DE3143179A1 - Naphthyridinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Naphthyridinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE3143179A1 DE3143179A1 DE19813143179 DE3143179A DE3143179A1 DE 3143179 A1 DE3143179 A1 DE 3143179A1 DE 19813143179 DE19813143179 DE 19813143179 DE 3143179 A DE3143179 A DE 3143179A DE 3143179 A1 DE3143179 A1 DE 3143179A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- naphthyridine
- hydrogen atom
- pharmaceutically acceptable
- alkyl group
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 7
- 229940126601 medicinal product Drugs 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000005054 naphthyridines Chemical class 0.000 claims 4
- 150000005055 1,5-naphthyridines Chemical class 0.000 claims 1
- 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 1
- 238000005744 Teer Meer reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
- 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 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- -1 lithium aluminum hydride Chemical compound 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 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
- 244000025254 Cannabis sativa Species 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 231100000111 LD50 Toxicity 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
- 241000699666 Mus <mouse, genus> Species 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
- 238000004458 analytical method Methods 0.000 description 1
- 230000000496 anti-anoxic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 230000035565 breathing frequency Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 208000030499 combat disease Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000003455 parietal bone Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange 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
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 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
- 238000005303 weighing Methods 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 |
|---|---|
| DE3143179A1 true DE3143179A1 (de) | 1982-06-24 |
Family
ID=9248208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813143179 Withdrawn DE3143179A1 (de) | 1980-11-21 | 1981-10-30 | Naphthyridinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Country Status (22)
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 |
| US4997831A (en) * | 1988-09-01 | 1991-03-05 | Glaxo Group Limited | Lactam derivatives |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2716190A1 (de) * | 1976-04-13 | 1977-10-27 | Synthelabo | Naphtyridinderivate, ein verfahren zu ihrer herstellung und diese verbindungen als wirkstoffe enthaltende arzneimittel |
| DE2758405A1 (de) * | 1976-12-31 | 1978-07-13 | Logeais Labor Jacques | Arzneimittelzubereitung, enthaltend 1,2,3,3a,4,5-hexahydrocanthinderivate |
-
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 SE SE8106918A patent/SE8106918L/xx not_active Application Discontinuation
- 1981-11-20 NZ NZ199008A patent/NZ199008A/en unknown
- 1981-11-20 CH CH7460/81A patent/CH649549A5/fr not_active IP Right Cessation
- 1981-11-20 AT AT0501381A patent/AT379594B/de not_active IP Right Cessation
- 1981-11-20 AU AU77700/81A patent/AU546924B2/en not_active Ceased
- 1981-11-20 JP JP56187652A patent/JPS57116070A/ja active Pending
- 1981-11-20 ES ES507317A patent/ES507317A0/es active Granted
- 1981-11-20 GB GB8135005A patent/GB2087889B/en not_active Expired
- 1981-11-20 CA CA000390531A patent/CA1162544A/en not_active Expired
- 1981-11-20 ZA ZA818082A patent/ZA818082B/xx unknown
- 1981-11-20 IT IT25212/81A patent/IT1195292B/it active
- 1981-11-20 NO NO813945A patent/NO813945L/no unknown
- 1981-11-20 BE BE0/206615A patent/BE891204A/fr not_active IP Right Cessation
- 1981-11-20 IL IL64328A patent/IL64328A/xx unknown
- 1981-11-20 DK DK515681A patent/DK515681A/da not_active Application Discontinuation
- 1981-11-20 PT PT74019A patent/PT74019B/pt unknown
- 1981-11-20 IE IE2722/81A patent/IE52160B1/en unknown
- 1981-11-23 NL NL8105282A patent/NL8105282A/nl not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2716190A1 (de) * | 1976-04-13 | 1977-10-27 | Synthelabo | Naphtyridinderivate, ein verfahren zu ihrer herstellung und diese verbindungen als wirkstoffe enthaltende arzneimittel |
| DE2758405A1 (de) * | 1976-12-31 | 1978-07-13 | Logeais Labor Jacques | Arzneimittelzubereitung, enthaltend 1,2,3,3a,4,5-hexahydrocanthinderivate |
Also Published As
| Publication number | Publication date |
|---|---|
| NO813945L (no) | 1982-05-24 |
| ES8207176A1 (es) | 1982-09-01 |
| PT74019A (fr) | 1981-12-01 |
| IT8125212A0 (it) | 1981-11-20 |
| IL64328A0 (en) | 1982-02-28 |
| PT74019B (fr) | 1983-12-07 |
| FR2494693B1 (enrdf_load_stackoverflow) | 1983-03-04 |
| IE52160B1 (en) | 1987-07-22 |
| FR2494693A1 (fr) | 1982-05-28 |
| AU546924B2 (en) | 1985-09-26 |
| IT1195292B (it) | 1988-10-12 |
| AU7770081A (en) | 1982-05-27 |
| GB2087889B (en) | 1984-01-25 |
| ZA818082B (en) | 1982-10-27 |
| JPS57116070A (en) | 1982-07-19 |
| DK515681A (da) | 1982-05-22 |
| CA1162544A (en) | 1984-02-21 |
| GR78026B (enrdf_load_stackoverflow) | 1984-09-26 |
| BE891204A (fr) | 1982-05-21 |
| CH649549A5 (fr) | 1985-05-31 |
| SE8106918L (sv) | 1982-05-22 |
| LU83775A1 (fr) | 1983-09-01 |
| ES507317A0 (es) | 1982-09-01 |
| IL64328A (en) | 1985-02-28 |
| NL8105282A (nl) | 1982-06-16 |
| IE812722L (en) | 1982-05-21 |
| AT379594B (de) | 1986-01-27 |
| GB2087889A (en) | 1982-06-03 |
| NZ199008A (en) | 1984-07-31 |
| ATA501381A (de) | 1985-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8130 | Withdrawal |