JPH06500994A - 抗うつ剤としての1−置換フェノキサチイン誘導体 - Google Patents
抗うつ剤としての1−置換フェノキサチイン誘導体Info
- Publication number
- JPH06500994A JPH06500994A JP3515263A JP51526391A JPH06500994A JP H06500994 A JPH06500994 A JP H06500994A JP 3515263 A JP3515263 A JP 3515263A JP 51526391 A JP51526391 A JP 51526391A JP H06500994 A JPH06500994 A JP H06500994A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- dioxide
- phenoxathiin
- hydroxyethyl
- formulation
- 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.)
- Pending
Links
- 239000000935 antidepressant agent Substances 0.000 title claims description 4
- 229940005513 antidepressants Drugs 0.000 title claims description 4
- -1 1-Substituted phenoxathiin Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 43
- 102000010909 Monoamine Oxidase Human genes 0.000 claims description 23
- 108010062431 Monoamine oxidase Proteins 0.000 claims description 23
- 238000009472 formulation Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 230000005764 inhibitory process Effects 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- SKTDSCHBBJQCDE-UHFFFAOYSA-N 1-phenoxathiin-1-ylethanol Chemical compound O1C2=CC=CC=C2SC2=C1C=CC=C2C(O)C SKTDSCHBBJQCDE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 241000282412 Homo Species 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- ZETFADRORWAXBD-UHFFFAOYSA-N 1-(10,10-dioxophenoxathiin-1-yl)ethanol Chemical compound O1C2=CC=CC=C2S(=O)(=O)C2=C1C=CC=C2C(O)C ZETFADRORWAXBD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- PKTQHXZCHYIMFP-UHFFFAOYSA-N 1-(10,10-dioxophenoxathiin-1-yl)ethane-1,2-diol Chemical compound O1C2=CC=CC=C2S(=O)(=O)C2=C1C=CC=C2C(O)CO PKTQHXZCHYIMFP-UHFFFAOYSA-N 0.000 claims description 3
- AVCGPZJJCGYEDQ-UHFFFAOYSA-N 1-phenoxathiin-1-ylethane-1,2-diol Chemical compound O1C2=CC=CC=C2SC2=C1C=CC=C2C(O)CO AVCGPZJJCGYEDQ-UHFFFAOYSA-N 0.000 claims description 3
- 230000001430 anti-depressive effect Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- XJLRCPYQIPAQCA-UHFFFAOYSA-N phenoxathiine 10,10-dioxide Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3OC2=C1 XJLRCPYQIPAQCA-UHFFFAOYSA-N 0.000 claims description 3
- UALGAWZECPBKOD-UHFFFAOYSA-N 1-(10,10-dioxophenoxathiin-1-yl)ethanone Chemical compound O1C2=CC=CC=C2S(=O)(=O)C2=C1C=CC=C2C(=O)C UALGAWZECPBKOD-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
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- 241000124008 Mammalia Species 0.000 claims 7
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- OKEITXXEAYZCOA-UHFFFAOYSA-N 1-ethenylphenoxathiine 10,10-dioxide Chemical compound O1C2=CC=CC=C2S(=O)(=O)C2=C1C=CC=C2C=C OKEITXXEAYZCOA-UHFFFAOYSA-N 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- FVPFHLLCMSZVDO-UHFFFAOYSA-N 2-phenoxathiin-1-ylethanol Chemical compound O1C2=CC=CC=C2SC2=C1C=CC=C2CCO FVPFHLLCMSZVDO-UHFFFAOYSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 28
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
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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 14
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
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- 238000003556 assay Methods 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229940076279 serotonin Drugs 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 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
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 4
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
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- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000007919 dispersible tablet Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000013038 irreversible inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940080428 lactose 200 mg Drugs 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- QEHKBHWEUPXBCW-UHFFFAOYSA-N nitrogen trichloride Chemical compound ClN(Cl)Cl QEHKBHWEUPXBCW-UHFFFAOYSA-N 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 208000022821 personality disease Diseases 0.000 description 1
- 208000019899 phobic disease Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000013037 reversible inhibitor Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 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
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/39—Heterocyclic compounds having sulfur as a ring hetero atom having oxygen in the same ring
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58391690A | 1990-09-17 | 1990-09-17 | |
| US583,916 | 1990-09-17 | ||
| GB919118955A GB9118955D0 (en) | 1991-09-05 | 1991-09-05 | Pharmacologically active compounds |
| GB9118955.5 | 1991-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06500994A true JPH06500994A (ja) | 1994-01-27 |
Family
ID=26299495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3515263A Pending JPH06500994A (ja) | 1990-09-17 | 1991-09-16 | 抗うつ剤としての1−置換フェノキサチイン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0550518A1 (fr) |
| JP (1) | JPH06500994A (fr) |
| KR (1) | KR930701997A (fr) |
| AU (1) | AU8635691A (fr) |
| CA (1) | CA2091685A1 (fr) |
| IE (1) | IE913256A1 (fr) |
| IL (1) | IL99494A0 (fr) |
| PT (1) | PT98982A (fr) |
| WO (1) | WO1992004897A1 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2265943A1 (fr) * | 1996-09-11 | 1998-03-26 | Morton Harfenist | Composes constituant pharmacologiquement des principes actifs et leur utilisation |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1447032A (en) * | 1972-05-19 | 1976-08-25 | Wellcome Found | Tricyclic sulphones and pharmaceutical compositions containing them |
| US4012517A (en) * | 1975-01-24 | 1977-03-15 | Burroughs Wellcome Co. | Compositions and treatment |
| EP0150891A1 (fr) * | 1984-01-05 | 1985-08-07 | The Wellcome Foundation Limited | Composés tricycliques, procédés pour leur préparation, compositions les contenant et leur usage en médecine |
| GB8921069D0 (en) * | 1989-09-18 | 1989-11-01 | Wellcome Found | Pharmaceutically active compound,preparation and use |
-
1991
- 1991-09-16 KR KR1019930700784A patent/KR930701997A/ko not_active Withdrawn
- 1991-09-16 CA CA002091685A patent/CA2091685A1/fr not_active Abandoned
- 1991-09-16 AU AU86356/91A patent/AU8635691A/en not_active Abandoned
- 1991-09-16 JP JP3515263A patent/JPH06500994A/ja active Pending
- 1991-09-16 PT PT98982A patent/PT98982A/pt not_active Application Discontinuation
- 1991-09-16 IE IE325691A patent/IE913256A1/en unknown
- 1991-09-16 EP EP91916647A patent/EP0550518A1/fr not_active Withdrawn
- 1991-09-16 IL IL99494A patent/IL99494A0/xx unknown
- 1991-09-16 WO PCT/GB1991/001582 patent/WO1992004897A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR930701997A (ko) | 1993-09-08 |
| AU8635691A (en) | 1992-04-15 |
| IE913256A1 (en) | 1992-02-25 |
| CA2091685A1 (fr) | 1992-03-18 |
| EP0550518A1 (fr) | 1993-07-14 |
| WO1992004897A1 (fr) | 1992-04-02 |
| IL99494A0 (en) | 1992-08-18 |
| PT98982A (pt) | 1993-11-30 |
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