DE3205149C2 - - Google Patents
Info
- Publication number
- DE3205149C2 DE3205149C2 DE3205149A DE3205149A DE3205149C2 DE 3205149 C2 DE3205149 C2 DE 3205149C2 DE 3205149 A DE3205149 A DE 3205149A DE 3205149 A DE3205149 A DE 3205149A DE 3205149 C2 DE3205149 C2 DE 3205149C2
- Authority
- DE
- Germany
- Prior art keywords
- propanediol
- compound
- theophyllin
- phenylpiperazin
- piperazin
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 14
- 230000000954 anitussive effect Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- -1 4-phenylpiperazin-1-yl Chemical group 0.000 claims 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- 230000002425 cardiocirculatory effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000003434 antitussive agent Substances 0.000 description 2
- 229940124584 antitussives Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 241000700198 Cavia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000035487 diastolic blood pressure Effects 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8109343A IT1210639B (it) | 1981-02-25 | 1981-02-25 | Prodotto: 3(4-fenil1piperazinio-1-il)-1,2-propandiolo 3(teofillin-7-il)-1propansolfonato,utilizzabile in terapia,e relativo procedimento di fabbricazione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3205149A1 DE3205149A1 (de) | 1982-11-11 |
| DE3205149C2 true DE3205149C2 (en, 2012) | 1991-04-18 |
Family
ID=11128724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823205149 Granted DE3205149A1 (de) | 1981-02-25 | 1982-02-13 | 3-(4-phenyl-1-piperazinio-1-yl)-1,2-propandiol-3-(theophyllin-7-yl)-propansulfonat, verfahren zu seiner herstellung und es enthaltende arzneimittel |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4372958A (en, 2012) |
| JP (1) | JPS57188589A (en, 2012) |
| AT (1) | AT380881B (en, 2012) |
| BE (1) | BE892271A (en, 2012) |
| CA (1) | CA1192549A (en, 2012) |
| CH (1) | CH651043A5 (en, 2012) |
| DE (1) | DE3205149A1 (en, 2012) |
| DK (1) | DK148687C (en, 2012) |
| ES (1) | ES8302680A1 (en, 2012) |
| FR (1) | FR2500455A1 (en, 2012) |
| GB (1) | GB2093445B (en, 2012) |
| GR (1) | GR76060B (en, 2012) |
| IT (1) | IT1210639B (en, 2012) |
| LU (1) | LU83962A1 (en, 2012) |
| NL (1) | NL8200746A (en, 2012) |
| PT (1) | PT74463B (en, 2012) |
| SE (1) | SE440503B (en, 2012) |
| YU (1) | YU44007B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IT1217950B (it) * | 1988-06-28 | 1990-03-30 | Dott Formenti Ind Chimica E Fa | Sali di (r,s) 3 (4 fenil 1 piperazinil) 1,2 propandtolo |
| IT1231158B (it) * | 1989-07-20 | 1991-11-19 | Dompe Farmaceutici Spa | Procedimento per la risoluzione ottica della dropropizina. |
| DE3938123A1 (de) * | 1989-11-16 | 1991-05-23 | Diehl Gmbh & Co | Treibladungsanzuender |
| IT1318651B1 (it) * | 2000-07-28 | 2003-08-27 | Dompe Spa | Sintesi di (+-)1,3-diossolani e loro risoluzione ottica. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163649A (en) * | 1964-12-29 | Substituteb phenyl-piperazine | ||
| GB938646A (en) * | 1961-03-16 | 1963-10-02 | Henri Morren | New piperazine derivatives |
| FR1384693A (fr) * | 1963-10-08 | 1965-01-08 | Electrochimie Soc | Procédé de préparation d'esters méthallyliques |
| FR1554628A (en, 2012) * | 1967-05-23 | 1969-01-24 |
-
1981
- 1981-02-25 IT IT8109343A patent/IT1210639B/it active
- 1981-05-22 GB GB8115803A patent/GB2093445B/en not_active Expired
- 1981-06-10 US US06/272,281 patent/US4372958A/en not_active Expired - Fee Related
-
1982
- 1982-02-13 DE DE19823205149 patent/DE3205149A1/de active Granted
- 1982-02-17 AT AT0059982A patent/AT380881B/de not_active IP Right Cessation
- 1982-02-19 PT PT74463A patent/PT74463B/pt unknown
- 1982-02-23 LU LU83962A patent/LU83962A1/fr unknown
- 1982-02-23 GR GR67396A patent/GR76060B/el unknown
- 1982-02-24 YU YU412/82A patent/YU44007B/xx unknown
- 1982-02-24 JP JP57027570A patent/JPS57188589A/ja active Granted
- 1982-02-24 ES ES509850A patent/ES8302680A1/es not_active Expired
- 1982-02-24 CA CA000397008A patent/CA1192549A/en not_active Expired
- 1982-02-24 DK DK79982A patent/DK148687C/da active
- 1982-02-24 NL NL8200746A patent/NL8200746A/nl not_active Application Discontinuation
- 1982-02-25 CH CH1167/82A patent/CH651043A5/it not_active IP Right Cessation
- 1982-02-25 FR FR8203164A patent/FR2500455A1/fr active Granted
- 1982-02-25 SE SE8201184A patent/SE440503B/sv not_active IP Right Cessation
- 1982-02-25 BE BE0/207403A patent/BE892271A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3205149A1 (de) | 1982-11-11 |
| SE440503B (sv) | 1985-08-05 |
| FR2500455A1 (fr) | 1982-08-27 |
| AT380881B (de) | 1986-07-25 |
| BE892271A (fr) | 1982-06-16 |
| YU44007B (en) | 1990-02-28 |
| GB2093445B (en) | 1985-02-27 |
| DK148687C (da) | 1986-04-28 |
| PT74463B (en) | 1983-08-24 |
| CA1192549A (en) | 1985-08-27 |
| IT1210639B (it) | 1989-09-14 |
| FR2500455B1 (en, 2012) | 1984-04-27 |
| SE8201184L (sv) | 1982-08-26 |
| PT74463A (en) | 1982-03-01 |
| ES509850A0 (es) | 1983-02-01 |
| JPS57188589A (en) | 1982-11-19 |
| CH651043A5 (it) | 1985-08-30 |
| IT8109343A0 (it) | 1981-02-25 |
| JPH0333715B2 (en, 2012) | 1991-05-20 |
| GB2093445A (en) | 1982-09-02 |
| ATA59982A (de) | 1985-12-15 |
| US4372958A (en) | 1983-02-08 |
| DK79982A (da) | 1982-08-26 |
| NL8200746A (nl) | 1982-09-16 |
| ES8302680A1 (es) | 1983-02-01 |
| DK148687B (da) | 1985-09-02 |
| LU83962A1 (fr) | 1982-07-08 |
| YU41282A (en) | 1987-10-31 |
| GR76060B (en, 2012) | 1984-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |