NZ553323A - Hydrochloride of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile, also named TMC278 - Google Patents
Hydrochloride of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile, also named TMC278Info
- Publication number
- NZ553323A NZ553323A NZ553323A NZ55332305A NZ553323A NZ 553323 A NZ553323 A NZ 553323A NZ 553323 A NZ553323 A NZ 553323A NZ 55332305 A NZ55332305 A NZ 55332305A NZ 553323 A NZ553323 A NZ 553323A
- Authority
- NZ
- New Zealand
- Prior art keywords
- pharmaceutical composition
- compound
- formula
- composition according
- tablet
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 29
- YIBOMRUWOWDFLG-ONEGZZNKSA-N rilpivirine Chemical compound CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-ONEGZZNKSA-N 0.000 title abstract description 19
- YIBOMRUWOWDFLG-UHFFFAOYSA-N 4-[[4-[4-(2-cyanoethenyl)-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C=CC#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-UHFFFAOYSA-N 0.000 title abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 174
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 108
- 239000008194 pharmaceutical composition Substances 0.000 claims description 73
- 239000000080 wetting agent Substances 0.000 claims description 56
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 42
- 239000002585 base Substances 0.000 claims description 34
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 26
- 229960001021 lactose monohydrate Drugs 0.000 claims description 26
- -1 sorbitan fatty acid esters Chemical class 0.000 claims description 26
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 25
- 239000012458 free base Substances 0.000 claims description 25
- 229920002785 Croscarmellose sodium Polymers 0.000 claims description 24
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 24
- 229960001681 croscarmellose sodium Drugs 0.000 claims description 24
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims description 24
- 235000019359 magnesium stearate Nutrition 0.000 claims description 24
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 24
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 24
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 24
- 239000003937 drug carrier Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 239000002245 particle Substances 0.000 claims description 23
- 229940068977 polysorbate 20 Drugs 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 229920001223 polyethylene glycol Polymers 0.000 claims description 19
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 17
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 17
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims description 17
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 claims description 16
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 16
- 229920003125 hypromellose 2910 Polymers 0.000 claims description 16
- 229940031672 hypromellose 2910 Drugs 0.000 claims description 16
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 16
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 16
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 16
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000002202 Polyethylene glycol Substances 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
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- 239000007787 solid Substances 0.000 claims description 8
- VERWQPYQDXWOGT-LVJNJWHOSA-N 4-amino-5-fluoro-1-[(2r,5s)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;[[(2r)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VERWQPYQDXWOGT-LVJNJWHOSA-N 0.000 claims description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
- 239000000314 lubricant Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002773 nucleotide Substances 0.000 claims description 7
- 125000003729 nucleotide group Chemical group 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- 238000001157 Fourier transform infrared spectrum Methods 0.000 claims description 6
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- 150000004682 monohydrates Chemical class 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract description 5
- 239000003826 tablet Substances 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 27
- 239000004359 castor oil Substances 0.000 description 24
- 235000019438 castor oil Nutrition 0.000 description 24
- 239000003814 drug Substances 0.000 description 24
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 24
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- 239000000243 solution Substances 0.000 description 21
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
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- 150000003839 salts Chemical class 0.000 description 18
- 229940079593 drug Drugs 0.000 description 17
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 17
- 239000008213 purified water Substances 0.000 description 17
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 16
- 229940049964 oleate Drugs 0.000 description 14
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 12
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- 238000009472 formulation Methods 0.000 description 11
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- 230000000798 anti-retroviral effect Effects 0.000 description 10
- 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 10
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 10
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 6
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- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (48)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MYPI20043578A MY169670A (en) | 2003-09-03 | 2004-09-02 | Combinations of a pyrimidine containing nnrti with rt inhibitors |
EP04052028 | 2004-09-03 | ||
EP05101467 | 2005-02-25 | ||
PCT/EP2005/054342 WO2006024668A1 (en) | 2004-09-02 | 2005-09-02 | Hydrochloride of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl] amino]benzonitrile |
Publications (1)
Publication Number | Publication Date |
---|---|
NZ553323A true NZ553323A (en) | 2010-07-30 |
Family
ID=42357963
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ553323A NZ553323A (en) | 2004-09-02 | 2005-09-02 | Hydrochloride of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile, also named TMC278 |
Country Status (1)
Country | Link |
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NZ (1) | NZ553323A (en) |
-
2005
- 2005-09-02 NZ NZ553323A patent/NZ553323A/en unknown
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