JP2008523145A5 - - Google Patents
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- 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
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- 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
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- 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
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- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
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| PCT/US2005/044768 WO2006065686A2 (en) | 2004-12-13 | 2005-12-09 | Spiro derivatives as lipoxygenase inhibitors |
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| EP2086951B1 (en) * | 2006-11-15 | 2011-12-21 | High Point Pharmaceuticals, LLC | Novel 2-(2-hydroxyphenyl) benzothiadiazines useful for treating obesity and diabetes |
| EP2097391A1 (en) * | 2006-11-15 | 2009-09-09 | High Point Pharmaceuticals, LLC | 2- ( 2 -hydroxyphenyl) -quinazolin-4-ones useful for treating obesity and diabetes |
| US7939690B2 (en) * | 2006-11-15 | 2011-05-10 | High Point Pharmaceuticals, Llc | Haloalkylsulfone substituted compounds useful for treating obesity and diabetes |
| ATE523497T1 (de) * | 2006-11-15 | 2011-09-15 | High Point Pharmaceuticals Llc | Neue 2-(2-hydroxyphenyl)benzimidazole, die sich für die behandlung von obesitas und diabetes eignen |
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| PL3417851T3 (pl) | 2013-09-09 | 2020-12-14 | Peloton Therapeutics, Inc. | Etery arylowe i ich zastosowanie |
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| US9796680B2 (en) * | 2013-12-23 | 2017-10-24 | Alectos Therapeutics Inc. | Glucocerebrosidase modulators and uses thereof |
| WO2016144825A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
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| CN119118872A (zh) * | 2020-03-19 | 2024-12-13 | 艾库斯生物科学有限公司 | 作为HIF-2α抑制剂的四氢化萘和四氢喹啉化合物 |
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2005
- 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 BR BRPI0519013-4A patent/BRPI0519013A2/pt not_active IP Right Cessation
- 2005-12-09 CA CA002589363A patent/CA2589363A1/en not_active Abandoned
- 2005-12-09 EP EP05853636A patent/EP1836183A2/en not_active Withdrawn
- 2005-12-09 US US11/298,137 patent/US7576094B2/en not_active Expired - Fee Related
- 2005-12-09 JP JP2007546793A patent/JP2008523145A/ja active Pending
- 2005-12-09 MX MX2007007103A patent/MX2007007103A/es not_active Application Discontinuation
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