CN106619643A - Pharmaceutical composition containing ibrutinib - Google Patents
Pharmaceutical composition containing ibrutinib Download PDFInfo
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- CN106619643A CN106619643A CN201610994474.1A CN201610994474A CN106619643A CN 106619643 A CN106619643 A CN 106619643A CN 201610994474 A CN201610994474 A CN 201610994474A CN 106619643 A CN106619643 A CN 106619643A
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- pharmaceutical composition
- shandong
- buddhist nun
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- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
Abstract
The invention relates to a pharmaceutical composition containing ibrutinib. The pharmaceutical composition is prepared from, by weight, 13-15 parts of ibrutinib, 30-50 parts of solvent, 20-30 parts of solubilizer, 8-12 parts of filler, 6-10 parts of disintegrant and 21-26 parts of officinal organic acid, wherein the solvent is glycerolformal, and the officinal organic acid is a mixture of oleic acid and glyceryl monooleate based on the mass ratio of (1.7-2.1):1. The pharmaceutical composition containing ibrutinib has the advantages that compared with traditional pharmaceutical compositions, the variety of the solvent in the formula is changed, glycerolformal which is high in safety performance serves as the solvent with dosage unlimited, and multiple medicines are soluble in glycerolformal; meanwhile, due to the fact that the officinal organic acid is a mixture of oleic acid and glyceryl monooleate, the pharmaceutical composition containing ibrutinib is more stable and simpler than traditional pharmaceutical compositions adopting single officinal organic acid.
Description
Technical field
The invention belongs to field of medicine preparing technology, more particularly to a kind of containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong.
Background technology
For Buddhist nun (ibrutinib) it is a kind of small molecule BTK inhibitor according to Shandong, can be with the cysteine in BTK active center
Residue covalent is combined, so as to suppress its activity.BTK full name Bruton ' styrosinekinase, in BCR signal paths, cell
Signal, the migration of mediate B cell, chemotactic, adhesion are transmitted in factor acceptor signal path.Preclinical study is proved, according to Shandong for Buddhist nun
(ibrutinib) propagation, the existence of malignant B cell can be suppressed.
Jing retrievals find that the A of patent CN 105640961 discloses a kind of containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, its activity
Component is the pharmaceutically acceptable organic acid such as saturation or unsaturated fatty acid, substituted carboxylic acid of long-chain in being characterized in selecting for Buddhist nun according to Shandong
Or wherein one or more sour mixture or fish oil are required as lipophilic ingredients according to the difference of each dosage form, can be added without
Or adding appropriate water to make hydrophilic matrix, the formula of said composition is applicable to soft capsule, ointment, eye drop, oral liquid
And the preparation of the dosage form such as injection.But this patent containing according to Shandong for Buddhist nun pharmaceutical composition, solvent is from ethanol or Propylene Glycol
Or the mixed liquor of ethanol and Propylene Glycol, but the consumption of Propylene Glycol is restricted, thus certain safety issue can be caused.
Therefore, solvent load is unrestricted in a kind of pharmaceutical composition of research and development and can guarantee that using for pharmaceutical composition is safe
Property containing being necessary for the pharmaceutical composition of Buddhist nun according to Shandong.
The content of the invention
The technical problem to be solved in the present invention be to provide it is a kind of containing according to Shandong for Buddhist nun pharmaceutical composition, in the pharmaceutical composition
Solvent load is unrestricted and can guarantee that the safety in utilization of pharmaceutical composition.
To solve above-mentioned technical problem, the technical scheme is that：It is a kind of containing according to Shandong for Buddhist nun pharmaceutical composition, its wound
Newly point is：Component of the described pharmaceutical composition comprising following weight portion：Buddhist nun's 13-15 parts, solvent 30-50 parts, solubilising are replaced according to Shandong
Agent 20-30 parts, filler 8-12 parts, disintegrating agent 6-10 parts and pharmaceutically acceptable organic acid 21-26 parts；Wherein, described solvent is glycerol
Formal, described pharmaceutically acceptable organic acid is the mixture of Oleic acid and olein, and the mass ratio of Oleic acid and olein
For 1.7-2.1:1.
Further, described solubilizing agent is from the hydrophilic surfactant that HLB value is 15～18.
Further, described hydrophilic surfactant is in polyoxyethylene aliphatic alcohol ether or polyoxyethylene laurate
It is a kind of.
Further, described filler is N- Methylaminoformyl chlorides.
Further, described disintegrating agent is mixed by carboxymethylcellulose calcium and Microcrystalline Cellulose, and carboxymethyl is fine
The mass ratio of the plain calcium of dimension and Microcrystalline Cellulose is 1:2.1～2.5.
It is an advantage of the current invention that：
(1) it is of the invention, for the pharmaceutical composition of Buddhist nun, compared with conventional medicament compositionss, to change solvent in formula containing according to Shandong
Species, solvent selects glycerol formal, and its consumption is unrestricted, and safety is also good, and to the dissolubility of multi-medicament all
It is relatively good；Meanwhile, pharmaceutically acceptable organic acid selects the mixture of Oleic acid and olein, and the mass ratio of Oleic acid and olein
For 1.7-2.1:1, using the mixture of pharmaceutically acceptable organic acid, compared with single pharmaceutically acceptable organic acid so that the drug regimen of the present invention
Thing is more more stable than traditional pharmaceutical composition and more succinct.
(2) it is of the invention containing according to Shandong for Buddhist nun pharmaceutical composition, solubilizing agent lived from the water-wetted surface that HLB value is 15～18
Property agent, and hydrophilic surfactant is the one kind in polyoxyethylene aliphatic alcohol ether or polyoxyethylene laurate, Polyethylene oxide fat
Fat alcohol ether is good with the compatibility of other surfaces activating agent, and insensitive to hard water, cold washing performance is good, and with excellent breast
Change, dispersion, solubilising, antistatic, dirt-removing power；Polyoxyethylene laurate is a kind of nonionic surfactant, is dissolved in water, easily
Degraded, the facile hydrolysiss under strong acid, basic conditions, it may have excellent emulsifying, dispersion, solubilising, antistatic, dirt-removing power are excellent
Calcium and magnesium dispersibility.
(3) it is of the invention containing according to Shandong for Buddhist nun pharmaceutical composition, filler selects N- Methylaminoformyl chlorides, and then makes filling
Agent has direct compressibility；Disintegrating agent selects the mixture of carboxymethylcellulose calcium and Microcrystalline Cellulose, and carboxymethyl cellulose
The mass ratio of calcium and Microcrystalline Cellulose is 1:2.1～2.5, can greatly shorten tabletting dissolve in water or disintegrate time.
Specific embodiment
The present invention is containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, component of the pharmaceutical composition comprising following weight portion：Replace according to Shandong
Buddhist nun's 13-15 parts, solvent 30-50 parts, solubilizing agent 20-30 parts, filler 8-12 parts, disintegrating agent 6-10 parts and pharmaceutically acceptable organic acid 21-
26 parts；Wherein, solvent is glycerol formal, and pharmaceutically acceptable organic acid is Oleic acid and the mixture of olein, and Oleic acid and Oleic acid
The mass ratio of glyceride is 1.7-2.1:1.
Used as embodiment, more specifically embodiment is solubilizing agent from the hydrophilic surfactant that HLB value is 15～18,
And hydrophilic surfactant is polyoxyethylene aliphatic alcohol ether or the one kind in polyoxyethylene laurate；Filler is N- methylaminos
Formyl chloride；Disintegrating agent is mixed by carboxymethylcellulose calcium and Microcrystalline Cellulose, and carboxymethylcellulose calcium and microcrystalline cellulose
The mass ratio of element is 1:2.1～2.5.
Embodiment 1
The present embodiment is containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, component of the pharmaceutical composition comprising following weight portion：According to Shandong
For 13 parts of Buddhist nun, 50 parts of glycerol formal solvent, 30 parts of solubilizing agent, 12 parts of N- Methylaminoformyl chlorides filler, 10 parts of disintegrating agent and
26 parts of pharmaceutically acceptable organic acid；Wherein, solubilizing agent is from the hydrophilic surfactant that HLB value is 15～18, and hydrophilic surfactant
For polyoxyethylene aliphatic alcohol ether；Disintegrating agent is mixed by carboxymethylcellulose calcium and Microcrystalline Cellulose, and carboxymethyl cellulose
3.23 parts of calcium, 6.77 parts of Microcrystalline Cellulose；Pharmaceutically acceptable organic acid is Oleic acid and the mixture of olein, and 16.37 parts of Oleic acid,
9.63 parts of olein.
Embodiment 2
The present embodiment is containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, component of the pharmaceutical composition comprising following weight portion：According to Shandong
For 13 parts of Buddhist nun, 50 parts of glycerol formal solvent, 30 parts of solubilizing agent, 12 parts of N- Methylaminoformyl chlorides filler, 10 parts of disintegrating agent and
26 parts of pharmaceutically acceptable organic acid；Wherein, solubilizing agent is from the hydrophilic surfactant that HLB value is 15～18, and hydrophilic surfactant
For polyoxyethylene aliphatic alcohol ether；Disintegrating agent is mixed by carboxymethylcellulose calcium and Microcrystalline Cellulose, and carboxymethyl cellulose
2.86 parts of calcium, 7.14 parts of Microcrystalline Cellulose；Pharmaceutically acceptable organic acid is Oleic acid and the mixture of olein, and 17.61 parts of Oleic acid,
8.39 parts of olein.
Embodiment 3
The present embodiment is containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, component of the pharmaceutical composition comprising following weight portion：According to Shandong
For 13 parts of Buddhist nun, 50 parts of glycerol formal solvent, 30 parts of solubilizing agent, 12 parts of N- Methylaminoformyl chlorides filler, 10 parts of disintegrating agent and
26 parts of pharmaceutically acceptable organic acid；Wherein, solubilizing agent is from the hydrophilic surfactant that HLB value is 15～18, and hydrophilic surfactant
For polyoxyethylene aliphatic alcohol ether；Disintegrating agent is mixed by carboxymethylcellulose calcium and Microcrystalline Cellulose, and carboxymethyl cellulose
3.03 parts of calcium, 6.97 parts of Microcrystalline Cellulose；Pharmaceutically acceptable organic acid is Oleic acid and the mixture of olein, and 17.03 parts of Oleic acid,
8.97 parts of olein.
Table 1 is Croscarmellose Sodium and Microcrystalline Cellulose in disintegrating agent in embodiment 1-3, oil in pharmaceutically acceptable organic acid
Acid contrasts form with olein mass ratio：
Embodiment 4
Compared with Example 3, other are constant for the present embodiment, change hydrophilic surfactant species, the present embodiment contain according to
Replace the pharmaceutical composition of Buddhist nun, component of the pharmaceutical composition comprising following weight portion in Shandong：13 parts of Buddhist nun is replaced according to Shandong, glycerol formal is molten
26 parts of 50 parts of agent, 30 parts of solubilizing agent, 12 parts of N- Methylaminoformyl chlorides filler, 10 parts of disintegrating agent and pharmaceutically acceptable organic acid；Wherein, increase
Solvent is from the hydrophilic surfactant that HLB value is 15～18, and hydrophilic surfactant is polyoxyethylene laurate；Disintegrate
Agent is mixed by carboxymethylcellulose calcium and Microcrystalline Cellulose, and 3.03 parts of carboxymethylcellulose calcium, Microcrystalline Cellulose 6.97
Part；Pharmaceutically acceptable organic acid is Oleic acid and the mixture of olein, and 17.03 parts of Oleic acid, 8.97 parts of olein.
Embodiment 5
The present embodiment is containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, component of the pharmaceutical composition comprising following weight portion：According to Shandong
For 15 parts of Buddhist nun, 30 parts of glycerol formal solvent, 20 parts of solubilizing agent, 8 parts of N- Methylaminoformyl chlorides filler, 6 parts of disintegrating agent and medicine
With 21 parts of organic acid；Wherein, solubilizing agent is from the hydrophilic surfactant that HLB value is 15～18, and hydrophilic surfactant
Polyoxyethylene aliphatic alcohol ether；Disintegrating agent is mixed by carboxymethylcellulose calcium and Microcrystalline Cellulose, and carboxymethylcellulose calcium
1.82 parts, 4.18 parts of Microcrystalline Cellulose；Pharmaceutically acceptable organic acid is Oleic acid and the mixture of olein, and 13.76 parts of Oleic acid, oil
7.24 parts of acid glyceride.
Embodiment 6
The present embodiment is containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, component of the pharmaceutical composition comprising following weight portion：According to Shandong
For 14 parts of Buddhist nun, 40 parts of glycerol formal solvent, 25 parts of solubilizing agent, 10 parts of N- Methylaminoformyl chlorides filler, 8 parts of disintegrating agent and medicine
With 24 parts of organic acid；Wherein, solubilizing agent is from the hydrophilic surfactant that HLB value is 15～18, and hydrophilic surfactant
Polyoxyethylene aliphatic alcohol ether；Disintegrating agent is mixed by carboxymethylcellulose calcium and Microcrystalline Cellulose, and carboxymethylcellulose calcium
2.42 parts, 5.58 parts of Microcrystalline Cellulose；Pharmaceutically acceptable organic acid is Oleic acid and the mixture of olein, and 15.72 parts of Oleic acid, oil
8.28 parts of acid glyceride.
The embodiment 3 of table 2 and embodiment 5-6 are contrasted containing the mass ratio according to Shandong for each component in the pharmaceutical composition of Buddhist nun
| Component | Embodiment 3 | Embodiment 5 | Embodiment 6 |
| Buddhist nun is replaced according to Shandong | 13 | 15 | 14 |
| Solvent | 50 | 30 | 40 |
| Solubilizing agent | 30 | 20 | 25 |
| Filler | 12 | 8 | 10 |
| Disintegrating agent | 10 | 6 | 8 |
| Pharmaceutically acceptable organic acid | 26 | 21 | 24 |
For relatively more each embodiment and the solubility property of commercially available hard capsule, compositionss prepared by each embodiment are taken with No. 0
In gelatine capsule shell, with commercially available hard capsule (trade name：IMBRUVICATM, specification：140mg) it is respectively compared in 0.1mol/L
Dissolved corrosion in hydrochloric acid solution, pH4.5 acetate buffers and pH6.8 phosphate buffers, the results are shown in Table 3, table 4 and table 5.
The stripping curve in 0.1mol/L hydrochloric acid solutions compares (%) embodiment 1-6 of table 3 with commercial preparation
The stripping curve in pH4.5 acetate buffers compares (%) embodiment 1-6 of table 4 with commercial preparation
The stripping curve in pH6.8 phosphate buffers compares (%) embodiment 1-6 of table 5 with commercial preparation
By table 4～5 as can be seen that embodiment 1～5 is compared with commercial reagent, its solubility property is greatly promoted, and each enforcement
Example is compared, and embodiment 6 is most preferred embodiment.
The ultimate principle and principal character and advantages of the present invention of the present invention has been shown and described above.The skill of the industry
Simply explanation of the art personnel it should be appreciated that the present invention is not restricted to the described embodiments, described in above-described embodiment and description
The principle of the present invention, without departing from the spirit and scope of the present invention, the present invention also has various changes and modifications, these
Changes and improvements are both fallen within scope of the claimed invention.The claimed scope of the invention by appending claims and
Its equivalent thereof.
Claims (5)
1. a kind of containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, it is characterised in that：Group of the described pharmaceutical composition comprising following weight portion
Point：Buddhist nun's 13-15 parts, solvent 30-50 parts, solubilizing agent 20-30 parts, filler 8-12 parts, disintegrating agent 6-10 parts and medicinal are replaced according to Shandong
Organic acid 21-26 parts；Wherein, described solvent is glycerol formal, and described pharmaceutically acceptable organic acid is Oleic acid and olein
Mixture, and the mass ratio of Oleic acid and olein is 1.7-2.1:1.
2. according to claim 1 containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, it is characterised in that：Described solubilizing agent is selected
HLB value is 15～18 hydrophilic surfactant.
3. according to claim 2 containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, it is characterised in that：Described hydrophilic surfactant
Agent is polyoxyethylene aliphatic alcohol ether or the one kind in polyoxyethylene laurate.
4. according to claim 1 containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, it is characterised in that：Described filler is N- first
Carbamyl chloride.
5. according to claim 1 containing the pharmaceutical composition that Buddhist nun is replaced according to Shandong, it is characterised in that：Described disintegrating agent is by carboxylic first
Base cellulose calcium and Microcrystalline Cellulose are mixed, and the mass ratio of carboxymethylcellulose calcium and Microcrystalline Cellulose is 1:2.1～
2.5。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610994474.1A CN106619643A (en) | 2016-11-11 | 2016-11-11 | Pharmaceutical composition containing ibrutinib |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610994474.1A CN106619643A (en) | 2016-11-11 | 2016-11-11 | Pharmaceutical composition containing ibrutinib |
Publications (1)
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| CN106619643A true CN106619643A (en) | 2017-05-10 |
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| CN201610994474.1A Pending CN106619643A (en) | 2016-11-11 | 2016-11-11 | Pharmaceutical composition containing ibrutinib |
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Cited By (4)
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| US9828383B1 (en) | 2012-06-04 | 2017-11-28 | Pharmacyclic s LLC | Crystalline forms of a bruton's tyrosine kinase inhibitor |
| US20180028537A1 (en) | 2014-08-07 | 2018-02-01 | Pharmacyclics Llc | Novel Formulations of a Bruton's Tyrosine Kinase Inhibitor |
| US10010507B1 (en) | 2015-03-03 | 2018-07-03 | Pharmacyclics Llc | Pharmaceutical formulations of a bruton's tyrosine kinase inhibitor |
| CN111110641A (en) * | 2018-10-31 | 2020-05-08 | 长春海悦药业股份有限公司 | Levofloxacin tablet composition and preparation method thereof |
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| WO2015071432A1 (en) * | 2013-11-14 | 2015-05-21 | Sandoz Ag | Pharmaceutical compositions of ibrutinib |
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10294231B2 (en) | 2012-06-04 | 2019-05-21 | Pharmacyclics Llc | Crystalline forms of a Bruton's tyrosine kinase inhibitor |
| US10294232B2 (en) | 2012-06-04 | 2019-05-21 | Pharmacyclics Llc | Crystalline forms of a Bruton's tyrosine kinase inhibitor |
| US10961251B1 (en) | 2012-06-04 | 2021-03-30 | Pharmacyclics Llc | Crystalline forms of a Bruton's tyrosine kinase inhibitor |
| US10065968B2 (en) | 2012-06-04 | 2018-09-04 | Pharmacyclics Llc | Crystalline forms of a bruton's tyrosine kinase inhibitor |
| US10106548B2 (en) | 2012-06-04 | 2018-10-23 | Pharmacyclics Llc | Crystalline forms of a Bruton's tyrosine kinase inhibitor |
| US10125140B1 (en) | 2012-06-04 | 2018-11-13 | Pharmacyclics Llc | Crystalline forms of a bruton's tyrosine kinase inhibitor |
| US10752634B2 (en) | 2012-06-04 | 2020-08-25 | Pharmacyclics Llc | Crystalline forms of a brutons tyrosine kinase inhibitor |
| US10266540B2 (en) | 2012-06-04 | 2019-04-23 | Pharmacyclics Llc | Crystalline forms of a Bruton's tyrosine kinase inhibitor |
| US9828383B1 (en) | 2012-06-04 | 2017-11-28 | Pharmacyclic s LLC | Crystalline forms of a bruton's tyrosine kinase inhibitor |
| US20180028537A1 (en) | 2014-08-07 | 2018-02-01 | Pharmacyclics Llc | Novel Formulations of a Bruton's Tyrosine Kinase Inhibitor |
| US10213386B2 (en) | 2015-03-03 | 2019-02-26 | Pharmacyclics Llc | Pharmaceutical formulations of a Bruton's tyrosine kinase inhibitor |
| US10828259B2 (en) | 2015-03-03 | 2020-11-10 | Pharmacyclics Llc | Pharmaceutical formulations of a Bruton's tyrosine kinase inhibitor |
| US10010507B1 (en) | 2015-03-03 | 2018-07-03 | Pharmacyclics Llc | Pharmaceutical formulations of a bruton's tyrosine kinase inhibitor |
| CN111110641A (en) * | 2018-10-31 | 2020-05-08 | 长春海悦药业股份有限公司 | Levofloxacin tablet composition and preparation method thereof |
| CN111110641B (en) * | 2018-10-31 | 2022-03-01 | 长春海悦药业股份有限公司 | Levofloxacin tablet composition and preparation method thereof |
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Application publication date: 20170510 |
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