JP2008523145A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2008523145A5 JP2008523145A5 JP2007546793A JP2007546793A JP2008523145A5 JP 2008523145 A5 JP2008523145 A5 JP 2008523145A5 JP 2007546793 A JP2007546793 A JP 2007546793A JP 2007546793 A JP2007546793 A JP 2007546793A JP 2008523145 A5 JP2008523145 A5 JP 2008523145A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclobutane
- chromene
- dihydrospiro
- dimethyl
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- -1 nitro, cyano, amino, aminosulfonyl Chemical group 0.000 claims description 61
- 150000002431 hydrogen Chemical class 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- FXIBPABYBWWXDV-NSHDSACASA-N (4s)-4-(methoxyamino)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C([C@@H](C1=C(C)C(O)=C(C)C=C1O1)NOC)C21CCC2 FXIBPABYBWWXDV-NSHDSACASA-N 0.000 claims description 3
- KNIWJMQHIOPAIF-UHFFFAOYSA-N 4-(ethoxyamino)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(NOCC)CC21CCC2 KNIWJMQHIOPAIF-UHFFFAOYSA-N 0.000 claims description 3
- JEWMSEQZYRVOFR-UHFFFAOYSA-N 4-(ethoxyamino)-5-ethyl-7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(CC)=C2C(NOCC)CC21CCC2 JEWMSEQZYRVOFR-UHFFFAOYSA-N 0.000 claims description 3
- RQFOJBBNJOAJAP-UHFFFAOYSA-N 4-(methoxyamino)-5,7-dimethylspiro[3,4-dihydrothiochromene-2,1'-cyclobutane]-6-ol Chemical compound S1C2=CC(C)=C(O)C(C)=C2C(NOC)CC21CCC2 RQFOJBBNJOAJAP-UHFFFAOYSA-N 0.000 claims description 3
- WOEFXDGFBDFTIB-UHFFFAOYSA-N 5,7-diethyl-4-(methoxyamino)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(NOC)C=2C(CC)=C(O)C(CC)=CC=2OC21CCC2 WOEFXDGFBDFTIB-UHFFFAOYSA-N 0.000 claims description 3
- WKFWCMBXXNFBFN-UHFFFAOYSA-N 5-ethyl-4-(methoxyamino)-7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(NOC)C=2C(CC)=C(O)C(C)=C(C)C=2OC21CCC2 WKFWCMBXXNFBFN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- MOCSSRCMDQWICJ-UHFFFAOYSA-N (4-amino-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl) acetate Chemical compound C1C(N)C2=C(C)C(OC(=O)C)=C(C)C(C)=C2OC21CCC2 MOCSSRCMDQWICJ-UHFFFAOYSA-N 0.000 claims description 2
- BSSIPABUORAFOE-SFQUDFHCSA-N (4e)-4-ethoxyimino-5,7-dimethylspiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(=N/OCC)/CC21CCC2 BSSIPABUORAFOE-SFQUDFHCSA-N 0.000 claims description 2
- BSSIPABUORAFOE-ATVHPVEESA-N (4z)-4-ethoxyimino-5,7-dimethylspiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(=N/OCC)\CC21CCC2 BSSIPABUORAFOE-ATVHPVEESA-N 0.000 claims description 2
- DTJVDBAKBVBYEK-UHFFFAOYSA-N 2-(7-chloro-5,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl)oxy-n,n-dimethylpropan-1-amine Chemical compound O1C=2C(C)=C(Cl)C(OC(CN(C)C)C)=C(C)C=2CCC21CCC2 DTJVDBAKBVBYEK-UHFFFAOYSA-N 0.000 claims description 2
- HAIMWYMFNPDKEF-UHFFFAOYSA-N 3-[3-[(methoxyamino)methyl]-5,7-dimethylspiro[chromene-2,1'-cyclobutane]-6-yl]-2,2-dimethylpropanoic acid Chemical compound CONCC1=CC2=C(C)C(CC(C)(C)C(O)=O)=C(C)C=C2OC11CCC1 HAIMWYMFNPDKEF-UHFFFAOYSA-N 0.000 claims description 2
- DZLPVHWNDJTWBU-UHFFFAOYSA-N 3-methoxy-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound COC1CC2=C(C)C(O)=C(C)C(C)=C2OC11CCC1 DZLPVHWNDJTWBU-UHFFFAOYSA-N 0.000 claims description 2
- UVOWYMQHYRRDED-UHFFFAOYSA-N 4-(aminomethyl)-5,7,8-trimethylspiro[3h-chromene-2,1'-cyclobutane]-4,6-diol Chemical compound C1C(O)(CN)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 UVOWYMQHYRRDED-UHFFFAOYSA-N 0.000 claims description 2
- TUWHBODODHQFCM-UHFFFAOYSA-N 4-(cyclopropylamino)-5,7,8-trimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound C1CC1NC1C=2C(C)=C(O)C(C)=C(C)C=2OCC21CCC2 TUWHBODODHQFCM-UHFFFAOYSA-N 0.000 claims description 2
- VJTDEIQUFPFEHI-UHFFFAOYSA-N 4-(ethoxyamino)-5,7-diethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(CC)=C(O)C(CC)=C2C(NOCC)CC21CCC2 VJTDEIQUFPFEHI-UHFFFAOYSA-N 0.000 claims description 2
- DKRHEVFTFMZHPC-UHFFFAOYSA-N 4-(hexylamino)-5,7,8-trimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound CCCCCCNC1C2=C(C)C(O)=C(C)C(C)=C2OCC11CCC1 DKRHEVFTFMZHPC-UHFFFAOYSA-N 0.000 claims description 2
- WZWOQKKQXRBNKJ-UHFFFAOYSA-N 4-(hydroxyamino)-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(NO)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 WZWOQKKQXRBNKJ-UHFFFAOYSA-N 0.000 claims description 2
- ZTXCQHMVLXSVRQ-UHFFFAOYSA-N 4-(hydroxyamino)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(NO)C=2C(C)=C(O)C(C)=CC=2OC21CCC2 ZTXCQHMVLXSVRQ-UHFFFAOYSA-N 0.000 claims description 2
- ORCNEZFZBVBIQH-UHFFFAOYSA-N 4-(methoxyamino)-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(NOC)CC21CCC2 ORCNEZFZBVBIQH-UHFFFAOYSA-N 0.000 claims description 2
- XACDSQSIKFAHOP-UHFFFAOYSA-N 4-[hydroxy(methyl)amino]-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(N(O)C)CC21CCC2 XACDSQSIKFAHOP-UHFFFAOYSA-N 0.000 claims description 2
- SMZJNHFDMJHPES-UHFFFAOYSA-N 4-[hydroxy(methyl)amino]-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(N(O)C)CC21CCC2 SMZJNHFDMJHPES-UHFFFAOYSA-N 0.000 claims description 2
- IKIFQQDWVFIUBL-UHFFFAOYSA-N 4-[methoxy(methyl)amino]-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(N(C)OC)CC21CCC2 IKIFQQDWVFIUBL-UHFFFAOYSA-N 0.000 claims description 2
- YWDOVSYHLFCZIQ-UHFFFAOYSA-N 4-ethoxyimino-5,7,8-trimethylspiro[3h-thiochromene-2,1'-cyclobutane]-6-ol Chemical compound S1C2=C(C)C(C)=C(O)C(C)=C2C(=NOCC)CC21CCC2 YWDOVSYHLFCZIQ-UHFFFAOYSA-N 0.000 claims description 2
- YNCHVBPKTVUBFJ-UHFFFAOYSA-N 4-ethoxyimino-5,7-diethylspiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(CC)=C(O)C(CC)=C2C(=NOCC)CC21CCC2 YNCHVBPKTVUBFJ-UHFFFAOYSA-N 0.000 claims description 2
- GXKYFYVANBSJKP-UHFFFAOYSA-N 4-ethoxyimino-5,7-dimethylspiro[3h-thiochromene-2,1'-cyclobutane]-6-ol Chemical compound S1C2=CC(C)=C(O)C(C)=C2C(=NOCC)CC21CCC2 GXKYFYVANBSJKP-UHFFFAOYSA-N 0.000 claims description 2
- OKNQEWFEQIVEHR-UHFFFAOYSA-N 4-hydroxyimino-5,7,8-trimethylspiro[3H-chromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(=NO)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 OKNQEWFEQIVEHR-UHFFFAOYSA-N 0.000 claims description 2
- BKTVUNZNMNHCHZ-UHFFFAOYSA-N 4-hydroxyimino-5,7-dimethylspiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(=NO)C=2C(C)=C(O)C(C)=CC=2OC21CCC2 BKTVUNZNMNHCHZ-UHFFFAOYSA-N 0.000 claims description 2
- APCVLZGYMILZMP-UHFFFAOYSA-N 4-imidazol-1-yl-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(N2C=NC=C2)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 APCVLZGYMILZMP-UHFFFAOYSA-N 0.000 claims description 2
- VHNGHFYTHSRWNP-UHFFFAOYSA-N 4-methoxyimino-5,7,8-trimethylspiro[3h-thiochromene-2,1'-cyclobutane]-6-ol Chemical compound S1C2=C(C)C(C)=C(O)C(C)=C2C(=NOC)CC21CCC2 VHNGHFYTHSRWNP-UHFFFAOYSA-N 0.000 claims description 2
- NFGPGJVQRKVRLC-UHFFFAOYSA-N 4-methoxyimino-5,7-dimethylspiro[3h-thiochromene-2,1'-cyclobutane]-6-ol Chemical compound S1C2=CC(C)=C(O)C(C)=C2C(=NOC)CC21CCC2 NFGPGJVQRKVRLC-UHFFFAOYSA-N 0.000 claims description 2
- JFSUCZNVOUJMIF-UHFFFAOYSA-N 5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-3,6-diol Chemical compound OC1CC=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 JFSUCZNVOUJMIF-UHFFFAOYSA-N 0.000 claims description 2
- IUHHMLKCDWMOPD-UHFFFAOYSA-N 5,7-diethyl-4-hydroxyiminospiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(=NO)C=2C(CC)=C(O)C(CC)=CC=2OC21CCC2 IUHHMLKCDWMOPD-UHFFFAOYSA-N 0.000 claims description 2
- QVHXYTGOEQCYHM-UHFFFAOYSA-N 5,7-diethyl-4-methoxyiminospiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(=NOC)C=2C(CC)=C(O)C(CC)=CC=2OC21CCC2 QVHXYTGOEQCYHM-UHFFFAOYSA-N 0.000 claims description 2
- SERGPKFPFZVPHF-UHFFFAOYSA-N 5,7-dimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound C1=CC=2C(C)=C(O)C(C)=CC=2OC21CCC2 SERGPKFPFZVPHF-UHFFFAOYSA-N 0.000 claims description 2
- LJTZCUQZROPSSR-UHFFFAOYSA-N 5-[1-(ethoxyamino)ethyl]-7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C(C)NOCC)=C(O)C(C)=C(C)C=2OC21CCC2 LJTZCUQZROPSSR-UHFFFAOYSA-N 0.000 claims description 2
- ZDCKCMTXOORMJM-UHFFFAOYSA-N 8-(5-butyl-1,2-oxazol-3-yl)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C(CCCC)=CC(C=2C=3OC4(CCC4)CCC=3C(C)=C(O)C=2C)=N1 ZDCKCMTXOORMJM-UHFFFAOYSA-N 0.000 claims description 2
- XPVFCJDEVZYLHA-UHFFFAOYSA-N 8-[(ethoxyamino)methyl]-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C=2C(CNOCC)=C(C)C(O)=C(C)C=2CCC21CCC2 XPVFCJDEVZYLHA-UHFFFAOYSA-N 0.000 claims description 2
- SHOJZCHBTCZJGG-UHFFFAOYSA-N CC1=C2CCC3(OC2=C(C(=C1O)C)C=C)CCC3.CONCC=3C(=C(C(=C1CCC2(OC31)CCC2)C)O)C Chemical compound CC1=C2CCC3(OC2=C(C(=C1O)C)C=C)CCC3.CONCC=3C(=C(C(=C1CCC2(OC31)CCC2)C)O)C SHOJZCHBTCZJGG-UHFFFAOYSA-N 0.000 claims description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
- FKZBOUXYKZNXKP-UHFFFAOYSA-N [4-(methoxyamino)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl] acetate Chemical compound O1C2=CC(C)=C(OC(C)=O)C(C)=C2C(NOC)CC21CCC2 FKZBOUXYKZNXKP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- JPLMYQNPWCCGDL-UHFFFAOYSA-N methyl 3-(6-hydroxy-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-8-yl)-4,5-dihydro-1,2-oxazole-5-carboxylate Chemical compound O1C(C(=O)OC)CC(C=2C=3OC4(CCC4)CCC=3C(C)=C(O)C=2C)=N1 JPLMYQNPWCCGDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- YCXCSAANUXLDGL-UHFFFAOYSA-N spiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound OC=1C=C2C=CC3(OC2=CC1)CCC3 YCXCSAANUXLDGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 28
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 27
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 17
- 150000001721 carbon Chemical group 0.000 claims 12
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 5
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 3
- 125000003368 amide group Chemical group 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- FXIBPABYBWWXDV-LLVKDONJSA-N (4r)-4-(methoxyamino)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C([C@H](C1=C(C)C(O)=C(C)C=C1O1)NOC)C21CCC2 FXIBPABYBWWXDV-LLVKDONJSA-N 0.000 claims 2
- MNPMYDQPBOUMLS-GFCCVEGCSA-N (4r)-5,7-diethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C=1([C@H](O)C2)C(CC)=C(O)C(CC)=CC=1OC12CCC1 MNPMYDQPBOUMLS-GFCCVEGCSA-N 0.000 claims 2
- MMGSNHSABRGBBA-GFCCVEGCSA-N (4r)-5-methyl-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C=1([C@H](O)C2)C(C)=C(O)C(C(C)C)=CC=1OC12CCC1 MMGSNHSABRGBBA-GFCCVEGCSA-N 0.000 claims 2
- MNPMYDQPBOUMLS-LBPRGKRZSA-N (4s)-5,7-diethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C=1([C@@H](O)C2)C(CC)=C(O)C(CC)=CC=1OC12CCC1 MNPMYDQPBOUMLS-LBPRGKRZSA-N 0.000 claims 2
- MMGSNHSABRGBBA-LBPRGKRZSA-N (4s)-5-methyl-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C=1([C@@H](O)C2)C(C)=C(O)C(C(C)C)=CC=1OC12CCC1 MMGSNHSABRGBBA-LBPRGKRZSA-N 0.000 claims 2
- ANZADMTUXLXLQO-UHFFFAOYSA-N 3-[(methoxyamino)methyl]-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound CONCC1CC2=C(C)C(O)=C(C)C=C2OC11CCC1 ANZADMTUXLXLQO-UHFFFAOYSA-N 0.000 claims 2
- HGWSCIKKEAITAY-UHFFFAOYSA-N 4-(ethoxyamino)-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(NOCC)CC21CCC2 HGWSCIKKEAITAY-UHFFFAOYSA-N 0.000 claims 2
- NHVOOXDUBXLMJN-UHFFFAOYSA-N 4-(ethoxyamino)-5,7,8-trimethylspiro[3,4-dihydrothiochromene-2,1'-cyclobutane]-6-ol Chemical compound S1C2=C(C)C(C)=C(O)C(C)=C2C(NOCC)CC21CCC2 NHVOOXDUBXLMJN-UHFFFAOYSA-N 0.000 claims 2
- TVOWSFFLXQMZIJ-UHFFFAOYSA-N 4-(ethoxyamino)-5,7-dimethylspiro[3,4-dihydrothiochromene-2,1'-cyclobutane]-6-ol Chemical compound S1C2=CC(C)=C(O)C(C)=C2C(NOCC)CC21CCC2 TVOWSFFLXQMZIJ-UHFFFAOYSA-N 0.000 claims 2
- WXRDYARUUPOTBM-UHFFFAOYSA-N 4-(methoxyamino)-5,7,8-trimethylspiro[3,4-dihydrothiochromene-2,1'-cyclobutane]-6-ol Chemical compound S1C2=C(C)C(C)=C(O)C(C)=C2C(NOC)CC21CCC2 WXRDYARUUPOTBM-UHFFFAOYSA-N 0.000 claims 2
- FXIBPABYBWWXDV-UHFFFAOYSA-N 4-(methoxyamino)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(NOC)CC21CCC2 FXIBPABYBWWXDV-UHFFFAOYSA-N 0.000 claims 2
- MUJMGFIMIGFVAZ-UHFFFAOYSA-N 4-(methoxyamino)-5-methyl-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C(C)C)=C(O)C(C)=C2C(NOC)CC21CCC2 MUJMGFIMIGFVAZ-UHFFFAOYSA-N 0.000 claims 2
- USEXRZLHTICOHA-UHFFFAOYSA-N 4-(methoxyamino)-7,8-dimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound CONC1C2=CC(O)=C(C)C(C)=C2OCC11CCC1 USEXRZLHTICOHA-UHFFFAOYSA-N 0.000 claims 2
- WAESAADGKFATQX-UHFFFAOYSA-N 4-[ethyl(methoxy)amino]-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(N(OC)CC)CC21CCC2 WAESAADGKFATQX-UHFFFAOYSA-N 0.000 claims 2
- RPNYYPMWSVCCGP-UHFFFAOYSA-N 4-methoxy-3,5,7,8-tetramethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(OC)C(C)C21CCC2 RPNYYPMWSVCCGP-UHFFFAOYSA-N 0.000 claims 2
- GOJNZJWROIVLEF-UHFFFAOYSA-N 5,7,8-trimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-4,6-diol Chemical compound OC1C=2C(C)=C(O)C(C)=C(C)C=2OCC21CCC2 GOJNZJWROIVLEF-UHFFFAOYSA-N 0.000 claims 2
- MVLAFRAXKGTXPI-UHFFFAOYSA-N 5,7,8-trimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound C1C=2C(C)=C(O)C(C)=C(C)C=2OCC21CCC2 MVLAFRAXKGTXPI-UHFFFAOYSA-N 0.000 claims 2
- NGCHQTKHVCBDOJ-UHFFFAOYSA-N 5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C1C(O)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 NGCHQTKHVCBDOJ-UHFFFAOYSA-N 0.000 claims 2
- YHHQCUDVVOQNLF-UHFFFAOYSA-N 5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclopropane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC21CC2 YHHQCUDVVOQNLF-UHFFFAOYSA-N 0.000 claims 2
- UQGHCHJDDXOXIX-UHFFFAOYSA-N 5,7-diethyl-8-(hydroxymethyl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(CO)C(CC)=C(O)C(CC)=C2CCC21CCC2 UQGHCHJDDXOXIX-UHFFFAOYSA-N 0.000 claims 2
- FTKRQZCWKOIWJC-UHFFFAOYSA-N 5,7-diethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-4,6-diol Chemical compound OC1C=2C(CC)=C(O)C(CC)=CC=2OCC21CCC2 FTKRQZCWKOIWJC-UHFFFAOYSA-N 0.000 claims 2
- YSMVBQZURLGASL-UHFFFAOYSA-N 5,7-diethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(CC)=C(O)C(CC)=CC=2OC21CCC2 YSMVBQZURLGASL-UHFFFAOYSA-N 0.000 claims 2
- LPAXSJAAUAOBLN-UHFFFAOYSA-N 5,7-dimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-4,6-diol Chemical compound OC1C=2C(C)=C(O)C(C)=CC=2OCC21CCC2 LPAXSJAAUAOBLN-UHFFFAOYSA-N 0.000 claims 2
- ADIUTYZRPHXCRZ-UHFFFAOYSA-N 5,7-dimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound C1C=2C(C)=C(O)C(C)=CC=2OCC21CCC2 ADIUTYZRPHXCRZ-UHFFFAOYSA-N 0.000 claims 2
- ONJXCJNGQIFLMC-UHFFFAOYSA-N 5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C1C(O)C=2C(C)=C(O)C(C)=CC=2OC21CCC2 ONJXCJNGQIFLMC-UHFFFAOYSA-N 0.000 claims 2
- PVIZFOZWIVXUFE-UHFFFAOYSA-N 5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(C)=CC=2OC21CCC2 PVIZFOZWIVXUFE-UHFFFAOYSA-N 0.000 claims 2
- WHSNDLZESRSIRX-UHFFFAOYSA-N 5-ethyl-4-(methoxyamino)-7-methylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(NOC)C=2C(CC)=C(O)C(C)=CC=2OC21CCC2 WHSNDLZESRSIRX-UHFFFAOYSA-N 0.000 claims 2
- JZFBZFMRQDCINT-UHFFFAOYSA-N 5-ethyl-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C1C(O)C=2C(CC)=C(O)C(C(C)C)=CC=2OC21CCC2 JZFBZFMRQDCINT-UHFFFAOYSA-N 0.000 claims 2
- CQYMODRDPROCTE-UHFFFAOYSA-N 5-methyl-7-propan-2-ylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-4,6-diol Chemical compound OC1C=2C(C)=C(O)C(C(C)C)=CC=2OCC21CCC2 CQYMODRDPROCTE-UHFFFAOYSA-N 0.000 claims 2
- MMGSNHSABRGBBA-UHFFFAOYSA-N 5-methyl-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C1C(O)C=2C(C)=C(O)C(C(C)C)=CC=2OC21CCC2 MMGSNHSABRGBBA-UHFFFAOYSA-N 0.000 claims 2
- VXGPQICKKDMQRT-UHFFFAOYSA-N 5-methyl-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(C(C)C)=CC=2OC21CCC2 VXGPQICKKDMQRT-UHFFFAOYSA-N 0.000 claims 2
- MXKQOKFZBLSIQC-UHFFFAOYSA-N 7,8-dimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-4,6-diol Chemical compound C1OC2=C(C)C(C)=C(O)C=C2C(O)C21CCC2 MXKQOKFZBLSIQC-UHFFFAOYSA-N 0.000 claims 2
- CCEHQCGVZYGVPE-UHFFFAOYSA-N 7,8-dimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound C1C=2C=C(O)C(C)=C(C)C=2OCC21CCC2 CCEHQCGVZYGVPE-UHFFFAOYSA-N 0.000 claims 2
- URIJPPXOVQGIBP-UHFFFAOYSA-N 7,8-dimethylspiro[2,4-dihydrochromene-3,1'-cyclopropane]-6-ol Chemical compound C1C=2C=C(O)C(C)=C(C)C=2OCC21CC2 URIJPPXOVQGIBP-UHFFFAOYSA-N 0.000 claims 2
- DHYFSFUVHCDQOV-UHFFFAOYSA-N 7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C=C(O)C(C)=C(C)C=2OC21CCC2 DHYFSFUVHCDQOV-UHFFFAOYSA-N 0.000 claims 2
- PEOLDABYTUHWLA-UHFFFAOYSA-N 7-ethyl-4-(methoxyamino)-5-methylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(NOC)C=2C(C)=C(O)C(CC)=CC=2OC21CCC2 PEOLDABYTUHWLA-UHFFFAOYSA-N 0.000 claims 2
- PEMBJGHOJNYANJ-UHFFFAOYSA-N 7-tert-butyl-5-methylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C1C(O)C=2C(C)=C(O)C(C(C)(C)C)=CC=2OC21CCC2 PEMBJGHOJNYANJ-UHFFFAOYSA-N 0.000 claims 2
- TZABBNXHWDVQCM-UHFFFAOYSA-N 7-tert-butyl-5-methylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(C(C)(C)C)=CC=2OC21CCC2 TZABBNXHWDVQCM-UHFFFAOYSA-N 0.000 claims 2
- OIMWCAWWOZEJMP-UHFFFAOYSA-N 8-chloro-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(Cl)C(C)=C(O)C(C)=C2CCC21CCC2 OIMWCAWWOZEJMP-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- AELKGROHZIMNCC-UHFFFAOYSA-N (7-tert-butyl-4-hydroxy-5-methylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl) acetate Chemical compound O1C=2C=C(C(C)(C)C)C(OC(=O)C)=C(C)C=2C(O)CC21CCC2 AELKGROHZIMNCC-UHFFFAOYSA-N 0.000 claims 1
- LLFVBPNVHURODG-UHFFFAOYSA-N 2,2,5,7,8-pentamethylspiro[3h-thiochromene-4,1'-cyclobutane]-6-ol Chemical compound C1=2C(C)=C(O)C(C)=C(C)C=2SC(C)(C)CC21CCC2 LLFVBPNVHURODG-UHFFFAOYSA-N 0.000 claims 1
- AWUYBNVAYZMSPW-UHFFFAOYSA-N 2-(7-chloro-5,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl)oxy-n,n-dimethylethanamine Chemical compound O1C=2C(C)=C(Cl)C(OCCN(C)C)=C(C)C=2CCC21CCC2 AWUYBNVAYZMSPW-UHFFFAOYSA-N 0.000 claims 1
- SVYCHMYHICETQK-UHFFFAOYSA-N 2-[(5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl)oxymethyl]pyridine Chemical compound C1CC=2C(C)=C(OCC=3N=CC=CC=3)C(C)=C(C)C=2OC21CCC2 SVYCHMYHICETQK-UHFFFAOYSA-N 0.000 claims 1
- HTRXKYOSYUQJDU-UHFFFAOYSA-N 2-[(5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl)oxymethyl]quinoline Chemical compound C1CC=2C(C)=C(OCC=3N=C4C=CC=CC4=CC=3)C(C)=C(C)C=2OC21CCC2 HTRXKYOSYUQJDU-UHFFFAOYSA-N 0.000 claims 1
- HYLKRHAQFLDTCF-UHFFFAOYSA-N 2-hydroxy-2-[6-hydroxy-5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-8-yl]acetonitrile Chemical compound C1CC=2C(C(C)C)=C(O)C(C(C)C)=C(C(O)C#N)C=2OC21CCC2 HYLKRHAQFLDTCF-UHFFFAOYSA-N 0.000 claims 1
- NCXZQWZJSHFPND-UHFFFAOYSA-N 3,5,7,8-tetramethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound CC1C(O)C2=C(C)C(O)=C(C)C(C)=C2OC11CCC1 NCXZQWZJSHFPND-UHFFFAOYSA-N 0.000 claims 1
- OIWXYLDFTQJVCG-UHFFFAOYSA-N 3,5,7,8-tetramethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound CC1=CC2=C(C)C(O)=C(C)C(C)=C2OC11CCC1 OIWXYLDFTQJVCG-UHFFFAOYSA-N 0.000 claims 1
- IICOKOVEQGUOGI-UHFFFAOYSA-N 3-(1-hydroxyethyl)-5,7,8-trimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound CC(O)C1=CC2=C(C)C(O)=C(C)C(C)=C2OC11CCC1 IICOKOVEQGUOGI-UHFFFAOYSA-N 0.000 claims 1
- URGPNBYTUDDNHT-UHFFFAOYSA-N 3-(1-methoxyethyl)-5,7,8-trimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound COC(C)C1=CC2=C(C)C(O)=C(C)C(C)=C2OC11CCC1 URGPNBYTUDDNHT-UHFFFAOYSA-N 0.000 claims 1
- XODCBXRUVVRNKF-UHFFFAOYSA-N 3-(ethoxyiminomethyl)-5,7-dimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound CCON=CC1=CC2=C(C)C(O)=C(C)C=C2OC11CCC1 XODCBXRUVVRNKF-UHFFFAOYSA-N 0.000 claims 1
- QKUAQBBOOWLNKZ-UHFFFAOYSA-N 3-(hydroxymethyl)-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound OCC1CC=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 QKUAQBBOOWLNKZ-UHFFFAOYSA-N 0.000 claims 1
- GCLKMNRUYBXRKY-UHFFFAOYSA-N 3-(hydroxymethyl)-5,7,8-trimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound OCC1=CC=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 GCLKMNRUYBXRKY-UHFFFAOYSA-N 0.000 claims 1
- NKATUNITGWXONH-UHFFFAOYSA-N 3-(methoxyiminomethyl)-5,7-dimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound CON=CC1=CC2=C(C)C(O)=C(C)C=C2OC11CCC1 NKATUNITGWXONH-UHFFFAOYSA-N 0.000 claims 1
- YIJKZEZMLFKPAV-UHFFFAOYSA-N 3-(methoxymethyl)-5,7,8-trimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound COCC1=CC2=C(C)C(O)=C(C)C(C)=C2OC11CCC1 YIJKZEZMLFKPAV-UHFFFAOYSA-N 0.000 claims 1
- LQIAYKIAOMSRHI-UHFFFAOYSA-N 3-[(ethoxyamino)methyl]-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound CCONCC1CC2=C(C)C(O)=C(C)C=C2OC11CCC1 LQIAYKIAOMSRHI-UHFFFAOYSA-N 0.000 claims 1
- RPTBJHJYAHEXIA-UHFFFAOYSA-N 3-[(ethoxyamino)methyl]-5,7-dimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound CCONCC1=CC2=C(C)C(O)=C(C)C=C2OC11CCC1 RPTBJHJYAHEXIA-UHFFFAOYSA-N 0.000 claims 1
- HEGXLOXVALDPKP-UHFFFAOYSA-N 3-[(methoxyamino)methyl]-5,7-dimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound CONCC1=CC2=C(C)C(O)=C(C)C=C2OC11CCC1 HEGXLOXVALDPKP-UHFFFAOYSA-N 0.000 claims 1
- PNNWSWKDLKMUIT-UHFFFAOYSA-N 4-(aminomethyl)-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(CN)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 PNNWSWKDLKMUIT-UHFFFAOYSA-N 0.000 claims 1
- SWDXNDMVODMOKY-UHFFFAOYSA-N 4-(aminomethyl)-5,7,8-trimethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound C1=C(CN)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 SWDXNDMVODMOKY-UHFFFAOYSA-N 0.000 claims 1
- IMJFGHZYJRQNFS-UHFFFAOYSA-N 4-(diethylaminomethyl)-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(CN(CC)CC)CC21CCC2 IMJFGHZYJRQNFS-UHFFFAOYSA-N 0.000 claims 1
- VXJRXBCDWVVREQ-UHFFFAOYSA-N 4-(ethoxyamino)-7,8-dimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound CCONC1C2=CC(O)=C(C)C(C)=C2OCC11CCC1 VXJRXBCDWVVREQ-UHFFFAOYSA-N 0.000 claims 1
- PEIKIKYYXVNQEU-UHFFFAOYSA-N 4-(ethoxyamino)-7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C=C2C(NOCC)CC21CCC2 PEIKIKYYXVNQEU-UHFFFAOYSA-N 0.000 claims 1
- CFNYVSHQVGSBEX-UHFFFAOYSA-N 4-(ethylaminomethyl)-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(CNCC)CC21CCC2 CFNYVSHQVGSBEX-UHFFFAOYSA-N 0.000 claims 1
- GGIBGSPQHMXJEH-UHFFFAOYSA-N 4-(methoxyamino)-7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C=C2C(NOC)CC21CCC2 GGIBGSPQHMXJEH-UHFFFAOYSA-N 0.000 claims 1
- WIUOOZSOXSTIJD-UHFFFAOYSA-N 4-[methoxy(methyl)amino]-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(N(C)OC)CC21CCC2 WIUOOZSOXSTIJD-UHFFFAOYSA-N 0.000 claims 1
- KAXSLFXPPBQZOD-UHFFFAOYSA-N 4-ethoxy-5,7,8-trimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound CCOC1C2=C(C)C(O)=C(C)C(C)=C2OCC11CCC1 KAXSLFXPPBQZOD-UHFFFAOYSA-N 0.000 claims 1
- WPMOXVAEIRGPNS-UHFFFAOYSA-N 4-ethoxy-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(OCC)CC21CCC2 WPMOXVAEIRGPNS-UHFFFAOYSA-N 0.000 claims 1
- SXBKBOBSDORYMW-UHFFFAOYSA-N 4-ethoxy-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(OCC)CC21CCC2 SXBKBOBSDORYMW-UHFFFAOYSA-N 0.000 claims 1
- FXUFPPHRRUDZEH-UHFFFAOYSA-N 4-ethoxyimino-5-ethyl-7,8-dimethylspiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(CC)=C2C(=NOCC)CC21CCC2 FXUFPPHRRUDZEH-UHFFFAOYSA-N 0.000 claims 1
- RLJPLSYRINIVDQ-UHFFFAOYSA-N 4-methoxy-5,7,8-trimethylspiro[2,4-dihydrochromene-3,1'-cyclobutane]-6-ol Chemical compound COC1C2=C(C)C(O)=C(C)C(C)=C2OCC11CCC1 RLJPLSYRINIVDQ-UHFFFAOYSA-N 0.000 claims 1
- YJUIJRBXKKFHCV-UHFFFAOYSA-N 4-methoxy-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(OC)CC21CCC2 YJUIJRBXKKFHCV-UHFFFAOYSA-N 0.000 claims 1
- GAVLHGAOYXGNIT-UHFFFAOYSA-N 4-methoxy-5-methyl-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C(C)C)=C(O)C(C)=C2C(OC)CC21CCC2 GAVLHGAOYXGNIT-UHFFFAOYSA-N 0.000 claims 1
- RFSURKRBHFOAAC-UHFFFAOYSA-N 4-methoxyimino-5,7-dimethylspiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(=NOC)CC21CCC2 RFSURKRBHFOAAC-UHFFFAOYSA-N 0.000 claims 1
- ZWSVOZADTKJOEY-UHFFFAOYSA-N 4-methoxyimino-7,8-dimethylspiro[2h-chromene-3,1'-cyclopropane]-6-ol Chemical compound CON=C1C2=CC(O)=C(C)C(C)=C2OCC11CC1 ZWSVOZADTKJOEY-UHFFFAOYSA-N 0.000 claims 1
- KHUFIIYIFNLESQ-UHFFFAOYSA-N 5',7',8'-trimethylspiro[cyclobutane-1,2'-thiochromene]-6'-ol Chemical compound C1=CC=2C(C)=C(O)C(C)=C(C)C=2SC21CCC2 KHUFIIYIFNLESQ-UHFFFAOYSA-N 0.000 claims 1
- UPGVUYBBSQSNGG-UHFFFAOYSA-N 5,7,8-trimethyl-1,1-dioxospiro[2,3-dihydrothiochromene-4,1'-cyclobutane]-6-ol Chemical compound CC1=C(O)C(C)=C(C)C(S(CC2)(=O)=O)=C1C12CCC1 UPGVUYBBSQSNGG-UHFFFAOYSA-N 0.000 claims 1
- RUBZJKUPXGTRHX-UHFFFAOYSA-N 5,7,8-trimethyl-1-oxospiro[2,3-dihydrothiochromene-4,1'-cyclobutane]-6-ol Chemical compound CC1=C(O)C(C)=C(C)C(S(CC2)=O)=C1C12CCC1 RUBZJKUPXGTRHX-UHFFFAOYSA-N 0.000 claims 1
- WJUJKXBKUQYSOY-UHFFFAOYSA-N 5,7,8-trimethyl-3-(morpholin-4-ylmethyl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound C1COCCN1CC1C(O)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 WJUJKXBKUQYSOY-UHFFFAOYSA-N 0.000 claims 1
- OXXPHVFZIVJDHH-UHFFFAOYSA-N 5,7,8-trimethyl-4-morpholin-4-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(N2CCOCC2)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 OXXPHVFZIVJDHH-UHFFFAOYSA-N 0.000 claims 1
- HSKMPEJXSLTVDG-UHFFFAOYSA-N 5,7,8-trimethyl-4-propan-2-ylsulfanylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(SC(C)C)CC21CCC2 HSKMPEJXSLTVDG-UHFFFAOYSA-N 0.000 claims 1
- YWGXLJDDLDJJAE-UHFFFAOYSA-N 5,7,8-trimethyl-4-pyrrolidin-1-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(N2CCCC2)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 YWGXLJDDLDJJAE-UHFFFAOYSA-N 0.000 claims 1
- BAYNTYBVEHOPFA-UHFFFAOYSA-N 5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 BAYNTYBVEHOPFA-UHFFFAOYSA-N 0.000 claims 1
- GUQZJFDQTPQZLI-UHFFFAOYSA-N 5,7,8-trimethylspiro[3,4-dihydrothiochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2SC21CCC2 GUQZJFDQTPQZLI-UHFFFAOYSA-N 0.000 claims 1
- YKYGCUUWCTZCCD-UHFFFAOYSA-N 5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C(C)C)=C(O)C(C(C)C)=CC=2OC21CCC2 YKYGCUUWCTZCCD-UHFFFAOYSA-N 0.000 claims 1
- OLSHFXUTIPTTGA-UHFFFAOYSA-N 5,7-di(propan-2-yl)spiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound C1=CC=2C(C(C)C)=C(O)C(C(C)C)=CC=2OC21CCC2 OLSHFXUTIPTTGA-UHFFFAOYSA-N 0.000 claims 1
- KHTDWKFOWQHJIB-UHFFFAOYSA-N 5,7-diethyl-3-(hydroxymethyl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound OCC1CC=2C(CC)=C(O)C(CC)=CC=2OC21CCC2 KHTDWKFOWQHJIB-UHFFFAOYSA-N 0.000 claims 1
- QAUJPSNHDSKMCE-UHFFFAOYSA-N 5,7-diethylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound C1=CC=2C(CC)=C(O)C(CC)=CC=2OC21CCC2 QAUJPSNHDSKMCE-UHFFFAOYSA-N 0.000 claims 1
- UCTQIWCXACADOU-UHFFFAOYSA-N 5,7-dimethyl-3-(1,3-oxazol-5-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C=1N=COC=1C1CC=2C(C)=C(O)C(C)=CC=2OC21CCC2 UCTQIWCXACADOU-UHFFFAOYSA-N 0.000 claims 1
- UGBYQJYAUMWTED-UHFFFAOYSA-N 5,7-dimethyl-3-(1,3-oxazol-5-yl)spiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound C=1N=COC=1C1=CC=2C(C)=C(O)C(C)=CC=2OC21CCC2 UGBYQJYAUMWTED-UHFFFAOYSA-N 0.000 claims 1
- CENTVCTVCWVMMT-UHFFFAOYSA-N 5,7-dimethyl-4-propan-2-yloxyspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(OC(C)C)CC21CCC2 CENTVCTVCWVMMT-UHFFFAOYSA-N 0.000 claims 1
- FOVPZYJONFQOGU-UHFFFAOYSA-N 5,7-dimethyl-8-(1,3-oxazol-5-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1=2OC3(CCC3)CCC=2C(C)=C(O)C(C)=C1C1=CN=CO1 FOVPZYJONFQOGU-UHFFFAOYSA-N 0.000 claims 1
- ALRGKHLOQAIFLG-UHFFFAOYSA-N 5,8-dimethyl-7-(2-quinolin-2-ylethyl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(CCC=3N=C4C=CC=CC4=CC=3)=C(C)C=2OC21CCC2 ALRGKHLOQAIFLG-UHFFFAOYSA-N 0.000 claims 1
- LFIDMLFBHKIZPY-UHFFFAOYSA-N 5,8-dimethyl-7-(3-methylbutyl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(CCC(C)C)=C(C)C=2OC21CCC2 LFIDMLFBHKIZPY-UHFFFAOYSA-N 0.000 claims 1
- GFHPUKXKYGNHQX-UHFFFAOYSA-N 5-(3,7-dimethylocta-2,6-dienyl)-7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(CC=C(C)CCC=C(C)C)=C(O)C(C)=C(C)C=2OC21CCC2 GFHPUKXKYGNHQX-UHFFFAOYSA-N 0.000 claims 1
- JQIDLWCOBSHMHE-UHFFFAOYSA-N 5-chloro-7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(Cl)=C(O)C(C)=C(C)C=2OC21CCC2 JQIDLWCOBSHMHE-UHFFFAOYSA-N 0.000 claims 1
- BTPLJJWEVWXLRF-UHFFFAOYSA-N 5-chloro-8-methylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C=2C(C)=CC(O)=C(Cl)C=2CCC21CCC2 BTPLJJWEVWXLRF-UHFFFAOYSA-N 0.000 claims 1
- RGSHEAYVXFRSAQ-UHFFFAOYSA-N 5-ethyl-4-methoxyimino-7,8-dimethylspiro[3h-chromene-2,1'-cyclobutane]-6-ol Chemical compound C1C(=NOC)C=2C(CC)=C(O)C(C)=C(C)C=2OC21CCC2 RGSHEAYVXFRSAQ-UHFFFAOYSA-N 0.000 claims 1
- CQDHBOMRQVZDBA-UHFFFAOYSA-N 5-methyl-7-propan-2-ylspiro[chromene-2,1'-cyclobutane]-6-ol Chemical compound C1=CC=2C(C)=C(O)C(C(C)C)=CC=2OC21CCC2 CQDHBOMRQVZDBA-UHFFFAOYSA-N 0.000 claims 1
- DXMDZYFBDDHJMJ-UHFFFAOYSA-N 5-methyl-8-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C=2C(C(C)C)=CC(O)=C(C)C=2CCC21CCC2 DXMDZYFBDDHJMJ-UHFFFAOYSA-N 0.000 claims 1
- UVTBPMQXNNFAOM-UHFFFAOYSA-N 6-hydroxy-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-carbonitrile Chemical compound C1C(C#N)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 UVTBPMQXNNFAOM-UHFFFAOYSA-N 0.000 claims 1
- XHNKRXZSRDSIMS-UHFFFAOYSA-N 6-hydroxy-5,7,8-trimethylspiro[3h-thiochromene-2,1'-cyclobutane]-4-one Chemical compound C1C(=O)C=2C(C)=C(O)C(C)=C(C)C=2SC21CCC2 XHNKRXZSRDSIMS-UHFFFAOYSA-N 0.000 claims 1
- HQCILAQBIRWRBP-UHFFFAOYSA-N 6-hydroxy-5,7,8-trimethylspiro[chromene-2,1'-cyclobutane]-4-carbonitrile Chemical compound C1=C(C#N)C=2C(C)=C(O)C(C)=C(C)C=2OC21CCC2 HQCILAQBIRWRBP-UHFFFAOYSA-N 0.000 claims 1
- DEDPIUBVWFKTAO-UHFFFAOYSA-N 6-hydroxy-5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-8-carbaldehyde Chemical compound C1CC=2C(C(C)C)=C(O)C(C(C)C)=C(C=O)C=2OC21CCC2 DEDPIUBVWFKTAO-UHFFFAOYSA-N 0.000 claims 1
- WVSRVCUNBICYCR-UHFFFAOYSA-N 7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4,6-diol Chemical compound O1C2=C(C)C(C)=C(O)C=C2C(O)CC21CCC2 WVSRVCUNBICYCR-UHFFFAOYSA-N 0.000 claims 1
- HAWALSMVJLNQRC-UHFFFAOYSA-N 7,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclopropane]-4,6-diol Chemical compound O1C2=C(C)C(C)=C(O)C=C2C(O)CC21CC2 HAWALSMVJLNQRC-UHFFFAOYSA-N 0.000 claims 1
- RPOOKALTYCPVAS-UHFFFAOYSA-N 7-(1-benzofuran-2-yl)-2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound O1C(C)(C)CCC2=C1C(C)=C(C=1OC3=CC=CC=C3C=1)C(O)=C2C RPOOKALTYCPVAS-UHFFFAOYSA-N 0.000 claims 1
- YWQMAVGZUDZNOJ-UHFFFAOYSA-N 7-(3,7-dimethylocta-2,6-dienyl)-5,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(CC=C(C)CCC=C(C)C)=C(C)C=2OC21CCC2 YWQMAVGZUDZNOJ-UHFFFAOYSA-N 0.000 claims 1
- OINDWDFGINBHNP-UHFFFAOYSA-N 7-(4,5-dimethyl-1H-imidazol-2-yl)-5,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound N1C(C)=C(C)N=C1C(C(=C1C)O)=C(C)C2=C1CCC1(CCC1)O2 OINDWDFGINBHNP-UHFFFAOYSA-N 0.000 claims 1
- LSRXHINOVMCIEG-UHFFFAOYSA-N 7-(5,6-dimethyl-1H-benzimidazol-2-yl)-5,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C(C(=C(C)C=1CC2)O)=C(C)C=1OC12CCC1 LSRXHINOVMCIEG-UHFFFAOYSA-N 0.000 claims 1
- NELKABHZJPECQX-UHFFFAOYSA-N 7-chloro-5,8-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(Cl)=C(C)C=2OC21CCC2 NELKABHZJPECQX-UHFFFAOYSA-N 0.000 claims 1
- FIKOCAHHMZIHQD-UHFFFAOYSA-N 7-tert-butyl-5-(morpholin-4-ylmethyl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(CN3CCOCC3)=C(O)C(C(C)(C)C)=CC=2OC21CCC2 FIKOCAHHMZIHQD-UHFFFAOYSA-N 0.000 claims 1
- DTEJOTKJDNOFIT-UHFFFAOYSA-N 8-(4,5-dimethyl-1h-imidazol-2-yl)-5,7-diethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1=2OC3(CCC3)CCC=2C(CC)=C(O)C(CC)=C1C1=NC(C)=C(C)N1 DTEJOTKJDNOFIT-UHFFFAOYSA-N 0.000 claims 1
- JJUXRXBJTROAMG-UHFFFAOYSA-N 8-(hydroxymethyl)-5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(CO)C(C(C)C)=C(O)C(C(C)C)=C2CCC21CCC2 JJUXRXBJTROAMG-UHFFFAOYSA-N 0.000 claims 1
- XAGVNUBHBAPVIC-UHFFFAOYSA-N 8-(hydroxymethyl)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(CO)C(C)=C(O)C(C)=C2CCC21CCC2 XAGVNUBHBAPVIC-UHFFFAOYSA-N 0.000 claims 1
- XRFVVUQHBIPUSU-UHFFFAOYSA-N 8-(hydroxymethyl)-5-methyl-7-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(CO)C(C(C)C)=C(O)C(C)=C2CCC21CCC2 XRFVVUQHBIPUSU-UHFFFAOYSA-N 0.000 claims 1
- BKKWEPXTGWXMBQ-UHFFFAOYSA-N 8-(methoxymethyl)-5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC2=C(C(C)C)C(O)=C(C(C)C)C(COC)=C2OC21CCC2 BKKWEPXTGWXMBQ-UHFFFAOYSA-N 0.000 claims 1
- ISZGXTCKNJSYAX-UHFFFAOYSA-N 8-(methoxymethyl)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C=2C(COC)=C(C)C(O)=C(C)C=2CCC21CCC2 ISZGXTCKNJSYAX-UHFFFAOYSA-N 0.000 claims 1
- DGCPYLDEUFPEIV-UHFFFAOYSA-N 8-[(hydroxyamino)methyl]-5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound O1C2=C(CNO)C(C(C)C)=C(O)C(C(C)C)=C2CCC21CCC2 DGCPYLDEUFPEIV-UHFFFAOYSA-N 0.000 claims 1
- PSQAEWRSNGCBBU-UHFFFAOYSA-N 8-[(methoxyamino)methyl]-5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC2=C(C(C)C)C(O)=C(C(C)C)C(CNOC)=C2OC21CCC2 PSQAEWRSNGCBBU-UHFFFAOYSA-N 0.000 claims 1
- XEZSGCHWPYPYDZ-UHFFFAOYSA-N 8-chloro-5-methylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C=C(Cl)C=2OC21CCC2 XEZSGCHWPYPYDZ-UHFFFAOYSA-N 0.000 claims 1
- RTWMEZKTECQOHV-UHFFFAOYSA-N 8-ethenyl-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C)=C(O)C(C)=C(C=C)C=2OC21CCC2 RTWMEZKTECQOHV-UHFFFAOYSA-N 0.000 claims 1
- VMMGXCHJKNEQEN-UHFFFAOYSA-N 8-methyl-5-propan-2-ylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC=2C(C(C)C)=C(O)C=C(C)C=2OC21CCC2 VMMGXCHJKNEQEN-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010002660 Anoxia Diseases 0.000 claims 1
- 241000976983 Anoxia Species 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010049565 Muscle fatigue Diseases 0.000 claims 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 1
- FZOKBKWRHFWRAA-UHFFFAOYSA-N OC=1C(=C2C(C3(COC2=C(C1C)C)CCC3)=O)C.CC3=C1CCC2(CCC2)SC1=C(C(=C3O)C)C Chemical compound OC=1C(=C2C(C3(COC2=C(C1C)C)CCC3)=O)C.CC3=C1CCC2(CCC2)SC1=C(C(=C3O)C)C FZOKBKWRHFWRAA-UHFFFAOYSA-N 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 235000014676 Phragmites communis Nutrition 0.000 claims 1
- 208000026301 Postoperative Cognitive Complications Diseases 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- WIWWDKWTJANWQD-UHFFFAOYSA-N [4-(methoxyamino)-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl] acetate Chemical compound O1C2=C(C)C(C)=C(OC(C)=O)C(C)=C2C(NOC)CC21CCC2 WIWWDKWTJANWQD-UHFFFAOYSA-N 0.000 claims 1
- GLVXKJAUGFYXKH-UHFFFAOYSA-N [5,7,8-trimethyl-3-(morpholin-4-ylmethyl)-4-oxospiro[3h-chromene-2,1'-cyclobutane]-6-yl] acetate Chemical compound C1COCCN1CC1C(=O)C2=C(C)C(OC(=O)C)=C(C)C(C)=C2OC21CCC2 GLVXKJAUGFYXKH-UHFFFAOYSA-N 0.000 claims 1
- CFBVRNGOZHWFNQ-UHFFFAOYSA-N [5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl] 2-amino-2-oxoacetate Chemical compound C1CC=2C(C(C)C)=C(OC(=O)C(N)=O)C(C(C)C)=CC=2OC21CCC2 CFBVRNGOZHWFNQ-UHFFFAOYSA-N 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 230000007953 anoxia Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 206010003230 arteritis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- QYNJCPQSEYEYCE-UHFFFAOYSA-N ethyl [4-(methoxyamino)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl] carbonate Chemical compound C1C(NOC)C2=C(C)C(OC(=O)OCC)=C(C)C=C2OC21CCC2 QYNJCPQSEYEYCE-UHFFFAOYSA-N 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 210000003097 mucus Anatomy 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- PUPSVQSUEINTDT-UHFFFAOYSA-N n-(6-hydroxy-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)acetamide Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(NC(=O)C)CC21CCC2 PUPSVQSUEINTDT-UHFFFAOYSA-N 0.000 claims 1
- CVGLXCFLMVWMGO-UHFFFAOYSA-N n-(6-hydroxy-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)butanamide Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(NC(=O)CCC)CC21CCC2 CVGLXCFLMVWMGO-UHFFFAOYSA-N 0.000 claims 1
- NKLOBTZXCVBQIH-UHFFFAOYSA-N n-(6-hydroxy-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)acetamide Chemical compound O1C2=CC(C)=C(O)C(C)=C2C(NC(=O)C)CC21CCC2 NKLOBTZXCVBQIH-UHFFFAOYSA-N 0.000 claims 1
- ZMQLNVNIRLLIFP-UHFFFAOYSA-N n-(6-hydroxy-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)benzenesulfonamide Chemical compound C1C(NS(=O)(=O)C=2C=CC=CC=2)C=2C(C)=C(O)C(C)=CC=2OC21CCC2 ZMQLNVNIRLLIFP-UHFFFAOYSA-N 0.000 claims 1
- YQOPAYCTBHKJIP-UHFFFAOYSA-N n-(6-hydroxy-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)methanesulfonamide Chemical compound C1C(NS(C)(=O)=O)C=2C(C)=C(O)C(C)=CC=2OC21CCC2 YQOPAYCTBHKJIP-UHFFFAOYSA-N 0.000 claims 1
- DALXCGJIJJUETQ-UHFFFAOYSA-N n-[(6-hydroxy-5,7,8-trimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)methyl]acetamide Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(CNC(=O)C)CC21CCC2 DALXCGJIJJUETQ-UHFFFAOYSA-N 0.000 claims 1
- SMWWFCWCLWXKJK-UHFFFAOYSA-N n-[(6-hydroxy-5,7,8-trimethylspiro[chromene-2,1'-cyclobutane]-4-yl)methyl]acetamide Chemical compound O1C2=C(C)C(C)=C(O)C(C)=C2C(CNC(=O)C)=CC21CCC2 SMWWFCWCLWXKJK-UHFFFAOYSA-N 0.000 claims 1
- PCELAKXFWFZRON-UHFFFAOYSA-N n-[[6-hydroxy-5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-8-yl]methyl]-n-methylacetamide Chemical compound O1C2=C(CN(C)C(C)=O)C(C(C)C)=C(O)C(C(C)C)=C2CCC21CCC2 PCELAKXFWFZRON-UHFFFAOYSA-N 0.000 claims 1
- YLTUSDKLQOSURV-UHFFFAOYSA-N n-[[6-hydroxy-5,7-di(propan-2-yl)spiro[3,4-dihydrochromene-2,1'-cyclobutane]-8-yl]methyl]acetamide Chemical compound O1C2=C(CNC(C)=O)C(C(C)C)=C(O)C(C(C)C)=C2CCC21CCC2 YLTUSDKLQOSURV-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 230000003959 neuroinflammation Effects 0.000 claims 1
- 210000003458 notochord Anatomy 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 230000011164 ossification Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 208000032253 retinal ischemia Diseases 0.000 claims 1
- QMOZGWKGOSWTFV-UHFFFAOYSA-N spiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-ol Chemical compound C1CC2=CC(O)=CC=C2OC21CCC2 QMOZGWKGOSWTFV-UHFFFAOYSA-N 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 2
- 0 *C(*)(*1)*c2c(*)c(*)c(*)c(*)c2C1=* Chemical compound *C(*)(*1)*c2c(*)c(*)c(*)c(*)c2C1=* 0.000 description 1
- GKMIEXPVHCDDBE-UHFFFAOYSA-N 2'-ethyl-4-methoxyimino-7,8-dimethylspiro[3H-chromene-2,1'-cyclobutane]-6-ol Chemical compound CCC1CCC12CC(=NOC)C3=CC(=C(C(=C3O2)C)C)O GKMIEXPVHCDDBE-UHFFFAOYSA-N 0.000 description 1
- LVWWKLABUULMNY-UHFFFAOYSA-N CCONC1CCC12CCC3=CC(=C(C(=C3O2)C)C)O Chemical compound CCONC1CCC12CCC3=CC(=C(C(=C3O2)C)C)O LVWWKLABUULMNY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- FUOIYQKYSTVVJM-UHFFFAOYSA-N [4-(methoxyamino)-5,7-dimethylspiro[3,4-dihydrochromene-2,1'-cyclobutane]-6-yl] 2-(dimethylamino)acetate Chemical compound O1C2=CC(C)=C(OC(=O)CN(C)C)C(C)=C2C(NOC)CC21CCC2 FUOIYQKYSTVVJM-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63558104P | 2004-12-13 | 2004-12-13 | |
| US65670905P | 2005-02-25 | 2005-02-25 | |
| US65671005P | 2005-02-25 | 2005-02-25 | |
| US67538605P | 2005-04-27 | 2005-04-27 | |
| US70258005P | 2005-07-26 | 2005-07-26 | |
| PCT/US2005/044768 WO2006065686A2 (en) | 2004-12-13 | 2005-12-09 | Spiro derivatives as lipoxygenase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008523145A JP2008523145A (ja) | 2008-07-03 |
| JP2008523145A5 true JP2008523145A5 (enExample) | 2009-02-05 |
Family
ID=36370831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007546793A Pending JP2008523145A (ja) | 2004-12-13 | 2005-12-09 | リポキシゲナーゼ阻害剤としてのスピロ誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7576094B2 (enExample) |
| EP (1) | EP1836183A2 (enExample) |
| JP (1) | JP2008523145A (enExample) |
| AU (1) | AU2005316739A1 (enExample) |
| BR (1) | BRPI0519013A2 (enExample) |
| CA (1) | CA2589363A1 (enExample) |
| MX (1) | MX2007007103A (enExample) |
| WO (1) | WO2006065686A2 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8338648B2 (en) * | 2004-06-12 | 2012-12-25 | Signum Biosciences, Inc. | Topical compositions and methods for epithelial-related conditions |
| CA2600004A1 (en) * | 2005-02-25 | 2006-09-08 | Eli Lilly And Company | Spiro-heterocyclic chromans, thiochromans and dihydroquinolines |
| AU2005328327A1 (en) * | 2005-02-25 | 2006-09-08 | Galileo Pharmaceuticals, Inc. | Novel lipoxygenase inhibitors |
| AU2007238071B2 (en) * | 2006-04-18 | 2012-06-07 | Abbvie Inc. | Antagonists of the vanilloid receptor subtype 1 (VR1) and uses thereof |
| US7939690B2 (en) * | 2006-11-15 | 2011-05-10 | High Point Pharmaceuticals, Llc | Haloalkylsulfone substituted compounds useful for treating obesity and diabetes |
| US20100249161A1 (en) * | 2006-11-15 | 2010-09-30 | Anders Klarskov Petersen | 2- ( 2 -hydroxyphenyl) -quinazolin-4-ones useful for treating obesity and diabetes |
| WO2008059026A1 (en) * | 2006-11-15 | 2008-05-22 | High Point Pharmaceuticals, Llc | Novel 2-(2-hydroxyphenyl)benzimidazoles useful for treating obesity and diabetes |
| CA2669874A1 (en) * | 2006-11-15 | 2008-05-22 | High Point Pharmaceuticals, Llc | Novel 2-(2-hydroxyphenyl) benzothiadiazines useful for treating obesity and diabetes |
| EA201000675A1 (ru) * | 2007-12-18 | 2011-06-30 | Гленмарк Фармасьютикалс, С.А. | Производные хромана как модуляторы trpv3 |
| GEP20125574B (en) | 2008-01-11 | 2012-07-10 | Glenmark Pharmaceuticals Sa | Fused pyrimidine derivatives as trpv3 modulators |
| CA2728405A1 (en) * | 2008-06-17 | 2010-01-14 | Glenmark Pharmaceuticals, S.A. | Chromane derivatives as trpv3 modulators |
| US8318928B2 (en) | 2008-12-15 | 2012-11-27 | Glenmark Pharmaceuticals, S.A. | Fused imidazole carboxamides as TRPV3 modulators |
| NZ595775A (en) | 2008-12-26 | 2013-07-26 | Glenmark Pharmaceuticals Sa | Fused imidazole derivatives as trpv3 antagonist |
| CA2924141C (en) | 2013-08-22 | 2022-06-07 | The General Hospital Corporation | 5-amino 4-cyano substituted oxazole and thiazole derivatives as inhibitors of human 12/15-lipoxygenase |
| EP3417851B1 (en) | 2013-09-09 | 2020-07-22 | Peloton Therapeutics, Inc. | Aryl ethers and uses thereof |
| CA2931085C (en) | 2013-12-16 | 2021-10-19 | Peloton Therapeutics, Inc. | Cyclic sulfone and sulfoximine analogs and uses thereof |
| JP2017502961A (ja) * | 2013-12-23 | 2017-01-26 | アレクトス セラピューティックス インコーポレイテッド | グルコセレブロシダーゼモジュレーターおよびその使用 |
| EP3268362B1 (en) | 2015-03-11 | 2021-10-20 | Peloton Therapeutics, Inc. | Substituted pyridines and uses thereof |
| US10512626B2 (en) | 2015-03-11 | 2019-12-24 | Peloton Therapeautics, Inc. | Compositions for use in treating glioblastoma |
| WO2016145032A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Compositions for use in treating pulmonary arterial hypertension |
| US10807948B2 (en) | 2015-03-11 | 2020-10-20 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
| US10335388B2 (en) | 2015-04-17 | 2019-07-02 | Peloton Therapeutics, Inc. | Combination therapy of a HIF-2-alpha inhibitor and an immunotherapeutic agent and uses thereof |
| US9796697B2 (en) | 2015-06-12 | 2017-10-24 | Peloton Therapeutics, Inc. | Tricyclic inhibitors of HIF-2-alpha and uses thereof |
| EP3377179B1 (en) | 2015-11-19 | 2021-04-07 | Concert Pharmaceuticals Inc. | Deuterated epi-743 |
| CA3173831A1 (en) * | 2020-03-19 | 2021-09-23 | Arcus Biosciences, Inc. | Tetralin and tetrahydroquinoline compounds as inhibitors of hif-2alpha |
| JP2025500506A (ja) * | 2021-12-23 | 2025-01-09 | ザ・カトリック・ユニヴェルシテイト・ルーバン | Ｙａｐ／ｔａｚ－ｔｅａｄを阻害するためのスピロ及び関連類似体 |
Family Cites Families (103)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3331846A (en) | 1963-08-28 | 1967-07-18 | Lilly Co Eli | Metal catalyst process for converting alpha-amino-acetylenes to dihydroquinoline |
| US3574627A (en) | 1969-02-06 | 1971-04-13 | Eastman Kodak Co | Color photographic elements |
| JPS5265267A (en) | 1975-11-26 | 1977-05-30 | Takeda Chem Ind Ltd | Synthesis of spiro compounds |
| JPS6030671B2 (ja) | 1976-12-13 | 1985-07-17 | 武田薬品工業株式会社 | スピロ化合物 |
| US4284644A (en) | 1977-01-12 | 1981-08-18 | Takeda Chemical Industries, Ltd. | Spirobenzofuranone compounds |
| US4342779A (en) | 1977-12-27 | 1982-08-03 | Takeda Chemical Industries, Ltd. | 7-Acetylspirobenzofuranone compound |
| HU179601B (en) | 1977-12-27 | 1982-11-29 | Takeda Chemical Industries Ltd | Process for producing spirobenzofuranone derivatives |
| JPS5646879A (en) | 1979-09-25 | 1981-04-28 | Takeda Chem Ind Ltd | Spiro compound, its preparation, and preventive and remedy for circulatory system disorder |
| US4330554A (en) | 1980-04-23 | 1982-05-18 | Takeda Chemical Industries, Ltd. | Spirobenzofuranone compounds |
| FI79535C (fi) | 1982-05-06 | 1990-01-10 | Erba Farmitalia | Foerfarande foer framstaellning av dihydrobensopyrans och dihydrobensotiopyrans substituerade iminoderivat. |
| EP0095316B1 (en) | 1982-05-21 | 1986-12-03 | Beecham Group Plc | Pharmaceutically active aminobenzopyrans |
| EP0126311B1 (en) | 1983-05-18 | 1989-09-13 | Beecham Group Plc | Benzopyran derivatives. |
| CA1261835A (en) | 1984-08-20 | 1989-09-26 | Masaaki Toda | (fused) benz(thio)amides |
| US4761403A (en) | 1986-04-09 | 1988-08-02 | Abbott Laboratories | Lipoxygenase inhibiting compounds |
| DE3777656D1 (de) | 1986-08-08 | 1992-04-23 | Upjohn Co | Mittel zur behandlung von alopezien. |
| GB8625185D0 (en) | 1986-10-21 | 1986-11-26 | Beecham Group Plc | Active compounds |
| GB8626344D0 (en) | 1986-11-04 | 1986-12-03 | Zyma Sa | Bicyclic compounds |
| US5387587A (en) | 1986-12-23 | 1995-02-07 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Chroman derivatives |
| DE3777366D1 (de) | 1986-12-27 | 1992-04-16 | Takeda Chemical Industries Ltd | 2,3-dihydro-cumaron-derivate, ihre herstellung und verwendung. |
| GB8701022D0 (en) | 1987-01-19 | 1987-02-18 | Beecham Group Plc | Treatment |
| GB8723157D0 (en) | 1987-10-02 | 1987-11-04 | Beecham Group Plc | Compounds |
| US5059609A (en) | 1987-10-19 | 1991-10-22 | Pfizer Inc. | Substituted tetralins, chromans and related compounds in the treatment of asthma, arthritis and related diseases |
| GB8800199D0 (en) | 1988-01-06 | 1988-02-10 | Beecham Group Plc | Pharmaceutical preparation |
| JPH07121936B2 (ja) | 1988-03-28 | 1995-12-25 | キッセイ薬品工業株式会社 | ジヒドロベンゾフラノン誘導体 |
| US5021432A (en) | 1988-04-26 | 1991-06-04 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzopyran compound and its pharmaceutical use |
| AU628331B2 (en) | 1988-05-06 | 1992-09-17 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Chroman derivatives |
| US4950684A (en) | 1988-05-20 | 1990-08-21 | G. D. Searle & Co. | 2,2-di-substituted benzopyran leukotriene-D4 antagonists |
| US5015661A (en) | 1988-08-09 | 1991-05-14 | Hoffmann-La Roche Inc. | Chromanes and their pharmaceutical compositions and methods |
| GB8902118D0 (en) | 1989-02-01 | 1989-03-22 | Beecham Group Plc | Chemical process |
| US5232938A (en) | 1989-05-24 | 1993-08-03 | Beecham Group P.L.C. | Certain 1,2,4-triazole(oxy or amino)benzopyran derivatives having pharmacological activity |
| DE3918041A1 (de) | 1989-06-02 | 1990-12-06 | Merck Patent Gmbh | Chromanderivate |
| GB8915315D0 (en) | 1989-07-04 | 1989-08-23 | Sandoz Ltd | Pharmaceutical compositions for use against hypertension and congestive heart failure |
| US5350747A (en) | 1989-07-07 | 1994-09-27 | Pfizer Inc | Heteroaryl piperazine antipsychotic agents |
| JPH0366669A (ja) | 1989-08-03 | 1991-03-22 | Shionogi & Co Ltd | 複素環式化合物 |
| GB8924373D0 (en) | 1989-10-30 | 1989-12-20 | Beecham Group Plc | Novel compounds |
| GB8928837D0 (en) | 1989-12-21 | 1990-02-28 | Beecham Group Plc | Pharmaceuticals |
| GB2242628A (en) | 1990-04-06 | 1991-10-09 | Sandoz Ltd | Asthma prophylactic use of K+ channel activators |
| JPH05506222A (ja) | 1990-04-23 | 1993-09-16 | ローヌ―プーラン ローラー インターナショナル （ホウルディングス）インコーポレイテッド | ５ｈｔ↓３拮抗物質としてのスピロ〔ベンゾフランシクロアルカン〕カルボキサミド |
| BE1004295A3 (fr) | 1990-05-17 | 1992-10-27 | Sandoz Sa | Utilisation des activateurs des canaux potassiques pour la prophylaxie de l'asthme. |
| US5076835A (en) | 1990-05-31 | 1991-12-31 | America Cyanamid Company | Aryloxyspiroalkylindolinone herbicides |
| DE4018552A1 (de) | 1990-06-09 | 1991-12-12 | Sandoz Ag | Asthma-prophylaktische verwendung von k(pfeil hoch)+(pfeil hoch) kanal-activatoren |
| ES2030627A6 (es) | 1990-11-28 | 1992-11-01 | Uriach & Cia Sa J | Procedimiento para la obtencion de compuestos benzopiranicos. |
| JP2612971B2 (ja) | 1991-02-19 | 1997-05-21 | 吉富製薬株式会社 | ベンゾピラン化合物 |
| DE4115521A1 (de) | 1991-05-11 | 1992-11-12 | Beiersdorf Ag | Isoindolyl- und isochinolylsubstituierte benzopyran-derivate, zwischenprodukte, sowie verfahren zu ihrer herstellung |
| GB9112721D0 (en) | 1991-06-13 | 1991-07-31 | Smithkline Beecham Plc | Novel treatment |
| US5624954A (en) | 1991-06-13 | 1997-04-29 | Smithkline Beecham P.L.C. | Benzo- and pyridopyran derivatives having anxiolytic and anti-convulsant activity |
| US5250547A (en) | 1991-08-29 | 1993-10-05 | Syntex (U.S.A.) Inc. | Benzopyran derivatives |
| CA2053962A1 (en) | 1991-10-22 | 1993-04-23 | Theo Schotten | Benzopyran derivatives, process for their preparation and use thereof and preparations containing the compounds |
| EP0543417A1 (en) | 1991-11-22 | 1993-05-26 | Lipogenics, Incorporated | Tocotrienols and tocotrienol-like compounds and methods for their use |
| US5686624A (en) | 1992-01-30 | 1997-11-11 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| US5849780A (en) | 1992-01-30 | 1998-12-15 | Sanofi | 1-benzenesulfonyl-1-1,3-dihydroindol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| FR2708605A1 (fr) | 1993-07-30 | 1995-02-10 | Sanofi Sa | Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| AU661159B2 (en) | 1992-07-15 | 1995-07-13 | Sumitomo Chemical Company, Limited | N-acyldihydroquinoline derivatives, a method for producing the same and their use as herbicides |
| FR2695387B1 (fr) | 1992-09-09 | 1994-10-21 | Adir | Nouveaux composés benzopyraniques, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| WO1994007867A1 (en) | 1992-09-28 | 1994-04-14 | Pfizer Inc. | Substituted pyrimidines for control of diabetic complications |
| US5939346A (en) | 1992-11-02 | 1999-08-17 | Akzo Nobel N.V. | Catalyst system comprising an aryloxyaluminoxane containing an electron withdrawing group |
| WO1994012173A1 (en) | 1992-11-30 | 1994-06-09 | Smithkline Beecham Plc | Benzopyron analogues for the treatment of anxiety, mania, depression or withdrawal symptoms |
| GB9225859D0 (en) | 1992-12-11 | 1993-02-03 | Smithkline Beecham Plc | Novel treatment |
| DE69327965T2 (de) | 1992-12-11 | 2000-10-19 | Smithkline Beecham Corp., Philadelphia | Pharmazeutische zusammenstellung enthaltende bizyklisch typ verbindungen |
| KR100326968B1 (ko) | 1992-12-11 | 2002-07-27 | 스미스클라인비이참피이엘시이 | 약학적 활성을 가진 이환식 화합물 |
| FR2708606B1 (fr) | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| JPH07188210A (ja) | 1993-11-19 | 1995-07-25 | Chugai Pharmaceut Co Ltd | ベンゾピラン−４−カルボン酸誘導体の製造法 |
| US5399562A (en) | 1994-02-04 | 1995-03-21 | G. D. Searle & Co. | Indolones useful as serotonergic agents |
| TW279878B (enExample) | 1994-03-18 | 1996-07-01 | Sumitomo Chemical Co | |
| JP3528242B2 (ja) | 1994-06-23 | 2004-05-17 | 住友化学工業株式会社 | ヒドロキシフラバン化合物の製造方法 |
| DE4428932A1 (de) | 1994-08-16 | 1996-02-22 | Hoechst Ag | Substituierte-Chinolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP0700959A1 (en) | 1994-09-07 | 1996-03-13 | Sumitomo Chemical Company, Limited | A rubber composition and a vulcanizing adhesion method using the same |
| CN1160399A (zh) | 1994-10-13 | 1997-09-24 | 美国辉瑞有限公司 | 苯并吡喃和苯并稠合化合物、其制备方法和它们作为白三烯b4(ltb4)拮抗剂的用途 |
| MX9702734A (es) | 1994-10-13 | 1997-06-28 | Pfizer | Benzopirano y compuestos benzocondensados, su preparacion y su uso como antagonistas de leucotrieno b4 (ltb4). |
| US5688808A (en) | 1994-12-22 | 1997-11-18 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
| US5925673A (en) | 1994-12-23 | 1999-07-20 | Alcon Laboratories, Inc. | Benzofurans and benzopyrans as cytoprotective agents |
| US5674876A (en) | 1995-01-20 | 1997-10-07 | Research Development Foundation | ρ-heteroatom-substituted phenols and uses thereof |
| FR2740136B1 (fr) | 1995-10-24 | 1998-01-09 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant |
| US5606006A (en) | 1996-04-08 | 1997-02-25 | Shell Oil Company | Trisepoxy resin compositions |
| AU4136897A (en) | 1996-09-09 | 1998-03-26 | Dainippon Pharmaceutical Co. Ltd. | 2,3-dihydrobenzofuran derivative and hepatopathy remedy comprising the same as active ingredient |
| FR2757157B1 (fr) | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US6005007A (en) | 1997-07-18 | 1999-12-21 | Farmer; Luc J. | Retinoids, methods for their production and use |
| HUP0100926A3 (en) | 1998-02-26 | 2003-03-28 | Neurogen Corp Branford | Benzylpiperazinyl- and benzylpiperidinyl ethanone derivatives, their preparation and their use as dopamine d4 receptor antagonists |
| FR2784988B1 (fr) | 1998-10-23 | 2002-09-20 | Adir | Nouveaux composes dihydro et tetrahydroquinoleiniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE19854147A1 (de) | 1998-11-24 | 2000-05-25 | Basf Ag | Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der Cocainsucht |
| FR2787451B1 (fr) | 1998-12-18 | 2001-01-26 | Adir | Nouveaux composes imidazoliniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2787789B1 (fr) | 1998-12-29 | 2002-06-14 | Lipha | Benzopyranes et benzoxepines utilisables dans le traitement de dyslipidemies, de l'atherosclerose et du diabete, compositions pharmaceutiques les contenant et procedes de preparations |
| DE10007948A1 (de) | 2000-02-22 | 2001-09-06 | Wella Ag | Mittel zur Färbung von Fasern |
| US20030212109A1 (en) | 2000-06-02 | 2003-11-13 | Mitchell Stephen Nicholas | Pharmaceutical compositions and their use |
| WO2002010135A1 (en) | 2000-08-01 | 2002-02-07 | Ono Pharmaceutical Co., Ltd. | 3,4-dihydroisoquinoline derivative compounds and drugs containing these compounds as the active ingredient |
| CA2420869A1 (en) | 2000-08-29 | 2002-03-07 | Allergan, Inc. | Compounds having activity as inhibitors of cytochrome p450rai |
| US6369225B1 (en) | 2000-08-29 | 2002-04-09 | Allergan Sales, Inc. | Compounds having activity as inhibitors of cytochrome P450RAI |
| US6252090B1 (en) | 2000-08-29 | 2001-06-26 | Allergan Sales, Inc. | Compounds having activity as inhibitors of cytochrome P450RAI |
| US6291677B1 (en) | 2000-08-29 | 2001-09-18 | Allergan Sales, Inc. | Compounds having activity as inhibitors of cytochrome P450RAI |
| US6313107B1 (en) | 2000-08-29 | 2001-11-06 | Allergan Sales, Inc. | Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI |
| GB0028697D0 (en) | 2000-11-23 | 2001-01-10 | S P A | Novel process |
| JP2005514366A (ja) | 2001-11-20 | 2005-05-19 | イーライ・リリー・アンド・カンパニー | ３−置換オキシインドールβ３アゴニスト |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| US7205328B2 (en) | 2002-10-21 | 2007-04-17 | Irm Llc | Oxindoles with anti-HIV activity |
| DE10335450A1 (de) | 2003-08-02 | 2005-02-17 | Bayer Ag | Indolin-Sulfanilsäureamide |
| DE10335449A1 (de) | 2003-08-02 | 2005-02-17 | Bayer Healthcare Ag | Bicyclische Indolinsulfonamid-Derivate |
| WO2005033092A1 (en) | 2003-09-19 | 2005-04-14 | Galileo Pharmaceuticals, Inc. | Chroman derivatives |
| AU2004309419A1 (en) | 2003-12-23 | 2005-07-14 | Arena Pharmaceuticals, Inc. | Novel spiroindoline or spiroisoquinoline compounds, methods of use and compositions thereof |
| AU2005205016B2 (en) | 2004-01-16 | 2010-07-15 | F. Hoffmann-La Roche Ag | 1-benzyl-5-piperazin-1-yl-3,4 dihydro-1H-quinazolin-2-one derivatives and the respective 1H-benzo(1,2,6)thiadiazine-2,2-dioxide and 1,4-dihydro-benzo(D) (1,3)oxazin-2-one derivatives as modulators of the 5-hydroxytryptamine receptor (5-HT) for the treatment of diseases of the central nervous system |
| EP1589015A1 (en) | 2004-02-03 | 2005-10-26 | Université de Liège | Benzopyran derivatives, method of production and use thereof |
| WO2006044556A2 (en) | 2004-10-14 | 2006-04-27 | Galileo Pharmaceuticals, Inc. | Dual inhibitors of lipoxygenase for treating diabetes |
| AU2005328327A1 (en) | 2005-02-25 | 2006-09-08 | Galileo Pharmaceuticals, Inc. | Novel lipoxygenase inhibitors |
| CA2600004A1 (en) | 2005-02-25 | 2006-09-08 | Eli Lilly And Company | Spiro-heterocyclic chromans, thiochromans and dihydroquinolines |
-
2005
- 2005-12-09 CA CA002589363A patent/CA2589363A1/en not_active Abandoned
- 2005-12-09 BR BRPI0519013-4A patent/BRPI0519013A2/pt not_active IP Right Cessation
- 2005-12-09 AU AU2005316739A patent/AU2005316739A1/en not_active Abandoned
- 2005-12-09 WO PCT/US2005/044768 patent/WO2006065686A2/en not_active Ceased
- 2005-12-09 MX MX2007007103A patent/MX2007007103A/es not_active Application Discontinuation
- 2005-12-09 JP JP2007546793A patent/JP2008523145A/ja active Pending
- 2005-12-09 US US11/298,137 patent/US7576094B2/en not_active Expired - Fee Related
- 2005-12-09 EP EP05853636A patent/EP1836183A2/en not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8691822B2 (en) | Dihydropteridinone derivatives, preparation process and pharmaceutical use thereof | |
| JP5733982B2 (ja) | サイトカインの産生を抑制する化合物及びその調製方法 | |
| CN101553493B (zh) | 三环螺哌啶化合物、它们的合成和它们作为趋化因子受体活性调节剂的用途 | |
| JP2011511003A5 (enExample) | ||
| ES2890986T3 (es) | Antagonistas de TRPV4 | |
| ES2700156T3 (es) | Derivados de flavaglinas | |
| CN108024971A (zh) | 作为irak-4抑制剂的取代的氮杂化合物 | |
| AU2013234009A1 (en) | Heterocyclyl compounds as MEK inhibitors | |
| ES2569511T3 (es) | Inhibidores del transportador equilibrativo de nucleósidos ENT1 | |
| CN118475575A (zh) | 一种肽基腈类化合物及其应用 | |
| EA031477B1 (ru) | Производные 1-(циклопент-2-ен-1-ил)-3-(2-гидрокси-3-(арилсульфонил)фенил)мочевины в качестве ингибиторов cxcr2 | |
| CA3093706A1 (en) | Jak inhibitors | |
| AU2024340552A1 (en) | Dipeptidyl peptidase 1 inhibitors and uses thereof | |
| EA001625B1 (ru) | Производные 3-алкоксиизоксазол-4-илзамещенных 2-аминокарбоновых кислот | |
| WO2011067348A2 (en) | Mek inhibitor salts and solvates thereof | |
| US20120184546A1 (en) | [1,2,4]triazolo [1,5-c]pyrimidine derivatives as hsp90 modulators | |
| ES2731429T3 (es) | Compuestos de indanilurea inhibidores de MAP quinasa P38 | |
| US6858605B2 (en) | Substituted 2,3-benzodiazepine derivatives | |
| TWI732748B (zh) | 噻唑衍生物的製造方法 | |
| US8871788B2 (en) | Substituted N-alkyl and N-acyl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof | |
| CN117015548A (zh) | 合成的熊果酸衍生物和其使用方法 | |
| US20070196270A1 (en) | Compounds As Ccri Antagonists | |
| TWI522356B (zh) | 二氫喋啶酮類衍生物、其製備方法及其在醫藥上的應用 | |
| TW202542136A (zh) | １，３－苯并二氧雜環戊烯衍生物以及其用途 | |
| JP2025512951A (ja) | Ｇｐｒ３５調節因子及びその使用 |