NO781556L - Benzimidazol-derivater. - Google Patents
Benzimidazol-derivater.Info
- Publication number
- NO781556L NO781556L NO781556A NO781556A NO781556L NO 781556 L NO781556 L NO 781556L NO 781556 A NO781556 A NO 781556A NO 781556 A NO781556 A NO 781556A NO 781556 L NO781556 L NO 781556L
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- hydrogen atom
- benzimidazolinone
- formula
- alkyl group
- Prior art date
Links
- 150000001556 benzimidazoles Chemical class 0.000 title claims description 25
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 69
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 63
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 46
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- -1 4-[3-(cyclohexylamino)-2-hydroxypropoxy]-2-benzimidazolinone Chemical compound 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 10
- 150000002118 epoxides Chemical class 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 8
- 238000011065 in-situ storage Methods 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 150000003573 thiols Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- VQRLGEWFYFOXPA-UHFFFAOYSA-N 4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-1,3-dihydrobenzimidazol-2-one Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1NC(=O)N2 VQRLGEWFYFOXPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- VMIJBKBEEHFLGX-UHFFFAOYSA-N 4-[2-hydroxy-3-(methylamino)propoxy]-1,3-dihydrobenzimidazol-2-one Chemical compound OC(COC1=CC=CC=2NC(NC21)=O)CNC VMIJBKBEEHFLGX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000012546 transfer Methods 0.000 claims description 3
- XWTPLMIQYPKYIO-UHFFFAOYSA-N 4-[3-(dicyclopentylamino)-2-hydroxypropoxy]-1,3-dihydrobenzimidazol-2-one Chemical compound C1(CCCC1)N(CC(COC1=CC=CC=2NC(NC21)=O)O)C2CCCC2 XWTPLMIQYPKYIO-UHFFFAOYSA-N 0.000 claims description 2
- WYIWKNNQOKPTNM-UHFFFAOYSA-N 4-[3-(diethylamino)-2-hydroxypropoxy]-1,3-dihydrobenzimidazol-2-one Chemical compound C(C)N(CC(COC1=CC=CC=2NC(NC21)=O)O)CC WYIWKNNQOKPTNM-UHFFFAOYSA-N 0.000 claims description 2
- RKJCHTLIMAXXBD-UHFFFAOYSA-N 4-[3-(diethylamino)-2-hydroxypropoxy]-1,3-dihydrobenzimidazole-2-thione Chemical compound C(C)N(CC(COC1=CC=CC=2N=C(NC21)S)O)CC RKJCHTLIMAXXBD-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 4
- BXNJPNCQXGADIY-UHFFFAOYSA-N 4-[2-hydroxy-3-(propylamino)propoxy]-1,3-dihydrobenzimidazol-2-one Chemical compound OC(COC1=CC=CC=2NC(NC21)=O)CNCCC BXNJPNCQXGADIY-UHFFFAOYSA-N 0.000 claims 2
- VZXVEQHBGHZBNJ-UHFFFAOYSA-N 4-[3-(dicyclopentylamino)-2-hydroxypropoxy]-7-methyl-1,3-dihydrobenzimidazol-2-one Chemical compound C1(CCCC1)N(CC(COC1=CC=C(C=2NC(NC21)=O)C)O)C2CCCC2 VZXVEQHBGHZBNJ-UHFFFAOYSA-N 0.000 claims 2
- KXEZNOXGNFPRDB-UHFFFAOYSA-N 4-[3-[cyclohexyl(methyl)amino]-2-hydroxypropoxy]-1,3-dihydrobenzimidazol-2-one Chemical compound OC(COC1=CC=CC=2NC(NC21)=O)CN(C)C2CCCCC2 KXEZNOXGNFPRDB-UHFFFAOYSA-N 0.000 claims 2
- GJHQPGOUBCJWJZ-UHFFFAOYSA-N 4-[3-(tert-butylamino)-2-hydroxypropoxy]-7-methyl-1,3-dihydrobenzimidazol-2-one Chemical compound CC1=CC=C(OCC(O)CNC(C)(C)C)C2=C1NC(=O)N2 GJHQPGOUBCJWJZ-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 156
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 229960004592 isopropanol Drugs 0.000 description 42
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 230000008018 melting Effects 0.000 description 26
- 238000002844 melting Methods 0.000 description 26
- 238000004458 analytical method Methods 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- HKHPFDCMZHIIBQ-UHFFFAOYSA-N 2-[(2,3-dinitrophenoxy)methyl]oxirane Chemical compound [O-][N+](=O)C1=CC=CC(OCC2OC2)=C1[N+]([O-])=O HKHPFDCMZHIIBQ-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- CPBGGIHYAYWNDD-UHFFFAOYSA-N 4-hydroxy-1,3-dihydrobenzimidazol-2-one Chemical compound OC1=CC=CC2=C1NC(=O)N2 CPBGGIHYAYWNDD-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 238000011282 treatment Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XQRIIZNTOKFIBU-UHFFFAOYSA-N 2-[(4-methyl-2,3-dinitrophenoxy)methyl]oxirane Chemical compound [O-][N+](=O)C1=C([N+]([O-])=O)C(C)=CC=C1OCC1OC1 XQRIIZNTOKFIBU-UHFFFAOYSA-N 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 4
- RGAFTXCTIKLLTR-UHFFFAOYSA-N 4-methoxy-1,3-dihydrobenzimidazol-2-one Chemical compound COC1=CC=CC2=C1NC(=O)N2 RGAFTXCTIKLLTR-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 4
- 229960002508 pindolol Drugs 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KKXAQCNTKFVOJL-UHFFFAOYSA-N 1-(dicyclopentylamino)-3-(4-methyl-2,3-dinitrophenoxy)propan-2-ol Chemical compound [O-][N+](=O)C1=C([N+]([O-])=O)C(C)=CC=C1OCC(O)CN(C1CCCC1)C1CCCC1 KKXAQCNTKFVOJL-UHFFFAOYSA-N 0.000 description 3
- NDKWDGCTUOOAPF-UHFFFAOYSA-N 2-methoxy-6-nitroaniline Chemical compound COC1=CC=CC([N+]([O-])=O)=C1N NDKWDGCTUOOAPF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 125000006309 butyl amino group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 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
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- OJWGZMNOJJAHTR-UHFFFAOYSA-N 4-[3-(cyclohexylamino)-2-hydroxypropoxy]-1,3-dihydrobenzimidazol-2-one hydrochloride Chemical compound Cl.C1(CCCCC1)NCC(COC1=CC=CC=2NC(NC21)=O)O OJWGZMNOJJAHTR-UHFFFAOYSA-N 0.000 description 2
- VIORRNJSVRGDCJ-UHFFFAOYSA-N 4-[3-(cyclopentylamino)-2-hydroxypropoxy]-7-methyl-1,3-dihydrobenzimidazol-2-one Chemical compound C1(CCCC1)NCC(COC1=CC=C(C=2NC(NC21)=O)C)O VIORRNJSVRGDCJ-UHFFFAOYSA-N 0.000 description 2
- ZONXEHPKQZCPNN-UHFFFAOYSA-N 4-[3-(diethylamino)-2-hydroxypropoxy]-1,3-dihydrobenzimidazol-2-one hydrochloride Chemical compound Cl.C(C)N(CC(COC1=CC=CC=2NC(NC21)=O)O)CC ZONXEHPKQZCPNN-UHFFFAOYSA-N 0.000 description 2
- PULXDWLLHIOXKI-UHFFFAOYSA-N Cl.C(C)N(CC)CC(COC1=CC=CC=2N=C(NC21)S)O Chemical compound Cl.C(C)N(CC)CC(COC1=CC=CC=2N=C(NC21)S)O PULXDWLLHIOXKI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000007963 capsule composition Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- PHQRMKOKTRIKEN-UHFFFAOYSA-N n-cyclopentylcyclopentanamine;hydrochloride Chemical compound Cl.C1CCCC1NC1CCCC1 PHQRMKOKTRIKEN-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-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
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LWNDLCRUZVMGFG-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)NC2=C1 LWNDLCRUZVMGFG-UHFFFAOYSA-N 0.000 description 1
- DERBQHFIKUMUPM-UHFFFAOYSA-N 1-(2,3-diaminophenoxy)-3-(dicyclopentylamino)propan-2-ol Chemical compound NC1=CC=CC(OCC(O)CN(C2CCCC2)C2CCCC2)=C1N DERBQHFIKUMUPM-UHFFFAOYSA-N 0.000 description 1
- JRNIQGKMYQYSGH-UHFFFAOYSA-N 1-(2,3-diaminophenoxy)-3-(diethylamino)propan-2-ol Chemical compound CCN(CC)CC(O)COC1=CC=CC(N)=C1N JRNIQGKMYQYSGH-UHFFFAOYSA-N 0.000 description 1
- RVWRKMLCKHPUBK-UHFFFAOYSA-N 1-(2,3-diaminophenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC(N)=C1N RVWRKMLCKHPUBK-UHFFFAOYSA-N 0.000 description 1
- YGSXLVZEEOBCDJ-UHFFFAOYSA-N 1-(2,3-diaminophenoxy)-3-(propylamino)propan-2-ol Chemical compound CCCNCC(O)COC1=CC=CC(N)=C1N YGSXLVZEEOBCDJ-UHFFFAOYSA-N 0.000 description 1
- HBPKLTJWNQDWFT-UHFFFAOYSA-N 1-(cyclohexylamino)-3-(2,3-diaminophenoxy)propan-2-ol Chemical compound NC1=CC=CC(OCC(O)CNC2CCCCC2)=C1N HBPKLTJWNQDWFT-UHFFFAOYSA-N 0.000 description 1
- XKVZCHHXURMTDB-UHFFFAOYSA-N 1-(dicyclopentylamino)-3-(2,3-dinitrophenoxy)propan-2-ol Chemical compound C1CCCC1N(C1CCCC1)CC(O)COC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O XKVZCHHXURMTDB-UHFFFAOYSA-N 0.000 description 1
- AJLQESNKUTZRAL-UHFFFAOYSA-N 1-(tert-butylamino)-3-(2,3-diamino-4-methylphenoxy)propan-2-ol Chemical compound CC1=CC=C(OCC(O)CNC(C)(C)C)C(N)=C1N AJLQESNKUTZRAL-UHFFFAOYSA-N 0.000 description 1
- DGBMCYDQEPHSRM-UHFFFAOYSA-N 1-[cyclohexyl(methyl)amino]-3-(2,3-diaminophenoxy)propan-2-ol Chemical compound NC1=C(OCC(CN(C)C2CCCCC2)O)C=CC=C1N DGBMCYDQEPHSRM-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical compound NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BFLWXPJTAKXXKT-UHFFFAOYSA-N 3-methoxybenzene-1,2-diamine Chemical compound COC1=CC=CC(N)=C1N BFLWXPJTAKXXKT-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- GXHWSJREEBJWPX-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1,3-dihydrobenzimidazol-2-one Chemical compound C=12NC(=O)NC2=CC=CC=1OCC1CO1 GXHWSJREEBJWPX-UHFFFAOYSA-N 0.000 description 1
- RBICJSJRIUQJPW-UHFFFAOYSA-N 4-[2-hydroxy-3-(methylamino)propoxy]-1,3-dihydrobenzimidazol-2-one hydrochloride Chemical compound Cl.OC(COC1=CC=CC=2NC(NC21)=O)CNC RBICJSJRIUQJPW-UHFFFAOYSA-N 0.000 description 1
- LOGDTPHXBCAUJY-UHFFFAOYSA-N 4-[3-(dicyclopentylamino)-2-hydroxypropoxy]-7-methyl-1,3-dihydrobenzimidazol-2-one hydrochloride Chemical compound Cl.C1(CCCC1)N(CC(COC1=CC=C(C=2NC(NC21)=O)C)O)C2CCCC2 LOGDTPHXBCAUJY-UHFFFAOYSA-N 0.000 description 1
- SYMGMNVMMISOHX-UHFFFAOYSA-N 4-[3-(tert-butylamino)-2-hydroxypropoxy]-1,3-dihydrobenzimidazole-2-thione;hydrochloride Chemical compound Cl.CC(C)(C)NCC(O)COC1=CC=CC2=C1NC(=S)N2 SYMGMNVMMISOHX-UHFFFAOYSA-N 0.000 description 1
- HIQCTHFRLRVNPP-UHFFFAOYSA-N 4-methyl-2,3-dinitrophenol Chemical compound CC1=CC=C(O)C([N+]([O-])=O)=C1[N+]([O-])=O HIQCTHFRLRVNPP-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- OFBXCNKLOZOCQK-UHFFFAOYSA-N Cl.CC1=CC=CC2=C1NC(=O)N2 Chemical compound Cl.CC1=CC=CC2=C1NC(=O)N2 OFBXCNKLOZOCQK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 241000978776 Senegalia senegal Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([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
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 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
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- IYWYMFZAZUYNLC-UHFFFAOYSA-N n-benzylcyclohexanamine Chemical compound C=1C=CC=CC=1CNC1CCCCC1 IYWYMFZAZUYNLC-UHFFFAOYSA-N 0.000 description 1
- PPVZYCGBQWWSKG-UHFFFAOYSA-N n-benzylcyclopentanamine Chemical compound C=1C=CC=CC=1CNC1CCCC1 PPVZYCGBQWWSKG-UHFFFAOYSA-N 0.000 description 1
- OUMBFMLKPJUWDQ-UHFFFAOYSA-N n-benzylpropan-1-amine Chemical compound CCCNCC1=CC=CC=C1 OUMBFMLKPJUWDQ-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
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000000376 reactant Substances 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
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 235000012976 tarts 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB18438/77A GB1595316A (en) | 1977-05-03 | 1977-05-03 | 4-(3-amino-2-hydroxy-propoxy)-benzimidazole derivatives and pharmaceutical compositions containing them |
| GB4915677 | 1977-11-25 | ||
| GB220878 | 1978-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781556L true NO781556L (no) | 1978-11-06 |
Family
ID=27254036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781556A NO781556L (no) | 1977-05-03 | 1978-05-02 | Benzimidazol-derivater. |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS53135979A (it) |
| AR (2) | AR220335A1 (it) |
| AU (1) | AU3569678A (it) |
| DE (1) | DE2819458A1 (it) |
| DK (1) | DK190378A (it) |
| ES (1) | ES469353A1 (it) |
| FI (1) | FI781349A (it) |
| FR (1) | FR2399414A1 (it) |
| GR (1) | GR73669B (it) |
| IL (1) | IL54591A0 (it) |
| IT (1) | IT1096276B (it) |
| LU (1) | LU79591A1 (it) |
| MC (1) | MC1192A1 (it) |
| NL (1) | NL7804794A (it) |
| NO (1) | NO781556L (it) |
| NZ (1) | NZ187066A (it) |
| PT (1) | PT67980A (it) |
| SE (1) | SE7805140L (it) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2801980A1 (de) * | 1978-01-18 | 1979-07-19 | Boehringer Mannheim Gmbh | 4-hydroxy-2-benzimidazolin-thion- derivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| EP0003758A1 (de) * | 1978-02-09 | 1979-09-05 | Ciba-Geigy Ag | Verätherte Hydroxy-benzodiheterocyclen und ihre Säureadditionssalze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate |
| DE2905877A1 (de) * | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CH661501A5 (fr) * | 1982-01-26 | 1987-07-31 | Oreal | Composes derivant du amino-3 propanol-2 utilisables pour la teinture des cheveux, leur procede de preparation, composition de teinture les contenant et procede de teinture de cheveux correspondant. |
| DE3839743A1 (de) * | 1988-11-25 | 1990-05-31 | Hoechst Ag | Verfahren zur herstellung von benzimidazolonen |
| US9784726B2 (en) | 2013-01-08 | 2017-10-10 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatment |
| GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1058822A (en) * | 1963-07-30 | 1967-02-15 | Ici Ltd | 3-amino-2-hydroxypropoxy heterocyclic derivatives |
| CH559729A5 (it) * | 1970-10-23 | 1975-03-14 | Hoechst Ag | |
| US4081447A (en) * | 1975-04-09 | 1978-03-28 | Abbott Laboratories | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof |
| CH624395A5 (it) * | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag |
-
1978
- 1978-04-26 NZ NZ187066A patent/NZ187066A/xx unknown
- 1978-04-27 IL IL54591A patent/IL54591A0/xx unknown
- 1978-04-27 FR FR7812492A patent/FR2399414A1/fr active Pending
- 1978-05-02 DK DK190378A patent/DK190378A/da not_active Application Discontinuation
- 1978-05-02 FI FI781349A patent/FI781349A/fi not_active Application Discontinuation
- 1978-05-02 ES ES469353A patent/ES469353A1/es not_active Expired
- 1978-05-02 NO NO781556A patent/NO781556L/no unknown
- 1978-05-02 PT PT67980A patent/PT67980A/pt unknown
- 1978-05-02 JP JP5241778A patent/JPS53135979A/ja active Pending
- 1978-05-02 MC MC781299A patent/MC1192A1/xx unknown
- 1978-05-03 NL NL7804794A patent/NL7804794A/xx not_active Application Discontinuation
- 1978-05-03 IT IT23000/78A patent/IT1096276B/it active
- 1978-05-03 AU AU35696/78A patent/AU3569678A/en active Pending
- 1978-05-03 SE SE7805140A patent/SE7805140L/xx unknown
- 1978-05-03 DE DE19782819458 patent/DE2819458A1/de not_active Withdrawn
- 1978-05-03 LU LU79591A patent/LU79591A1/de unknown
- 1978-05-31 AR AR272019A patent/AR220335A1/es active
-
1979
- 1979-01-24 GR GR56130A patent/GR73669B/el unknown
- 1979-07-06 AR AR277226A patent/AR219173A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| MC1192A1 (fr) | 1979-02-23 |
| FR2399414A1 (fr) | 1979-03-02 |
| AR219173A1 (es) | 1980-07-31 |
| GR73669B (it) | 1984-03-28 |
| IT1096276B (it) | 1985-08-26 |
| SE7805140L (sv) | 1978-11-04 |
| IL54591A0 (en) | 1978-07-31 |
| JPS53135979A (en) | 1978-11-28 |
| NL7804794A (nl) | 1978-11-07 |
| FI781349A (fi) | 1978-11-04 |
| PT67980B (it) | 1980-05-05 |
| PT67980A (en) | 1978-06-01 |
| NZ187066A (en) | 1981-02-11 |
| IT7823000A0 (it) | 1978-05-03 |
| AR220335A1 (es) | 1980-10-31 |
| DE2819458A1 (de) | 1978-11-16 |
| DK190378A (da) | 1978-11-04 |
| ES469353A1 (es) | 1980-01-01 |
| LU79591A1 (de) | 1979-06-13 |
| AU3569678A (en) | 1979-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0207901B1 (en) | Antianaphylactic and antibronchospastic n-benzhydryldiazacycloalkylalkananilides | |
| DK155367B (da) | Analogifremgangsmaade til fremstilling af 2-nitroimidazolderivater | |
| NO140589B (no) | Analogifremgangsmaate for fremstilling av nye, terapeutisk aktive 3,4-dihydrokarbostyrilderivater | |
| CZ174297A3 (en) | Xanthine derivatives, process of their preparation and medicaments containing thereof | |
| NO781556L (no) | Benzimidazol-derivater. | |
| US4980365A (en) | N-substituted-5,6-dimethoxy-1,2-benzisoxazole-3-propanamine and related compounds as analgesic and hypotensive agents | |
| NO126734B (it) | ||
| NO166557B (no) | Innretning for omstabling av en bladstabel. | |
| GB1581500A (en) | Pyridobenzodiazepines | |
| PT94070A (pt) | Processo para a preparacao de derivados de piperazina | |
| NO150605B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyridinyl-aminoalkyletere | |
| CA2421219A1 (en) | Arylpiperazine derivatives and their use as psychopharmaceuticals | |
| CA1208643A (en) | 1,5-diphenyl-pyrazolin-3-one compounds, process and intermediates for preparation thereof and pharmaceutical compositions containing them | |
| FI80269C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla bis(piperazinyl- eller homopiperazinyl)alkaner. | |
| NO803693L (no) | 2,3-indoldion-derivater. | |
| US6232337B1 (en) | Selective β3 adrenergic agonists | |
| JPS60158170A (ja) | エテニルフェノールインドール誘導体及びそれらの塩、これらの製造方法並びにこれらを含有する薬剤 | |
| NO124309B (it) | ||
| US3646146A (en) | Diphenylcyclopropyl-methyl-amines | |
| DK146718B (da) | Analogifremgangsmaade til fremstilling af benzobicyklononener | |
| US3723434A (en) | Piperazino isoquinoline bronchodilators | |
| HUT72294A (en) | Cyclic amine derivatives, pharmaceutical compositions containing them and process for producing thereof | |
| NO327549B1 (no) | Benzo[G]kinolinderivater for behandling av glaukom og myopi | |
| Norton et al. | The Synthesis of Some Substituted 8-Aminoquinolines1 | |
| EP0010392A1 (en) | Heterocyclic coumarin derivatives, their preparation and pharmaceutical compositions comprising said derivatives |