LU87538A1 - Procede de preparation de la levo-dropropizine et de la dextro-dropropizine - Google Patents
Procede de preparation de la levo-dropropizine et de la dextro-dropropizine Download PDFInfo
- Publication number
- LU87538A1 LU87538A1 LU87538A LU87538A LU87538A1 LU 87538 A1 LU87538 A1 LU 87538A1 LU 87538 A LU87538 A LU 87538A LU 87538 A LU87538 A LU 87538A LU 87538 A1 LU87538 A1 LU 87538A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- dropropizine
- levo
- dextro
- preparation
- glycidol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- PTVWPYVOOKLBCG-ZDUSSCGKSA-N levodropropizine Chemical compound C1CN(C[C@H](O)CO)CCN1C1=CC=CC=C1 PTVWPYVOOKLBCG-ZDUSSCGKSA-N 0.000 title claims description 8
- 229960002265 levodropropizine Drugs 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- PTVWPYVOOKLBCG-CYBMUJFWSA-N (2r)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol Chemical compound C1CN(C[C@@H](O)CO)CCN1C1=CC=CC=C1 PTVWPYVOOKLBCG-CYBMUJFWSA-N 0.000 title claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- CTKINSOISVBQLD-VKHMYHEASA-N (S)-Glycidol Chemical compound OC[C@H]1CO1 CTKINSOISVBQLD-VKHMYHEASA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229960004722 dropropizine Drugs 0.000 claims description 8
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- CTKINSOISVBQLD-GSVOUGTGSA-N (R)-Glycidol Chemical compound OC[C@@H]1CO1 CTKINSOISVBQLD-GSVOUGTGSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229960004592 isopropanol Drugs 0.000 claims 1
- PTVWPYVOOKLBCG-UHFFFAOYSA-N 3-(4-phenyl-1-piperazinyl)propane-1,2-diol Chemical compound C1CN(CC(O)CO)CCN1C1=CC=CC=C1 PTVWPYVOOKLBCG-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- DFQNMODTAFTGHS-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCC(O)CO)C=C1 DFQNMODTAFTGHS-UHFFFAOYSA-N 0.000 description 2
- -1 4-phenylpiperazin-l-yl Chemical group 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004146 Propane-1,2-diol Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- LHUBFUMPYZCAER-UHFFFAOYSA-N CCCN(CCNC)c1ccccc1 Chemical compound CCCN(CCNC)c1ccccc1 LHUBFUMPYZCAER-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- AELLFKPPLQHPRV-UHFFFAOYSA-N n-propan-2-yl-7-propan-2-yliminocyclohepta-1,3,5-trien-1-amine Chemical compound CC(C)NC1=CC=CC=CC1=NC(C)C AELLFKPPLQHPRV-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2161188 | 1988-08-01 | ||
| IT8821611A IT1226570B (it) | 1988-08-01 | 1988-08-01 | Procedimento di preparazione della levo- e destro-dropropizina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87538A1 true LU87538A1 (fr) | 1991-02-18 |
Family
ID=11184306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87538A LU87538A1 (fr) | 1988-08-01 | 1989-06-14 | Procede de preparation de la levo-dropropizine et de la dextro-dropropizine |
Country Status (5)
| Country | Link |
|---|---|
| ES (1) | ES2014187A6 (it) |
| FR (1) | FR2634765B1 (it) |
| IT (1) | IT1226570B (it) |
| LU (1) | LU87538A1 (it) |
| NL (1) | NL8901701A (it) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1231158B (it) * | 1989-07-20 | 1991-11-19 | Dompe Farmaceutici Spa | Procedimento per la risoluzione ottica della dropropizina. |
| IT1254452B (it) * | 1992-02-14 | 1995-09-25 | Dompe Farmaceutici Spa | N-ossidi ed n,n'-diossidi di 3-(piperazin-1-il)-propan-1,2-dioli |
| IT1254993B (it) * | 1992-06-24 | 1995-10-11 | Procedimento per la preparazione degli enantiomeri della dropropizina | |
| IT1318650B1 (it) * | 2000-07-28 | 2003-08-27 | Dompe Spa | 1,3-diossolani ad attivita' antitosse. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB938646A (en) * | 1961-03-16 | 1963-10-02 | Henri Morren | New piperazine derivatives |
| IT1203721B (it) * | 1983-12-29 | 1989-02-23 | Dompe Farmaceutici Spa | Composti otticamente attivi ad attivita' antitosse e sedativa centrale,procedimento per la preparazione e composizioni che li contengono |
| NL8801622A (nl) * | 1988-06-25 | 1990-01-16 | Stamicarbon | Bereiding van enantiomeren van dropropizine. |
-
1988
- 1988-08-01 IT IT8821611A patent/IT1226570B/it active
-
1989
- 1989-05-18 FR FR8906484A patent/FR2634765B1/fr not_active Expired - Lifetime
- 1989-06-14 LU LU87538A patent/LU87538A1/fr unknown
- 1989-07-04 NL NL8901701A patent/NL8901701A/nl not_active Application Discontinuation
- 1989-07-31 ES ES8902707A patent/ES2014187A6/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL8901701A (nl) | 1990-03-01 |
| FR2634765B1 (fr) | 1994-05-27 |
| IT8821611A0 (it) | 1988-08-01 |
| FR2634765A1 (fr) | 1990-02-02 |
| IT1226570B (it) | 1991-01-24 |
| ES2014187A6 (es) | 1990-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DT | Application date | ||
| TA | Annual fee |