DD248588A5 - Verfahren zur herstellung von hydroxy-und alkoxypyrimidinen - Google Patents

Verfahren zur herstellung von hydroxy-und alkoxypyrimidinen Download PDF

Info

Publication number: DD248588A5
Authority: DD; German Democratic Republic
Prior art keywords: phenyl; alkyl; substituted; hydrogen; compound
Prior art date: 1985-07-24

Application number

DD86292804A

Other languages

German (de)

English (en)

Inventor

Mattina John L La

Frederick J Walker

Original Assignee

��@��Kk��

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.)

1985-07-24

Filing date

1986-07-23

Publication date

1987-08-12

1986-07-23 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1987-08-12 Publication of DD248588A5 publication Critical patent/DD248588A5/de

Links

238000000034 method Methods 0.000 title claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 77
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
229910052739 hydrogen Inorganic materials 0.000 claims description 37
239000001257 hydrogen Substances 0.000 claims description 37
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
-1 chloro, methyl Chemical group 0.000 claims description 27
125000003884 phenylalkyl group Chemical group 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000005936 piperidyl group Chemical group 0.000 claims description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
229910052736 halogen Chemical group 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
ZJWMWURHRTYFIM-UHFFFAOYSA-N 5-methoxy-4,6-dimethyl-n-(2-phenylpentyl)pyrimidin-2-amine Chemical compound C=1C=CC=CC=1C(CCC)CNC1=NC(C)=C(OC)C(C)=N1 ZJWMWURHRTYFIM-UHFFFAOYSA-N 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
GMZJXGLCLPGSJC-UHFFFAOYSA-N 2-(dimethylamino)-4-(4-fluorophenyl)pyrimidin-5-ol Chemical compound CN(C)C1=NC=C(O)C(C=2C=CC(F)=CC=2)=N1 GMZJXGLCLPGSJC-UHFFFAOYSA-N 0.000 claims description 3
GJJFZDXPMYBREP-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)propylamino]-4,6-dimethylpyrimidin-5-ol Chemical compound CC1=C(O)C(C)=NC(NCCCC=2C=CC(Cl)=CC=2)=N1 GJJFZDXPMYBREP-UHFFFAOYSA-N 0.000 claims description 3
SGHSKLORTPFFAJ-UHFFFAOYSA-N 4,6-dimethyl-2-(2-phenylhexylamino)pyrimidin-5-ol Chemical compound C=1C=CC=CC=1C(CCCC)CNC1=NC(C)=C(O)C(C)=N1 SGHSKLORTPFFAJ-UHFFFAOYSA-N 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
SYIHKOKZMZWQST-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)propyl]-5-methoxy-4,6-dimethylpyrimidine Chemical compound N1=C(C)C(OC)=C(C)N=C1CCCC1=CC=C(Cl)C=C1 SYIHKOKZMZWQST-UHFFFAOYSA-N 0.000 claims description 2
LAXKEQOITIZFET-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-5-methoxy-n,n-dimethylpyrimidin-2-amine Chemical compound COC1=CN=C(N(C)C)N=C1C1=CC=C(Cl)C(Cl)=C1 LAXKEQOITIZFET-UHFFFAOYSA-N 0.000 claims description 2
IZSBNGJIYZQYSZ-UHFFFAOYSA-N 5-methoxy-4,6-dimethyl-n-(2-phenylhexyl)pyrimidin-2-amine Chemical compound C=1C=CC=CC=1C(CCCC)CNC1=NC(C)=C(OC)C(C)=N1 IZSBNGJIYZQYSZ-UHFFFAOYSA-N 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
101100241859 Mus musculus Oacyl gene Proteins 0.000 claims 2
DNGATYNRRIJQGC-UHFFFAOYSA-N 4,6-dimethyl-2-[3-(4-methylphenyl)propylamino]pyrimidin-5-ol Chemical compound C1=CC(C)=CC=C1CCCNC1=NC(C)=C(O)C(C)=N1 DNGATYNRRIJQGC-UHFFFAOYSA-N 0.000 claims 1
ZZNKPJHTODGFRQ-UHFFFAOYSA-N 5-methoxy-4-methyl-n-(2-phenylhexyl)pyrimidin-2-amine Chemical compound C=1C=CC=CC=1C(CCCC)CNC1=NC=C(OC)C(C)=N1 ZZNKPJHTODGFRQ-UHFFFAOYSA-N 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 14
208000008469 Peptic Ulcer Diseases 0.000 abstract description 4
150000002617 leukotrienes Chemical class 0.000 abstract description 4
230000002685 pulmonary effect Effects 0.000 abstract description 4
230000000172 allergic effect Effects 0.000 abstract description 3
230000015572 biosynthetic process Effects 0.000 abstract description 3
208000027866 inflammatory disease Diseases 0.000 abstract description 3
230000002757 inflammatory effect Effects 0.000 abstract description 3
239000003112 inhibitor Substances 0.000 abstract description 3
238000003786 synthesis reaction Methods 0.000 abstract description 3
208000026935 allergic disease Diseases 0.000 abstract description 2
208000024172 Cardiovascular disease Diseases 0.000 abstract 1
208000011191 Pulmonary vascular disease Diseases 0.000 abstract 1
230000001120 cytoprotective effect Effects 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000000203 mixture Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
208000006673 asthma Diseases 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000002904 solvent Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
150000003230 pyrimidines Chemical class 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
208000009079 Bronchial Spasm Diseases 0.000 description 3
208000014181 Bronchial disease Diseases 0.000 description 3
206010006482 Bronchospasm Diseases 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
239000004533 oil dispersion Substances 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
OMOQERIFKHRFNQ-UHFFFAOYSA-N 4,6-dimethyl-2-(nonylamino)pyrimidin-5-ol Chemical compound CCCCCCCCCNC1=NC(C)=C(O)C(C)=N1 OMOQERIFKHRFNQ-UHFFFAOYSA-N 0.000 description 2
YFVYTPCMOHQZBK-UHFFFAOYSA-N 5-methoxy-n,n,4-trimethylpyrimidin-2-amine Chemical compound COC1=CN=C(N(C)C)N=C1C YFVYTPCMOHQZBK-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
208000019693 Lung disease Diseases 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
208000037976 chronic inflammation Diseases 0.000 description 2
230000006020 chronic inflammation Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
150000002357 guanidines Chemical class 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
TXYIUYKEGPAMME-UHFFFAOYSA-N (2-amino-1,3-oxazol-5-yl)-(3,4-dichlorophenyl)methanone Chemical compound O1C(N)=NC=C1C(=O)C1=CC=C(Cl)C(Cl)=C1 TXYIUYKEGPAMME-UHFFFAOYSA-N 0.000 description 1
FHXLASBQBGORNJ-UHFFFAOYSA-N (2-amino-1,3-oxazol-5-yl)-phenylmethanone Chemical compound O1C(N)=NC=C1C(=O)C1=CC=CC=C1 FHXLASBQBGORNJ-UHFFFAOYSA-N 0.000 description 1
XEYAEHMAXJCJOM-UHFFFAOYSA-N (5-methyl-2,4-dioxohexan-3-yl) acetate Chemical compound CC(C)C(=O)C(C(C)=O)OC(C)=O XEYAEHMAXJCJOM-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
BLJBTGUNWYECJJ-UHFFFAOYSA-N 2-(2-hexylphenyl)-4-methylpyrimidin-5-ol Chemical compound CCCCCCC1=CC=CC=C1C1=NC=C(O)C(C)=N1 BLJBTGUNWYECJJ-UHFFFAOYSA-N 0.000 description 1
XHVDDSMBBBANIJ-UHFFFAOYSA-N 2-(dimethylamino)-4,6-diphenylpyrimidin-5-ol Chemical compound OC=1C(C=2C=CC=CC=2)=NC(N(C)C)=NC=1C1=CC=CC=C1 XHVDDSMBBBANIJ-UHFFFAOYSA-N 0.000 description 1
QYKQHXLGMUZOKL-UHFFFAOYSA-N 2-(dimethylamino)-4-methyl-6-phenylpyrimidin-5-ol Chemical compound CN(C)C1=NC(C)=C(O)C(C=2C=CC=CC=2)=N1 QYKQHXLGMUZOKL-UHFFFAOYSA-N 0.000 description 1
WJKDDDFPCRUBHN-UHFFFAOYSA-N 2-(dimethylamino)-4-methyl-6-propan-2-ylpyrimidin-5-ol Chemical compound CC(C)C1=NC(N(C)C)=NC(C)=C1O WJKDDDFPCRUBHN-UHFFFAOYSA-N 0.000 description 1
SKGYDORUFXXCEB-UHFFFAOYSA-N 2-(dimethylamino)-4-methylpyrimidin-5-ol Chemical compound CN(C)C1=NC=C(O)C(C)=N1 SKGYDORUFXXCEB-UHFFFAOYSA-N 0.000 description 1
BUYWWOLHPHKGNC-UHFFFAOYSA-N 2-(hexylamino)-4-phenylpyrimidin-5-ol Chemical compound CCCCCCNC1=NC=C(O)C(C=2C=CC=CC=2)=N1 BUYWWOLHPHKGNC-UHFFFAOYSA-N 0.000 description 1
NVNCUOOXEABRIU-UHFFFAOYSA-N 2-(nonylamino)-4-phenylpyrimidin-5-ol Chemical compound CCCCCCCCCNC1=NC=C(O)C(C=2C=CC=CC=2)=N1 NVNCUOOXEABRIU-UHFFFAOYSA-N 0.000 description 1
UBGRSKXBCVWAOV-UHFFFAOYSA-N 2-(propan-2-ylamino)pyrimidin-5-ol Chemical compound CC(C)NC1=NC=C(O)C=N1 UBGRSKXBCVWAOV-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
BATVWQIPSVQPEI-UHFFFAOYSA-N 2-amino-4,6-dimethylpyrimidin-5-ol Chemical compound CC1=NC(N)=NC(C)=C1O BATVWQIPSVQPEI-UHFFFAOYSA-N 0.000 description 1
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125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DD86292804A 1985-07-24 1986-07-23 Verfahren zur herstellung von hydroxy-und alkoxypyrimidinen DD248588A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/758,199 US4711888A (en)	1985-07-24	1985-07-24	Hydroxy and alkoxy pyrimidines

Publications (1)

Publication Number	Publication Date
DD248588A5 true DD248588A5 (de)	1987-08-12

Family

ID=25050889

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86292804A DD248588A5 (de)	1985-07-24	1986-07-23	Verfahren zur herstellung von hydroxy-und alkoxypyrimidinen

Country Status (25)

Country	Link
US (1)	US4711888A (da)
EP (1)	EP0210044B1 (da)
JP (1)	JPH0647579B2 (da)
KR (1)	KR890001549B1 (da)
CN (1)	CN1006792B (da)
AU (1)	AU569194B2 (da)
CA (1)	CA1265519A (da)
DD (1)	DD248588A5 (da)
DE (1)	DE3673718D1 (da)
DK (1)	DK162986C (da)
EG (1)	EG18181A (da)
ES (1)	ES2000734A6 (da)
FI (1)	FI89911C (da)
GR (1)	GR861917B (da)
HU (1)	HU196764B (da)
IE (1)	IE63404B1 (da)
IL (1)	IL79471A0 (da)
NO (1)	NO173442C (da)
NZ (1)	NZ216951A (da)
PH (1)	PH22484A (da)
PL (2)	PL150617B1 (da)
PT (1)	PT83036B (da)
SU (1)	SU1574171A3 (da)
YU (1)	YU45020B (da)
ZA (1)	ZA865489B (da)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE135699T1 (de) *	1986-01-13	1996-04-15	American Cyanamid Co	4,5,6-substituierte 2-pyrimidinamine
US4959365A (en) *	1986-10-31	1990-09-25	Pfizer Inc.	Topical compositions of lipophilic pharmaceuticals agents
HU199683B (en) *	1987-07-22	1990-03-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing pharmaceutical compositions analgesic, antiphlogistic, antipyretic, antianginic and/or antioxidative activity
MX14001A (es) *	1987-12-02	1993-06-01	Pfizer	Procedimiento para preparar derivados de hidroxipirimidinas
ATE96321T1 (de) *	1988-12-14	1993-11-15	Pfizer	Derivate von 5-hydroxy- und 5-methoxy-2-aminopyrimidin als inhibitoren der interleukin-1produktion.
US5071852A (en) *	1988-12-14	1991-12-10	Pfizer Inc.	Derivatives of 5-hydroxy and 5-methoxy 2-amino-pyrimidines as inhibitors of interleukin-1 production
US4940712A (en) *	1989-05-26	1990-07-10	Pfizer Inc.	Derivatives of hydroxyprimidines as leukotriene synthesis inhibitors
US5248682A (en) *	1991-01-31	1993-09-28	Warner-Lambert Company	2-substituted-4,6-di-tertiary-butyl-5-hydroxy-1,3-pyrimidines useful as antiinflammatory agents
CA2365269A1 (en) *	1991-01-31	1992-08-20	Warner-Lambert Company	Substituted 4,6-di-tertiary-butyl-5-hydroxy-pyrimidines
US5177079A (en) *	1991-01-31	1993-01-05	Warner-Lambert Company	2-substituted-4,6-di-tertiarybutyl-5-hydroxy-1,3-pyrimidines useful as antiinflammatory agents
USD333563S (en)	1991-06-26	1993-03-02	Alpha Enterprises, Inc.	Security holder for a compact disc
USD333562S (en)	1991-06-26	1993-03-02	Alpha Enterprises, Inc.	Security holder for a cassette tape
US5270319A (en) *	1991-09-09	1993-12-14	Warner-Lambert Company	5-hydroxy-2-pyrimidinylmethylene derivatives useful as antiinflammatory agents
US5196431A (en) *	1992-02-24	1993-03-23	Warner-Lambert Company	2-substituted amino-4, 6-di-tertiary-buthyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents
US5220025A (en) *	1992-02-24	1993-06-15	Warner-Lambert Company	2-substituted amino-4, 6-di-tertiary-butyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents
EP0902019A4 (en) *	1996-05-16	2002-03-27	Nissan Chemical Ind Ltd	METHOD FOR PRODUCING PYRIMIDINE COMPOUNDS
US5952331A (en) *	1996-05-23	1999-09-14	Syntex (Usa) Inc.	Aryl pyrimidine derivatives
TW440563B (en) *	1996-05-23	2001-06-16	Hoffmann La Roche	Aryl pyrimidine derivatives and a pharmaceutical composition thereof
US5958934A (en) *	1996-05-23	1999-09-28	Syntex (U.S.A.) Inc.	Aryl pyrimidine derivatives and uses thereof
US7045519B2 (en)	1998-06-19	2006-05-16	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
US6417185B1 (en)	1998-06-19	2002-07-09	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
WO2002000683A2 (en) *	2000-06-23	2002-01-03	Vanderbilt University	Novel chain-breaking antioxidants
DE102004054080A1 (de) *	2004-11-09	2006-05-11	Wella Ag	Haut- oder Haarbehandlungsmittel mit Schutzeffekt
US8367669B2 (en) *	2005-06-15	2013-02-05	Vanderbilt University	Inhibitors of hemeprotein-catalyzed lipid peroxidation
US9133212B1 (en)	2005-06-15	2015-09-15	Vanderbilt University	Inhibitors of hemeprotein-catalyzed lipid peroxidation
GT200600457A (es) *	2005-10-13	2007-04-27	Aventis Pharma Inc	Sal de fosfato dihidrogeno como antagonistas del receptor de prostaglandina d2
JP2008156048A (ja) *	2006-12-22	2008-07-10	Isamu Nakamura	車両用板材キャリア
US8877766B2 (en)	2013-02-15	2014-11-04	Peter F. Kador	Neuroprotective multifunctional antioxidants and their monofunctional analogs

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IN153791B (da)	1979-03-10	1984-08-18	Soc D Etudes Prod Chimique
US4659363A (en) *	1983-07-25	1987-04-21	Ciba-Geigy Corporation	N-(2-nitrophenyl)-2-aminopyrimidine derivatives, the preparation and use thereof
US4554276A (en) *	1983-10-03	1985-11-19	Pfizer Inc.	2-Amino-5-hydroxy-4-methylpyrimidine derivatives
EP0164204A1 (en) *	1984-05-12	1985-12-11	FISONS plc	Novel pharmaceutically useful pyrimidines

1985
- 1985-07-24 US US06/758,199 patent/US4711888A/en not_active Expired - Lifetime
1986
- 1986-07-16 EP EP86305466A patent/EP0210044B1/en not_active Expired - Lifetime
- 1986-07-16 DE DE8686305466T patent/DE3673718D1/de not_active Expired - Lifetime
- 1986-07-21 IL IL79471A patent/IL79471A0/xx not_active IP Right Cessation
- 1986-07-22 CA CA000514336A patent/CA1265519A/en not_active Expired - Lifetime
- 1986-07-22 EG EG453/86A patent/EG18181A/xx active
- 1986-07-22 GR GR861917A patent/GR861917B/el unknown
- 1986-07-22 PT PT83036A patent/PT83036B/pt not_active IP Right Cessation
- 1986-07-23 FI FI863029A patent/FI89911C/fi not_active IP Right Cessation
- 1986-07-23 DD DD86292804A patent/DD248588A5/de not_active IP Right Cessation
- 1986-07-23 PH PH34054A patent/PH22484A/en unknown
- 1986-07-23 SU SU864027808A patent/SU1574171A3/ru active
- 1986-07-23 KR KR1019860005974A patent/KR890001549B1/ko not_active Expired
- 1986-07-23 IE IE195286A patent/IE63404B1/en not_active IP Right Cessation
- 1986-07-23 AU AU60447/86A patent/AU569194B2/en not_active Ceased
- 1986-07-23 YU YU1321/86A patent/YU45020B/xx unknown
- 1986-07-23 ZA ZA865489A patent/ZA865489B/xx unknown
- 1986-07-23 NZ NZ216951A patent/NZ216951A/xx unknown
- 1986-07-23 DK DK349486A patent/DK162986C/da active
- 1986-07-23 CN CN86104539A patent/CN1006792B/zh not_active Expired
- 1986-07-23 ES ES8600529A patent/ES2000734A6/es not_active Expired
- 1986-07-23 NO NO862956A patent/NO173442C/no unknown
- 1986-07-23 HU HU863000A patent/HU196764B/hu not_active IP Right Cessation
- 1986-07-24 PL PL1986260784A patent/PL150617B1/pl unknown
- 1986-07-24 PL PL1986271856A patent/PL151571B1/pl unknown
- 1986-07-24 JP JP61174704A patent/JPH0647579B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FI89911C (fi)	1993-12-10
SU1574171A3 (ru)	1990-06-23
IL79471A0 (en)	1986-10-31
NO173442C (no)	1993-12-15
EP0210044B1 (en)	1990-08-29
PL271856A1 (en)	1988-09-29
US4711888A (en)	1987-12-08
CN86104539A (zh)	1987-01-21
AU6044786A (en)	1987-04-30
HU196764B (en)	1989-01-30
ES2000734A6 (es)	1988-03-16
EP0210044A3 (en)	1987-10-21
KR890001549B1 (ko)	1989-05-08
NO862956D0 (no)	1986-07-23
DE3673718D1 (de)	1990-10-04
AU569194B2 (en)	1988-01-21
YU132186A (en)	1988-04-30
PH22484A (en)	1988-09-12
FI863029A0 (fi)	1986-07-23
FI863029L (fi)	1987-01-25
KR870001173A (ko)	1987-03-11
PL260784A1 (en)	1988-08-18
NZ216951A (en)	1989-06-28
JPS6226276A (ja)	1987-02-04
IE861952L (en)	1987-01-24
CA1265519A (en)	1990-02-06
PT83036A (en)	1986-08-01
HUT41745A (en)	1987-05-28
ZA865489B (en)	1988-03-30
DK162986C (da)	1992-06-01
FI89911B (fi)	1993-08-31
EG18181A (en)	1992-09-30
DK349486A (da)	1987-01-25
PL151571B1 (en)	1990-09-28
EP0210044A2 (en)	1987-01-28
IE63404B1 (en)	1995-04-19
NO173442B (no)	1993-09-06
PT83036B (pt)	1989-01-30
DK162986B (da)	1992-01-06
YU45020B (en)	1991-06-30
GR861917B (en)	1986-11-24
DK349486D0 (da)	1986-07-23
PL150617B1 (en)	1990-06-30
JPH0647579B2 (ja)	1994-06-22
NO862956L (no)	1987-01-26
CN1006792B (zh)	1990-02-14

Legal Events

Date	Code	Title	Description
1994-04-14	NPV	Change in the person, the name or the address of the representative (addendum to changes before extension act)
1995-08-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
US4711888A (en)	1987-12-08	Hydroxy and alkoxy pyrimidines
DE2705446C2 (da)	1989-10-12
DE69708142T2 (de)	2002-07-11	1-phenylpyrozol-verbindungen und ihre medizinische anwendung
DE69428952T2 (de)	2002-06-27	Thienopyrimidinderivate, ihre Herstellung und Verwendung
DD201790A5 (de)	1983-08-10	Verfahren zur herstellung von 3-aryl-5-isothiazolen
DE3876813T4 (de)	1995-05-11	3(2H)Pyridazinon, Verfahren zu dessen Herstellung und dieses enthaltendes Mittel gegen SRS-A.
DE69321471T2 (de)	1999-03-04	Dioxcyclobutenderivate als angiotensin ii antagonisten
NO170883B (no)	1992-09-14	Fremgangsmaate for fremstilling av 2-amino-5-hydroksy-4-metylpyrimidin-derivater
DE3129309A1 (de)	1982-03-18	Hypoglykaemische 5-substituierte oxazolidin-2,4-dione
DE3530046C2 (de)	1997-12-04	Äthylendiaminmonoamid-Derivate
DE10133665A1 (de)	2003-01-30	Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung
DE1965264A1 (de)	1970-07-16	Pyrazinoylsulfamide und Verfahren zu ihrer Herstellung
EP0122580A1 (de)	1984-10-24	Pyrimidinderivate, deren Herstellung und pharmazeutische Präparate
EP0171739B1 (en)	1990-01-10	Imidazo[1,5-a]pyrimidine derivatives and process for their preparation
US4940712A (en)	1990-07-10	Derivatives of hydroxyprimidines as leukotriene synthesis inhibitors
EP0093252B1 (de)	1988-03-09	Thiomethylpyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE3782378T2 (de)	1993-03-11	Dihydropyridinderivate und deren pharmazeutische zusammensetzungen.
DE3879410T2 (de)	1993-06-24	Acyl-derivate von hydroxy-pyrimidinen.
DE2443682C2 (de)	1983-11-10	Neue 2,4-Diamino-5-benzylpyrimidine
DE2509037A1 (de)	1976-09-02	1-aryluracile, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
IE41563B1 (en)	1980-01-30	Sulfonamides
EP0124630A1 (de)	1984-11-14	Pyrimidin-Thioalkylpyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindung enthaltende Arzneimittel
DE2656227C2 (de)	1985-07-04	Basisch alkylierte Diphenyldisulfid-2,2'-biscarbonsäureamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE2354145A1 (de)	1974-05-16	Chinazolin-2(lh)-one und verfahren zu ihrer herstellung
DE3121137A1 (de)	1982-12-16	Neue pyridazino(4,5-b)indole, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen, zwischenprodukte und deren herstellung"