NO851010L - Substituerte benzopyraner, fremgangsmaate til deres fremstilling, samt deres anvendelse i legemidler - Google Patents
Substituerte benzopyraner, fremgangsmaate til deres fremstilling, samt deres anvendelse i legemidlerInfo
- Publication number
- NO851010L NO851010L NO851010A NO851010A NO851010L NO 851010 L NO851010 L NO 851010L NO 851010 A NO851010 A NO 851010A NO 851010 A NO851010 A NO 851010A NO 851010 L NO851010 L NO 851010L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- optionally substituted
- hydrogen
- different
- same
- Prior art date
Links
- 150000001562 benzopyrans Chemical class 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000003814 drug Substances 0.000 title claims description 5
- -1 substituted Chemical class 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical class BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- RUHDMIRVAFTNRL-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-4-carbaldehyde Chemical class C1=CC=C2C(C=O)CCOC2=C1 RUHDMIRVAFTNRL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical group C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000005237 alkyleneamino group Chemical group 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 39
- 235000019198 oils Nutrition 0.000 description 39
- 238000009835 boiling Methods 0.000 description 15
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
- 150000008371 chromenes Chemical class 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XGFJPMBRXFFNAH-UHFFFAOYSA-N 3,4-dihydro-2h-chromen-4-ylmethanamine Chemical class C1=CC=C2C(CN)CCOC2=C1 XGFJPMBRXFFNAH-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 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
- 230000002490 cerebral effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- IRRAFVVDAMRVGP-UHFFFAOYSA-N (2,2,6-trimethyl-3,4-dihydrochromen-4-yl)methanamine Chemical compound O1C(C)(C)CC(CN)C2=CC(C)=CC=C21 IRRAFVVDAMRVGP-UHFFFAOYSA-N 0.000 description 1
- PXXAXOLBHLGSGU-UHFFFAOYSA-N (2,2,6-trimethylchromen-4-yl)methanamine Chemical compound O1C(C)(C)C=C(CN)C2=CC(C)=CC=C21 PXXAXOLBHLGSGU-UHFFFAOYSA-N 0.000 description 1
- YHOIIZBVPNGFJW-UHFFFAOYSA-N (2,2-diethyl-3,4-dihydrochromen-4-yl)methanamine Chemical compound C1=CC=C2OC(CC)(CC)CC(CN)C2=C1 YHOIIZBVPNGFJW-UHFFFAOYSA-N 0.000 description 1
- ORRQFMPBQMLTNI-UHFFFAOYSA-N (2,2-diethylchromen-4-yl)methanamine Chemical compound C1=CC=C2C(CN)=CC(CC)(CC)OC2=C1 ORRQFMPBQMLTNI-UHFFFAOYSA-N 0.000 description 1
- OCEMUYNEIYSNHJ-UHFFFAOYSA-N (2,2-dimethylchromen-4-yl)methanamine Chemical compound C1=CC=C2C(CN)=CC(C)(C)OC2=C1 OCEMUYNEIYSNHJ-UHFFFAOYSA-N 0.000 description 1
- YPHZGZOLOXIUCK-UHFFFAOYSA-N (2-cyclohexyl-3,4-dihydro-2h-chromen-4-yl)methanamine Chemical compound O1C2=CC=CC=C2C(CN)CC1C1CCCCC1 YPHZGZOLOXIUCK-UHFFFAOYSA-N 0.000 description 1
- OGQIHWGQEQWHLS-UHFFFAOYSA-N (2-cyclopentyl-3,4-dihydro-2h-chromen-4-yl)methanamine Chemical compound O1C2=CC=CC=C2C(CN)CC1C1CCCC1 OGQIHWGQEQWHLS-UHFFFAOYSA-N 0.000 description 1
- VEUVXPBAPNUVKD-UHFFFAOYSA-N (2-hexyl-2h-chromen-4-yl)methanamine Chemical compound C1=CC=C2C(CN)=CC(CCCCCC)OC2=C1 VEUVXPBAPNUVKD-UHFFFAOYSA-N 0.000 description 1
- ZBJXOVKTXXFHEB-UHFFFAOYSA-N (2-hexyl-3,4-dihydro-2h-chromen-4-yl)methanamine Chemical compound C1=CC=C2OC(CCCCCC)CC(CN)C2=C1 ZBJXOVKTXXFHEB-UHFFFAOYSA-N 0.000 description 1
- GMPKOEUYHKTDSE-UHFFFAOYSA-N (2-methyl-2-propyl-3,4-dihydrochromen-4-yl)methanamine Chemical compound C1=CC=C2OC(CCC)(C)CC(CN)C2=C1 GMPKOEUYHKTDSE-UHFFFAOYSA-N 0.000 description 1
- JFJJRMPVPLAVND-UHFFFAOYSA-N (2-methyl-2-propylchromen-4-yl)methanamine Chemical compound C1=CC=C2C(CN)=CC(CCC)(C)OC2=C1 JFJJRMPVPLAVND-UHFFFAOYSA-N 0.000 description 1
- SCFMLZHFRHCAJC-UHFFFAOYSA-N (2-methyl-2h-chromen-4-yl)methanamine Chemical compound C1=CC=C2C(CN)=CC(C)OC2=C1 SCFMLZHFRHCAJC-UHFFFAOYSA-N 0.000 description 1
- RVYZAVFGTQYXHX-UHFFFAOYSA-N (2-methyl-3,4-dihydro-2h-chromen-4-yl)methanamine Chemical compound C1=CC=C2OC(C)CC(CN)C2=C1 RVYZAVFGTQYXHX-UHFFFAOYSA-N 0.000 description 1
- GCMBSGMPDRGOBS-UHFFFAOYSA-N (2-propan-2-yl-2h-chromen-4-yl)methanamine Chemical compound C1=CC=C2C(CN)=CC(C(C)C)OC2=C1 GCMBSGMPDRGOBS-UHFFFAOYSA-N 0.000 description 1
- LYZLBBSKLSJGSM-UHFFFAOYSA-N (2-propan-2-yl-3,4-dihydro-2h-chromen-4-yl)methanamine Chemical compound C1=CC=C2OC(C(C)C)CC(CN)C2=C1 LYZLBBSKLSJGSM-UHFFFAOYSA-N 0.000 description 1
- NOVUQIKDBKHNTP-UHFFFAOYSA-N (2-propyl-2h-chromen-4-yl)methanamine Chemical compound C1=CC=C2C(CN)=CC(CCC)OC2=C1 NOVUQIKDBKHNTP-UHFFFAOYSA-N 0.000 description 1
- VXFOWOFGTJLIGZ-UHFFFAOYSA-N (2-propyl-3,4-dihydro-2h-chromen-4-yl)methanamine Chemical compound C1=CC=C2OC(CCC)CC(CN)C2=C1 VXFOWOFGTJLIGZ-UHFFFAOYSA-N 0.000 description 1
- XSAABWKOIOJUDU-UHFFFAOYSA-N (7-methoxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)methanamine Chemical compound NCC1CC(C)(C)OC2=CC(OC)=CC=C21 XSAABWKOIOJUDU-UHFFFAOYSA-N 0.000 description 1
- KKQFPKXKPNUSMU-UHFFFAOYSA-N (7-methoxy-2,2-dimethylchromen-4-yl)methanamine Chemical compound NCC1=CC(C)(C)OC2=CC(OC)=CC=C21 KKQFPKXKPNUSMU-UHFFFAOYSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- BTPOVNGEGQQHIV-UHFFFAOYSA-N 1-(4-nitrophenoxy)propan-2-one Chemical compound CC(=O)COC1=CC=C([N+]([O-])=O)C=C1 BTPOVNGEGQQHIV-UHFFFAOYSA-N 0.000 description 1
- SAXKWTPDZMBKSQ-UHFFFAOYSA-N 2,2'-dimethylchromene Natural products C1=CC=C2C=CC(C)(C)OC2=C1 SAXKWTPDZMBKSQ-UHFFFAOYSA-N 0.000 description 1
- RBBMAXDAWPFINF-UHFFFAOYSA-N 2,2,6-trimethyl-3,4-dihydrochromene-4-carbaldehyde Chemical compound O1C(C)(C)CC(C=O)C2=CC(C)=CC=C21 RBBMAXDAWPFINF-UHFFFAOYSA-N 0.000 description 1
- URJRRHZIOCZLOM-UHFFFAOYSA-N 2,2-diethyl-3,4-dihydrochromene-4-carbaldehyde Chemical compound C1=CC=C2OC(CC)(CC)CC(C=O)C2=C1 URJRRHZIOCZLOM-UHFFFAOYSA-N 0.000 description 1
- DWJFKQLDRJLDNR-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydrochromene-4-carbaldehyde Chemical compound C1=CC=C2OC(C)(C)CC(C=O)C2=C1 DWJFKQLDRJLDNR-UHFFFAOYSA-N 0.000 description 1
- DIWPYYYHHMFZNF-UHFFFAOYSA-N 2-cyclohexyl-3,4-dihydro-2h-chromene-4-carbaldehyde Chemical compound O1C2=CC=CC=C2C(C=O)CC1C1CCCCC1 DIWPYYYHHMFZNF-UHFFFAOYSA-N 0.000 description 1
- FLRDTDRZPBLKAE-UHFFFAOYSA-N 2-cyclopentyl-3,4-dihydro-2h-chromene-4-carbaldehyde Chemical compound O1C2=CC=CC=C2C(C=O)CC1C1CCCC1 FLRDTDRZPBLKAE-UHFFFAOYSA-N 0.000 description 1
- XGXOHGWYYASPIV-UHFFFAOYSA-N 2-hexyl-3,4-dihydro-2h-chromene-4-carbaldehyde Chemical compound C1=CC=C2OC(CCCCCC)CC(C=O)C2=C1 XGXOHGWYYASPIV-UHFFFAOYSA-N 0.000 description 1
- NXRHFIXNAVXMQI-UHFFFAOYSA-N 2-methyl-2-propyl-3,4-dihydrochromene-4-carbaldehyde Chemical compound C1=CC=C2OC(CCC)(C)CC(C=O)C2=C1 NXRHFIXNAVXMQI-UHFFFAOYSA-N 0.000 description 1
- ODDZAQRLXVRLDV-UHFFFAOYSA-N 2-methyl-3,4-dihydro-2h-chromene-4-carbaldehyde Chemical compound C1=CC=C2OC(C)CC(C=O)C2=C1 ODDZAQRLXVRLDV-UHFFFAOYSA-N 0.000 description 1
- WNJTUEVZVOKDSC-UHFFFAOYSA-N 2-propan-2-yl-3,4-dihydro-2h-chromene-4-carbaldehyde Chemical compound C1=CC=C2OC(C(C)C)CC(C=O)C2=C1 WNJTUEVZVOKDSC-UHFFFAOYSA-N 0.000 description 1
- RSBDHOPHGAJHIT-UHFFFAOYSA-N 2-propyl-3,4-dihydro-2h-chromene-4-carbaldehyde Chemical compound C1=CC=C2OC(CCC)CC(C=O)C2=C1 RSBDHOPHGAJHIT-UHFFFAOYSA-N 0.000 description 1
- 150000000463 2H-chromenes Chemical class 0.000 description 1
- NSBMJUZLRIEOGZ-UHFFFAOYSA-N 2h-chromen-2-ylmethanamine Chemical class C1=CC=C2C=CC(CN)OC2=C1 NSBMJUZLRIEOGZ-UHFFFAOYSA-N 0.000 description 1
- WRQGQTBQEWMFLP-UHFFFAOYSA-N 2h-chromen-4-ylmethanamine Chemical compound C1=CC=C2C(CN)=CCOC2=C1 WRQGQTBQEWMFLP-UHFFFAOYSA-N 0.000 description 1
- PIGDIAQNJLGVNC-UHFFFAOYSA-N 2h-chromene-4-carbonitrile Chemical class C1=CC=C2C(C#N)=CCOC2=C1 PIGDIAQNJLGVNC-UHFFFAOYSA-N 0.000 description 1
- ABAPCDWXFHBYPE-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-4-carbonitrile Chemical class C1=CC=C2C(C#N)CCOC2=C1 ABAPCDWXFHBYPE-UHFFFAOYSA-N 0.000 description 1
- QRNTZQJFCAXEEJ-UHFFFAOYSA-N 4-(2-nitrophenyl)butan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1[N+]([O-])=O QRNTZQJFCAXEEJ-UHFFFAOYSA-N 0.000 description 1
- DRTMOUXEYZBQFJ-UHFFFAOYSA-N 4-(3-chloro-5-nitrophenyl)butan-2-amine Chemical compound CC(N)CCC1=CC(Cl)=CC([N+]([O-])=O)=C1 DRTMOUXEYZBQFJ-UHFFFAOYSA-N 0.000 description 1
- FBDITDJHSSHFSO-UHFFFAOYSA-N 4-(bromomethyl)-2,2,6-trimethylchromene Chemical compound O1C(C)(C)C=C(CBr)C2=CC(C)=CC=C21 FBDITDJHSSHFSO-UHFFFAOYSA-N 0.000 description 1
- TVTLELPOCKXEDQ-UHFFFAOYSA-N 4-(bromomethyl)-2,2-dimethylchromene Chemical compound C1=CC=C2C(CBr)=CC(C)(C)OC2=C1 TVTLELPOCKXEDQ-UHFFFAOYSA-N 0.000 description 1
- FMDFEFTWQYNFSZ-UHFFFAOYSA-N 4-(bromomethyl)-2-cyclohexyl-2h-chromene Chemical compound O1C2=CC=CC=C2C(CBr)=CC1C1CCCCC1 FMDFEFTWQYNFSZ-UHFFFAOYSA-N 0.000 description 1
- IGEOUCLBMJSVLS-UHFFFAOYSA-N 4-(bromomethyl)-2-hexyl-2h-chromene Chemical compound C1=CC=C2C(CBr)=CC(CCCCCC)OC2=C1 IGEOUCLBMJSVLS-UHFFFAOYSA-N 0.000 description 1
- GCHDFCVRBMVOGA-UHFFFAOYSA-N 4-(bromomethyl)-2-methyl-2h-chromene Chemical compound C1=CC=C2C(CBr)=CC(C)OC2=C1 GCHDFCVRBMVOGA-UHFFFAOYSA-N 0.000 description 1
- SJZBLEJSUWFHHW-UHFFFAOYSA-N 4-(bromomethyl)-6-chloro-2,2-dimethylchromene Chemical compound C1=C(Cl)C=C2C(CBr)=CC(C)(C)OC2=C1 SJZBLEJSUWFHHW-UHFFFAOYSA-N 0.000 description 1
- XANHHWJNNAFIKR-UHFFFAOYSA-N 4-(bromomethyl)-7-methoxy-2,2-dimethylchromene Chemical compound BrCC1=CC(C)(C)OC2=CC(OC)=CC=C21 XANHHWJNNAFIKR-UHFFFAOYSA-N 0.000 description 1
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical class C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
- NRYJUMHZZUZTOP-UHFFFAOYSA-N 6-(3-oxobutyl)-1,3-benzodioxole-4-sulfonamide Chemical compound NS(=O)(=O)C1=CC(CCC(=O)C)=CC2=C1OCO2 NRYJUMHZZUZTOP-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- SKALBBIHLVNCGO-UHFFFAOYSA-N 6-chloro-2,2-dimethyl-3,4-dihydrochromene-4-carbaldehyde Chemical compound ClC1=CC=C2OC(C)(C)CC(C=O)C2=C1 SKALBBIHLVNCGO-UHFFFAOYSA-N 0.000 description 1
- DNOVWBKKPOCIBZ-UHFFFAOYSA-N 7-methoxy-2,2-dimethyl-3,4-dihydrochromene-4-carbaldehyde Chemical compound O=CC1CC(C)(C)OC2=CC(OC)=CC=C21 DNOVWBKKPOCIBZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- UHZGJOXCJNDNDU-UHFFFAOYSA-N C1=CC2CCCOC2=C2C=CC=C21 Chemical compound C1=CC2CCCOC2=C2C=CC=C21 UHZGJOXCJNDNDU-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical class ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 1
- KZFWBKPNDQIRRP-UHFFFAOYSA-M NCO[Cr](O)(=O)=O Chemical class NCO[Cr](O)(=O)=O KZFWBKPNDQIRRP-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000006734 Wohl-Ziegler bromination reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- GPTJTTCOVDDHER-UHFFFAOYSA-N cyclononane Chemical compound C1CCCCCCCC1 GPTJTTCOVDDHER-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BUFBLEBIJQZIRM-UHFFFAOYSA-N n-[3-(3-aminobutyl)phenyl]acetamide Chemical compound CC(N)CCC1=CC=CC(NC(C)=O)=C1 BUFBLEBIJQZIRM-UHFFFAOYSA-N 0.000 description 1
- ZQBRPUQNVGCUEJ-UHFFFAOYSA-N n-[3-methyl-5-(3-oxobutyl)phenyl]methanesulfonamide Chemical compound CC(=O)CCC1=CC(C)=CC(NS(C)(=O)=O)=C1 ZQBRPUQNVGCUEJ-UHFFFAOYSA-N 0.000 description 1
- SYXRXHRRHUDSPA-UHFFFAOYSA-N n-[5-(3-aminobutyl)-2,3-dimethoxyphenyl]methanesulfonamide Chemical compound COC1=CC(CCC(C)N)=CC(NS(C)(=O)=O)=C1OC SYXRXHRRHUDSPA-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003235 vasospasmolytic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Glass Compositions (AREA)
- Surface Acoustic Wave Elements And Circuit Networks Thereof (AREA)
- Dental Preparations (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843411993 DE3411993A1 (de) | 1984-03-31 | 1984-03-31 | Substituierte benzopyrane, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO851010L true NO851010L (no) | 1985-10-01 |
Family
ID=6232185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO851010A NO851010L (no) | 1984-03-31 | 1985-03-14 | Substituerte benzopyraner, fremgangsmaate til deres fremstilling, samt deres anvendelse i legemidler |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4659737A (fi) |
| EP (1) | EP0157267B1 (fi) |
| JP (1) | JPS60224685A (fi) |
| KR (1) | KR850006194A (fi) |
| AT (1) | ATE38836T1 (fi) |
| AU (1) | AU4059485A (fi) |
| DE (2) | DE3411993A1 (fi) |
| DK (1) | DK144685A (fi) |
| ES (2) | ES8703448A1 (fi) |
| FI (1) | FI851261L (fi) |
| GR (1) | GR850799B (fi) |
| HU (1) | HUT38097A (fi) |
| IL (1) | IL74745A0 (fi) |
| NO (1) | NO851010L (fi) |
| NZ (1) | NZ211617A (fi) |
| PT (1) | PT80191B (fi) |
| ZA (1) | ZA852391B (fi) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4918092A (en) * | 1983-12-21 | 1990-04-17 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
| ES2044970T3 (es) * | 1986-06-26 | 1994-01-16 | Ciba Geigy Ag | Procedimiento para la obtencion de compuestos hidrogenados del acido 1-benzooxacicloalquil-piridincarboxilico. |
| FR2618437B1 (fr) * | 1987-07-23 | 1989-11-17 | Rhone Poulenc Sante | Nouveaux derives du benzopyranne, leur preparation et les medicaments qui les contiennent |
| DE3737195A1 (de) * | 1987-11-03 | 1989-05-18 | Bayer Ag | Chromanderivate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| US5140039A (en) * | 1988-01-15 | 1992-08-18 | Abbott Laboratories | Aminomethyl-thiochroman compounds |
| US5185364A (en) * | 1988-01-15 | 1993-02-09 | Abbott Laboratories | Aminomethyl-chroman and -thiochroman compounds |
| EP0325964A1 (en) * | 1988-01-15 | 1989-08-02 | Abbott Laboratories | Aminomethyl-chroman and -thiochroman compounds |
| DE3901814A1 (de) * | 1988-07-28 | 1990-02-01 | Bayer Ag | Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga |
| US5264458A (en) * | 1989-11-02 | 1993-11-23 | Bayer Aktiengesellschaft | Antithrombotic iso- and heterocyclic phenylsulphonamides |
| WO1992008712A1 (en) * | 1990-11-08 | 1992-05-29 | Yamanouchi Pharmaceutical Co., Ltd. | Flavane derivative or salt thereof and novel production process |
| US5837702A (en) * | 1993-10-07 | 1998-11-17 | Bristol-Myers Squibb Co. | 4-arylamino-benzopyran and related compounds |
| 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 |
| 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 |
| GB9801392D0 (en) * | 1998-01-22 | 1998-03-18 | Smithkline Beecham Plc | Novel compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH648030A5 (de) * | 1980-12-15 | 1985-02-28 | Sandoz Ag | Benzopyran-allylaminderivate, verfahren zu ihrer herstellung und ihre verwendung. |
| DE3300004A1 (de) * | 1983-01-03 | 1984-07-12 | Bayer Ag, 5090 Leverkusen | Substituierte 4-aminomethylenchromane bzw. -chromene, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
-
1984
- 1984-03-31 DE DE19843411993 patent/DE3411993A1/de not_active Withdrawn
-
1985
- 1985-03-14 NO NO851010A patent/NO851010L/no unknown
- 1985-03-18 DE DE8585103092T patent/DE3566404D1/de not_active Expired
- 1985-03-18 AT AT85103092T patent/ATE38836T1/de not_active IP Right Cessation
- 1985-03-18 EP EP85103092A patent/EP0157267B1/de not_active Expired
- 1985-03-25 US US06/715,434 patent/US4659737A/en not_active Expired - Fee Related
- 1985-03-26 ES ES541583A patent/ES8703448A1/es not_active Expired
- 1985-03-28 IL IL74745A patent/IL74745A0/xx unknown
- 1985-03-28 FI FI851261A patent/FI851261L/fi not_active Application Discontinuation
- 1985-03-28 NZ NZ211617A patent/NZ211617A/en unknown
- 1985-03-28 JP JP60062209A patent/JPS60224685A/ja active Pending
- 1985-03-29 DK DK144685A patent/DK144685A/da not_active Application Discontinuation
- 1985-03-29 GR GR850799A patent/GR850799B/el unknown
- 1985-03-29 ZA ZA852391A patent/ZA852391B/xx unknown
- 1985-03-29 PT PT80191A patent/PT80191B/pt not_active IP Right Cessation
- 1985-03-29 HU HU851206A patent/HUT38097A/hu unknown
- 1985-03-30 KR KR1019850002157A patent/KR850006194A/ko not_active Application Discontinuation
- 1985-04-01 AU AU40594/85A patent/AU4059485A/en not_active Abandoned
-
1986
- 1986-07-01 ES ES556864A patent/ES8801912A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU4059485A (en) | 1985-10-03 |
| IL74745A0 (en) | 1985-06-30 |
| JPS60224685A (ja) | 1985-11-09 |
| HUT38097A (en) | 1986-04-28 |
| DE3411993A1 (de) | 1985-10-10 |
| ATE38836T1 (de) | 1988-12-15 |
| PT80191A (en) | 1985-04-01 |
| FI851261A0 (fi) | 1985-03-28 |
| ES8703448A1 (es) | 1987-02-16 |
| EP0157267A2 (de) | 1985-10-09 |
| EP0157267B1 (de) | 1988-11-23 |
| DK144685D0 (da) | 1985-03-29 |
| ZA852391B (en) | 1985-11-27 |
| EP0157267A3 (en) | 1986-09-03 |
| ES8801912A1 (es) | 1987-08-01 |
| ES556864A0 (es) | 1987-08-01 |
| KR850006194A (ko) | 1985-10-02 |
| DK144685A (da) | 1985-10-01 |
| ES541583A0 (es) | 1987-02-16 |
| GR850799B (fi) | 1985-11-25 |
| US4659737A (en) | 1987-04-21 |
| NZ211617A (en) | 1987-10-30 |
| FI851261L (fi) | 1985-10-01 |
| DE3566404D1 (en) | 1988-12-29 |
| PT80191B (en) | 1987-03-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69713294T3 (de) | Tricyclische Verbindungen mit Bindungsaffinität für Melatoninrezeptoren, deren Herstellung und Verwendung | |
| NO851010L (no) | Substituerte benzopyraner, fremgangsmaate til deres fremstilling, samt deres anvendelse i legemidler | |
| DK164557B (da) | Derivater af cis,endo-2-azabicyclo-oe5.3.0aa-decan-3-carboxylsyre samt laegemiddel indeholdende dem | |
| NO834666L (no) | Substituerte 4-aminometylen-kromaner og -kromener, fremgangsmaater for deres fremstilling og deres bruk i medikamenter | |
| JPH04210663A (ja) | 新規フェニルエタノールアミノメチルテトラリン化合物 | |
| DE60316984T2 (de) | Benzoylsulfonamide als antitumor-mittel | |
| JPS63277671A (ja) | ３−アミノ−ジヒドロ−〔１〕−ベンゾピランおよびベンゾチオピラン | |
| JPH03218367A (ja) | ナフチルオキサゾリドン誘導体、その製法及びその合成中間体 | |
| US4420485A (en) | 1'-[3-(1,2-Benzisoxazol-3-yl) proply]spiro[benzofuran-2(3H),3' or 4'-piperidines or 3'-pyrrolidines] | |
| JPH0347270B2 (fi) | ||
| US4647579A (en) | Circulation active novel substituted 4-hydroxy-benzopyrans | |
| WO2000058301A1 (fr) | Derives de n-[2-(4-aminophenyl)ethyl]-2,3-dihydro-1,4-benzodioxine-2-methanamine, leur preparation et leur application en therapeutique | |
| IE911681A1 (en) | 4-Alkylamino-6-(C3-5-hydrocarbyl)thieno/2,3-b/thiopyran-2-¹sulfonamide-7,7-dioxides | |
| US7227023B2 (en) | Quinoline 3-amino chroman derivatives | |
| GB2056435A (en) | Novel Tetrahydropyridine and Piperidine Substituted Benzofuranes and Related Compounds | |
| EP0127143B1 (en) | Novel aryloxycycloalkanolaminoalkylene aryl ketones | |
| NO327549B1 (no) | Benzo[G]kinolinderivater for behandling av glaukom og myopi | |
| US4868315A (en) | Novel aryloxycycloalkanolaminoalkylene aryl ketones | |
| JPS611676A (ja) | ナフトオキサジン類 | |
| US4226860A (en) | Spiroindolones | |
| US3622610A (en) | Sulfonate esters of gallic acid derivatives | |
| WO2021200934A1 (ja) | 抗マラリア薬 | |
| US4792548A (en) | Trans-benzopyran-(4,3-b)-1,4-oxazine derivatives, intermediates and pharmaceutical use | |
| JPH03197463A (ja) | 新規ベンズアゼピン | |
| JPH0570453A (ja) | アミノメチルイソクロマン誘導体およびその製造方法 |