HRP20010310A2 - 2,4-disubstituted triazine derivatives - Google Patents

2,4-disubstituted triazine derivatives Download PDF

Info

Publication number: HRP20010310A2
Authority: HR; Croatia
Prior art keywords: alkyl; cyano; formula; substituents; substituted
Prior art date: 1998-11-10

Application number

HR20010310A

Other languages

English (en)

Croatian (hr)

Inventor

Bart De Corte

Marc Rene De Longe

Jan Heeres

Paul Adriaan Jan Janssen

Robert W Kavash

Lucien Maria Henricus Koymans

Michael Joseph Kukla

Donald William Ludovici

Koen Jeanne Alfons Van Aken

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-11-10

Filing date

2001-05-02

Publication date

2002-06-30

2001-05-02 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2002-06-30 Publication of HRP20010310A2 publication Critical patent/HRP20010310A2/hr

Links

-1 2,4-disubstituted triazine Chemical class 0.000 title claims description 101
150000001875 compounds Chemical class 0.000 claims description 109
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 54
125000001424 substituent group Chemical group 0.000 claims description 51
150000003839 salts Chemical class 0.000 claims description 38
125000004093 cyano group Chemical group *C#N 0.000 claims description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 24
150000002367 halogens Chemical group 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 24
241000725303 Human immunodeficiency virus Species 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 21
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
150000001204 N-oxides Chemical class 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
150000001412 amines Chemical class 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 13
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
125000003373 pyrazinyl group Chemical group 0.000 claims description 12
125000002098 pyridazinyl group Chemical group 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
239000002585 base Substances 0.000 claims description 10
125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 9
230000000798 anti-retroviral effect Effects 0.000 claims description 9
239000003937 drug carrier Substances 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 8
229940079593 drug Drugs 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 6
125000001931 aliphatic group Chemical class 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 6
125000001041 indolyl group Chemical group 0.000 claims description 6
208000015181 infectious disease Diseases 0.000 claims description 6
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
230000036436 anti-hiv Effects 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
238000010306 acid treatment Methods 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
229920000858 Cyclodextrin Polymers 0.000 description 24
239000000543 intermediate Substances 0.000 description 23
239000000203 mixture Substances 0.000 description 18
150000003254 radicals Chemical class 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 17
239000007787 solid Substances 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
235000019439 ethyl acetate Nutrition 0.000 description 14
239000000243 solution Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 11
229940097362 cyclodextrins Drugs 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
239000002552 dosage form Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000002245 particle Substances 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
238000010992 reflux Methods 0.000 description 7
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
229920003169 water-soluble polymer Polymers 0.000 description 7
208000031886 HIV Infections Diseases 0.000 description 6
208000037357 HIV infectious disease Diseases 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000000843 powder Substances 0.000 description 6
229930195734 saturated hydrocarbon Natural products 0.000 description 6
239000000725 suspension Substances 0.000 description 6
206010001513 AIDS related complex Diseases 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
238000004949 mass spectrometry Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000000750 progressive effect Effects 0.000 description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
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
208000030507 AIDS Diseases 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
241000713772 Human immunodeficiency virus 1 Species 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000007888 film coating Substances 0.000 description 3
238000009501 film coating Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
230000010076 replication Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000007962 solid dispersion Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
241001430294 unidentified retrovirus Species 0.000 description 3
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical compound ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 2
NAFOOGOADMAIJN-UHFFFAOYSA-N 2-anilino-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)NC1=CC=CC=C1 NAFOOGOADMAIJN-UHFFFAOYSA-N 0.000 description 2
CDEBTESVXBOETJ-UHFFFAOYSA-N 2-n,4-n-dipyridin-2-yl-1,3,5-triazine-2,4-diamine Chemical compound N=1C=NC(NC=2N=CC=CC=2)=NC=1NC1=CC=CC=N1 CDEBTESVXBOETJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
206010012289 Dementia Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
208000008771 Lymphadenopathy Diseases 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000012223 aqueous fraction Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
229960002656 didanosine Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
229920001477 hydrophilic polymer Polymers 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000011777 magnesium Chemical class 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 2
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
230000001717 pathogenic effect Effects 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000006187 pill Substances 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 2
229960001685 tacrine Drugs 0.000 description 2
238000012360 testing method Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
DFHAXXVZCFXGOQ-UHFFFAOYSA-K trisodium phosphonoformate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O DFHAXXVZCFXGOQ-UHFFFAOYSA-K 0.000 description 2
229960002555 zidovudine Drugs 0.000 description 2
PCWPQSDFNIFUPO-VDQKLNDWSA-N (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-37,39,41,43,45,47,49-heptakis(2-hydroxyethoxy)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38,40,42,44,46,48-heptol Chemical compound OCCO[C@H]1[C@H](O)[C@@H]2O[C@H]3O[C@H](CO)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O[C@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O[C@H]8O[C@H](CO)[C@@H](O[C@H]1O[C@@H]2CO)[C@@H](O)[C@@H]8OCCO)[C@@H](O)[C@@H]7OCCO)[C@@H](O)[C@@H]6OCCO)[C@@H](O)[C@@H]5OCCO)[C@@H](O)[C@@H]4OCCO)[C@@H](O)[C@@H]3OCCO PCWPQSDFNIFUPO-VDQKLNDWSA-N 0.000 description 1
XTYSXGHMTNTKFH-BDEHJDMKSA-N (2s)-1-[(2s,4r)-4-benzyl-2-hydroxy-5-[[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-5-oxopentyl]-n-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide;hydrate Chemical compound O.C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 XTYSXGHMTNTKFH-BDEHJDMKSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
125000006002 1,1-difluoroethyl group Chemical group 0.000 description 1
IMAQBISTCDGKII-UHFFFAOYSA-N 1,3,10-triazatricyclo[6.4.1.04,13]trideca-4,6,8(13)-trien-2-one Chemical compound C1NCCN2C(=O)NC3=CC=CC1=C32 IMAQBISTCDGKII-UHFFFAOYSA-N 0.000 description 1
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
150000000182 1,3,5-triazines Chemical class 0.000 description 1
KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
PKANQZUPJCMBAK-UHFFFAOYSA-N 2,4,6-trimethylbenzenethiol Chemical compound CC1=CC(C)=C(S)C(C)=C1 PKANQZUPJCMBAK-UHFFFAOYSA-N 0.000 description 1
BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
CJEBZUFROMNDEK-UHFFFAOYSA-N 2,6-dibromo-4-propan-2-ylaniline Chemical compound CC(C)C1=CC(Br)=C(N)C(Br)=C1 CJEBZUFROMNDEK-UHFFFAOYSA-N 0.000 description 1
BSFPWNBIKBSHRL-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-2-(2-nitroanilino)acetamide Chemical compound ClC=1C=CC=C(Cl)C=1C(C(=O)N)NC1=CC=CC=C1[N+]([O-])=O BSFPWNBIKBSHRL-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
YPWVBRGRUTXFMK-UHFFFAOYSA-N 2-n,2-n-dipyridin-2-yl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N(C=2N=CC=CC=2)C=2N=CC=CC=2)=N1 YPWVBRGRUTXFMK-UHFFFAOYSA-N 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
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000006041 3-hexenyl group Chemical group 0.000 description 1
CHKFMKBFNPZSAN-UHFFFAOYSA-N 4-[(4-chloro-1,3,5-triazin-2-yl)amino]benzonitrile Chemical compound ClC1=NC=NC(NC=2C=CC(=CC=2)C#N)=N1 CHKFMKBFNPZSAN-UHFFFAOYSA-N 0.000 description 1
SOPKWXMQSHLEKD-UHFFFAOYSA-N 4-[[4-(2,4,6-trimethylanilino)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC=NC(NC=2C=CC(=CC=2)C#N)=N1 SOPKWXMQSHLEKD-UHFFFAOYSA-N 0.000 description 1
QNDPLYPIHCKRQY-UHFFFAOYSA-N 4-[[4-(2,4,6-trimethylphenoxy)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1OC1=NC=NC(NC=2C=CC(=CC=2)C#N)=N1 QNDPLYPIHCKRQY-UHFFFAOYSA-N 0.000 description 1
MMENGDBZOHTAGQ-UHFFFAOYSA-N 4-[[4-(2,4,6-trimethylphenyl)sulfanyl-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1SC1=NC=NC(NC=2C=CC(=CC=2)C#N)=N1 MMENGDBZOHTAGQ-UHFFFAOYSA-N 0.000 description 1
DJBNTUXEUOSKDQ-UHFFFAOYSA-N 4-[[4-(2,6-dibromo-4-propan-2-ylanilino)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1NC1=NC=NC(NC=2C=CC(=CC=2)C#N)=N1 DJBNTUXEUOSKDQ-UHFFFAOYSA-N 0.000 description 1
LKZLTYJYIKHOJY-UHFFFAOYSA-N 4-[[4-(4-cyanoanilino)-1,3,5-triazin-2-yl]oxy]-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC=NC(NC=2C=CC(=CC=2)C#N)=N1 LKZLTYJYIKHOJY-UHFFFAOYSA-N 0.000 description 1
LJBPESRSYQLYPM-UHFFFAOYSA-N 4-[[4-(4-tert-butyl-2,6-dimethylanilino)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1NC1=NC=NC(NC=2C=CC(=CC=2)C#N)=N1 LJBPESRSYQLYPM-UHFFFAOYSA-N 0.000 description 1
YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
WFYGXOWFEIOHCZ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1O WFYGXOWFEIOHCZ-UHFFFAOYSA-N 0.000 description 1
CHHGWEBJQVWINZ-UHFFFAOYSA-N 4-tert-butyl-2,6-dimethylaniline Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1N CHHGWEBJQVWINZ-UHFFFAOYSA-N 0.000 description 1
ZNFFMCYSMBXZQU-NSHDSACASA-N 5-chloro-8-methyl-7-(3-methyl-but-2-enyl)-6,7,8,9-tetrahydro-2h-2,7,9a-triaza-benzo[cd]azulene-1-thione Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=C(Cl)C1=C32 ZNFFMCYSMBXZQU-NSHDSACASA-N 0.000 description 1
GMVPRGQOIOIIMI-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DODZYUBVSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
206010003591 Ataxia Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
210000004366 CD4-positive T-lymphocyte Anatomy 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
JDVVGAQPNNXQDW-WCMLQCRESA-N Castanospermine Natural products O[C@H]1[C@@H](O)[C@H]2[C@@H](O)CCN2C[C@H]1O JDVVGAQPNNXQDW-WCMLQCRESA-N 0.000 description 1
JDVVGAQPNNXQDW-TVNFTVLESA-N Castinospermine Chemical compound C1[C@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H](O)CCN21 JDVVGAQPNNXQDW-TVNFTVLESA-N 0.000 description 1
229920002101 Chitin Chemical class 0.000 description 1
208000016192 Demyelinating disease Diseases 0.000 description 1
206010012305 Demyelination Diseases 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
206010013887 Dysarthria Diseases 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
229920003148 Eudragit® E polymer Polymers 0.000 description 1
239000001116 FEMA 4028 Substances 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
241000282412 Homo Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 1
102100034343 Integrase Human genes 0.000 description 1
208000007766 Kaposi sarcoma Diseases 0.000 description 1
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
102000012404 Orosomucoid Human genes 0.000 description 1
108010061952 Orosomucoid Proteins 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
108010092799 RNA-directed DNA polymerase Proteins 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
241001061127 Thione Species 0.000 description 1
102400000160 Thymopentin Human genes 0.000 description 1
101800001703 Thymopentin Proteins 0.000 description 1
241000700605 Viruses Species 0.000 description 1
WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000004974 alkaline earth metal peroxides Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229920013820 alkyl cellulose Polymers 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
239000002259 anti human immunodeficiency virus agent Substances 0.000 description 1
229940124411 anti-hiv antiviral agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
235000011175 beta-cyclodextrine Nutrition 0.000 description 1
229960004853 betadex Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 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
239000011575 calcium Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
208000015114 central nervous system disease Diseases 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
208000004209 confusion Diseases 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000013068 control sample Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000000120 cytopathologic effect Effects 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
229960002086 dextran Drugs 0.000 description 1
229960000633 dextran sulfate Drugs 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
206010013395 disorientation Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000006260 foam Substances 0.000 description 1
229960000848 foscarnet sodium Drugs 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 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
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
238000004128 high performance liquid chromatography Methods 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
230000007124 immune defense Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
239000002955 immunomodulating agent Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229960001936 indinavir Drugs 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229960001627 lamivudine Drugs 0.000 description 1
JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
229960001614 levamisole Drugs 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000012803 melt mixture Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
WSKAQFVKUCCDLG-UHFFFAOYSA-N n-(4-chlorophenyl)-4-[1-[4-(2-methylpropyl)phenyl]ethyl]-1,3,5-triazin-2-amine Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C1=NC=NC(NC=2C=CC(Cl)=CC=2)=N1 WSKAQFVKUCCDLG-UHFFFAOYSA-N 0.000 description 1
239000002105 nanoparticle Substances 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
229960000689 nevirapine Drugs 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 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
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
239000002674 ointment Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229920001277 pectin Chemical class 0.000 description 1
239000001814 pectin Chemical class 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
229960004448 pentamidine Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
208000033808 peripheral neuropathy Diseases 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229940124531 pharmaceutical excipient 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
229920000233 poly(alkylene oxides) Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 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
238000002953 preparative HPLC Methods 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
WTTIBCHOELPGFK-LBPRGKRZSA-N r82150 Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=CC1=C32 WTTIBCHOELPGFK-LBPRGKRZSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
125000003375 sulfoxide group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
229960005314 suramin Drugs 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
206010043554 thrombocytopenia Diseases 0.000 description 1
PSWFFKRAVBDQEG-YGQNSOCVSA-N thymopentin Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 PSWFFKRAVBDQEG-YGQNSOCVSA-N 0.000 description 1
229960004517 thymopentin Drugs 0.000 description 1
ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229960000523 zalcitabine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- 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
- 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
- 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
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/70—Nanostructure
- Y10S977/773—Nanoparticle, i.e. structure having three dimensions of 100 nm or less
- Y10S977/775—Nanosized powder or flake, e.g. nanosized catalyst
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/915—Therapeutic or pharmaceutical composition

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

HR20010310A 1998-11-10 2001-05-02 2,4-disubstituted triazine derivatives HRP20010310A2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US10779998P	1998-11-10	1998-11-10
EP99203128		1999-09-24
PCT/EP1999/008688 WO2000027828A2 (en)	1998-11-10	1999-11-04	2,4-disubstituted triazine derivatives with anti hiv activity

Publications (1)

Publication Number	Publication Date
HRP20010310A2 true HRP20010310A2 (en)	2002-06-30

Family

ID=26153374

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20010310A HRP20010310A2 (en)	1998-11-10	2001-05-02	2,4-disubstituted triazine derivatives

Country Status (35)

Country	Link
US (2)	US6638932B1 (ru)
EP (1)	EP1129079B1 (ru)
JP (1)	JP2002529457A (ru)
KR (1)	KR100620402B1 (ru)
CN (1)	CN1207290C (ru)
AP (1)	AP1636A (ru)
AR (1)	AR021137A1 (ru)
AT (1)	ATE315031T1 (ru)
AU (1)	AU764472B2 (ru)
BG (1)	BG65160B1 (ru)
BR (1)	BR9915176A (ru)
CA (1)	CA2351203C (ru)
CY (1)	CY1105596T1 (ru)
CZ (1)	CZ20011532A3 (ru)
DE (1)	DE69929354T2 (ru)
DK (1)	DK1129079T3 (ru)
EA (1)	EA004501B1 (ru)
EE (1)	EE200100253A (ru)
ES (1)	ES2257081T3 (ru)
HK (1)	HK1038232A1 (ru)
HR (1)	HRP20010310A2 (ru)
HU (1)	HUP0104395A3 (ru)
ID (1)	ID28545A (ru)
IL (2)	IL143024A0 (ru)
MY (1)	MY126781A (ru)
NO (1)	NO319788B1 (ru)
NZ (1)	NZ510919A (ru)
OA (1)	OA11675A (ru)
PL (1)	PL196523B1 (ru)
PT (1)	PT1129079E (ru)
SI (1)	SI1129079T1 (ru)
SK (1)	SK6022001A3 (ru)
TR (1)	TR200101319T2 (ru)
TW (1)	TW541305B (ru)
WO (1)	WO2000027828A2 (ru)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6638932B1 (en) *	1998-11-10	2003-10-28	Janssen Pharmaceutica N.V.	2,4-disubstituted triazine derivatives
DE19945982A1 (de)	1999-09-24	2001-03-29	Knoll Ag	Geschwindigkeitsbestimmte Partikel
EP1282606B1 (en)	2000-05-08	2015-04-22	Janssen Pharmaceutica NV	Hiv replication inhibiting pyrimidines and triazines
AR039540A1 (es) *	2002-05-13	2005-02-23	Tibotec Pharm Ltd	Compuestos microbicidas con contenido de pirimidina o triazina
AU2004213173B2 (en) *	2003-02-07	2010-07-29	Janssen Pharmaceutica N.V.	HIV inhibiting 1,2,4-triazines
US7923554B2 (en)	2004-08-10	2011-04-12	Janssen Pharmaceutica N.V.	HIV inhibiting 1,2,4-triazin-6-one derivatives
GB201204756D0 (en) *	2012-03-19	2012-05-02	Lewi Paulus J	Triazines with suitable spacers for treatment and/or prevention of HIV infections

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4927592B1 (ru) *	1970-05-13	1974-07-18
BE754242A (fr) *	1970-07-15	1971-02-01	Geigy Ag J R	Diamino-s-triazines et dinitro-s-triazines
US4650867A (en) *	1985-03-26	1987-03-17	Ciba-Geigy Corporation	Process for the preparation of 2,4,6-tris(aminophenylamino)triazines
JPH02308248A (ja) *	1989-05-24	1990-12-21	Fuji Photo Film Co Ltd	アミノピリミジン系色素形成カプラーおよび該カプラーを含有するハロゲン化銀カラー写真感光材料
CA2174080A1 (en)	1993-10-12	1995-04-20	Paul Edward Aldrich	1n-alkyl-n-arylpyrimidinamines and derivatives thereof
US5691364A (en) *	1995-03-10	1997-11-25	Berlex Laboratories, Inc.	Benzamidine derivatives and their use as anti-coagulants
NO311614B1 (no) *	1996-10-01	2001-12-17	Janssen Pharmaceutica Nv	Substituerte diamino-1,3,5-triazinderivater
IL137922A0 (en) *	1998-02-17	2001-10-31	Tularik Inc	Anti-viral pyrimidine derivatives
US6638932B1 (en) *	1998-11-10	2003-10-28	Janssen Pharmaceutica N.V.	2,4-disubstituted triazine derivatives

1999
- 1999-11-04 US US09/831,808 patent/US6638932B1/en not_active Expired - Fee Related
- 1999-11-04 JP JP2000581008A patent/JP2002529457A/ja active Pending
- 1999-11-04 BR BR9915176-6A patent/BR9915176A/pt not_active IP Right Cessation
- 1999-11-04 DE DE69929354T patent/DE69929354T2/de not_active Expired - Fee Related
- 1999-11-04 HU HU0104395A patent/HUP0104395A3/hu unknown
- 1999-11-04 DK DK99953980T patent/DK1129079T3/da active
- 1999-11-04 PL PL348145A patent/PL196523B1/pl not_active IP Right Cessation
- 1999-11-04 WO PCT/EP1999/008688 patent/WO2000027828A2/en active IP Right Grant
- 1999-11-04 EE EEP200100253A patent/EE200100253A/xx unknown
- 1999-11-04 SI SI9930886T patent/SI1129079T1/sl unknown
- 1999-11-04 TR TR2001/01319T patent/TR200101319T2/xx unknown
- 1999-11-04 PT PT99953980T patent/PT1129079E/pt unknown
- 1999-11-04 AT AT99953980T patent/ATE315031T1/de not_active IP Right Cessation
- 1999-11-04 KR KR1020017003574A patent/KR100620402B1/ko not_active IP Right Cessation
- 1999-11-04 AP APAP/P/2001/002155A patent/AP1636A/en active
- 1999-11-04 IL IL14302499A patent/IL143024A0/xx active IP Right Grant
- 1999-11-04 AU AU10462/00A patent/AU764472B2/en not_active Ceased
- 1999-11-04 CZ CZ20011532A patent/CZ20011532A3/cs unknown
- 1999-11-04 SK SK602-2001A patent/SK6022001A3/sk unknown
- 1999-11-04 OA OA1200100114A patent/OA11675A/en unknown
- 1999-11-04 EP EP99953980A patent/EP1129079B1/en not_active Expired - Lifetime
- 1999-11-04 EA EA200100534A patent/EA004501B1/ru not_active IP Right Cessation
- 1999-11-04 CN CNB998130478A patent/CN1207290C/zh not_active Expired - Fee Related
- 1999-11-04 NZ NZ510919A patent/NZ510919A/en unknown
- 1999-11-04 ID IDW00200101017A patent/ID28545A/id unknown
- 1999-11-04 CA CA002351203A patent/CA2351203C/en not_active Expired - Fee Related
- 1999-11-04 ES ES99953980T patent/ES2257081T3/es not_active Expired - Lifetime
- 1999-11-05 MY MYPI99004801A patent/MY126781A/en unknown
- 1999-11-09 AR ARP990105681A patent/AR021137A1/es active IP Right Grant
- 1999-12-23 TW TW088119615A patent/TW541305B/zh not_active IP Right Cessation
2001
- 2001-04-06 BG BG105419A patent/BG65160B1/bg unknown
- 2001-04-19 NO NO20011934A patent/NO319788B1/no unknown
- 2001-05-02 HR HR20010310A patent/HRP20010310A2/hr not_active Application Discontinuation
- 2001-05-07 IL IL143024A patent/IL143024A/en not_active IP Right Cessation
- 2001-12-10 HK HK01108632A patent/HK1038232A1/xx not_active IP Right Cessation
2003
- 2003-08-27 US US10/649,017 patent/US7015221B2/en not_active Expired - Fee Related
2006
- 2006-03-31 CY CY20061100457T patent/CY1105596T1/el unknown

Also Published As

Publication number	Publication date
SI1129079T1 (sl)	2006-06-30
EA004501B1 (ru)	2004-04-29
AP1636A (en)	2006-07-17
ATE315031T1 (de)	2006-02-15
WO2000027828A2 (en)	2000-05-18
DK1129079T3 (da)	2006-05-15
BG105419A (en)	2001-11-30
TR200101319T2 (tr)	2001-10-22
EA200100534A1 (ru)	2001-10-22
HUP0104395A3 (en)	2003-02-28
CA2351203C (en)	2009-03-24
EP1129079A2 (en)	2001-09-05
AU764472B2 (en)	2003-08-21
TW541305B (en)	2003-07-11
WO2000027828A3 (en)	2000-09-21
PL348145A1 (en)	2002-05-06
CN1207290C (zh)	2005-06-22
BR9915176A (pt)	2001-08-14
HUP0104395A2 (hu)	2002-04-29
EE200100253A (et)	2002-12-16
KR20010075234A (ko)	2001-08-09
DE69929354T2 (de)	2006-09-14
US6638932B1 (en)	2003-10-28
ID28545A (id)	2001-05-31
SK6022001A3 (en)	2002-01-07
ES2257081T3 (es)	2006-07-16
OA11675A (en)	2005-01-12
US20050277641A1 (en)	2005-12-15
US7015221B2 (en)	2006-03-21
BG65160B1 (bg)	2007-04-30
NO319788B1 (no)	2005-09-12
KR100620402B1 (ko)	2006-09-13
NO20011934D0 (no)	2001-04-19
MY126781A (en)	2006-10-31
HK1038232A1 (en)	2002-03-08
NZ510919A (en)	2003-11-28
CA2351203A1 (en)	2000-05-18
JP2002529457A (ja)	2002-09-10
AU1046200A (en)	2000-05-29
CN1325387A (zh)	2001-12-05
CZ20011532A3 (cs)	2001-10-17
NO20011934L (no)	2001-04-19
IL143024A0 (en)	2002-04-21
IL143024A (en)	2006-06-11
DE69929354D1 (de)	2006-03-30
CY1105596T1 (el)	2010-07-28
EP1129079B1 (en)	2006-01-04
PL196523B1 (pl)	2008-01-31
PT1129079E (pt)	2006-05-31
AR021137A1 (es)	2002-06-12

Legal Events

Date	Code	Title	Description
2002-06-30	A1OB	Publication of a patent application
2002-12-11	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2006-10-19	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20061019 Year of fee payment: 8
2008-11-21	OBST	Application withdrawn

Publication	Publication Date	Title
JP5230050B2 (ja)	2013-07-10	Ｈｉｖ複製阻害剤
JP3635238B2 (ja)	2005-04-06	Ｈｉｖの複製を阻害するピリミジン類
CN104271133B (zh)	2017-10-13	1H‑吡唑并[3,4‑b]吡啶及其治疗应用
EP1597242B1 (en)	2008-07-23	Hiv inhibiting 1,2,4-triazines
DE60117839T2 (de)	2006-11-23	Pyridinon und pyridinethion-derivate mit hiv-hemmenden eigenschaften
DE60221368T2 (de)	2008-04-17	Hiv hemmende pyrazinon-derivate
HRP20010310A2 (en)	2002-06-30	2,4-disubstituted triazine derivatives
MXPA01003644A (en)	2002-06-05	2,4-disubstituted triazine derivatives
ZA200103768B (en)	2002-06-10	2,4-Disubstituted triazine derivatives.
MXPA01003646A (en)	2001-12-04	Hiv replication inhibiting pyrimidines