FR2134218A1 - Phloroglucinol aminoketones - vasodilators and antispasmodics - Google Patents
Phloroglucinol aminoketones - vasodilators and antispasmodicsInfo
- Publication number
- FR2134218A1 FR2134218A1 FR7115024A FR7115024A FR2134218A1 FR 2134218 A1 FR2134218 A1 FR 2134218A1 FR 7115024 A FR7115024 A FR 7115024A FR 7115024 A FR7115024 A FR 7115024A FR 2134218 A1 FR2134218 A1 FR 2134218A1
- Authority
- FR
- France
- Prior art keywords
- phloroglucinol
- alkyl
- aminoketones
- antispasmodics
- vasodilators
- 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
- 230000002921 anti-spasmodic effect Effects 0.000 title 1
- 229940124575 antispasmodic agent Drugs 0.000 title 1
- MLCHZLKLWHXFMY-UHFFFAOYSA-N benzene-1,3,5-triol;urea Chemical class NC(N)=O.OC1=CC(O)=CC(O)=C1 MLCHZLKLWHXFMY-UHFFFAOYSA-N 0.000 title 1
- 229940124549 vasodilator Drugs 0.000 title 1
- 239000003071 vasodilator agent Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000003309 Hoesch reaction Methods 0.000 abstract 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- -1 aminoalkyl nitrile Chemical class 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 150000004658 ketimines Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 abstract 1
- 229960001553 phloroglucinol Drugs 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 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
- C07D295/10—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 doubly bound oxygen or sulphur atoms
- C07D295/104—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Title cpds. are of formula (I): where R1, R2, R3 = H or alkyl, pref. 1-5C; R4, R5 = H, alkyl (pref. 1-5C) or, together with the N atom, form a 5-7 membered heterocycle which may contain further heteroatoms (O, N or S) and may be substd. by alkyl, aryl, amino, aminoalkyl, OH, hydroxyalkyl, anilide or N-substd. amidoalkyl; n = 1-4). The cpds. may be prepd. by a Houben-Hoesch reaction of the appropriate phloroglucinol deriv. with an aminoalkyl nitrile followed by hydrolysis of the ketimine formed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7115024A FR2134218A1 (en) | 1971-04-27 | 1971-04-27 | Phloroglucinol aminoketones - vasodilators and antispasmodics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7115024A FR2134218A1 (en) | 1971-04-27 | 1971-04-27 | Phloroglucinol aminoketones - vasodilators and antispasmodics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2134218A1 true FR2134218A1 (en) | 1972-12-08 |
| FR2134218B1 FR2134218B1 (en) | 1974-08-30 |
Family
ID=9076017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7115024A Granted FR2134218A1 (en) | 1971-04-27 | 1971-04-27 | Phloroglucinol aminoketones - vasodilators and antispasmodics |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2134218A1 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2404003A1 (en) * | 1977-09-26 | 1979-04-20 | Lafon Labor | NEW DERIVATIVES OF PHLOROGLUCINOL, THEIR PROCESS FOR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS |
| EP0063075A1 (en) * | 1981-04-15 | 1982-10-20 | LABORATOIRE L. LAFON Société anonyme dite: | (2,6-Dimethoxy-4-hydroxyphenyl)-(3-piperidinopropyl) ketone and its salts, its use in therapeutic preparations and process for its production |
| FR2534916A1 (en) * | 1982-10-26 | 1984-04-27 | Lafon Labor | NOVEL PHENYL- (3-AMINOPROPYL) -CETONE DERIVATIVES, THERAPEUTIC USE AND PREPARATION METHOD |
| EP0183002A1 (en) * | 1984-10-26 | 1986-06-04 | Laboratorio Italiano Biochimico Farmaceutico Lisapharma S.P.A. | Pharmaceutically active salt derivative of 3-hydroxy -5-(hydroxymethyl)-2-methylisonicotinaldehyde phosphate |
| EP0490769A1 (en) * | 1990-12-12 | 1992-06-17 | Laboratoire L. Lafon | Aminoalkylketone derivatives, process for their preparation and their therapeutical use |
| US5280020A (en) * | 1988-11-16 | 1994-01-18 | Sergio Bertini Curri | Drug and method for increasing the microcirculatory flow-rate and volume in the capillaries to the skin |
| WO2006137335A1 (en) * | 2005-06-20 | 2006-12-28 | Otsuka Pharmaceutical Co., Ltd. | Process for producing piperazine derivative |
-
1971
- 1971-04-27 FR FR7115024A patent/FR2134218A1/en active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2404003A1 (en) * | 1977-09-26 | 1979-04-20 | Lafon Labor | NEW DERIVATIVES OF PHLOROGLUCINOL, THEIR PROCESS FOR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS |
| JPS5495562A (en) * | 1977-09-26 | 1979-07-28 | Lafon Labor | Novel phloroglucine derivative*its manufacture and use as medicine |
| EP0063075A1 (en) * | 1981-04-15 | 1982-10-20 | LABORATOIRE L. LAFON Société anonyme dite: | (2,6-Dimethoxy-4-hydroxyphenyl)-(3-piperidinopropyl) ketone and its salts, its use in therapeutic preparations and process for its production |
| FR2504136A1 (en) * | 1981-04-15 | 1982-10-22 | Lafon Labor | (2,6-DIMETHOXY-4-HYDROXYPHENYL) - (3-PIPERIDINOPROPYL) -CETONE AND ITS ADDITION SALTS, THERAPEUTIC USE AND PREPARATION METHOD |
| FR2534916A1 (en) * | 1982-10-26 | 1984-04-27 | Lafon Labor | NOVEL PHENYL- (3-AMINOPROPYL) -CETONE DERIVATIVES, THERAPEUTIC USE AND PREPARATION METHOD |
| EP0110748A1 (en) * | 1982-10-26 | 1984-06-13 | LABORATOIRE L. LAFON Société anonyme dite: | Derivatives of phenyl-(3-aminopropyl) ketone, their therapeutical use and process for their preparation |
| EP0183002A1 (en) * | 1984-10-26 | 1986-06-04 | Laboratorio Italiano Biochimico Farmaceutico Lisapharma S.P.A. | Pharmaceutically active salt derivative of 3-hydroxy -5-(hydroxymethyl)-2-methylisonicotinaldehyde phosphate |
| US5280020A (en) * | 1988-11-16 | 1994-01-18 | Sergio Bertini Curri | Drug and method for increasing the microcirculatory flow-rate and volume in the capillaries to the skin |
| EP0490769A1 (en) * | 1990-12-12 | 1992-06-17 | Laboratoire L. Lafon | Aminoalkylketone derivatives, process for their preparation and their therapeutical use |
| FR2670492A1 (en) * | 1990-12-12 | 1992-06-19 | Lafon Labor | NOVEL AMINOALKYLCETONE DERIVATIVES, PROCESS FOR PREPARING THEM AND THERAPEUTIC USES THEREOF. |
| US5446060A (en) * | 1990-12-12 | 1995-08-29 | Laboratoire L. Lafon | Aminoalkyl thienyl ketone derivatives and their use as peripheral vasodilators |
| WO2006137335A1 (en) * | 2005-06-20 | 2006-12-28 | Otsuka Pharmaceutical Co., Ltd. | Process for producing piperazine derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2134218B1 (en) | 1974-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transmission of property | ||
| TP | Transmission of property | ||
| CC | Supplementary certificate of protection laid open to the public (law of 25 june 1990) |
Free format text: 92C0025, 920219 |
|
| CB | Supplementary certificate of protection granted (law of 25 june 1990) |
Free format text: 92C0025, 710427 |
|
| CP | Supplementary certificate of protection filed |