ZA200303690B - Imidazolone derivatives for the treatment of viral diseases. - Google Patents
Imidazolone derivatives for the treatment of viral diseases. Download PDFInfo
- Publication number
- ZA200303690B ZA200303690B ZA200303690A ZA200303690A ZA200303690B ZA 200303690 B ZA200303690 B ZA 200303690B ZA 200303690 A ZA200303690 A ZA 200303690A ZA 200303690 A ZA200303690 A ZA 200303690A ZA 200303690 B ZA200303690 B ZA 200303690B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- methyl
- dihydro
- phenyl
- substituted
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims description 21
- 201000010099 disease Diseases 0.000 title claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 19
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 title description 15
- 230000003612 virological effect Effects 0.000 title description 6
- -1 hydroxy-alky} Chemical group 0.000 claims description 633
- 150000001875 compounds Chemical class 0.000 claims description 137
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
- 125000001424 substituent group Chemical group 0.000 claims description 106
- 239000000460 chlorine Substances 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 229910052801 chlorine Inorganic materials 0.000 claims description 59
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 58
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 57
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 57
- 229910052794 bromium Inorganic materials 0.000 claims description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 53
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000004076 pyridyl group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 19
- 150000002170 ethers Chemical class 0.000 claims description 18
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 230000001404 mediated effect Effects 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- KQAJUDIIZSOUOC-UHFFFAOYSA-N 1-methyl-4-phenylsulfanyl-3-propan-2-yl-5-[(pyridin-4-ylmethylamino)methyl]imidazol-2-one Chemical compound C=1C=NC=CC=1CNCC=1N(C)C(=O)N(C(C)C)C=1SC1=CC=CC=C1 KQAJUDIIZSOUOC-UHFFFAOYSA-N 0.000 claims description 2
- GELMOEPGYAKMJA-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-1-methyl-5-(phenylmethoxymethyl)-3-propan-2-ylimidazol-2-one Chemical compound C=1C=CC=CC=1COCC=1N(C)C(=O)N(C(C)C)C=1OC1=CC(Cl)=CC(Cl)=C1 GELMOEPGYAKMJA-UHFFFAOYSA-N 0.000 claims description 2
- USNIDRLIIXNZLH-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-5-(hydroxymethyl)-1-methyl-3-propan-2-ylimidazol-2-one Chemical compound CN1C(=O)N(C(C)C)C(SC=2C=C(Cl)C=C(Cl)C=2)=C1CO USNIDRLIIXNZLH-UHFFFAOYSA-N 0.000 claims description 2
- UEMAXFKMGOGVDZ-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)sulfanyl-5-[(2-hydroxyphenyl)methyl]-1-methyl-3-propan-2-ylimidazol-2-one Chemical compound C=1C=CC=C(O)C=1CC=1N(C)C(=O)N(C(C)C)C=1SC1=CC(Cl)=CC(Cl)=C1 UEMAXFKMGOGVDZ-UHFFFAOYSA-N 0.000 claims description 2
- XTQPOASEIPNSHI-UHFFFAOYSA-N 5-benzyl-1-methyl-4-methylsulfanyl-3-propan-2-ylimidazol-2-one Chemical compound CN1C(=O)N(C(C)C)C(SC)=C1CC1=CC=CC=C1 XTQPOASEIPNSHI-UHFFFAOYSA-N 0.000 claims description 2
- JFSAWLISEWQWOD-UHFFFAOYSA-N 5-benzyl-4-(3,5-dichlorophenyl)sulfanyl-1-methyl-3-propan-2-ylimidazol-2-one Chemical compound C=1C=CC=CC=1CC=1N(C)C(=O)N(C(C)C)C=1SC1=CC(Cl)=CC(Cl)=C1 JFSAWLISEWQWOD-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 8
- UPCCRTUUTXEQKZ-UHFFFAOYSA-N 1,3-dibenzyl-4-(3,5-dichlorophenyl)sulfanyl-5-[(pyridin-4-ylmethylamino)methyl]imidazol-2-one Chemical compound ClC1=CC(Cl)=CC(SC=2N(C(=O)N(CC=3C=CC=CC=3)C=2CNCC=2C=CN=CC=2)CC=2C=CC=CC=2)=C1 UPCCRTUUTXEQKZ-UHFFFAOYSA-N 0.000 claims 1
- VRRZFUURQCYQJC-UHFFFAOYSA-N 1-benzyl-4-(3,5-dichlorophenyl)sulfanyl-3-propyl-5-[(pyridin-4-ylmethylamino)methyl]imidazol-2-one Chemical compound C=1C=NC=CC=1CNCC=1N(CC=2C=CC=CC=2)C(=O)N(CCC)C=1SC1=CC(Cl)=CC(Cl)=C1 VRRZFUURQCYQJC-UHFFFAOYSA-N 0.000 claims 1
- KCQRKOFYTWSAPC-UHFFFAOYSA-N 1-benzyl-5-(3,5-dichlorophenyl)sulfanyl-4-(1-hydroxyethyl)-3-methylimidazol-2-one Chemical compound C=1C=CC=CC=1CN1C(=O)N(C)C(C(O)C)=C1SC1=CC(Cl)=CC(Cl)=C1 KCQRKOFYTWSAPC-UHFFFAOYSA-N 0.000 claims 1
- RYJDQQUYQJLZHC-UHFFFAOYSA-N 1-benzyl-5-(3,5-dichlorophenyl)sulfanyl-4-(hydroxymethyl)-3-methylimidazol-2-one Chemical compound C=1C=CC=CC=1CN1C(=O)N(C)C(CO)=C1SC1=CC(Cl)=CC(Cl)=C1 RYJDQQUYQJLZHC-UHFFFAOYSA-N 0.000 claims 1
- KISDUHTWPMAMEB-UHFFFAOYSA-N 1-methyl-3-propan-2-yl-4-propan-2-ylsulfanyl-5-[(pyridin-4-ylmethylamino)methyl]imidazol-2-one Chemical compound CN1C(=O)N(C(C)C)C(SC(C)C)=C1CNCC1=CC=NC=C1 KISDUHTWPMAMEB-UHFFFAOYSA-N 0.000 claims 1
- LXKGQDLZEMXESH-UHFFFAOYSA-N 1-methyl-4-(2-methylpropylsulfanyl)-3-propan-2-yl-5-[(pyridin-4-ylmethylamino)methyl]imidazol-2-one Chemical compound CN1C(=O)N(C(C)C)C(SCC(C)C)=C1CNCC1=CC=NC=C1 LXKGQDLZEMXESH-UHFFFAOYSA-N 0.000 claims 1
- MYPVRGIHFSSJRF-UHFFFAOYSA-N 3-(5-benzyl-1-methyl-2-oxo-3-propan-2-ylimidazol-4-yl)sulfanylbenzonitrile Chemical compound C=1C=CC=CC=1CC=1N(C)C(=O)N(C(C)C)C=1SC1=CC=CC(C#N)=C1 MYPVRGIHFSSJRF-UHFFFAOYSA-N 0.000 claims 1
- YEHHFIDXSIUCQI-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)sulfanyl-3-methyl-2-oxo-1-propan-2-ylimidazol-4-yl]prop-2-enamide Chemical compound CN1C(=O)N(C(C)C)C(SC=2C=C(Cl)C=C(Cl)C=2)=C1C=CC(N)=O YEHHFIDXSIUCQI-UHFFFAOYSA-N 0.000 claims 1
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- PWMMGEBWJGLWSF-UHFFFAOYSA-N 5-(hydroxymethyl)-1-methyl-3-phenyl-4-pyridin-4-ylsulfanylimidazol-2-one Chemical compound C=1C=CC=CC=1N1C(=O)N(C)C(CO)=C1SC1=CC=NC=C1 PWMMGEBWJGLWSF-UHFFFAOYSA-N 0.000 claims 1
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- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000006379 fluoropyridyl group Chemical group 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000006301 indolyl methyl group Chemical group 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DCNUQRBLZWSGAV-UHFFFAOYSA-N n,n-diphenylformamide Chemical compound C=1C=CC=CC=1N(C=O)C1=CC=CC=C1 DCNUQRBLZWSGAV-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 229940127073 nucleoside analogue Drugs 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- ZHOVAWFVVBWEGQ-UHFFFAOYSA-N tripropylsilane Chemical compound CCC[SiH](CCC)CCC ZHOVAWFVVBWEGQ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 206010055031 vascular neoplasm Diseases 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0028484.4A GB0028484D0 (en) | 2000-11-22 | 2000-11-22 | Imidazolone derivatives for the treatment of viral diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200303690B true ZA200303690B (en) | 2004-08-13 |
Family
ID=9903671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200303690A ZA200303690B (en) | 2000-11-22 | 2003-05-13 | Imidazolone derivatives for the treatment of viral diseases. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6518293B2 (de) |
| EP (1) | EP1341766B1 (de) |
| JP (1) | JP2004514672A (de) |
| KR (1) | KR100528760B1 (de) |
| CN (1) | CN1633417A (de) |
| AR (1) | AR035372A1 (de) |
| AT (1) | ATE307805T1 (de) |
| AU (2) | AU2002221842B2 (de) |
| BR (1) | BR0115476A (de) |
| CA (1) | CA2428461A1 (de) |
| DE (1) | DE60114448T2 (de) |
| DK (1) | DK1341766T3 (de) |
| ES (1) | ES2251529T3 (de) |
| GB (1) | GB0028484D0 (de) |
| MX (1) | MXPA03004454A (de) |
| PA (1) | PA8533301A1 (de) |
| PE (1) | PE20020636A1 (de) |
| UY (1) | UY27035A1 (de) |
| WO (1) | WO2002042279A1 (de) |
| ZA (1) | ZA200303690B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200423930A (en) * | 2003-02-18 | 2004-11-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| WO2005100322A1 (en) * | 2004-04-14 | 2005-10-27 | Pfizer Limited | Sulphur-linked imidazole compounds for the treament of hiv |
| EP1838679A1 (de) * | 2005-01-06 | 2007-10-03 | Pfizer Limited | Imidazolderivate als modulatoren des enzyms reverse transkriptase |
| WO2008085008A1 (en) * | 2007-01-11 | 2008-07-17 | Mogam Biotechnology Research Institute | T-cell inhibiting compounds and their use for the treatment of t-cell-mediated diseases |
| KR101110120B1 (ko) * | 2009-10-28 | 2012-01-31 | 주식회사 케이아이테크놀로지 | 표지판 완충장치 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4345936A (en) * | 1981-10-05 | 1982-08-24 | Eli Lilly And Company | Imidazoles, compositions and herbicidal method |
| TW235963B (de) | 1992-01-16 | 1994-12-11 | Shionogi & Co | |
| WO1993015060A1 (en) | 1992-01-22 | 1993-08-05 | Nissan Chemical Industries, Ltd. | Substituted pyrazole derivative and agrohorticultural bactericide |
| GB9222262D0 (en) | 1992-10-23 | 1992-12-09 | Merck Sharp & Dohme | Therapeutic agents |
| US5612636A (en) * | 1995-01-19 | 1997-03-18 | Texas Instruments Incorporated | Short circuit power optimization for CMOS circuits |
| US5612363A (en) | 1995-06-02 | 1997-03-18 | Berlex Laboratories, Inc. | N,N-di(aryl) cyclic urea derivatives as anti-coagulants |
| US6046331A (en) * | 1998-12-17 | 2000-04-04 | Synaptic Pharmaceutical Corporation | Imidazolones and their use in treating benign prostatic hyperplasia and other disorders |
-
2000
- 2000-11-22 GB GBGB0028484.4A patent/GB0028484D0/en not_active Ceased
-
2001
- 2001-11-06 US US09/993,848 patent/US6518293B2/en not_active Expired - Fee Related
- 2001-11-12 AU AU2002221842A patent/AU2002221842B2/en not_active Ceased
- 2001-11-12 BR BR0115476-1A patent/BR0115476A/pt not_active IP Right Cessation
- 2001-11-12 CA CA002428461A patent/CA2428461A1/en not_active Abandoned
- 2001-11-12 DE DE60114448T patent/DE60114448T2/de not_active Expired - Fee Related
- 2001-11-12 EP EP01997479A patent/EP1341766B1/de not_active Expired - Lifetime
- 2001-11-12 AU AU2184202A patent/AU2184202A/xx active Pending
- 2001-11-12 CN CNA018193528A patent/CN1633417A/zh active Pending
- 2001-11-12 AT AT01997479T patent/ATE307805T1/de not_active IP Right Cessation
- 2001-11-12 ES ES01997479T patent/ES2251529T3/es not_active Expired - Lifetime
- 2001-11-12 DK DK01997479T patent/DK1341766T3/da active
- 2001-11-12 JP JP2002544414A patent/JP2004514672A/ja active Pending
- 2001-11-12 KR KR10-2003-7006881A patent/KR100528760B1/ko not_active IP Right Cessation
- 2001-11-12 WO PCT/EP2001/013069 patent/WO2002042279A1/en active IP Right Grant
- 2001-11-12 MX MXPA03004454A patent/MXPA03004454A/es active IP Right Grant
- 2001-11-20 PE PE2001001158A patent/PE20020636A1/es not_active Application Discontinuation
- 2001-11-21 AR ARP010105422A patent/AR035372A1/es not_active Application Discontinuation
- 2001-11-21 UY UY27035A patent/UY27035A1/es not_active Application Discontinuation
- 2001-11-21 PA PA20018533301A patent/PA8533301A1/es unknown
-
2003
- 2003-05-13 ZA ZA200303690A patent/ZA200303690B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA03004454A (es) | 2003-08-19 |
| AU2002221842B2 (en) | 2007-08-23 |
| BR0115476A (pt) | 2003-08-19 |
| AU2184202A (en) | 2002-06-03 |
| EP1341766A1 (de) | 2003-09-10 |
| AR035372A1 (es) | 2004-05-12 |
| DE60114448T2 (de) | 2006-07-06 |
| PE20020636A1 (es) | 2002-07-18 |
| WO2002042279A1 (en) | 2002-05-30 |
| ES2251529T3 (es) | 2006-05-01 |
| CA2428461A1 (en) | 2002-05-30 |
| EP1341766B1 (de) | 2005-10-26 |
| KR20030060951A (ko) | 2003-07-16 |
| JP2004514672A (ja) | 2004-05-20 |
| DE60114448D1 (de) | 2005-12-01 |
| CN1633417A (zh) | 2005-06-29 |
| DK1341766T3 (da) | 2006-02-20 |
| US6518293B2 (en) | 2003-02-11 |
| PA8533301A1 (es) | 2002-08-26 |
| KR100528760B1 (ko) | 2005-11-15 |
| GB0028484D0 (en) | 2001-01-10 |
| ATE307805T1 (de) | 2005-11-15 |
| US20020107272A1 (en) | 2002-08-08 |
| UY27035A1 (es) | 2002-06-20 |
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