JPS5948482A - ナフチリジン化合物 - Google Patents
ナフチリジン化合物Info
- Publication number
- JPS5948482A JPS5948482A JP57159358A JP15935882A JPS5948482A JP S5948482 A JPS5948482 A JP S5948482A JP 57159358 A JP57159358 A JP 57159358A JP 15935882 A JP15935882 A JP 15935882A JP S5948482 A JPS5948482 A JP S5948482A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- naphthyridine
- derivative
- novel
- 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.)
- Granted
Links
- 150000005054 naphthyridines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- -1 naphthyridine compound Chemical class 0.000 claims description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 abstract description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
- 241000243142 Porifera Species 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 229910052697 platinum Inorganic materials 0.000 abstract description 2
- 241001349860 Aaptos aaptos Species 0.000 abstract 1
- UERYGOYPBXIFQV-UHFFFAOYSA-N aaptamine Chemical compound C1=NC2=C(OC)C(OC)=CC(C=CN3)=C2C3=C1 UERYGOYPBXIFQV-UHFFFAOYSA-N 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000000948 sympatholitic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 17
- IVXSXOFPZFVZTM-UHFFFAOYSA-N chembl234658 Chemical compound C1=CNC2=C(OC)C(OC)=CC3=CC=NC1=C32 IVXSXOFPZFVZTM-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- DLRZUOXGCSITOV-KOLCDFICSA-N aaptamine Natural products COC1=CC2=CC=N[C@@H]3C=CNC(=C1OC)[C@@H]23 DLRZUOXGCSITOV-KOLCDFICSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229960002748 norepinephrine Drugs 0.000 description 6
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- ZLLLBEQWLHKRLA-UHFFFAOYSA-N chembl491094 Chemical compound C1=CNC2=C(O)C(O)=CC3=CC=NC1=C32 ZLLLBEQWLHKRLA-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- XUBVCJMVRGITPS-UHFFFAOYSA-N demethylaaptamine hydrochloride Natural products COc1cc2ccnc3C=CNc(c1O)c23 XUBVCJMVRGITPS-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 230000002889 sympathetic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 210000000078 claw Anatomy 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 241000676807 Aaptos Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 101150025446 Atn1 gene Proteins 0.000 description 1
- 102100034744 Cell division cycle 7-related protein kinase Human genes 0.000 description 1
- 206010015719 Exsanguination Diseases 0.000 description 1
- 101000945740 Homo sapiens Cell division cycle 7-related protein kinase Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001441724 Tetraodontidae Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 210000002376 aorta thoracic Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57159358A JPS5948482A (ja) | 1982-09-13 | 1982-09-13 | ナフチリジン化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57159358A JPS5948482A (ja) | 1982-09-13 | 1982-09-13 | ナフチリジン化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5948482A true JPS5948482A (ja) | 1984-03-19 |
| JPH046714B2 JPH046714B2 (enrdf_load_stackoverflow) | 1992-02-06 |
Family
ID=15692094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57159358A Granted JPS5948482A (ja) | 1982-09-13 | 1982-09-13 | ナフチリジン化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5948482A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61253709A (ja) * | 1985-04-30 | 1986-11-11 | 太陽誘電株式会社 | 誘電体磁器組成物 |
-
1982
- 1982-09-13 JP JP57159358A patent/JPS5948482A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61253709A (ja) * | 1985-04-30 | 1986-11-11 | 太陽誘電株式会社 | 誘電体磁器組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH046714B2 (enrdf_load_stackoverflow) | 1992-02-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR920006365A (ko) | 신규의 프레그나-1,4-디엔 -3,20-디온-16,17-아세탈-21-에스테르류, 이것의 제조방법, 이것을 함유한 조성물 및 염증질환의 치료방법 | |
| TW200410941A (en) | Naphthol, quinoline and isoquinoline-derived urea modulators of vanilloid VR1 receptor | |
| Stempel et al. | Quinazolines and 1, 4-Benzodiazepines. IX. 2-Carbobenzoxyglycylamidobenzophenones and Their Conversion to 1, 4-Benzodiazepinones | |
| Schaffer et al. | Structure of 5-Aldo-1, 2-O-isopropylidene-D-xylo-pentofuranose1 | |
| JPS5948482A (ja) | ナフチリジン化合物 | |
| FR2510583A1 (fr) | Derives nouveaux d'acide ursodesoxycholique, leur procede de preparation et leur application en therapeutique | |
| WO2010109687A1 (ja) | サンゴ由来の炎症、アレルギー性疾患治療薬 | |
| US3113970A (en) | Process for preparing benzophenone compounds | |
| DE2427207A1 (de) | Verfahren zur herstellung von kondensierten pyrrolmercapto-verbindungen | |
| CH637650A5 (fr) | Procede de preparation d'un acide chromone carboxylique. | |
| JPH04368359A (ja) | カプサイシン誘導体又はその酸エステルを有効成分とする鎮痛剤、血管拡張剤 | |
| US4520029A (en) | Farnesene derivatives, mucosal stabilizing compositions and method of manufacturing the same | |
| US3904599A (en) | Cardenolide-3-(2'-desoxy-glycosides)+0 and process for their manufacture | |
| Weizmann et al. | β, β-Diarylacrylic Acids. III. Esters with Diethylaminoethanol as Anesthetics | |
| US2352012A (en) | Sulphanilamide addition compound | |
| JPS5920298A (ja) | 新規トリテルペン配糖体 | |
| DE69705238T2 (de) | Derivate der asiatica-saeure mit einem modifizierten a-ring | |
| FR2503150A1 (fr) | Mercaptoacyl-carnitines, procede pour leur preparation et leurs utilisations therapeutiques dans le traitement des intoxications et des brulures et en tant qu'agents mucolytiques | |
| JPS63227582A (ja) | 新規２−（２，３−ジヒドロ−２−オキソ−３−ベンゾフラニル）酢酸誘導体その製造法およびそれを含有する薬学的組成物 | |
| JPH0358953A (ja) | （ｓ）―５―ヒドロキシデカン酸およびそれを有効成分とする医薬組成物 | |
| US4011212A (en) | 22-cyano-24-norcholanes | |
| US3944541A (en) | 22-Cyano-24-norcholanes | |
| US3478068A (en) | 4alpha,10alpha;2beta,1' - bicyclo - 5beta - methyl - 19 - nor-steroids and their preparation | |
| US3793316A (en) | 5-nitrofuryl derivatives | |
| AT253142B (de) | Verfahren zur Herstellung von neuen schwefelhaltigen Androstanderivaten |