FI63404C - Foerfarande foer framstaellning av antianoxiska 1,2,3,3a,4,5-hexahydro-6-oxo-6h-indolo(3,2,1-de) (1,5)naftyridiner - Google Patents
Foerfarande foer framstaellning av antianoxiska 1,2,3,3a,4,5-hexahydro-6-oxo-6h-indolo(3,2,1-de) (1,5)naftyridiner Download PDFInfo
- Publication number
- FI63404C FI63404C FI771159A FI771159A FI63404C FI 63404 C FI63404 C FI 63404C FI 771159 A FI771159 A FI 771159A FI 771159 A FI771159 A FI 771159A FI 63404 C FI63404 C FI 63404C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- hooc
- cooh
- indolo
- hexahydro
- Prior art date
Links
- JWKLUJICNLQLKG-UHFFFAOYSA-N sbb046058 Chemical compound C1=CC=C2C(CCN3)=C4C3CCC(=O)N4C2=C1 JWKLUJICNLQLKG-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical class C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000006114 decarboxylation reaction Methods 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical group C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 150000002310 glutaric acid derivatives Chemical class 0.000 claims 1
- -1 glutaryl Chemical class 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011541 reaction mixture Substances 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
- 241000700159 Rattus Species 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 230000004617 sleep duration Effects 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FVQKQPVVCKOWLM-UHFFFAOYSA-N 2-(5-chloro-1h-indol-3-yl)ethanamine Chemical compound C1=C(Cl)C=C2C(CCN)=CNC2=C1 FVQKQPVVCKOWLM-UHFFFAOYSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 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
- 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
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000141 anti-hypoxic effect Effects 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 230000002308 calcification Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 210000000103 occipital bone Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 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
- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7610773 | 1976-04-13 | ||
| FR7610773A FR2358146A1 (fr) | 1976-04-13 | 1976-04-13 | Derives de la tetrahydro-1,2,3,3a indolo(3,2,1-de) (1,5)naphtyridine |
| FR7616445A FR2353550A2 (fr) | 1976-06-01 | 1976-06-01 | Procede de preparation de derives de naphtyridine |
| FR7616445 | 1976-06-01 | ||
| FR7632319 | 1976-10-27 | ||
| FR7632319A FR2368955A2 (fr) | 1976-10-27 | 1976-10-27 | Derives de la tetrahydro-1,2,3,3a indolo (3,2,1-de) (1,5) naphtyridine |
| FR7639035 | 1976-12-24 | ||
| FR7639035A FR2374905A2 (fr) | 1976-12-24 | 1976-12-24 | Derives de naphtyridine |
| FR7707249 | 1977-03-11 | ||
| FR7707249A FR2383182A2 (fr) | 1977-03-11 | 1977-03-11 | Nouveaux derives de naphtyridine |
| FR7707248A FR2383181A2 (fr) | 1977-03-11 | 1977-03-11 | Derives de naphtyridine |
| FR7707248 | 1977-03-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771159A7 FI771159A7 (en:Method) | 1977-10-14 |
| FI63404B FI63404B (fi) | 1983-02-28 |
| FI63404C true FI63404C (fi) | 1983-06-10 |
Family
ID=27546337
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771159A FI63404C (fi) | 1976-04-13 | 1977-04-13 | Foerfarande foer framstaellning av antianoxiska 1,2,3,3a,4,5-hexahydro-6-oxo-6h-indolo(3,2,1-de) (1,5)naftyridiner |
| FI803790A FI803790A7 (fi) | 1976-04-13 | 1977-04-13 | Menetelmä anoksemian vastaisten 1,2,3,3a,4,5-heksahydro-6-okso-6H-indolo/3,2,1-de/ /1,5/naftyridiinien valmistavalmistamiseksi. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI803790A FI803790A7 (fi) | 1976-04-13 | 1977-04-13 | Menetelmä anoksemian vastaisten 1,2,3,3a,4,5-heksahydro-6-okso-6H-indolo/3,2,1-de/ /1,5/naftyridiinien valmistavalmistamiseksi. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4190657A (en:Method) |
| JP (1) | JPS5823877B2 (en:Method) |
| AR (1) | AR214519A1 (en:Method) |
| AU (1) | AU506031B2 (en:Method) |
| CA (1) | CA1072960A (en:Method) |
| CH (1) | CH622795A5 (en:Method) |
| DD (1) | DD129791A5 (en:Method) |
| DE (1) | DE2716190A1 (en:Method) |
| DK (1) | DK143703C (en:Method) |
| FI (2) | FI63404C (en:Method) |
| GB (1) | GB1543283A (en:Method) |
| GR (1) | GR63658B (en:Method) |
| IE (1) | IE44989B1 (en:Method) |
| IL (1) | IL51853A (en:Method) |
| LU (1) | LU77100A1 (en:Method) |
| MT (1) | MTP811B (en:Method) |
| MX (1) | MX5340E (en:Method) |
| NO (1) | NO146777C (en:Method) |
| NZ (1) | NZ183846A (en:Method) |
| PL (1) | PL197373A1 (en:Method) |
| PT (1) | PT66428B (en:Method) |
| SE (2) | SE432932B (en:Method) |
| SU (1) | SU655314A3 (en:Method) |
| YU (1) | YU94877A (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5337696A (en) * | 1976-08-26 | 1978-04-06 | Omnium Chimique Sa | Hexahydrocantinonee6 derivative |
| US4228168A (en) * | 1978-11-22 | 1980-10-14 | Tanabe Seiyaku Co., Ltd. | Azepino [1,2,3-lm]-β-carboline compounds and pharmaceutical composition thereof |
| US4367230A (en) * | 1980-01-04 | 1983-01-04 | Tanabe Seiyaku Co., Ltd. | Novel triazafluoranthene compound and processes for preparing the same |
| FR2494693A1 (fr) * | 1980-11-21 | 1982-05-28 | Synthelabo | 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 |
| FR2517679A1 (fr) * | 1981-12-03 | 1983-06-10 | Synthelabo | Derives de diaza-3,7a cyclohepta (j,k) fluorenes, leur preparation et leur application en therapeutique |
| LU84664A1 (fr) * | 1983-02-25 | 1984-11-08 | Onmichem S A | Alkyl-4-indolonaphtyridines et leur application therapeutique |
| EP0347980A1 (en) * | 1988-06-20 | 1989-12-27 | Duphar International Research B.V | 8,9-Annelated beta-carbolines and 8,9-anelated-3,4-dihydro-beta-carbolines |
| CN103193776A (zh) * | 2013-04-16 | 2013-07-10 | 苏州维泰生物技术有限公司 | 一种具有抗肿瘤疗效的新型萘啶衍生物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299078A (en) * | 1962-10-01 | 1967-01-17 | Smith Kline French Lab | Pyrido [3', 4': 4, 5] pyrrolo [3, 2, 1-hi] indoles and-[3, 2, 1-ij] quinolines |
| US3555018A (en) * | 1968-12-03 | 1971-01-12 | Ayerst Mckenna & Harrison | Thiazinopyridoindolone derivatives |
-
1977
- 1977-04-07 DD DD7700198314A patent/DD129791A5/xx unknown
- 1977-04-11 MT MT811A patent/MTP811B/xx unknown
- 1977-04-11 YU YU00948/77A patent/YU94877A/xx unknown
- 1977-04-11 US US05/786,557 patent/US4190657A/en not_active Expired - Lifetime
- 1977-04-11 JP JP52041904A patent/JPS5823877B2/ja not_active Expired
- 1977-04-11 IL IL51853A patent/IL51853A/xx unknown
- 1977-04-12 NO NO77771263A patent/NO146777C/no unknown
- 1977-04-12 PT PT66428A patent/PT66428B/pt unknown
- 1977-04-12 AU AU24189/77A patent/AU506031B2/en not_active Expired
- 1977-04-12 GB GB15165/77A patent/GB1543283A/en not_active Expired
- 1977-04-12 CA CA275,948A patent/CA1072960A/en not_active Expired
- 1977-04-12 LU LU77100A patent/LU77100A1/xx unknown
- 1977-04-12 MX MX775626U patent/MX5340E/es unknown
- 1977-04-12 CH CH450777A patent/CH622795A5/fr not_active IP Right Cessation
- 1977-04-12 DE DE19772716190 patent/DE2716190A1/de not_active Withdrawn
- 1977-04-12 SE SE7704172A patent/SE432932B/xx unknown
- 1977-04-12 AR AR267179A patent/AR214519A1/es active
- 1977-04-12 DK DK161377A patent/DK143703C/da not_active IP Right Cessation
- 1977-04-13 SU SU772470258A patent/SU655314A3/ru active
- 1977-04-13 NZ NZ183846A patent/NZ183846A/xx unknown
- 1977-04-13 GR GR53198A patent/GR63658B/el unknown
- 1977-04-13 FI FI771159A patent/FI63404C/fi not_active IP Right Cessation
- 1977-04-13 PL PL19737377A patent/PL197373A1/xx unknown
- 1977-04-13 FI FI803790A patent/FI803790A7/fi not_active Application Discontinuation
- 1977-04-13 IE IE758/77A patent/IE44989B1/en unknown
-
1982
- 1982-02-25 SE SE8201181A patent/SE8201181L/sv not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SYNTHELABO |