LT3038B - Heterobicyclic compounds - Google Patents
Heterobicyclic compounds Download PDFInfo
- Publication number
- LT3038B LT3038B LTIP354A LTIP354A LT3038B LT 3038 B LT3038 B LT 3038B LT IP354 A LTIP354 A LT IP354A LT IP354 A LTIP354 A LT IP354A LT 3038 B LT3038 B LT 3038B
- Authority
- LT
- Lithuania
- Prior art keywords
- methyl
- oxo
- benzopyran
- phenyl
- piperazinyl
- Prior art date
Links
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 455
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 10
- 239000000651 prodrug Substances 0.000 claims abstract description 9
- 229940002612 prodrug Drugs 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical group C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 hydroxymethylene group Chemical group 0.000 claims description 228
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 169
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 64
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 46
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 41
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- LPACBRAWRCXZGB-UHFFFAOYSA-N 3-methyl-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 LPACBRAWRCXZGB-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical compound O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000006308 propyl amino group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- JCIDEANDDNSHQC-UHFFFAOYSA-N 4H-chromene Chemical compound C1=CC=C2CC=COC2=C1 JCIDEANDDNSHQC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 4
- OJXOWGJHAMWLIZ-UHFFFAOYSA-N 2-phenyl-4h-chromene Chemical compound O1C2=CC=CC=C2CC=C1C1=CC=CC=C1 OJXOWGJHAMWLIZ-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 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 description 2
- 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 description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino 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
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[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
- 125000004193 piperazinyl group Chemical group 0.000 claims 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
- 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
- AMUIEDQXJUZYCZ-UHFFFAOYSA-N 3-methyl-8-[2-[4-(2-methylphenyl)piperazin-1-yl]acetyl]-2-phenylchromen-4-one Chemical compound CC1=CC=CC=C1N1CCN(CC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 AMUIEDQXJUZYCZ-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
- JDAUINVSCGMHMP-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)butanamide Chemical compound COC1=CC=CC=C1N1CCN(CCCC(=O)NC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 JDAUINVSCGMHMP-UHFFFAOYSA-N 0.000 claims 1
- NUXJIGIXAYKHLS-UHFFFAOYSA-N 8-[1-hydroxy-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 NUXJIGIXAYKHLS-UHFFFAOYSA-N 0.000 claims 1
- DIINRQCXLCEVHL-UHFFFAOYSA-N 8-[1-hydroxy-2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one Chemical compound CC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 DIINRQCXLCEVHL-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
- FMYFHINQACBOCS-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCOC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 FMYFHINQACBOCS-UHFFFAOYSA-N 0.000 claims 1
- ATFLWMRUEKKWBC-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylamino]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 ATFLWMRUEKKWBC-UHFFFAOYSA-N 0.000 claims 1
- TTWAZPUHJYFZBE-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylsulfonyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCS(=O)(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 TTWAZPUHJYFZBE-UHFFFAOYSA-N 0.000 claims 1
- WBWMQLSFKCZZKH-UHFFFAOYSA-N 8-[[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl-methylamino]methyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCN(C)CC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 WBWMQLSFKCZZKH-UHFFFAOYSA-N 0.000 claims 1
- AJLQOIWTUULSNB-UHFFFAOYSA-N [8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylcarbamoyl]-3-methyl-4-oxo-2-phenylchromen-6-yl] acetate Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(OC(C)=O)C=2)CC1 AJLQOIWTUULSNB-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- BUGZODXDBBCPKQ-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-(4-phenylphenyl)chromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(=CC=3)C=3C=CC=CC=3)=O)C=CC=2)CC1 BUGZODXDBBCPKQ-UHFFFAOYSA-N 0.000 claims 1
- KXLPEPDVRPPMRV-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-pyridin-3-ylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=NC=CC=3)=O)C=CC=2)CC1 KXLPEPDVRPPMRV-UHFFFAOYSA-N 0.000 claims 1
- NPJCJQQKGMFUDQ-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C=CO3)=O)C=CC=2)CC1 NPJCJQQKGMFUDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 11
- 150000001412 amines Chemical class 0.000 abstract description 5
- 210000001635 urinary tract Anatomy 0.000 abstract description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 2
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 abstract 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 466
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 358
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 333
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 332
- 239000000543 intermediate Substances 0.000 description 285
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 246
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 210
- 239000000243 solution Substances 0.000 description 206
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 198
- 239000000203 mixture Substances 0.000 description 166
- 239000002904 solvent Substances 0.000 description 163
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 142
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 125
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 116
- 238000006243 chemical reaction Methods 0.000 description 113
- 235000019439 ethyl acetate Nutrition 0.000 description 111
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 108
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
- 239000011541 reaction mixture Substances 0.000 description 84
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 83
- 239000002244 precipitate Substances 0.000 description 81
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
- 239000002585 base Substances 0.000 description 65
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 62
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 62
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
- 238000010992 reflux Methods 0.000 description 54
- 239000000741 silica gel Substances 0.000 description 52
- 229910002027 silica gel Inorganic materials 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
- 238000004587 chromatography analysis Methods 0.000 description 41
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 40
- 230000008018 melting Effects 0.000 description 39
- 238000002844 melting Methods 0.000 description 39
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 38
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 38
- 239000012044 organic layer Substances 0.000 description 38
- 238000000034 method Methods 0.000 description 36
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 35
- 230000002378 acidificating effect Effects 0.000 description 35
- 239000003208 petroleum Substances 0.000 description 35
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 34
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
- 238000003756 stirring Methods 0.000 description 32
- 229910000027 potassium carbonate Inorganic materials 0.000 description 31
- 229960000583 acetic acid Drugs 0.000 description 29
- 239000002253 acid Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 28
- 238000001914 filtration Methods 0.000 description 26
- 238000000746 purification Methods 0.000 description 26
- 238000010898 silica gel chromatography Methods 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000012074 organic phase Substances 0.000 description 24
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 23
- 239000012043 crude product Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- 238000009835 boiling Methods 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- LHRAZWLERDCLKI-UHFFFAOYSA-N methanesulfonic acid;3-methyl-4-oxo-2-phenyl-n-[3-(4-phenylpiperidin-1-yl)propyl]chromene-8-carboxamide Chemical compound CS(O)(=O)=O.C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCC1C1=CC=CC=C1 LHRAZWLERDCLKI-UHFFFAOYSA-N 0.000 description 1
- YDNWEWRESFNRNT-UHFFFAOYSA-N methanesulfonic acid;6-methoxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound CS(O)(=O)=O.C=12OC(C=3C=CC=CC=3)=C(C)C(=O)C2=CC(OC)=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC YDNWEWRESFNRNT-UHFFFAOYSA-N 0.000 description 1
- OIXMUQLVDNPHNS-UHFFFAOYSA-N methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O OIXMUQLVDNPHNS-UHFFFAOYSA-N 0.000 description 1
- BKECANHXSQKLDQ-UHFFFAOYSA-N methanesulfonic acid;n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carbothioamide Chemical compound CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCNC(=S)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 BKECANHXSQKLDQ-UHFFFAOYSA-N 0.000 description 1
- LJVXNCIDACCFEG-UHFFFAOYSA-N methanesulfonic acid;n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-2,3-dihydrochromene-8-carboxamide Chemical compound CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C=3OCCC(=O)C=3C=CC=2)CC1 LJVXNCIDACCFEG-UHFFFAOYSA-N 0.000 description 1
- PRYBKJQGIMYELW-UHFFFAOYSA-N methanesulfonic acid;n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-2-phenylchromene-8-carboxamide Chemical compound CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 PRYBKJQGIMYELW-UHFFFAOYSA-N 0.000 description 1
- VCTSUHVBLAJSOI-UHFFFAOYSA-N methanesulfonic acid;n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxochromene-8-carboxamide Chemical compound CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C=CO3)=O)C=CC=2)CC1 VCTSUHVBLAJSOI-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BAQGCWNPCFABAY-UHFFFAOYSA-N methyl 2-sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S BAQGCWNPCFABAY-UHFFFAOYSA-N 0.000 description 1
- ZTIFDLYMYBXRLT-UHFFFAOYSA-N methyl 3-methyl-2-(4-methylphenyl)-4-oxochromene-8-carboxylate Chemical compound COC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=C(C)C=C1 ZTIFDLYMYBXRLT-UHFFFAOYSA-N 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
- JHEGXAJWTZBWPX-UHFFFAOYSA-N n-(2-chloroethyl)-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound O1C2=C(C(=O)NCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 JHEGXAJWTZBWPX-UHFFFAOYSA-N 0.000 description 1
- GOLLEUIGUXTIQM-UHFFFAOYSA-N n-(2-chloroethyl)-n-[(3-methyl-4-oxo-2-phenylchromen-8-yl)methyl]acetamide Chemical compound ClCCN(C(=O)C)CC1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 GOLLEUIGUXTIQM-UHFFFAOYSA-N 0.000 description 1
- JICPGKVAZANWHF-UHFFFAOYSA-N n-(3-aminopropyl)-3-methyl-4-oxo-2-phenylchromene-8-carboxamide;hydrochloride Chemical compound Cl.O1C2=C(C(=O)NCCCN)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 JICPGKVAZANWHF-UHFFFAOYSA-N 0.000 description 1
- ARIWQLAPCTWAQV-UHFFFAOYSA-N n-(3-methyl-4-oxo-2-phenylchromen-8-yl)prop-2-enamide Chemical compound O1C2=C(NC(=O)C=C)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 ARIWQLAPCTWAQV-UHFFFAOYSA-N 0.000 description 1
- XNCPRQNVRBNOKB-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n,3-dimethyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C)C(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 XNCPRQNVRBNOKB-UHFFFAOYSA-N 0.000 description 1
- YWSUCLWWSZFZMG-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-3-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C=4C=CC=CC=4)=CO3)=O)C=CC=2)CC1 YWSUCLWWSZFZMG-UHFFFAOYSA-N 0.000 description 1
- QZFOKLPWYHXGFN-UHFFFAOYSA-N n-acetyl-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound CC(=O)NC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 QZFOKLPWYHXGFN-UHFFFAOYSA-N 0.000 description 1
- CIIUNVUCNBEPEA-UHFFFAOYSA-N n-acetyl-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCN(C(C)=O)C(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 CIIUNVUCNBEPEA-UHFFFAOYSA-N 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- MTOBMVSFIUMGHO-UHFFFAOYSA-N n-methyl-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)prop-2-enamide Chemical compound C=CC(=O)N(C)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 MTOBMVSFIUMGHO-UHFFFAOYSA-N 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- WDBXHQTZERVTGM-UHFFFAOYSA-N o-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]hydroxylamine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCON)CC1 WDBXHQTZERVTGM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 229960001289 prazosin Drugs 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- KZTMCBOPTQHICJ-UHFFFAOYSA-N propanoyl benzoate Chemical compound CCC(=O)OC(=O)C1=CC=CC=C1 KZTMCBOPTQHICJ-UHFFFAOYSA-N 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical group C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000000050 smooth muscle relaxant Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- VLLATRQRPYHZLR-UHFFFAOYSA-M sodium;3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound [Na+].O1C2=C(C([O-])=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 VLLATRQRPYHZLR-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000003883 substance clean up Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229950003559 terflavoxate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 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
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 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
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- 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 (2)
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 |
Publications (2)
Publication Number | Publication Date |
---|---|
LTIP354A LTIP354A (lt) | 1994-04-25 |
LT3038B true LT3038B (en) | 1994-09-25 |
Family
ID=26330842
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LTIP354A LT3038B (en) | 1992-02-25 | 1993-02-24 | Heterobicyclic compounds |
Country Status (25)
Country | Link |
---|---|
EP (1) | EP0558245A1 (cs) |
JP (1) | JPH069606A (cs) |
AU (2) | AU3629693A (cs) |
BG (1) | BG61946B1 (cs) |
CA (1) | CA2090156A1 (cs) |
CZ (1) | CZ205994A3 (cs) |
DZ (1) | DZ1666A1 (cs) |
EE (1) | EE03177B1 (cs) |
EG (1) | EG20333A (cs) |
FI (1) | FI943876A (cs) |
HR (1) | HRP930210A2 (cs) |
HU (1) | HUT72448A (cs) |
IL (1) | IL104824A (cs) |
LT (1) | LT3038B (cs) |
LV (1) | LV10099B (cs) |
MX (1) | MX9300977A (cs) |
NO (1) | NO943140D0 (cs) |
NZ (1) | NZ245995A (cs) |
PL (1) | PL175556B1 (cs) |
SG (1) | SG65570A1 (cs) |
SI (1) | SI9300094A (cs) |
SK (1) | SK280143B6 (cs) |
TW (1) | TW382628B (cs) |
WO (1) | WO1993017007A1 (cs) |
ZA (1) | ZA931278B (cs) |
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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 |
EP0690051B1 (en) * | 1994-01-14 | 2001-07-18 | Azwell Inc. | Diazacycloalkanealkylsulfonamide derivative |
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. |
ES2160158T3 (es) * | 1994-03-30 | 2001-11-01 | Zeria Pharm Co Ltd | Derivados de 4-indol-1-il acido butirico, su preparacion y su utilizacion como inhibidores de receptores alfa1-adrenergicos y testosterona 5alfa-reductasas. |
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 |
AU695633B2 (en) * | 1995-02-28 | 1998-08-20 | Asubio Pharma Co., Ltd. | Arylpiperidine and arylpiperazine derivatives and medicament 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 |
PT748800E (pt) * | 1995-06-09 | 2001-10-30 | Hoffmann La Roche | Derivados de pirimidinadiona pirimidinatriona triazinadiona como antagonistas do receptor alfa-1-adrenergico |
JPH0967367A (ja) * | 1995-06-23 | 1997-03-11 | Suntory Ltd | チオピラン誘導体 |
AU4153496A (en) * | 1995-10-20 | 1997-05-07 | 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 |
WO1997032870A1 (fr) * | 1996-03-08 | 1997-09-12 | Synthelabo | Derives de 2-aminoethyl-benzofurane, leur preparation et leur application en therapeutique |
FR2745815B1 (fr) * | 1996-03-08 | 1998-06-26 | Synthelabo | Derives de benzofurane, leur preparations et compositions pharmaceutiques les comprenant |
AU3817197A (en) * | 1996-08-22 | 1998-03-06 | 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 |
PT984777E (pt) * | 1997-05-12 | 2004-01-30 | Ortho Mcneil Pharm Inc | Piperazinas arilsubstituidas uteis no tratamento da hiperplasia benigna da prostata |
AU7455798A (en) | 1997-06-04 | 1998-12-21 | Nippon Shoji Kaisha, Ltd. | Process for producing piperazinesulfonamide derivatives and salts thereof |
AU8130298A (en) * | 1997-07-15 | 1999-02-10 | Sankyo Company Limited | Piperazine derivatives |
US6306861B1 (en) | 1999-07-30 | 2001-10-23 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyrancecarboxamide derivatives |
US6387909B1 (en) | 1999-07-30 | 2002-05-14 | Recordati S.A. Chemical And Pharmaceutical Company | Thienopyranecarboxamide derivatives |
IT1313581B1 (it) * | 1999-07-30 | 2002-09-09 | Recordati Chem Pharm | Derivati tienopirancarbossamidici. |
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 |
WO2004041279A1 (en) * | 2002-10-30 | 2004-05-21 | Merck & Co., Inc. | Gamma-aminoamide modulators of chemokine receptor activity |
US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
MX2007000481A (es) | 2004-07-14 | 2007-03-29 | Ptc Therapeutics Inc | Metodos para tratar 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 |
CN101022802A (zh) | 2004-07-22 | 2007-08-22 | Ptc医疗公司 | 用于治疗丙型肝炎的噻吩并吡啶化合物 |
GT200600078A (es) | 2005-02-17 | 2007-04-12 | Derivados de indol, benzotiofeno, benzofurano e indeno cicloalquil condensados | |
WO2010037127A1 (en) * | 2008-09-29 | 2010-04-01 | Sirtris Pharmaceuticals, Inc. | Chromenone analogs as sirtuin modulators |
CZ2012242A3 (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 |
WO2017139274A1 (en) | 2016-02-09 | 2017-08-17 | Pharmakea, Inc. | Quinolinone lysyl oxidase-like 2 inhibitors and uses thereof |
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 |
US11986779B2 (en) | 2019-11-11 | 2024-05-21 | Southwest Research Institute | Recrystallized HI-6 dimethylsulfate |
CR20220316A (es) | 2019-12-06 | 2022-10-07 | Vertex Pharma | Tetrahidrofuranos sustituidos como moduladores de canales de sodio |
WO2022256622A1 (en) | 2021-06-04 | 2022-12-08 | Vertex Pharmaceuticals Incorporated | N-(hydroxyalkyl (hetero)aryl) tetrahydrofuran carboxamides as modulators of sodium channels |
TW202334089A (zh) | 2021-11-02 | 2023-09-01 | 美商夫雷爾醫療公司 | Pparg反向激動劑及其用途 |
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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GB1156973A (en) | 1965-07-06 | 1969-07-02 | Quinazoline Derivatives | |
EP0072620A1 (en) | 1981-07-17 | 1983-02-23 | RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY | 3-Methylflavone-8-carboxylic acid esters |
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US2921070A (en) * | 1957-11-05 | 1960-01-12 | Recordati Lab Farmacologico S | Basic esters of 3-methylflavone-8-carboxylic acid |
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 |
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 EP EP93301264A patent/EP0558245A1/en not_active Withdrawn
- 1993-02-22 SG SG1996004802A patent/SG65570A1/en unknown
- 1993-02-22 HR HR930210A patent/HRP930210A2/hr not_active Application Discontinuation
- 1993-02-23 AU AU36296/93A patent/AU3629693A/en not_active Abandoned
- 1993-02-23 SK SK1007-94A patent/SK280143B6/sk unknown
- 1993-02-23 WO PCT/EP1993/000420 patent/WO1993017007A1/en not_active Application Discontinuation
- 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 CA CA002090156A patent/CA2090156A1/en not_active Abandoned
- 1993-02-23 CZ CZ942059A patent/CZ205994A3/cs unknown
- 1993-02-23 HU HU9402443A patent/HUT72448A/hu unknown
- 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
- 1993-02-24 DZ DZ930019A patent/DZ1666A1/fr active
- 1993-02-24 ZA ZA931278A patent/ZA931278B/xx unknown
- 1993-02-25 NZ NZ245995A patent/NZ245995A/en unknown
- 1993-02-25 EG EG1193A patent/EG20333A/xx active
- 1993-02-25 SI SI19939300094A patent/SI9300094A/sl 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/FI943876A/fi unknown
- 1994-08-25 NO NO943140A patent/NO943140D0/no unknown
- 1994-11-10 EE EE9400374A patent/EE03177B1/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1156973A (en) | 1965-07-06 | 1969-07-02 | Quinazoline Derivatives | |
EP0072620A1 (en) | 1981-07-17 | 1983-02-23 | RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY | 3-Methylflavone-8-carboxylic acid esters |
Non-Patent Citations (1)
Title |
---|
T.W. GREENE: "Protective groups in organic sythesis", pages: 87 |
Also Published As
Publication number | Publication date |
---|---|
WO1993017007A1 (en) | 1993-09-02 |
AU3377393A (en) | 1993-08-26 |
HU9402443D0 (en) | 1994-10-28 |
NO943140L (no) | 1994-08-25 |
HRP930210A2 (en) | 1995-06-30 |
JPH069606A (ja) | 1994-01-18 |
CA2090156A1 (en) | 1993-08-26 |
SK100794A3 (en) | 1995-04-12 |
NO943140D0 (no) | 1994-08-25 |
FI943876A0 (fi) | 1994-08-23 |
SK280143B6 (sk) | 1999-09-10 |
EP0558245A1 (en) | 1993-09-01 |
AU3629693A (en) | 1993-09-13 |
TW382628B (en) | 2000-02-21 |
PL175556B1 (pl) | 1999-01-29 |
MX9300977A (es) | 1993-12-01 |
LV10099B (en) | 1995-02-20 |
DZ1666A1 (fr) | 2002-02-17 |
IL104824A (en) | 1999-12-22 |
SI9300094A (en) | 1993-09-30 |
BG98990A (bg) | 1995-05-31 |
NZ245995A (en) | 1994-09-27 |
HUT72448A (en) | 1996-04-29 |
AU660067B2 (en) | 1995-06-08 |
ZA931278B (en) | 1993-11-18 |
BG61946B1 (bg) | 1998-10-30 |
LTIP354A (lt) | 1994-04-25 |
EE03177B1 (et) | 1999-04-15 |
IL104824A0 (en) | 1993-06-10 |
FI943876A (fi) | 1994-08-23 |
LV10099A (lv) | 1994-05-10 |
SG65570A1 (en) | 1999-06-22 |
EG20333A (en) | 1998-10-31 |
CZ205994A3 (en) | 1995-02-15 |
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