JPS6033424B2 - フェニルエチルアミンの誘導体、その製造方法およびフェニルエチルアミンの誘導体を有効成分とする高血圧および心臓血管病の治療薬 - Google Patents
フェニルエチルアミンの誘導体、その製造方法およびフェニルエチルアミンの誘導体を有効成分とする高血圧および心臓血管病の治療薬Info
- Publication number
- JPS6033424B2 JPS6033424B2 JP55059847A JP5984780A JPS6033424B2 JP S6033424 B2 JPS6033424 B2 JP S6033424B2 JP 55059847 A JP55059847 A JP 55059847A JP 5984780 A JP5984780 A JP 5984780A JP S6033424 B2 JPS6033424 B2 JP S6033424B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- alkyl group
- branched
- chain
- 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
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- 238000004519 manufacturing process Methods 0.000 title claims description 9
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- 208000024172 Cardiovascular disease Diseases 0.000 title claims description 3
- 229940124597 therapeutic agent Drugs 0.000 title claims 4
- 239000004480 active ingredient Substances 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- -1 methylenedioxy group Chemical group 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 36
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- 125000003545 alkoxy group Chemical group 0.000 claims description 15
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- 125000005843 halogen group Chemical group 0.000 claims description 11
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- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 6
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 5
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- QOBAXXQQFJJPAA-UHFFFAOYSA-N 1-(butylamino)propan-2-ol Chemical compound CCCCNCC(C)O QOBAXXQQFJJPAA-UHFFFAOYSA-N 0.000 claims description 3
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- 238000002360 preparation method Methods 0.000 claims description 3
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
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- 238000006243 chemical reaction Methods 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 239000000047 product Substances 0.000 description 49
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 230000000694 effects Effects 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- 238000012360 testing method Methods 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 150000001412 amines Chemical class 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 13
- 230000005764 inhibitory process Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 229960004592 isopropanol Drugs 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 229960001138 acetylsalicylic acid Drugs 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 5
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical group NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
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- 238000000921 elemental analysis Methods 0.000 description 5
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- 150000003141 primary amines Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 5
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
-
- 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
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- 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
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- 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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
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- 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
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- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU81225 | 1979-05-04 | ||
| LU81225 | 1979-05-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5663946A JPS5663946A (en) | 1981-05-30 |
| JPS6033424B2 true JPS6033424B2 (ja) | 1985-08-02 |
Family
ID=19729148
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55059847A Expired JPS6033424B2 (ja) | 1979-05-04 | 1980-05-06 | フェニルエチルアミンの誘導体、その製造方法およびフェニルエチルアミンの誘導体を有効成分とする高血圧および心臓血管病の治療薬 |
| JP5984680A Pending JPS565465A (en) | 1979-05-04 | 1980-05-06 | Benzimidazole derivative* its manufacture and medicinal composition of same as active component |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5984680A Pending JPS565465A (en) | 1979-05-04 | 1980-05-06 | Benzimidazole derivative* its manufacture and medicinal composition of same as active component |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4338330A (enExample) |
| JP (2) | JPS6033424B2 (enExample) |
| AT (2) | AT376210B (enExample) |
| AU (2) | AU537573B2 (enExample) |
| BE (2) | BE883069A (enExample) |
| CA (1) | CA1146563A (enExample) |
| CH (2) | CH644599A5 (enExample) |
| DE (2) | DE3016828A1 (enExample) |
| DK (2) | DK187980A (enExample) |
| ES (2) | ES491142A0 (enExample) |
| FI (2) | FI801429A7 (enExample) |
| FR (2) | FR2455572B1 (enExample) |
| GB (2) | GB2055091B (enExample) |
| GR (2) | GR68535B (enExample) |
| IE (1) | IE50218B1 (enExample) |
| IL (2) | IL59973A (enExample) |
| IT (2) | IT1159060B (enExample) |
| NL (2) | NL8002567A (enExample) |
| NO (2) | NO801286L (enExample) |
| PT (2) | PT71175A (enExample) |
| SE (2) | SE8003277L (enExample) |
| ZA (2) | ZA802695B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1156661A (en) * | 1980-02-25 | 1983-11-08 | Hoffmann-La Roche Limited | Phenoxy-aminopropanol derivatives |
| JPS582343A (ja) * | 1981-06-30 | 1983-01-07 | Osaka Soda Co Ltd | 耐窒素酸化物性に優れた加硫性ゴム組成物 |
| GB8310556D0 (en) * | 1983-04-19 | 1983-05-25 | Beecham Group Plc | Compounds |
| US4550119A (en) * | 1983-05-23 | 1985-10-29 | Warner-Lambert Company | 2,4-Dihydro-5-[(substituted)phenyl]-4,4-disubstituted-3H-pyrazol-3-ones |
| US5104892A (en) * | 1989-12-11 | 1992-04-14 | American Home Products Corporation | Substituted benzimidazole derivatives possessing Class III antiarrhythmic activity |
| US5541204A (en) * | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| EP1487843A4 (en) | 2002-03-20 | 2010-03-10 | Metabolex Inc | SUBSTITUTED PHENYLACETIC ACIDS |
| US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
| US7199259B2 (en) * | 2003-06-20 | 2007-04-03 | Metabolex, Inc. | Resolution of α-(phenoxy)phenylacetic acid derivatives |
| WO2005115383A2 (en) * | 2004-05-25 | 2005-12-08 | Metabolex, Inc. | Substituted triazoles as modulators of ppar and methods of their preparation |
| US20060014785A1 (en) * | 2004-05-25 | 2006-01-19 | Metabolex, Inc. | Bicyclic, substituted triazoles as modulators of ppar and methods of their preparation |
| US7714131B2 (en) * | 2005-09-23 | 2010-05-11 | Metabolex, Inc. | Process for the stereoselective preparation of (−)-halofenate and derivatives thereof |
| EP2727911B1 (en) * | 2012-10-31 | 2016-12-21 | Medizinische Hochschule Hannover | Novel means and methods for treating malaria and other parasitic disorders |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1157556A (en) * | 1966-06-09 | 1969-07-09 | Egyt Gyogyszervegyeszeti Gyar | Novel Benzazole Derivatives and the Preparation thereof |
| FR1570892A (enExample) * | 1968-06-18 | 1969-06-13 | ||
| US3574218A (en) * | 1969-08-11 | 1971-04-06 | Egyt Gyogyszervegyeszeti Gyar | 2-aryl- or aralkyl-substituted benzazole derivatives |
| JPS5231858B1 (enExample) * | 1969-12-17 | 1977-08-17 | ||
| CH624395A5 (enExample) | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag | |
| DE2609645A1 (de) | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
| DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
| DE2644833A1 (de) * | 1976-10-05 | 1978-04-20 | Boehringer Sohn Ingelheim | Neue 1-aryloxy-2-hydroxy-3-alkylenaminopropane und verfahren zu ihrer herstellung |
| DE2737630A1 (de) | 1977-08-20 | 1979-03-01 | Boehringer Mannheim Gmbh | Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE2801953A1 (de) | 1978-01-18 | 1979-07-19 | Boehringer Mannheim Gmbh | 4-hydroxy-2-benzimidazolinon-derivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| DE2801980A1 (de) | 1978-01-18 | 1979-07-19 | Boehringer Mannheim Gmbh | 4-hydroxy-2-benzimidazolin-thion- derivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
| EP0003758A1 (de) | 1978-02-09 | 1979-09-05 | Ciba-Geigy Ag | Verätherte Hydroxy-benzodiheterocyclen und ihre Säureadditionssalze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate |
| DE2905877A1 (de) | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE2905876A1 (de) | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | Neue piperidinopropylderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1980
- 1980-04-30 SE SE8003277A patent/SE8003277L/xx not_active Application Discontinuation
- 1980-04-30 US US06/145,144 patent/US4338330A/en not_active Expired - Lifetime
- 1980-04-30 DK DK187980A patent/DK187980A/da not_active Application Discontinuation
- 1980-04-30 DK DK187880A patent/DK187880A/da not_active Application Discontinuation
- 1980-04-30 SE SE8003278A patent/SE8003278L/xx not_active Application Discontinuation
- 1980-04-30 PT PT71175A patent/PT71175A/pt unknown
- 1980-04-30 BE BE0/200433A patent/BE883069A/fr not_active IP Right Cessation
- 1980-04-30 FR FR8009846A patent/FR2455572B1/fr not_active Expired
- 1980-04-30 FR FR8009847A patent/FR2455587A1/fr active Granted
- 1980-04-30 PT PT71174A patent/PT71174A/pt unknown
- 1980-04-30 BE BE0/200432A patent/BE883068A/fr not_active IP Right Cessation
- 1980-05-01 IL IL59973A patent/IL59973A/xx unknown
- 1980-05-01 IL IL59974A patent/IL59974A0/xx unknown
- 1980-05-02 GB GB8014645A patent/GB2055091B/en not_active Expired
- 1980-05-02 GR GR61835A patent/GR68535B/el unknown
- 1980-05-02 NO NO801286A patent/NO801286L/no unknown
- 1980-05-02 NL NL8002567A patent/NL8002567A/nl not_active Application Discontinuation
- 1980-05-02 CH CH345380A patent/CH644599A5/fr not_active IP Right Cessation
- 1980-05-02 GB GB8014647A patent/GB2055360B/en not_active Expired
- 1980-05-02 DE DE19803016828 patent/DE3016828A1/de not_active Withdrawn
- 1980-05-02 CH CH345280A patent/CH645090A5/fr not_active IP Right Cessation
- 1980-05-02 GR GR61836A patent/GR68536B/el unknown
- 1980-05-02 IT IT8021780A patent/IT1159060B/it active
- 1980-05-02 FI FI801429A patent/FI801429A7/fi not_active Application Discontinuation
- 1980-05-02 CA CA000351169A patent/CA1146563A/en not_active Expired
- 1980-05-02 FI FI801428A patent/FI801428A7/fi not_active Application Discontinuation
- 1980-05-02 IT IT8021779A patent/IT1150018B/it active
- 1980-05-02 DE DE19803016827 patent/DE3016827A1/de not_active Withdrawn
- 1980-05-02 NL NL8002568A patent/NL8002568A/nl not_active Application Discontinuation
- 1980-05-02 ES ES491142A patent/ES491142A0/es active Granted
- 1980-05-02 NO NO801285A patent/NO150916C/no unknown
- 1980-05-02 ES ES491143A patent/ES491143A0/es active Granted
- 1980-05-05 IE IE918/80A patent/IE50218B1/en unknown
- 1980-05-05 AT AT0238780A patent/AT376210B/de not_active IP Right Cessation
- 1980-05-05 AT AT0238680A patent/AT376418B/de not_active IP Right Cessation
- 1980-05-05 AU AU58095/80A patent/AU537573B2/en not_active Ceased
- 1980-05-05 ZA ZA00802695A patent/ZA802695B/xx unknown
- 1980-05-05 ZA ZA00802694A patent/ZA802694B/xx unknown
- 1980-05-05 AU AU58096/80A patent/AU542596B2/en not_active Ceased
- 1980-05-06 JP JP55059847A patent/JPS6033424B2/ja not_active Expired
- 1980-05-06 JP JP5984680A patent/JPS565465A/ja active Pending
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