ES2988283T3 - Composiciones comprimidas de macitentán, métodos y usos de las mismas - Google Patents

Composiciones comprimidas de macitentán, métodos y usos de las mismas Download PDF

Info

Publication number: ES2988283T3
Authority: ES; Spain
Prior art keywords: surfactant; total; alcohol diluent; macitentan; sugar alcohol
Prior art date: 2019-07-05
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.): Active

Application number

ES20750358T

Other languages

English (en)

Spanish (es)

Inventor

Serra João Pedro Silva

Pereira Ricardo José Camilo Ferreira

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tecnimede Sociedade Tecnico Medicinal SA

Original Assignee

Tecnimede Sociedade Tecnico Medicinal SA

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.)

2019-07-05

Filing date

2020-07-03

Publication date

2024-11-19

2020-07-03 Application filed by Tecnimede Sociedade Tecnico Medicinal SA filed Critical Tecnimede Sociedade Tecnico Medicinal SA

2020-07-03 Priority claimed from PCT/IB2020/056304 external-priority patent/WO2021005478A1/en

2024-11-19 Application granted granted Critical

2024-11-19 Publication of ES2988283T3 publication Critical patent/ES2988283T3/es

Status Active legal-status Critical Current

2040-07-03 Anticipated expiration legal-status Critical

Links

239000000203 mixture Substances 0.000 title claims abstract description 138
JGCMEBMXRHSZKX-UHFFFAOYSA-N macitentan Chemical group C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCC)=NC=NC=1OCCOC1=NC=C(Br)C=N1 JGCMEBMXRHSZKX-UHFFFAOYSA-N 0.000 title claims abstract description 84
229960001039 macitentan Drugs 0.000 title claims abstract description 77
238000000034 method Methods 0.000 title claims abstract description 18
239000003085 diluting agent Substances 0.000 claims abstract description 55
239000004094 surface-active agent Substances 0.000 claims abstract description 52
150000005846 sugar alcohols Chemical class 0.000 claims abstract description 47
239000007787 solid Substances 0.000 claims abstract description 24
239000008203 oral pharmaceutical composition Substances 0.000 claims abstract description 21
206010064911 Pulmonary arterial hypertension Diseases 0.000 claims abstract description 14
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 28
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 25
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 25
229920000053 polysorbate 80 Polymers 0.000 claims description 25
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 20
229940068968 polysorbate 80 Drugs 0.000 claims description 20
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 18
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 18
239000000811 xylitol Substances 0.000 claims description 18
229960002675 xylitol Drugs 0.000 claims description 18
235000010447 xylitol Nutrition 0.000 claims description 18
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 18
239000008187 granular material Substances 0.000 claims description 16
239000000845 maltitol Substances 0.000 claims description 15
235000010449 maltitol Nutrition 0.000 claims description 15
VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 claims description 15
229940035436 maltitol Drugs 0.000 claims description 15
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 14
229930195725 Mannitol Natural products 0.000 claims description 14
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 14
235000019359 magnesium stearate Nutrition 0.000 claims description 14
239000000594 mannitol Substances 0.000 claims description 14
235000010355 mannitol Nutrition 0.000 claims description 14
239000011230 binding agent Substances 0.000 claims description 13
239000007884 disintegrant Substances 0.000 claims description 13
229920000168 Microcrystalline cellulose Polymers 0.000 claims description 12
229960001855 mannitol Drugs 0.000 claims description 12
235000019813 microcrystalline cellulose Nutrition 0.000 claims description 12
229940016286 microcrystalline cellulose Drugs 0.000 claims description 12
239000008108 microcrystalline cellulose Substances 0.000 claims description 12
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 10
229940069328 povidone Drugs 0.000 claims description 10
239000000314 lubricant Substances 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
229920003109 sodium starch glycolate Polymers 0.000 claims description 8
229940079832 sodium starch glycolate Drugs 0.000 claims description 8
239000008109 sodium starch glycolate Substances 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 5
229960000913 crospovidone Drugs 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims description 4
229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims description 4
238000005550 wet granulation Methods 0.000 claims description 2
238000004090 dissolution Methods 0.000 abstract description 16
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
230000000052 comparative effect Effects 0.000 description 13
239000012535 impurity Substances 0.000 description 12
239000003826 tablet Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229940058799 opsumit Drugs 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 5
102000002045 Endothelin Human genes 0.000 description 4
108050009340 Endothelin Proteins 0.000 description 4
ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000007916 tablet composition Substances 0.000 description 4
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound 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 GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
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
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000007922 dissolution test Methods 0.000 description 3
239000000945 filler Substances 0.000 description 3
238000005469 granulation Methods 0.000 description 3
230000003179 granulation Effects 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229960001021 lactose monohydrate Drugs 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229940118365 Endothelin receptor antagonist Drugs 0.000 description 2
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
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000011324 bead Substances 0.000 description 2
239000007894 caplet Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
229920001531 copovidone Polymers 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
239000012738 dissolution medium Substances 0.000 description 2
239000002308 endothelin receptor antagonist Substances 0.000 description 2
239000002050 international nonproprietary name Substances 0.000 description 2
229960001375 lactose Drugs 0.000 description 2
239000008101 lactose Substances 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
229950008882 polysorbate Drugs 0.000 description 2
238000011002 quantification Methods 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
229920002785 Croscarmellose sodium Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
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 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
229960004977 anhydrous lactose Drugs 0.000 description 1
229960000074 biopharmaceutical Drugs 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229960001714 calcium phosphate Drugs 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229940057948 magnesium stearate Drugs 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
-1 microtablets Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
238000007614 solvation Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1

Landscapes

Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ES20750358T 2019-07-05 2020-07-03 Composiciones comprimidas de macitentán, métodos y usos de las mismas Active ES2988283T3 (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
PT2019115632		2019-07-05
EP19185065		2019-07-08
PCT/IB2020/056304 WO2021005478A1 (en)	2019-07-05	2020-07-03	Compressed macitentan compositions, methods and uses thereof

Publications (1)

Publication Number	Publication Date
ES2988283T3 true ES2988283T3 (es)	2024-11-19

Family

ID=82258125

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES20750358T Active ES2988283T3 (es)	2019-07-05	2020-07-03	Composiciones comprimidas de macitentán, métodos y usos de las mismas

Country Status (8)

Country	Link
ES (1)	ES2988283T3 (lt)
HR (1)	HRP20241209T1 (lt)
LT (1)	LT3993777T (lt)
MA (1)	MA56458B1 (lt)
PL (1)	PL3993777T3 (lt)
RS (1)	RS66024B1 (lt)
SI (1)	SI3993777T1 (lt)
SM (1)	SMT202400342T1 (lt)

2020
- 2020-07-03 SI SI202030487T patent/SI3993777T1/sl unknown
- 2020-07-03 ES ES20750358T patent/ES2988283T3/es active Active
- 2020-07-03 MA MA56458A patent/MA56458B1/fr unknown
- 2020-07-03 HR HRP20241209TT patent/HRP20241209T1/hr unknown
- 2020-07-03 RS RS20240975A patent/RS66024B1/sr unknown
- 2020-07-03 SM SM20240342T patent/SMT202400342T1/it unknown
- 2020-07-03 LT LTEPPCT/IB2020/056304T patent/LT3993777T/lt unknown
- 2020-07-03 PL PL20750358.2T patent/PL3993777T3/pl unknown

Also Published As

Publication number	Publication date
SI3993777T1 (sl)	2024-12-31
LT3993777T (lt)	2024-09-10
MA56458B1 (fr)	2024-09-30
SMT202400342T1 (it)	2024-11-15
PL3993777T3 (pl)	2024-12-16
RS66024B1 (sr)	2024-11-29
HRP20241209T1 (hr)	2024-11-22
MA56458A (fr)	2022-05-11

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