CH496013A - Verfahren zur Herstellung von neuen substituierten Aminen und deren Verwendung - Google Patents
Verfahren zur Herstellung von neuen substituierten Aminen und deren VerwendungInfo
- Publication number
- CH496013A CH496013A CH1755266A CH1755266A CH496013A CH 496013 A CH496013 A CH 496013A CH 1755266 A CH1755266 A CH 1755266A CH 1755266 A CH1755266 A CH 1755266A CH 496013 A CH496013 A CH 496013A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compound
- alkyl group
- hydrogen atom
- compounds
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 6
- 230000000747 cardiac effect Effects 0.000 title abstract 2
- 230000000694 effects Effects 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229960000278 theophylline Drugs 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 229960004559 theobromine Drugs 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 229960004767 proxyphylline Drugs 0.000 abstract description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- -1 chlorohydroxypropyl theophylline Chemical compound 0.000 description 2
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 2
- 229960000395 phenylpropanolamine Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 1
- KYHQZNGJUGFTGR-UHFFFAOYSA-N Proxyphylline Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CC(O)C KYHQZNGJUGFTGR-UHFFFAOYSA-N 0.000 description 1
- 206010062119 Sympathomimetic effect Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001975 sympathomimetic effect Effects 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
- 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
- C07D473/10—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 3 and 7, e.g. theobromine
-
- 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
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1111865A AT269171B (de) | 1965-12-10 | 1965-12-10 | Verfahren zur Herstellung von neuen substituierten Aminen und deren Salzen |
| AT272766A AT270673B (de) | 1966-03-22 | 1966-03-22 | Verfahren zur Herstellung von neuen substituierten Aminen oder deren Salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH496013A true CH496013A (de) | 1970-09-15 |
Family
ID=25598985
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1755266A CH496013A (de) | 1965-12-10 | 1966-12-08 | Verfahren zur Herstellung von neuen substituierten Aminen und deren Verwendung |
| CH991470A CH496014A (de) | 1965-12-10 | 1966-12-08 | Verfahren zur Herstellung von neuen substituierten Aminen und deren Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH991470A CH496014A (de) | 1965-12-10 | 1966-12-08 | Verfahren zur Herstellung von neuen substituierten Aminen und deren Verwendung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5113160B1 (enrdf_load_stackoverflow) |
| BE (1) | BE690863A (enrdf_load_stackoverflow) |
| CH (2) | CH496013A (enrdf_load_stackoverflow) |
| DE (1) | DE1695100A1 (enrdf_load_stackoverflow) |
| ES (1) | ES334064A1 (enrdf_load_stackoverflow) |
| FR (2) | FR1504939A (enrdf_load_stackoverflow) |
| GB (1) | GB1156719A (enrdf_load_stackoverflow) |
| SE (1) | SE345669B (enrdf_load_stackoverflow) |
-
1966
- 1966-11-30 DE DE19661695100 patent/DE1695100A1/de active Pending
- 1966-12-02 ES ES0334064A patent/ES334064A1/es not_active Expired
- 1966-12-08 CH CH1755266A patent/CH496013A/de not_active IP Right Cessation
- 1966-12-08 SE SE16834/66A patent/SE345669B/xx unknown
- 1966-12-08 CH CH991470A patent/CH496014A/de not_active IP Right Cessation
- 1966-12-08 JP JP41080097A patent/JPS5113160B1/ja active Pending
- 1966-12-08 BE BE690863D patent/BE690863A/xx unknown
- 1966-12-09 GB GB55188/66A patent/GB1156719A/en not_active Expired
- 1966-12-09 FR FR86792A patent/FR1504939A/fr not_active Expired
-
1967
- 1967-03-09 FR FR98053A patent/FR7018M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES334064A1 (es) | 1967-10-16 |
| CH496014A (de) | 1970-09-15 |
| JPS5113160B1 (enrdf_load_stackoverflow) | 1976-04-26 |
| FR1504939A (fr) | 1967-12-08 |
| DE1695100A1 (de) | 1970-12-10 |
| GB1156719A (en) | 1969-07-02 |
| BE690863A (enrdf_load_stackoverflow) | 1967-06-08 |
| SE345669B (enrdf_load_stackoverflow) | 1972-06-05 |
| FR7018M (enrdf_load_stackoverflow) | 1969-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |