GB1604674A - Aminoalkyl-benzene derivatives - Google Patents
Aminoalkyl-benzene derivatives Download PDFInfo
- Publication number
- GB1604674A GB1604674A GB20660/77A GB2066077A GB1604674A GB 1604674 A GB1604674 A GB 1604674A GB 20660/77 A GB20660/77 A GB 20660/77A GB 2066077 A GB2066077 A GB 2066077A GB 1604674 A GB1604674 A GB 1604674A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- formula
- hydrogen
- nitro
- compound
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 102
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- -1 methylsulphonyl Chemical group 0.000 claims description 24
- 210000002784 stomach Anatomy 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 230000009858 acid secretion Effects 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 230000010412 perfusion Effects 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 229960001340 histamine Drugs 0.000 claims description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 10
- 241000700159 Rattus Species 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 claims description 8
- 230000008859 change Effects 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000005864 Sulphur Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- BSGRLBPZSRZQOR-UHFFFAOYSA-N ethene-1,1-diamine Chemical compound NC(N)=C BSGRLBPZSRZQOR-UHFFFAOYSA-N 0.000 claims description 7
- 150000002540 isothiocyanates Chemical class 0.000 claims description 7
- 150000003573 thiols Chemical class 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
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- 238000012360 testing method Methods 0.000 claims description 6
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
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- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 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 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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- 230000002496 gastric effect Effects 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- 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 2
- 235000007129 Cuminum cyminum Nutrition 0.000 claims description 2
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- 229920005439 Perspex® Polymers 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- 206010041899 Stab wound Diseases 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 210000001015 abdomen Anatomy 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 210000004204 blood vessel Anatomy 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 210000002808 connective tissue Anatomy 0.000 claims description 2
- 238000005520 cutting process Methods 0.000 claims description 2
- 239000003651 drinking water Substances 0.000 claims description 2
- 235000020188 drinking water Nutrition 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 230000027119 gastric acid secretion Effects 0.000 claims description 2
- 239000007903 gelatin capsule Substances 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 239000007928 intraperitoneal injection Substances 0.000 claims description 2
- 238000010253 intravenous injection Methods 0.000 claims description 2
- 210000004731 jugular vein Anatomy 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
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- 238000005303 weighing Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims 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
- 241000510672 Cuminum Species 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
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- 239000000377 silicon dioxide Substances 0.000 description 28
- 229910021529 ammonia Inorganic materials 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 150000004985 diamines Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
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- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 2
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- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AMBKPYJJYUKNFI-UHFFFAOYSA-N methylsulfanylethene Chemical group CSC=C AMBKPYJJYUKNFI-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- BEAVGOPNGFVGBG-UHFFFAOYSA-N n-[bis(methylsulfanyl)methylidene]methanesulfonamide Chemical compound CSC(SC)=NS(C)(=O)=O BEAVGOPNGFVGBG-UHFFFAOYSA-N 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003567 thiocyanates Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB20660/77A GB1604674A (en) | 1977-05-17 | 1977-05-17 | Aminoalkyl-benzene derivatives |
| ZA00782649A ZA782649B (en) | 1977-05-17 | 1978-05-09 | Pharmacologically active compounds |
| IE940/78A IE46886B1 (en) | 1977-05-17 | 1978-05-09 | Aminoalkyl-benzene derivatives |
| NZ187235A NZ187235A (en) | 1977-05-17 | 1978-05-10 | Aminoalkylbenzene derivatives and pharmaceutical compositions |
| FI781490A FI781490A7 (fi) | 1977-05-17 | 1978-05-11 | Farmakologiskt aktiva komponenter |
| AU36067/78A AU523496B2 (en) | 1977-05-17 | 1978-05-12 | Aminoalkyl benzene derivatives |
| BE187722A BE867106A (fr) | 1977-05-17 | 1978-05-16 | Nouveaux derives d'aminoalkylbenzenes et procede pour leur preparation |
| DK214878A DK214878A (da) | 1977-05-17 | 1978-05-16 | Fremgangsmaade til fremstilling af aminoalkylbenzenderivater |
| CH531578A CH643238A5 (en) | 1977-05-17 | 1978-05-16 | Aminoalkylbenzene derivatives having a selective action on histamine receptors |
| SE7805591A SE443558B (sv) | 1977-05-17 | 1978-05-16 | Forfarande for framstellning av aminoalkylbensenderivat med farmaceutisk verkan |
| DE19782821410 DE2821410A1 (de) | 1977-05-17 | 1978-05-16 | Aminoalkylbenzolderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen |
| JP5870678A JPS53149936A (en) | 1977-05-17 | 1978-05-17 | Novel aminoalkylbenzene derivative process for preparing same medical composition and application thereof |
| ES469953A ES469953A1 (es) | 1977-05-17 | 1978-05-17 | Un procedimiento para la preparacion de nuevos derivados de aminoalquilbenceno |
| FR7814594A FR2401135A1 (fr) | 1977-05-17 | 1978-05-17 | Nouveaux derives d'aminoalkyl-benzenes et procedes pour leur preparation |
| IT7849419A IT1156755B (it) | 1977-05-17 | 1978-05-17 | Derivati amminoalchilbenzenici utili come farmaceutici in particolare per la cura di ulcere gastriche e di allergie della pelle e relativo procedimento di produzione |
| NL7805344A NL7805344A (nl) | 1977-05-17 | 1978-05-17 | Aminoalkylbenzeenderivaten. |
| FR7828239A FR2398718A1 (fr) | 1977-05-17 | 1978-10-03 | Nouvelles amines primaires utiles a la preparation de derives d'aminoalkyl benzenes |
| AU84117/82A AU541144B2 (en) | 1977-05-17 | 1982-05-25 | Aminoalkylbenzene derivatives |
| CH749182A CH643233A5 (en) | 1977-05-17 | 1982-12-22 | Intermediates for the preparation of aminoalkylbenzene derivatives |
| JP61288643A JPS6354343A (ja) | 1977-05-17 | 1986-12-03 | アミノアルキルベンゼン誘導体 |
| US06/944,217 US5021429A (en) | 1977-05-17 | 1986-12-22 | Pharmacologically active aminoalkylphenyl compounds and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB20660/77A GB1604674A (en) | 1977-05-17 | 1977-05-17 | Aminoalkyl-benzene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1604674A true GB1604674A (en) | 1981-12-16 |
Family
ID=10149556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20660/77A Expired GB1604674A (en) | 1977-05-17 | 1977-05-17 | Aminoalkyl-benzene derivatives |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS6354343A (enrdf_load_stackoverflow) |
| BE (1) | BE867106A (enrdf_load_stackoverflow) |
| GB (1) | GB1604674A (enrdf_load_stackoverflow) |
| ZA (1) | ZA782649B (enrdf_load_stackoverflow) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0055179A1 (en) * | 1980-12-22 | 1982-06-30 | Merck & Co. Inc. | Aminoalkyl pyridine derivatives |
| FR2505835A1 (fr) * | 1981-05-18 | 1982-11-19 | Bristol Myers Co | Nouvelles 1,2-diaminocyclobutene-3,4-diones, leur procede de preparation et composition pharmaceutique les contenant |
| EP0066415A3 (en) * | 1981-05-20 | 1983-09-14 | A.H. Robins Company, Incorporated | N-(arylthioalkyl)-n'-(aminoalkyl)ureas |
| US4491586A (en) * | 1980-06-05 | 1985-01-01 | Glaxo Group Limited | Amine derivatives |
| 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 |
| EP0172968A1 (en) * | 1983-10-28 | 1986-03-05 | Smith Kline & French Laboratories Limited | Aminothiadiazine derivatives as histamine H2-antagonists |
| US4680300A (en) * | 1985-01-10 | 1987-07-14 | Syntex (U.S.A.) Inc. | Anti-inflammatory guanidines |
| US4767769A (en) * | 1984-07-05 | 1988-08-30 | The Boots Company Plc | Antiulcer benzimidazole derivatives |
| US4871765A (en) * | 1987-08-28 | 1989-10-03 | Toyama Chemical Co., Ltd. | Amine derivative and its salt and anti-ulcer agent containing the same |
| EP0302422A3 (en) * | 1987-08-03 | 1990-02-07 | Kyorin Pharmaceutical Co., Ltd. | Urea derivatives |
| FR2685323A1 (fr) * | 1991-12-19 | 1993-06-25 | Rhone Poulenc Chimie | Mercaptomethylbenzylamines et leur utilisation dans la synthese de bisphenols. |
| WO2001023350A1 (en) * | 1999-09-28 | 2001-04-05 | Nihon Nohyaku Co., Ltd. | Thioalkylamine derivatives and process for the preparation thereof |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4496567A (en) * | 1978-11-13 | 1985-01-29 | Smith Kline & French Laboratories Limited | Phenyl alkylaminopyrimidones |
| ZA801151B (en) * | 1979-03-02 | 1981-02-25 | Glaxo Group Ltd | Heterocyclic derivatives |
| JPS55120571A (en) * | 1979-03-02 | 1980-09-17 | Glaxo Group Ltd | Heterocyclic derivative |
| IE53068B1 (en) * | 1981-06-15 | 1988-05-25 | Merck & Co Inc | Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors |
| US4543352A (en) * | 1983-04-29 | 1985-09-24 | William H. Rorer, Inc. | Naphthalene aminoalkylene ethers and thioethers, and their pharmaceutical uses |
| US4567191A (en) * | 1983-06-07 | 1986-01-28 | Merck & Co., Inc. | Amino-phenyl-thiadiazoledioxides as gastric secretion inhibitors |
| JP2006212152A (ja) * | 2005-02-02 | 2006-08-17 | Itoki Corp | 椅子 |
-
1977
- 1977-05-17 GB GB20660/77A patent/GB1604674A/en not_active Expired
-
1978
- 1978-05-09 ZA ZA00782649A patent/ZA782649B/xx unknown
- 1978-05-16 BE BE187722A patent/BE867106A/xx not_active IP Right Cessation
-
1986
- 1986-12-03 JP JP61288643A patent/JPS6354343A/ja active Granted
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4491586A (en) * | 1980-06-05 | 1985-01-01 | Glaxo Group Limited | Amine derivatives |
| EP0055179A1 (en) * | 1980-12-22 | 1982-06-30 | Merck & Co. Inc. | Aminoalkyl pyridine derivatives |
| FR2505835A1 (fr) * | 1981-05-18 | 1982-11-19 | Bristol Myers Co | Nouvelles 1,2-diaminocyclobutene-3,4-diones, leur procede de preparation et composition pharmaceutique les contenant |
| FR2513250A1 (fr) * | 1981-05-18 | 1983-03-25 | Bristol Myers Co | Nouvelles cyclobutene-3,4-diones substituees |
| 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 |
| EP0066415A3 (en) * | 1981-05-20 | 1983-09-14 | A.H. Robins Company, Incorporated | N-(arylthioalkyl)-n'-(aminoalkyl)ureas |
| EP0172968A1 (en) * | 1983-10-28 | 1986-03-05 | Smith Kline & French Laboratories Limited | Aminothiadiazine derivatives as histamine H2-antagonists |
| AU572213B2 (en) * | 1983-10-28 | 1988-05-05 | Smith Kline & French Laboratories Limited | Substituted 1,2,4-thiadiazines |
| US4767769A (en) * | 1984-07-05 | 1988-08-30 | The Boots Company Plc | Antiulcer benzimidazole derivatives |
| US4680300A (en) * | 1985-01-10 | 1987-07-14 | Syntex (U.S.A.) Inc. | Anti-inflammatory guanidines |
| EP0302422A3 (en) * | 1987-08-03 | 1990-02-07 | Kyorin Pharmaceutical Co., Ltd. | Urea derivatives |
| US4871765A (en) * | 1987-08-28 | 1989-10-03 | Toyama Chemical Co., Ltd. | Amine derivative and its salt and anti-ulcer agent containing the same |
| FR2685323A1 (fr) * | 1991-12-19 | 1993-06-25 | Rhone Poulenc Chimie | Mercaptomethylbenzylamines et leur utilisation dans la synthese de bisphenols. |
| WO2001023350A1 (en) * | 1999-09-28 | 2001-04-05 | Nihon Nohyaku Co., Ltd. | Thioalkylamine derivatives and process for the preparation thereof |
| US6639109B1 (en) | 1999-09-28 | 2003-10-28 | Nihon Nohyaku Co., Ltd. | Process for production of thioalkylamine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA782649B (en) | 1979-05-30 |
| JPH0153862B2 (enrdf_load_stackoverflow) | 1989-11-15 |
| BE867106A (fr) | 1978-11-16 |
| JPS6354343A (ja) | 1988-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940508 |