SE445347B - 8-metoxi-3-fenyl-5-metylpropargylaminometyl-1,2-bensopyron med antikonvulsiv aktivitet, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande nemnda forening - Google Patents
8-metoxi-3-fenyl-5-metylpropargylaminometyl-1,2-bensopyron med antikonvulsiv aktivitet, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande nemnda foreningInfo
- Publication number
- SE445347B SE445347B SE7902004A SE7902004A SE445347B SE 445347 B SE445347 B SE 445347B SE 7902004 A SE7902004 A SE 7902004A SE 7902004 A SE7902004 A SE 7902004A SE 445347 B SE445347 B SE 445347B
- Authority
- SE
- Sweden
- Prior art keywords
- benzopyrone
- phenyl
- compound
- pharmaceutical compositions
- methyl
- Prior art date
Links
- 229960000956 coumarin Drugs 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 239000000126 substance Substances 0.000 title description 3
- 230000002082 anti-convulsion Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 5
- DAOPKAGAUIPYPR-UHFFFAOYSA-N 8-methoxy-5-[[methyl(prop-2-ynyl)amino]methyl]-3-phenylchromen-2-one Chemical compound O=C1OC=2C(OC)=CC=C(CN(C)CC#C)C=2C=C1C1=CC=CC=C1 DAOPKAGAUIPYPR-UHFFFAOYSA-N 0.000 claims description 3
- HQFYIDOMCULPIW-UHFFFAOYSA-N n-methylprop-2-yn-1-amine Chemical compound CNCC#C HQFYIDOMCULPIW-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000002920 convulsive effect Effects 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000007265 chloromethylation reaction Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000037396 body weight Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 238000009227 behaviour therapy Methods 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10421/78A GB1555852A (en) | 1978-03-16 | 1978-03-16 | Hetercyclic propargylaminomethyl dervatives as a medicamend method for its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7902004L SE7902004L (sv) | 1979-09-17 |
| SE445347B true SE445347B (sv) | 1986-06-16 |
Family
ID=9967511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7902004A SE445347B (sv) | 1978-03-16 | 1979-03-06 | 8-metoxi-3-fenyl-5-metylpropargylaminometyl-1,2-bensopyron med antikonvulsiv aktivitet, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande nemnda forening |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4218467A (ja) |
| JP (1) | JPS607992B2 (ja) |
| AU (1) | AU520261B2 (ja) |
| BE (1) | BE874777A (ja) |
| CA (1) | CA1103686A (ja) |
| CH (1) | CH638197A5 (ja) |
| DE (1) | DE2909038C2 (ja) |
| ES (1) | ES478732A1 (ja) |
| FR (1) | FR2419941B1 (ja) |
| GB (1) | GB1555852A (ja) |
| IL (1) | IL56773A (ja) |
| IT (1) | IT1193470B (ja) |
| NL (1) | NL181805C (ja) |
| SE (1) | SE445347B (ja) |
| ZA (1) | ZA79977B (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7092974B2 (ja) | 2018-03-26 | 2022-06-29 | 株式会社リコー | 樹脂微粒子の製造方法、及び樹脂微粒子の製造装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1426064A (fr) * | 1962-04-03 | 1966-01-28 | Dausse Lab | Dérivés du méthyl-4-aesculétol et leur préparation |
-
1978
- 1978-03-16 GB GB10421/78A patent/GB1555852A/en not_active Expired
-
1979
- 1979-02-28 IT IT20642/79A patent/IT1193470B/it active
- 1979-02-28 NL NLAANVRAGE7901592,A patent/NL181805C/xx not_active IP Right Cessation
- 1979-03-01 ZA ZA79977A patent/ZA79977B/xx unknown
- 1979-03-01 IL IL56773A patent/IL56773A/xx unknown
- 1979-03-02 US US06/016,908 patent/US4218467A/en not_active Expired - Lifetime
- 1979-03-05 CA CA322,722A patent/CA1103686A/en not_active Expired
- 1979-03-06 SE SE7902004A patent/SE445347B/sv not_active IP Right Cessation
- 1979-03-08 DE DE2909038A patent/DE2909038C2/de not_active Expired
- 1979-03-08 JP JP54027234A patent/JPS607992B2/ja not_active Expired
- 1979-03-09 CH CH226679A patent/CH638197A5/it not_active IP Right Cessation
- 1979-03-12 BE BE0/193974A patent/BE874777A/xx not_active IP Right Cessation
- 1979-03-14 FR FR7906484A patent/FR2419941B1/fr not_active Expired
- 1979-03-15 AU AU45144/79A patent/AU520261B2/en not_active Ceased
- 1979-03-16 ES ES478732A patent/ES478732A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7901592A (nl) | 1979-09-18 |
| DE2909038C2 (de) | 1983-11-24 |
| GB1555852A (en) | 1979-11-14 |
| IT1193470B (it) | 1988-07-08 |
| NL181805C (nl) | 1987-11-02 |
| ZA79977B (en) | 1980-03-26 |
| IL56773A (en) | 1982-08-31 |
| ES478732A1 (es) | 1979-11-01 |
| JPS54141775A (en) | 1979-11-05 |
| FR2419941B1 (fr) | 1981-10-09 |
| CH638197A5 (it) | 1983-09-15 |
| IL56773A0 (en) | 1979-05-31 |
| DE2909038A1 (de) | 1979-09-20 |
| CA1103686A (en) | 1981-06-23 |
| BE874777A (fr) | 1979-07-02 |
| US4218467A (en) | 1980-08-19 |
| AU520261B2 (en) | 1982-01-21 |
| IT7920642A0 (it) | 1979-02-28 |
| SE7902004L (sv) | 1979-09-17 |
| FR2419941A1 (fr) | 1979-10-12 |
| JPS607992B2 (ja) | 1985-02-28 |
| AU4514479A (en) | 1979-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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