CA1136131A - Composes de pyrimidine, procede de preparation composes pharmaceutiques les contenant et applications therapeutiques - Google Patents

Composes de pyrimidine, procede de preparation composes pharmaceutiques les contenant et applications therapeutiques

Info

Publication number: CA1136131A
Authority: CA; Canada
Prior art keywords: amino; formula; pyrimidinyl; group; halogen
Prior art date: 1980-04-30
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

CA000350950A

Other languages

English (en)

Inventor

Adrian Marxer

Kurt Eichenberger

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.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1980-04-30

Filing date

1980-04-30

Publication date

1982-11-23

1980-04-30 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1980-04-30 Priority to CA000350950A priority Critical patent/CA1136131A/fr

1982-11-23 Application granted granted Critical

1982-11-23 Publication of CA1136131A publication Critical patent/CA1136131A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 101
238000000034 method Methods 0.000 title claims abstract description 44
230000008569 process Effects 0.000 title claims abstract description 36
238000002360 preparation method Methods 0.000 title claims abstract description 14
239000000825 pharmaceutical preparation Substances 0.000 title description 11
150000003230 pyrimidines Chemical class 0.000 title description 3
239000003814 drug Substances 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 74
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
239000001257 hydrogen Substances 0.000 claims abstract description 41
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
125000000217 alkyl group Chemical group 0.000 claims abstract description 34
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
125000002947 alkylene group Chemical group 0.000 claims abstract description 15
229910052799 carbon Inorganic materials 0.000 claims abstract description 15
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
238000004519 manufacturing process Methods 0.000 claims abstract 4
239000000203 mixture Substances 0.000 claims description 95
-1 hydroxy, amino Chemical group 0.000 claims description 87
239000002253 acid Substances 0.000 claims description 50
229910052736 halogen Inorganic materials 0.000 claims description 44
150000002367 halogens Chemical class 0.000 claims description 44
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
239000007858 starting material Substances 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 38
125000003282 alkyl amino group Chemical group 0.000 claims description 31
239000002585 base Substances 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 24
239000000126 substance Substances 0.000 claims description 22
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
150000002431 hydrogen Chemical group 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000005281 alkyl ureido group Chemical group 0.000 claims description 7
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
UENMYKVEYCEKKS-UHFFFAOYSA-N 6-chloro-4-n-(4,5-dihydro-1h-imidazol-2-yl)-2-n,2-n-dimethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=NC(Cl)=CC(NC=2NCCN=2)=N1 UENMYKVEYCEKKS-UHFFFAOYSA-N 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 5
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 5
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
ISBFXDCCRNUMCB-UHFFFAOYSA-N 6-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2-methylpyrimidin-4-amine Chemical compound ClC1=CC(=NC(=N1)C)NC=1NCCN1 ISBFXDCCRNUMCB-UHFFFAOYSA-N 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 4
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
125000000464 thioxo group Chemical group S=* 0.000 claims description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
WRNGRPFRGWSDCJ-UHFFFAOYSA-N 6-chloro-4-n-(4,5-dihydro-1h-imidazol-2-yl)-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(Cl)=CC(NC=2NCCN=2)=N1 WRNGRPFRGWSDCJ-UHFFFAOYSA-N 0.000 claims 3
WTNLQNPMDLYVTJ-UHFFFAOYSA-N I.ClC1=CC(=NC(=N1)C)NC(SC)=N Chemical compound I.ClC1=CC(=NC(=N1)C)NC(SC)=N WTNLQNPMDLYVTJ-UHFFFAOYSA-N 0.000 claims 1
238000006482 condensation reaction Methods 0.000 claims 1
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims 1
230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
208000001953 Hypotension Diseases 0.000 abstract description 2
208000021822 hypotensive Diseases 0.000 abstract description 2
230000001077 hypotensive effect Effects 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 147
239000000243 solution Substances 0.000 description 97
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 93
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 89
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 86
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
238000002844 melting Methods 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
230000008018 melting Effects 0.000 description 52
235000013350 formula milk Nutrition 0.000 description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
235000002639 sodium chloride Nutrition 0.000 description 47
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 40
239000000155 melt Substances 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
238000007792 addition Methods 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 31
235000019441 ethanol Nutrition 0.000 description 31
238000001704 evaporation Methods 0.000 description 31
230000008020 evaporation Effects 0.000 description 31
235000011167 hydrochloric acid Nutrition 0.000 description 26
229960000443 hydrochloric acid Drugs 0.000 description 26
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 25
238000000354 decomposition reaction Methods 0.000 description 23
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 23
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 22
229960004592 isopropanol Drugs 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
238000010992 reflux Methods 0.000 description 20
239000002904 solvent Substances 0.000 description 20
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 18
230000000875 corresponding effect Effects 0.000 description 17
239000013078 crystal Substances 0.000 description 17
238000001816 cooling Methods 0.000 description 16
229940012017 ethylenediamine Drugs 0.000 description 16
239000000725 suspension Substances 0.000 description 16
238000009835 boiling Methods 0.000 description 15
229960001701 chloroform Drugs 0.000 description 15
150000003254 radicals Chemical class 0.000 description 15
238000001953 recrystallisation Methods 0.000 description 15
238000003756 stirring Methods 0.000 description 15
239000000047 product Substances 0.000 description 14
239000013543 active substance Substances 0.000 description 13
239000003054 catalyst Substances 0.000 description 13
BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
229920002472 Starch Polymers 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
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 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
239000012043 crude product Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000012452 mother liquor Substances 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
231100000252 nontoxic Toxicity 0.000 description 7
230000003000 nontoxic effect Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
150000003585 thioureas Chemical class 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
230000001476 alcoholic effect Effects 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000000454 talc Substances 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
235000012222 talc Nutrition 0.000 description 5
UPVBKNZVOJNQKE-UHFFFAOYSA-N 2,6-dichloropyrimidin-4-amine Chemical compound NC1=CC(Cl)=NC(Cl)=N1 UPVBKNZVOJNQKE-UHFFFAOYSA-N 0.000 description 4
SSAYHQQUDKQNAC-UHFFFAOYSA-N 6-chloro-2-methylpyrimidin-4-amine Chemical compound CC1=NC(N)=CC(Cl)=N1 SSAYHQQUDKQNAC-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000002026 chloroform extract Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
229940014259 gelatin Drugs 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
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241001237728 Precis Species 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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239000002220 antihypertensive agent Substances 0.000 description 3
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239000007864 aqueous solution Substances 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000000576 coating method Methods 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
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125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
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230000003301 hydrolyzing effect Effects 0.000 description 3
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150000002540 isothiocyanates Chemical class 0.000 description 3
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235000019341 magnesium sulphate Nutrition 0.000 description 3
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239000003381 stabilizer Substances 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
239000000829 suppository Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
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RBZQUMOTLQTMQN-UHFFFAOYSA-N (2-methylpyrimidin-5-yl)thiourea Chemical compound CC1=NC=C(NC(N)=S)C=N1 RBZQUMOTLQTMQN-UHFFFAOYSA-N 0.000 description 2
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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WNVWHYCHNRILHL-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-2-phenylpyrimidin-4-amine Chemical compound N1CCN=C1NC1=CC=NC(C=2C=CC=CC=2)=N1 WNVWHYCHNRILHL-UHFFFAOYSA-N 0.000 description 1
WLMSWXRQVRGHRL-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-2-phenylpyrimidin-5-amine Chemical compound N1CCN=C1NC1=CN=C(C=2C=CC=CC=2)N=C1 WLMSWXRQVRGHRL-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
235000014786 phosphorus Nutrition 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
NDCHEDNAHCRVDA-UHFFFAOYSA-N propane-1,2-diamine;propane-1,3-diamine Chemical compound CC(N)CN.NCCCN NDCHEDNAHCRVDA-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000001603 reducing effect Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000350950A 1980-04-30 1980-04-30 Composes de pyrimidine, procede de preparation composes pharmaceutiques les contenant et applications therapeutiques Expired CA1136131A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000350950A CA1136131A (fr)	1980-04-30	1980-04-30	Composes de pyrimidine, procede de preparation composes pharmaceutiques les contenant et applications therapeutiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000350950A CA1136131A (fr)	1980-04-30	1980-04-30	Composes de pyrimidine, procede de preparation composes pharmaceutiques les contenant et applications therapeutiques

Publications (1)

Publication Number	Publication Date
CA1136131A true CA1136131A (fr)	1982-11-23

Family

ID=4116825

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000350950A Expired CA1136131A (fr)	1980-04-30	1980-04-30	Composes de pyrimidine, procede de preparation composes pharmaceutiques les contenant et applications therapeutiques

Country Status (1)

Country	Link
CA (1)	CA1136131A (fr)

1980
- 1980-04-30 CA CA000350950A patent/CA1136131A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-11-23	MKEX	Expiry

Publication	Publication Date	Title
IE49803B1 (en)	1985-12-25	4-or 5-pyrimidinyl-amino-1,3-diaza-2-cycloalkenes,processes for their preparation,pharmaceutical preparations containing these compounds,and their use in therapeutics
EP0422178B1 (fr)	1994-10-05	Derives pyrimidines
EP0055583B1 (fr)	1985-08-28	Antihypertensifs
EP0163599B1 (fr)	1990-03-21	Dérivés de pyrimidopyrimidine, procédé pour leur préparation, compositions pharmaceutiques les contenant et leur utilisation comme agents antiallergiques
US3635979A (en)	1972-01-18	Certain 6- and/or 7-alkoxy-substituted-2 4-bis(disubstituted amino) quinazolines
EP0123402B1 (fr)	1988-09-07	Dérivés de pyrimidine, leur préparation et leur utilisation
CZ17094A3 (en)	1994-05-18	BENZIMIDAZOLE DERIVATIVES AS 5-HT1a AND 5-HT2 ANTAGONISTS
EP0168262A2 (fr)	1986-01-15	Dérivés de pyrimidine, procédés pour leur préparation et leur utilisation
DE2341925A1 (de)	1975-03-06	Neue pyrimidinderivate und verfahren zu ihrer herstellung
CA1175432A (fr)	1984-10-02	Procede d'obtention de derives de n-oxacyclyl- alkylpiperidine; produits pharmaceutiques qui en contiennent et leur emploi
CS254319B2 (en)	1988-01-15	Method of imidazole derivatives production
AU2002367190B2 (en)	2006-10-05	Pyrimidotriazines as phosphatase inhibitors
US4351832A (en)	1982-09-28	2-(Piperazinyl)-4-pyrimidinamines
US4272535A (en)	1981-06-09	2,4-[1H,3H,5H]-(1)-Benzopyrano-[2,3-d]-pyrimidinediones and their use as anti-allergy agents
SE433746B (sv)	1984-06-12	Pyrazino(2,3-b)(1,5)bensodiazepiner, deras framstellning och anvendning
EP0144730B1 (fr)	1987-07-08	Dérivés de l'acide anilino-2 dihydro-1,6 oxo-6 pyrimidinecarboxylique-5, procédés pour leur préparation et agents anti-allergiques les contenant
DK156722B (da)	1989-09-25	Analogifremgangsmaade til fremstilling af 2-piperazinopyrimidinderivater
CA1136131A (fr)	1982-11-23	Composes de pyrimidine, procede de preparation composes pharmaceutiques les contenant et applications therapeutiques
US3498984A (en)	1970-03-03	4-amino-2-phenyl-6-thiopyrimidines
US4705787A (en)	1987-11-10	Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
CA1173831A (fr)	1984-09-04	Methode d'obtention de nouveaux composes polyazaheterocycliques
WO1981003022A1 (fr)	1981-10-29	2-(1-piperazinyl)-4-pyrinidinamines
EP0008277B1 (fr)	1981-09-02	Dérivés de benzopyrane, procédé pour leur préparation et compositions pharmaceutiques les contenant
CA1152074A (fr)	1983-08-16	Pyrimidyl-thiourees
US4434167A (en)	1984-02-28	Pyrimidyl thioureas useful for the treatment of hypertension and hyperlipidemia