JPS58109487A - 新規ジアザシクロヘプタフルオレン誘導体 - Google Patents
新規ジアザシクロヘプタフルオレン誘導体Info
- Publication number
- JPS58109487A JPS58109487A JP57213239A JP21323982A JPS58109487A JP S58109487 A JPS58109487 A JP S58109487A JP 57213239 A JP57213239 A JP 57213239A JP 21323982 A JP21323982 A JP 21323982A JP S58109487 A JPS58109487 A JP S58109487A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- methyl
- formula
- pharmaceutically acceptable
- general formula
- 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
- BSQRLAHVEHKDMA-UHFFFAOYSA-N 3,4-diazatetracyclo[9.7.0.02,8.012,17]octadeca-1(18),2,4,6,8,10,12,14,16-nonaene Chemical class N1=NC=CC=C2C=CC3=C4C=CC=CC4=CC3=C21 BSQRLAHVEHKDMA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 238000007792 addition Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 5
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- -1 fluorene compound Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 230000007812 deficiency Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 241000218645 Cedrus Species 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- 230000001458 anti-acid effect Effects 0.000 claims 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000006264 debenzylation reaction Methods 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229940001470 psychoactive drug Drugs 0.000 claims 1
- 239000004089 psychotropic agent Substances 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000496 anti-anoxic effect Effects 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000004083 survival effect Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- 235000002568 Capsicum frutescens Nutrition 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000032274 Encephalopathy Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 231100000871 behavioral problem Toxicity 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000012046 side dish Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Revetment (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Non-Reversible Transmitting Devices (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8122643 | 1981-12-03 | ||
| FR8122643A FR2517679A1 (fr) | 1981-12-03 | 1981-12-03 | Derives de diaza-3,7a cyclohepta (j,k) fluorenes, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58109487A true JPS58109487A (ja) | 1983-06-29 |
Family
ID=9264634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57213239A Pending JPS58109487A (ja) | 1981-12-03 | 1982-12-03 | 新規ジアザシクロヘプタフルオレン誘導体 |
Country Status (18)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4665183A (en) * | 1985-12-20 | 1987-05-12 | American Home Products Corp. | Process for preparing 6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-amines and derivatives thereof useful for the treatment of cognitive impairments |
| US4624954A (en) * | 1985-12-20 | 1986-11-25 | American Home Products Corporation | 6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-amines and derivatives thereof, useful for the treatment of cognitive impairments |
| CA2027814C (en) * | 1989-10-20 | 1996-07-30 | Ryuji Ueno | Treatment of hepatobiliary disease with 15-keto-prostaglandin compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD129791A5 (de) * | 1976-04-13 | 1978-02-08 | Synthelabo | Verfahren zur herstellung von naphtyridinderivaten |
| US4228168A (en) * | 1978-11-22 | 1980-10-14 | Tanabe Seiyaku Co., Ltd. | Azepino [1,2,3-lm]-β-carboline compounds and pharmaceutical composition thereof |
| JPS55161389A (en) * | 1979-06-01 | 1980-12-15 | Ngk Spark Plug Co | Method of connecting porcelain insulator to fitting |
-
1981
- 1981-12-03 FR FR8122643A patent/FR2517679A1/fr active Granted
-
1982
- 1982-11-29 AT AT82402172T patent/ATE17485T1/de active
- 1982-11-29 EP EP82402172A patent/EP0082040B1/fr not_active Expired
- 1982-11-29 DE DE8282402172T patent/DE3268605D1/de not_active Expired
- 1982-12-02 FI FI824155A patent/FI71321C/fi not_active IP Right Cessation
- 1982-12-02 HU HU828374A patent/HU186180B/hu unknown
- 1982-12-02 GR GR69964A patent/GR77848B/el unknown
- 1982-12-02 US US06/446,368 patent/US4503058A/en not_active Expired - Fee Related
- 1982-12-02 ZA ZA828877A patent/ZA828877B/xx unknown
- 1982-12-02 DK DK535082A patent/DK535082A/da not_active Application Discontinuation
- 1982-12-02 CA CA000416847A patent/CA1196329A/en not_active Expired
- 1982-12-02 ES ES517874A patent/ES517874A0/es active Granted
- 1982-12-02 NO NO824040A patent/NO824040L/no unknown
- 1982-12-02 NZ NZ202688A patent/NZ202688A/en unknown
- 1982-12-02 PT PT75925A patent/PT75925B/pt unknown
- 1982-12-02 IL IL67400A patent/IL67400A/xx unknown
- 1982-12-02 AU AU91076/82A patent/AU553493B2/en not_active Ceased
- 1982-12-03 JP JP57213239A patent/JPS58109487A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU553493B2 (en) | 1986-07-17 |
| NO824040L (no) | 1983-06-06 |
| FI824155L (fi) | 1983-06-04 |
| FI71321C (fi) | 1986-12-19 |
| CA1196329A (en) | 1985-11-05 |
| FR2517679B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-01-27 |
| HU186180B (en) | 1985-06-28 |
| DE3268605D1 (en) | 1986-02-27 |
| GR77848B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-09-25 |
| ZA828877B (en) | 1983-09-28 |
| FI824155A0 (fi) | 1982-12-02 |
| IL67400A0 (en) | 1983-05-15 |
| EP0082040A1 (fr) | 1983-06-22 |
| AU9107682A (en) | 1983-06-09 |
| EP0082040B1 (fr) | 1986-01-15 |
| ES8401488A1 (es) | 1983-12-01 |
| FI71321B (fi) | 1986-09-09 |
| IL67400A (en) | 1985-07-31 |
| NZ202688A (en) | 1985-01-31 |
| US4503058A (en) | 1985-03-05 |
| ES517874A0 (es) | 1983-12-01 |
| PT75925B (fr) | 1985-12-20 |
| FR2517679A1 (fr) | 1983-06-10 |
| DK535082A (da) | 1983-06-04 |
| PT75925A (fr) | 1983-01-01 |
| ATE17485T1 (de) | 1986-02-15 |
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