NO333358B1 - Partikkel bestaende av en fast dispersjon - Google Patents

Partikkel bestaende av en fast dispersjon Download PDF

Info

Publication number: NO333358B1
Authority: NO; Norway
Prior art keywords: amino; benzonitrile; pyrimidinyl; formula; cyano
Prior art date: 1999-09-24

Application number

NO20021443A

Other languages

English (en)

Norwegian (no)

Other versions

NO20021443D0 (no

NO20021443L (no

Inventor

Lieven Elvire Colette Baert

Geert Verreck

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.)

1999-09-24

Filing date

2002-03-22

Publication date

2013-05-13

2002-03-22 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2002-03-22 Publication of NO20021443D0 publication Critical patent/NO20021443D0/no

2002-03-22 Publication of NO20021443L publication Critical patent/NO20021443L/no

2013-05-13 Publication of NO333358B1 publication Critical patent/NO333358B1/no

Links

239000002245 particle Substances 0.000 title claims abstract description 104
239000007962 solid dispersion Substances 0.000 title claims description 24
150000001875 compounds Chemical class 0.000 claims abstract description 230
239000000203 mixture Substances 0.000 claims abstract description 127
229920003169 water-soluble polymer Polymers 0.000 claims abstract description 34
241000124008 Mammalia Species 0.000 claims abstract description 15
208000036142 Viral infection Diseases 0.000 claims abstract description 9
230000009385 viral infection Effects 0.000 claims abstract description 9
-1 cyano, amino, imino, aminocarbonyl Chemical group 0.000 claims description 227
239000000460 chlorine Substances 0.000 claims description 96
125000000217 alkyl group Chemical group 0.000 claims description 71
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
125000001424 substituent group Chemical group 0.000 claims description 62
125000005843 halogen group Chemical group 0.000 claims description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
239000000243 solution Substances 0.000 claims description 55
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 46
239000002552 dosage form Substances 0.000 claims description 45
125000004093 cyano group Chemical group *C#N 0.000 claims description 43
125000003118 aryl group Chemical group 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 38
229910052739 hydrogen Inorganic materials 0.000 claims description 38
150000003839 salts Chemical class 0.000 claims description 37
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 32
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 32
125000003545 alkoxy group Chemical group 0.000 claims description 30
150000003254 radicals Chemical class 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 24
125000000714 pyrimidinyl group Chemical group 0.000 claims description 24
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 21
229910052801 chlorine Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical group NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 claims description 17
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 16
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 15
150000001412 amines Chemical group 0.000 claims description 15
125000001041 indolyl group Chemical group 0.000 claims description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
239000006104 solid solution Substances 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 14
125000003373 pyrazinyl group Chemical group 0.000 claims description 14
125000002098 pyridazinyl group Chemical group 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
229920002678 cellulose Polymers 0.000 claims description 12
125000002757 morpholinyl group Chemical group 0.000 claims description 12
125000003386 piperidinyl group Chemical group 0.000 claims description 12
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
229920000642 polymer Polymers 0.000 claims description 11
125000001931 aliphatic group Chemical group 0.000 claims description 10
235000010980 cellulose Nutrition 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
239000004014 plasticizer Substances 0.000 claims description 9
239000011734 sodium Substances 0.000 claims description 9
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 8
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
239000006185 dispersion Substances 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
125000004953 trihalomethyl group Chemical group 0.000 claims description 8
ILAYIAGXTHKHNT-UHFFFAOYSA-N 4-[4-(2,4,6-trimethyl-phenylamino)-pyrimidin-2-ylamino]-benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 ILAYIAGXTHKHNT-UHFFFAOYSA-N 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
150000001204 N-oxides Chemical class 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
239000007888 film coating Substances 0.000 claims description 7
238000009501 film coating Methods 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 7
125000000168 pyrrolyl group Chemical group 0.000 claims description 7
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
239000001913 cellulose Substances 0.000 claims description 6
PYGWGZALEOIKDF-UHFFFAOYSA-N etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
239000012729 immediate-release (IR) formulation Substances 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
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 claims description 5
BKXUZQUTEZBQIW-UHFFFAOYSA-N 4-[[4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzamide Chemical compound CC1=CC(C)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C(N)=O)=N1 BKXUZQUTEZBQIW-UHFFFAOYSA-N 0.000 claims description 5
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 5
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
229920003148 Eudragit® E polymer Polymers 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
229920013820 alkyl cellulose Polymers 0.000 claims description 5
125000001118 alkylidene group Chemical group 0.000 claims description 5
NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical group COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 0.000 claims description 5
239000002775 capsule Substances 0.000 claims description 5
229920001577 copolymer Polymers 0.000 claims description 5
239000007884 disintegrant Substances 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
238000001704 evaporation Methods 0.000 claims description 5
229920001451 polypropylene glycol Polymers 0.000 claims description 5
238000007873 sieving Methods 0.000 claims description 5
GNELAKVSOPMFKN-UHFFFAOYSA-N 4-[5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1Br GNELAKVSOPMFKN-UHFFFAOYSA-N 0.000 claims description 4
UMLZEJREMDUKPX-UHFFFAOYSA-N 4-[[4-amino-6-(2,4,6-trimethylanilino)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC(N)=NC(NC=2C=CC(=CC=2)C#N)=N1 UMLZEJREMDUKPX-UHFFFAOYSA-N 0.000 claims description 4
OJJVULINVLFCDX-UHFFFAOYSA-N 4-[[4-amino-6-[(2,6-dichlorophenyl)methyl]pyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(NC=2C=CC(=CC=2)C#N)=NC(N)=CC=1CC1=C(Cl)C=CC=C1Cl OJJVULINVLFCDX-UHFFFAOYSA-N 0.000 claims description 4
VKQKEROEGYSHIY-UHFFFAOYSA-N 4-[[5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]amino]-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1Br VKQKEROEGYSHIY-UHFFFAOYSA-N 0.000 claims description 4
SOJXDRPTMGPTRD-UHFFFAOYSA-N 4-[[5-chloro-4-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1Cl SOJXDRPTMGPTRD-UHFFFAOYSA-N 0.000 claims description 4
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
239000001768 carboxy methyl cellulose Substances 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
238000000227 grinding Methods 0.000 claims description 4
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
239000000049 pigment Substances 0.000 claims description 4
238000001694 spray drying Methods 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
GQMQZXHAMCLBEK-UHFFFAOYSA-N 4-[2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 GQMQZXHAMCLBEK-UHFFFAOYSA-N 0.000 claims description 3
WPNAIKSJHKWRNV-UHFFFAOYSA-N 4-[6-amino-5-chloro-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Cl WPNAIKSJHKWRNV-UHFFFAOYSA-N 0.000 claims description 3
YALKQTNPKCPCSL-UHFFFAOYSA-N 4-[[2-(4-cyanoanilino)-5-methylpyrimidin-4-yl]amino]-3,5-dimethylbenzonitrile Chemical compound N1=C(NC=2C(=CC(=CC=2C)C#N)C)C(C)=CN=C1NC1=CC=C(C#N)C=C1 YALKQTNPKCPCSL-UHFFFAOYSA-N 0.000 claims description 3
FOAAECKTFHPTHX-UHFFFAOYSA-N 4-[[4-(2,4,6-trimethylphenoxy)pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1OC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 FOAAECKTFHPTHX-UHFFFAOYSA-N 0.000 claims description 3
LQUFNJQYHORALJ-UHFFFAOYSA-N 4-[[4-[(2,6-dichlorophenyl)methyl]-6-(2-pyrrolidin-1-ylethylamino)pyrimidin-2-yl]amino]benzonitrile Chemical compound ClC1=CC=CC(Cl)=C1CC1=CC(NCCN2CCCC2)=NC(NC=2C=CC(=CC=2)C#N)=N1 LQUFNJQYHORALJ-UHFFFAOYSA-N 0.000 claims description 3
SWUCAIPJSDZLTL-UHFFFAOYSA-N 4-[[4-[(2,6-dichlorophenyl)methyl]-6-(3-hydroxypropylamino)pyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(NC=2C=CC(=CC=2)C#N)=NC(NCCCO)=CC=1CC1=C(Cl)C=CC=C1Cl SWUCAIPJSDZLTL-UHFFFAOYSA-N 0.000 claims description 3
UXIAXNIFQFODAB-UHFFFAOYSA-N 4-[[4-[(5-acetyl-7-methyl-2,3-dihydro-1h-inden-4-yl)oxy]-6-amino-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC(=O)C1=CC(C)=C2CCCC2=C1OC(N=1)=NC(N)=NC=1NC1=CC=C(C#N)C=C1 UXIAXNIFQFODAB-UHFFFAOYSA-N 0.000 claims description 3
GZHZZSSHNAJANR-UHFFFAOYSA-N 4-[[4-[2,6-dichloro-4-(trifluoromethyl)anilino]pyrimidin-2-yl]amino]benzonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 GZHZZSSHNAJANR-UHFFFAOYSA-N 0.000 claims description 3
SWJAAIMAEBSKQZ-UHFFFAOYSA-N 4-[[4-amino-5-chloro-6-(2,4,6-trimethylanilino)pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Cl SWJAAIMAEBSKQZ-UHFFFAOYSA-N 0.000 claims description 3
NIUSPLDPGYTQOP-UHFFFAOYSA-N 4-[[4-amino-6-(2,6-dibromo-4-methylanilino)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound BrC1=CC(C)=CC(Br)=C1NC1=NC(N)=NC(NC=2C=CC(=CC=2)C#N)=N1 NIUSPLDPGYTQOP-UHFFFAOYSA-N 0.000 claims description 3
YZFONMVHHPTCCK-UHFFFAOYSA-N 4-[[4-amino-6-(n,2,4,6-tetramethylanilino)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC=1C=C(C)C=C(C)C=1N(C)C(N=1)=NC(N)=NC=1NC1=CC=C(C#N)C=C1 YZFONMVHHPTCCK-UHFFFAOYSA-N 0.000 claims description 3
UDVWMOGBYZKGPC-UHFFFAOYSA-N 4-[[6-amino-5-chloro-2-(4-cyanoanilino)pyrimidin-4-yl]amino]-3,5-dimethylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Cl UDVWMOGBYZKGPC-UHFFFAOYSA-N 0.000 claims description 3
229920002785 Croscarmellose sodium Polymers 0.000 claims description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 3
229920000168 Microcrystalline cellulose Polymers 0.000 claims description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
229920002472 Starch Polymers 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 3
239000001863 hydroxypropyl cellulose Substances 0.000 claims description 3
235000019813 microcrystalline cellulose Nutrition 0.000 claims description 3
239000008108 microcrystalline cellulose Substances 0.000 claims description 3
229940016286 microcrystalline cellulose Drugs 0.000 claims description 3
239000001814 pectin Substances 0.000 claims description 3
235000010987 pectin Nutrition 0.000 claims description 3
229920001277 pectin Polymers 0.000 claims description 3
235000019698 starch Nutrition 0.000 claims description 3
HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 2
DKUXLRIATNRYPU-UHFFFAOYSA-N 3,5-dichloro-4-[[2-(4-cyanoanilino)pyrimidin-4-yl]amino]benzonitrile Chemical compound ClC1=CC(C#N)=CC(Cl)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 DKUXLRIATNRYPU-UHFFFAOYSA-N 0.000 claims description 2
XOPGEBSETGNEJL-UHFFFAOYSA-N 4-[[2-(2,4,6-trimethylanilino)pyrimidin-4-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=NC=CC(NC=2C=CC(=CC=2)C#N)=N1 XOPGEBSETGNEJL-UHFFFAOYSA-N 0.000 claims description 2
HVPZCARYDAKDCH-UHFFFAOYSA-N 4-[[2-amino-6-(2,4,6-trimethylanilino)pyrimidin-4-yl]amino]benzonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=CC(NC=2C=CC(=CC=2)C#N)=NC(N)=N1 HVPZCARYDAKDCH-UHFFFAOYSA-N 0.000 claims description 2
SAVRWVQKFRBTBF-UHFFFAOYSA-N 4-[[2-amino-6-(2,6-dichlorophenoxy)pyrimidin-4-yl]amino]benzonitrile Chemical compound C=1C(OC=2C(=CC=CC=2Cl)Cl)=NC(N)=NC=1NC1=CC=C(C#N)C=C1 SAVRWVQKFRBTBF-UHFFFAOYSA-N 0.000 claims description 2
FUSXPBPIAGTAMR-UHFFFAOYSA-N 4-[[4-(2,4,6-trichloroanilino)pyrimidin-2-yl]amino]benzonitrile Chemical compound ClC1=CC(Cl)=CC(Cl)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 FUSXPBPIAGTAMR-UHFFFAOYSA-N 0.000 claims description 2
GNDYJAJPUZTPCW-UHFFFAOYSA-N 4-[[4-(2,4-dibromo-3,6-dichloroanilino)pyrimidin-2-yl]amino]benzonitrile Chemical compound ClC1=CC(Br)=C(Cl)C(Br)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 GNDYJAJPUZTPCW-UHFFFAOYSA-N 0.000 claims description 2
WLOFPRRWQFNHBX-UHFFFAOYSA-N 4-[[4-(2,4-dichloro-6-methylanilino)pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(Cl)=CC(Cl)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 WLOFPRRWQFNHBX-UHFFFAOYSA-N 0.000 claims description 2
UAMROCZGVWMDQT-UHFFFAOYSA-N 4-[[4-(2,6-dibromo-4-propan-2-ylanilino)-5-methylpyrimidin-2-yl]amino]benzonitrile Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1C UAMROCZGVWMDQT-UHFFFAOYSA-N 0.000 claims description 2
ZZCZJGBEYAACSA-UHFFFAOYSA-N 4-[[4-(2,6-dibromo-4-propan-2-ylanilino)pyrimidin-2-yl]amino]benzonitrile Chemical compound BrC1=CC(C(C)C)=CC(Br)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 ZZCZJGBEYAACSA-UHFFFAOYSA-N 0.000 claims description 2
VTRDOEBYNRKPFH-UHFFFAOYSA-N 4-[[4-(2,6-dibromo-4-propylanilino)-5-methylpyrimidin-2-yl]amino]benzonitrile Chemical compound BrC1=CC(CCC)=CC(Br)=C1NC1=NC(NC=2C=CC(=CC=2)C#N)=NC=C1C VTRDOEBYNRKPFH-UHFFFAOYSA-N 0.000 claims description 2
RCBOAAIFNPVBKP-UHFFFAOYSA-N 4-[[4-(2,6-dichlorophenyl)sulfanylpyrimidin-2-yl]amino]benzonitrile Chemical compound ClC1=CC=CC(Cl)=C1SC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 RCBOAAIFNPVBKP-UHFFFAOYSA-N 0.000 claims description 2
QIUVMMIRTAYVRC-UHFFFAOYSA-N 4-[[4-(2-bromo-4-chloro-6-methylphenoxy)pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(Cl)=CC(Br)=C1OC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 QIUVMMIRTAYVRC-UHFFFAOYSA-N 0.000 claims description 2
UFZSEYMEFYPRRY-UHFFFAOYSA-N 4-[[4-(2-cyanoethylamino)-6-[(2,6-dichlorophenyl)methyl]pyrimidin-2-yl]amino]benzonitrile Chemical compound ClC1=CC=CC(Cl)=C1CC1=CC(NCCC#N)=NC(NC=2C=CC(=CC=2)C#N)=N1 UFZSEYMEFYPRRY-UHFFFAOYSA-N 0.000 claims description 2
NAHFVGNZSYSRML-UHFFFAOYSA-N 4-[[4-(4-acetyl-2,6-dimethylphenoxy)-6-amino-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C(=O)C)=CC(C)=C1OC1=NC(N)=NC(NC=2C=CC(=CC=2)C#N)=N1 NAHFVGNZSYSRML-UHFFFAOYSA-N 0.000 claims description 2
BMCJDMQCNMPDEX-UHFFFAOYSA-N 4-[[4-(4-bromo-2,6-dimethylanilino)-5-methylpyrimidin-2-yl]amino]benzonitrile Chemical compound N1=C(NC=2C(=CC(Br)=CC=2C)C)C(C)=CN=C1NC1=CC=C(C#N)C=C1 BMCJDMQCNMPDEX-UHFFFAOYSA-N 0.000 claims description 2
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Classifications

- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
- 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
- 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
- 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

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NO20021443A 1999-09-24 2002-03-22 Partikkel bestaende av en fast dispersjon NO333358B1 (no)

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Families Citing this family (113)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE396978T1 (de)	1999-10-07	2008-06-15	Amgen Inc	Triazin-kinase-hemmer
DE60028754T2 (de)	1999-11-12	2007-05-31	Abbott Laboratories, Abbott Park	Feste dispersion mit ritonavir, fenofibrat oder griseofulvin
US7364752B1 (en)	1999-11-12	2008-04-29	Abbott Laboratories	Solid dispersion pharamaceutical formulations
JP2003532635A (ja)	2000-02-17	2003-11-05	アムジエン・インコーポレーテツド	キナーゼ阻害薬
DE10026698A1 (de)	2000-05-30	2001-12-06	Basf Ag	Selbstemulgierende Wirkstoffformulierung und Verwendung dieser Formulierung
US6861426B2 (en)	2001-02-27	2005-03-01	Teva Pharmaceutical Industries Ltd.	Crystal forms of lamotrigine and processes for their preparations
JP2004534812A (ja)	2001-06-22	2004-11-18	ファイザー・プロダクツ・インク	薬物および中性ポリマーの分散物の医薬組成物
US8101629B2 (en)	2001-08-13	2012-01-24	Janssen Pharmaceutica N.V.	Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile
JO3429B1 (ar)	2001-08-13	2019-10-20	Janssen Pharmaceutica Nv	مشتقات برميدينات مثبطة فيروس الايدز
US7638522B2 (en)	2001-08-13	2009-12-29	Janssen Pharmaceutica N.V.	Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino] benzonitrile
US6939874B2 (en)	2001-08-22	2005-09-06	Amgen Inc.	Substituted pyrimidinyl derivatives and methods of use
US7115617B2 (en)	2001-08-22	2006-10-03	Amgen Inc.	Amino-substituted pyrimidinyl derivatives and methods of use
JP4460292B2 (ja)	2001-10-17	2010-05-12	ベーリンガーインゲルハイムファルマゲゼルシャフトミットベシュレンクテルハフツングウントコンパニーコマンディトゲゼルシャフト	ピリミジン誘導体、これらの化合物を含む医薬組成物、その使用及びその調製方法
SE0104140D0 (sv) *	2001-12-07	2001-12-07	Astrazeneca Ab	Novel Compounds
TWI329105B (en)	2002-02-01	2010-08-21	Rigel Pharmaceuticals Inc	2,4-pyrimidinediamine compounds and their uses
PT1479397E (pt)	2002-02-05	2011-09-01	Astellas Pharma Inc	Derivados de 2,4,6-triamino-1,3,5-triazina
ATE357217T1 (de) *	2002-04-23	2007-04-15	Teva Pharma	Pharmazeutische zusammensetzung enthaltend lamotrigine-partikel mit definierter morphologie
AR039540A1 (es)	2002-05-13	2005-02-23	Tibotec Pharm Ltd	Compuestos microbicidas con contenido de pirimidina o triazina
US7015227B2 (en)	2002-06-21	2006-03-21	Cgi Pharmaceuticals, Inc.	Certain amino-substituted monocycles as kinase modulators
RS51752B (en)	2002-07-29	2011-12-31	Rigel Pharmaceuticals	METHODS OF TREATMENT AND PREVENTION OF AUTOIMMUNE DISEASES WITH 2,4-PYRIMIDINDIAMINE COMPOUNDS
PT1529032E (pt)	2002-08-09	2013-07-11	Janssen Pharmaceutica Nv	Processos para a preparação de 4-[[(4-[[4-(2-cianoetenilo)-2,6 dimetilofenilo]amino]-2-pirimidinilo]amino]benzonitrilo
SI1551372T1 (en) *	2002-09-20	2018-08-31	Alpharma Pharmaceuticals Llc	SUBVENCATION DATA AND RELATED CONSTRUCTIONS AND PROCEDURES
US7504410B2 (en) *	2002-11-28	2009-03-17	Schering Aktiengesellschaft	Chk-, Pdk- and Akt-inhibitory pyrimidines, their production and use as pharmaceutical agents
AU2002350719A1 (en) *	2002-11-29	2004-06-23	Janssen Pharmaceutica N.V.	Pharmaceutical compositions comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base
AU2004205642C1 (en)	2003-01-14	2012-01-12	Arena Pharmaceuticals, Inc.	1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
MXPA05008364A (es)	2003-02-07	2005-11-04	Janssen Pharmaceutica Nv	Derivados de pirimidina para la prevencion de una infeccion por vih.
CL2004000303A1 (es) *	2003-02-20	2005-04-08	Tibotec Pharm Ltd	Compuestos derivados de pirimidinas y triazinas; proceso de preparacion; composicion farmaceutica; y su uso para inhibir la replicacion del vih.
AR045047A1 (es)	2003-07-11	2005-10-12	Arena Pharm Inc	Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
US20060172010A1 (en)	2003-07-17	2006-08-03	Gael Lamoureux	Process for preparing particles containing an antiviral
PT1656372E (pt)	2003-07-30	2013-06-27	Rigel Pharmaceuticals Inc	Métodos para o tratamento ou prevenção de doenças autoimunes com compostos de 2,4-pirimidinadiamina
US8025899B2 (en)	2003-08-28	2011-09-27	Abbott Laboratories	Solid pharmaceutical dosage form
WO2005040159A1 (en)	2003-10-17	2005-05-06	Astrazeneca Ab	4-(pyrazol-3-ylamino) pyrimidine derivatives for use in the treatment of cancer
EP2343282B1 (en)	2004-03-05	2015-07-22	F. Hoffmann-La Roche AG	Diaminopyrimidines as P2X3 and P2X2/3 antagonists
MX2007003325A (es)	2004-09-20	2007-06-05	Xenon Pharmaceuticals Inc	Derivados heterociclicos y su uso como inhibidores estearoil-coa-desaturasa.
MX2007003319A (es)	2004-09-20	2007-06-05	Xenon Pharmaceuticals Inc	Derivados heterociclicos y su uso como agentes terapeuticos.
TW200626572A (en)	2004-09-20	2006-08-01	Xenon Pharmaceuticals Inc	Heterocyclic derivatives and their use as therapeutic agents
EP1799664A1 (en)	2004-09-20	2007-06-27	Xenon Pharmaceuticals Inc.	Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors
TW200626139A (en)	2004-09-20	2006-08-01	Xenon Pharmaceuticals Inc	Heterocyclic derivatives and their use as therapeutic agents
TW200626138A (en)	2004-09-20	2006-08-01	Xenon Pharmaceuticals Inc	Heterocyclic derivatives and their use as therapeutic agents
CN101083982A (zh)	2004-09-20	2007-12-05	泽农医药公司	用于治疗硬脂酰CoA去饱和酶介导的疾病的杂环衍生物
ATE540035T1 (de)	2004-11-24	2012-01-15	Rigel Pharmaceuticals Inc	Spiro-2,4-pyrimidindiamin-verbindungen und ihre verwendungen
EP1856135B1 (en)	2005-01-19	2009-12-09	Rigel Pharmaceuticals, Inc.	Prodrugs of 2,4-pyrimidinediamine compounds and their uses
NZ561525A (en)	2005-02-16	2010-11-26	Astrazeneca Ab	Benzimidazole compounds and analogues, containing a pyrazole ring, for inhibition of Trk activity, affecting cancer
EP1853567B1 (en) *	2005-02-18	2014-12-31	Janssen R&D Ireland	Hiv inhibiting 2-(4-cyanophenylamino) pyrimidine oxide derivatives
ME01229B (me) *	2005-03-04	2013-06-20	Janssen R& D Ireland	2-(4-cijanofenil)-6-hidroksilaminopirimidini koji inhibiraju hiv
TW200710091A (en)	2005-04-11	2007-03-16	Tibotec Pharm Ltd	(1,10B-dihydro-2-(aminoalkyl-phenyl)-5H-pyrazolo [1,5-c][1,3]benzoxazin-5-yl)phenyl methanone derivatives as HIV viral replication inhibitors
JP2008540622A (ja)	2005-05-16	2008-11-20	アストラゼネカアクチボラグ	化合物
WO2006125809A1 (en)	2005-05-26	2006-11-30	Tibotec Pharmaceuticals Ltd	Process for preparing 4-[(1,6-dihydro-6-oxo-2-pyrimidinyl)amino benzonitrile
MX2007015216A (es)	2005-06-03	2008-02-22	Xenon Pharmaceuticals Inc	Derivados de aminotiazol y sus usos como agentes terapeuticos.
MX2008002731A (es)	2005-09-01	2008-03-26	Hoffmann La Roche	Diaminopirimidinas como moduladores de p2x3 y p3x2/3.
EP1924564B1 (en)	2005-09-01	2016-11-09	F.Hoffmann-La Roche Ag	Diaminopyrimidines as p2x3 and p2x2/3 modulators
CA2620129C (en)	2005-09-01	2014-12-23	F. Hoffmann-La Roche Ag	Diaminopyrimidines as p2x3 and p2x2/3 modulators
WO2007049041A1 (en)	2005-10-28	2007-05-03	Astrazeneca Ab	4- (3-aminopyrazole) pyrimidine derivatives for use as tyrosine kinase inhibitors in the treatment of cancer
CN101299993A (zh) *	2005-11-04	2008-11-05	伊士曼化工公司	用于给药难溶的药学活性剂的羧烷基纤维素酯
AU2007255418C1 (en) *	2006-06-06	2011-08-18	Janssen Sciences Ireland Uc	Process for preparing spray dried formulations of TMC125
PL2719378T3 (pl)	2006-06-19	2017-02-28	Alpharma Pharmaceuticals Llc	Kompozycje farmaceutyczne
AU2007322269A1 (en) *	2006-10-11	2008-05-29	Alpharma Pharmaceuticals, Llc	Pharmaceutical compositions
EP2104491B1 (en)	2006-12-06	2017-02-22	Janssen Sciences Ireland UC	Hydrobromide salt of an anti-hiv compound
TWI494133B (zh) *	2007-03-14	2015-08-01	Tibotec Pharm Ltd	重組用粉末
UA99459C2 (en)	2007-05-04	2012-08-27	Астразенека Аб	9-(pyrazol-3-yl)- 9h-purine-2-amine and 3-(pyraz0l-3-yl)-3h-imidazo[4,5-b]pyridin-5-amine derivatives and their use for the treatment of cancer
AU2008262031B2 (en) *	2007-06-08	2011-08-25	Boehringer Ingelheim International Gmbh	Extended release formulation of nevirapine
CA2689330A1 (en) *	2007-06-25	2008-12-31	Tibotec Pharmaceuticals	Combination formulations
EP2212298B1 (en)	2007-10-18	2013-03-27	Concert Pharmaceuticals Inc.	Deuterated etravirine
EP2214486A4 (en) *	2007-10-19	2011-03-09	Avila Therapeutics Inc	HETEROARYL COMPOUNDS AND ITS USES
US7989465B2 (en) *	2007-10-19	2011-08-02	Avila Therapeutics, Inc.	4,6-disubstituted pyrimidines useful as kinase inhibitors
CA2709905A1 (en) *	2007-12-17	2009-06-25	Alfred Liang	Abuse-resistant oxycodone composition
US8623418B2 (en)	2007-12-17	2014-01-07	Alpharma Pharmaceuticals Llc	Pharmaceutical composition
AR072939A1 (es) *	2008-08-20	2010-09-29	Schering Corp	Derivados de piridina y pirimidina sustituidas con etenilo y su uso en el tratamiento de infecciones virales
CA2734487A1 (en) *	2008-08-20	2010-02-25	Southern Research Institute	Ethynyl-substituted pyridine and pyrimidine derivatives and their use in treating viral infections
WO2010033226A1 (en) *	2008-09-17	2010-03-25	Nektar Therapeutics	Oligomer-protease inhibitor conjugates
CN101744823B (zh) *	2008-12-17	2013-06-19	广东东阳光药业有限公司	一种二氢嘧啶类化合物的固体分散体及其药用制剂
CA2757228C (en)	2009-03-30	2018-01-02	Tibotec Pharmaceuticals	Co-crystal of etravirine and nicotinamide
US20130023497A1 (en) *	2009-06-08	2013-01-24	Chunlin Tao	Triazine Derivatives and their Therapeutical Applications
US20110196156A1 (en) *	2009-06-22	2011-08-11	Mukund Keshav Gurjar	Process for synthesis of diarylpyrimidine non-nucleoside reverse transcriptase inhibitor
KR101531448B1 (ko)	2010-06-04	2015-06-24	에프. 호프만-라 로슈 아게	Lrrk2 조절제로서의 아미노피리미딘 유도체
MX2013003184A (es)	2010-09-22	2013-06-07	Arena Pharm Inc	Moduladores del receptor gpr119 y el tratamiento de transtornos relacionados con el mismo.
AU2011328139A1 (en)	2010-11-10	2013-04-04	F. Hoffmann-La Roche Ag	Pyrazole aminopyrimidine derivatives as LRRK2 modulators
US8754114B2 (en)	2010-12-22	2014-06-17	Incyte Corporation	Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3
CN104364268B (zh) *	2012-04-11	2016-07-20	陶氏环球技术有限责任公司	包含纤维素醚的熔融挤出的组合物
EP2836235B1 (en) *	2012-04-11	2017-03-08	Dow Global Technologies LLC	Novel sustained release dosage forms
US9757465B2 (en) *	2012-04-11	2017-09-12	Dow Global Technologies Llc	Composition comprising an organic diluent and a cellulose ether
DK2861595T5 (en)	2012-06-13	2018-01-15	Incyte Holdings Corp	Substituted tricyclic compounds as FGFR inhibitors
ES2664094T3 (es) *	2012-07-12	2018-04-18	Hetero Research Foundation	Procedimiento de preparación de rilpivirina utilizando un intermedio nuevo
WO2014026125A1 (en)	2012-08-10	2014-02-13	Incyte Corporation	Pyrazine derivatives as fgfr inhibitors
US9266892B2 (en)	2012-12-19	2016-02-23	Incyte Holdings Corporation	Fused pyrazoles as FGFR inhibitors
MY181497A (en)	2013-04-19	2020-12-23	Incyte Holdings Corp	Bicyclic heterocycles as fgfr inhibitors
US10851105B2 (en)	2014-10-22	2020-12-01	Incyte Corporation	Bicyclic heterocycles as FGFR4 inhibitors
SI3242666T1 (sl)	2015-01-06	2025-03-31	Arena Pharmaceuticals, Inc.	Spojina za uporabo pri zdravljenju stanj, povezanih z receptorjem s1p1
AU2016219822B2 (en)	2015-02-20	2020-07-09	Incyte Holdings Corporation	Bicyclic heterocycles as FGFR inhibitors
US9580423B2 (en)	2015-02-20	2017-02-28	Incyte Corporation	Bicyclic heterocycles as FGFR4 inhibitors
MA41551A (fr)	2015-02-20	2017-12-26	Incyte Corp	Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4
AR100459A1 (es) *	2015-05-15	2016-10-05	Química Luar S R L	Una composición farmacéutica antiviral de uso tópico
KR102603199B1 (ko)	2015-06-22	2023-11-16	아레나 파마슈티칼스, 인크.	Ｓ1ｐ1 수용체-관련 장애에서의 사용을 위한 (ｒ)-2-(7-(4-시클로펜틸-3-(트리플루오로메틸)벤질옥시)-1,2,3,4-테트라히드로시클로-펜타[ｂ]인돌-3-일)아세트산 (화합물 1)의 결정성 ｌ-아르기닌 염
CN110520124A (zh)	2017-02-16	2019-11-29	艾尼纳制药公司	用于治疗原发性胆汁性胆管炎的化合物和方法
US10172856B2 (en)	2017-04-06	2019-01-08	Janssen Pharmaceutica Nv	2,4-diaminopyrimidine derivatives as histamine H4 modulators
AR111960A1 (es)	2017-05-26	2019-09-04	Incyte Corp	Formas cristalinas de un inhibidor de fgfr y procesos para su preparación
MA52493A (fr)	2018-05-04	2021-03-10	Incyte Corp	Sels d'un inhibiteur de fgfr
JP2021523121A (ja)	2018-05-04	2021-09-02	インサイト・コーポレイションＩｎｃｙｔｅＣｏｒｐｏｒａｔｉｏｎ	Ｆｇｆｒ阻害剤の固体形態及びその調製プロセス
MA52778A (fr)	2018-06-06	2021-04-21	Arena Pharm Inc	Méthodes de traitement de troubles associés au récepteur s1p1
WO2020185532A1 (en)	2019-03-08	2020-09-17	Incyte Corporation	Methods of treating cancer with an fgfr inhibitor
WO2021007269A1 (en)	2019-07-09	2021-01-14	Incyte Corporation	Bicyclic heterocycles as fgfr inhibitors
WO2021067374A1 (en)	2019-10-01	2021-04-08	Incyte Corporation	Bicyclic heterocycles as fgfr inhibitors
AU2020366006A1 (en)	2019-10-14	2022-04-21	Incyte Corporation	Bicyclic heterocycles as FGFR inhibitors
WO2021076728A1 (en)	2019-10-16	2021-04-22	Incyte Corporation	Bicyclic heterocycles as fgfr inhibitors
JP2023503403A (ja)	2019-11-29	2023-01-30	シピオライフサイエンシズリミテッド	リルピビリンを含む組成物及び腫瘍又は癌を治療するためのその使用
CN115151539A (zh)	2019-12-04	2022-10-04	因赛特公司	Fgfr抑制剂的衍生物
EP4069696A1 (en)	2019-12-04	2022-10-12	Incyte Corporation	Tricyclic heterocycles as fgfr inhibitors
US12012409B2 (en)	2020-01-15	2024-06-18	Incyte Corporation	Bicyclic heterocycles as FGFR inhibitors
KR102145925B1 (ko)	2020-03-03	2020-08-19	협동조합 바이오융합기술	사포닌 성분이 함유된 항 바이러스용 조성물의 제조방법
CN111875548A (zh) *	2020-07-16	2020-11-03	山东大学	一种5位芳环取代的二芳基嘧啶类衍生物及其制备方法与应用
US12065494B2 (en)	2021-04-12	2024-08-20	Incyte Corporation	Combination therapy comprising an FGFR inhibitor and a Nectin-4 targeting agent
WO2022261160A1 (en)	2021-06-09	2022-12-15	Incyte Corporation	Tricyclic heterocycles as fgfr inhibitors
CN116425683A (zh) *	2023-04-04	2023-07-14	上药康丽（常州）药业有限公司	一种米诺地尔的合成精制方法

Family Cites Families (67)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2742466A (en)		1956-04-17		Chx n nhx c c
US230963A (en)		1880-08-10		John kobeetson
US2671810A (en)	1952-05-24	1954-03-09	Du Pont	Long-chain diketones
US2748124A (en)	1954-05-06	1956-05-29	Searle & Co	1-(4-anilino-2-pyrimidino)-3-alkylureas
SU143808A1 (ru)	1961-02-14	1961-11-30	Н.В. Козлова	Способ получени 2-хлор-4,6-ди и 2,4,6-три-(2,4-дихлоранилин)-симм. триазинов
GB1010998A (en)	1962-10-09	1965-11-24	British Petroleum Co	Pyrimidine derivatives
US3478030A (en)	1966-06-27	1969-11-11	Abbott Lab	Benzamide substituted anilino aminopyrimidines
BE754242A (fr)	1970-07-15	1971-02-01	Geigy Ag J R	Diamino-s-triazines et dinitro-s-triazines
DE2038182C3 (de)	1970-07-31	1980-10-09	Ciba-Geigy Ag, Basel (Schweiz)	2-Substituierte 4,6-Diamino-stri azine
GB1483271A (en)	1975-03-22	1977-08-17	Ciba Geigy Ag	Pigment complexes
GB1477349A (en)	1975-09-24	1977-06-22	Ciba Geigy Ag	Azo pigments
US4096206A (en)	1976-02-09	1978-06-20	Borg-Warner Corporation	Flame-retardant triazines
FR2400535A1 (fr)	1977-01-27	1979-03-16	Borg Warner	Composition de polymere contenant des tris(haloarylamino)triazines ou des tris(haloarylthio)triazines fournissant une aptitude au retardement d'inflammation
FR2398740A1 (fr)	1978-11-06	1979-02-23	Borg Warner	Compose fournissant une aptitude au retardement d'inflammation dans un polymere
JPS57203072A (en)	1981-06-05	1982-12-13	Sankyo Co Ltd	4-anilinopyrimidine derivative, its preparation, antidepressant comprising it as active ingredient
US4659363A (en)	1983-07-25	1987-04-21	Ciba-Geigy Corporation	N-(2-nitrophenyl)-2-aminopyrimidine derivatives, the preparation and use thereof
US4652645A (en)	1983-11-16	1987-03-24	Ciba-Geigy Corporation	Cationic compounds
ATE60591T1 (de)	1984-06-25	1991-02-15	Ciba Geigy Ag	Pyrimidinderivate wirksam als schaedlingsbekaempfungsmittel.
JPH0784445B2 (ja) *	1986-12-03	1995-09-13	クミアイ化学工業株式会社	ピリミジン誘導体および農園芸用殺菌剤
DE68918804T2 (de)	1988-03-31	1995-02-23	Mitsubishi Chem Ind	Acyclische 6-substituierte pyrimidin nukleosid-abkömmlinge und antivirale mittel, die dieselben als aktive mittel enthalten.
JPH0252360A (ja)	1988-08-15	1990-02-21	Fujitsu Ltd	電子写真感光体
US4980371A (en)	1988-12-21	1990-12-25	Merrell Dow Pharmaceuticals	Antiretroviral furan ketones
FI95376C (fi)	1989-03-22	1996-01-25	Ciba Geigy Ag	Mikrobisidiset 2-anilino-pyrimidiinijohdannaiset
IE63502B1 (en)	1989-04-21	1995-05-03	Zeneca Ltd	Aminopyrimidine derivatives useful for treating cardiovascular disorders
JPH02300264A (ja)	1989-05-16	1990-12-12	Fuji Photo Film Co Ltd	アミノピリミジンアゾメチン色素とその製造方法
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
US5064963A (en)	1990-04-25	1991-11-12	American Cyanamid Company	Process for the synthesis of n-(3-(1h-imidazol-1-yl)phenyl-4-(substituted)-2-pyrimidinamines
GB9012592D0 (en)	1990-06-06	1990-07-25	Smithkline Beecham Intercredit	Compounds
IE75693B1 (en)	1990-07-10	1997-09-10	Janssen Pharmaceutica Nv	HIV-inhibiting benzeneacetamide derivatives
JPH04159381A (ja)	1990-10-23	1992-06-02	Arakawa Chem Ind Co Ltd	ロジンエステルの製造方法
EP0541966A3 (en)	1991-11-15	1994-09-07	American Cyanamid Co	Process for preparing amide derivatives from halomines and acid halides
US5283274A (en)	1992-06-19	1994-02-01	Uniroyal Chemical Company, Inc.	Substituted pyrimidines and substituted triazines as rubber-to-metal adhesion promoters
IL106324A (en)	1992-07-17	1998-09-24	Shell Int Research	Transformed pyrimidine compounds, their preparation and use as pesticides
US5516775A (en)	1992-08-31	1996-05-14	Ciba-Geigy Corporation	Further use of pyrimidine derivatives
EP0684818B1 (en)	1993-02-22	1999-05-06	Janssen Pharmaceutica N.V.	Method of reversing resistance of hiv-1 strains to zidovudine
KR960704855A (ko)	1993-10-12	1996-10-09	돈 엠. 커.	1n-알킬-n-아릴피리미딘아민 및 이들의 유도체 (1n-alkyl-n-arylpyrimidinamines and derivatives thereof)
JP3398152B2 (ja) *	1993-10-12	2003-04-21	ブリストル‐マイヤーズ・スクイブ・ファーマ・カンパニー	１ｎ−アルキル−ｎ−アリールピリミジンアミンおよびその誘導体
GB9325217D0 (en)	1993-12-09	1994-02-09	Zeneca Ltd	Pyrimidine derivatives
DE19509807A1 (de) *	1995-03-21	1996-09-26	Basf Ag	Verfahren zur Herstellung von Wirkstoffzubereitungen in Form einer festen Lösung des Wirkstoffs in einer Polymermatrix sowie mit diesem Verfahren hergestellte Wirkstoffzubereitungen
TW574214B (en)	1994-06-08	2004-02-01	Pfizer	Corticotropin releasing factor antagonists
IL114208A0 (en)	1994-06-27	1995-10-31	Merck & Co Inc	Combinations of compounds pharmaceutical compositions containing them and their use as hiv protease inhibitors
TW401303B (en)	1994-07-01	2000-08-11	Janssen Pharmaceutica Nv	Anti-HIV triple combination
US5574040A (en)	1995-01-06	1996-11-12	Picower Institute For Medical Research	Pyrimidine compounds and methods of use to derivatize neighboring lysine residues in proteins under physiologic conditions
JP3691101B2 (ja)	1995-01-24	2005-08-31	三洋電機株式会社	有機エレクトロルミネッセンス素子
DE19504832A1 (de) *	1995-02-14	1996-08-22	Basf Ag	Feste Wirkstoff-Zubereitungen
US5691364A (en)	1995-03-10	1997-11-25	Berlex Laboratories, Inc.	Benzamidine derivatives and their use as anti-coagulants
JPH09101590A (ja)	1995-07-28	1997-04-15	Fuji Photo Film Co Ltd	ハロゲン化銀カラー写真感光材料およびその包装体
US5837436A (en)	1995-07-28	1998-11-17	Fuji Photo Film Co., Ltd.	Silver halide color photographic material and package thereof
JPH0968784A (ja)	1995-08-31	1997-03-11	Fuji Photo Film Co Ltd	ハロゲン化銀カラー写真感光材料
JPH0980676A (ja)	1995-09-13	1997-03-28	Fuji Photo Film Co Ltd	ハロゲン化銀カラー写真感光材料およびその包装体
GB9519197D0 (en)	1995-09-20	1995-11-22	Affinity Chromatography Ltd	Novel affinity ligands and their use
GB9523675D0 (en)	1995-11-20	1996-01-24	Celltech Therapeutics Ltd	Chemical compounds
CN1163401A (zh)	1996-02-13	1997-10-29	李占元	全自动血球计数仪试剂及配制方法
GB9619284D0 (en)	1996-09-16	1996-10-30	Celltech Therapeutics Ltd	Chemical compounds
NO311614B1 (no) *	1996-10-01	2001-12-17	Janssen Pharmaceutica Nv	Substituerte diamino-1,3,5-triazinderivater
GB9705361D0 (en)	1997-03-14	1997-04-30	Celltech Therapeutics Ltd	Chemical compounds
EP0872233A1 (en) *	1997-04-14	1998-10-21	Janssen Pharmaceutica N.V.	Antiretroviral compositions with improved bioavailability
JPH11116555A (ja)	1997-10-14	1999-04-27	Ube Ind Ltd	４−アニリノピリミジン誘導体及びそれを有効成分とする農園芸用の殺虫・殺ダニ・殺菌剤
IL137922A0 (en)	1998-02-17	2001-10-31	Tularik Inc	Anti-viral pyrimidine derivatives
EP0945442A1 (en)	1998-03-27	1999-09-29	Janssen Pharmaceutica N.V.	Trisubstituted pyrimidine derivatives
BRPI9909191B8 (pt) *	1998-03-27	2021-07-06	Janssen Pharmaceutica Nv	derivados de pirimidina inibidores do hiv, seu uso e composição farmacêutica que os compreende
EP0945447A1 (en) *	1998-03-27	1999-09-29	Janssen Pharmaceutica N.V.	Trisubstituted 1,3,5-triazine derivatives for treatment of HIV infections
CZ299380B6 (cs) *	1998-03-27	2008-07-09	Janssen Pharmaceutica N. V.	Pyrimidinová sloucenina, použití této slouceniny pro prípravu léciva, farmaceutický prostredek tutoslouceninu obsahující, zpusob prípravy tohoto prostredku a uvedené slouceniny a kombinace a produktuvedenou slouceninu obsahující
JP2000111191A (ja)	1998-08-04	2000-04-18	Tokyo Gas Co Ltd	吸収冷温水機
HRP20010161B9 (hr)	1998-11-10	2014-10-24	Janssen Pharmaceutica N.V.	PIRIMIDINI KOJI INHIBIRAJU REPLIKACIJU HIV-a
JP4159381B2 (ja)	2003-02-24	2008-10-01	花王株式会社	歯ブラシ
US6876717B1 (en) *	2004-08-19	2005-04-05	Intel Corporation	Multi-stage programmable Johnson counter

2000
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Publication number	Publication date
AU2004224973C1 (en)	2006-06-01
IS6256A (is)	2002-01-31
HRP20020247B1 (hr)	2011-02-28
BR0014271A (pt)	2002-05-21
HK1048768A1 (en)	2003-04-17
ATE316781T1 (de)	2006-02-15
ZA200202289B (en)	2003-08-27
US20100172970A1 (en)	2010-07-08
EA200200401A1 (ru)	2002-10-31
AU7512700A (en)	2001-04-30
DE60025837D1 (de)	2006-04-13
US20070196478A1 (en)	2007-08-23
TR200200763T2 (tr)	2003-09-22
NO20021443D0 (no)	2002-03-22
WO2001022938A1 (en)	2001-04-05
BRPI0014271B1 (pt)	2021-06-22
CZ300712B6 (cs)	2009-07-22
PT1225874E (pt)	2006-06-30
CN1234347C (zh)	2006-01-04
HU228449B1 (en)	2013-03-28
AP2002002482A0 (en)	2002-06-30
DE60025837T2 (de)	2006-11-02
HUP0203568A3 (en)	2006-07-28
KR20020063847A (ko)	2002-08-05
KR100820605B1 (ko)	2008-04-08
CA2384188C (en)	2008-06-17
PL354026A1 (en)	2003-12-15
SK3762002A3 (en)	2002-09-10
CA2384188A1 (en)	2001-04-05
PL207590B1 (pl)	2011-01-31
US20060127487A1 (en)	2006-06-15
US7887845B2 (en)	2011-02-15
MXPA02003182A (es)	2002-09-30
US7241458B1 (en)	2007-07-10
EE200200151A (et)	2003-04-15
SK285240B6 (sk)	2006-09-07
CN1376057A (zh)	2002-10-23
CZ2002907A3 (cs)	2002-05-15
EE04991B1 (et)	2008-04-15
NO20021443L (no)	2002-03-22
KR20070036805A (ko)	2007-04-03
IS2567B (is)	2009-12-15
AU2004224973B2 (en)	2005-08-25
BG65754B1 (bg)	2009-10-30
HRP20020247A2 (en)	2004-04-30
HUP0203568A2 (hu)	2003-02-28
NZ517025A (en)	2003-07-25
UA74797C2 (ru)	2006-02-15
EP1225874B1 (en)	2006-02-01
JP2003510264A (ja)	2003-03-18
IL148801A0 (en)	2002-09-12
EP1225874A1 (en)	2002-07-31
AU2004224973A1 (en)	2004-11-25
HK1048768B (zh)	2006-08-04
DK1225874T3 (da)	2006-06-12
JP4919566B2 (ja)	2012-04-18
AP1639A (en)	2006-07-24
ES2258018T3 (es)	2006-08-16
BG106521A (bg)	2002-12-29
KR100785360B1 (ko)	2007-12-18
CY1105268T1 (el)	2010-03-03
OA12029A (en)	2006-04-28
EA005423B1 (ru)	2005-02-24
SI1225874T1 (sl)	2006-06-30
AU775360B2 (en)	2004-07-29

Publication	Publication Date	Title
NO333358B1 (no)	2013-05-13	Partikkel bestaende av en fast dispersjon
AU751573C (en)	2003-10-09	HIV inhibiting pyrimidine derivatives
OA11674A (en)	2005-01-12	HIV Replication inhibiting pyrimidines.
MXPA01003646A (en)	2001-12-04	Hiv replication inhibiting pyrimidines

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