DD274215A5 - Verfahren zur herstellung von neuen benzimidazol-derivaten - Google Patents

Verfahren zur herstellung von neuen benzimidazol-derivaten Download PDF

Info

Publication number: DD274215A5
Authority: DD; German Democratic Republic
Prior art keywords: ethyl; dihydro; acid; concentrated; benzimidazole derivatives
Prior art date: 1987-08-25

Application number

DD88319141A

Other languages

German (de)

English (en)

Inventor

Klaus Schoellkopf

Helmut Wachtel

Original Assignee

��@��k��

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.)

1987-08-25

Filing date

1988-08-23

Publication date

1989-12-13

1988-08-23 Application filed by ��@��k�� filed Critical ��@��k��

1989-12-13 Publication of DD274215A5 publication Critical patent/DD274215A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims abstract description 8
229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims abstract description 7
150000001556 benzimidazoles Chemical class 0.000 title description 6
150000003839 salts Chemical class 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
229910052717 sulfur Chemical group 0.000 claims abstract description 5
239000011593 sulfur Chemical group 0.000 claims abstract description 5
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 4
229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 20
-1 2- (N, N-dipropylamino) ethyl Chemical group 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
230000003291 dopaminomimetic effect Effects 0.000 description 5
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
210000003169 central nervous system Anatomy 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
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 2
PLOMFWYHXDTNRJ-UHFFFAOYSA-N 3-[2-(dipropylamino)ethyl]benzene-1,2-diamine Chemical compound CCCN(CCC)CCC1=CC=CC(N)=C1N PLOMFWYHXDTNRJ-UHFFFAOYSA-N 0.000 description 2
IFDIMWJXGASBLT-UHFFFAOYSA-N 3-[2-[butyl(methyl)amino]ethyl]benzene-1,2-diamine Chemical compound CCCCN(C)CCC1=CC=CC(N)=C1N IFDIMWJXGASBLT-UHFFFAOYSA-N 0.000 description 2
XPCWMKVIKQPFSX-UHFFFAOYSA-N 4-[2-(dipropylamino)ethyl]-1,3-dihydrobenzimidazol-2-one Chemical compound CCCN(CCC)CCC1=CC=CC2=C1NC(=O)N2 XPCWMKVIKQPFSX-UHFFFAOYSA-N 0.000 description 2
IPNDYABROJLNOR-UHFFFAOYSA-N 4-[2-[butyl(methyl)amino]ethyl]-1,3-dihydrobenzimidazole-2-thione Chemical compound CCCCN(C)CCC1=CC=CC2=C1NC(=S)N2 IPNDYABROJLNOR-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000024172 Cardiovascular disease Diseases 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
230000001800 adrenalinergic effect Effects 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 2
229960002802 bromocriptine Drugs 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000470 constituent Substances 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
229940005501 dopaminergic agent Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
150000002390 heteroarenes Chemical class 0.000 description 2
229960004502 levodopa Drugs 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
ULOCHOLAPFZTGB-UHFFFAOYSA-N 1,3-benzothiazol-3-ium;bromide Chemical compound [Br-].C1=CC=C2SC=[NH+]C2=C1 ULOCHOLAPFZTGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HTOMICONFYSCTM-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]-n,n,n',n'-tetrapropylmethanediamine Chemical compound CCCN(CCC)C(OC(C)(C)C)N(CCC)CCC HTOMICONFYSCTM-UHFFFAOYSA-N 0.000 description 1
VHZHEQWWBYEMCV-UHFFFAOYSA-N 2-(2,1,3-benzothiadiazol-4-yl)-n-butyl-n-methylacetamide Chemical compound CCCCN(C)C(=O)CC1=CC=CC2=NSN=C12 VHZHEQWWBYEMCV-UHFFFAOYSA-N 0.000 description 1
JUOHNWGCIDUACA-UHFFFAOYSA-N 2-(2,1,3-benzothiadiazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC2=NSN=C12 JUOHNWGCIDUACA-UHFFFAOYSA-N 0.000 description 1
CQOXALSPDITZGJ-UHFFFAOYSA-N 2-(2,3-dinitrophenyl)-n,n-dimethylethenamine Chemical compound CN(C)C=CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CQOXALSPDITZGJ-UHFFFAOYSA-N 0.000 description 1
IYXGFOYZMPAPMB-UHFFFAOYSA-N 2-(2,3-dinitrophenyl)-n-(2-phenylethyl)-n-propylacetamide Chemical compound C=1C=CC([N+]([O-])=O)=C([N+]([O-])=O)C=1CC(=O)N(CCC)CCC1=CC=CC=C1 IYXGFOYZMPAPMB-UHFFFAOYSA-N 0.000 description 1
DFSSHXQXUVISBJ-UHFFFAOYSA-N 2-(2,3-dinitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=CC(CC#N)=C1[N+]([O-])=O DFSSHXQXUVISBJ-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
GZXOXBGCYFJIAN-UHFFFAOYSA-N 3-[2-[2-phenylethyl(propyl)amino]ethyl]benzene-1,2-diamine Chemical compound C=1C=CC(N)=C(N)C=1CCN(CCC)CCC1=CC=CC=C1 GZXOXBGCYFJIAN-UHFFFAOYSA-N 0.000 description 1
VVCJBYVWJIAZOU-UHFFFAOYSA-N 3-[2-[propyl(2-thiophen-2-ylethyl)amino]ethyl]benzene-1,2-diamine Chemical compound C=1C=CC(N)=C(N)C=1CCN(CCC)CCC1=CC=CS1 VVCJBYVWJIAZOU-UHFFFAOYSA-N 0.000 description 1
206010000599 Acromegaly Diseases 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
241001061127 Thione Species 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000004651 carbonic acid esters Chemical class 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
239000003245 coal Substances 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 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
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
229960004704 dihydroergotamine Drugs 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
208000031424 hyperprolactinemia Diseases 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012280 lithium aluminium hydride Substances 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 1
IIIRPZWDICEMGU-UHFFFAOYSA-N n-(2-phenylethyl)propan-1-amine Chemical compound CCCNCCC1=CC=CC=C1 IIIRPZWDICEMGU-UHFFFAOYSA-N 0.000 description 1
JDYQEIARYYFLSO-UHFFFAOYSA-N n-[2-(2,3-dinitrophenyl)ethyl]-n-propylpropan-1-amine Chemical compound CCCN(CCC)CCC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O JDYQEIARYYFLSO-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 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
230000003389 potentiating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000008327 renal blood flow Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
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150000003852 triazoles Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)

DD88319141A 1987-08-25 1988-08-23 Verfahren zur herstellung von neuen benzimidazol-derivaten DD274215A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873728695 DE3728695A1 (de)	1987-08-25	1987-08-25	Neue benzimidazol-derivate

Publications (1)

Publication Number	Publication Date
DD274215A5 true DD274215A5 (de)	1989-12-13

Family

ID=6334659

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88319141A DD274215A5 (de)	1987-08-25	1988-08-23	Verfahren zur herstellung von neuen benzimidazol-derivaten

Country Status (17)

Country	Link
US (1)	US4925854A (fr)
EP (1)	EP0304789B1 (fr)
JP (1)	JP2818170B2 (fr)
AT (1)	ATE86982T1 (fr)
AU (1)	AU615939B2 (fr)
CA (1)	CA1330440C (fr)
DD (1)	DD274215A5 (fr)
DE (2)	DE3728695A1 (fr)
DK (1)	DK169701B1 (fr)
ES (1)	ES2054752T3 (fr)
FI (1)	FI99013C (fr)
HU (1)	HU201746B (fr)
IE (1)	IE63283B1 (fr)
IL (1)	IL87561A (fr)
NO (1)	NO170852C (fr)
PT (1)	PT88326B (fr)
ZA (1)	ZA886336B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE914003A1 (en) *	1990-11-20	1992-05-20	Astra Pharma Prod	Biologically Active Amines
US5371102A (en) *	1992-03-11	1994-12-06	University Of Hawaii	Compositions and methods of inhibiting thyroid activity
PE27997A1 (es)	1994-04-29	1997-09-20	Lilly Co Eli	Antagonistas de receptores de taquicininas
US5565454A (en) *	1995-05-31	1996-10-15	Ergo Science, Incorporated	Method for preventing intervention-associated stenosis and other symptoms associated with stenosis of blood vessels following non-bypass, invasive interventions
TW356468B (en) *	1995-09-15	1999-04-21	Astra Pharma Prod	Benzothiazolone compounds useful as beta2-adrenoreceptor and dopamine DA2 receptor agonists process for preparing same and pharmaceutical compositions containing same
GB9526511D0 (en) *	1995-12-23	1996-02-28	Astra Pharma Prod	Pharmaceutically active compounds
WO2004032861A2 (fr) *	2002-10-11	2004-04-22	Bristol-Myers Squibb Company	Composes hexahydro-benzimidazolones utiles en tant qu'agents anti-inflammatoires
MX346346B (es)	2011-12-16	2017-03-14	Colgate Palmolive Co	Composiciones que cambian de color.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3813409A (en) *	1972-07-31	1974-05-28	Squibb & Sons Inc	Benzimidazolinone compounds
DE3042481A1 (de) *	1980-11-11	1982-06-16	A. Nattermann & Cie GmbH, 5000 Köln	(omega)-(2-oxo-benzazolinyl)-alkansaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
US4367337A (en) *	1981-01-05	1983-01-04	The Sherwin-Williams Company	Process for conversion of benzimidazolones to benzotriazoles
WO1986001204A1 (fr) *	1984-08-15	1986-02-27	Schering Aktiengesellschaft	Nouveaux derives de dopamine, procede pour leur production et leur utilisation comme produits medicinaux
US4554287A (en) *	1984-09-12	1985-11-19	Smithkline Beckman Corporation	Antihypertensive 7-[2-(dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones

1987
- 1987-08-25 DE DE19873728695 patent/DE3728695A1/de not_active Withdrawn
1988
- 1988-08-17 ES ES88113339T patent/ES2054752T3/es not_active Expired - Lifetime
- 1988-08-17 DE DE8888113339T patent/DE3879322D1/de not_active Expired - Lifetime
- 1988-08-17 EP EP88113339A patent/EP0304789B1/fr not_active Expired - Lifetime
- 1988-08-17 AT AT88113339T patent/ATE86982T1/de active
- 1988-08-22 IE IE255288A patent/IE63283B1/en not_active IP Right Cessation
- 1988-08-23 DD DD88319141A patent/DD274215A5/de not_active IP Right Cessation
- 1988-08-23 JP JP63207486A patent/JP2818170B2/ja not_active Expired - Lifetime
- 1988-08-24 NO NO883776A patent/NO170852C/no unknown
- 1988-08-24 CA CA000575617A patent/CA1330440C/fr not_active Expired - Fee Related
- 1988-08-24 PT PT88326A patent/PT88326B/pt not_active IP Right Cessation
- 1988-08-24 HU HU884447A patent/HU201746B/hu not_active IP Right Cessation
- 1988-08-25 IL IL87561A patent/IL87561A/xx not_active IP Right Cessation
- 1988-08-25 FI FI883930A patent/FI99013C/fi not_active IP Right Cessation
- 1988-08-25 US US07/236,383 patent/US4925854A/en not_active Expired - Fee Related
- 1988-08-25 AU AU21498/88A patent/AU615939B2/en not_active Ceased
- 1988-08-25 DK DK474288A patent/DK169701B1/da not_active IP Right Cessation
- 1988-08-25 ZA ZA886336A patent/ZA886336B/xx unknown

Also Published As

Publication number	Publication date
FI883930L (fi)	1989-02-26
ATE86982T1 (de)	1993-04-15
PT88326A (pt)	1989-06-30
IL87561A0 (en)	1989-01-31
IE63283B1 (en)	1995-04-05
FI99013B (fi)	1997-06-13
ZA886336B (en)	1989-04-26
HU201746B (en)	1990-12-28
DE3728695A1 (de)	1989-03-09
AU2149888A (en)	1989-03-02
DK474288A (da)	1989-02-26
CA1330440C (fr)	1994-06-28
FI99013C (fi)	1997-09-25
DK474288D0 (da)	1988-08-25
NO170852B (no)	1992-09-07
NO883776L (no)	1989-02-27
ES2054752T3 (es)	1994-08-16
IE882552L (en)	1989-02-25
FI883930A0 (fi)	1988-08-25
EP0304789A3 (en)	1989-10-04
DK169701B1 (da)	1995-01-16
HUT49589A (en)	1989-10-30
NO883776D0 (no)	1988-08-24
AU615939B2 (en)	1991-10-17
JPS6468359A (en)	1989-03-14
JP2818170B2 (ja)	1998-10-30
IL87561A (en)	1993-02-21
DE3879322D1 (de)	1993-04-22
EP0304789B1 (fr)	1993-03-17
PT88326B (pt)	1995-03-31
EP0304789A2 (fr)	1989-03-01
US4925854A (en)	1990-05-15
NO170852C (no)	1992-12-16

Legal Events

Date	Code	Title	Description
1994-09-01	VZ	Disclaimer of patent (art. 11 and 12 extension act)

Publication	Publication Date	Title
EP0269968A2 (fr)	1988-06-08	Dérivés d'amine hétéroaromatiques, médicaments les contenant et leur procédé de préparation
EP0121753A2 (fr)	1984-10-17	1-(1,3-Dioxolan-2-ylméthyl)-azoles, leur sels, leurs procédés de préparation et les préparations pharmaceutiques les contenant
EP0304789B1 (fr)	1993-03-17	Dérivés de benzimidazole
CH641757A5 (en)	1984-03-15	O-Alkylated hydroxylamines and process for the preparation thereof
DE1620449B2 (de)	1973-07-26	Substituierte benzimidazole und verfahren zu ihrer herstellung
DE2220906A1 (de)	1973-11-15	Neue substituierte 2-phenylaminoimidazoline-(2), deren saeureadditionssalze sowie verfahren zu deren herstellung
CH631970A5 (de)	1982-09-15	Verfahren zur herstellung neuer substituierter 2-phenylamino-imidazoline-(2) und deren saeureadditionssalze.
CH617701A5 (fr)	1980-06-13
DE2248477A1 (de)	1973-04-12	Imidazolinverbindungen
DE2723464A1 (de)	1977-12-08	Aryltrifluoraethylamine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0173933A1 (fr)	1986-03-12	Dérivés de la 1,6-naphthyridine, procédé pour leur préparation et médicaments les contenant
DE2314114A1 (de)	1973-10-04	Neue thiazolcarbonsaeurederivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen
CH628346A5 (de)	1982-02-26	Verfahren zur herstellung neuer xanthinderivate.
CH633288A5 (de)	1982-11-30	Verfahren zur herstellung von neuen heterocyclylaminoderivaten.
DE2300018C2 (de)	1983-01-20	1-[N-Methyl-N-(&beta;-phenyläthyl)-3-aminopropyl]- benzimidazol-Abkömmlinge
DE2521709A1 (de)	1976-02-05	Verfahren zur herstellung von neuen 2-arylamino-2-imidazolinderivaten
EP0427827B1 (fr)	1997-01-15	8-alpha-ACYLAMINO-ERGOLINES, LEUR PRODUCTION ET LEUR UTILISATION EN TANT QUE MEDICAMENTS
DE2417063C2 (de)	1982-05-13	Tricyclische Sulfoximid-Derivate
EP0873315B1 (fr)	2003-04-23	Derives de phenanthridine, procedes permettant de les preparer et medicaments contenant des phenanthridines
DE2331721A1 (de)	1974-01-10	Verfahren zur herstellung neuer heterocyclischer verbindungen
EP1114037B1 (fr)	2004-05-12	Derives de benzoxazine et de benzothiazine et leur utilisation dans des produits pharmaceutiques
EP0160173A1 (fr)	1985-11-06	Dérivés de benzothiazole, leurs procédés de préparation et médicament les contenant
DE3531504A1 (de)	1987-03-12	3-aminomethylpyrrol-1-yl-alkylamine und diese verbindungen enthaltende therapeutische mittel
CH626870A5 (fr)	1981-12-15
DE2438965A1 (de)	1976-02-26	Basisch substituierte 3,4-dihydro2h-isochinolin-1-thione und verfahren zu ihrer herstellung