CA1231970A - Dialkyl-amino-alkoxy-benzylalcohol derivatives, process for their preparation and pharmaceutical compositions containing them - Google Patents
Dialkyl-amino-alkoxy-benzylalcohol derivatives, process for their preparation and pharmaceutical compositions containing themInfo
- Publication number
- CA1231970A CA1231970A CA000444257A CA444257A CA1231970A CA 1231970 A CA1231970 A CA 1231970A CA 000444257 A CA000444257 A CA 000444257A CA 444257 A CA444257 A CA 444257A CA 1231970 A CA1231970 A CA 1231970A
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- ethyl
- benzylalcohol
- formula
- propylamino
- 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
- 238000000034 method Methods 0.000 title claims abstract description 37
- 230000008569 process Effects 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 150000002367 halogens Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 28
- 229960004217 benzyl alcohol Drugs 0.000 claims description 28
- -1 ethyl magnesium halide Chemical class 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- 239000000460 chlorine Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 238000007792 addition Methods 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical group 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 8
- 150000002902 organometallic compounds Chemical class 0.000 claims description 7
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 239000012965 benzophenone Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical class 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- UOMOSYFPKGQIKI-UHFFFAOYSA-N 1-(4-bromophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Br)C=C1 UOMOSYFPKGQIKI-UHFFFAOYSA-N 0.000 claims description 2
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 claims description 2
- FKXYUGSJUMXROI-UHFFFAOYSA-N 3-chloro-n,n-dipropylpropan-1-amine Chemical compound CCCN(CCC)CCCCl FKXYUGSJUMXROI-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229940031826 phenolate Drugs 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 7
- 239000007818 Grignard reagent Substances 0.000 claims 2
- 150000004795 grignard reagents Chemical class 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- QVKNQKFQMTYRJQ-UHFFFAOYSA-N 3-(4-bromophenoxy)-n,n-dipropylpropan-1-amine Chemical compound CCCN(CCC)CCCOC1=CC=C(Br)C=C1 QVKNQKFQMTYRJQ-UHFFFAOYSA-N 0.000 claims 1
- MXDPHLOVNAAXBH-UHFFFAOYSA-N [4-[3-(dipropylamino)propoxy]phenyl]-(4-fluorophenyl)methanone Chemical compound C1=CC(OCCCN(CCC)CCC)=CC=C1C(=O)C1=CC=C(F)C=C1 MXDPHLOVNAAXBH-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 18
- 230000001154 acute effect Effects 0.000 abstract description 4
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000009835 boiling Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 9
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 8
- 208000010513 Stupor Diseases 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
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- 229940068196 placebo Drugs 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 239000002775 capsule Substances 0.000 description 5
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- 239000008101 lactose Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000004201 L-cysteine Substances 0.000 description 4
- 235000013878 L-cysteine Nutrition 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 208000005392 Spasm Diseases 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
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- 239000012153 distilled water Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 230000006742 locomotor activity Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- JCMLRUNDSXARRW-UHFFFAOYSA-N trioxouranium Chemical compound O=[U](=O)=O JCMLRUNDSXARRW-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 150000004794 vinyl magnesium halides Chemical class 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU824192A HU187208B (en) | 1982-12-28 | 1982-12-28 | Process for production of new dialcil-amino-alcoxi-benzoalcohole derivates, their acid additional and quaterner soils and medical preparates consisting of them |
| HU4192/82 | 1982-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1231970A true CA1231970A (en) | 1988-01-26 |
Family
ID=10967277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000444257A Expired CA1231970A (en) | 1982-12-28 | 1983-12-23 | Dialkyl-amino-alkoxy-benzylalcohol derivatives, process for their preparation and pharmaceutical compositions containing them |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4645779A (en, 2012) |
| EP (1) | EP0114410B1 (en, 2012) |
| JP (1) | JPS59134756A (en, 2012) |
| AT (1) | ATE19772T1 (en, 2012) |
| AU (1) | AU558261B2 (en, 2012) |
| CA (1) | CA1231970A (en, 2012) |
| DE (1) | DE3363553D1 (en, 2012) |
| DK (1) | DK163182C (en, 2012) |
| ES (4) | ES8600205A1 (en, 2012) |
| FI (1) | FI78459C (en, 2012) |
| GR (1) | GR78771B (en, 2012) |
| HU (1) | HU187208B (en, 2012) |
| IL (1) | IL70560A (en, 2012) |
| ZA (1) | ZA839615B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014036655A1 (en) * | 2012-09-06 | 2014-03-13 | Mcpharma Biotech Inc. | Treatment of diarrhea and post-weaning diarrhea with resistant potato starch |
| WO2014089680A1 (en) | 2012-12-11 | 2014-06-19 | Nano Safe Coatings Incorporated (A Florida Corporation 3 P14000024914) | Uv cured benzophenone terminated quaternary ammonium antimicrobials for surfaces |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK368687A (da) * | 1986-11-21 | 1988-05-22 | Cheminova As | Aminoalkylerede hydroxyforbindelser og deres anvendelse som fungicider |
| CA2016738A1 (en) * | 1989-06-08 | 1990-12-08 | Philippe Guerry | Substituted aminoalkylbenzene derivatives |
| US5214046A (en) * | 1989-07-27 | 1993-05-25 | Hoffmann-La Roche Inc. | Substituted aminoalkoxybenzene anti-fungicidal compositions and use |
| CA2020888A1 (en) * | 1989-07-27 | 1991-01-28 | Philippe Guerry | Substituted aminoalkoxybenzene derivatives |
| GB9303210D0 (en) * | 1993-02-17 | 1993-03-31 | Univ Manitoba | Cancer treatment |
| CA2190699A1 (en) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Tertiary amines |
| EP1379493A2 (en) * | 2001-03-23 | 2004-01-14 | Eli Lilly and Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
| US7314937B2 (en) | 2002-03-21 | 2008-01-01 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine H3 receptor antagonists, preparation and therapeutic uses |
| US7858825B2 (en) * | 2007-02-15 | 2010-12-28 | Colorado State University Research Foundation | Acid and base stable diphenylmethanol derivatives and methods of use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075014A (en) * | 1960-06-14 | 1963-01-22 | Richardson Merrell Inc | Basic substituted alkoxy diphenylalkanols, diphenylalkenes and diphenylalkanes |
| US3494961A (en) * | 1965-03-12 | 1970-02-10 | Hoffmann La Roche | 1,4-bis-(p-(dialkylaminoalkoxy)aryl)-1,4-bis-(aryl)-2-b-1,4-diols |
| US4094908A (en) * | 1973-08-15 | 1978-06-13 | Richter Gedeon Vegyeszeti Gyar Rt. | Alpha-substituted benzhydrol derivatives |
| HU168432B (en, 2012) * | 1973-08-15 | 1976-04-28 |
-
1982
- 1982-12-28 HU HU824192A patent/HU187208B/hu not_active IP Right Cessation
-
1983
- 1983-12-23 AU AU22915/83A patent/AU558261B2/en not_active Ceased
- 1983-12-23 CA CA000444257A patent/CA1231970A/en not_active Expired
- 1983-12-27 IL IL70560A patent/IL70560A/xx unknown
- 1983-12-27 DK DK601683A patent/DK163182C/da active
- 1983-12-27 JP JP58244952A patent/JPS59134756A/ja active Granted
- 1983-12-27 FI FI834800A patent/FI78459C/fi not_active IP Right Cessation
- 1983-12-27 US US06/565,913 patent/US4645779A/en not_active Expired - Fee Related
- 1983-12-27 ES ES528462A patent/ES8600205A1/es not_active Expired
- 1983-12-27 ZA ZA839615A patent/ZA839615B/xx unknown
- 1983-12-28 AT AT83113177T patent/ATE19772T1/de not_active IP Right Cessation
- 1983-12-28 GR GR73369A patent/GR78771B/el unknown
- 1983-12-28 DE DE8383113177T patent/DE3363553D1/de not_active Expired
- 1983-12-28 EP EP83113177A patent/EP0114410B1/de not_active Expired
-
1985
- 1985-06-01 ES ES543803A patent/ES8604102A1/es not_active Expired
- 1985-06-01 ES ES543804A patent/ES8608476A1/es not_active Expired
- 1985-06-01 ES ES543805A patent/ES8604103A1/es not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014036655A1 (en) * | 2012-09-06 | 2014-03-13 | Mcpharma Biotech Inc. | Treatment of diarrhea and post-weaning diarrhea with resistant potato starch |
| WO2014089680A1 (en) | 2012-12-11 | 2014-06-19 | Nano Safe Coatings Incorporated (A Florida Corporation 3 P14000024914) | Uv cured benzophenone terminated quaternary ammonium antimicrobials for surfaces |
| US10961401B2 (en) | 2012-12-11 | 2021-03-30 | Nano Safe Coatings Incorporated | UV cured benzophenone terminated quaternary ammonium antimicrobials for surfaces |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8608476A1 (es) | 1986-07-16 |
| GR78771B (en, 2012) | 1984-10-02 |
| IL70560A (en) | 1986-12-31 |
| DE3363553D1 (en) | 1986-06-19 |
| FI78459B (fi) | 1989-04-28 |
| ES528462A0 (es) | 1985-10-01 |
| EP0114410B1 (de) | 1986-05-14 |
| DK163182B (da) | 1992-02-03 |
| ES8604102A1 (es) | 1986-01-16 |
| EP0114410A1 (de) | 1984-08-01 |
| FI834800L (fi) | 1984-06-29 |
| AU558261B2 (en) | 1987-01-22 |
| ATE19772T1 (de) | 1986-05-15 |
| DK163182C (da) | 1992-06-22 |
| ES543803A0 (es) | 1986-01-16 |
| HU187208B (en) | 1985-11-28 |
| ES543805A0 (es) | 1986-01-16 |
| JPS59134756A (ja) | 1984-08-02 |
| JPS6340780B2 (en, 2012) | 1988-08-12 |
| ES543804A0 (es) | 1986-07-16 |
| FI78459C (fi) | 1989-08-10 |
| FI834800A0 (fi) | 1983-12-27 |
| DK601683D0 (da) | 1983-12-27 |
| AU2291583A (en) | 1984-07-05 |
| US4645779A (en) | 1987-02-24 |
| ES8600205A1 (es) | 1985-10-01 |
| DK601683A (da) | 1984-06-29 |
| ES8604103A1 (es) | 1986-01-16 |
| IL70560A0 (en) | 1984-03-30 |
| ZA839615B (en) | 1984-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |