IE41539B1 - Chroman derivatives - Google Patents
Chroman derivativesInfo
- Publication number
- IE41539B1 IE41539B1 IE1039/75A IE103975A IE41539B1 IE 41539 B1 IE41539 B1 IE 41539B1 IE 1039/75 A IE1039/75 A IE 1039/75A IE 103975 A IE103975 A IE 103975A IE 41539 B1 IE41539 B1 IE 41539B1
- Authority
- IE
- Ireland
- Prior art keywords
- dihydro
- trans
- dimethyl
- pyran
- pharmaceutically acceptable
- Prior art date
Links
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 31
- -1 C 2-6 alkenoxyl Chemical group 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 2
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 2
- HCTZGQKGNBAGKX-CABCVRRESA-N (3s,4r)-2,2-dimethyl-6-nitro-4-piperidin-1-yl-3,4-dihydrochromen-3-ol Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)[N+]([O-])=O)CCCCC1 HCTZGQKGNBAGKX-CABCVRRESA-N 0.000 claims 1
- KVEHOVISRJZEML-KGLIPLIRSA-N (3s,4r)-2,2-dimethyl-6-nitro-4-pyrrolidin-1-yl-3,4-dihydrochromen-3-ol Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)[N+]([O-])=O)CCCC1 KVEHOVISRJZEML-KGLIPLIRSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 7
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 3
- 239000002220 antihypertensive agent Substances 0.000 abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract description 3
- 239000002934 diuretic Substances 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 125000004755 (C2-C7) acylamino group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 101150009274 nhr-1 gene Proteins 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 229960004132 diethyl ether Drugs 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 150000002924 oxiranes Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 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 2
- WXLPKTIAUMCNDX-UHFFFAOYSA-N 2h-pyran-3-ol Chemical compound OC1=CC=COC1 WXLPKTIAUMCNDX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- QDAOKPLENAXFPO-OLZOCXBDSA-N (3s,4r)-2,2-dimethyl-6-nitro-4-(propan-2-ylamino)-3,4-dihydrochromen-3-ol Chemical compound C1=C([N+]([O-])=O)C=C2[C@@H](NC(C)C)[C@H](O)C(C)(C)OC2=C1 QDAOKPLENAXFPO-OLZOCXBDSA-N 0.000 description 1
- JVPRWKWUBCZNJO-VXNVDRBHSA-N (3s,4r)-4-amino-3,4-dihydro-2h-chromen-3-ol Chemical class C1=CC=C2[C@@H](N)[C@H](O)COC2=C1 JVPRWKWUBCZNJO-VXNVDRBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KUVSTBAMMGGNND-UHFFFAOYSA-N 1-(2-methylbut-3-yn-2-yloxy)-4-nitrobenzene Chemical compound C#CC(C)(C)OC1=CC=C([N+]([O-])=O)C=C1 KUVSTBAMMGGNND-UHFFFAOYSA-N 0.000 description 1
- SQUJYDFTMPTTLT-UHFFFAOYSA-N 1-prop-2-ynoxynaphthalene Chemical compound C1=CC=C2C(OCC#C)=CC=CC2=C1 SQUJYDFTMPTTLT-UHFFFAOYSA-N 0.000 description 1
- SEVMPADXRULOAW-UHFFFAOYSA-N 2,2-diethylchromene Chemical compound C1=CC=C2C=CC(CC)(CC)OC2=C1 SEVMPADXRULOAW-UHFFFAOYSA-N 0.000 description 1
- MITIYLBEZOKYLX-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromene Chemical compound C1=CC=C2OC(C)(C)CCC2=C1 MITIYLBEZOKYLX-UHFFFAOYSA-N 0.000 description 1
- LFNQCFYCOQFZFJ-UHFFFAOYSA-N 2,2-dimethylbenzo[h]chromene Chemical compound C1=CC2=CC=CC=C2C2=C1C=CC(C)(C)O2 LFNQCFYCOQFZFJ-UHFFFAOYSA-N 0.000 description 1
- VCDAWCBLCCVSKE-UHFFFAOYSA-N 2h-benzo[h]chromene Chemical compound C1=CC2=CC=CC=C2C2=C1C=CCO2 VCDAWCBLCCVSKE-UHFFFAOYSA-N 0.000 description 1
- QSILYWCNPOLKPN-UHFFFAOYSA-N 3-chloro-3-methylbut-1-yne Chemical compound CC(C)(Cl)C#C QSILYWCNPOLKPN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IZOPMCHRMBWYTD-UHFFFAOYSA-N Cl.O1CC(=CC=C1)O Chemical compound Cl.O1CC(=CC=C1)O IZOPMCHRMBWYTD-UHFFFAOYSA-N 0.000 description 1
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 241000400611 Eucalyptus deanei Species 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 1
- UGUUDTWORXNLAK-UHFFFAOYSA-N azidoalcohol Chemical compound ON=[N+]=[N-] UGUUDTWORXNLAK-UHFFFAOYSA-N 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SPJCUZNWAQZUNI-UHFFFAOYSA-N n-(2,2-dimethylchromen-6-yl)acetamide Chemical compound O1C(C)(C)C=CC2=CC(NC(=O)C)=CC=C21 SPJCUZNWAQZUNI-UHFFFAOYSA-N 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- 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
- A61P9/12—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
- 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
-
- 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
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24348/74A GB1495526A (en) | 1974-05-31 | 1974-05-31 | Chroman derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41539L IE41539L (en) | 1975-11-30 |
| IE41539B1 true IE41539B1 (en) | 1980-01-30 |
Family
ID=10210307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1039/75A IE41539B1 (en) | 1974-05-31 | 1975-05-09 | Chroman derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4048317A (en, 2012) |
| JP (2) | JPS6044308B2 (en, 2012) |
| BE (1) | BE829611A (en, 2012) |
| CA (1) | CA1072090A (en, 2012) |
| DE (1) | DE2523281A1 (en, 2012) |
| DK (1) | DK244875A (en, 2012) |
| ES (1) | ES438072A1 (en, 2012) |
| FR (1) | FR2272659B1 (en, 2012) |
| GB (1) | GB1495526A (en, 2012) |
| HK (1) | HK20781A (en, 2012) |
| IE (1) | IE41539B1 (en, 2012) |
| KE (1) | KE3124A (en, 2012) |
| MY (1) | MY8100356A (en, 2012) |
| NL (1) | NL7506421A (en, 2012) |
| ZA (1) | ZA753076B (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4062870A (en) * | 1974-05-31 | 1977-12-13 | Beecham Group Limited | Chroman derivatives |
| US4542150A (en) * | 1975-09-17 | 1985-09-17 | Cornell Research Foundation, Inc. | Anti-juvenile hormones |
| GB1511187A (en) * | 1976-04-02 | 1978-05-17 | Beecham Group Ltd | Chromans |
| US4391815A (en) * | 1976-04-02 | 1983-07-05 | Beecham Group Limited | Cyanobenzano[b]pyrans |
| NZ183551A (en) * | 1976-04-02 | 1978-09-20 | Beecham Group Ltd | Aminochromanols and pharmaceutical compositions containingthem |
| US4203895A (en) * | 1978-04-14 | 1980-05-20 | Warner-Lambert Company | Process for the preparation of cis-(±)-3,4-dihydro-N,N,2-trimethyl-2H-1-benzopyran-3-amine and intermediates produced thereby |
| DE2965739D1 (en) * | 1978-10-04 | 1983-07-28 | Beecham Group Plc | Chromanol derivatives, a process for their preparation and pharmaceutical compositions comprising them |
| EP0028064B1 (en) * | 1979-09-28 | 1983-07-20 | Beecham Group Plc | Chromanol derivatives, a process for their preparation and a pharmaceutical composition comprising them |
| DE3064285D1 (en) * | 1979-09-28 | 1983-08-25 | Beecham Group Plc | Chromanol derivatives, a process for their preparation and a pharmaceutical composition comprising them |
| GB2064514B (en) * | 1979-10-29 | 1984-01-18 | Maruko Pharmaceutical Co | Flavan compounds and acid addition salts thereof and pharmaceutical compositions thereof |
| EP0033612B1 (en) | 1980-02-02 | 1984-04-11 | Beecham Group Plc | Pyrano derivatives, a process for their preparation and antihypertensive compositions containing them |
| EP0033613A1 (en) * | 1980-02-02 | 1981-08-12 | Beecham Group Plc | Chromanol derivatives, a process for their preparation and compositions containing them |
| EP0046652B1 (en) * | 1980-08-21 | 1985-05-22 | Beecham Group Plc | Chromanol derivatives, their production and pharmaceutical compositions containing them |
| ZM7682A1 (en) * | 1981-09-25 | 1983-05-23 | Beecham Group Plc | Active compounds |
| DE3274350D1 (en) * | 1981-09-25 | 1987-01-08 | Beecham Group Plc | Pharmaceutically active benzopyran compounds |
| DE3364145D1 (de) * | 1982-04-08 | 1986-07-24 | Beecham Group Plc | Antihypertensive benzopyranols |
| DE3368057D1 (en) * | 1982-05-21 | 1987-01-15 | Beecham Group Plc | Pharmaceutically active aminobenzopyrans |
| JPS59110690A (ja) * | 1982-12-16 | 1984-06-26 | Dai Ichi Seiyaku Co Ltd | ベンゾピラン誘導体 |
| DE3479726D1 (de) * | 1983-05-18 | 1989-10-19 | Beecham Group Plc | Benzopyran derivatives. |
| CA1308108C (en) * | 1987-10-27 | 1992-09-29 | Dominick A. Quagliato | Antihypertensive benzopyran derivatives |
| FR2637896B1 (fr) * | 1988-10-17 | 1990-11-30 | Adir | Nouveaux derives de l'amino chromanol, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| FR2639349B1 (fr) * | 1988-11-23 | 1991-02-22 | Sanofi Sa | Nouveaux derives du chromane actifs sur le systeme nerveux central, leur procede de preparation et les compositions pharmaceutiques en contenant |
| US5239090A (en) * | 1989-02-01 | 1993-08-24 | Beecham Group P.L.C. | Certain optically active 3,4-dihydrobenzopyran-4-ols which are intermediates |
| GB8902118D0 (en) * | 1989-02-01 | 1989-03-22 | Beecham Group Plc | Chemical process |
| GB8924373D0 (en) * | 1989-10-30 | 1989-12-20 | Beecham Group Plc | Novel compounds |
| WO1991012005A1 (en) * | 1990-02-06 | 1991-08-22 | Pfizer Inc. | Neuroprotective 3-piperidino-4-hydroxychroman derivatives and analogs |
| US5436255A (en) * | 1992-07-23 | 1995-07-25 | Pfizer Inc. | Method of treating diseases susceptable to treatment by blocking NMDA-receptors |
| WO1995020587A1 (en) * | 1994-01-31 | 1995-08-03 | Pfizer Inc. | Neuroprotective chroman compounds |
| WO1997023209A1 (fr) * | 1995-12-25 | 1997-07-03 | Nissan Chemical Industries, Ltd. | Agent therapeutique contre l'insuffisance cardiaque |
| CZ24499A3 (cs) | 1996-07-26 | 1999-05-12 | Nissan Chemical Industries, Ltd. | Derivát chromanu a farmaceutický prostředek, který ho obsahuje |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518273A (en) * | 1966-08-03 | 1970-06-30 | Warner Lambert Pharmaceutical | Benzopyranquinolinol derivatives and process for their production |
| US3704323A (en) * | 1969-12-23 | 1972-11-28 | Squibb & Sons Inc | Indane derivatives |
| US3743659A (en) * | 1971-08-25 | 1973-07-03 | Riker Laboratories Inc | Substituted isochromans and processes therefor |
-
1974
- 1974-05-31 GB GB24348/74A patent/GB1495526A/en not_active Expired
-
1975
- 1975-05-09 IE IE1039/75A patent/IE41539B1/en unknown
- 1975-05-13 ZA ZA00753076A patent/ZA753076B/xx unknown
- 1975-05-14 US US05/577,614 patent/US4048317A/en not_active Expired - Lifetime
- 1975-05-26 DE DE19752523281 patent/DE2523281A1/de not_active Withdrawn
- 1975-05-28 FR FR7516620A patent/FR2272659B1/fr not_active Expired
- 1975-05-28 BE BE156814A patent/BE829611A/xx not_active IP Right Cessation
- 1975-05-30 JP JP50065185A patent/JPS6044308B2/ja not_active Expired
- 1975-05-30 ES ES438072A patent/ES438072A1/es not_active Expired
- 1975-05-30 CA CA228,104A patent/CA1072090A/en not_active Expired
- 1975-05-30 DK DK244875A patent/DK244875A/da unknown
- 1975-05-30 NL NL7506421A patent/NL7506421A/xx active Search and Examination
-
1981
- 1981-04-06 KE KE3124A patent/KE3124A/xx unknown
- 1981-05-14 HK HK207/81A patent/HK20781A/xx unknown
- 1981-12-30 MY MY356/81A patent/MY8100356A/xx unknown
-
1985
- 1985-04-11 JP JP60077531A patent/JPS60231681A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2272659B1 (en, 2012) | 1980-02-08 |
| US4048317A (en) | 1977-09-13 |
| HK20781A (en) | 1981-05-22 |
| AU8169375A (en) | 1976-12-02 |
| JPS60231681A (ja) | 1985-11-18 |
| DE2523281A1 (de) | 1975-12-11 |
| DK244875A (da) | 1975-12-01 |
| GB1495526A (en) | 1977-12-21 |
| MY8100356A (en) | 1981-12-31 |
| BE829611A (fr) | 1975-11-28 |
| JPS6160077B2 (en, 2012) | 1986-12-19 |
| ES438072A1 (es) | 1977-01-16 |
| ZA753076B (en) | 1976-05-26 |
| IE41539L (en) | 1975-11-30 |
| KE3124A (en) | 1981-05-15 |
| CA1072090A (en) | 1980-02-19 |
| NL7506421A (nl) | 1975-12-02 |
| JPS6044308B2 (ja) | 1985-10-02 |
| JPS511477A (en, 2012) | 1976-01-08 |
| FR2272659A1 (en, 2012) | 1975-12-26 |
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