SK279037B6 - Deriváty benzopyránu, medziprodukty pre ich výrobu - Google Patents
Deriváty benzopyránu, medziprodukty pre ich výrobu Download PDFInfo
- Publication number
- SK279037B6 SK279037B6 SK4841-88A SK484188A SK279037B6 SK 279037 B6 SK279037 B6 SK 279037B6 SK 484188 A SK484188 A SK 484188A SK 279037 B6 SK279037 B6 SK 279037B6
- Authority
- SK
- Slovakia
- Prior art keywords
- benzopyran
- dimethyl
- oxide
- dihydro
- group
- Prior art date
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- 150000001562 benzopyrans Chemical class 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 59
- -1 nitrobenzoyl Chemical group 0.000 claims abstract description 59
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 239000002253 acid Substances 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical group 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 18
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 12
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 12
- 125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims abstract description 5
- 125000002950 monocyclic group Chemical class 0.000 claims abstract description 5
- 125000005493 quinolyl group Chemical group 0.000 claims abstract description 5
- 150000007513 acids Chemical class 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 108
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 16
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000006331 halo benzoyl group Chemical group 0.000 claims description 9
- 239000000543 intermediate Substances 0.000 claims description 9
- 208000019553 vascular disease Diseases 0.000 claims description 9
- IPASVSRDRRKZCQ-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] IPASVSRDRRKZCQ-UHFFFAOYSA-N 0.000 claims description 8
- 206010002383 Angina Pectoris Diseases 0.000 claims description 8
- 206010019280 Heart failures Diseases 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 230000002490 cerebral effect Effects 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 230000002093 peripheral effect Effects 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 210000002460 smooth muscle Anatomy 0.000 claims description 7
- 208000029578 Muscle disease Diseases 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- PQVILGHAVGQHRP-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC=[N+]1[O-] PQVILGHAVGQHRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000815 N-oxide group Chemical group 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 4
- SDUIPMRMROTXEI-UHFFFAOYSA-N 2-(2,2-dimethyl-6-nitro-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC([N+]([O-])=O)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] SDUIPMRMROTXEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- YLQHLGXBLFLRRG-CVEARBPZSA-N (3S,4R)-3-hydroxy-2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound C(#N)C=1C=CC2=C([C@@H]([C@@H](C(O2)(C)C)O)C2=[N+](C=CC=C2)[O-])C1 YLQHLGXBLFLRRG-CVEARBPZSA-N 0.000 claims description 3
- HAIDZEBDYGECMV-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxido-5-phenylmethoxypyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C([N+](=C1)[O-])=CC=C1OCC1=CC=CC=C1 HAIDZEBDYGECMV-UHFFFAOYSA-N 0.000 claims description 3
- ZLHVCYUISHRODZ-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxido-5-phenylpyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C([N+](=C1)[O-])=CC=C1C1=CC=CC=C1 ZLHVCYUISHRODZ-UHFFFAOYSA-N 0.000 claims description 3
- KIIGVFITJOATPV-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxido-5-phenylpyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C([N+](=C1)[O-])=CC=C1C1=CC=CC=C1 KIIGVFITJOATPV-UHFFFAOYSA-N 0.000 claims description 3
- PDXPDHODAUINJB-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidoquinolin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound C1=CC=CC2=[N+]([O-])C(C3CC(OC4=CC=C(C=C43)C#N)(C)C)=CC=C21 PDXPDHODAUINJB-UHFFFAOYSA-N 0.000 claims description 3
- CYLXLECDJMEJCZ-UHFFFAOYSA-N 2,2-dimethyl-4-(4-methyl-1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound CC1=CC=[N+]([O-])C(C2C3=CC(=CC=C3OC(C)(C)C2)C#N)=C1 CYLXLECDJMEJCZ-UHFFFAOYSA-N 0.000 claims description 3
- VJFKERVNQSGERR-UHFFFAOYSA-N 2,2-dimethyl-4-(4-methyl-1-oxidopyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound CC1=CC=[N+]([O-])C(C=2C3=CC(=CC=C3OC(C)(C)C=2)C#N)=C1 VJFKERVNQSGERR-UHFFFAOYSA-N 0.000 claims description 3
- HABZKGNATJOHMM-UHFFFAOYSA-N 2,2-dimethyl-4-(5-methyl-1-oxidopyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound [O-][N+]1=CC(C)=CC=C1C1=CC(C)(C)OC2=CC=C(C#N)C=C12 HABZKGNATJOHMM-UHFFFAOYSA-N 0.000 claims description 3
- FVKQXARUEGHHBZ-UHFFFAOYSA-N 2-(2,2-dimethyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] FVKQXARUEGHHBZ-UHFFFAOYSA-N 0.000 claims description 3
- TXMNVLQGLSGKQY-UHFFFAOYSA-N 2-(2,2-dimethylchromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C=1C(C)(C)OC2=CC=CC=C2C=1C1=CC=CC=[N+]1[O-] TXMNVLQGLSGKQY-UHFFFAOYSA-N 0.000 claims description 3
- BAOULIQBYSFCPN-UHFFFAOYSA-N 2-(6-chloro-2,2-dimethyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC(Cl)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] BAOULIQBYSFCPN-UHFFFAOYSA-N 0.000 claims description 3
- ADBQDYGKTRRSEL-UHFFFAOYSA-N 4-(4-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC(Cl)=CC=[N+]1[O-] ADBQDYGKTRRSEL-UHFFFAOYSA-N 0.000 claims description 3
- JDLRFGAYBSYNSO-UHFFFAOYSA-N 4-(5-hydroxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=C(O)C=[N+]1[O-] JDLRFGAYBSYNSO-UHFFFAOYSA-N 0.000 claims description 3
- RFRPNOKJIHDILA-UHFFFAOYSA-N 4-(6-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=CC(Cl)=[N+]1[O-] RFRPNOKJIHDILA-UHFFFAOYSA-N 0.000 claims description 3
- FDTNNVVMCJHQMX-UHFFFAOYSA-N C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC(N)=[N+]1[O-] Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC(N)=[N+]1[O-] FDTNNVVMCJHQMX-UHFFFAOYSA-N 0.000 claims description 3
- AMCKMSXIXYCWLR-UHFFFAOYSA-N [2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromen-6-yl]-(2-iodophenyl)methanone Chemical compound C=1C=C2OC(C)(C)CC(C=3[N+](=CC=CC=3)[O-])C2=CC=1C(=O)C1=CC=CC=C1I AMCKMSXIXYCWLR-UHFFFAOYSA-N 0.000 claims description 3
- WJHHCTQWKLXADZ-UHFFFAOYSA-N [2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromen-6-yl]-(4-iodophenyl)methanone Chemical compound C=1C=C2OC(C)(C)CC(C=3[N+](=CC=CC=3)[O-])C2=CC=1C(=O)C1=CC=C(I)C=C1 WJHHCTQWKLXADZ-UHFFFAOYSA-N 0.000 claims description 3
- QEYPHTFNBPGUFF-UHFFFAOYSA-N [2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromen-6-yl]-(4-nitrophenyl)methanone Chemical compound C=1C=C2OC(C)(C)CC(C=3[N+](=CC=CC=3)[O-])C2=CC=1C(=O)C1=CC=C([N+]([O-])=O)C=C1 QEYPHTFNBPGUFF-UHFFFAOYSA-N 0.000 claims description 3
- YRSPCPACGOAQTP-UHFFFAOYSA-N [2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromen-6-yl]-phenylmethanone Chemical compound C=1C=C2OC(C)(C)CC(C=3[N+](=CC=CC=3)[O-])C2=CC=1C(=O)C1=CC=CC=C1 YRSPCPACGOAQTP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- GFXPTNMIFMZMLJ-UHFFFAOYSA-N methyl 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] GFXPTNMIFMZMLJ-UHFFFAOYSA-N 0.000 claims description 3
- QJGBJSOWUPHNDE-UHFFFAOYSA-N methyl 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)chromene-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2OC(C)(C)C=C1C1=CC=CC=[N+]1[O-] QJGBJSOWUPHNDE-UHFFFAOYSA-N 0.000 claims description 3
- FSWYWPSBVCEELW-UHFFFAOYSA-N methyl 6-(6-cyano-2,2-dimethyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium-3-carboxylate Chemical compound [O-][N+]1=CC(C(=O)OC)=CC=C1C1C2=CC(C#N)=CC=C2OC(C)(C)C1 FSWYWPSBVCEELW-UHFFFAOYSA-N 0.000 claims description 3
- OHCQECSWFLJHIE-UHFFFAOYSA-N 1-[2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromen-6-yl]ethanone Chemical compound C12=CC(C(=O)C)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] OHCQECSWFLJHIE-UHFFFAOYSA-N 0.000 claims description 2
- WZFNSLZNUQFRHC-UHFFFAOYSA-N 1-[2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)chromen-6-yl]ethanone Chemical compound C12=CC(C(=O)C)=CC=C2OC(C)(C)C=C1C1=CC=CC=[N+]1[O-] WZFNSLZNUQFRHC-UHFFFAOYSA-N 0.000 claims description 2
- KZNFWTUXXSJNNN-UHFFFAOYSA-N 1-[2-methyl-4-(1-oxidopyridin-1-ium-2-yl)-2h-chromen-6-yl]ethanone Chemical compound C=1C(C)OC2=CC=C(C(C)=O)C=C2C=1C1=CC=CC=[N+]1[O-] KZNFWTUXXSJNNN-UHFFFAOYSA-N 0.000 claims description 2
- FUOHNAUWNVMQFC-UHFFFAOYSA-N 2,2-dimethyl-4-(3-oxidopyrimidin-3-ium-4-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=NC=[N+]1[O-] FUOHNAUWNVMQFC-UHFFFAOYSA-N 0.000 claims description 2
- JWVRZEWCATZYFU-UHFFFAOYSA-N 2-(2,2-dimethyl-6-nitro-3,4-dihydrochromen-4-yl)-3-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=C[N+]([O-])=C1C1C2=CC([N+]([O-])=O)=CC=C2OC(C)(C)C1 JWVRZEWCATZYFU-UHFFFAOYSA-N 0.000 claims description 2
- AYRYWZHUJGNCCF-UHFFFAOYSA-N 2-(6-bromo-2,2-dimethylchromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C=1C(C)(C)OC2=CC=C(Br)C=C2C=1C1=CC=CC=[N+]1[O-] AYRYWZHUJGNCCF-UHFFFAOYSA-N 0.000 claims description 2
- FYSVSRIAMRZXQA-UHFFFAOYSA-N 2-(6-tert-butyl-2,2-dimethyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC(C(C)(C)C)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] FYSVSRIAMRZXQA-UHFFFAOYSA-N 0.000 claims description 2
- SROWIQULUJSGSQ-UHFFFAOYSA-N 4-(5-amino-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=C(N)C=[N+]1[O-] SROWIQULUJSGSQ-UHFFFAOYSA-N 0.000 claims description 2
- IZVIEWXJZOFDHI-UHFFFAOYSA-N 4-(5-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=C(Cl)C=[N+]1[O-] IZVIEWXJZOFDHI-UHFFFAOYSA-N 0.000 claims description 2
- YHVGOPCDLVPAHA-UHFFFAOYSA-N 4-(5-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=C(Cl)C=[N+]1[O-] YHVGOPCDLVPAHA-UHFFFAOYSA-N 0.000 claims description 2
- XCBLTVOHAWSKKI-UHFFFAOYSA-N C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=CC(N)=[N+]1[O-] Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=CC(N)=[N+]1[O-] XCBLTVOHAWSKKI-UHFFFAOYSA-N 0.000 claims description 2
- GRLZFFAFYZXYQK-UHFFFAOYSA-N [2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromen-6-yl]-(3-iodophenyl)methanone Chemical compound C=1C=C2OC(C)(C)CC(C=3[N+](=CC=CC=3)[O-])C2=CC=1C(=O)C1=CC=CC(I)=C1 GRLZFFAFYZXYQK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- CTTBVZNAWLDBSI-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidoquinolin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound C1=CC=CC2=[N+]([O-])C(C=3C4=CC(=CC=C4OC(C=3)(C)C)C#N)=CC=C21 CTTBVZNAWLDBSI-UHFFFAOYSA-N 0.000 claims 1
- DVOHDQNIFVLXOL-UHFFFAOYSA-N 2-(2,2-dimethyl-6-methylsulfanyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC(SC)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] DVOHDQNIFVLXOL-UHFFFAOYSA-N 0.000 claims 1
- IOXXJICXOVMZAX-UHFFFAOYSA-N 2-(2,2-dimethyl-6-methylsulfonyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC(S(C)(=O)=O)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] IOXXJICXOVMZAX-UHFFFAOYSA-N 0.000 claims 1
- XMKPROQZQOLXKG-UHFFFAOYSA-N 2-(4-methylphenyl)-1-oxidopyridin-1-ium Chemical compound C1=CC(C)=CC=C1C1=CC=CC=[N+]1[O-] XMKPROQZQOLXKG-UHFFFAOYSA-N 0.000 claims 1
- RZZOTQDBNSJNTE-UHFFFAOYSA-N 2-[2,2-dimethyl-6-(trifluoromethyl)chromen-4-yl]-1-oxidopyridin-1-ium Chemical compound C=1C(C)(C)OC2=CC=C(C(F)(F)F)C=C2C=1C1=CC=CC=[N+]1[O-] RZZOTQDBNSJNTE-UHFFFAOYSA-N 0.000 claims 1
- KHCVUHPZYJUXLC-UHFFFAOYSA-N 4-(2-hydroxyphenyl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC=C1O KHCVUHPZYJUXLC-UHFFFAOYSA-N 0.000 claims 1
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 390
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 208
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
- 239000000243 solution Substances 0.000 description 143
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 109
- 239000000203 mixture Substances 0.000 description 99
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 72
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
- 239000000741 silica gel Substances 0.000 description 69
- 229910002027 silica gel Inorganic materials 0.000 description 69
- 229910052938 sodium sulfate Inorganic materials 0.000 description 69
- 235000011152 sodium sulphate Nutrition 0.000 description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- 239000007858 starting material Substances 0.000 description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 56
- 239000003208 petroleum Substances 0.000 description 55
- 239000012074 organic phase Substances 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 36
- 235000017557 sodium bicarbonate Nutrition 0.000 description 36
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 36
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 31
- 239000007787 solid Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
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- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
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- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
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- 208000024963 hair loss Diseases 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
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- 238000011534 incubation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000008011 inorganic excipient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- DKXULEFCEORBJK-UHFFFAOYSA-N magnesium;octadecanoic acid Chemical compound [Mg].CCCCCCCCCCCCCCCCCC(O)=O DKXULEFCEORBJK-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 208000026440 premature labor Diseases 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- KWGXEOLVIDRMDD-UHFFFAOYSA-N trimethyl-(3-methylphenyl)stannane Chemical compound CC1=CC=CC([Sn](C)(C)C)=C1 KWGXEOLVIDRMDD-UHFFFAOYSA-N 0.000 description 1
- BTMMIGGFWWXPEE-UHFFFAOYSA-N trimethyl-(4-methylphenyl)stannane Chemical compound CC1=CC=C([Sn](C)(C)C)C=C1 BTMMIGGFWWXPEE-UHFFFAOYSA-N 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878715839A GB8715839D0 (en) | 1987-07-06 | 1987-07-06 | Benzopyran derivatives |
| GB888810212A GB8810212D0 (en) | 1987-07-06 | 1988-04-29 | Benzopyran derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK484188A3 SK484188A3 (en) | 1998-05-06 |
| SK279037B6 true SK279037B6 (sk) | 1998-05-06 |
Family
ID=26292440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK4841-88A SK279037B6 (sk) | 1987-07-06 | 1988-07-04 | Deriváty benzopyránu, medziprodukty pre ich výrobu |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US4971982A (cs) |
| EP (1) | EP0298452B1 (cs) |
| JP (1) | JP2683581B2 (cs) |
| CN (1) | CN1023404C (cs) |
| AR (1) | AR245710A1 (cs) |
| AT (1) | ATE91127T1 (cs) |
| AU (1) | AU613646B2 (cs) |
| CA (1) | CA1334094C (cs) |
| CZ (1) | CZ285970B6 (cs) |
| DE (1) | DE3882095D1 (cs) |
| DK (1) | DK370988A (cs) |
| DZ (1) | DZ1227A1 (cs) |
| ES (1) | ES2056859T3 (cs) |
| FI (1) | FI90079C (cs) |
| HU (2) | HU202513B (cs) |
| IE (1) | IE62258B1 (cs) |
| IL (1) | IL86923A (cs) |
| IS (1) | IS1596B (cs) |
| MC (1) | MC1953A1 (cs) |
| MX (1) | MX174083B (cs) |
| NO (1) | NO170727C (cs) |
| NZ (1) | NZ225163A (cs) |
| PH (1) | PH27153A (cs) |
| PT (1) | PT87913B (cs) |
| SK (1) | SK279037B6 (cs) |
| SU (1) | SU1757466A3 (cs) |
| YU (1) | YU46918B (cs) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5387587A (en) * | 1986-12-23 | 1995-02-07 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Chroman derivatives |
| US5284838A (en) * | 1987-06-23 | 1994-02-08 | Elf Sanofi | Use of 2,2-dimethylchroman-3-ol derivatives in the treatment of asthma |
| US4971982A (en) * | 1987-07-06 | 1990-11-20 | Hoffmann-La Roche Inc. | Benzopyran derivatives |
| AU628331B2 (en) * | 1988-05-06 | 1992-09-17 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Chroman derivatives |
| DE3918041A1 (de) * | 1989-06-02 | 1990-12-06 | Merck Patent Gmbh | Chromanderivate |
| DE3922392A1 (de) * | 1989-07-07 | 1991-01-17 | Merck Patent Gmbh | Chromanderivate |
| DE3924417A1 (de) * | 1989-07-24 | 1991-01-31 | Merck Patent Gmbh | Chromanderivate |
| DE3926001A1 (de) * | 1989-08-05 | 1991-02-07 | Merck Patent Gmbh | Chromanderivate |
| US5420151A (en) * | 1989-12-22 | 1995-05-30 | Aktiebolaget Astra | Chroman derivatives |
| US5616610A (en) * | 1989-12-22 | 1997-04-01 | Astra Aktiebolag | (R)-5-carbamoyl-8-fluoro-3-N,N-disubstituted-amino-3,4-dihydro-2H-1-benzopyrans |
| CN1060467A (zh) | 1990-09-25 | 1992-04-22 | 武田药品工业株式会社 | 1，3-苯并嗪衍生物、其生产方法和用途 |
| CA2061179A1 (en) * | 1991-02-18 | 1992-08-19 | Ryuji Tsuzuki | Oxzazinobenzazole compounds |
| DE4115465A1 (de) * | 1991-05-11 | 1992-11-12 | Beiersdorf Ag | Neue in 4-stellung durch aryl oder n-heteroaryl substituierte 2h-benzo(b)pyran-derivate, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen |
| KR950009863B1 (ko) * | 1991-05-22 | 1995-08-29 | 재단법인한국화학연구소 | 벤조피란 유도체와 그의 제조방법 |
| FR2698873B1 (fr) * | 1992-12-07 | 1995-02-24 | Lipha | Benzocycloheptènes, benzoxépines et benzothiépines activateurs des canaux potassiques, procédé de préparation, composition pharmaceutique les contenant. |
| CN1044605C (zh) * | 1992-08-17 | 1999-08-11 | 中外制药株式会社 | 苯并吡喃和苯并嗪衍生物 |
| ES2064228B1 (es) * | 1992-10-19 | 1995-09-01 | Uriach & Cia Sa J | Nuevas tetralonas con actividad farmacologica, composiciones que las contienen y procedimiento para su preparacion. |
| US5416097A (en) * | 1993-05-19 | 1995-05-16 | Berlex Laboratories, Inc. | Potassium channel activators/openers |
| US5837702A (en) * | 1993-10-07 | 1998-11-17 | Bristol-Myers Squibb Co. | 4-arylamino-benzopyran and related compounds |
| US5719155A (en) * | 1993-11-10 | 1998-02-17 | Japan Tobacco Inc. | Chroman derivative and pharmaceutical use thereof |
| WO1995033726A1 (en) * | 1994-06-09 | 1995-12-14 | Ss Pharmaceutical Co., Ltd. | 4-quinolinone derivative or salt thereof |
| US5470861A (en) * | 1994-08-04 | 1995-11-28 | Hoffmann-La Roche Inc. | Method of promoting hair growth |
| GB9510477D0 (en) * | 1995-05-24 | 1995-07-19 | Sandoz Ltd | Organic compounds |
| US5869478A (en) * | 1995-06-07 | 1999-02-09 | Bristol-Myers Squibb Company | Sulfonamido substituted benzopyran derivatives |
| US5612370A (en) * | 1995-06-07 | 1997-03-18 | Bristol-Myers Squibb Company | Phenylglycine and phenylalaninen amido benzopyran derivatives |
| US5629429A (en) * | 1995-06-07 | 1997-05-13 | Bristol-Myers Squibb Company | Process for preparing 4-arylamino-benzopyran and related compounds |
| US5612323A (en) * | 1995-06-07 | 1997-03-18 | Bristol-Myers Squibb Company | Phosphinic ester substituted benzopyran derivatives |
| KR100691511B1 (ko) * | 1995-11-09 | 2007-04-19 | 다우 아그로사이언시즈 엘엘씨 | 크로만카복실레이트의제조방법 |
| JP3885900B2 (ja) * | 1996-03-22 | 2007-02-28 | 大日本インキ化学工業株式会社 | ベンゾピラン誘導体及びそれを有効成分とする心臓疾患治療剤 |
| WO1999001453A1 (en) * | 1997-07-02 | 1999-01-14 | F. Hoffmann-La Roche Ag | A process for the manufacture of optically active chromanylpyridine derivatives |
| US7045519B2 (en) * | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| EP1087963B1 (en) | 1998-06-19 | 2004-08-25 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| US6455554B1 (en) | 1999-06-07 | 2002-09-24 | Targacept, Inc. | Oxopyridinyl pharmaceutical compositions and methods for use |
| FI20010233A0 (fi) * | 2001-02-08 | 2001-02-08 | Orion Corp | Menetelmä sydämen vajaatoiminnan hoitoon |
| AR035087A1 (es) * | 2001-08-09 | 2004-04-14 | Syngenta Participations Ag | Piridil-alquinos y piridil-n-oxido-alquinos herbicidas activos, procedimiento para su preparacion, composicion herbicida y para inhibir el crecimiento de plantas, metodo para el control del crecimiento de plantas indeseables , y metodo para la inhibicion del crecimiento de plantas |
| AR040413A1 (es) * | 2002-05-31 | 2005-04-06 | Syngenta Participations Ag | Heterociclilalquinos activos como herbicidas |
| ES2379098T3 (es) * | 2005-09-01 | 2012-04-20 | Janssen Pharmaceutica Nv | Derivados de benzopirano novedosos como abridores del canal de potasio |
| US7812183B2 (en) * | 2005-09-01 | 2010-10-12 | Janssen Pharmaceutica Nv | Benzopyran derivatives as potassium channel openers |
| WO2008072801A1 (en) * | 2006-12-13 | 2008-06-19 | Seoul National University Industry Foundation | Compounds with embedded benzopyran motif for core structures and preparation method thereof |
| CN103819395B (zh) * | 2014-02-24 | 2016-05-25 | 蚌埠中实化学技术有限公司 | 一种制备2-碘-5-苯基吡啶的方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1583811A (en) * | 1977-05-09 | 1981-02-04 | Laroche Navarron Sa | Chromene derivatives |
| US4563468A (en) * | 1979-09-13 | 1986-01-07 | Burroughs Wellcome Co. | Chemotherapeutic agents |
| HU184359B (en) * | 1980-12-16 | 1984-08-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing substituted acyl-carbamides |
| US4443459A (en) * | 1981-05-26 | 1984-04-17 | Banyu Pharmaceutical Co., Ltd. | α-Tocopheryl ester of 5-substituted picolinic acid and hypotensive composition containing it |
| GB2107706A (en) * | 1981-09-25 | 1983-05-05 | Beecham Group Plc | Benzopyrans |
| DE3364734D1 (en) * | 1982-10-19 | 1986-08-28 | Beecham Group Plc | Novel chromans and chromenes |
| DE3579390D1 (de) * | 1984-06-22 | 1990-10-04 | Beecham Group Plc | Wirksame benzopyranverbindungen. |
| EP0218373B1 (en) * | 1985-09-11 | 1990-03-07 | Beecham Group Plc | Chroman derivatives and analogues having antihypertensive activity |
| PT84806B (pt) * | 1986-05-03 | 1989-12-29 | Beecham Group Plc | Processo para a preparacao de benzopiranos |
| FI90343C (fi) * | 1987-06-23 | 1994-01-25 | Merck Patent Gmbh | Menetelmä korkeaa verenpainetta alentavien ja rytmihäiriöitä vastustavien trans-2,2-dimetyylikroman-3-olijohdannaisten valmistamiseksi |
| US4971982A (en) * | 1987-07-06 | 1990-11-20 | Hoffmann-La Roche Inc. | Benzopyran derivatives |
-
1988
- 1988-06-23 US US07/210,692 patent/US4971982A/en not_active Expired - Fee Related
- 1988-06-24 NZ NZ225163A patent/NZ225163A/en unknown
- 1988-06-30 AU AU18556/88A patent/AU613646B2/en not_active Ceased
- 1988-06-30 IL IL8692388A patent/IL86923A/en not_active IP Right Cessation
- 1988-07-03 DZ DZ880098A patent/DZ1227A1/fr active
- 1988-07-04 SK SK4841-88A patent/SK279037B6/sk unknown
- 1988-07-04 CZ CS884841A patent/CZ285970B6/cs not_active IP Right Cessation
- 1988-07-04 MC MC881987A patent/MC1953A1/fr unknown
- 1988-07-04 AR AR88311317A patent/AR245710A1/es active
- 1988-07-04 HU HU883471A patent/HU202513B/hu not_active IP Right Cessation
- 1988-07-04 DK DK370988A patent/DK370988A/da not_active Application Discontinuation
- 1988-07-05 JP JP63166068A patent/JP2683581B2/ja not_active Expired - Lifetime
- 1988-07-05 PT PT87913A patent/PT87913B/pt not_active IP Right Cessation
- 1988-07-05 SU SU884356220A patent/SU1757466A3/ru active
- 1988-07-05 CA CA000571115A patent/CA1334094C/en not_active Expired - Fee Related
- 1988-07-05 YU YU130288A patent/YU46918B/sh unknown
- 1988-07-05 MX MX1216888A patent/MX174083B/es unknown
- 1988-07-05 NO NO883007A patent/NO170727C/no not_active IP Right Cessation
- 1988-07-05 IE IE204388A patent/IE62258B1/en not_active IP Right Cessation
- 1988-07-05 CN CN88104200A patent/CN1023404C/zh not_active Expired - Fee Related
- 1988-07-05 IS IS3369A patent/IS1596B/is unknown
- 1988-07-06 FI FI883232A patent/FI90079C/fi not_active IP Right Cessation
- 1988-07-06 DE DE8888110789T patent/DE3882095D1/de not_active Expired - Fee Related
- 1988-07-06 PH PH37176A patent/PH27153A/en unknown
- 1988-07-06 EP EP88110789A patent/EP0298452B1/de not_active Expired - Lifetime
- 1988-07-06 ES ES88110789T patent/ES2056859T3/es not_active Expired - Lifetime
- 1988-07-06 AT AT88110789T patent/ATE91127T1/de not_active IP Right Cessation
-
1990
- 1990-09-11 US US07/580,881 patent/US5118694A/en not_active Expired - Fee Related
-
1995
- 1995-06-19 HU HU95P/P00257P patent/HU211870A9/hu unknown
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