CH471797A - Verfahren zur Herstellung neuer Pyrimidine - Google Patents

Verfahren zur Herstellung neuer Pyrimidine

Info

Publication number: CH471797A
Authority: CH; Switzerland
Prior art keywords: radicals; pyrimidyl; amino; group; compounds
Prior art date: 1964-05-25

Application number

CH555167A

Other languages

German (de)

English (en)

Inventor

Albrecht Dr Hueni

Ernst Dr Schweizer

Dorothy Dr Schroeder

Original Assignee

Ciba Geigy

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.)

1964-05-25

Filing date

1964-05-25

Publication date

1969-04-30

1964-05-25 Application filed by Ciba Geigy filed Critical Ciba Geigy

1964-05-25 Priority to CH555167A priority Critical patent/CH471797A/de

1964-05-25 Priority claimed from CH679164A external-priority patent/CH462824A/de

1965-08-19 Priority to FR28817A priority patent/FR4588M/fr

1969-04-30 Publication of CH471797A publication Critical patent/CH471797A/de

Links

238000000034 method Methods 0.000 title claims description 17
150000003230 pyrimidines Chemical class 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title description 3
-1 sulfonyloxy group Chemical group 0.000 claims description 78
125000003277 amino group Chemical group 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 17
239000004305 biphenyl Substances 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
150000003254 radicals Chemical class 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
235000010290 biphenyl Nutrition 0.000 description 4
125000006267 biphenyl group Chemical group 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 3
241000223836 Babesia Species 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
201000008680 babesiosis Diseases 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052717 sulfur Chemical group 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
244000248349 Citrus limon Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
235000011430 Malus pumila Nutrition 0.000 description 1
235000015103 Malus silvestris Nutrition 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000003430 antimalarial agent Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
MPCQNSCUKOECNW-UHFFFAOYSA-N butan-1-ol;ethanol Chemical compound CCO.CCCCO MPCQNSCUKOECNW-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
201000004792 malaria Diseases 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
229930182817 methionine Natural products 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000004894 pentylamino group Chemical group C(CCCC)N* 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000005987 sulfurization reaction Methods 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
235000014101 wine Nutrition 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- 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
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- 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
- C07D239/48—Two nitrogen atoms
- 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
- C07D239/56—One oxygen atom and one sulfur atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH555167A 1964-05-25 1964-05-25 Verfahren zur Herstellung neuer Pyrimidine CH471797A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH555167A CH471797A (de)	1964-05-25	1964-05-25	Verfahren zur Herstellung neuer Pyrimidine
FR28817A FR4588M (fr)	1964-05-25	1965-08-19

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH555167A CH471797A (de)	1964-05-25	1964-05-25	Verfahren zur Herstellung neuer Pyrimidine
CH679164A CH462824A (de)	1964-05-25	1964-05-25	Verfahren zur Herstellung neuer Pyrimidine
CH520765		1965-04-13

Publications (1)

Publication Number	Publication Date
CH471797A true CH471797A (de)	1969-04-30

Family

ID=27175131

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH555167A CH471797A (de)	1964-05-25	1964-05-25	Verfahren zur Herstellung neuer Pyrimidine

Country Status (2)

Country	Link
CH (1)	CH471797A (fr)
FR (1)	FR4588M (fr)

1964
- 1964-05-25 CH CH555167A patent/CH471797A/de not_active IP Right Cessation
1965
- 1965-08-19 FR FR28817A patent/FR4588M/fr not_active Expired

Also Published As

Publication number	Publication date
FR4588M (fr)	1966-11-14

Legal Events

Date	Code	Title	Description
1971-12-31	PL	Patent ceased

Publication	Publication Date	Title
DE3688950T2 (de)	1994-03-17	Substituierte Chinolinderivate.
DE2408906A1 (de)	1974-09-19	6-styrylpyrazolo(3,4-d)pyrimidin-4-one und -pyrimidine mit ihren salzen
DE2233458A1 (de)	1973-02-08	Neue chinolinderivate
DE2029796A1 (de)	1971-01-07	12H- Dibenzo eckige Klammer auf d,g, eckige Klammer zu eckige Klammer auf 1,3 eckige Klammer zu dioxocin 6 carbonsauren, deren Ester und Salze
CH509345A (de)	1971-06-30	Verfahren zur Herstellung von neuen Chinolinderivaten
CH376115A (de)	1964-03-31	Verfahren zur Herstellung neuer substituierter Pyrimidine
DE2713586A1 (de)	1977-10-20	Neue organische verbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE2703522C2 (fr)	1988-07-07
DE1670939A1 (de)	1971-02-25	Verfahren zur Herstellung von 2-Isothiuroniummethyl-3-carbon-saeureamido-chinoxalin-di-N-oxid-(1,4)-halogeniden
DE1804328A1 (de)	1969-05-22	3-substituierte Chinoxalinone und Verfahren zur Herstellung von 3-substituierten Chinoxalin-2-Onen
CH396881A (de)	1965-08-15	Verfahren zur Herstellung neuer Hydrazone
DE1545677A1 (de)	1969-08-07	Neue Pyrimidine
CH462824A (de)	1968-09-30	Verfahren zur Herstellung neuer Pyrimidine
DE2360329A1 (de)	1974-06-20	1,7-dialkyl-1,2-dihydro-4-hydroxy-1,8naphthyridin-3-carbonsaeurealkylester
DE864555C (de)	1953-01-26	Verfahren zur Herstellung von 2, 4-Diamino-5-aryloxypyrimidinen
DE1000387C2 (de)	1957-06-27	Verfahren zur Herstellung von neuen, in 9-Stellung substituierten 1, 10-Diazaanthracenen
AT240373B (de)	1965-05-25	Verfahren zur Herstellung von Benzodiazepin-Derivaten
CH505850A (de)	1971-04-15	Verfahren zur Herstellung von neuen Benzoxazepinonen
AT222117B (de)	1962-07-10	Verfahren zur Herstellung neuer Azabenz-imidazole
DE2065321A1 (de)	1973-05-24	Indol-derivate
DE845342C (de)	1952-07-31	Verfahren zur Herstellung von organischen Arsenverbindungen
DE1770402C3 (de)	1976-07-15	N-Methyl-N-naphthyl-(1)-dithiocaTbamtnsäwre-2-benzoxazoVytester, Arzneimittel und Verfahren zu seiner Herstellung
DE1190468B (de)	1965-04-08	Verfahren zur Herstellung von 2, 4, 7-Triaminopteridinen
DE2101275A1 (de)	1972-07-27	Neue Chinazolinen-Verbindungen und Verfahren zu ihrer Herstellung
DE2530681A1 (de)	1976-02-05	Neue aminoderivate von pyrido (3,4-b)pyrazincarbonsaeuren und -carbonsaeureestern