DE1445602C3 - Verfahren zur Herstellung von 2',3\ 5',-Tri-O-acetyl-6-azauridin - Google Patents
Verfahren zur Herstellung von 2',3\ 5',-Tri-O-acetyl-6-azauridinInfo
- Publication number
- DE1445602C3 DE1445602C3 DE19631445602 DE1445602A DE1445602C3 DE 1445602 C3 DE1445602 C3 DE 1445602C3 DE 19631445602 DE19631445602 DE 19631445602 DE 1445602 A DE1445602 A DE 1445602A DE 1445602 C3 DE1445602 C3 DE 1445602C3
- Authority
- DE
- Germany
- Prior art keywords
- azauridine
- acetyl
- tri
- acid
- reaction
- 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
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 27
- WYXSYVWAUAUWLD-SHUUEZRQSA-N 6-azauridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=N1 WYXSYVWAUAUWLD-SHUUEZRQSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- -1 acetyl halides Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- QQOBRRFOVWGIMD-OJAKKHQRSA-N azaribine Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1N1C(=O)NC(=O)C=N1 QQOBRRFOVWGIMD-OJAKKHQRSA-N 0.000 claims description 6
- 230000021736 acetylation Effects 0.000 claims description 5
- 238000006640 acetylation reaction Methods 0.000 claims description 5
- 229950010054 azaribine Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000003729 cation exchange resin Substances 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000012262 fermentative production Methods 0.000 claims description 2
- 230000035876 healing Effects 0.000 claims description 2
- 239000002777 nucleoside Substances 0.000 claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 5
- 150000001298 alcohols Chemical class 0.000 claims 4
- 238000007171 acid catalysis Methods 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000003835 nucleoside group Chemical group 0.000 claims 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000032050 esterification Effects 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- GCVZNVTXNUTBFB-XNIJJKJLSA-N [(2r,3r,4r,5r)-3,4-diacetyloxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate Chemical group CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 GCVZNVTXNUTBFB-XNIJJKJLSA-N 0.000 claims 1
- 230000000397 acetylating effect Effects 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 230000003327 cancerostatic effect Effects 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002561 ketenes Chemical class 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 230000008092 positive effect Effects 0.000 claims 1
- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 239000012345 acetylating agent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MHNNLDVYCJWTGQ-VPCXQMTMSA-N 2-[(2S,3R,4S,5R)-2-acetyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazine-3,5-dione Chemical compound N1=CC(=O)NC(=O)N1[C@]1(C(=O)C)O[C@H](CO)[C@@H](O)[C@H]1O MHNNLDVYCJWTGQ-VPCXQMTMSA-N 0.000 description 1
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical compound O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960005010 orotic acid Drugs 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/12—Triazine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS618662 | 1962-11-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1445602A1 DE1445602A1 (de) | 1969-03-20 |
| DE1445602B2 DE1445602B2 (de) | 1974-03-21 |
| DE1445602C3 true DE1445602C3 (de) | 1974-10-17 |
Family
ID=5408305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631445602 Expired DE1445602C3 (de) | 1962-11-01 | 1963-10-30 | Verfahren zur Herstellung von 2',3\ 5',-Tri-O-acetyl-6-azauridin |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT261124B (Direct) |
| CH (1) | CH449637A (Direct) |
| DE (1) | DE1445602C3 (Direct) |
| DK (1) | DK133953B (Direct) |
| FI (1) | FI46387C (Direct) |
| GB (1) | GB999084A (Direct) |
| NL (1) | NL139975B (Direct) |
| SE (1) | SE321480B (Direct) |
-
1963
- 1963-10-28 CH CH1319763A patent/CH449637A/de unknown
- 1963-10-28 NL NL299823A patent/NL139975B/xx unknown
- 1963-10-30 FI FI212963A patent/FI46387C/fi active
- 1963-10-30 DE DE19631445602 patent/DE1445602C3/de not_active Expired
- 1963-10-31 AT AT873263A patent/AT261124B/de active
- 1963-10-31 SE SE1201663A patent/SE321480B/xx unknown
- 1963-11-01 DK DK514263A patent/DK133953B/da unknown
- 1963-11-01 GB GB4314163A patent/GB999084A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH449637A (de) | 1968-01-15 |
| SE321480B (Direct) | 1970-03-09 |
| AT261124B (de) | 1968-04-10 |
| DE1445602B2 (de) | 1974-03-21 |
| FI46387B (Direct) | 1972-11-30 |
| DK133953B (da) | 1976-08-16 |
| DE1445602A1 (de) | 1969-03-20 |
| DK133953C (Direct) | 1977-01-24 |
| FI46387C (fi) | 1973-03-12 |
| NL139975B (nl) | 1973-10-15 |
| GB999084A (en) | 1965-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |