group Chemical group N1(CC=NC=C1)* 0.000 claims description 4
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims description 4
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 4
- 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 claims description 4
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 4
- 125000005883 dithianyl group Chemical group 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
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical compound C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 claims description 3
- TVAXADJKLPDCJU-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)CCCC2=C1 TVAXADJKLPDCJU-UHFFFAOYSA-N 0.000 claims description 3
- ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 2
- VSCYCJOVRGSJBT-UHFFFAOYSA-N 3,4-dihydro-2h-1$l^{6},2-benzothiazine 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)NCCC2=C1 VSCYCJOVRGSJBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
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- WLVSGEUMMFAYAI-UHFFFAOYSA-N methyl 3-carbamoyl-5-(dipropylcarbamoyl)benzoate Chemical compound CCCN(CCC)C(=O)C1=CC(C(N)=O)=CC(C(=O)OC)=C1 WLVSGEUMMFAYAI-UHFFFAOYSA-N 0.000 description 1
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 1
- POFWRMVFWIJXHP-UHFFFAOYSA-N n-benzyl-9-(oxan-2-yl)purin-6-amine Chemical compound C=1C=CC=CC=1CNC(C=1N=C2)=NC=NC=1N2C1CCCCO1 POFWRMVFWIJXHP-UHFFFAOYSA-N 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000003585 oxepinyl group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- IGWKVIVLBSAOFQ-QWHCGFSZSA-N tert-butyl N-[(2S,3R)-4-azido-1-(3,5-difluorophenyl)-3-hydroxybutan-2-yl]carbamate Chemical compound C(C)(C)(C)OC(N[C@H]([C@@H](CN=[N+]=[N-])O)CC1=CC(=CC(=C1)F)F)=O IGWKVIVLBSAOFQ-QWHCGFSZSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07C233/00—Carboxylic acid amides
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- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
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- C07C235/50—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/38—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
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- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
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| DE10034673C1 (de) * | 2000-07-17 | 2002-04-25 | Medac Klinische Spezialpraep | Dermales Applikationssystem für Aminolävulinsäure und seine Verwendung |
| BR0210721A (pt) | 2001-06-27 | 2004-07-20 | Elan Pharm Inc | Composto, sal ou éster farmaceuticamente aceitável, método para fabricar um composto, e, método para tratar um paciente que tem, ou para evitar que o paciente adquira uma doença ou condição |
| RS13004A (sr) * | 2001-07-11 | 2006-10-27 | Elan Pharmaceuticals Inc. | N-(3-amino-2-hidroksi-propil) supstituisana alkilamidna jedinjenja |
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| DE10202487A1 (de) * | 2002-01-23 | 2003-07-31 | Photonamic Gmbh & Co Kg | Dermales Applikationssystem für Aminolävulinsäure-Derivate |
| EP1521577A1 (de) * | 2002-06-13 | 2005-04-13 | QLT, Inc. | Verfahren zur verwendung von isothiazolderivaten zur behandlung von krebs oder entzündungen |
| CA2489095A1 (en) * | 2002-06-17 | 2003-12-24 | Sunesis Pharmaceuticals, Inc. | Aspartyl protease inhibitors |
| MXPA04012630A (es) * | 2002-06-20 | 2005-09-30 | Pharmacia & Upjohn Co Llc | Proceso para preparar derivados de acido 5-(1,3-oxazol-2-il)benzoico. |
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| AU2003254844A1 (en) * | 2002-08-09 | 2004-02-25 | Takeda Chemical Industries, Ltd. | Substituted amino compounds and use thereof |
| KR20050049485A (ko) * | 2002-09-06 | 2005-05-25 | 엘란 파마슈티칼스, 인크. | 1,3-디아미노-2-히드록시프로판 전구약물 유도체 |
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-
2002
- 2002-11-08 EP EP02793909A patent/EP1453789A2/de not_active Withdrawn
- 2002-11-08 IL IL16188102A patent/IL161881A0/xx active IP Right Grant
- 2002-11-08 US US10/291,318 patent/US7176242B2/en not_active Expired - Fee Related
- 2002-11-08 BR BR0214035-7A patent/BR0214035A/pt not_active IP Right Cessation
- 2002-11-08 JP JP2003542142A patent/JP2005520791A/ja active Pending
- 2002-11-08 MX MXPA04004428A patent/MXPA04004428A/es active IP Right Grant
- 2002-11-08 CA CA002466284A patent/CA2466284A1/en not_active Abandoned
- 2002-11-08 WO PCT/US2002/036072 patent/WO2003040096A2/en not_active Ceased
- 2002-11-08 KR KR1020047007148A patent/KR20050044407A/ko not_active Withdrawn
- 2002-11-08 EA EA200400648A patent/EA200400648A1/ru unknown
- 2002-11-08 TW TW091132884A patent/TW200304808A/zh unknown
- 2002-11-08 HR HR20040518A patent/HRP20040518A2/xx not_active Application Discontinuation
- 2002-11-08 GE GE5633A patent/GEP20074171B/en unknown
- 2002-11-08 OA OA1200400138A patent/OA12846A/en unknown
- 2002-11-08 RS YUP-505/04A patent/RS50504A/sr unknown
- 2002-11-08 AR ARP020104299A patent/AR039555A1/es unknown
- 2002-11-08 AP APAP/P/2004/003049A patent/AP2004003049A0/en unknown
- 2002-11-08 NZ NZ533107A patent/NZ533107A/en not_active IP Right Cessation
- 2002-11-08 AU AU2002359376A patent/AU2002359376B2/en not_active Ceased
-
2004
- 2004-05-07 IS IS7255A patent/IS7255A/is unknown
- 2004-05-09 IL IL161881A patent/IL161881A/en not_active IP Right Cessation
- 2004-05-10 CO CO04042905A patent/CO5640093A2/es not_active Application Discontinuation
- 2004-05-10 TN TNP2004000082A patent/TNSN04082A1/en unknown
- 2004-05-10 EC EC2004005100A patent/ECSP045100A/es unknown
-
2006
- 2006-12-11 US US11/636,903 patent/US7727997B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20070213316A1 (en) | 2007-09-13 |
| CO5640093A2 (es) | 2006-05-31 |
| TW200304808A (en) | 2003-10-16 |
| EP1453789A2 (de) | 2004-09-08 |
| CA2466284A1 (en) | 2003-05-15 |
| ECSP045100A (es) | 2006-06-27 |
| GEP20074171B (en) | 2007-07-25 |
| JP2005520791A (ja) | 2005-07-14 |
| WO2003040096A2 (en) | 2003-05-15 |
| IL161881A0 (en) | 2005-11-20 |
| AU2002359376B8 (en) | 2003-05-19 |
| TNSN04082A1 (en) | 2006-06-01 |
| RS50504A (sr) | 2007-04-10 |
| IS7255A (is) | 2004-05-07 |
| US7727997B2 (en) | 2010-06-01 |
| US7176242B2 (en) | 2007-02-13 |
| KR20050044407A (ko) | 2005-05-12 |
| EA200400648A1 (ru) | 2005-04-28 |
| BR0214035A (pt) | 2005-04-26 |
| MXPA04004428A (es) | 2004-09-10 |
| IL161881A (en) | 2011-01-31 |
| HRP20040518A2 (hr) | 2007-08-31 |
| WO2003040096A3 (en) | 2004-05-06 |
| US20040171881A1 (en) | 2004-09-02 |
| AR039555A1 (es) | 2005-02-23 |
| AU2002359376B2 (en) | 2008-01-10 |
| AP2004003049A0 (en) | 2004-06-30 |
| NZ533107A (en) | 2007-04-27 |
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