BG61946B1 - Хетеробициклични съединения - Google Patents
Хетеробициклични съединения Download PDFInfo
- Publication number
- BG61946B1 BG61946B1 BG98990A BG9899094A BG61946B1 BG 61946 B1 BG61946 B1 BG 61946B1 BG 98990 A BG98990 A BG 98990A BG 9899094 A BG9899094 A BG 9899094A BG 61946 B1 BG61946 B1 BG 61946B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- benzopyran
- oxo
- phenyl
- methoxyphenyl
- piperazinyl
- Prior art date
Links
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 478
- 239000002904 solvent Substances 0.000 claims abstract description 143
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 337
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 307
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 193
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 142
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 120
- 238000000034 method Methods 0.000 claims description 91
- -1 hydroxymethylene group Chemical group 0.000 claims description 87
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 82
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 51
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 239000002798 polar solvent Substances 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical compound O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000651 prodrug Substances 0.000 claims description 10
- 229940002612 prodrug Drugs 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- OJXOWGJHAMWLIZ-UHFFFAOYSA-N 2-phenyl-4h-chromene Chemical compound O1C2=CC=CC=C2CC=C1C1=CC=CC=C1 OJXOWGJHAMWLIZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005277 alkyl imino group Chemical group 0.000 claims description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- JUXHWXSCFVJNBO-UHFFFAOYSA-N 3-methyl-4-oxo-n-[3-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-2-phenylchromene-8-carboxamide Chemical compound O1C2=C(C(=O)NCCCN3CCC(CC3)N3C(NC4=CC=CC=C43)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 JUXHWXSCFVJNBO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- NUFZAKVXJKBCKH-UHFFFAOYSA-N n-[3-[4-(2-hydroxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1O NUFZAKVXJKBCKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- AIHBTWJKGJLMQK-UHFFFAOYSA-N 1-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-(3-methyl-4-oxo-2-phenylchromen-8-yl)urea Chemical compound COC1=CC=CC=C1N1CCN(CCNC(=O)NC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 AIHBTWJKGJLMQK-UHFFFAOYSA-N 0.000 claims 1
- VKFKZXYBWCJYEL-UHFFFAOYSA-N 2-(4-acetamidophenyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4h-chromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C=3OC(=C(C)CC=3C=CC=2)C=2C=CC(NC(C)=O)=CC=2)CC1 VKFKZXYBWCJYEL-UHFFFAOYSA-N 0.000 claims 1
- ZSRGFRKPAWJRFS-UHFFFAOYSA-N 2-(4-benzoylphenyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(=CC=3)C(=O)C=3C=CC=CC=3)=O)C=CC=2)CC1 ZSRGFRKPAWJRFS-UHFFFAOYSA-N 0.000 claims 1
- OTTBKKADQUBYBE-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4h-chromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C=3OC(=C(C)CC=3C=CC=2)C=2C=CC(O)=CC=2)CC1 OTTBKKADQUBYBE-UHFFFAOYSA-N 0.000 claims 1
- JUVOUCMSCDSJKT-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxochromene-8-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C)C(=O)C2=CC=CC(C(=O)NCCCN3CCN(CC3)C=3C(=CC=CC=3)OC)=C2O1 JUVOUCMSCDSJKT-UHFFFAOYSA-N 0.000 claims 1
- OACYQPAAMXSVNB-UHFFFAOYSA-N 2-(furan-2-yl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(C=4OC=CC=4)O3)=O)C=CC=2)CC1 OACYQPAAMXSVNB-UHFFFAOYSA-N 0.000 claims 1
- ZBPSIFSAIORGCU-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)piperazin-1-yl]-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)ethanesulfonamide Chemical compound COC1=CC=CC=C1N1CCN(CCS(=O)(=O)NC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 ZBPSIFSAIORGCU-UHFFFAOYSA-N 0.000 claims 1
- ZNQIGQYRWNLSOL-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl 2-(3-methyl-4-oxo-2-phenylchromen-8-yl)acetate Chemical compound COC1=CC=CC=C1N1CCN(CCOC(=O)CC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 ZNQIGQYRWNLSOL-UHFFFAOYSA-N 0.000 claims 1
- WDCJTOYZECAXFV-UHFFFAOYSA-N 2-benzoyl-3-ethyl-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-1-benzofuran-7-carboxamide Chemical compound C1=CC=C2C(CC)=C(C(=O)C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC WDCJTOYZECAXFV-UHFFFAOYSA-N 0.000 claims 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 claims 1
- AMXUSCINCMSBME-UHFFFAOYSA-N 2-tert-butyl-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C(C)(C)C)=O)C=CC=2)CC1 AMXUSCINCMSBME-UHFFFAOYSA-N 0.000 claims 1
- NCIOCKHTDZICDA-UHFFFAOYSA-N 3-(hydroxymethyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(CO)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 NCIOCKHTDZICDA-UHFFFAOYSA-N 0.000 claims 1
- YBBPHQCZDDELQR-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)propanamide Chemical compound COC1=CC=CC=C1N1CCN(CCC(=O)NC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 YBBPHQCZDDELQR-UHFFFAOYSA-N 0.000 claims 1
- PITPWFZWDVXSRM-UHFFFAOYSA-N 3-methyl-4-oxo-2-phenyl-n-[3-(4-phenylpiperidin-1-yl)propyl]chromene-8-carboxamide Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCC1C1=CC=CC=C1 PITPWFZWDVXSRM-UHFFFAOYSA-N 0.000 claims 1
- SOSSYEZSNHOGLE-UHFFFAOYSA-N 3-methyl-n-[3-[methyl-(1-oxo-3,4-dihydro-2h-naphthalen-2-yl)amino]propyl]-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C1CC2=CC=CC=C2C(=O)C1N(C)CCCNC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 SOSSYEZSNHOGLE-UHFFFAOYSA-N 0.000 claims 1
- VTTFQDRNGLRVKA-UHFFFAOYSA-N 6-(dimethylamino)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(C=2)N(C)C)CC1 VTTFQDRNGLRVKA-UHFFFAOYSA-N 0.000 claims 1
- LVCAOLJGEFYZDO-UHFFFAOYSA-N 6-(ethylamino)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C=12OC(C=3C=CC=CC=3)=C(C)C(=O)C2=CC(NCC)=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC LVCAOLJGEFYZDO-UHFFFAOYSA-N 0.000 claims 1
- QDNHGZLDPJIVMR-UHFFFAOYSA-N 6-(methanesulfonamido)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(NS(C)(=O)=O)C=2)CC1 QDNHGZLDPJIVMR-UHFFFAOYSA-N 0.000 claims 1
- UXXIKASLHUNDRI-UHFFFAOYSA-N 6-acetamido-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(NC(C)=O)C=2)CC1 UXXIKASLHUNDRI-UHFFFAOYSA-N 0.000 claims 1
- SYEJJGSUNDDJNN-UHFFFAOYSA-N 6-amino-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(N)C=2)CC1 SYEJJGSUNDDJNN-UHFFFAOYSA-N 0.000 claims 1
- IJNREAGEYUEUGU-UHFFFAOYSA-N 6-bromo-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(Br)C=2)CC1 IJNREAGEYUEUGU-UHFFFAOYSA-N 0.000 claims 1
- MFARXKMBBGGEBW-UHFFFAOYSA-N 6-hydroxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(O)C=2)CC1 MFARXKMBBGGEBW-UHFFFAOYSA-N 0.000 claims 1
- STXXGVGIPQLGJW-UHFFFAOYSA-N 6-methoxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C=12OC(C=3C=CC=CC=3)=C(C)C(=O)C2=CC(OC)=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC STXXGVGIPQLGJW-UHFFFAOYSA-N 0.000 claims 1
- FZCYCHSLXKNZEO-UHFFFAOYSA-N 7-methoxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2OC)CC1 FZCYCHSLXKNZEO-UHFFFAOYSA-N 0.000 claims 1
- BUXSCFIFZNLZAN-NJZRLIGZSA-N 8-[(e)-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxyiminomethyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCO\N=C\C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 BUXSCFIFZNLZAN-NJZRLIGZSA-N 0.000 claims 1
- XIRPNHGMMUAPCN-MDWZMJQESA-N 8-[(e)-4-[4-(2-methoxyphenyl)piperazin-1-yl]but-1-enyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CC\C=C\C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 XIRPNHGMMUAPCN-MDWZMJQESA-N 0.000 claims 1
- AXJMQOHFDZHXPM-UHFFFAOYSA-N 8-[1-ethoxy-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one Chemical compound C=1C=CC(C(C(C)=C(C=2C=CC=CC=2)O2)=O)=C2C=1C(OCC)CN(CC1)CCN1C1=CC=CC=C1OC AXJMQOHFDZHXPM-UHFFFAOYSA-N 0.000 claims 1
- JOKODPSBEBBYKU-UHFFFAOYSA-N 8-[2-[2-(2,6-dimethoxyphenoxy)ethylamino]ethoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC(OC)=C1OCCNCCOC1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O JOKODPSBEBBYKU-UHFFFAOYSA-N 0.000 claims 1
- JDKAFVCWJVJXBQ-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCOC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 JDKAFVCWJVJXBQ-UHFFFAOYSA-N 0.000 claims 1
- XSIMYVIHHSVTML-UHFFFAOYSA-N 8-[2-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CC(O)COC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 XSIMYVIHHSVTML-UHFFFAOYSA-N 0.000 claims 1
- CVIYJJLZWPEVRU-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propanoyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 CVIYJJLZWPEVRU-UHFFFAOYSA-N 0.000 claims 1
- GEHDMIHNCABTQT-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylsulfanyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCSC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 GEHDMIHNCABTQT-UHFFFAOYSA-N 0.000 claims 1
- LNGUSSHELAJOGC-UHFFFAOYSA-N 8-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 LNGUSSHELAJOGC-UHFFFAOYSA-N 0.000 claims 1
- YRWPUULVIZIZKK-UHFFFAOYSA-N 8-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCCC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 YRWPUULVIZIZKK-UHFFFAOYSA-N 0.000 claims 1
- QCGUXTXLFNMPQT-UHFFFAOYSA-N 8-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butylsulfinyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCCS(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 QCGUXTXLFNMPQT-UHFFFAOYSA-N 0.000 claims 1
- BNZGJYFMZJHEKO-UHFFFAOYSA-N 8-[5-[4-(2-methoxyphenyl)piperazin-1-yl]pentoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCCCOC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 BNZGJYFMZJHEKO-UHFFFAOYSA-N 0.000 claims 1
- 101100257999 Danio rerio stambpa gene Proteins 0.000 claims 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 claims 1
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- 238000000926 separation method Methods 0.000 description 1
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- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
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- GNCGTEQGBYYYBX-UHFFFAOYSA-M sodium;4-methylbenzoate Chemical compound [Na+].CC1=CC=C(C([O-])=O)C=C1 GNCGTEQGBYYYBX-UHFFFAOYSA-M 0.000 description 1
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- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
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- 238000003419 tautomerization reaction Methods 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- SCHZCUMIENIQMY-UHFFFAOYSA-N tris(trimethylsilyl)silicon Chemical compound C[Si](C)(C)[Si]([Si](C)(C)C)[Si](C)(C)C SCHZCUMIENIQMY-UHFFFAOYSA-N 0.000 description 1
- FUCBQMFTYFQCOB-UHFFFAOYSA-N trityl perchlorate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCl(=O)(=O)=O)C1=CC=CC=C1 FUCBQMFTYFQCOB-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI920408A IT1254469B (it) | 1992-02-25 | 1992-02-25 | Derivati benzopiranici e benzotiopiranici |
US07/888,775 US5403842A (en) | 1992-02-25 | 1992-05-26 | Benzopyran and benzothiopyran derivatives |
PCT/EP1993/000420 WO1993017007A1 (en) | 1992-02-25 | 1993-02-23 | Heterobicyclic compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
BG98990A BG98990A (bg) | 1995-05-31 |
BG61946B1 true BG61946B1 (bg) | 1998-10-30 |
Family
ID=26330842
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG98990A BG61946B1 (bg) | 1992-02-25 | 1994-08-19 | Хетеробициклични съединения |
Country Status (25)
Country | Link |
---|---|
EP (1) | EP0558245A1 (fi) |
JP (1) | JPH069606A (fi) |
AU (2) | AU3629693A (fi) |
BG (1) | BG61946B1 (fi) |
CA (1) | CA2090156A1 (fi) |
CZ (1) | CZ205994A3 (fi) |
DZ (1) | DZ1666A1 (fi) |
EE (1) | EE03177B1 (fi) |
EG (1) | EG20333A (fi) |
FI (1) | FI943876A0 (fi) |
HR (1) | HRP930210A2 (fi) |
HU (1) | HUT72448A (fi) |
IL (1) | IL104824A (fi) |
LT (1) | LT3038B (fi) |
LV (1) | LV10099B (fi) |
MX (1) | MX9300977A (fi) |
NO (1) | NO943140L (fi) |
NZ (1) | NZ245995A (fi) |
PL (1) | PL175556B1 (fi) |
SG (1) | SG65570A1 (fi) |
SI (1) | SI9300094A (fi) |
SK (1) | SK280143B6 (fi) |
TW (1) | TW382628B (fi) |
WO (1) | WO1993017007A1 (fi) |
ZA (1) | ZA931278B (fi) |
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MX9300312A (es) * | 1992-01-23 | 1993-07-31 | Pfizer | Antagonistas benzopiranicos y relacionado de ltb. |
FR2689127B1 (fr) * | 1992-03-31 | 1994-05-06 | Adir Cie | Nouvelles 3', 5' -ditertbutyl-4'-hydroxy flavones, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
IT1266582B1 (it) * | 1993-07-30 | 1997-01-09 | Recordati Chem Pharm | Derivati (di)azacicloesanici e diazacicloeptanici |
GB9317071D0 (en) * | 1993-08-17 | 1993-09-29 | Univ Strathclyde | Flavonoids |
JP3426242B2 (ja) * | 1994-01-14 | 2003-07-14 | 株式会社アズウェル | ジアザシクロアルカンアルキルスルホンアミド誘導体 |
FR2717175B1 (fr) * | 1994-03-11 | 1996-06-14 | Adir | Nouveaux composés alkylaminoindanes, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent. |
IL112764A0 (en) * | 1994-03-18 | 1995-05-26 | Ferrer Int | New chromene derivatives |
ES2101620B1 (es) * | 1994-03-18 | 1998-04-01 | Ferrer Int | Nuevo compuesto derivado del cromeno. |
PT753511E (pt) * | 1994-03-30 | 2001-11-30 | Zeria Pharm Co Ltd | Derivados de acido 4-indol-1-butirico, sua preparacao e utilizacao como inibidores dos receptores alfa-1-adrenergicos e das 5-alfa-redutases da testosterona |
US5503843A (en) * | 1994-04-22 | 1996-04-02 | Flora Inc. | Transdermal delivery of alpha adrenoceptor blocking agents |
DE4425146A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
GB9417135D0 (en) * | 1994-08-23 | 1994-10-12 | Medinnova S F | Method |
CA2188924C (en) * | 1995-02-28 | 2008-04-08 | Hirokazu Annoura | Arylpiperidine and arylpiperazine derivatives and drugs containing the same |
GB9507288D0 (en) * | 1995-04-07 | 1995-05-31 | Sod Conseils Rech Applic | Phenoxyethylamine derivatives with high affinity for 5-HT1A receptors |
US5859014A (en) * | 1995-06-09 | 1999-01-12 | Syntex (U.S.A.) Inc. | Pyrimidinedione, pyrimidinetrione, triazinedione and tetrahydroquinazolinedione derivatives as α1 -adrenergic receptor antagonists |
ATE201016T1 (de) * | 1995-06-09 | 2001-05-15 | Hoffmann La Roche | Pyrimidindion-, pyrimidintrion-, triazindion- derivate als alpha-1-adrenergische rezeptorantagonisten |
JPH0967367A (ja) * | 1995-06-23 | 1997-03-11 | Suntory Ltd | チオピラン誘導体 |
WO1997014419A1 (en) * | 1995-10-20 | 1997-04-24 | Flora Inc. | Transdermal delivery of alpha adrenoceptor blocking agents |
US5990114A (en) * | 1996-02-28 | 1999-11-23 | Recordati, S.A., Chemical And Pharmaceutical Company | Use of 5-HT1A receptor antagonists for the treatment of urinary incontinence |
IT1282705B1 (it) * | 1996-02-28 | 1998-03-31 | Recordati Chem Pharm | Uso di antagonisti del recettore serotoninergico 5-ht|a per il trattamento dell'incontinenza urinaria |
AU2030197A (en) * | 1996-03-08 | 1997-09-22 | Synthelabo | 2-aminoethyl-benzofuran derivatives, preparation thereof and therapeutical use thereof |
FR2745815B1 (fr) * | 1996-03-08 | 1998-06-26 | Synthelabo | Derives de benzofurane, leur preparations et compositions pharmaceutiques les comprenant |
EP0929537A1 (en) * | 1996-08-22 | 1999-07-21 | Hoechst Marion Roussel, Inc. | Troponyl piperazines as selective dopamine d4 receptor ligands |
AU2002300904B2 (en) * | 1997-05-12 | 2004-12-23 | Ortho-Mcneil Pharmaceutical, Inc. | Arylsubstituted piperazines useful in the treatment of benign prostatic hyperplasia |
EA001904B1 (ru) | 1997-05-12 | 2001-10-22 | ОРТО МакНЕЙЛ ФАРМАСЬЮТИКАЛ, ИНК. | Арилзамещенные пиперазины для лечения доброкачественной гиперплазии простаты |
DE69818079T2 (de) | 1997-06-04 | 2004-06-03 | Azwell Inc. | Verfahren zur herstellung von piperazinsulfonamid-derivaten und ihren salzen |
AU8130298A (en) * | 1997-07-15 | 1999-02-10 | Sankyo Company Limited | Piperazine derivatives |
IT1313581B1 (it) * | 1999-07-30 | 2002-09-09 | Recordati Chem Pharm | Derivati tienopirancarbossamidici. |
US6387909B1 (en) | 1999-07-30 | 2002-05-14 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyranecarboxamide derivatives |
US6306861B1 (en) | 1999-07-30 | 2001-10-23 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyrancecarboxamide derivatives |
DE19941657A1 (de) * | 1999-09-01 | 2001-03-08 | Schwabe Willmar Gmbh & Co | Zimtsäurenitrile, Verfahren zu ihrer Herstellung und Verwendung |
US6403594B1 (en) | 1999-10-18 | 2002-06-11 | Recordati, S.A. Chemical And Pharmaceutical Company | Benzopyran derivatives |
IT1314192B1 (it) * | 1999-10-18 | 2002-12-06 | Recordati Chem Pharm | Derivati benzopiranici |
JP2002113006A (ja) | 2000-10-10 | 2002-04-16 | Toshiba Medical System Co Ltd | 診断機器設定方法および診断装置 |
CN1150176C (zh) * | 2002-05-22 | 2004-05-19 | 上海医药工业研究院 | 芳烷酮哌嗪衍生物及其应用 |
JP2006511500A (ja) * | 2002-10-30 | 2006-04-06 | メルク エンド カムパニー インコーポレーテッド | γ−アミノアミド系のケモカイン受容体活性調節剤 |
AU2005275181A1 (en) | 2004-07-14 | 2006-02-23 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7645881B2 (en) | 2004-07-22 | 2010-01-12 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
CA2597616A1 (en) | 2005-02-17 | 2006-08-24 | Wyeth | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
CA2738809C (en) * | 2008-09-29 | 2015-11-24 | Sirtris Pharmaceuticals, Inc. | Quinazolinone, quinolone and related analogs as sirtuin modulators |
CZ304045B6 (cs) | 2012-04-10 | 2013-09-04 | Univerzita Palackého | Pouzití komplexu medi obsahujících 2-fenyl-3-hydroxychinolin-4(1H)-on a deriváty 1,10-fenanthrolinu pro prípravu léciv pro lécbu nádorových onemocnení |
JP2019508400A (ja) | 2016-02-09 | 2019-03-28 | ファーマケア,インク. | キノリノンリシルオキシダーゼ様2阻害剤とその使用 |
WO2020095912A1 (ja) * | 2018-11-06 | 2020-05-14 | 第一三共株式会社 | ベンズイミダゾール誘導体 |
EP4058425A4 (en) | 2019-11-11 | 2023-11-22 | Southwest Research Institute | RECRYSTALLIZED HI-6 DIMETHYL SULFATE |
AR120680A1 (es) | 2019-12-06 | 2022-03-09 | Vertex Pharma | Tetrahidrofuranos sustituidos como moduladores de canales de sodio |
AR126073A1 (es) | 2021-06-04 | 2023-09-06 | Vertex Pharma | N-(hidroxialquil(hetero)aril)tetrahidrofuran carboxamidas como moduladores de canales de sodio |
EP4426434A1 (en) | 2021-11-02 | 2024-09-11 | Flare Therapeutics, Inc. | Pparg inverse agonists and uses thereof |
CN115160279B (zh) * | 2022-07-27 | 2023-11-24 | 中国药科大学 | 苯并吡喃酮类化合物、药物组合物和应用 |
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US2921070A (en) * | 1957-11-05 | 1960-01-12 | Recordati Lab Farmacologico S | Basic esters of 3-methylflavone-8-carboxylic acid |
GB1156973A (en) | 1965-07-06 | 1969-07-02 | Quinazoline Derivatives | |
DE2123923A1 (de) * | 1971-05-14 | 1972-11-23 | Boehringer Mannheim Gmbh, 6800 Mannheim | 4-eckige Klammer auf omega- (Flavon-7yl-oxy) -alkyl eckige Klammer zu -pigerazin-Derivate und Verfahren zu ihrer Herstellung |
NZ200981A (en) | 1981-07-17 | 1984-10-19 | Recordati Chem Pharm | 3-methylflavone-8-carboxylic acid derivatives and pharmaceutical compositions |
JPS60202872A (ja) * | 1984-03-27 | 1985-10-14 | Kaken Pharmaceut Co Ltd | ベンゾフラン誘導体、その製法およびそれを有効成分とする降圧剤 |
US4678787A (en) * | 1985-01-30 | 1987-07-07 | Warner-Lambert Company | 4H-1-benzopyran-4-ones and their sulfur containing analogs |
JPS63139180A (ja) * | 1986-12-02 | 1988-06-10 | Tanabe Seiyaku Co Ltd | カルボン酸誘導体 |
IL87451A0 (en) * | 1987-09-04 | 1989-01-31 | Tanabe Seiyaku Co | Benzofuran derivatives,their preparation and pharmaceutical compositions containing them |
US5278174A (en) * | 1990-06-04 | 1994-01-11 | Scios Nova, Inc. | Sigma binding site agents |
-
1993
- 1993-02-22 SG SG1996004802A patent/SG65570A1/en unknown
- 1993-02-22 EP EP93301264A patent/EP0558245A1/en not_active Withdrawn
- 1993-02-22 HR HR930210A patent/HRP930210A2/hr not_active Application Discontinuation
- 1993-02-23 CZ CZ942059A patent/CZ205994A3/cs unknown
- 1993-02-23 SK SK1007-94A patent/SK280143B6/sk unknown
- 1993-02-23 HU HU9402443A patent/HUT72448A/hu unknown
- 1993-02-23 AU AU36296/93A patent/AU3629693A/en not_active Abandoned
- 1993-02-23 IL IL10482493A patent/IL104824A/en not_active IP Right Cessation
- 1993-02-23 PL PL93304889A patent/PL175556B1/pl unknown
- 1993-02-23 MX MX9300977A patent/MX9300977A/es not_active IP Right Cessation
- 1993-02-23 WO PCT/EP1993/000420 patent/WO1993017007A1/en not_active Application Discontinuation
- 1993-02-23 CA CA002090156A patent/CA2090156A1/en not_active Abandoned
- 1993-02-24 ZA ZA931278A patent/ZA931278B/xx unknown
- 1993-02-24 DZ DZ930019A patent/DZ1666A1/fr active
- 1993-02-24 LV LVP-93-136A patent/LV10099B/en unknown
- 1993-02-24 AU AU33773/93A patent/AU660067B2/en not_active Ceased
- 1993-02-24 LT LTIP354A patent/LT3038B/lt not_active IP Right Cessation
- 1993-02-25 SI SI19939300094A patent/SI9300094A/sl unknown
- 1993-02-25 EG EG1193A patent/EG20333A/xx active
- 1993-02-25 NZ NZ245995A patent/NZ245995A/en unknown
- 1993-02-25 JP JP5036605A patent/JPH069606A/ja active Pending
- 1993-05-20 TW TW082103988A patent/TW382628B/zh active
-
1994
- 1994-08-19 BG BG98990A patent/BG61946B1/bg unknown
- 1994-08-23 FI FI943876A patent/FI943876A0/fi unknown
- 1994-08-25 NO NO943140A patent/NO943140L/no unknown
- 1994-11-10 EE EE9400374A patent/EE03177B1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
LV10099A (lv) | 1994-05-10 |
AU3629693A (en) | 1993-09-13 |
PL175556B1 (pl) | 1999-01-29 |
NO943140D0 (no) | 1994-08-25 |
WO1993017007A1 (en) | 1993-09-02 |
HUT72448A (en) | 1996-04-29 |
AU660067B2 (en) | 1995-06-08 |
BG98990A (bg) | 1995-05-31 |
LV10099B (en) | 1995-02-20 |
CZ205994A3 (en) | 1995-02-15 |
IL104824A0 (en) | 1993-06-10 |
TW382628B (en) | 2000-02-21 |
NO943140L (no) | 1994-08-25 |
SI9300094A (en) | 1993-09-30 |
HRP930210A2 (en) | 1995-06-30 |
FI943876A (fi) | 1994-08-23 |
JPH069606A (ja) | 1994-01-18 |
LTIP354A (lt) | 1994-04-25 |
ZA931278B (en) | 1993-11-18 |
NZ245995A (en) | 1994-09-27 |
SK280143B6 (sk) | 1999-09-10 |
DZ1666A1 (fr) | 2002-02-17 |
EP0558245A1 (en) | 1993-09-01 |
IL104824A (en) | 1999-12-22 |
EG20333A (en) | 1998-10-31 |
SK100794A3 (en) | 1995-04-12 |
AU3377393A (en) | 1993-08-26 |
MX9300977A (es) | 1993-12-01 |
CA2090156A1 (en) | 1993-08-26 |
EE03177B1 (et) | 1999-04-15 |
FI943876A0 (fi) | 1994-08-23 |
HU9402443D0 (en) | 1994-10-28 |
SG65570A1 (en) | 1999-06-22 |
LT3038B (en) | 1994-09-25 |
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