DE2821410A1 - Aminoalkylbenzolderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen - Google Patents
Aminoalkylbenzolderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungenInfo
- Publication number
- DE2821410A1 DE2821410A1 DE19782821410 DE2821410A DE2821410A1 DE 2821410 A1 DE2821410 A1 DE 2821410A1 DE 19782821410 DE19782821410 DE 19782821410 DE 2821410 A DE2821410 A DE 2821410A DE 2821410 A1 DE2821410 A1 DE 2821410A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- hydrogen
- methyl
- group
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- -1 AMINO ALKYLBENZENE DERIVATIVES Chemical class 0.000 title claims description 79
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 122
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 40
- 150000001412 amines Chemical class 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229960001340 histamine Drugs 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 150000002540 isothiocyanates Chemical class 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 150000004702 methyl esters Chemical class 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 239000002674 ointment Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 2
- 230000000172 allergic effect Effects 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- IMTXPCPHMUYDHQ-UHFFFAOYSA-N 1-n-methyl-1-n'-[2-[[3-(methylaminomethyl)phenyl]methylsulfanyl]ethyl]-2-nitroethene-1,1-diamine Chemical compound CNCC1=CC=CC(CSCCNC(NC)=C[N+]([O-])=O)=C1 IMTXPCPHMUYDHQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 149
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 132
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
- 239000000377 silicon dioxide Substances 0.000 description 73
- 229910021529 ammonia Inorganic materials 0.000 description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 150000004985 diamines Chemical class 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 210000002784 stomach Anatomy 0.000 description 12
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 150000003891 oxalate salts Chemical class 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000012280 lithium aluminium hydride Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000009858 acid secretion Effects 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 4
- ZEQMMXMSZSMEND-UHFFFAOYSA-N 3-[3-[(dimethylamino)methyl]phenoxy]propan-1-amine Chemical compound CN(C)CC1=CC=CC(OCCCN)=C1 ZEQMMXMSZSMEND-UHFFFAOYSA-N 0.000 description 4
- 241001440269 Cutina Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 235000019502 Orange oil Nutrition 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000010502 orange oil Substances 0.000 description 4
- 125000005544 phthalimido group Chemical group 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
- 241001631457 Cannula Species 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- REPYKJUHULFZIZ-UHFFFAOYSA-N OC(=O)C(O)=O.OC(=O)C(O)=O.CNCC1=CC=CC(OCCCN)=C1 Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.CNCC1=CC=CC(OCCCN)=C1 REPYKJUHULFZIZ-UHFFFAOYSA-N 0.000 description 3
- VUUSSTMNTMTMID-UHFFFAOYSA-N [3-[(dimethylamino)methyl]phenyl]methanol Chemical compound CN(C)CC1=CC=CC(CO)=C1 VUUSSTMNTMTMID-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229960004977 anhydrous lactose Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- HXMWGMZZNGHVPQ-UHFFFAOYSA-N 3-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=CC(O)=C1 HXMWGMZZNGHVPQ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-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
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 210000003238 esophagus Anatomy 0.000 description 2
- BSGRLBPZSRZQOR-UHFFFAOYSA-N ethene-1,1-diamine Chemical compound NC(N)=C BSGRLBPZSRZQOR-UHFFFAOYSA-N 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-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
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- SEPBXSJXWMHUQA-UHFFFAOYSA-N n,n-dimethyl-1-phenylmethanamine;propan-1-ol Chemical compound CCCO.CN(C)CC1=CC=CC=C1 SEPBXSJXWMHUQA-UHFFFAOYSA-N 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 229910003445 palladium oxide Inorganic materials 0.000 description 2
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/10—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/08—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/30—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to nitro or nitroso groups
- C07C279/32—N-nitroguanidines
- C07C279/36—Substituted N-nitroguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB20660/77A GB1604674A (en) | 1977-05-17 | 1977-05-17 | Aminoalkyl-benzene derivatives |
GB4012977 | 1977-09-27 | ||
GB1744478 | 1978-05-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2821410A1 true DE2821410A1 (de) | 1978-11-30 |
Family
ID=27257503
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19782821410 Withdrawn DE2821410A1 (de) | 1977-05-17 | 1978-05-16 | Aminoalkylbenzolderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS53149936A (sv) |
AU (2) | AU523496B2 (sv) |
CH (2) | CH643238A5 (sv) |
DE (1) | DE2821410A1 (sv) |
DK (1) | DK214878A (sv) |
ES (1) | ES469953A1 (sv) |
FI (1) | FI781490A (sv) |
FR (2) | FR2401135A1 (sv) |
IE (1) | IE46886B1 (sv) |
IT (1) | IT1156755B (sv) |
NL (1) | NL7805344A (sv) |
NZ (1) | NZ187235A (sv) |
SE (1) | SE443558B (sv) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0002930A1 (en) * | 1977-12-23 | 1979-07-11 | Glaxo Group Limited | Amine derivatives, their preparation and pharmaceutical compositions containing them |
EP0023578A1 (en) * | 1979-07-03 | 1981-02-11 | Shionogi & Co., Ltd. | Aminoalkylbenzene derivatives, process for their preparation and pharmaceutical compositions |
US4293557A (en) | 1979-07-03 | 1981-10-06 | Teikoku Hormone Mfg. Co., Ltd. | Antiulcer phenoxypropylamine derivatives |
EP0055179A1 (en) * | 1980-12-22 | 1982-06-30 | Merck & Co. Inc. | Aminoalkyl pyridine derivatives |
EP0057981A2 (en) * | 1981-02-09 | 1982-08-18 | Beecham Group Plc | Aromatic compounds, processes for their preparation and their use |
EP0067436A2 (en) * | 1981-06-15 | 1982-12-22 | Merck & Co. Inc. | Diamino isothiazole -1-oxides and -1,1-dioxides as gastric secretion inhibitors |
EP0071434A2 (en) * | 1981-07-24 | 1983-02-09 | Glaxo Group Limited | Heterocyclic derivatives |
EP0082376A2 (en) * | 1981-12-21 | 1983-06-29 | Merck & Co. Inc. | Substituted derivatives of amino alkane diols as gastric secretion inhibitors |
US4442110A (en) * | 1978-04-26 | 1984-04-10 | Glaxo Group Limited | 1H-1,2,4-Triazole-3,5-diamine derivatives and use as selective histamine H2 -antagonists |
EP0016565B1 (en) * | 1979-03-02 | 1984-05-23 | Glaxo Group Limited | 1,2,4-triazole derivatives, processes for their production and pharmaceutical compositions containing them |
EP0029311B1 (en) * | 1979-10-31 | 1985-01-23 | Merck & Co. Inc. | Aminoalkyl benzofuran derivatives, their production and compositions containing them |
EP0029303B1 (en) * | 1979-10-22 | 1985-01-30 | Glaxo Group Limited | 1,2,4-triazole derivatives, processes for their production and pharmaceutical compositions containing them |
US4522943A (en) * | 1981-05-18 | 1985-06-11 | Bristol-Myers Company | Chemical compounds |
US4526973A (en) * | 1981-05-18 | 1985-07-02 | Bristol-Myers Company | Chemical compounds |
EP1944305A1 (en) | 2003-05-21 | 2008-07-16 | Glaxo Group Limited | Quinoline derivatives as phosphodiesterase inhibitors |
EP2111223A1 (en) * | 2007-11-01 | 2009-10-28 | Acucela, Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS609750B2 (ja) * | 1979-07-03 | 1985-03-12 | 帝国臓器製薬株式会社 | 新規なn−置換フエノキシプロピルアミド化合物 |
FR2477537A1 (fr) * | 1980-03-07 | 1981-09-11 | Francaise Sucrerie | Nouvelles guanidines acylees, urees et urees substituees, leur procede de fabrication et leur application en tant que medicaments |
JPS57165348A (en) * | 1981-04-06 | 1982-10-12 | Teikoku Hormone Mfg Co Ltd | Novel aminoalkylbenzene derivative |
JPS5988458A (ja) * | 1982-11-12 | 1984-05-22 | Toyama Chem Co Ltd | アミン誘導体およびその塩 |
JPH0639466B2 (ja) * | 1987-08-03 | 1994-05-25 | 杏林製薬株式会社 | ウレア誘導体 |
JPH01131172A (ja) * | 1987-08-28 | 1989-05-24 | Toyama Chem Co Ltd | アミン誘導体およびその塩、それらの製造法、並びにそれらを含有する抗潰瘍剤 |
WO1993023360A1 (fr) * | 1992-05-12 | 1993-11-25 | Zeria Pharmaceutical Co., Ltd. | Nouveaux sels d'ammonium quaternaires et utilisation de ces sels comme medicament |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE636468A (sv) * | ||||
US2785201A (en) * | 1953-12-24 | 1957-03-12 | Personnes A Responsabilite Lim | Compounds of bis quaternary ammonium derivatives of phenylethylamine |
US3047628A (en) * | 1957-02-19 | 1962-07-31 | Hoffmann La Roche | Benzylamine derivatives |
GB993581A (en) * | 1960-03-03 | 1965-05-26 | Wellcome Found | Phenoxyalkylguanidines and their synthesis and pharmaceutical preparations containing them |
GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
GB1421792A (en) * | 1973-05-17 | 1976-01-21 | Smith Kline French Lab | Heterocyclic substituted-1, 1-diamino-ethylene derivatives methods for their preparation and compositions containing them |
JPS5227757A (en) * | 1975-08-26 | 1977-03-02 | Kyowa Hakko Kogyo Co Ltd | Preparation of 6-aminomethylnaphthalene derivatives |
-
1978
- 1978-05-09 IE IE940/78A patent/IE46886B1/en unknown
- 1978-05-10 NZ NZ187235A patent/NZ187235A/xx unknown
- 1978-05-11 FI FI781490A patent/FI781490A/fi not_active Application Discontinuation
- 1978-05-12 AU AU36067/78A patent/AU523496B2/en not_active Expired
- 1978-05-16 DE DE19782821410 patent/DE2821410A1/de not_active Withdrawn
- 1978-05-16 CH CH531578A patent/CH643238A5/de not_active IP Right Cessation
- 1978-05-16 DK DK214878A patent/DK214878A/da unknown
- 1978-05-16 SE SE7805591A patent/SE443558B/sv unknown
- 1978-05-17 NL NL7805344A patent/NL7805344A/xx not_active Application Discontinuation
- 1978-05-17 JP JP5870678A patent/JPS53149936A/ja active Granted
- 1978-05-17 IT IT7849419A patent/IT1156755B/it active
- 1978-05-17 ES ES469953A patent/ES469953A1/es not_active Expired
- 1978-05-17 FR FR7814594A patent/FR2401135A1/fr active Granted
- 1978-10-03 FR FR7828239A patent/FR2398718A1/fr active Granted
-
1982
- 1982-05-25 AU AU84117/82A patent/AU541144B2/en not_active Expired
- 1982-12-22 CH CH749182A patent/CH643233A5/de not_active IP Right Cessation
Non-Patent Citations (1)
Title |
---|
NICHTS ERMITTELT * |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0002930A1 (en) * | 1977-12-23 | 1979-07-11 | Glaxo Group Limited | Amine derivatives, their preparation and pharmaceutical compositions containing them |
US4442110A (en) * | 1978-04-26 | 1984-04-10 | Glaxo Group Limited | 1H-1,2,4-Triazole-3,5-diamine derivatives and use as selective histamine H2 -antagonists |
EP0016565B1 (en) * | 1979-03-02 | 1984-05-23 | Glaxo Group Limited | 1,2,4-triazole derivatives, processes for their production and pharmaceutical compositions containing them |
EP0023578A1 (en) * | 1979-07-03 | 1981-02-11 | Shionogi & Co., Ltd. | Aminoalkylbenzene derivatives, process for their preparation and pharmaceutical compositions |
US4293557A (en) | 1979-07-03 | 1981-10-06 | Teikoku Hormone Mfg. Co., Ltd. | Antiulcer phenoxypropylamine derivatives |
EP0029303B1 (en) * | 1979-10-22 | 1985-01-30 | Glaxo Group Limited | 1,2,4-triazole derivatives, processes for their production and pharmaceutical compositions containing them |
EP0029311B1 (en) * | 1979-10-31 | 1985-01-23 | Merck & Co. Inc. | Aminoalkyl benzofuran derivatives, their production and compositions containing them |
EP0055179A1 (en) * | 1980-12-22 | 1982-06-30 | Merck & Co. Inc. | Aminoalkyl pyridine derivatives |
US4427685A (en) | 1981-02-09 | 1984-01-24 | Beecham Group P.L.C. | Cycloalkylamino derivatives and their use in the treatment of peptic ulcers and the like |
EP0057981A2 (en) * | 1981-02-09 | 1982-08-18 | Beecham Group Plc | Aromatic compounds, processes for their preparation and their use |
EP0057981A3 (en) * | 1981-02-09 | 1982-08-25 | Beecham Group Plc | Aromatic compounds, processes for their preparation and their use |
US4526973A (en) * | 1981-05-18 | 1985-07-02 | Bristol-Myers Company | Chemical compounds |
US4522943A (en) * | 1981-05-18 | 1985-06-11 | Bristol-Myers Company | Chemical compounds |
EP0067436A3 (en) * | 1981-06-15 | 1983-01-19 | Merck & Co. Inc. | Diamino isothiazole -1-oxides and -1,1-dioxides as gastric secretion inhibitors |
EP0067436A2 (en) * | 1981-06-15 | 1982-12-22 | Merck & Co. Inc. | Diamino isothiazole -1-oxides and -1,1-dioxides as gastric secretion inhibitors |
EP0071434A2 (en) * | 1981-07-24 | 1983-02-09 | Glaxo Group Limited | Heterocyclic derivatives |
EP0071434A3 (en) * | 1981-07-24 | 1983-05-04 | Glaxo Group Limited | Heterocyclic derivatives |
EP0082376A2 (en) * | 1981-12-21 | 1983-06-29 | Merck & Co. Inc. | Substituted derivatives of amino alkane diols as gastric secretion inhibitors |
EP0082376A3 (en) * | 1981-12-21 | 1984-08-22 | Merck & Co. Inc. | Substituted derivatives of amino alkane diols as gastric secretion inhibitors |
EP1944305A1 (en) | 2003-05-21 | 2008-07-16 | Glaxo Group Limited | Quinoline derivatives as phosphodiesterase inhibitors |
EP2111223A1 (en) * | 2007-11-01 | 2009-10-28 | Acucela, Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
EP2111223A4 (en) * | 2007-11-01 | 2012-08-15 | Acucela Inc | AMIN DERIVATIVE COMPOUNDS FOR THE TREATMENT OF EYE DISEASES AND DRESSES |
US8450527B2 (en) | 2007-11-01 | 2013-05-28 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
US8716529B2 (en) | 2007-11-01 | 2014-05-06 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
US9056849B2 (en) | 2007-11-01 | 2015-06-16 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
US9452153B2 (en) | 2007-11-01 | 2016-09-27 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
Also Published As
Publication number | Publication date |
---|---|
JPS53149936A (en) | 1978-12-27 |
FR2401135A1 (fr) | 1979-03-23 |
AU541144B2 (en) | 1984-12-20 |
FI781490A (fi) | 1978-11-18 |
IT1156755B (it) | 1987-02-04 |
IE46886B1 (en) | 1983-10-19 |
DK214878A (da) | 1978-11-18 |
FR2401135B1 (sv) | 1983-08-19 |
AU523496B2 (en) | 1982-07-29 |
NZ187235A (en) | 1981-10-19 |
SE443558B (sv) | 1986-03-03 |
FR2398718B1 (sv) | 1982-10-15 |
AU3606778A (en) | 1979-11-15 |
ES469953A1 (es) | 1979-09-16 |
AU8411782A (en) | 1982-08-26 |
IE780940L (en) | 1978-11-17 |
NL7805344A (nl) | 1978-11-21 |
CH643233A5 (en) | 1984-05-30 |
CH643238A5 (en) | 1984-05-30 |
SE7805591L (sv) | 1978-11-18 |
IT7849419A0 (it) | 1978-05-17 |
FR2398718A1 (fr) | 1979-02-23 |
JPH0112744B2 (sv) | 1989-03-02 |
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