NO781556L - Benzimidazol-derivater. - Google Patents

Benzimidazol-derivater.

Info

Publication number: NO781556L
Authority: NO; Norway
Prior art keywords: lower alkyl; hydrogen atom; benzimidazolinone; formula; alkyl group
Prior art date: 1977-05-03

Application number

NO781556A

Other languages

English (en)

Norwegian (no)

Inventor

Roger Edward Markwell

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-05-03

Filing date

1978-05-02

Publication date

1978-11-06

1977-05-03 Priority claimed from GB18438/77A external-priority patent/GB1595316A/en

1978-05-02 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1978-11-06 Publication of NO781556L publication Critical patent/NO781556L/no

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
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RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
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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
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239000000205 acacia gum Substances 0.000 description 1
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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
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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
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239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
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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
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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)

NO781556A 1977-05-03 1978-05-02 Benzimidazol-derivater. NO781556L (no)

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 (es)
AR (2)	AR220335A1 (es)
AU (1)	AU3569678A (es)
DE (1)	DE2819458A1 (es)
DK (1)	DK190378A (es)
ES (1)	ES469353A1 (es)
FI (1)	FI781349A (es)
FR (1)	FR2399414A1 (es)
GR (1)	GR73669B (es)
IL (1)	IL54591A0 (es)
IT (1)	IT1096276B (es)
LU (1)	LU79591A1 (es)
MC (1)	MC1192A1 (es)
NL (1)	NL7804794A (es)
NO (1)	NO781556L (es)
NZ (1)	NZ187066A (es)
PT (1)	PT67980A (es)
SE (1)	SE7805140L (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1058822A (en) *	1963-07-30	1967-02-15	Ici Ltd	3-amino-2-hydroxypropoxy heterocyclic derivatives
GB1363735A (en) *	1970-10-23	1974-08-14	Hoechst Ag	Process for the manufacture of benzimidazolones
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 (es) *	1976-01-08	1981-07-31	Ciba Geigy Ag

1978
- 1978-04-26 NZ NZ187066A patent/NZ187066A/xx unknown
- 1978-04-27 FR FR7812492A patent/FR2399414A1/fr active Pending
- 1978-04-27 IL IL54591A patent/IL54591A0/xx unknown
- 1978-05-02 JP JP5241778A patent/JPS53135979A/ja active Pending
- 1978-05-02 MC MC781299A patent/MC1192A1/xx unknown
- 1978-05-02 PT PT67980A patent/PT67980A/pt unknown
- 1978-05-02 ES ES469353A patent/ES469353A1/es not_active Expired
- 1978-05-02 FI FI781349A patent/FI781349A/fi not_active Application Discontinuation
- 1978-05-02 NO NO781556A patent/NO781556L/no unknown
- 1978-05-02 DK DK190378A patent/DK190378A/da not_active Application Discontinuation
- 1978-05-03 IT IT23000/78A patent/IT1096276B/it active
- 1978-05-03 SE SE7805140A patent/SE7805140L/xx unknown
- 1978-05-03 NL NL7804794A patent/NL7804794A/xx not_active Application Discontinuation
- 1978-05-03 AU AU35696/78A patent/AU3569678A/en active Pending
- 1978-05-03 LU LU79591A patent/LU79591A1/de unknown
- 1978-05-03 DE DE19782819458 patent/DE2819458A1/de not_active Withdrawn
- 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
DK190378A (da)	1978-11-04
JPS53135979A (en)	1978-11-28
ES469353A1 (es)	1980-01-01
AR219173A1 (es)	1980-07-31
FI781349A (fi)	1978-11-04
MC1192A1 (fr)	1979-02-23
IL54591A0 (en)	1978-07-31
FR2399414A1 (fr)	1979-03-02
GR73669B (es)	1984-03-28
AU3569678A (en)	1979-11-08
NZ187066A (en)	1981-02-11
DE2819458A1 (de)	1978-11-16
NL7804794A (nl)	1978-11-07
SE7805140L (sv)	1978-11-04
LU79591A1 (de)	1979-06-13
IT1096276B (it)	1985-08-26
PT67980B (es)	1980-05-05
IT7823000A0 (it)	1978-05-03
PT67980A (en)	1978-06-01
AR220335A1 (es)	1980-10-31

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