IE44588B1 - Trans-4-heterocyclyl-3,4-dihidro-2h-benzo(b)pyran-3-ol esters - Google Patents
Trans-4-heterocyclyl-3,4-dihidro-2h-benzo(b)pyran-3-ol estersInfo
- Publication number
- IE44588B1 IE44588B1 IE161/77A IE16177A IE44588B1 IE 44588 B1 IE44588 B1 IE 44588B1 IE 161/77 A IE161/77 A IE 161/77A IE 16177 A IE16177 A IE 16177A IE 44588 B1 IE44588 B1 IE 44588B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- group
- trans
- benzo
- nitro
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical group C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 6
- -1 Trans-4-piperidino-3,4-dihydro-2,2-dimethyl-6-nitro2H-benzo[b]-pyran-3-yl acetate Chemical compound 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 3
- 239000002220 antihypertensive agent Substances 0.000 abstract description 3
- 239000002934 diuretic Substances 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 239000002876 beta blocker Substances 0.000 abstract 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 abstract 1
- 229940030606 diuretics Drugs 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 229940097258 other antihypertensives in atc Drugs 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241000400611 Eucalyptus deanei Species 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000035488 systolic blood pressure Effects 0.000 description 3
- ACUOAQKUXNEDQR-UHFFFAOYSA-N 2,2-dimethyl-7-nitrochromene Chemical compound [O-][N+](=O)C1=CC=C2C=CC(C)(C)OC2=C1 ACUOAQKUXNEDQR-UHFFFAOYSA-N 0.000 description 2
- BYCZNQTXVXAMPC-UHFFFAOYSA-N 2h-pyran-3-yl acetate Chemical compound CC(=O)OC1=CC=COC1 BYCZNQTXVXAMPC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YAHAPDMLSIZCRN-UHFFFAOYSA-N 1-nitro-3-prop-2-ynoxybenzene Chemical compound [O-][N+](=O)C1=CC=CC(OCC#C)=C1 YAHAPDMLSIZCRN-UHFFFAOYSA-N 0.000 description 1
- MJVCBDKNZRGZDF-UHFFFAOYSA-N 2,2-dimethyl-6-nitrochromene Chemical compound C1=C([N+]([O-])=O)C=C2C=CC(C)(C)OC2=C1 MJVCBDKNZRGZDF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZVDOCKBHGYRFGF-UHFFFAOYSA-N 2-nitro-2H-chromen-3-ol Chemical compound [N+](=O)([O-])C1C(=CC2=C(O1)C=CC=C2)O ZVDOCKBHGYRFGF-UHFFFAOYSA-N 0.000 description 1
- KTZFWSARJPRMTD-UHFFFAOYSA-N 2H-pyran-3-yl benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC=1COC=CC=1 KTZFWSARJPRMTD-UHFFFAOYSA-N 0.000 description 1
- LKXADRQJLNYNQL-UHFFFAOYSA-N 2h-chromen-3-ol Chemical compound C1=CC=C2OCC(O)=CC2=C1 LKXADRQJLNYNQL-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 229940124538 antidiuretic agent Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 1
- 229960003602 guanethidine Drugs 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UWPCIMKHFDRHAA-UHFFFAOYSA-N n-(2,2-dimethyl-7-nitrochromen-6-yl)acetamide Chemical compound C1=CC(C)(C)OC2=C1C=C(NC(=O)C)C([N+]([O-])=O)=C2 UWPCIMKHFDRHAA-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
-
- 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
- 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
- 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
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE66/80A IE44589B1 (en) | 1976-01-27 | 1977-01-26 | Trans-4-heterocyclyl-3,4-dihydro-2h-benzo(b)pyran-3-ol derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3024/76A GB1548221A (en) | 1976-01-27 | 1976-01-27 | Trans-4-heterocycyl-3,4-dihydro-2h-benzo pyran-3-ol esters |
| GB1423976 | 1976-04-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE44588L IE44588L (en) | 1977-07-27 |
| IE44588B1 true IE44588B1 (en) | 1982-01-27 |
Family
ID=26237940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE161/77A IE44588B1 (en) | 1976-01-27 | 1977-01-26 | Trans-4-heterocyclyl-3,4-dihidro-2h-benzo(b)pyran-3-ol esters |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5291866A (enrdf_load_stackoverflow) |
| AU (1) | AU505768B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2702092A1 (enrdf_load_stackoverflow) |
| DK (1) | DK31977A (enrdf_load_stackoverflow) |
| ES (1) | ES454888A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2339606A1 (enrdf_load_stackoverflow) |
| IE (1) | IE44588B1 (enrdf_load_stackoverflow) |
| NL (1) | NL7700819A (enrdf_load_stackoverflow) |
| SE (1) | SE7700824L (enrdf_load_stackoverflow) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA795275B (en) * | 1978-10-04 | 1980-09-24 | Beecham Group Ltd | Chromanol derivatives a process for their preparation and their use in pharmaceutical compositions |
| ZM7682A1 (en) * | 1981-09-25 | 1983-05-23 | Beecham Group Plc | Active compounds |
| GB8313679D0 (en) * | 1983-05-18 | 1983-06-22 | Beecham Group Plc | Active compounds |
| GB8419516D0 (en) * | 1984-07-31 | 1984-09-05 | Beecham Group Plc | Treatment |
| GB8625185D0 (en) * | 1986-10-21 | 1986-11-26 | Beecham Group Plc | Active compounds |
| US5352814A (en) * | 1991-08-30 | 1994-10-04 | Nissan Chemical Industries, Ltd. | Asymmetric epoxidation reaction |
| AU7319800A (en) | 1999-09-24 | 2001-04-24 | Nissan Chemical Industries Ltd. | 4-oxybenzopyran derivative |
| WO2001025224A1 (en) | 1999-10-05 | 2001-04-12 | Nissan Chemical Industries, Ltd. | 4-oxybenzopyran derivative |
| KR100869897B1 (ko) | 2001-06-25 | 2008-11-24 | 닛산 가가쿠 고교 가부시키 가이샤 | 부정맥 치료용 치환 벤조피란 유도체 |
-
1977
- 1977-01-07 ES ES454888A patent/ES454888A1/es not_active Expired
- 1977-01-19 DE DE19772702092 patent/DE2702092A1/de not_active Withdrawn
- 1977-01-21 FR FR7701699A patent/FR2339606A1/fr active Granted
- 1977-01-25 AU AU21625/77A patent/AU505768B2/en not_active Expired
- 1977-01-26 JP JP761377A patent/JPS5291866A/ja active Pending
- 1977-01-26 IE IE161/77A patent/IE44588B1/en unknown
- 1977-01-26 DK DK31977A patent/DK31977A/da not_active Application Discontinuation
- 1977-01-26 SE SE7700824A patent/SE7700824L/xx unknown
- 1977-01-27 NL NL7700819A patent/NL7700819A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2702092A1 (de) | 1977-07-28 |
| FR2339606A1 (fr) | 1977-08-26 |
| SE7700824L (sv) | 1977-07-28 |
| NL7700819A (nl) | 1977-07-29 |
| JPS5291866A (en) | 1977-08-02 |
| AU505768B2 (en) | 1979-11-29 |
| AU2162577A (en) | 1978-08-03 |
| FR2339606B1 (enrdf_load_stackoverflow) | 1981-01-16 |
| DK31977A (da) | 1977-07-28 |
| ES454888A1 (es) | 1978-05-01 |
| IE44588L (en) | 1977-07-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK170444B1 (da) | Analogifremgangsmåde til fremstilling af bicycliske aminosyrederivater og deres fysiologisk uskadelige salte | |
| US4725691A (en) | 2-[8-quinolinyl]-sulphinyl-1H-benzimidazole | |
| US4714762A (en) | Antiarteriosclerotic substituted benzimidazol-2-yl-and 3H-imidazo[4,5-b]pyridin-2-yl-phenoxy-alkanoic acids and salts and esters thereof | |
| JPS6354321A (ja) | 血糖降下剤 | |
| BG60428B2 (bg) | Бензимидазоли,метод за получаването им и лекарствени средства, които ги съдържат | |
| EP0262399A2 (en) | Cyclic enol derivatives, production and use thereof | |
| IE51551B1 (en) | Isoquinoline derivatives,process for their preparation and pharmaceutical formulations containing them and their use | |
| KR960012206B1 (ko) | 티아졸리딘-2,4-디온 유도체 및 이의 염, 이의 제조방법 및 이의 용도 | |
| IE44588B1 (en) | Trans-4-heterocyclyl-3,4-dihidro-2h-benzo(b)pyran-3-ol esters | |
| US4134991A (en) | Derivatives of 2-(3-phenyl-2-aminopropionyloxy)-acetic acid | |
| US4977153A (en) | 3-aminopropyloxyphenyl derivatives, pharmaceutical compositions containing them and method for the therapy of diseases | |
| US4760078A (en) | Immunomodulator 1,2-dithiol-3-thione derivative composition, use method and process of producing the same | |
| KR100352899B1 (ko) | 새로운3-페닐설포닐-3,7-디아자바이사이클로[3,3,1]노난-화합물을함유하는약제 | |
| US4173577A (en) | Phenylacetohydroxamic acids | |
| US4092430A (en) | Antiphlogistic phenylacetohydroxamic acid compositions | |
| PL103682B1 (pl) | Sposob wytwarzania nowych pochodnych indazoliloksy-4-propanoloaminy | |
| FR2470767A1 (fr) | Nouveaux iminoacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzymes | |
| JPS60158190A (ja) | ヒダントイン誘導体およびその製法ならびにそれを含有する医薬 | |
| FR2460934A1 (fr) | Derives d'isoquinoleine contenant du soufre, procedes pour leur preparation et compositions pharmaceutiques les contenant | |
| EP0039919B1 (en) | Benzoxazole and benzothiazole derivatives with anti-allergic activity | |
| US4576953A (en) | Quinoline derivatives | |
| CA1110249A (en) | Indolopyrones having antiallergic activity | |
| US4015002A (en) | 1-Aryl-2-oxo-2,4,5,6,7,7a-hexahydro-indoles, salts, pharmaceutical compositions and methods of use | |
| US4755523A (en) | Abietamide derivatives | |
| GB1572920A (en) | Quinoline carboxalic acid esters |