NO813945L - Fremgangsmaate for fremstilling av naftyridinderivater - Google Patents
Fremgangsmaate for fremstilling av naftyridinderivaterInfo
- Publication number
- NO813945L NO813945L NO813945A NO813945A NO813945L NO 813945 L NO813945 L NO 813945L NO 813945 A NO813945 A NO 813945A NO 813945 A NO813945 A NO 813945A NO 813945 L NO813945 L NO 813945L
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- preparation
- naftyridine
- derivatives
- procedure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 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
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- 231100000111 LD50 Toxicity 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 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
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 206010002660 Anoxia Diseases 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 208000026680 Metabolic Brain disease Diseases 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- CPYGBGOXCJJJGC-GKLGUMFISA-L alcuronium chloride Chemical compound [Cl-].[Cl-].C/1([C@@H]23)=C\N([C@H]4\5)C6=CC=CC=C6[C@]4(CC[N@@+]4(CC=C)C\C6=C\CO)[C@@H]4C[C@@H]6C/5=C/N3C3=CC=CC=C3[C@@]22CC[N@@+]3(CC=C)C/C(=C/CO)[C@@H]\1C[C@H]32 CPYGBGOXCJJJGC-GKLGUMFISA-L 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000006931 brain damage Effects 0.000 description 1
- 231100000874 brain damage Toxicity 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229940072358 xylocaine Drugs 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- X-Ray Techniques (AREA)
- Carbon And Carbon Compounds (AREA)
- Secondary Cells (AREA)
- Electrolytic Production Of Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8024717A FR2494693A1 (fr) | 1980-11-21 | 1980-11-21 | Derives de l'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2,1-de)(naphtyridine-1,5), leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO813945L true NO813945L (no) | 1982-05-24 |
Family
ID=9248208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO813945A NO813945L (no) | 1980-11-21 | 1981-11-20 | Fremgangsmaate for fremstilling av naftyridinderivater |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS57116070A (sv) |
| AT (1) | AT379594B (sv) |
| AU (1) | AU546924B2 (sv) |
| BE (1) | BE891204A (sv) |
| CA (1) | CA1162544A (sv) |
| CH (1) | CH649549A5 (sv) |
| DE (1) | DE3143179A1 (sv) |
| DK (1) | DK515681A (sv) |
| ES (1) | ES507317A0 (sv) |
| FR (1) | FR2494693A1 (sv) |
| GB (1) | GB2087889B (sv) |
| GR (1) | GR78026B (sv) |
| IE (1) | IE52160B1 (sv) |
| IL (1) | IL64328A (sv) |
| IT (1) | IT1195292B (sv) |
| LU (1) | LU83775A1 (sv) |
| NL (1) | NL8105282A (sv) |
| NO (1) | NO813945L (sv) |
| NZ (1) | NZ199008A (sv) |
| PT (1) | PT74019B (sv) |
| SE (1) | SE8106918L (sv) |
| ZA (1) | ZA818082B (sv) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2527210A1 (fr) * | 1982-05-18 | 1983-11-25 | Synthelabo | Enantiomeres d'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2,1-de) (naphtyridine-1,5), leur procede de separation et leur application en therapeutique |
| JPH02180885A (ja) * | 1988-09-01 | 1990-07-13 | Glaxo Group Ltd | ラクタム誘導体 |
| CN113214250B (zh) * | 2021-04-28 | 2022-06-14 | 华南理工大学 | 一种稠合六氢-1,6-萘啶类化合物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD129791A5 (de) * | 1976-04-13 | 1978-02-08 | Synthelabo | Verfahren zur herstellung von naphtyridinderivaten |
| GB1550496A (en) * | 1976-12-31 | 1979-08-15 | Logeais Labor Jacques | 1,2,3,3a4,5-hexahydro-canthine derivatives a process for their preparation and their therapeutic applications |
-
1980
- 1980-11-21 FR FR8024717A patent/FR2494693A1/fr active Granted
-
1981
- 1981-10-30 DE DE19813143179 patent/DE3143179A1/de not_active Withdrawn
- 1981-11-17 GR GR66585A patent/GR78026B/el unknown
- 1981-11-19 LU LU83775A patent/LU83775A1/fr unknown
- 1981-11-20 NZ NZ199008A patent/NZ199008A/en unknown
- 1981-11-20 ZA ZA818082A patent/ZA818082B/xx unknown
- 1981-11-20 JP JP56187652A patent/JPS57116070A/ja active Pending
- 1981-11-20 IL IL64328A patent/IL64328A/xx unknown
- 1981-11-20 IT IT25212/81A patent/IT1195292B/it active
- 1981-11-20 IE IE2722/81A patent/IE52160B1/en unknown
- 1981-11-20 AU AU77700/81A patent/AU546924B2/en not_active Ceased
- 1981-11-20 CH CH7460/81A patent/CH649549A5/fr not_active IP Right Cessation
- 1981-11-20 CA CA000390531A patent/CA1162544A/en not_active Expired
- 1981-11-20 DK DK515681A patent/DK515681A/da not_active Application Discontinuation
- 1981-11-20 PT PT74019A patent/PT74019B/pt unknown
- 1981-11-20 BE BE0/206615A patent/BE891204A/fr not_active IP Right Cessation
- 1981-11-20 NO NO813945A patent/NO813945L/no unknown
- 1981-11-20 SE SE8106918A patent/SE8106918L/sv not_active Application Discontinuation
- 1981-11-20 AT AT0501381A patent/AT379594B/de not_active IP Right Cessation
- 1981-11-20 GB GB8135005A patent/GB2087889B/en not_active Expired
- 1981-11-20 ES ES507317A patent/ES507317A0/es active Granted
- 1981-11-23 NL NL8105282A patent/NL8105282A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2494693A1 (fr) | 1982-05-28 |
| NZ199008A (en) | 1984-07-31 |
| IL64328A0 (en) | 1982-02-28 |
| IT8125212A0 (it) | 1981-11-20 |
| BE891204A (fr) | 1982-05-21 |
| PT74019A (fr) | 1981-12-01 |
| JPS57116070A (en) | 1982-07-19 |
| DK515681A (da) | 1982-05-22 |
| CA1162544A (en) | 1984-02-21 |
| AT379594B (de) | 1986-01-27 |
| IE52160B1 (en) | 1987-07-22 |
| GB2087889A (en) | 1982-06-03 |
| ES8207176A1 (es) | 1982-09-01 |
| IE812722L (en) | 1982-05-21 |
| FR2494693B1 (sv) | 1983-03-04 |
| NL8105282A (nl) | 1982-06-16 |
| AU7770081A (en) | 1982-05-27 |
| GR78026B (sv) | 1984-09-26 |
| ZA818082B (en) | 1982-10-27 |
| DE3143179A1 (de) | 1982-06-24 |
| IL64328A (en) | 1985-02-28 |
| LU83775A1 (fr) | 1983-09-01 |
| ATA501381A (de) | 1985-06-15 |
| GB2087889B (en) | 1984-01-25 |
| CH649549A5 (fr) | 1985-05-31 |
| AU546924B2 (en) | 1985-09-26 |
| SE8106918L (sv) | 1982-05-22 |
| PT74019B (fr) | 1983-12-07 |
| IT1195292B (it) | 1988-10-12 |
| ES507317A0 (es) | 1982-09-01 |
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