NO824040L - Fremgangsmaate for fremstilling av diaza-cykloheptafluorener - Google Patents
Fremgangsmaate for fremstilling av diaza-cykloheptafluorenerInfo
- Publication number
- NO824040L NO824040L NO824040A NO824040A NO824040L NO 824040 L NO824040 L NO 824040L NO 824040 A NO824040 A NO 824040A NO 824040 A NO824040 A NO 824040A NO 824040 L NO824040 L NO 824040L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- diaza
- compound
- fluorenes
- hydrogen atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000002220 fluorenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- -1 aluminium-lithium hydride Chemical compound 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 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 claims description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006264 debenzylation reaction Methods 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 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
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 206010002660 Anoxia Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 238000010171 animal model Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 208000026680 Metabolic Brain disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000003054 catalyst Substances 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 206010042772 syncope Diseases 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Revetment (AREA)
- Non-Reversible Transmitting Devices (AREA)
- Glass Compositions (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| NO824040L true NO824040L (no) | 1983-06-06 |
Family
ID=9264634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO824040A NO824040L (no) | 1981-12-03 | 1982-12-02 | Fremgangsmaate for fremstilling av diaza-cykloheptafluorener |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4503058A (el) |
| EP (1) | EP0082040B1 (el) |
| JP (1) | JPS58109487A (el) |
| AT (1) | ATE17485T1 (el) |
| AU (1) | AU553493B2 (el) |
| CA (1) | CA1196329A (el) |
| DE (1) | DE3268605D1 (el) |
| DK (1) | DK535082A (el) |
| ES (1) | ES517874A0 (el) |
| FI (1) | FI71321C (el) |
| FR (1) | FR2517679A1 (el) |
| GR (1) | GR77848B (el) |
| HU (1) | HU186180B (el) |
| IL (1) | IL67400A (el) |
| NO (1) | NO824040L (el) |
| NZ (1) | NZ202688A (el) |
| PT (1) | PT75925B (el) |
| ZA (1) | ZA828877B (el) |
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 EP EP82402172A patent/EP0082040B1/fr not_active Expired
- 1982-11-29 DE DE8282402172T patent/DE3268605D1/de not_active Expired
- 1982-11-29 AT AT82402172T patent/ATE17485T1/de active
- 1982-12-02 HU HU828374A patent/HU186180B/hu unknown
- 1982-12-02 CA CA000416847A patent/CA1196329A/en not_active Expired
- 1982-12-02 PT PT75925A patent/PT75925B/pt unknown
- 1982-12-02 NO NO824040A patent/NO824040L/no unknown
- 1982-12-02 GR GR69964A patent/GR77848B/el unknown
- 1982-12-02 IL IL67400A patent/IL67400A/xx unknown
- 1982-12-02 DK DK535082A patent/DK535082A/da not_active Application Discontinuation
- 1982-12-02 FI FI824155A patent/FI71321C/fi not_active IP Right Cessation
- 1982-12-02 ZA ZA828877A patent/ZA828877B/xx unknown
- 1982-12-02 NZ NZ202688A patent/NZ202688A/en unknown
- 1982-12-02 US US06/446,368 patent/US4503058A/en not_active Expired - Fee Related
- 1982-12-02 ES ES517874A patent/ES517874A0/es active Granted
- 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 |
|---|---|
| FR2517679A1 (fr) | 1983-06-10 |
| FI71321B (fi) | 1986-09-09 |
| AU553493B2 (en) | 1986-07-17 |
| EP0082040B1 (fr) | 1986-01-15 |
| NZ202688A (en) | 1985-01-31 |
| ES8401488A1 (es) | 1983-12-01 |
| PT75925B (fr) | 1985-12-20 |
| IL67400A0 (en) | 1983-05-15 |
| DE3268605D1 (en) | 1986-02-27 |
| PT75925A (fr) | 1983-01-01 |
| FI824155A0 (fi) | 1982-12-02 |
| IL67400A (en) | 1985-07-31 |
| JPS58109487A (ja) | 1983-06-29 |
| GR77848B (el) | 1984-09-25 |
| FI824155L (fi) | 1983-06-04 |
| AU9107682A (en) | 1983-06-09 |
| FI71321C (fi) | 1986-12-19 |
| CA1196329A (en) | 1985-11-05 |
| DK535082A (da) | 1983-06-04 |
| FR2517679B1 (el) | 1984-01-27 |
| HU186180B (en) | 1985-06-28 |
| ES517874A0 (es) | 1983-12-01 |
| ZA828877B (en) | 1983-09-28 |
| US4503058A (en) | 1985-03-05 |
| ATE17485T1 (de) | 1986-02-15 |
| EP0082040A1 (fr) | 1983-06-22 |
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