ZA200006037B - 3-(Amino- or aminoalkyl) pyridinone derivatives and their use for the treatment of HIV related diseases. - Google Patents
3-(Amino- or aminoalkyl) pyridinone derivatives and their use for the treatment of HIV related diseases. Download PDFInfo
- Publication number
- ZA200006037B ZA200006037B ZA200006037A ZA200006037A ZA200006037B ZA 200006037 B ZA200006037 B ZA 200006037B ZA 200006037 A ZA200006037 A ZA 200006037A ZA 200006037 A ZA200006037 A ZA 200006037A ZA 200006037 B ZA200006037 B ZA 200006037B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyridinone
- amino
- substituted
- group
- hydrogen
- Prior art date
Links
- 150000005299 pyridinones Chemical class 0.000 title claims description 9
- 238000011282 treatment Methods 0.000 title claims description 8
- 201000010099 disease Diseases 0.000 title claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 30
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- -1 dimethylenoxy Chemical group 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 208000031886 HIV Infections Diseases 0.000 claims description 3
- 208000037357 HIV infectious disease Diseases 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 150000003935 benzaldehydes Chemical class 0.000 claims description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 230000001131 transforming effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- FHQCHOTUQBIXHY-UHFFFAOYSA-N 3-(dimethylamino)-4-[(3,5-dimethylphenyl)methyl]-5-ethyl-6-methyl-1h-pyridin-2-one Chemical compound CCC1=C(C)NC(=O)C(N(C)C)=C1CC1=CC(C)=CC(C)=C1 FHQCHOTUQBIXHY-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 241000725303 Human immunodeficiency virus Species 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- YNOHDVUYAXBTFK-UHFFFAOYSA-N n-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)-2,2-dimethylpropanamide Chemical compound CCC1=CC(NC(=O)C(C)(C)C)=C(OC)N=C1C YNOHDVUYAXBTFK-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QXDHXCVJGBTQMK-UHFFFAOYSA-N 1-(bromomethyl)-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(CBr)=C1 QXDHXCVJGBTQMK-UHFFFAOYSA-N 0.000 description 2
- HDMHBHNRWDNNCD-UHFFFAOYSA-N 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine Chemical compound OCCOCN1C(=O)NC(=O)C(C)=C1SC1=CC=CC=C1 HDMHBHNRWDNNCD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 description 2
- 101900297506 Human immunodeficiency virus type 1 group M subtype B Reverse transcriptase/ribonuclease H Proteins 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- SPXOYLTWMNEOCK-UHFFFAOYSA-N n-[4-[(3,5-dimethylphenyl)methyl]-5-ethyl-2-methoxy-6-methylpyridin-3-yl]-2,2-dimethylpropanamide Chemical compound CCC1=C(C)N=C(OC)C(NC(=O)C(C)(C)C)=C1CC1=CC(C)=CC(C)=C1 SPXOYLTWMNEOCK-UHFFFAOYSA-N 0.000 description 2
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 1
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 1
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 description 1
- CGSPVYCZBDFPHJ-UHFFFAOYSA-N 2,2-dimethyl-n-pyridin-2-ylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC=N1 CGSPVYCZBDFPHJ-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- DUCPUVTUDGVTHV-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)-2-[3-(2,2-dimethylpropanoylamino)-5-ethyl-2-methoxy-6-methylpyridin-4-yl]propanoic acid Chemical compound CCC1=C(C)N=C(OC)C(NC(=O)C(C)(C)C)=C1C(C)(C(O)=O)C1=CC(C)=CC(C)=C1 DUCPUVTUDGVTHV-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- 238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- NILMGJQQKLECIG-UHFFFAOYSA-N [(3,5-dimethylphenyl)-[3-(2,2-dimethylpropanoylamino)-5-ethyl-2-methoxy-6-methylpyridin-4-yl]methyl] acetate Chemical compound CCC1=C(C)N=C(OC)C(NC(=O)C(C)(C)C)=C1C(OC(C)=O)C1=CC(C)=CC(C)=C1 NILMGJQQKLECIG-UHFFFAOYSA-N 0.000 description 1
- YMQSEUMDCRELKC-UHFFFAOYSA-N acetic acid;1,4-dioxane;hydrate Chemical compound O.CC(O)=O.C1COCCO1 YMQSEUMDCRELKC-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229960000689 nevirapine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D409/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8308298P | 1998-04-27 | 1998-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200006037B true ZA200006037B (en) | 2002-01-25 |
Family
ID=22176061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200006037A ZA200006037B (en) | 1998-04-27 | 2000-10-25 | 3-(Amino- or aminoalkyl) pyridinone derivatives and their use for the treatment of HIV related diseases. |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US6451822B1 (xx) |
| EP (1) | EP1073637B1 (xx) |
| JP (1) | JP2002513004A (xx) |
| KR (1) | KR20010087128A (xx) |
| CN (1) | CN1303378A (xx) |
| AP (1) | AP2000001991A0 (xx) |
| AT (1) | ATE334966T1 (xx) |
| AU (1) | AU4137899A (xx) |
| BG (1) | BG104984A (xx) |
| BR (1) | BR9909976A (xx) |
| CA (1) | CA2330304A1 (xx) |
| CZ (1) | CZ20003978A3 (xx) |
| DE (1) | DE69932611T2 (xx) |
| EE (1) | EE200000620A (xx) |
| HR (1) | HRP20000716A2 (xx) |
| HU (1) | HUP0101595A3 (xx) |
| ID (1) | ID27502A (xx) |
| IL (1) | IL139239A0 (xx) |
| MX (1) | MXPA00010490A (xx) |
| NO (1) | NO20005387L (xx) |
| NZ (1) | NZ508297A (xx) |
| PL (1) | PL343685A1 (xx) |
| RU (1) | RU2000129671A (xx) |
| SK (1) | SK16072000A3 (xx) |
| TR (1) | TR200003113T2 (xx) |
| WO (1) | WO1999055676A1 (xx) |
| ZA (1) | ZA200006037B (xx) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6436972B1 (en) * | 2000-04-10 | 2002-08-20 | Dalhousie University | Pyridones and their use as modulators of serine hydrolase enzymes |
| AU2001282938A1 (en) * | 2000-07-21 | 2002-02-05 | Elan Pharmaceuticals, Inc. | Alpha amino acid derivatives--inhibitors of leukocyte adhesion mediated by vla-4 |
| JP2004509867A (ja) * | 2000-09-19 | 2004-04-02 | サントル、ナショナール、ド、ラ、ルシェルシュ、シアンティフィク、（セーエヌエルエス） | Ｈｉｖ阻害特性を有するピリジノンおよびピリジンチオン誘導体 |
| US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| EP1465869B1 (en) | 2001-12-21 | 2013-05-15 | Exelixis Patent Company LLC | Modulators of lxr |
| US7642277B2 (en) * | 2002-12-04 | 2010-01-05 | Boehringer Ingelheim International Gmbh | Non-nucleoside reverse transcriptase inhibitors |
| BRPI0408704A (pt) * | 2003-03-24 | 2006-03-07 | Hoffmann La Roche | benzil-piridazinonas como inibidores de transcriptase reversa |
| EP1516873A1 (en) * | 2003-09-22 | 2005-03-23 | Facultés Universitaires Notre-Dame de la Paix | 2-pyridinone derivatives, having HIV inhibiting properties |
| US7622582B2 (en) * | 2004-05-17 | 2009-11-24 | Tibotec Bvba | Derivatives of 1-phenyl-benzofuro[3,2]pyridin-2(1H)-one |
| GB0420722D0 (en) * | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| CA2605214C (en) * | 2004-12-31 | 2016-07-12 | Reddy Us Therapeutics, Inc. | Benzylamine derivatives as cetp inhibitors |
| ES2524922T3 (es) | 2005-05-10 | 2014-12-15 | Intermune, Inc. | Derivados de piridona para modular el sistema de proteína cinasa activada por estrés |
| WO2007027729A1 (en) | 2005-08-29 | 2007-03-08 | Vertex Pharmaceuticals Incorporated | 3, 5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-receptor tyrosine kinases |
| ES2361338T3 (es) | 2005-08-29 | 2011-06-16 | Vertex Pharmaceuticals Incorporated | Pirid-2-onas 3,5-disustituidas útiles como inhibidores de la familia tec de tirosina quinasas no ligadas a receptor. |
| CA2620269A1 (en) | 2005-08-29 | 2007-03-08 | Vertex Pharmaceuticals Incorporated | 3,5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-receptor tyrosine kinases |
| WO2007075487A2 (en) * | 2005-12-19 | 2007-07-05 | Syngenta Limited | Substituted aromatic heterocyclic compounds as fungicides |
| JP5539216B2 (ja) * | 2007-11-20 | 2014-07-02 | メルク・シャープ・アンド・ドーム・コーポレーション | 非ヌクレオシド系逆転写酵素阻害剤 |
| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| KR20110041515A (ko) * | 2008-07-14 | 2011-04-21 | 한국화학연구원 | 비-뉴클레오사이드 역전사효소 억제제로서의 피리돈 유도체 |
| US8318737B2 (en) | 2009-09-02 | 2012-11-27 | Canthera Therapeutics Inc. | Compounds and compositions for treating cancer |
| US8349832B2 (en) * | 2009-09-02 | 2013-01-08 | Canthera Therapeutics | Compounds and compositions for treating cancer |
| CN102001994B (zh) * | 2010-10-22 | 2014-07-09 | 北京大学 | 吡啶酮类hiv-1逆转录酶抑制剂的制备及其应用 |
| CN103288719A (zh) * | 2012-03-05 | 2013-09-11 | 苏州欧凯医药技术有限公司 | 非核甘艾滋病毒抑制物-吡啶酮类先导体的合成 |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| JO3470B1 (ar) | 2012-10-08 | 2020-07-05 | Merck Sharp & Dohme | مشتقات 5- فينوكسي-3h-بيريميدين-4-أون واستخدامها كمثبطات ناسخ عكسي ل hiv |
| US10233195B2 (en) | 2014-04-02 | 2019-03-19 | Intermune, Inc. | Anti-fibrotic pyridinones |
| AU2015308350B2 (en) | 2014-08-29 | 2020-03-05 | Tes Pharma S.R.L. | Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase |
| KR102645602B1 (ko) * | 2018-12-18 | 2024-03-07 | 머크 샤프 앤드 돔 엘엘씨 | Hiv 감염된 세포에 대한 선택적 세포독성제로서의 피리미돈 유도체 |
| CA3141143A1 (en) * | 2019-05-22 | 2020-11-26 | Merck Sharp & Dohme Corp. | Pyridinone derivatives as selective cytotoxic agents against hiv infected cells |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL98526A0 (en) * | 1990-06-18 | 1992-07-15 | Merck & Co Inc | Pyridones,processes for their preparation and pharmaceutical compositions containing them |
| US5308854A (en) * | 1990-06-18 | 1994-05-03 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
| FR2737496B1 (fr) * | 1995-07-31 | 1997-12-19 | Centre Nat Rech Scient | 4-aryl-thio-pyridin-2(1h)-ones, medicaments les contenant et leurs utilisations dans le traitement de maladies liees aux vih 1 et 2 |
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1999
- 1999-04-27 TR TR2000/03113T patent/TR200003113T2/xx unknown
- 1999-04-27 EP EP99924870A patent/EP1073637B1/en not_active Expired - Lifetime
- 1999-04-27 DE DE69932611T patent/DE69932611T2/de not_active Expired - Lifetime
- 1999-04-27 JP JP2000545836A patent/JP2002513004A/ja not_active Withdrawn
- 1999-04-27 HU HU0101595A patent/HUP0101595A3/hu unknown
- 1999-04-27 CN CN99806829A patent/CN1303378A/zh active Pending
- 1999-04-27 CA CA002330304A patent/CA2330304A1/en not_active Abandoned
- 1999-04-27 KR KR1020007011918A patent/KR20010087128A/ko not_active Application Discontinuation
- 1999-04-27 RU RU2000129671/04A patent/RU2000129671A/ru unknown
- 1999-04-27 AU AU41378/99A patent/AU4137899A/en not_active Abandoned
- 1999-04-27 AT AT99924870T patent/ATE334966T1/de not_active IP Right Cessation
- 1999-04-27 MX MXPA00010490A patent/MXPA00010490A/es unknown
- 1999-04-27 AP APAP/P/2000/001991A patent/AP2000001991A0/en unknown
- 1999-04-27 EE EEP200000620A patent/EE200000620A/xx unknown
- 1999-04-27 US US09/673,635 patent/US6451822B1/en not_active Expired - Fee Related
- 1999-04-27 PL PL99343685A patent/PL343685A1/xx unknown
- 1999-04-27 BR BR9909976-4A patent/BR9909976A/pt not_active IP Right Cessation
- 1999-04-27 NZ NZ508297A patent/NZ508297A/xx unknown
- 1999-04-27 SK SK1607-2000A patent/SK16072000A3/sk unknown
- 1999-04-27 CZ CZ20003978A patent/CZ20003978A3/cs unknown
- 1999-04-27 WO PCT/EP1999/003023 patent/WO1999055676A1/en active IP Right Grant
- 1999-04-27 ID IDW20002191A patent/ID27502A/id unknown
- 1999-04-27 IL IL13923999A patent/IL139239A0/xx unknown
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2000
- 2000-10-23 HR HR20000716A patent/HRP20000716A2/hr not_active Application Discontinuation
- 2000-10-25 ZA ZA200006037A patent/ZA200006037B/en unknown
- 2000-10-26 NO NO20005387A patent/NO20005387L/no not_active Application Discontinuation
- 2000-11-24 BG BG104984A patent/BG104984A/xx unknown
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2002
- 2002-07-15 US US10/194,240 patent/US6683079B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69932611D1 (de) | 2006-09-14 |
| US6683079B2 (en) | 2004-01-27 |
| CZ20003978A3 (cs) | 2001-09-12 |
| PL343685A1 (en) | 2001-08-27 |
| AU4137899A (en) | 1999-11-16 |
| CA2330304A1 (en) | 1999-11-04 |
| JP2002513004A (ja) | 2002-05-08 |
| AP2000001991A0 (en) | 2000-12-31 |
| RU2000129671A (ru) | 2004-02-20 |
| CN1303378A (zh) | 2001-07-11 |
| HUP0101595A2 (hu) | 2001-11-28 |
| ID27502A (id) | 2001-04-12 |
| ATE334966T1 (de) | 2006-08-15 |
| MXPA00010490A (es) | 2002-10-17 |
| SK16072000A3 (sk) | 2002-04-04 |
| TR200003113T2 (tr) | 2001-05-21 |
| KR20010087128A (ko) | 2001-09-15 |
| NO20005387D0 (no) | 2000-10-26 |
| IL139239A0 (en) | 2001-11-25 |
| EP1073637A1 (en) | 2001-02-07 |
| NZ508297A (en) | 2002-12-20 |
| HRP20000716A2 (en) | 2001-06-30 |
| HUP0101595A3 (en) | 2002-12-28 |
| US6451822B1 (en) | 2002-09-17 |
| EP1073637B1 (en) | 2006-08-02 |
| DE69932611T2 (de) | 2007-10-11 |
| WO1999055676A1 (en) | 1999-11-04 |
| US20030125340A1 (en) | 2003-07-03 |
| BG104984A (en) | 2001-07-31 |
| BR9909976A (pt) | 2000-12-26 |
| EE200000620A (et) | 2002-04-15 |
| NO20005387L (no) | 2000-12-04 |
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