HU204503B - Process for producing aminopropanol derivatives of 3-(2-hydroxy-phenyl)-1-propanols and pharmaceutical compositions containing them - Google Patents
Process for producing aminopropanol derivatives of 3-(2-hydroxy-phenyl)-1-propanols and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HU204503B HU204503B HU883184A HU318488A HU204503B HU 204503 B HU204503 B HU 204503B HU 883184 A HU883184 A HU 883184A HU 318488 A HU318488 A HU 318488A HU 204503 B HU204503 B HU 204503B
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- hydroxy
- propoxy
- preparation
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- -1 t-pentylamino Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- XSQWRASDDDYZMF-UHFFFAOYSA-N 3-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-1-phenylpropan-1-one;hydrochloride Chemical compound Cl.C1CCCCN1CC(O)COC1=CC=CC=C1CCC(=O)C1=CC=CC=C1 XSQWRASDDDYZMF-UHFFFAOYSA-N 0.000 claims description 3
- IBACJUCXNPOKEU-UHFFFAOYSA-N 3-[2-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-1-(3-methoxyphenyl)propan-1-one;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=O)CCC=2C(=CC=CC=2)OCC(O)CNC(C)C)=C1 IBACJUCXNPOKEU-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- AGRUZMINWHAACD-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]propan-1-one;hydrochloride Chemical compound Cl.CCCNCC(O)COC1=CC=CC=C1CCC(=O)C1=CC=C(OC)C(OC)=C1 AGRUZMINWHAACD-UHFFFAOYSA-N 0.000 claims description 2
- GVJHMXWXZBNGRQ-UHFFFAOYSA-N 3-(2-hydroxyphenyl)propanal Chemical class OC1=CC=CC=C1CCC=O GVJHMXWXZBNGRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000003826 tablet Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 239000008298 dragée Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000003288 anthiarrhythmic effect Effects 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method 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
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000829 suppository Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000007941 film coated tablet Substances 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 4
- 229960000203 propafenone Drugs 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 206010003119 arrhythmia Diseases 0.000 description 3
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229940031705 hydroxypropyl methylcellulose 2910 Drugs 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229960003511 macrogol Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229960004793 sucrose Drugs 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 235000010215 titanium dioxide Nutrition 0.000 description 3
- JCPGMXJLFWGRMZ-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-3-phenylpropan-1-one Chemical compound OC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JCPGMXJLFWGRMZ-UHFFFAOYSA-N 0.000 description 2
- NAEHOJHEJJZFFE-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[2-(oxiran-2-ylmethoxy)phenyl]propan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)CCC1=CC=CC=C1OCC1OC1 NAEHOJHEJJZFFE-UHFFFAOYSA-N 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
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- 241000282472 Canis lupus familiaris Species 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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- VDKMYSMWQCFYBQ-UHFFFAOYSA-N diprafenone Chemical compound CCC(C)(C)NCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 VDKMYSMWQCFYBQ-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
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same 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
- C07D295/084—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP87109015A EP0296264A1 (de) | 1987-06-23 | 1987-06-23 | Aminopropanolderivate von 3-(2-Hydroxyphenyl)-1-propanonderivaten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT51234A HUT51234A (en) | 1990-04-28 |
| HU204503B true HU204503B (en) | 1992-01-28 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU883184A HU204503B (en) | 1987-06-23 | 1988-06-22 | Process for producing aminopropanol derivatives of 3-(2-hydroxy-phenyl)-1-propanols and pharmaceutical compositions containing them |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0296264A1 (en, 2012) |
| JP (1) | JPS6426540A (en, 2012) |
| KR (1) | KR890000400A (en, 2012) |
| AU (1) | AU606692B2 (en, 2012) |
| DD (1) | DD271701A5 (en, 2012) |
| DE (2) | DE3868357D1 (en, 2012) |
| DK (1) | DK342188A (en, 2012) |
| ES (1) | ES2019857T3 (en, 2012) |
| FI (1) | FI883002A7 (en, 2012) |
| GR (2) | GR890300035T1 (en, 2012) |
| HU (1) | HU204503B (en, 2012) |
| IL (1) | IL86812A (en, 2012) |
| NO (1) | NO167974C (en, 2012) |
| PT (1) | PT87792B (en, 2012) |
| SU (1) | SU1628855A3 (en, 2012) |
| YU (1) | YU119988A (en, 2012) |
| ZA (1) | ZA884436B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4426245A1 (de) * | 1994-07-23 | 1996-02-22 | Gruenenthal Gmbh | 1-Phenyl-3-dimethylamino-propanverbindungen mit pharmakologischer Wirkung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT66890B (fr) * | 1976-08-21 | 1979-01-25 | Hexachimie | Procede pour la preparation des aryloxy-1 amino-3 propanol-2 |
| DE3226863A1 (de) * | 1981-09-18 | 1983-04-07 | Basf Ag, 6700 Ludwigshafen | Aminopropanolderivate von 2-hydroxy-ss-phenyl-propiophenonen, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| US4540697A (en) * | 1982-09-09 | 1985-09-10 | Basf Aktiengesellschaft | Aminopropanol derivatives of 2-hydroxy-β-phenyl-propiophenones, pharmaceutical compositions and use |
| EP0283540B1 (de) * | 1987-03-26 | 1991-09-18 | Helopharm W. Petrik GmbH & Co.KG. | Verfahren zur Herstellung von 5-Hydroxydiprafenon und seiner Salze mit Säuren |
-
1987
- 1987-06-23 EP EP87109015A patent/EP0296264A1/de not_active Withdrawn
-
1988
- 1988-06-20 KR KR1019880007412A patent/KR890000400A/ko not_active Abandoned
- 1988-06-21 IL IL86812A patent/IL86812A/xx unknown
- 1988-06-22 SU SU884356029A patent/SU1628855A3/ru active
- 1988-06-22 DK DK342188A patent/DK342188A/da unknown
- 1988-06-22 DD DD88317033A patent/DD271701A5/de not_active IP Right Cessation
- 1988-06-22 YU YU01199/88A patent/YU119988A/xx unknown
- 1988-06-22 HU HU883184A patent/HU204503B/hu not_active IP Right Cessation
- 1988-06-22 ZA ZA884436A patent/ZA884436B/xx unknown
- 1988-06-22 PT PT87792A patent/PT87792B/pt not_active IP Right Cessation
- 1988-06-22 FI FI883002A patent/FI883002A7/fi not_active IP Right Cessation
- 1988-06-22 AU AU18241/88A patent/AU606692B2/en not_active Ceased
- 1988-06-22 JP JP63154576A patent/JPS6426540A/ja active Granted
- 1988-06-22 NO NO882770A patent/NO167974C/no unknown
- 1988-06-23 DE DE8888110033T patent/DE3868357D1/de not_active Expired - Fee Related
- 1988-06-23 ES ES198888110033T patent/ES2019857T3/es not_active Expired - Lifetime
- 1988-06-23 DE DE3821259A patent/DE3821259A1/de not_active Withdrawn
-
1989
- 1989-04-12 GR GR89300035T patent/GR890300035T1/el unknown
-
1992
- 1992-04-28 GR GR920400818T patent/GR3004456T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU119988A (en) | 1989-12-31 |
| PT87792A (pt) | 1988-07-01 |
| SU1628855A3 (ru) | 1991-02-15 |
| JPS6426540A (en) | 1989-01-27 |
| DE3868357D1 (de) | 1992-03-26 |
| PT87792B (pt) | 1992-10-30 |
| IL86812A (en) | 1991-12-15 |
| NO167974C (no) | 1992-01-02 |
| NO882770D0 (no) | 1988-06-22 |
| ES2019857A4 (es) | 1991-07-16 |
| AU606692B2 (en) | 1991-02-14 |
| KR890000400A (ko) | 1989-03-14 |
| IL86812A0 (en) | 1988-11-30 |
| HUT51234A (en) | 1990-04-28 |
| FI883002A7 (fi) | 1988-12-24 |
| EP0296264A1 (de) | 1988-12-28 |
| ES2019857T3 (es) | 1993-09-16 |
| GR3004456T3 (en, 2012) | 1993-03-31 |
| NO167974B (no) | 1991-09-23 |
| FI883002A0 (fi) | 1988-06-22 |
| AU1824188A (en) | 1989-01-05 |
| NO882770L (no) | 1988-12-27 |
| GR890300035T1 (en) | 1989-04-12 |
| ZA884436B (en) | 1989-03-29 |
| DD271701A5 (de) | 1989-09-13 |
| DK342188D0 (da) | 1988-06-22 |
| DK342188A (da) | 1988-12-24 |
| JPH0320382B2 (en, 2012) | 1991-03-19 |
| DE3821259A1 (de) | 1989-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |