DE3212909A1 - 7-(2-diaethylaminoaethyl)-theophyllin-acetylsalicylat und verfahren zu seiner herstellung - Google Patents
7-(2-diaethylaminoaethyl)-theophyllin-acetylsalicylat und verfahren zu seiner herstellungInfo
- Publication number
- DE3212909A1 DE3212909A1 DE19823212909 DE3212909A DE3212909A1 DE 3212909 A1 DE3212909 A1 DE 3212909A1 DE 19823212909 DE19823212909 DE 19823212909 DE 3212909 A DE3212909 A DE 3212909A DE 3212909 A1 DE3212909 A1 DE 3212909A1
- Authority
- DE
- Germany
- Prior art keywords
- theophylline
- solvent
- diethylaminoethyl
- effect
- acetone
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 229940068372 acetyl salicylate Drugs 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 10
- AWKLBIOQCIORSB-UHFFFAOYSA-N etamiphylline Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCN(CC)CC AWKLBIOQCIORSB-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 208000009989 Posterior Leukoencephalopathy Syndrome Diseases 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 229960004592 isopropanol Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 description 12
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- -1 2-diethylaminoethyl Chemical group 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 210000001772 blood platelet Anatomy 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- 230000024883 vasodilation Effects 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- OHXPGWPVLFPUSM-KLRNGDHRSA-N 3,7,12-trioxo-5beta-cholanic acid Chemical compound C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C OHXPGWPVLFPUSM-KLRNGDHRSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N 3-methyl-2-pentanone Chemical compound CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 241000157855 Cinchona Species 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- 229950006790 adenosine phosphate Drugs 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940009979 dehydrocholate Drugs 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960000505 etamiphylline Drugs 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000002267 hypothalamic effect Effects 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 125000003410 quininyl group Chemical group 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
Classifications
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES501162A ES501162A0 (es) | 1981-04-07 | 1981-04-07 | Procedimiento para la obtencion de acetilsalicilato de 7-(2-dietilaminoetil)-teofilina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3212909A1 true DE3212909A1 (de) | 1982-11-18 |
| DE3212909C2 DE3212909C2 (en)) | 1990-07-26 |
Family
ID=8482205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823212909 Granted DE3212909A1 (de) | 1981-04-07 | 1982-04-06 | 7-(2-diaethylaminoaethyl)-theophyllin-acetylsalicylat und verfahren zu seiner herstellung |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH647780A5 (en)) |
| DE (1) | DE3212909A1 (en)) |
| ES (1) | ES501162A0 (en)) |
| GB (1) | GB2096138B (en)) |
| IT (1) | IT1153967B (en)) |
| PT (1) | PT74716B (en)) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3508097A1 (de) * | 1984-07-21 | 1986-02-06 | Hoechst Ag, 6230 Frankfurt | Kombinationspraeparat aus xanthinderivaten und o-acetylsalicylsaeure bzw. deren pharmakologisch vertraeglichen salzen und dessen verwendung |
| ES2009604A6 (es) * | 1988-05-05 | 1989-10-01 | Coma Julia Concepcion | Procedimiento de obtencion de acetil-salicilato de 7-(2-dietilaminoetil)-teofilina. |
| AU144901S (en) | 2001-03-02 | 2001-08-15 | Nokia Mobile Phones Ltd | A handset |
| CA97021S (en) | 2001-03-02 | 2003-06-25 | Nokia Mobile Phones Ltd | Handset |
| AU144902S (en) | 2001-03-02 | 2001-08-15 | Nokia Mobile Phones Ltd | A handset |
| AU144906S (en) | 2001-03-02 | 2001-08-15 | Nokia Mobile Phones Ltd | A handset |
-
1981
- 1981-04-07 ES ES501162A patent/ES501162A0/es active Granted
-
1982
- 1982-03-17 GB GB8207789A patent/GB2096138B/en not_active Expired
- 1982-03-22 CH CH1743/82A patent/CH647780A5/de not_active IP Right Cessation
- 1982-03-30 IT IT20487/82A patent/IT1153967B/it active
- 1982-04-06 PT PT74716A patent/PT74716B/pt unknown
- 1982-04-06 DE DE19823212909 patent/DE3212909A1/de active Granted
Non-Patent Citations (1)
| Title |
|---|
| Arzneim.forschung, 21, 1971, 354-358 * |
Also Published As
| Publication number | Publication date |
|---|---|
| PT74716A (en) | 1982-05-01 |
| CH647780A5 (de) | 1985-02-15 |
| ES8202009A1 (es) | 1982-02-01 |
| IT8220487A0 (it) | 1982-03-30 |
| ES501162A0 (es) | 1982-02-01 |
| PT74716B (en) | 1983-11-14 |
| GB2096138A (en) | 1982-10-13 |
| GB2096138B (en) | 1984-08-01 |
| IT1153967B (it) | 1987-01-21 |
| DE3212909C2 (en)) | 1990-07-26 |
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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 |