CA1248104A - Derives de 4-oxo-6-(methylthio)pyrimidine et methode de preparation - Google Patents

Derives de 4-oxo-6-(methylthio)pyrimidine et methode de preparation

Info

Publication number: CA1248104A
Authority: CA; Canada
Prior art keywords: oxo; compound; dihydro; methylthio; pyrimidinecarbonitrile
Prior art date: 1983-06-30
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

Application number

CA000505828A

Other languages

English (en)

Inventor

Jehan F. Bagli

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth LLC

Original Assignee

American Home Products Corp

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.)

1983-06-30

Filing date

1986-04-03

Publication date

1989-01-03

1983-06-30 Priority claimed from US06/509,886 external-priority patent/US4505910A/en

1983-06-30 Priority claimed from US06/509,887 external-priority patent/US4507304A/en

1984-06-27 Priority claimed from CA000457551A external-priority patent/CA1232905A/fr

1986-04-03 Application filed by American Home Products Corp filed Critical American Home Products Corp

1986-04-03 Priority to CA000505828A priority Critical patent/CA1248104A/fr

1989-01-03 Application granted granted Critical

1989-01-03 Publication of CA1248104A publication Critical patent/CA1248104A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title abstract description 13
238000002360 preparation method Methods 0.000 title abstract description 8
BTIAVKOUWHGNFD-UHFFFAOYSA-N 4-methylsulfanyl-1h-pyrimidin-6-one Chemical class CSC1=CC(O)=NC=N1 BTIAVKOUWHGNFD-UHFFFAOYSA-N 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims description 97
-1 cyano, nitro, methylsulfonyl Chemical group 0.000 claims description 63
125000000217 alkyl group Chemical group 0.000 claims description 39
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 17
239000003960 organic solvent Substances 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
SJDBEROAEMAOJW-UHFFFAOYSA-N methyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate Chemical compound COC(=O)C(C#N)=C(SC)SC SJDBEROAEMAOJW-UHFFFAOYSA-N 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
150000001409 amidines Chemical class 0.000 claims description 4
SSWJKGVCZRWCAF-UHFFFAOYSA-N 2-methyl-4-methylsulfanyl-6-oxo-1h-pyrimidine-5-carbonitrile Chemical compound CSC=1N=C(C)NC(=O)C=1C#N SSWJKGVCZRWCAF-UHFFFAOYSA-N 0.000 claims description 3
NDAJNMAAXXIADY-UHFFFAOYSA-N 2-methylpropanimidamide Chemical compound CC(C)C(N)=N NDAJNMAAXXIADY-UHFFFAOYSA-N 0.000 claims description 3
FNHMJTUQUPQWJN-UHFFFAOYSA-N 2,2-dimethylpropanimidamide Chemical compound CC(C)(C)C(N)=N FNHMJTUQUPQWJN-UHFFFAOYSA-N 0.000 claims description 2
DQHSGKMAIHAQHR-UHFFFAOYSA-N 2-benzyl-4-methylsulfanyl-6-oxo-1h-pyrimidine-5-carbonitrile Chemical compound O=C1C(C#N)=C(SC)NC(CC=2C=CC=CC=2)=N1 DQHSGKMAIHAQHR-UHFFFAOYSA-N 0.000 claims 2
GKVFFFUKORHLSE-UHFFFAOYSA-N 2-cyclopropyl-4-methylsulfanyl-6-oxo-1h-pyrimidine-5-carbonitrile Chemical compound O=C1C(C#N)=C(SC)NC(C2CC2)=N1 GKVFFFUKORHLSE-UHFFFAOYSA-N 0.000 claims 2
LCEBODHLVPEMPK-UHFFFAOYSA-N 2-tert-butyl-4-methylsulfanyl-6-oxo-1h-pyrimidine-5-carbonitrile Chemical compound CSC=1NC(C(C)(C)C)=NC(=O)C=1C#N LCEBODHLVPEMPK-UHFFFAOYSA-N 0.000 claims 2
GRFDALDZVGOEAU-UHFFFAOYSA-N 4-methylsulfanyl-6-oxo-2-propan-2-yl-1h-pyrimidine-5-carbonitrile Chemical compound CSC=1NC(C(C)C)=NC(=O)C=1C#N GRFDALDZVGOEAU-UHFFFAOYSA-N 0.000 claims 2
QYMWQIFMQQJWDU-UHFFFAOYSA-N 2-ethyl-4-methylsulfanyl-6-oxo-1h-pyrimidine-5-carbonitrile Chemical compound CCC1=NC(=O)C(C#N)=C(SC)N1 QYMWQIFMQQJWDU-UHFFFAOYSA-N 0.000 claims 1
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 claims 1
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims 1
FXFPOKGPAPEJNE-UHFFFAOYSA-N cyclopropanecarboximidamide Chemical compound NC(=N)C1CC1 FXFPOKGPAPEJNE-UHFFFAOYSA-N 0.000 claims 1
GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 claims 1
230000000747 cardiac effect Effects 0.000 abstract description 7
241000124008 Mammalia Species 0.000 abstract description 6
150000005005 aminopyrimidines Chemical class 0.000 abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 70
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
229910052739 hydrogen Inorganic materials 0.000 description 40
229910052757 nitrogen Inorganic materials 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
239000000243 solution Substances 0.000 description 22
150000003839 salts Chemical class 0.000 description 20
239000000203 mixture Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
239000007787 solid Substances 0.000 description 13
239000002480 mineral oil Substances 0.000 description 12
235000010446 mineral oil Nutrition 0.000 description 12
125000004043 oxo group Chemical group O=* 0.000 description 12
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
125000004093 cyano group Chemical group *C#N 0.000 description 10
239000000725 suspension Substances 0.000 description 10
239000002253 acid Substances 0.000 description 9
XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000012360 testing method Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 6
230000003177 cardiotonic effect Effects 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229960001412 pentobarbital Drugs 0.000 description 6
125000000464 thioxo group Chemical group S=* 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
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 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000002585 base Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 5
210000003205 muscle Anatomy 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
206010019280 Heart failures Diseases 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
239000000496 cardiotonic agent Substances 0.000 description 4
125000001841 imino group Chemical group [H]N=* 0.000 description 4
238000001802 infusion Methods 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
210000003540 papillary muscle Anatomy 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
229940124531 pharmaceutical excipient Drugs 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
206010007559 Cardiac failure congestive Diseases 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
244000309464 bull Species 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
230000036461 convulsion Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 2
150000003230 pyrimidines Chemical class 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
230000002861 ventricular Effects 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 1
BXJDUQVJADYYCG-UHFFFAOYSA-N 2,3-dichlorobenzohydrazide Chemical compound NNC(=O)C1=CC=CC(Cl)=C1Cl BXJDUQVJADYYCG-UHFFFAOYSA-N 0.000 description 1
WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
YILXPRRSFSGYEO-UHFFFAOYSA-N 2-cyano-3-(ethylamino)-3-methylsulfanylprop-2-enoic acid Chemical compound CCNC(SC)=C(C#N)C(O)=O YILXPRRSFSGYEO-UHFFFAOYSA-N 0.000 description 1
QUZRNIYCOQVLME-UHFFFAOYSA-N 2-cyano-3-methylsulfanyl-3-(prop-2-enylamino)prop-2-enoic acid Chemical compound N#CC(C(O)=O)=C(SC)NCC=C QUZRNIYCOQVLME-UHFFFAOYSA-N 0.000 description 1
RYRGREPULIGMIR-UHFFFAOYSA-N 2-cyano-3-methylsulfanyl-3-(pyridin-3-ylamino)prop-2-enoic acid Chemical compound N#CC(C(O)=O)=C(SC)NC1=CC=CN=C1 RYRGREPULIGMIR-UHFFFAOYSA-N 0.000 description 1
SPIACPCLVJYRCN-UHFFFAOYSA-N 2-cyclopropyl-4-oxo-6-(pyridin-3-ylmethylamino)-1h-pyrimidine-5-carbonitrile Chemical compound N#CC=1C(=O)N=C(C2CC2)NC=1NCC1=CC=CN=C1 SPIACPCLVJYRCN-UHFFFAOYSA-N 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000505828A 1983-06-30 1986-04-03 Derives de 4-oxo-6-(methylthio)pyrimidine et methode de preparation Expired CA1248104A (fr)

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Application Number	Priority Date	Filing Date	Title
CA000505828A CA1248104A (fr)	1983-06-30	1986-04-03	Derives de 4-oxo-6-(methylthio)pyrimidine et methode de preparation

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US06/509,886 US4505910A (en)	1983-06-30	1983-06-30	Amino-pyrimidine derivatives, compositions and use
US06/509,887 US4507304A (en)	1983-06-30	1983-06-30	Use of 6-amino-5-pyrimidinecarbonitrile derivatives as cardiotonic agents
US509,886		1983-06-30
US509,887		1983-06-30
CA000457551A CA1232905A (fr)	1983-06-30	1984-06-27	Derives d'amino-pyrimidine
CA000505828A CA1248104A (fr)	1983-06-30	1986-04-03	Derives de 4-oxo-6-(methylthio)pyrimidine et methode de preparation

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000457551A Division CA1232905A (fr)	1983-06-30	1984-06-27	Derives d'amino-pyrimidine

Publications (1)

Publication Number	Publication Date
CA1248104A true CA1248104A (fr)	1989-01-03

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Application Number	Title	Priority Date	Filing Date
CA000505828A Expired CA1248104A (fr)	1983-06-30	1986-04-03	Derives de 4-oxo-6-(methylthio)pyrimidine et methode de preparation

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CA (1)	CA1248104A (fr)

1986
- 1986-04-03 CA CA000505828A patent/CA1248104A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-01-03	MKEX	Expiry

Publication	Publication Date	Title
US4505910A (en)	1985-03-19	Amino-pyrimidine derivatives, compositions and use
CA1232905A (fr)	1988-02-16	Derives d'amino-pyrimidine
KR890002290B1 (ko)	1989-06-28	피페라진 유도체 및 그의 제조방법
CA1256107A (fr)	1989-06-20	Derives de pyrimidine, leur preparation et leur emploi
NL8201999A (nl)	1982-12-16	Gesubstitueerde 1,2-diaminocyclobuteen-3,4-dionen, werkwijze voor het bereiden daarvan; geneesmiddelen; werkwijze voor het behandelen van door bemiddeling van histamine h2-receptoren tot stand gekomen toestanden.
AU2004213616A1 (en)	2004-09-02	A process of preparing imatinib
JPH01163177A (ja)	1989-06-27	オキサゾリジノン化合物
DE3750685T2 (de)	1995-03-02	Dopamin-beta-hydroxylasehemmer.
NZ243959A (en)	1995-07-26	Substituted pyrazine derivatives and pharmaceutical compositions thereof
EP0277794A2 (fr)	1988-08-10	N-hétérocycliques-N-(4-pipéridyle) amides
NO146335B (no)	1982-06-01	Boelgegenerator av stempeltype
US4617393A (en)	1986-10-14	5-substituted-6-aminopyrimidines, composition and uses as cardiotonic agents for increasing cardiac contractility
JPH05262761A (ja)	1993-10-12	アリールアルキルアミン誘導体
NO338104B1 (no)	2016-08-01	Tetrahydroisoquinolin-sulfonamid-derivater, farmasøytiske preparater inneholdende slike og anvendelse derav som terapeutisk middel
US5166162A (en)	1992-11-24	Pyridylsulfonylurea and pyridylsulfonylthiourea compounds
JP3135170B2 (ja)	2001-02-13	アミノメチル置換２，３−ジヒドロピラノ〔２，３−ｂ〕ピリジン類
CA1248104A (fr)	1989-01-03	Derives de 4-oxo-6-(methylthio)pyrimidine et methode de preparation
EP0145019B1 (fr)	1990-11-07	Dérivés de pyridazinone et leurs sels
US4795750A (en)	1989-01-03	Quinazoline compounds
AU644605B2 (en)	1993-12-16	Pyridone nitriles useful in treating cardiovascular disease
CA1141382A (fr)	1983-02-15	Derives de 2-(1-piperazinyl)-cycloheptimidazole
US3378564A (en)	1968-04-16	Certain pyridyl tetrazole derivatives
US4355031A (en)	1982-10-19	2,3-Dihydro-3-[4-(substituted)-1-piperazinyl]-1H-isoindol-1-ones
NO153850B (no)	1986-02-24	Analogifremgangsmaate for fremstilling av terapeutisk aktive guanidiner.
US4507304A (en)	1985-03-26	Use of 6-amino-5-pyrimidinecarbonitrile derivatives as cardiotonic agents