DD150609A5 - Verfahren zur herstellung von pyrimidin-verbindungen - Google Patents

Verfahren zur herstellung von pyrimidin-verbindungen Download PDF

Info

Publication number: DD150609A5
Authority: DD; German Democratic Republic
Prior art keywords: amino; pyrimidinyl; methyl; group; formula
Prior art date: 1979-05-18

Application number

DD80221082A

Other languages

German (de)

English (en)

Inventor

Adrian Marxer

Kurt Eichenberger

Original Assignee

Ciba Geigy Ag

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.)

1979-05-18

Filing date

1980-05-13

Publication date

1981-09-09

1980-05-13 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1981-09-09 Publication of DD150609A5 publication Critical patent/DD150609A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 94
150000003839 salts Chemical class 0.000 claims abstract description 59
239000002253 acid Substances 0.000 claims abstract description 36
239000001257 hydrogen Substances 0.000 claims abstract description 35
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
125000002947 alkylene group Chemical group 0.000 claims abstract description 12
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims abstract description 4
-1 pyrimidinylamino Chemical group 0.000 claims description 90
239000000203 mixture Substances 0.000 claims description 51
239000007858 starting material Substances 0.000 claims description 49
238000006243 chemical reaction Methods 0.000 claims description 38
238000000034 method Methods 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical class 0.000 claims description 26
239000002585 base Substances 0.000 claims description 23
125000003282 alkyl amino group Chemical group 0.000 claims description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 17
150000002431 hydrogen Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
238000002360 preparation method Methods 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 8
125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000005281 alkyl ureido group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
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 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000000464 thioxo group Chemical group S=* 0.000 claims description 2
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims 1
239000002220 antihypertensive agent Substances 0.000 abstract description 4
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 2
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 153
239000000243 solution Substances 0.000 description 98
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 88
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 86
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
235000002639 sodium chloride Nutrition 0.000 description 45
239000000155 melt Substances 0.000 description 43
238000010992 reflux Methods 0.000 description 40
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 35
235000019441 ethanol Nutrition 0.000 description 33
235000011121 sodium hydroxide Nutrition 0.000 description 29
UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 28
239000013078 crystal Substances 0.000 description 25
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 20
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 20
238000001816 cooling Methods 0.000 description 20
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 20
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
238000009835 boiling Methods 0.000 description 17
239000002904 solvent Substances 0.000 description 17
239000002244 precipitate Substances 0.000 description 16
239000000725 suspension Substances 0.000 description 16
238000001953 recrystallisation Methods 0.000 description 14
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 13
238000002844 melting Methods 0.000 description 13
238000003756 stirring Methods 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
239000003054 catalyst Substances 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000000047 product Substances 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
239000000825 pharmaceutical preparation Substances 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
239000012312 sodium hydride Substances 0.000 description 10
229910000104 sodium hydride Inorganic materials 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
229920002472 Starch Polymers 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
231100000252 nontoxic Toxicity 0.000 description 8
230000003000 nontoxic effect Effects 0.000 description 8
150000003585 thioureas Chemical class 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
238000000354 decomposition reaction Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
239000012452 mother liquor Substances 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
UPVBKNZVOJNQKE-UHFFFAOYSA-N 2,6-dichloropyrimidin-4-amine Chemical compound NC1=CC(Cl)=NC(Cl)=N1 UPVBKNZVOJNQKE-UHFFFAOYSA-N 0.000 description 6
SSAYHQQUDKQNAC-UHFFFAOYSA-N 6-chloro-2-methylpyrimidin-4-amine Chemical class CC1=NC(N)=CC(Cl)=N1 SSAYHQQUDKQNAC-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000007127 saponification reaction Methods 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 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 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000001476 alcoholic effect Effects 0.000 description 5
230000003276 anti-hypertensive effect Effects 0.000 description 5
230000015572 biosynthetic process Effects 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
239000002775 capsule Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
150000002540 isothiocyanates Chemical class 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
229940098779 methanesulfonic acid Drugs 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
FMGVXEWCBHQXCV-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-2,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC(C)=CC(NC=2NCCN=2)=N1 FMGVXEWCBHQXCV-UHFFFAOYSA-N 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
150000003230 pyrimidines Chemical class 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
235000015424 sodium Nutrition 0.000 description 5
229940100445 wheat starch Drugs 0.000 description 5
JMXOCODMGODHCO-UHFFFAOYSA-N 6-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2-methoxypyrimidin-4-amine Chemical compound COC1=NC(Cl)=CC(NC=2NCCN=2)=N1 JMXOCODMGODHCO-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
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 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000005237 alkyleneamino group Chemical group 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000002026 chloroform extract Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000008298 dragée Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
208000001953 Hypotension Diseases 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
229940030600 antihypertensive agent Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000002178 crystalline material Substances 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229940014259 gelatin Drugs 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229930195733 hydrocarbon Natural products 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
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
KRZGKJJPEOUIBI-UHFFFAOYSA-N hydron;thiourea;iodide Chemical compound I.NC(S)=N KRZGKJJPEOUIBI-UHFFFAOYSA-N 0.000 description 3
208000021822 hypotensive Diseases 0.000 description 3
230000001077 hypotensive effect Effects 0.000 description 3
239000005457 ice water Substances 0.000 description 3
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
150000002462 imidazolines Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
JLUDQRNTIZZFRB-UHFFFAOYSA-N methyl N'-(2-phenylpyrimidin-4-yl)carbamimidothioate hydroiodide Chemical compound I.C1(=CC=CC=C1)C1=NC=CC(=N1)NC(SC)=N JLUDQRNTIZZFRB-UHFFFAOYSA-N 0.000 description 3
BOOSYURYMKSSSK-UHFFFAOYSA-N methyl n'-(2,6-dimethylpyrimidin-4-yl)carbamimidothioate Chemical compound CSC(N)=NC1=CC(C)=NC(C)=N1 BOOSYURYMKSSSK-UHFFFAOYSA-N 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
OZANUADAOVTFPU-UHFFFAOYSA-N (2,6-dimethylpyrimidin-4-yl)thiourea Chemical compound CC1=CC(NC(N)=S)=NC(C)=N1 OZANUADAOVTFPU-UHFFFAOYSA-N 0.000 description 2
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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
BJJDXAFKCKSLTE-UHFFFAOYSA-N 2,6-dimethylpyrimidin-4-amine Chemical compound CC1=CC(N)=NC(C)=N1 BJJDXAFKCKSLTE-UHFFFAOYSA-N 0.000 description 2
QLQQHEHEBSZVAM-UHFFFAOYSA-N 2-(diethylamino)-4-hydroxy-1h-pyrimidin-6-one Chemical compound CCN(CC)C1=NC(O)=CC(O)=N1 QLQQHEHEBSZVAM-UHFFFAOYSA-N 0.000 description 2
PVXBPIYYFYNVDL-UHFFFAOYSA-N 2-(diethylamino)-4-hydroxy-5-nitro-1h-pyrimidin-6-one Chemical compound CCN(CC)C1=NC(O)=C([N+]([O-])=O)C(=O)N1 PVXBPIYYFYNVDL-UHFFFAOYSA-N 0.000 description 2
KALSOJKUICKBCX-UHFFFAOYSA-N 2-n-propylpyrimidine-2,4-diamine Chemical compound CCCNC1=NC=CC(N)=N1 KALSOJKUICKBCX-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
LHQVQNGCOQOUAP-UHFFFAOYSA-N 4,6-dichloro-n,n-diethyl-5-nitropyrimidin-2-amine Chemical compound CCN(CC)C1=NC(Cl)=C([N+]([O-])=O)C(Cl)=N1 LHQVQNGCOQOUAP-UHFFFAOYSA-N 0.000 description 2
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238000001640 fractional crystallisation Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
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150000004820 halides Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
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UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002542 isoureas Chemical class 0.000 description 1
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238000012792 lyophilization process Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
LRPCLTPZMUIPFK-UHFFFAOYSA-N methane;sulfuric acid Chemical compound C.OS(O)(=O)=O LRPCLTPZMUIPFK-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
MZWLVMNYNIROLU-UHFFFAOYSA-N methyl N'-(2,6-diethyl-5-methylpyrimidin-4-yl)carbamimidothioate hydroiodide Chemical compound I.C(C)C1=NC(=C(C(=N1)NC(SC)=N)C)CC MZWLVMNYNIROLU-UHFFFAOYSA-N 0.000 description 1
AYYAGJRAXYOAEN-UHFFFAOYSA-N methyl N'-(2,6-dimethoxypyrimidin-4-yl)carbamimidothioate Chemical compound COC1=NC(=CC(=N1)NC(SC)=N)OC AYYAGJRAXYOAEN-UHFFFAOYSA-N 0.000 description 1
JODOUFXFLHQUEK-UHFFFAOYSA-N methyl N'-(2-methyl-6-phenoxypyrimidin-4-yl)carbamimidothioate hydroiodide Chemical compound I.CC1=NC(=CC(=N1)NC(SC)=N)OC1=CC=CC=C1 JODOUFXFLHQUEK-UHFFFAOYSA-N 0.000 description 1
HKYJXVGXOIUYEB-UHFFFAOYSA-N methyl N'-(6-anilino-2-methylpyrimidin-4-yl)carbamimidothioate hydroiodide Chemical compound I.CC1=NC(=CC(=N1)NC(SC)=N)NC1=CC=CC=C1 HKYJXVGXOIUYEB-UHFFFAOYSA-N 0.000 description 1
WRTYLIHAUWONES-UHFFFAOYSA-N methyl N'-(6-chloro-2-methoxypyrimidin-4-yl)carbamimidothioate hydroiodide Chemical compound I.ClC1=CC(=NC(=N1)OC)NC(SC)=N WRTYLIHAUWONES-UHFFFAOYSA-N 0.000 description 1
VZXSFLSERFXLIH-UHFFFAOYSA-N methyl N'-[6-(4-methoxyanilino)-2-methylpyrimidin-4-yl]carbamimidothioate hydroiodide Chemical compound I.COC1=CC=C(C=C1)NC1=CC(=NC(=N1)C)NC(SC)=N VZXSFLSERFXLIH-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
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DPYCNOPHTAWAIB-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-2,6-diethyl-5-methylpyrimidin-4-amine Chemical compound CCC1=NC(CC)=C(C)C(NC=2NCCN=2)=N1 DPYCNOPHTAWAIB-UHFFFAOYSA-N 0.000 description 1
GEETXANFZHHWDJ-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-2-methoxypyrimidin-4-amine;hydrochloride Chemical compound Cl.COC1=NC=CC(NC=2NCCN=2)=N1 GEETXANFZHHWDJ-UHFFFAOYSA-N 0.000 description 1
BBZWPNQFVNVVNG-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-2-methyl-6-phenoxypyrimidin-4-amine Chemical compound C=1C(OC=2C=CC=CC=2)=NC(C)=NC=1NC1=NCCN1 BBZWPNQFVNVVNG-UHFFFAOYSA-N 0.000 description 1
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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
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YKWZVBQULWMJDQ-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-2-propan-2-yloxypyrimidin-4-amine Chemical compound CC(C)OC1=NC=CC(NC=2NCCN=2)=N1 YKWZVBQULWMJDQ-UHFFFAOYSA-N 0.000 description 1
ISRQBBZMPMNGTH-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-2-propan-2-yloxypyrimidin-4-amine Chemical compound CC(C)OC1=NC(OC)=CC(NC=2NCCN=2)=N1 ISRQBBZMPMNGTH-UHFFFAOYSA-N 0.000 description 1
LTOXNXSYSGUFQT-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)pyrimidin-4-amine Chemical compound N1CCN=C1NC1=CC=NC=N1 LTOXNXSYSGUFQT-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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125000006124 n-propyl sulfonyl group Chemical group 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
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 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
239000003791 organic solvent mixture 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
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-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
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
230000009090 positive inotropic effect Effects 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
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239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 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
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
206010038464 renal hypertension Diseases 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
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238000006798 ring closing metathesis reaction Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 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
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
229940064707 sympathomimetics Drugs 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
125000005505 thiomorpholino group Chemical group 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
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
229910052720 vanadium Inorganic materials 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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
- C07D239/52—Two oxygen 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD80221082A 1979-05-18 1980-05-13 Verfahren zur herstellung von pyrimidin-verbindungen DD150609A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH466979		1979-05-18

Publications (1)

Publication Number	Publication Date
DD150609A5 true DD150609A5 (de)	1981-09-09

Family

ID=4280399

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80221082A DD150609A5 (de)	1979-05-18	1980-05-13	Verfahren zur herstellung von pyrimidin-verbindungen

Country Status (21)

Country	Link
EP (1)	EP0019811A1 (fr)
JP (1)	JPS55154971A (fr)
KR (1)	KR830002757A (fr)
AR (1)	AR228256A1 (fr)
AU (1)	AU5848480A (fr)
DD (1)	DD150609A5 (fr)
DK (1)	DK214480A (fr)
ES (1)	ES491514A0 (fr)
FI (1)	FI801600A7 (fr)
GB (1)	GB2052487B (fr)
GR (1)	GR68453B (fr)
IE (1)	IE49803B1 (fr)
IL (1)	IL60086A (fr)
MA (1)	MA18829A1 (fr)
NO (1)	NO801469L (fr)
NZ (1)	NZ193730A (fr)
OA (1)	OA06533A (fr)
PL (1)	PL224313A1 (fr)
PT (1)	PT71251A (fr)
ZA (1)	ZA802909B (fr)
ZW (1)	ZW11880A1 (fr)

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EP2134709A1 (fr)	2007-03-09	2009-12-23	Vertex Pharmaceuticals, Inc.	Utilisation des aminopyridines comme inhibiteurs de protéines kinases
EP2137183B1 (fr)	2007-03-09	2011-09-28	Vertex Pharmaceuticals Incorporated	Aminopyrimidines utiles en tant qu'inhibiteurs des protéines kinases
JP2010523700A (ja)	2007-04-13	2010-07-15	バーテックスファーマシューティカルズインコーポレイテッド	キナーゼインヒビターとして有用なアミノピリミジン
CN101801959A (zh)	2007-05-02	2010-08-11	沃泰克斯药物股份有限公司	可用作激酶抑制剂的氨基嘧啶类化合物
CN101679378A (zh)	2007-05-02	2010-03-24	沃泰克斯药物股份有限公司	用作激酶抑制剂的噻唑和吡唑
AR067762A1 (es)	2007-07-31	2009-10-21	Vertex Pharma	Proceso para preparar 5-fluoro-1h-pirazolo (3,4-b) piridin-3-amina y derivados de la misma
AU2009288200A1 (en)	2008-09-03	2010-03-11	Vertex Pharmaceuticals Incorporated	Co-crystals and pharmaceutical formulations comprising the same
WO2010077613A1 (fr) *	2008-12-09	2010-07-08	Gilead Sciences, Inc.	Modulateurs de récepteurs de type toll (tlr)
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1980
- 1980-05-05 MA MA19025A patent/MA18829A1/fr unknown
- 1980-05-13 DD DD80221082A patent/DD150609A5/de unknown
- 1980-05-14 ES ES491514A patent/ES491514A0/es active Granted
- 1980-05-15 NZ NZ193730A patent/NZ193730A/xx unknown
- 1980-05-15 IL IL60086A patent/IL60086A/xx unknown
- 1980-05-16 GR GR61963A patent/GR68453B/el unknown
- 1980-05-16 ZA ZA00802909A patent/ZA802909B/xx unknown
- 1980-05-16 FI FI801600A patent/FI801600A7/fi not_active Application Discontinuation
- 1980-05-16 GB GB8016309A patent/GB2052487B/en not_active Expired
- 1980-05-16 ZW ZW118/80A patent/ZW11880A1/xx unknown
- 1980-05-16 AU AU58484/80A patent/AU5848480A/en not_active Abandoned
- 1980-05-16 EP EP80102724A patent/EP0019811A1/fr not_active Withdrawn
- 1980-05-16 DK DK214480A patent/DK214480A/da not_active Application Discontinuation
- 1980-05-16 IE IE1023/80A patent/IE49803B1/en unknown
- 1980-05-16 NO NO801469A patent/NO801469L/no unknown
- 1980-05-16 PT PT71251A patent/PT71251A/pt unknown
- 1980-05-17 JP JP6586380A patent/JPS55154971A/ja active Pending
- 1980-05-17 OA OA57113A patent/OA06533A/fr unknown
- 1980-05-17 KR KR1019800001944A patent/KR830002757A/ko active Pending
- 1980-05-17 PL PL22431380A patent/PL224313A1/xx unknown
- 1980-05-19 AR AR281109A patent/AR228256A1/es active

Also Published As

Publication number	Publication date
PL224313A1 (fr)	1981-02-13
JPS55154971A (en)	1980-12-02
IL60086A0 (en)	1980-07-31
MA18829A1 (fr)	1980-12-31
DK214480A (da)	1980-11-19
ES8104279A1 (es)	1981-04-16
PT71251A (en)	1980-06-01
EP0019811A1 (fr)	1980-12-10
GB2052487A (en)	1981-01-28
AR228256A1 (es)	1983-02-15
IL60086A (en)	1984-03-30
ZA802909B (en)	1981-05-27
AU5848480A (en)	1980-11-20
OA06533A (fr)	1981-07-31
FI801600A7 (fi)	1981-01-01
ES491514A0 (es)	1981-04-16
ZW11880A1 (en)	1980-12-17
NO801469L (no)	1980-11-19
KR830002757A (ko)	1983-05-30
IE801023L (en)	1980-11-18
GB2052487B (en)	1983-05-11
IE49803B1 (en)	1985-12-25
NZ193730A (en)	1982-12-21
GR68453B (fr)	1981-12-30

Publication	Publication Date	Title
DD150609A5 (de)	1981-09-09	Verfahren zur herstellung von pyrimidin-verbindungen
DE69530989T2 (de)	2004-05-19	Neue pyrimidinderivate und verfahren zu ihrer herstellung
DE69636671T2 (de)	2007-08-30	Pyrido[2,3-]-pyrimidine und deren Verwendung beim Inhibieren von Zellproliferation und Protein-Tyrosin-Kinase-Enzymaktivität
DE2341925A1 (de)	1975-03-06	Neue pyrimidinderivate und verfahren zu ihrer herstellung
CH642965A5 (de)	1984-05-15	Substituierte 5-(2-imidazolin-2-yl)-aminopyrimidine und verfahren zu deren herstellung.
DE2255172A1 (de)	1973-05-24	Imidazotriazinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE2309160A1 (de)	1973-09-27	2-imidazolin-2-yl-amino-substituierte, benzokondensierte, heterocyclische verbindungen und arzneipraeparate
DD216934A5 (de)	1985-01-02	Verfahren zur herstellung neuer derivate von xanthinen
DE2720085C2 (fr)	1988-11-17
DE2849537A1 (de)	1980-05-22	Substituierte 5-(2-imidazolin-2-yl)- aminopyrimidine und verfahren zu deren herstellung
DE60004671T2 (de)	2004-07-29	Neue piperazinylalkylthiopyrimidine derivate, diese enthaltende pharmazeutische zusammenstellungen und verfahren zu deren herstellung
DE2062024A1 (de)	1972-05-25	Tetrahydro-imidazo- und Tetrahydropyrimido- eckige Klammer auf 2,1-b eckige Klammer zu -chinazoline, ihre Salze mit Säuren, Verfahren zu ihrer Herstellung und Arzneipräparate
EP0122580A1 (fr)	1984-10-24	Derivés de la pyrimidine, leur préparation et compositions pharmaceutiques
EP0047328B1 (fr)	1984-05-09	Dérivés de 1H- et 2H-indazole et médicament les contenant
EP0288431B1 (fr)	1992-08-19	3H-1,2,3-triazolo[4,5-d]pyrimidines
DE2133998A1 (de)	1973-01-25	2,3-dihydro-oxo-imidazo eckige klammer auf 1,2-a eckige klammer zu -pyrimidine, deren saeureadditionssalze und verfahren zu deren herstellung
DE2918778A1 (de)	1980-11-20	6-substituierte 11-alkylen-morphantridine
EP0093252B1 (fr)	1988-03-09	Dérivés de thiométhylpyridine, procédé pour leur préparation et médicaments les contenant
EP0124893A2 (fr)	1984-11-14	Dérivés de pyrimidone
EP0124630B1 (fr)	1987-01-28	Dérivés de pyrimidinothioalkyle pyridine, procédé pour leur préparation et médicaments contenant ces composés
DE3807084A1 (de)	1989-09-14	Neue benzimidazo(1,2-c)chinazoline, ihre herstellung und verwendung
DE2139083A1 (de)	1973-02-15	Substituierte pyrimidine, verfahren zu deren herstellung und sie enthaltende arzneimittel
CH591457A5 (fr)	1977-09-15
EP0056027A1 (fr)	1981-10-29	2-(1-piperazinyl)-4-pyrinidinamines
DE833651C (de)	1952-03-10	Verfahren zur Herstellung von neuen Pyrimidinabkoemmlingen