CA1128519A - Derives de 6-methoxy-2-acetylnaphtalene oxime, leur preparation et leur application en tant que medicaments - Google Patents
Derives de 6-methoxy-2-acetylnaphtalene oxime, leur preparation et leur application en tant que medicamentsInfo
- Publication number
- CA1128519A CA1128519A CA333,015A CA333015A CA1128519A CA 1128519 A CA1128519 A CA 1128519A CA 333015 A CA333015 A CA 333015A CA 1128519 A CA1128519 A CA 1128519A
- Authority
- CA
- Canada
- Prior art keywords
- oxime
- methoxy
- prepared
- acetylnaphthalene
- derivatives
- 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.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 230000000144 pharmacologic effect Effects 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- FKUMAWUBPURONA-UHFFFAOYSA-N n-[1-(6-methoxynaphthalen-2-yl)ethylidene]hydroxylamine Chemical class C1=C(C(C)=NO)C=CC2=CC(OC)=CC=C21 FKUMAWUBPURONA-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 150000002923 oximes Chemical class 0.000 claims description 10
- -1 alkyl radical Chemical class 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- 238000001311 chemical methods and process Methods 0.000 claims 7
- 229960004756 ethanol Drugs 0.000 claims 3
- 235000019441 ethanol Nutrition 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- YELYFTPUYXSWRH-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)-n-(2-pyrrolidin-1-ylethoxy)ethanimine Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C)=NOCCN1CCCC1 YELYFTPUYXSWRH-UHFFFAOYSA-N 0.000 claims 1
- GGWCZBGAIGGTDA-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)ethanone Chemical compound C1=C(C(C)=O)C=CC2=CC(OC)=CC=C21 GGWCZBGAIGGTDA-UHFFFAOYSA-N 0.000 claims 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical class NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims 1
- SAJXURINXUVSAT-UHFFFAOYSA-N n,n-diethyl-2-[1-(6-methoxynaphthalen-2-yl)ethylideneamino]oxyethanamine Chemical compound C1=C(OC)C=CC2=CC(C(C)=NOCCN(CC)CC)=CC=C21 SAJXURINXUVSAT-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 230000000202 analgesic effect Effects 0.000 description 5
- 208000002193 Pain Diseases 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 101100421144 Danio rerio selenoo1 gene Proteins 0.000 description 2
- 206010019233 Headaches Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 101100202896 Mus musculus Selenoo gene Proteins 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 231100000869 headache Toxicity 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229940124641 pain reliever Drugs 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- 241000219498 Alnus glutinosa Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241001539019 Monolene Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000000307 algesic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7822836A FR2432506A1 (fr) | 1978-08-02 | 1978-08-02 | Nouveaux derives de 6-methoxy-2-acetylnaphtalene oxime, leur preparation et leur application en tant que medicaments |
| FR7822836 | 1978-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128519A true CA1128519A (fr) | 1982-07-27 |
Family
ID=9211492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA333,015A Expired CA1128519A (fr) | 1978-08-02 | 1979-08-01 | Derives de 6-methoxy-2-acetylnaphtalene oxime, leur preparation et leur application en tant que medicaments |
Country Status (25)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58156006U (ja) * | 1982-04-13 | 1983-10-18 | 日本電気ホームエレクトロニクス株式会社 | 車輌室内換気装置 |
| JPS61192912U (US06582424-20030624-M00016.png) * | 1985-05-25 | 1986-12-01 | ||
| JPH0525285Y2 (US06582424-20030624-M00016.png) * | 1987-01-12 | 1993-06-25 | ||
| JPS63173814U (US06582424-20030624-M00016.png) * | 1987-05-02 | 1988-11-11 | ||
| WO2006047703A2 (en) * | 2004-10-26 | 2006-05-04 | Sigma-Aldrich Co. | Synthesis of amino acid, n-carboxyanhydrides |
| GB2435830A (en) * | 2006-03-09 | 2007-09-12 | Del Dr Esteve S A Spain Lab | Oxime ether compounds for the treatment of conditions associated with food uptake |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963778A (en) * | 1965-11-10 | 1976-06-15 | Bayer Aktiengesellschaft | Basic oximes and their preparation |
| US3937841A (en) * | 1967-04-05 | 1976-02-10 | U.S. Philips Corporation | Treatment of depression |
-
1978
- 1978-08-02 FR FR7822836A patent/FR2432506A1/fr active Granted
-
1979
- 1979-06-06 ES ES481855A patent/ES481855A1/es not_active Expired
- 1979-07-20 US US06/059,249 patent/US4267334A/en not_active Expired - Lifetime
- 1979-07-26 YU YU1821/79A patent/YU41874B/xx unknown
- 1979-07-30 DD DD79214687A patent/DD145266A5/de not_active IP Right Cessation
- 1979-07-31 IL IL57931A patent/IL57931A/xx not_active IP Right Cessation
- 1979-07-31 PT PT70005A patent/PT70005A/pt unknown
- 1979-07-31 CH CH705179A patent/CH641773A5/fr not_active IP Right Cessation
- 1979-07-31 GR GR59743A patent/GR69826B/el unknown
- 1979-08-01 JP JP9860079A patent/JPS5555155A/ja active Granted
- 1979-08-01 CA CA333,015A patent/CA1128519A/fr not_active Expired
- 1979-08-01 EG EG466/79A patent/EG14368A/xx active
- 1979-08-01 RO RO7998336A patent/RO77339A/ro unknown
- 1979-08-01 NL NL7905939A patent/NL7905939A/nl not_active Application Discontinuation
- 1979-08-01 CS CS795313A patent/CS215016B2/cs unknown
- 1979-08-01 DE DE19792931319 patent/DE2931319A1/de not_active Ceased
- 1979-08-01 PL PL1979217508A patent/PL116462B1/pl unknown
- 1979-08-01 SE SE7906509A patent/SE446530B/sv not_active IP Right Cessation
- 1979-08-01 BG BG7944522A patent/BG36198A3/xx not_active Expired
- 1979-08-01 BE BE0/196559A patent/BE878019A/fr not_active IP Right Cessation
- 1979-08-01 AT AT0528779A patent/AT367744B/de not_active IP Right Cessation
- 1979-08-02 FI FI792414A patent/FI70012C/fi not_active IP Right Cessation
- 1979-08-02 SU SU792792753A patent/SU784763A3/ru active
- 1979-08-02 GB GB7926940A patent/GB2045743B/en not_active Expired
- 1979-08-02 AR AR277580A patent/AR221502A1/es active
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |