CH609056A5 - Process for the preparation of pyrimidines - Google Patents

Process for the preparation of pyrimidines

Info

Publication number: CH609056A5
Authority: CH; Switzerland
Prior art keywords: sodium; carboxamide; alkyl; oxalate; carbon atoms
Prior art date: 1975-04-24

Application number

CH439876A

Other languages

English (en)

French (fr)

Inventor

Susumu Nakanishi

Original Assignee

Pfizer

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.)

1975-04-24

Filing date

1976-04-07

Publication date

1979-02-15

1976-04-07 Application filed by Pfizer filed Critical Pfizer

1979-02-15 Publication of CH609056A5 publication Critical patent/CH609056A5/fr

Links

238000000034 method Methods 0.000 title claims abstract description 32
238000002360 preparation method Methods 0.000 title claims abstract description 10
150000003230 pyrimidines Chemical class 0.000 title claims description 3
-1 alkyl oxalate Chemical compound 0.000 claims abstract description 31
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
239000002904 solvent Substances 0.000 claims abstract description 20
GXZOXGRLLFZVGF-UHFFFAOYSA-N 2-aminoquinoline-3-carboxamide Chemical compound C1=CC=C2N=C(N)C(C(=O)N)=CC2=C1 GXZOXGRLLFZVGF-UHFFFAOYSA-N 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 16
239000011734 sodium Substances 0.000 claims abstract description 16
229910052708 sodium Inorganic materials 0.000 claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 13
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 abstract description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 5
239000012312 sodium hydride Substances 0.000 claims abstract description 5
229910000104 sodium hydride Inorganic materials 0.000 claims abstract description 5
UJTRRNALUYKHQE-UHFFFAOYSA-N sodium;diphenylmethylbenzene Chemical compound [Na+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 UJTRRNALUYKHQE-UHFFFAOYSA-N 0.000 claims abstract description 4
IHYFFUYNTMJRRD-UHFFFAOYSA-N sodium 3-aminopropylazanide Chemical compound [Na+].NCCC[NH-] IHYFFUYNTMJRRD-UHFFFAOYSA-N 0.000 claims abstract description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 26
235000019441 ethanol Nutrition 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 23
239000000047 product Substances 0.000 claims description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
239000003153 chemical reaction reagent Substances 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 8
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical group CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 8
238000007363 ring formation reaction Methods 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
125000005907 alkyl ester group Chemical group 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
239000006227 byproduct Substances 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 claims description 4
125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
HQCJPLVCEVRXIE-UHFFFAOYSA-N 2-amino-6-fluoroquinoline-3-carboxamide Chemical compound FC1=CC=C2N=C(N)C(C(=O)N)=CC2=C1 HQCJPLVCEVRXIE-UHFFFAOYSA-N 0.000 claims description 2
JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 claims description 2
HETSDWRDICBRSQ-UHFFFAOYSA-N 3h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CC=NC2=C1 HETSDWRDICBRSQ-UHFFFAOYSA-N 0.000 claims description 2
UHYQLALXNODRFC-UHFFFAOYSA-N 4-oxo-1h-pyrimido[4,5-b]quinoline-2-carboxylic acid Chemical class C1=CC=C2C=C(C(=O)NC(C(=O)O)=N3)C3=NC2=C1 UHYQLALXNODRFC-UHFFFAOYSA-N 0.000 claims description 2
KKORZNPFZXORNH-UHFFFAOYSA-N 4-oxo-3h-quinoline-2-carboxylic acid Chemical compound C1=CC=C2C(=O)CC(C(=O)O)=NC2=C1 KKORZNPFZXORNH-UHFFFAOYSA-N 0.000 claims description 2
CXHAZTHTEOMQGE-UHFFFAOYSA-N CCC(=O)O.O=C1NC=NC2=CC=CC=C12 Chemical compound CCC(=O)O.O=C1NC=NC2=CC=CC=C12 CXHAZTHTEOMQGE-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
BMCAWNQKVVTNFP-UHFFFAOYSA-N ethyl 4-oxo-1h-quinazoline-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=NC(=O)C2=C1 BMCAWNQKVVTNFP-UHFFFAOYSA-N 0.000 claims description 2
125000005909 ethyl alcohol group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
238000010667 large scale reaction Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
150000003109 potassium Chemical class 0.000 claims description 2
230000035484 reaction time Effects 0.000 claims description 2
150000004703 alkoxides Chemical class 0.000 abstract description 3
239000000043 antiallergic agent Substances 0.000 abstract description 2
150000003857 carboxamides Chemical class 0.000 abstract 2
150000003112 potassium compounds Chemical class 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
239000004480 active ingredient Substances 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
150000003901 oxalic acid esters Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
AAZKQXRGMFBMCF-UHFFFAOYSA-N 2-amino-6,7-dimethoxyquinoline-3-carboxamide Chemical compound NC(=O)C1=C(N)N=C2C=C(OC)C(OC)=CC2=C1 AAZKQXRGMFBMCF-UHFFFAOYSA-N 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
230000007885 bronchoconstriction Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000006199 nebulizer Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000003826 tablet Substances 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000000150 Sympathomimetic Substances 0.000 description 1
241000502253 Talpa occidentalis Species 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
FZWIBIHTJMCHGT-UHFFFAOYSA-N potassium;diphenylmethylbenzene Chemical compound [K+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 FZWIBIHTJMCHGT-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH439876A 1975-04-24 1976-04-07 Process for the preparation of pyrimidines CH609056A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US57131875A	1975-04-24	1975-04-24

Publications (1)

Publication Number	Publication Date
CH609056A5 true CH609056A5 (en)	1979-02-15

Family

ID=24283193

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH439876A CH609056A5 (en)	1975-04-24	1976-04-07	Process for the preparation of pyrimidines

Country Status (20)

Country	Link
JP (1)	JPS51127098A (de)
AR (1)	AR207814A1 (de)
AT (1)	AT351549B (de)
BG (1)	BG27356A3 (de)
CA (1)	CA1065863A (de)
CH (1)	CH609056A5 (de)
DD (1)	DD125208A5 (de)
DK (1)	DK142323B (de)
ES (1)	ES446498A1 (de)
FI (1)	FI761020A7 (de)
HU (1)	HU172062B (de)
LU (1)	LU74787A1 (de)
MX (1)	MX3019E (de)
NL (1)	NL161155C (de)
PL (1)	PL101824B1 (de)
PT (1)	PT65023B (de)
RO (1)	RO68966A (de)
SE (1)	SE7603133L (de)
SU (1)	SU638261A3 (de)
YU (1)	YU79176A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5361243A (en) *	1976-11-12	1978-06-01	Fujitsu Ltd	1-chip arithmetic circuit device
JP2006503094A (ja) *	2002-10-16	2006-01-26	スミスクラインビーチャムコーポレーション	化合物

1976
- 1976-01-01 AR AR262884A patent/AR207814A1/es active
- 1976-03-09 SE SE7603133A patent/SE7603133L/xx unknown
- 1976-03-10 CA CA247,583A patent/CA1065863A/en not_active Expired
- 1976-03-25 MX MX000113U patent/MX3019E/es unknown
- 1976-03-26 YU YU00791/76A patent/YU79176A/xx unknown
- 1976-03-30 NL NL7603293.A patent/NL161155C/xx active
- 1976-03-30 ES ES446498A patent/ES446498A1/es not_active Expired
- 1976-03-30 DK DK143876AA patent/DK142323B/da not_active IP Right Cessation
- 1976-04-07 SU SU762343061A patent/SU638261A3/ru active
- 1976-04-07 CH CH439876A patent/CH609056A5/fr not_active IP Right Cessation
- 1976-04-13 AT AT270076A patent/AT351549B/de not_active IP Right Cessation
- 1976-04-13 BG BG032890A patent/BG27356A3/xx unknown
- 1976-04-13 JP JP51041749A patent/JPS51127098A/ja active Granted
- 1976-04-14 FI FI761020A patent/FI761020A7/fi not_active Application Discontinuation
- 1976-04-15 DD DD192403A patent/DD125208A5/xx unknown
- 1976-04-16 LU LU74787A patent/LU74787A1/xx unknown
- 1976-04-16 HU HU76PI00000521A patent/HU172062B/hu unknown
- 1976-04-17 PL PL1976188875A patent/PL101824B1/pl unknown
- 1976-04-17 RO RO7685654A patent/RO68966A/ro unknown
- 1976-04-19 PT PT65023A patent/PT65023B/pt unknown

Also Published As

Publication number	Publication date
AT351549B (de)	1979-07-25
LU74787A1 (de)	1977-02-07
DK143876A (de)	1976-10-25
DK142323C (de)	1981-06-29
MX3019E (es)	1980-02-13
ES446498A1 (es)	1977-06-16
YU79176A (en)	1982-05-31
HU172062B (hu)	1978-05-28
DK142323B (da)	1980-10-13
JPS543880B2 (de)	1979-02-27
ATA270076A (de)	1979-01-15
PL101824B1 (pl)	1979-02-28
CA1065863A (en)	1979-11-06
BG27356A3 (bg)	1979-10-12
JPS51127098A (en)	1976-11-05
NL161155B (nl)	1979-08-15
PT65023B (en)	1977-09-09
SU638261A3 (ru)	1978-12-15
FI761020A7 (de)	1976-10-25
PT65023A (en)	1976-05-01
AR207814A1 (es)	1976-10-29
SE7603133L (sv)	1976-10-25
DD125208A5 (de)	1977-04-06
RO68966A (ro)	1981-05-30
NL7603293A (nl)	1976-10-26
NL161155C (nl)	1980-01-15

Legal Events

Date	Code	Title	Description
1981-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
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