BG64649B1 - Нови дихидропиримидини - Google Patents
Нови дихидропиримидини Download PDFInfo
- Publication number
- BG64649B1 BG64649B1 BG104812A BG10481200A BG64649B1 BG 64649 B1 BG64649 B1 BG 64649B1 BG 104812 A BG104812 A BG 104812A BG 10481200 A BG10481200 A BG 10481200A BG 64649 B1 BG64649 B1 BG 64649B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkyl
- substituted
- phenyl
- optionally substituted
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 42
- 239000000460 chlorine Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- -1 trifluoromethoxy, carboxyl Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000004076 pyridyl group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 150000003254 radicals Chemical class 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000001409 amidines Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 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 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 208000016350 chronic hepatitis B virus infection Diseases 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 206010059193 Acute hepatitis B Diseases 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 208000037628 acute hepatitis B virus infection Diseases 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000002672 hepatitis B Diseases 0.000 abstract description 6
- 230000002265 prevention Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- 108020004414 DNA Proteins 0.000 description 7
- WDLIDNANRSUVFL-UHFFFAOYSA-N 3,5-difluoropyridine-2-carboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=NC=C(F)C=C1F WDLIDNANRSUVFL-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000009396 hybridization Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ATUOLSDAAPMVJJ-UHFFFAOYSA-N 3,5-dichloropyridine-2-carbonitrile Chemical compound ClC1=CN=C(C#N)C(Cl)=C1 ATUOLSDAAPMVJJ-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- SOGUCWFOKBJAQO-UHFFFAOYSA-N methyl 2-[(2-chloro-4-fluorophenyl)methylidene]-3-oxobutanoate Chemical compound COC(=O)C(C(C)=O)=CC1=CC=C(F)C=C1Cl SOGUCWFOKBJAQO-UHFFFAOYSA-N 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- SHIBSTMRCDJXLN-UHFFFAOYSA-N Digoxigenin Natural products C1CC(C2C(C3(C)CCC(O)CC3CC2)CC2O)(O)C2(C)C1C1=CC(=O)OC1 SHIBSTMRCDJXLN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 230000037396 body weight Effects 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
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- 231100000433 cytotoxic Toxicity 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 description 3
- SHIBSTMRCDJXLN-KCZCNTNESA-N digoxigenin Chemical compound C1([C@@H]2[C@@]3([C@@](CC2)(O)[C@H]2[C@@H]([C@@]4(C)CC[C@H](O)C[C@H]4CC2)C[C@H]3O)C)=CC(=O)OC1 SHIBSTMRCDJXLN-KCZCNTNESA-N 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical class C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 2
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 2
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 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
- 241000700721 Hepatitis B virus Species 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 239000004480 active ingredient Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
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- 231100000135 cytotoxicity Toxicity 0.000 description 2
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- 150000002148 esters Chemical class 0.000 description 2
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
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- 239000011698 potassium fluoride Substances 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 239000011780 sodium chloride Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 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
- 230000009385 viral infection Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KXCYATPBXVAALV-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane;hydrate Chemical compound O.COCCOCCOC KXCYATPBXVAALV-UHFFFAOYSA-N 0.000 description 1
- CNLIIAKAAMFCJG-UHFFFAOYSA-N 2,3,5-trichloropyridine Chemical compound ClC1=CN=C(Cl)C(Cl)=C1 CNLIIAKAAMFCJG-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- KMQWNQKESAHDKD-UHFFFAOYSA-N 2-chloro-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(Cl)=C1 KMQWNQKESAHDKD-UHFFFAOYSA-N 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
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
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- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19817264A DE19817264A1 (de) | 1998-04-18 | 1998-04-18 | Neue Dihydropyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG104812A BG104812A (en) | 2001-06-29 |
| BG64649B1 true BG64649B1 (bg) | 2005-10-31 |
Family
ID=7864972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG104812A BG64649B1 (bg) | 1998-04-18 | 2000-09-29 | Нови дихидропиримидини |
Country Status (36)
| Country | Link |
|---|---|
| US (3) | US6696451B1 (cs) |
| EP (1) | EP1080086B1 (cs) |
| JP (2) | JP4590097B2 (cs) |
| KR (1) | KR100636771B1 (cs) |
| CN (1) | CN1159311C (cs) |
| AR (1) | AR018187A1 (cs) |
| AT (1) | ATE223401T1 (cs) |
| AU (1) | AU740318B2 (cs) |
| BG (1) | BG64649B1 (cs) |
| BR (2) | BR9909730B1 (cs) |
| CA (1) | CA2328780C (cs) |
| CO (1) | CO5021127A1 (cs) |
| CU (1) | CU23049A3 (cs) |
| CZ (1) | CZ293482B6 (cs) |
| DE (2) | DE19817264A1 (cs) |
| DK (1) | DK1080086T3 (cs) |
| ES (1) | ES2183548T3 (cs) |
| GT (1) | GT199900056A (cs) |
| HU (1) | HUP0102372A3 (cs) |
| ID (1) | ID27263A (cs) |
| IL (2) | IL138584A0 (cs) |
| MY (1) | MY126527A (cs) |
| NO (2) | NO321985B1 (cs) |
| NZ (1) | NZ507569A (cs) |
| PE (1) | PE20000427A1 (cs) |
| PL (1) | PL193898B1 (cs) |
| PT (1) | PT1080086E (cs) |
| RU (1) | RU2245881C9 (cs) |
| SI (1) | SI1080086T1 (cs) |
| SK (1) | SK286407B6 (cs) |
| SV (1) | SV1999000047A (cs) |
| TR (1) | TR200003011T2 (cs) |
| TW (1) | TW548274B (cs) |
| UA (1) | UA63998C2 (cs) |
| WO (1) | WO1999054326A1 (cs) |
| ZA (1) | ZA200005136B (cs) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000058302A1 (de) * | 1999-03-25 | 2000-10-05 | Bayer Aktiengesellschaft | Dihydropyrimidine und ihre verwendung zur behandlung von hepatitis b |
| WO2000078730A1 (en) | 1999-06-23 | 2000-12-28 | Ajinomoto Co., Inc. | Novel dihydropyrimidine derivatives |
| WO2001045712A1 (de) * | 1999-12-22 | 2001-06-28 | Bayer Aktiengesellschaft | Arzneimittelkombinationen gegen virale erkrankungen |
| DE10012823A1 (de) | 2000-03-16 | 2001-09-20 | Bayer Ag | Arzneimittel gegen virale Erkrankungen |
| DE10013126A1 (de) * | 2000-03-17 | 2001-09-20 | Bayer Ag | Arzneimittel gegen virale Erkrankungen |
| DE10013125A1 (de) * | 2000-03-17 | 2001-09-20 | Bayer Ag | Arzneimittel gegen virale Erkrankungen |
| DE10125131A1 (de) | 2001-05-23 | 2002-12-05 | Bayer Ag | Verfahren zur Spaltung des Methyl 4-(2-chlor-4-fluorphenyl)-2-(3,5-difluor-2-pyridinyl)-6-methyl-1,4-dihydro-5-pyrmidincarboxylat-Racemats |
| US20040092735A1 (en) * | 2002-11-08 | 2004-05-13 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of cefuroxime sodium |
| CN101104617B (zh) * | 2006-07-10 | 2010-06-23 | 北京摩力克科技有限公司 | 二氢嘧啶类化合物及其用于制备治疗和预防病毒性疾病的药物的用途 |
| CN101104604B (zh) * | 2006-07-10 | 2011-03-02 | 北京摩力克科技有限公司 | 光学纯二氢嘧啶类化合物及其用于制备治疗和预防病毒性疾病的药物的用途 |
| RU2452733C2 (ru) * | 2007-04-27 | 2012-06-10 | Пэдью Фарма Л.П. | Антагонисты trpv1 и их применение |
| WO2008154817A1 (en) | 2007-06-18 | 2008-12-24 | Zhang, Zhongneng | Bromo-phenyl substituted thiazolyl dihydropyrimidines |
| RU2493826C2 (ru) | 2007-07-12 | 2013-09-27 | Новартис Аг | Пероральные фармацевтические растворы, содержащие телбивудин |
| US20130267517A1 (en) | 2012-03-31 | 2013-10-10 | Hoffmann-La Roche Inc. | Novel 4-methyl-dihydropyrimidines for the treatment and prophylaxis of hepatitis b virus infection |
| EP2888241B1 (en) * | 2012-08-24 | 2017-07-12 | Sunshine Lake Pharma Co., Ltd. | 2,4,5,6-Substituted 3,6-dihydropyrimidine derivatives as hepatitis B virus (HBV) polymerase inhibitors for the treatment of e.g. chronic hepatitis |
| ES2617906T3 (es) | 2012-09-10 | 2017-06-20 | F. Hoffmann-La Roche Ag | 6-Aminoácido heteroarildihidropirimidinas para el tratamiento y la profilaxis de la infección por virus de la hepatitis B |
| CN103664899B (zh) * | 2012-09-11 | 2017-06-16 | 广东东阳光药业有限公司 | 杂芳基取代的二氢嘧啶类化合物及其在药物中的应用 |
| CN105051017A (zh) * | 2012-11-09 | 2015-11-11 | 美国印第安纳大学研究和技术公司 | 用于hbv组装效应剂的替代用途 |
| TW201609652A (zh) * | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（三） |
| CA2920415A1 (en) | 2013-11-19 | 2015-05-28 | Sunshine Lake Pharma Co., Ltd. | Dihydropyrimidine compounds and their application in pharmaceuticals |
| EP3074392B1 (en) | 2013-11-27 | 2019-04-03 | Sunshine Lake Pharma Co., Ltd. | Processes for preparing dihydropyrimidine derivatives and intermediates thereof |
| WO2015144093A1 (en) | 2014-03-28 | 2015-10-01 | Sunshine Lake Pharma Co., Ltd. | Dihydropyrimidine compounds and their application in pharmaceuticals |
| ES2687606T3 (es) | 2014-05-30 | 2018-10-26 | Qilu Pharmaceutical Co., Ltd. | Derivado de bucle de dihidropirimido como inhibidor de HBV |
| CN105153164B (zh) * | 2014-05-30 | 2018-10-30 | 齐鲁制药有限公司 | 作为hbv抑制剂的二氢嘧啶并环衍生物 |
| RU2017127611A (ru) | 2015-02-07 | 2019-03-07 | Саншайн Лейк Фарма Ко., Лтд. | Комплексные соединения и соли производных дигидропиримидина и их применение в фармацевтических препаратах |
| EP3645516A4 (en) * | 2017-06-27 | 2021-07-07 | Janssen Pharmaceutica NV | HETEROARYLDIHYDROPYRIMIDE DERIVATIVES AND METHODS OF TREATMENT OF HEPATITIS B INFECTIONS |
| US10759774B2 (en) | 2017-09-28 | 2020-09-01 | The Curators Of The University Of Missouri | Inhibitors of hepatitis B virus targeting capsid assembly |
| BR112020008762A2 (pt) | 2017-11-02 | 2020-10-20 | Aicuris Gmbh & Co. Kg | indol-2-carboxamidas amino-tiazol substituídas altamente ativas inovadoras ativas contra o vírus da hepatite b (hbv) |
| MX2020004838A (es) | 2017-11-02 | 2020-10-16 | Aicuris Gmbh & Co Kg | Nuevas indol-2-carboxamidas sustituidas con pirazolopiperidina, de alta actividad, activas contra el virus de la hepatitis b (vhb). |
| KR20210006412A (ko) * | 2018-05-08 | 2021-01-18 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 디히드로피리미딘 유도체 및 hbv 감염 또는 hbv-유도성 질환의 치료에 있어서의 이의 용도 |
| US11053235B2 (en) | 2018-08-09 | 2021-07-06 | Janssen Sciences Ireland Unlimited Company | Substituted 1,4-dihydropyrimidines for the treatment of HBV infection or HBV-induced diseases |
| AR117188A1 (es) | 2018-11-02 | 2021-07-21 | Aicuris Gmbh & Co Kg | Derivados de urea 6,7-dihidro-4h-pirazolo[1,5-a]pirazinas activas contra el virus de la hepatitis b (vhb) |
| UY38435A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Nuevas urea 6,7-dihidro-4h-pirazol[1,5-a] pirazinas activas contra el virus de la hepatitis b (vhb) |
| AR117189A1 (es) | 2018-11-02 | 2021-07-21 | Aicuris Gmbh & Co Kg | Derivados de 6,7-dihidro-4h-pirazolo[1,5-a]pirazin indol-2-carboxamidas activos contra el virus de la hepatitis b (vhb) |
| CN113039187A (zh) * | 2018-11-02 | 2021-06-25 | 艾库里斯有限及两合公司 | 抗乙型肝炎病毒HBV的脲6,7-二氢-4H-噻唑并[5,4-c]吡啶活性剂 |
| AR116946A1 (es) | 2018-11-02 | 2021-06-30 | Aicuris Gmbh & Co Kg | Derivados de urea 6,7-dihidro-4h-pirazolo[4,3-c]piridinas activas contra el virus de la hepatitis b (vhb) |
| UY38436A (es) | 2018-11-02 | 2020-05-29 | Aicuris Gmbh & Co Kg | Nuevas 6,7-dihidro-4h-pirazolo[1,5-a] pirazinindol-2-carboxamidas activas contra el virus de la hepatitis b (vhb) |
| KR20210106421A (ko) | 2018-12-20 | 2021-08-30 | 얀센 파마슈티카 엔.브이. | 헤테로아릴디히드로피리미딘 유도체 및 b형 간염 감염의 치료 방법 |
| CN113767101A (zh) | 2019-04-30 | 2021-12-07 | 艾库里斯有限及两合公司 | 具有抗乙型肝炎病毒(hbv)活性的新的吲哚-2-甲酰胺类化合物 |
| CU20210089A7 (es) | 2019-04-30 | 2022-06-06 | Aicuris Gmbh & Co Kg | Compuestos derivados de fenil y piridil ureas activas contra el virus de la hepatitis b (vhb) |
| AU2020265392A1 (en) | 2019-04-30 | 2021-12-23 | Aicuris Gmbh & Co. Kg | Novel indolizine-2-carboxamides active against the hepatitis B virus (HBV) |
| CN113748111A (zh) | 2019-04-30 | 2021-12-03 | 艾库里斯有限及两合公司 | 具有抗乙型肝炎病毒(hbv)活性的新型草酰哌嗪类化合物 |
| WO2020255016A1 (en) | 2019-06-18 | 2020-12-24 | Janssen Sciences Ireland Unlimited Company | Combination of hepatitis b virus (hbv) vaccines and dihydropyrimidine derivatives as capsid assembly modulators |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0103796A2 (de) * | 1982-09-18 | 1984-03-28 | Bayer Ag | Neue Dihydropyrimidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130304C (cs) * | 1964-02-12 | |||
| CH550189A (de) | 1971-01-08 | 1974-06-14 | Ciba Geigy Ag | Verfahren zur herstellung von neuen dibenzo (b,f) thiepincarbonsaeuren. |
| CH569043A5 (cs) | 1973-01-23 | 1975-11-14 | Ciba Geigy Ag | |
| US4371537A (en) * | 1981-08-13 | 1983-02-01 | The Dow Chemical Company | Sulfur-substituted phenoxypyridines having antiviral activity |
| JPS60185764A (ja) * | 1984-03-05 | 1985-09-21 | Wako Pure Chem Ind Ltd | ピリジン誘導体の新規な製造法 |
| US4698340A (en) * | 1984-07-19 | 1987-10-06 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine derivatives, processes for preparation thereof and composition containing the same |
| US4727073A (en) | 1984-10-01 | 1988-02-23 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine derivatives and composition of the same |
| GB8906168D0 (en) * | 1989-03-17 | 1989-05-04 | Pfizer Ltd | Therapeutic agents |
| EP0941222A2 (en) | 1996-11-12 | 1999-09-15 | Novartis AG | Pyrazole derivatives useful as herbicides |
| SE9702564D0 (sv) * | 1997-07-02 | 1997-07-02 | Astra Ab | New compounds |
-
1998
- 1998-04-18 DE DE19817264A patent/DE19817264A1/de not_active Withdrawn
-
1999
- 1999-04-07 ES ES99920603T patent/ES2183548T3/es not_active Expired - Lifetime
- 1999-04-07 US US09/673,592 patent/US6696451B1/en not_active Expired - Lifetime
- 1999-04-07 CA CA002328780A patent/CA2328780C/en not_active Expired - Lifetime
- 1999-04-07 JP JP2000544665A patent/JP4590097B2/ja not_active Expired - Lifetime
- 1999-04-07 AT AT99920603T patent/ATE223401T1/de active
- 1999-04-07 BR BRPI9909730-3A patent/BR9909730B1/pt not_active IP Right Cessation
- 1999-04-07 PT PT99920603T patent/PT1080086E/pt unknown
- 1999-04-07 EP EP99920603A patent/EP1080086B1/de not_active Expired - Lifetime
- 1999-04-07 KR KR1020007011527A patent/KR100636771B1/ko not_active Expired - Lifetime
- 1999-04-07 CZ CZ20003871A patent/CZ293482B6/cs not_active IP Right Cessation
- 1999-04-07 WO PCT/EP1999/002344 patent/WO1999054326A1/de not_active Ceased
- 1999-04-07 RU RU2000129148/04A patent/RU2245881C9/ru active
- 1999-04-07 TR TR2000/03011T patent/TR200003011T2/xx unknown
- 1999-04-07 CU CU20000220A patent/CU23049A3/es unknown
- 1999-04-07 DK DK99920603T patent/DK1080086T3/da active
- 1999-04-07 HU HU0102372A patent/HUP0102372A3/hu unknown
- 1999-04-07 SK SK1565-2000A patent/SK286407B6/sk not_active IP Right Cessation
- 1999-04-07 SI SI9930139T patent/SI1080086T1/xx unknown
- 1999-04-07 BR BRPI9917862A patent/BRPI9917862B8/pt not_active IP Right Cessation
- 1999-04-07 DE DE59902573T patent/DE59902573D1/de not_active Expired - Lifetime
- 1999-04-07 AU AU38133/99A patent/AU740318B2/en not_active Expired
- 1999-04-07 NZ NZ507569A patent/NZ507569A/en not_active IP Right Cessation
- 1999-04-07 CN CNB998074950A patent/CN1159311C/zh not_active Expired - Lifetime
- 1999-04-07 PL PL99343481A patent/PL193898B1/pl unknown
- 1999-04-07 IL IL13858499A patent/IL138584A0/xx active IP Right Grant
- 1999-04-07 ID IDW20002111A patent/ID27263A/id unknown
- 1999-04-15 PE PE1999000309A patent/PE20000427A1/es not_active IP Right Cessation
- 1999-04-16 SV SV1999000047A patent/SV1999000047A/es active IP Right Grant
- 1999-04-16 CO CO99022937A patent/CO5021127A1/es unknown
- 1999-04-16 TW TW088106067A patent/TW548274B/zh active
- 1999-04-16 MY MYPI99001481A patent/MY126527A/en unknown
- 1999-04-16 AR ARP990101779A patent/AR018187A1/es active IP Right Grant
- 1999-04-16 GT GT199900056A patent/GT199900056A/es unknown
- 1999-07-04 UA UA2000116511A patent/UA63998C2/uk unknown
-
2000
- 2000-09-20 IL IL138584A patent/IL138584A/en not_active IP Right Cessation
- 2000-09-26 ZA ZA200005136A patent/ZA200005136B/xx unknown
- 2000-09-29 BG BG104812A patent/BG64649B1/bg unknown
- 2000-10-17 NO NO20005215A patent/NO321985B1/no not_active IP Right Cessation
-
2004
- 2004-02-17 US US10/781,075 patent/US20040167135A1/en not_active Abandoned
- 2004-12-01 NO NO20045259A patent/NO329020B1/no not_active IP Right Cessation
-
2006
- 2006-12-15 US US11/639,955 patent/US7514565B2/en not_active Expired - Fee Related
-
2010
- 2010-07-23 JP JP2010165860A patent/JP5237332B2/ja not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0103796A2 (de) * | 1982-09-18 | 1984-03-28 | Bayer Ag | Neue Dihydropyrimidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln |
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