DE1119868B - Verfahren zur Herstellung von basisch substituierten Alkylxanthinderivaten - Google Patents
Verfahren zur Herstellung von basisch substituierten AlkylxanthinderivatenInfo
- Publication number
- DE1119868B DE1119868B DEC18937A DEC0018937A DE1119868B DE 1119868 B DE1119868 B DE 1119868B DE C18937 A DEC18937 A DE C18937A DE C0018937 A DEC0018937 A DE C0018937A DE 1119868 B DE1119868 B DE 1119868B
- Authority
- DE
- Germany
- Prior art keywords
- radical
- general formula
- compounds
- alkylxanthine
- derivatives
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 hydroxyaryl radical Chemical class 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- OQFMNXMRKPNXOY-UHFFFAOYSA-N 1,3-dimethyl-7h-purine-2,6-dione;hydrochloride Chemical compound Cl.O=C1N(C)C(=O)N(C)C2=C1NC=N2 OQFMNXMRKPNXOY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC18937A DE1119868B (de) | 1959-05-05 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Alkylxanthinderivaten |
| CH477460A CH387048A (de) | 1959-05-05 | 1960-04-27 | Verfahren zur Herstellung von 7-Theophyllinderivaten |
| AT327660A AT214939B (de) | 1959-05-05 | 1960-04-29 | Verfahren zur Herstellung von neuen 7-Theophyllinderivaten |
| GB15615/60A GB928186A (en) | 1959-05-05 | 1960-05-03 | 7-theophylline derivatives and a process for their production |
| DK178060AA DK94623C (da) | 1959-05-05 | 1960-05-05 | Fremgangsmåde til fremstilling af 7-teofyllinderivater. |
| FR825868A FR616M (enrdf_load_stackoverflow) | 1959-05-05 | 1960-08-31 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC18937A DE1119868B (de) | 1959-05-05 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Alkylxanthinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1119868B true DE1119868B (de) | 1961-12-21 |
Family
ID=7016532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC18937A Pending DE1119868B (de) | 1959-05-05 | 1959-05-05 | Verfahren zur Herstellung von basisch substituierten Alkylxanthinderivaten |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT214939B (enrdf_load_stackoverflow) |
| CH (1) | CH387048A (enrdf_load_stackoverflow) |
| DE (1) | DE1119868B (enrdf_load_stackoverflow) |
| DK (1) | DK94623C (enrdf_load_stackoverflow) |
| FR (1) | FR616M (enrdf_load_stackoverflow) |
| GB (1) | GB928186A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3414572A (en) * | 1965-09-09 | 1968-12-03 | Gold And Silber Scheideanstalt | Basic substituted alkylxanthine derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1225187B (de) * | 1962-03-27 | 1966-09-22 | Degussa | Verfahren zur Herstellung der linksdrehenden Isomeren von basisch substituierten Alkylxanthinderivaten |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2142935A (en) * | 1937-02-20 | 1939-01-03 | Monsanto Chemicals | Reduction of chlorotheophylline |
-
1959
- 1959-05-05 DE DEC18937A patent/DE1119868B/de active Pending
-
1960
- 1960-04-27 CH CH477460A patent/CH387048A/de unknown
- 1960-04-29 AT AT327660A patent/AT214939B/de active
- 1960-05-03 GB GB15615/60A patent/GB928186A/en not_active Expired
- 1960-05-05 DK DK178060AA patent/DK94623C/da active
- 1960-08-31 FR FR825868A patent/FR616M/fr active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2142935A (en) * | 1937-02-20 | 1939-01-03 | Monsanto Chemicals | Reduction of chlorotheophylline |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3414572A (en) * | 1965-09-09 | 1968-12-03 | Gold And Silber Scheideanstalt | Basic substituted alkylxanthine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| AT214939B (de) | 1961-05-10 |
| GB928186A (en) | 1963-06-12 |
| DK94623C (da) | 1962-10-29 |
| CH387048A (de) | 1965-01-31 |
| FR616M (enrdf_load_stackoverflow) | 1961-06-19 |
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