CA1037960A - Amidoxime derivatives and process for preparing the same - Google Patents
Amidoxime derivatives and process for preparing the sameInfo
- Publication number
- CA1037960A CA1037960A CA217,910A CA217910A CA1037960A CA 1037960 A CA1037960 A CA 1037960A CA 217910 A CA217910 A CA 217910A CA 1037960 A CA1037960 A CA 1037960A
- Authority
- CA
- Canada
- Prior art keywords
- benzofuryloxy
- propionamidoxime
- process according
- acceptable acid
- pharmaceutically acceptable
- 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
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical class C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 239000002253 acid Substances 0.000 claims abstract description 35
- 235000013350 formula milk Nutrition 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000002825 nitriles Chemical class 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012458 free base Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 3
- 150000007522 mineralic acids Chemical class 0.000 claims abstract 10
- 150000007524 organic acids Chemical class 0.000 claims abstract 10
- 238000000034 method Methods 0.000 claims description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 49
- 230000008569 process Effects 0.000 claims description 26
- 238000007792 addition Methods 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- KLWGWDOTUDKLKT-UHFFFAOYSA-N n'-hydroxy-2-naphthalen-1-yloxypropanimidamide Chemical compound C1=CC=C2C(OC(C)C(\N)=N/O)=CC=CC2=C1 KLWGWDOTUDKLKT-UHFFFAOYSA-N 0.000 claims description 4
- XAWUWHZQOIIIOU-UHFFFAOYSA-N 2-(1-benzofuran-7-yloxy)-n'-hydroxypropanimidamide Chemical compound ON=C(N)C(C)OC1=CC=CC2=C1OC=C2 XAWUWHZQOIIIOU-UHFFFAOYSA-N 0.000 claims description 3
- FGQFIYOQUKDTRI-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-7-yloxy)-n'-hydroxypropanimidamide Chemical compound ON=C(N)C(C)OC1=CC=CC2=C1OCC2 FGQFIYOQUKDTRI-UHFFFAOYSA-N 0.000 claims description 3
- JJIFJZGPCLFPNF-UHFFFAOYSA-N 3-(1-benzofuran-7-yloxy)-n'-hydroxypropanimidamide Chemical compound ON=C(N)CCOC1=CC=CC2=C1OC=C2 JJIFJZGPCLFPNF-UHFFFAOYSA-N 0.000 claims description 3
- HCDINVCUTOTTTA-UHFFFAOYSA-N n'-hydroxy-2-naphthalen-1-yloxybutanimidamide Chemical compound C1=CC=C2C(OC(CC)C(N)=NO)=CC=CC2=C1 HCDINVCUTOTTTA-UHFFFAOYSA-N 0.000 claims description 3
- RLZPCFQNZGINRP-UHFFFAOYSA-N n'-hydroxypropanimidamide Chemical compound CCC(N)=NO RLZPCFQNZGINRP-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
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- CNXMATRFSBXNSZ-UHFFFAOYSA-N n'-hydroxy-3-naphthalen-2-yloxypropanimidamide Chemical compound C1=CC=CC2=CC(OCCC(N)=NO)=CC=C21 CNXMATRFSBXNSZ-UHFFFAOYSA-N 0.000 claims 2
- SXBXFGJLNKWUAZ-UHFFFAOYSA-N 2-(1-benzofuran-4-yloxy)-n'-hydroxypropanimidamide Chemical compound ON=C(N)C(C)OC1=CC=CC2=C1C=CO2 SXBXFGJLNKWUAZ-UHFFFAOYSA-N 0.000 claims 1
- ZBNBADRUYYIOOU-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-7-yloxy)propanenitrile Chemical compound N#CC(C)OC1=CC=CC2=C1OCC2 ZBNBADRUYYIOOU-UHFFFAOYSA-N 0.000 claims 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
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- 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
- A61P25/24—Antidepressants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7401286A FR2257273B1 (en, 2012) | 1974-01-15 | 1974-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1037960A true CA1037960A (en) | 1978-09-05 |
Family
ID=9133487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA217,910A Expired CA1037960A (en) | 1974-01-15 | 1975-01-14 | Amidoxime derivatives and process for preparing the same |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3931240A (en, 2012) |
| JP (1) | JPS541301B2 (en, 2012) |
| AR (1) | AR201414A1 (en, 2012) |
| AT (1) | AT340912B (en, 2012) |
| BE (1) | BE824227A (en, 2012) |
| CA (1) | CA1037960A (en, 2012) |
| CH (1) | CH593245A5 (en, 2012) |
| DE (1) | DE2501122C3 (en, 2012) |
| DK (1) | DK137953B (en, 2012) |
| ES (1) | ES433816A1 (en, 2012) |
| FI (1) | FI63746C (en, 2012) |
| FR (1) | FR2257273B1 (en, 2012) |
| GB (1) | GB1462311A (en, 2012) |
| HU (1) | HU168062B (en, 2012) |
| IE (1) | IE40883B1 (en, 2012) |
| IT (1) | IT1044267B (en, 2012) |
| NL (1) | NL166020C (en, 2012) |
| NO (1) | NO137894C (en, 2012) |
| OA (1) | OA04881A (en, 2012) |
| SE (1) | SE422202B (en, 2012) |
| SU (1) | SU545254A3 (en, 2012) |
| YU (1) | YU36495B (en, 2012) |
| ZA (1) | ZA748105B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2422630A1 (fr) * | 1978-04-14 | 1979-11-09 | Synthelabo | Derives de propionamidoxime et leur application en therapeutique |
| FR2506764A1 (fr) * | 1981-05-26 | 1982-12-03 | Synthelabo | Derives d'amidoximes, leur preparation et leur application en therapeutique |
| FR2506767A1 (fr) | 1981-05-26 | 1982-12-03 | Synthelabo | Derives heterocycliques d'amidoximes, leur preparation et leur application en therapeutique |
| JPS58131482A (ja) * | 1982-01-29 | 1983-08-05 | Matsushita Electric Ind Co Ltd | リフト型逆止弁 |
| US4851554A (en) * | 1987-04-06 | 1989-07-25 | University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4806663A (en) * | 1987-04-06 | 1989-02-21 | The University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4831156A (en) * | 1987-09-30 | 1989-05-16 | The University Of Tennessee Research Corp. | 3-substituted 2-alkyl indole derivatives |
| ATE369337T1 (de) * | 2000-04-28 | 2007-08-15 | Asahi Kasei Pharma Corp | Neue bizyklische verbindungen |
-
1974
- 1974-01-15 FR FR7401286A patent/FR2257273B1/fr not_active Expired
- 1974-12-06 US US05/530,076 patent/US3931240A/en not_active Expired - Lifetime
- 1974-12-09 FI FI3536/74A patent/FI63746C/fi active
- 1974-12-11 DK DK645174AA patent/DK137953B/da not_active IP Right Cessation
- 1974-12-17 IE IE2597/74A patent/IE40883B1/xx unknown
- 1974-12-19 ZA ZA00748105A patent/ZA748105B/xx unknown
- 1974-12-27 AR AR257100A patent/AR201414A1/es active
- 1974-12-27 YU YU03498/74A patent/YU36495B/xx unknown
-
1975
- 1975-01-09 BE BE152241A patent/BE824227A/xx not_active IP Right Cessation
- 1975-01-10 GB GB120275A patent/GB1462311A/en not_active Expired
- 1975-01-13 HU HULA853A patent/HU168062B/hu unknown
- 1975-01-14 DE DE2501122A patent/DE2501122C3/de not_active Expired
- 1975-01-14 IT IT19225/75A patent/IT1044267B/it active
- 1975-01-14 NO NO750104A patent/NO137894C/no unknown
- 1975-01-14 CH CH36275A patent/CH593245A5/xx not_active IP Right Cessation
- 1975-01-14 CA CA217,910A patent/CA1037960A/en not_active Expired
- 1975-01-14 NL NL7500399.A patent/NL166020C/xx not_active IP Right Cessation
- 1975-01-14 SU SU2100651A patent/SU545254A3/ru active
- 1975-01-14 SE SE7500360A patent/SE422202B/xx not_active IP Right Cessation
- 1975-01-15 OA OA55386A patent/OA04881A/xx unknown
- 1975-01-15 AT AT26875A patent/AT340912B/de not_active IP Right Cessation
- 1975-01-15 ES ES433816A patent/ES433816A1/es not_active Expired
- 1975-01-16 JP JP765875A patent/JPS541301B2/ja not_active Expired
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