KR20140093230A - 즉시 방출 4-메틸-3-[[4-(3-피리디닐)-2-피리미디닐]아미노]-n-[5-(4-메틸-1h-이미다졸-1-일)-3-(트리플루오로메틸)페닐] 벤즈아미드 제제 - Google Patents
즉시 방출 4-메틸-3-[[4-(3-피리디닐)-2-피리미디닐]아미노]-n-[5-(4-메틸-1h-이미다졸-1-일)-3-(트리플루오로메틸)페닐] 벤즈아미드 제제 Download PDFInfo
- Publication number
- KR20140093230A KR20140093230A KR1020147012521A KR20147012521A KR20140093230A KR 20140093230 A KR20140093230 A KR 20140093230A KR 1020147012521 A KR1020147012521 A KR 1020147012521A KR 20147012521 A KR20147012521 A KR 20147012521A KR 20140093230 A KR20140093230 A KR 20140093230A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- dosage form
- solid dosage
- phenyl
- pyrimidinyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Ceased
Links
- HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 title description 46
- 239000000203 mixture Substances 0.000 title description 31
- 238000009472 formulation Methods 0.000 title description 14
- 239000012729 immediate-release (IR) formulation Substances 0.000 title description 4
- 239000007909 solid dosage form Substances 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 230000003111 delayed effect Effects 0.000 claims abstract description 9
- -1 4-methyl-1H-imidazol-1-yl Chemical group 0.000 claims description 61
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000002775 capsule Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 10
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 8
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 6
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 6
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 4
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical group 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 claims description 4
- 239000007903 gelatin capsule Substances 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 239000005536 L01XE08 - Nilotinib Substances 0.000 description 45
- 125000000217 alkyl group Chemical group 0.000 description 44
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 13
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
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- 239000007888 film coating Substances 0.000 description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000007906 compression Methods 0.000 description 8
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- 229910052736 halogen Inorganic materials 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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- 125000003118 aryl group Chemical group 0.000 description 7
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 description 7
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- 125000001589 carboacyl group Chemical group 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
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- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 230000004584 weight gain Effects 0.000 description 5
- 235000019786 weight gain Nutrition 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000007963 capsule composition Substances 0.000 description 4
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- 150000003254 radicals Chemical class 0.000 description 4
- 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 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000037406 food intake Effects 0.000 description 3
- 229920001002 functional polymer Polymers 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920002689 polyvinyl acetate Polymers 0.000 description 3
- 239000011118 polyvinyl acetate Substances 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
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- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 238000005550 wet granulation Methods 0.000 description 3
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- YCBPQSYLYYBPDW-UHFFFAOYSA-N 4-methyl-n-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]benzamide;hydrate;hydrochloride Chemical group O.Cl.C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 YCBPQSYLYYBPDW-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
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- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
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- 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
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- A61K9/20—Pills, tablets, discs, rods
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161559281P | 2011-11-14 | 2011-11-14 | |
| US61/559,281 | 2011-11-14 | ||
| PCT/US2012/064610 WO2013074432A1 (en) | 2011-11-14 | 2012-11-12 | Immediate release 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-n-[5-(4-methyl- 1h-imidazol-1-yl)-3-(trifluoromethyl)phenyl] benzamide formulation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140093230A true KR20140093230A (ko) | 2014-07-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147012521A Ceased KR20140093230A (ko) | 2011-11-14 | 2012-11-12 | 즉시 방출 4-메틸-3-[[4-(3-피리디닐)-2-피리미디닐]아미노]-n-[5-(4-메틸-1h-이미다졸-1-일)-3-(트리플루오로메틸)페닐] 벤즈아미드 제제 |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP2779995A1 (enExample) |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2792360A1 (en) | 2013-04-18 | 2014-10-22 | IP Gesellschaft für Management mbH | (1aR,12bS)-8-cyclohexyl-11-fluoro-N-((1-methylcyclopropyl)sulfonyl)-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-1,1a,2,2b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxamide for use in treating HCV |
| CZ2017821A3 (cs) | 2017-12-20 | 2019-07-03 | Zentiva, K.S. | Léková forma obsahující krystalický nilotinib |
| JP7378279B2 (ja) * | 2019-11-18 | 2023-11-13 | 日本化薬株式会社 | ニロチニブを有効成分とする医薬錠剤及びその製造方法 |
| JP7489849B2 (ja) * | 2020-07-20 | 2024-05-24 | 日本化薬株式会社 | ニロチニブ錠剤 |
| JP7776274B2 (ja) * | 2021-07-19 | 2025-11-26 | 日本化薬株式会社 | ニロチニブ錠剤およびその製造方法 |
| JP7776275B2 (ja) * | 2021-07-26 | 2025-11-26 | 日本化薬株式会社 | ニロチニブ錠剤およびその製造方法 |
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| GB0215676D0 (en) * | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| GT200600315A (es) | 2005-07-20 | 2007-03-19 | Formas cristalinas de 4-metilo-n-[3-(4-metilo-imidazol-1-ilo)-5-trifluorometilo-fenilo]-3-(4-pyridina-3-ilo-pirimidina-2-iloamino)-benzamida | |
| GT200600316A (es) | 2005-07-20 | 2007-04-02 | Sales de 4-metilo-n-(3-(4-metilo-imidazol-1-ilo)-5-trifluorometilo-fenilo)-3-(4-piridina-3-ilo-pirimidina-2-iloamino)- benzamida. | |
| EP1923053A1 (en) * | 2006-09-27 | 2008-05-21 | Novartis AG | Pharmaceutical compositions comprising nilotinib or its salt |
| US20100136097A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Systems for modulating inflammation |
| IN2011CH01887A (enExample) * | 2011-06-02 | 2012-12-14 |
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- 2014-05-14 GT GT201400094A patent/GT201400094A/es unknown
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Also Published As
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| HK1197025A1 (en) | 2015-01-02 |
| MA35636B1 (fr) | 2014-11-01 |
| EP2779995A1 (en) | 2014-09-24 |
| BR112014011518A2 (pt) | 2017-05-16 |
| NZ623844A (en) | 2016-09-30 |
| TWI574690B (zh) | 2017-03-21 |
| WO2013074432A1 (en) | 2013-05-23 |
| JP2014533283A (ja) | 2014-12-11 |
| CN103930094A (zh) | 2014-07-16 |
| GT201400094A (es) | 2017-09-28 |
| AU2012339829A1 (en) | 2014-05-29 |
| EA201490960A1 (ru) | 2014-08-29 |
| AR088844A1 (es) | 2014-07-10 |
| IL232480A0 (en) | 2014-06-30 |
| MX2014005874A (es) | 2014-06-23 |
| TN2014000177A1 (en) | 2015-09-30 |
| CO6960546A2 (es) | 2014-05-30 |
| PE20141337A1 (es) | 2014-10-16 |
| ZA201402756B (en) | 2015-04-29 |
| JP6275645B2 (ja) | 2018-02-07 |
| PH12014501062A1 (en) | 2014-06-23 |
| TW201325594A (zh) | 2013-07-01 |
| SG10201707768RA (en) | 2017-10-30 |
| CA2855503A1 (en) | 2013-05-23 |
| SG11201401476TA (en) | 2014-10-30 |
| PH12014501062B1 (en) | 2018-04-20 |
| AU2012339829B2 (en) | 2016-05-12 |
| CL2014001247A1 (es) | 2014-10-17 |
| IN2014DN03416A (enExample) | 2015-06-26 |
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