ES360636A1 - Improvements in or relating to mandelamidine derivatives - Google Patents
Improvements in or relating to mandelamidine derivativesInfo
- Publication number
- ES360636A1 ES360636A1 ES360636A ES360636A ES360636A1 ES 360636 A1 ES360636 A1 ES 360636A1 ES 360636 A ES360636 A ES 360636A ES 360636 A ES360636 A ES 360636A ES 360636 A1 ES360636 A1 ES 360636A1
- Authority
- ES
- Spain
- Prior art keywords
- reaction
- compound
- compounds
- prepared
- addition salts
- 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
- AFXGCWGNLJLYEZ-UHFFFAOYSA-N 2-hydroxy-2-phenylethanimidamide Chemical class NC(=N)C(O)C1=CC=CC=C1 AFXGCWGNLJLYEZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- JWZKLCWLXKKOLL-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-2-hydroxyacetonitrile Chemical compound N#CC(O)C1=CC=C2OCOC2=C1 JWZKLCWLXKKOLL-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 229940125890 compound Ia Drugs 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 150000002463 imidates Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229940081310 piperonal Drugs 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
Classifications
-
- 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
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises compounds of formula whesein either R 3 and R 4 are each selected from hydrogen, alkyl and aryl(compounds Ia)orR 3 is H and R 4 is OH (compound Ib) arid their addition salts with physiologically acceptable acids. Compounds Ia are prepared from 3,4-methylenedioxymandelonitrile by reaction with an aliphatic alcohol and reaction of the resulting imido-ester with a compound NHR 3 gR 4 ,. Compound Ib is prepared from compound Ia (wherein R 3 = R 4 = H) by reaction with hydroxylamine. 3,4 - Methylenedioxy - mandelonitrile is prepared from piperonal by reaction with KCN in an aqueous medium in the presence of sodium bisulphite and hydrochloric and at a pH 4.0- 5-0 using a sealed reaction apparatus. Compounds of the above formula and their addition salts with physiologically acceptable acids are stated to counteract arterial hypotension and may be made up with carriers into pharmaceutical compositions for oral, buccal and parenteral administration.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5443067 | 1967-11-29 | ||
| GB34947/68A GB1243186A (en) | 1967-11-29 | 1967-11-29 | Improvements in or relating to mandelamidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES360636A1 true ES360636A1 (en) | 1970-10-16 |
Family
ID=26262509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES360636A Expired ES360636A1 (en) | 1967-11-29 | 1968-11-23 | Improvements in or relating to mandelamidine derivatives |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE723974A (en) |
| CH (1) | CH488651A (en) |
| DE (1) | DE1817861C3 (en) |
| ES (1) | ES360636A1 (en) |
| FR (2) | FR1591540A (en) |
| GB (1) | GB1243186A (en) |
| NL (1) | NL162909C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1121792B (en) * | 1978-07-03 | 1986-04-23 | Dow Chemical Co | A PROCESS TO PREPARE 2-NAPHTHALENETHANIMIDAMIDS N, N'-OF-SUBSTITUTES AND INTERMEDIATES USED IN THIS PROCESS |
| US4623659A (en) * | 1983-05-23 | 1986-11-18 | Riet Bartholomeus Van T | Polyhydroxybenzoic acid derivatives |
-
1967
- 1967-11-29 GB GB34947/68A patent/GB1243186A/en not_active Expired
-
1968
- 1968-11-14 FR FR1591540D patent/FR1591540A/fr not_active Expired
- 1968-11-14 FR FR173695A patent/FR7744M/fr not_active Expired
- 1968-11-15 CH CH1708868A patent/CH488651A/en not_active IP Right Cessation
- 1968-11-18 BE BE723974D patent/BE723974A/xx not_active IP Right Cessation
- 1968-11-23 ES ES360636A patent/ES360636A1/en not_active Expired
- 1968-11-27 NL NL6816939A patent/NL162909C/en active
- 1968-11-29 DE DE19681817861 patent/DE1817861C3/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE723974A (en) | 1969-05-19 |
| GB1243186A (en) | 1971-08-18 |
| FR7744M (en) | 1970-03-09 |
| NL162909C (en) | 1980-07-15 |
| FR1591540A (en) | 1970-04-27 |
| DE1817861B2 (en) | 1973-09-06 |
| DE1817861C3 (en) | 1974-04-04 |
| DE1817861A1 (en) | 1972-09-28 |
| DE1811804A1 (en) | 1969-11-27 |
| CH488651A (en) | 1970-04-15 |
| NL6816939A (en) | 1969-06-02 |
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