CH385860A - Verfahren zur Herstellung von heterocyclischen Verbindungen - Google Patents

Verfahren zur Herstellung von heterocyclischen Verbindungen

Info

Publication number: CH385860A
Authority: CH; Switzerland
Prior art keywords: deoxy; mercury; ribofuranosyl; solution; added
Prior art date: 1959-01-16

Application number

CH8212659A

Other languages

German (de)

English (en)

Inventor

Hoffer Max

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1959-01-16

Filing date

1959-12-21

Publication date

1964-12-31

1959-04-21 Priority claimed from US807769A external-priority patent/US2949451A/en

1959-12-21 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1964-12-31 Publication of CH385860A publication Critical patent/CH385860A/de

Links

238000000034 method Methods 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title claims description 6
150000002391 heterocyclic compounds Chemical class 0.000 title description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 84
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Natural products O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 claims description 20
FNDGOEUDYKWAIX-UHFFFAOYSA-N (5-fluoro-2,4-dioxo-1H-pyrimidin-6-yl)mercury Chemical compound FC=1C(NC(NC=1[Hg])=O)=O FNDGOEUDYKWAIX-UHFFFAOYSA-N 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 15
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
229910052788 barium Inorganic materials 0.000 claims description 14
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 14
229960002949 fluorouracil Drugs 0.000 claims description 12
229940104230 thymidine Drugs 0.000 claims description 12
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 claims description 10
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 claims description 10
239000002244 precipitate Substances 0.000 claims description 10
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 10
238000010992 reflux Methods 0.000 claims description 9
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 7
229910052753 mercury Inorganic materials 0.000 claims description 7
TYJDMPCSWMQKDY-UHFFFAOYSA-N (2,4-dioxo-1H-pyrimidin-5-yl)methylmercury Chemical compound N1C(=O)NC(=O)C(C[Hg])=C1 TYJDMPCSWMQKDY-UHFFFAOYSA-N 0.000 claims description 6
-1 3, 5-di- (p-toluyl) -2-deoxy-D-ribofuranosyl halide Chemical class 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
229940113082 thymine Drugs 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 5
ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 claims description 4
229940100892 mercury compound Drugs 0.000 claims description 4
150000002731 mercury compounds Chemical class 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
239000007859 condensation product Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
239000000243 solution Substances 0.000 description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
238000002844 melting Methods 0.000 description 26
230000008018 melting Effects 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 14
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
239000006188 syrup Substances 0.000 description 9
235000020357 syrup Nutrition 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000000463 material Substances 0.000 description 8
OVGDAVVFKDPXIC-UHFFFAOYSA-N 1-acetyl-5-fluoropyrimidine-2,4-dione Chemical compound CC(=O)N1C=C(F)C(=O)NC1=O OVGDAVVFKDPXIC-UHFFFAOYSA-N 0.000 description 7
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
MNMWOOMYSYOLBE-UHFFFAOYSA-N bis(3-acetyl-5-fluoro-2,6-dioxopyrimidin-4-yl)mercury Chemical compound C(C)(=O)N1C(=O)NC(=O)C(=C1[Hg]C1=C(C(NC(N1C(C)=O)=O)=O)F)F MNMWOOMYSYOLBE-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 5
ODZHZJDDQBXYIF-CSODTCANSA-N (2r,3r)-5-chloro-2-[hydroxy-(4-methylphenyl)methyl]-3-(4-methylphenyl)oxolan-3-ol Chemical compound C1=CC(C)=CC=C1C(O)[C@@H]1[C@@](C=2C=CC(C)=CC=2)(O)CC(Cl)O1 ODZHZJDDQBXYIF-CSODTCANSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 4
WVWZECQNFWFVFW-UHFFFAOYSA-N methyl 2-methylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C WVWZECQNFWFVFW-UHFFFAOYSA-N 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
IQFYYKKMVGJFEH-RNJXMRFFSA-N 1-[(2s,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-RNJXMRFFSA-N 0.000 description 3
YBXJEAPQVULNKE-UHFFFAOYSA-N 1-acetyl-5-methylpyrimidine-2,4-dione Chemical compound CC(=O)N1C=C(C)C(=O)NC1=O YBXJEAPQVULNKE-UHFFFAOYSA-N 0.000 description 3
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 3
QBAMFSIXQXKRMQ-HCUTXMHJSA-N C1(=CC=C(C=C1)[C@@]1(C[C@@H](O[C@@H]1C(O)C1=CC=C(C=C1)C)N1C(=O)NC(=O)C(=C1)F)O)C Chemical compound C1(=CC=C(C=C1)[C@@]1(C[C@@H](O[C@@H]1C(O)C1=CC=C(C=C1)C)N1C(=O)NC(=O)C(=C1)F)O)C QBAMFSIXQXKRMQ-HCUTXMHJSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
150000002730 mercury Chemical class 0.000 description 3
238000002156 mixing Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 2
DYDYCJUWEIAGSG-IZVXFFJCSA-N 2-[(2r,3s)-5-chloro-3-(4-chlorobenzoyl)-3-hydroxyoxolan-2-yl]-1-(4-chlorophenyl)-2-hydroxyethanone Chemical compound O=C([C@]1(O)CC(Cl)O[C@@H]1C(O)C(=O)C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 DYDYCJUWEIAGSG-IZVXFFJCSA-N 0.000 description 2
ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 description 2
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 2
JUZNVIUTDSYVKA-UHFFFAOYSA-N 3-acetyl-5-fluoro-1h-pyrimidine-2,4-dione Chemical compound CC(=O)N1C(=O)NC=C(F)C1=O JUZNVIUTDSYVKA-UHFFFAOYSA-N 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
229910000343 potassium bisulfate Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
229910001958 silver carbonate Inorganic materials 0.000 description 2
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BLFCXYJTVFTNRX-UHFFFAOYSA-N 2-chloro-4-(furan-2-yl)pyrimidine Chemical compound ClC1=NC=CC(C=2OC=CC=2)=N1 BLFCXYJTVFTNRX-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000012345 acetylating agent Substances 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
238000001838 alkalimetric titration Methods 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
238000010792 warming Methods 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/103—Mercury compounds without C-Mercury linkages
- 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
- C07H19/06—Pyrimidine radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

CH8212659A 1959-01-16 1959-12-21 Verfahren zur Herstellung von heterocyclischen Verbindungen CH385860A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US78711859A	1959-01-16	1959-01-16
US807769A US2949451A (en)	1959-04-21	1959-04-21	Preparation of thymidine and deoxyfluorouridine, and intermediates therefor

Publications (1)

Publication Number	Publication Date
CH385860A true CH385860A (de)	1964-12-31

Family

ID=27120614

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH8212659A CH385860A (de)	1959-01-16	1959-12-21	Verfahren zur Herstellung von heterocyclischen Verbindungen

Country Status (5)

Country	Link
BE (1)	BE586507A (fr)
CH (1)	CH385860A (fr)
DE (1)	DE1211648B (fr)
FR (2)	FR1283828A (fr)
SE (1)	SE310495B (fr)

1959
- 1959-12-21 CH CH8212659A patent/CH385860A/de unknown
- 1959-12-24 DE DEH38251A patent/DE1211648B/de active Pending
1960
- 1960-01-11 FR FR815291A patent/FR1283828A/fr not_active Expired
- 1960-01-13 BE BE586507A patent/BE586507A/fr unknown
- 1960-01-15 SE SE370/60A patent/SE310495B/xx unknown
- 1960-08-30 FR FR837096A patent/FR382M/fr not_active Expired

Also Published As

Publication number	Publication date
DE1211648B (de)	1966-03-03
FR1283828A (fr)	1962-02-09
FR382M (fr)	1961-04-04
SE310495B (fr)	1969-05-05
BE586507A (fr)	1960-07-13

Publication	Publication Date	Title
DE69010257T2 (de)	1995-02-23	Verfahren zur Herstellung N-substituierter Maleimide.
DE2147023C3 (de)	1982-04-29	Verfahren zur Herstellung von 1H- Tetrazol-Verbindungen
DE1134086B (de)	1962-08-02	Verfahren zur Herstellung von analeptisch wirksamen alpha-Aminoisobutyrophenonen und deren Säureadditionssalzen
DE2000030C3 (de)	1974-08-01	3-Alkoxy-und 3-Phenoxy-2-(diphenylhydroxy)methyl-propylamine und diese enthaltende Arzneimittel
EP0072919B1 (fr)	1986-01-08	Procédé de préparation de 1,2-diméthyl-5-nitroimidazole de grande pureté
CH385860A (de)	1964-12-31	Verfahren zur Herstellung von heterocyclischen Verbindungen
DE1205094B (de)	1965-11-18	Verfahren zur Herstellung von 17alpha-Aminosteroiden der Androstenreihe
DE881795C (de)	1953-07-02	Verfahren zur Herstellung von Cholinabkoemmlingen
DE69011996T2 (de)	1995-02-02	Verfahren zur Herstellung von 1,4-Dihydroxy-2-arylnaphthoat.
DE1695789C3 (de)	1978-07-13	Verfahren zur Herstellung von Benzodiazepinderivaten
DE1298981B (de)	1969-07-10	D-threo-1-Phenyl-2-amino-1, 3-propandiolderivate und Verfahren zu ihrer Herstellung
AT216671B (de)	1961-08-10	Verfahren zur Herstellung von Verbindungen verschiedener Penicilline mit Sulfonamiden
DE442655C (de)	1927-04-04	Verfahren zur Herstellung von Cyclohexenylalkylbarbitursaeuren
DE917424C (de)	1954-09-02	Verfahren zur Herstellung von N-Acetyl-propargyl-arylaminen und ihrer p-staendigen Substitutionsprodukte
AT205027B (de)	1959-08-25	Verfahren zur Herstellung von neuen α-Aroyl-α-phthaliminoessigsäureestern
DE904175C (de)	1954-02-15	Verfahren zur Herstellung von Pyrimidindionen
DE907299C (de)	1954-03-22	Verfahren zur Herstellung von Chloramphenicol
AT239252B (de)	1965-03-25	Verfahren zur partiellen oder vollständigen Carbamylierung von zweiwertigen Alkoholen oder von deren partiell O-substituierten Derivaten
AT258910B (de)	1967-12-27	Verfahren zur Herstellung von Benzo-dihydro-thiadiazin-Derivaten
DE946145C (de)	1956-07-26	Verfahren zur Herstellung von Alkyl- bzw. Alkoxalkylaminobenzoesaeureestern
AT365598B (de)	1982-01-25	Verfahren zur herstellung eines neuen formamidkomplexes von 7-beta-(d-2-phenylacetamido) -3-methylceph-3-emcarbonsaeure
DE1236524C2 (de)	1973-10-04	Verfahren zur herstellung von l-(-) -alpha-methyl-beta-(3,4-dihydroxy-phenyl)alanin
DE2402231B2 (de)	1977-07-28	Verfahren zur herstellung von 4- acetamidophenyl-2-acetoxybenzoat
DE611692C (de)	1935-04-02	Verfahren zur Darstellung von cyclisch disubstituierten Tetrazolen
DE1670261A1 (de)	1971-01-28	Verfahren zur Herstellung von N-Hexahydropyrimidyl-(4)-carbamin-saeureestern