HRP920925A2 - Aminopropanol derivatives of 3-(3-hydroxyphenyl)-1-propanone compounds, process for the preparation thereof; pharmaceutical compositions containing them - Google Patents
Aminopropanol derivatives of 3-(3-hydroxyphenyl)-1-propanone compounds, process for the preparation thereof; pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HRP920925A2 HRP920925A2 HR920925A HRP920925A HRP920925A2 HR P920925 A2 HRP920925 A2 HR P920925A2 HR 920925 A HR920925 A HR 920925A HR P920925 A HRP920925 A HR P920925A HR P920925 A2 HRP920925 A2 HR P920925A2
- Authority
- HR
- Croatia
- Prior art keywords
- hydroxy
- phenyl
- propanone
- propoxy
- methoxyphenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 22
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 11
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 28
- -1 benzene hydrocarbons Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000004292 cyclic ethers Chemical class 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 150000001983 dialkylethers Chemical class 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
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
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- 125000003118 aryl group Chemical group 0.000 claims 1
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
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- 238000000576 coating method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000004615 ingredient Substances 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
- 239000000829 suppository Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003416 antiarrhythmic agent Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 235000012222 talc Nutrition 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 244000215068 Acacia senegal Species 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
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- 229920002472 Starch Polymers 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000205 acacia gum Substances 0.000 description 4
- 235000010489 acacia gum Nutrition 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
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- 229940031705 hydroxypropyl methylcellulose 2910 Drugs 0.000 description 4
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- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- KPYOQGLZSGFUKM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-[2-hydroxy-3-(propan-2-ylamino)propoxy]-4-methoxyphenyl]propan-1-one;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1C(=O)CCC1=CC=C(OC)C(OCC(O)CNC(C)C)=C1 KPYOQGLZSGFUKM-UHFFFAOYSA-N 0.000 description 3
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- 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
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 239000000969 carrier Substances 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
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- DZMULNWWBSJCIS-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-(oxiran-2-ylmethoxy)phenyl]propan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)CCC1=CC=CC(OCC2OC2)=C1 DZMULNWWBSJCIS-UHFFFAOYSA-N 0.000 description 2
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- YXCDDBXEROLCLE-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-(2-hydroxy-3-morpholin-4-ylpropoxy)-4-methoxyphenyl]propan-1-one hydrochloride Chemical compound Cl.COC=1C=C(C=CC1OC)C(CCC1=CC(=C(C=C1)OC)OCC(CN1CCOCC1)O)=O YXCDDBXEROLCLE-UHFFFAOYSA-N 0.000 description 1
- WIYZLEZVKNGUOI-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]propan-1-one hydrochloride Chemical compound Cl.COC=1C=C(C=CC1OC)C(CCC1=CC(=CC=C1)OCC(CN1CCCCC1)O)=O WIYZLEZVKNGUOI-UHFFFAOYSA-N 0.000 description 1
- AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- WHSMCMZFALLCCD-UHFFFAOYSA-N 3-(3-hydroxy-4-methoxyphenyl)-1-naphthalen-2-ylpropan-1-one Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C1=CC=C(C=CC=C2)C2=C1 WHSMCMZFALLCCD-UHFFFAOYSA-N 0.000 description 1
- HYKZUSHZIXHJRZ-UHFFFAOYSA-N 3-[3-(2-hydroxy-3-morpholin-4-ylpropoxy)-4-methoxyphenyl]-1-(4-methylphenyl)propan-1-one hydrochloride Chemical compound Cl.CC1=CC=C(C=C1)C(CCC1=CC(=C(C=C1)OC)OCC(CN1CCOCC1)O)=O HYKZUSHZIXHJRZ-UHFFFAOYSA-N 0.000 description 1
- CSLQKMQMZYPZNE-UHFFFAOYSA-N 3-[3-(oxiran-2-ylmethoxy)phenyl]-1-(3,4,5-trimethoxyphenyl)propan-1-one Chemical compound COC=1C=C(C=C(C=1OC)OC)C(CCC1=CC(=CC=C1)OCC1CO1)=O CSLQKMQMZYPZNE-UHFFFAOYSA-N 0.000 description 1
- RHPPMSVWFMCSAL-UHFFFAOYSA-N 3-[3-(oxiran-2-ylmethoxy)phenyl]-1-phenanthren-3-ylpropan-1-one Chemical compound C=1C=C2C=CC3=CC=CC=C3C2=CC=1C(=O)CCC(C=1)=CC=CC=1OCC1CO1 RHPPMSVWFMCSAL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP87109016A EP0296265A1 (fr) | 1987-06-23 | 1987-06-23 | Dérivés aminopropanols de 3-(3-hydroxyphényl)-1-propanone, leur procédé de préparation et médicaments contenant ces composés |
| YU01200/88A YU120088A (en) | 1987-06-23 | 1988-06-22 | Process for obtaining aminopropanol derivatives of 3-(3-hydroxiphenyl)-1-propanonic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP920925A2 true HRP920925A2 (en) | 1994-08-31 |
Family
ID=8197085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR920925A HRP920925A2 (en) | 1987-06-23 | 1992-10-02 | Aminopropanol derivatives of 3-(3-hydroxyphenyl)-1-propanone compounds, process for the preparation thereof; pharmaceutical compositions containing them |
Country Status (20)
| Country | Link |
|---|---|
| EP (2) | EP0296265A1 (fr) |
| JP (1) | JPS6426541A (fr) |
| KR (1) | KR890000401A (fr) |
| AR (1) | AR246246A1 (fr) |
| AT (1) | ATE68479T1 (fr) |
| CA (1) | CA1331877C (fr) |
| DD (1) | DD271108A5 (fr) |
| DE (2) | DE3865547D1 (fr) |
| DK (1) | DK342288A (fr) |
| ES (1) | ES2008640T3 (fr) |
| FI (1) | FI92482C (fr) |
| GR (2) | GR890300050T1 (fr) |
| HR (1) | HRP920925A2 (fr) |
| HU (1) | HU204502B (fr) |
| IL (1) | IL86813A (fr) |
| NO (1) | NO167975C (fr) |
| PT (1) | PT87793B (fr) |
| SU (1) | SU1634135A3 (fr) |
| YU (1) | YU120088A (fr) |
| ZA (1) | ZA884437B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69425882T2 (de) * | 1993-03-29 | 2001-01-11 | Basf Ag | 1-amino-3-phenoxy-propan-derivate als modulatoren bei multi-drug resistenz |
| EP0814081A1 (fr) * | 1996-06-17 | 1997-12-29 | Eli Lilly And Company | Modulateurs résistants aux médicaments multiples |
Family Cites Families (3)
| 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 |
-
1987
- 1987-06-23 EP EP87109016A patent/EP0296265A1/fr not_active Withdrawn
-
1988
- 1988-06-21 IL IL86813A patent/IL86813A/xx not_active IP Right Cessation
- 1988-06-22 ZA ZA884437A patent/ZA884437B/xx unknown
- 1988-06-22 DD DD88317034A patent/DD271108A5/de not_active IP Right Cessation
- 1988-06-22 SU SU884355989A patent/SU1634135A3/ru active
- 1988-06-22 HU HU883183A patent/HU204502B/hu not_active IP Right Cessation
- 1988-06-22 CA CA000570097A patent/CA1331877C/fr not_active Expired - Fee Related
- 1988-06-22 AR AR88311194A patent/AR246246A1/es active
- 1988-06-22 NO NO882771A patent/NO167975C/no unknown
- 1988-06-22 JP JP63154577A patent/JPS6426541A/ja active Granted
- 1988-06-22 FI FI883001A patent/FI92482C/fi not_active IP Right Cessation
- 1988-06-22 YU YU01200/88A patent/YU120088A/xx unknown
- 1988-06-22 PT PT87793A patent/PT87793B/pt not_active IP Right Cessation
- 1988-06-22 DK DK342288A patent/DK342288A/da not_active Application Discontinuation
- 1988-06-22 KR KR1019880007508A patent/KR890000401A/ko not_active Application Discontinuation
- 1988-06-23 DE DE8888110034T patent/DE3865547D1/de not_active Expired - Fee Related
- 1988-06-23 AT AT88110034T patent/ATE68479T1/de active
- 1988-06-23 EP EP88110034A patent/EP0297435B1/fr not_active Expired - Lifetime
- 1988-06-23 ES ES198888110034T patent/ES2008640T3/es not_active Expired - Lifetime
- 1988-06-23 DE DE3821250A patent/DE3821250A1/de not_active Ceased
-
1989
- 1989-05-25 GR GR89300050T patent/GR890300050T1/el unknown
-
1991
- 1991-12-02 GR GR91401885T patent/GR3003257T3/el unknown
-
1992
- 1992-10-02 HR HR920925A patent/HRP920925A2/hr not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| ODBC | Application rejected |