CN106999483B - A kind of pharmaceutical composition containing quinoline or its salt - Google Patents
A kind of pharmaceutical composition containing quinoline or its salt Download PDFInfo
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- CN106999483B CN106999483B CN201680003848.7A CN201680003848A CN106999483B CN 106999483 B CN106999483 B CN 106999483B CN 201680003848 A CN201680003848 A CN 201680003848A CN 106999483 B CN106999483 B CN 106999483B
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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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
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- 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
- A61K47/02—Inorganic compounds
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- 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
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- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
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- Inorganic Chemistry (AREA)
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Abstract
A kind of pharmaceutical composition contains 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine or its pharmacologically acceptable salt；And basic amino acid or meglumine, and/or it is selected from least one of potassium carbonate, saleratus compound；And the composition does not contain microcrystalline cellulose.
Description
Technical field
The invention belongs to field of pharmaceutical preparations, and in particular to one kind contains quinoline 4- [3- chloro- 4- (cyclopropyl ammonia
Base carbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine or its salt pharmaceutical composition, the composition have dissolve out it is fast
Speed, the characteristics of having good stability.
Background technique
WO2002032872 discloses a kind of quinoline 4- [3- chloro- 4- (cyclopropylaminocarbonyl) aminobenzene oxygen
Base] -7- methoxyl group -6- quinoline formyl amine, it is known that it has other Angiogensis and carcinogenic letter for inhibiting to participate in tumor proliferation
Number access correlation RTK, additionally it is possible to which the kinase activity of selective depression vascular endothelial growth factor (VEGF) receptor clinically can be used
The treatment of the kinds of tumors such as Thyreoidine cancer, lung cancer, melanoma.
But by 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine
Or its pharmaceutically acceptable salt, when being prepared into pharmaceutical composition, under the conditions of wet, hot existing, drug is decomposed, simultaneously
Pharmaceutical composition moisture absorption, causes drug dissolution to decline.
Patent CN101001629A is disclosed containing 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- first
The composition of oxygroup -6- quinoline formyl amine or its pharmaceutically acceptable salt, is solved using alkaline inorganic compounds such as magnesia
The certainly degradation problem of drug, while solving the problems, such as that the dissolution rate of drug declines using silicic acids.But silicic acid class
Conjunction object dosage is larger, and silicic acids density is minimum, easily waves in production, causes the wound to operator's respiratory system
Evil.Simultaneously in mixed process, since its density differs larger with other auxiliary materials, it is likely to result in material and mixes non-uniform wind
Danger, causes difficulty to preparation industrialized production.
Summary of the invention
It has good stability the purpose of the present invention is to provide one kind while dissolving out rapid pharmaceutical composition, and the drug
Composition preparation process is simple, is more suitable for technology mass production.
Pharmaceutical composition provided by the invention includes active pharmaceutical ingredient and alkaline matter.Active pharmaceutical ingredient is 4- [3-
Chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine or its pharmacologically acceptable salt,
And the pharmaceutical composition is free of microcrystalline cellulose.
Alkaline matter includes the one or more of following substances:
(1) basic amino acid,
(2) meglumine,
(3) at least one of potassium carbonate or saleratus compound；
Wherein, basic amino acid is preferably selected from one or more of lysine, arginine and histidine.
In a preferred embodiment of the present invention, the alkaline matter is at least one of arginine or meglumine chemical combination
The mixture of object and at least one of potassium carbonate or saleratus compound.
In especially preferred embodiment of present invention, the alkaline matter is at least one of arginine or meglumine
The mixture of compound and saleratus.
In another preferred embodiment of the present invention, the alkaline matter is the mixing of arginine and meglumine
Object.
When alkaline matter of the invention is the mixture of two kinds of substances, the ratio of described two mixtures is not limited especially
System, in preferred embodiments, their weight ratio can between 1: 0.1 to 1: 10, between preferably 1: 0.5 to 1: 2,
Most preferably 1: 1.
The content of the alkaline matter is unrestricted, as long as raising dissolution can be played containing a small amount of above-mentioned alkaline matter,
Increase the effect of stability.For the convenience of preparation, in a preferred embodiment of the present invention, the content model of the alkaline matter
It encloses and can be the 0.5%-90% based on composition total weight；It is preferred that 1%-50%；More preferable 1-35%；Most preferably 5-20%.
In pharmaceutical composition of the invention, the pharmacologically acceptable salt of the active constituent can selected from hydrochloride,
Hydrobromate, tosilate, mesylate, sulfate or esilate.Total weight based on composition, it is described activity at
The content range divided can be the 0.5%-30% based on composition total weight；It is preferred that 1%-25%；Most preferably 1-15%.
Pharmaceutical composition provided by the invention can contain filler, for example, calcium monohydrogen phosphate, mannitol, pregelatinized starch,
Lactose etc. is one or more.Total weight based on composition, the filling agent content is about 5%~80%.
Pharmaceutical composition provided by the invention can contain disintegrating agent, wherein disintegrating agent be croscarmellose sodium,
One of sodium carboxymethyl starch, low-substituted hydroxypropyl cellulose and crospovidone are a variety of.Total weight based on composition,
The disintegrant content is about 1%~30%.
The present invention, which provides pharmaceutical composition, can contain adhesive, and described adhesive can be selected from hydroxypropyl methylcellulose, hydroxypropyl
Base cellulose, sodium carboxymethylcellulose, polyvinylpyrrolidone, methylcellulose etc. are one or more, based on the total of composition
Weight, described adhesive content are about 0.5~15%.
Pharmaceutical composition provided by the invention also may include one or more lubricants, facilitate filling capsule or tabletting.
Lubricant can be selected from talcum powder, magnesium stearate, zinc stearate, Compritol 888 ATO, NaLS, hydrogenated vegetable oil, glue
Body silica etc..Total weight based on composition, the content of the lubricant are about 0.5%~5%
In a preferred embodiment of the present invention, the composition consists of the following compositions:
(1) 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine or its medicine
Acceptable salt in Neo-Confucianism；
(2) alkaline matter；
(3) filler；
(4) disintegrating agent；
(5) adhesive
(6) lubricant.
In highly preferred embodiment, the composition following component composition:
(1) 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine or its medicine
Acceptable salt in Neo-Confucianism；
(2) arginine, 5~20%；
(3) saleratus, 10~40%；
(4) mannitol, 30%~60%；
(5) low-substituted hydroxypropyl cellulose, 1%~10%；
(6) hydroxypropyl cellulose, 1%~5%；
(7) talcum powder, 1%~5%.
Pharmaceutical composition of the invention can be prepared using the common method in this field, such as bulk drug of pretreatment adds with interior pelletizes, is dry
The methods of method granulation, one-step palletizing prepare medicament composition granule, and then filling capsule, prepares hard capsule.
Pharmaceutical composition provided by the invention without microcrystalline cellulose has higher stability, reduces new impurity
Generation, and have good dissolving out capability.
Detailed description of the invention
Fig. 1 shows dissolution curve of the capsule of embodiment 1 to 3 in 0.1mol/L hydrochloric acid solution.
Fig. 2 shows dissolution curve of the capsule of embodiment 4 to 6 in 0.1mol/L hydrochloric acid solution.
Fig. 3 shows dissolution curve of the capsule of comparative example 1 to comparative example 3 in 0.1mol/L hydrochloric acid solution.
Fig. 4 show embodiment 3 capsule and 40 DEG C of temperature, relative humidity 75% place after in 0.1mol/L hydrochloric acid solution
In dissolution curve.
Fig. 5 show embodiment 6 capsule and 40 DEG C of temperature, relative humidity 75% place after in 0.1mol/L hydrochloric acid solution
In dissolution curve.
Fig. 6 show comparative example 1 capsule and 40 DEG C of temperature, relative humidity 75% place after in 0.1mol/L hydrochloric acid solution
In dissolution curve.
Fig. 7 show comparative example 2 capsule and 40 DEG C of temperature, relative humidity 75% place after in 0.1mol/L hydrochloric acid solution
In dissolution curve.
Fig. 8 show comparative example 3 capsule and 40 DEG C of temperature, relative humidity 75% place after in 0.1mol/L hydrochloric acid solution
In dissolution curve.
Specific embodiment
By following embodiment and experimental example, present invention be described in more detail.These embodiments and experimental example are only used for
Bright property purpose, and the range being not intended to restrict the invention.
Examples 1 to 3
By the methanesulfonic acid of 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine
Salt (hereinafter referred to as compound A), arginine, saleratus, PEARLITOL 25C, hydroxypropyl cellulose, low substituted hydroxy-propyl fiber
Element carries out wet granulation using high-shearing granulation machine in the ratio in table 1, using purified water as wetting agent, carries out to wet softwood
Dry particl (moisture is less than 2%) is then carried out dry whole grain, the talcum powder of recipe quantity is added, used by wet whole grain and drying process
Rotation total mix machine is mixed.The total mix granule filling capsule that will be obtained, prepares capsule.
Table 1
| Ingredient | Embodiment 1 | Embodiment 2 | Embodiment 3 |
| Compound A | 2.5 | 4.9 | 12.3 |
| Arginine | 10.0 | 10.0 | 10.0 |
| Saleratus | 20.0 | 20.0 | 20.0 |
| PEARLITOL 25C | 56.5 | 54.1 | 46.7 |
| Hydroxypropyl cellulose | 3.0 | 3.0 | 3.0 |
| Low-substituted hydroxypropyl cellulose | 5.0 | 5.0 | 5.0 |
| Talcum powder | 3.0 | 3.0 | 3.0 |
| It amounts to | 100 | 100 | 100 |
Unit: quality %
Embodiment 4~6
By the methanesulfonic acid of 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine
Salt (hereinafter referred to as compound A), arginine, potassium carbonate, PEARLITOL 25C, hydroxypropyl cellulose, low-substituted hydroxypropyl cellulose,
In the ratio in table 2, wet granulation is carried out using high-shearing granulation machine, using purified water as wetting agent, wet softwood is carried out wet
Dry particl (moisture is less than 2%) is then carried out dry whole grain, the talcum powder of recipe quantity is added, using rotation by whole grain and drying process
Turn total mix machine to be mixed.The total mix granule filling capsule that will be obtained, prepares capsule.
Table 2
| Ingredient | Embodiment 4 | Embodiment 5 | Embodiment 6 |
| Compound A | 2.5 | 4.9 | 12.3 |
| Arginine | 10.0 | 10.0 | 10.0 |
| Potassium carbonate | 20.0 | 20.0 | 20.0 |
| PEARLITOL 25C | 56.5 | 54.1 | 46.7 |
| Hydroxypropyl cellulose | 3.0 | 3.0 | 3.0 |
| Low-substituted hydroxypropyl cellulose | 5.0 | 5.0 | 5.0 |
| Talcum powder | 3.0 | 3.0 | 3.0 |
| It amounts to | 100 | 100 | 100 |
Unit: quality %
Comparative example 1~3
By the methanesulfonic acid of 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine
Salt (hereinafter referred to as compound A) arginine, saleratus or potassium carbonate, PEARLITOL 25C, microcrystalline cellulose, hydroxy propyl cellulose
Element, low-substituted hydroxypropyl cellulose are carried out wet granulation using high-shearing granulation machine, are with purified water in the ratio in table 3
Wetting agent carries out wet whole grain and drying process to wet softwood, and dry particl (moisture is less than 2%) is then carried out dry whole grain, is added
The talcum powder of recipe quantity is mixed using rotation total mix machine.The total mix granule filling capsule that will be obtained, prepares comparative example 1~3
Capsule.
Table 3
| Ingredient | Comparative example 1 | Comparative example 2 | Comparative example 3 |
| Compound A | 12.3 | 12.3 | 12.3 |
| Arginine | 0 | 10 | 10 |
| Potassium carbonate | 0 | 20 | 0 |
| Saleratus | 0 | 0 | 20 |
| PEARLITOL 25C | 43.7 | 13.7 | 13.7 |
| Microcrystalline cellulose | 33 | 33 | 33 |
| Hydroxypropyl cellulose | 3 | 3 | 3 |
| Low-substituted hydroxypropyl cellulose | 5 | 5 | 5 |
| Talcum powder | 3 | 3 | 3 |
| It amounts to | 100 | 100 | 100 |
Unit: quality %
Experimental example 1: dissolution experiment
According to 2010 editions two the second methods of annex dissolution determination (paddle method) of Chinese Pharmacopoeia, to the capsule of Examples 1 to 6
Carry out dissolution determination.Use the 0.1mol/L hydrochloric acid solution of 900ml as dissolution medium, and with 50rpm at 37 ± 0.5 DEG C
Paddle speed carry out dissolution test.The result shows that the glue of the Examples 1 to 6 containing arginine and potassium carbonate or saleratus in prescription
In wafer, compound A dissolution is complete rapidly.
Dissolution curve is shown in Fig. 1, Fig. 2.
Experimental example 2: dissolution experiment
According to 2010 editions two the second methods of annex dissolution determination (paddle method) of Chinese Pharmacopoeia, to the capsule of comparative example 1~3
Carry out dissolution determination.Use the 0.1mol/L hydrochloric acid solution of 900ml as dissolution medium, and with 50rpm at 37 ± 0.5 DEG C
Paddle speed carry out dissolution test.The result shows that being free of the comparative example 1 of basic auxiliary in prescription, compound A dissolution is slow；Prescription
In the comparative example 2 containing arginine, potassium carbonate or saleratus and comparative example 3 capsule in, compound A dissolution is complete rapidly
Entirely, illustrate that the addition of microcrystalline cellulose does not influence the dissolution of drug.
Dissolution curve is shown in Fig. 3.
Experimental example 3: stability study
The capsule of the capsule of embodiment 3,6 and comparative example 1~3 is placed in temperature using high density polyethylene packaging
40 DEG C, place 1 month, 2 months, 3 months, 6 months in the environment of relative humidity 75%, degradation product is then measured using HPLC method
Generation, it is molten to the sample measurement after placement using 2010 editions two the second methods of annex dissolution determination (paddle method) of Chinese Pharmacopoeia
Out-degree.
Degradation product measurement result shows embodiment 3 (containing arginine and saleratus), embodiment 6 (containing arginine and carbonic acid
Potassium) capsule in, degradation product does not increase, and comparative example 1 is free of basic auxiliary, and degradation product is obvious with the extension of standing time
Increase, comparative example 2 and comparative example 3 contain basic auxiliary and microcrystalline cellulose, place in the environment of 40 DEG C of temperature, relative humidity 75%
New impurity 1 is generated after 1 month, which obviously increases with the extension of standing time, other degradation products do not increase.(see
Table 4 to 8)
Dissolution results show embodiment 3 (containing arginine and saleratus), embodiment 6 (containing arginine and potassium carbonate)
Capsule in, the dissolution rate of compound A does not have with preliminary phase than still after placing in the environment of 40 DEG C of temperature, relative humidity 75%
It decreased significantly, dissolution is complete.In the capsule of comparative example 1 (no basic auxiliary), compound A initial stage in 40 DEG C of temperature, phase
To in the environment of humidity 75% place after dissolution it is incomplete, comparative example 2, comparative example 3 capsule in, compound A's is molten
Out-degree placed in the environment of 40 DEG C of temperature, relative humidity 75% after with preliminary phase ratio still without being decreased obviously, dissolution completely (see
Fig. 4 does not influence to dissolve out to the addition for 8), illustrating microcrystalline cellulose, but generates impurity 1.
Table 4
Table 5
Table 6
Table 7
Table 8
Claims (23)
1. a kind of pharmaceutical composition contains 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline
Quinoline formamide or its pharmacologically acceptable salt and alkaline matter, the alkaline matter are selected from:
Arginine and the mixture for being selected from one of potassium carbonate or saleratus compound, weight ratio 1:0.5-1:2；
Wherein, the composition is free of microcrystalline cellulose, and the content of the alkaline matter is the 1%- based on composition total weight
50%.
2. pharmaceutical composition according to claim 1, wherein the content of the alkaline matter is based on composition total weight
Count 1-35%.
3. pharmaceutical composition according to claim 2, wherein the content of the alkaline matter is based on composition total weight
Count 5-20%.
4. pharmaceutical composition according to claim 1, wherein containing disintegrating agent.
5. pharmaceutical composition according to claim 4, wherein disintegrating agent is croscarmellose sodium, carboxymethyl starch
One of sodium, low-substituted hydroxypropyl cellulose and crospovidone are a variety of.
6. pharmaceutical composition according to claim 1, the composition is by as follows at being grouped as:
1) 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine or its pharmacologically
Acceptable salt；
2) alkaline matter；
3) filler；
4) disintegrating agent；
5) adhesive
6) lubricant.
7. pharmaceutical composition according to claim 6, wherein the filler is selected from calcium monohydrogen phosphate, mannitol, pregelatinated
One of starch, lactose are a variety of.
8. pharmaceutical composition according to claim 6, wherein the filler content is 5% based on composition total weight
~80%.
9. pharmaceutical composition according to claim 8, wherein the filler content is based on composition total weight
30%~60%.
10. pharmaceutical composition according to claim 6, wherein the disintegrating agent is selected from croscarmellose sodium, carboxylic
One of methyl starch sodium, low-substituted hydroxypropyl cellulose and crospovidone are a variety of.
11. pharmaceutical composition according to claim 6, wherein the disintegrant content is the total weight based on composition
1%~30%.
12. pharmaceutical composition according to claim 11, wherein the disintegrant content is 1%~10%.
13. pharmaceutical composition according to claim 6, wherein it is fine to be selected from hydroxypropyl methylcellulose, hydroxypropyl for described adhesive
Tie up one of element, sodium carboxymethylcellulose, polyvinylpyrrolidone, methylcellulose or a variety of.
14. pharmaceutical composition according to claim 6, wherein described adhesive content is the total weight based on composition
0.5~15%.
15. pharmaceutical composition according to claim 14, wherein described adhesive content is the total weight based on composition
Meter 1%~5%.
16. pharmaceutical composition according to claim 6, wherein the lubricant is selected from talcum powder, magnesium stearate, stearic acid
One of zinc, Compritol 888 ATO, NaLS, hydrogenated vegetable oil, colloidal silicon dioxide are a variety of.
17. pharmaceutical composition according to claim 6, wherein the lubricant content is the total weight based on composition
0.5%~5%.
18. pharmaceutical composition according to claim 17, wherein the lubricant content is the total weight based on composition
Count more preferable 1%~5%.
19. pharmaceutical composition according to claim 6, it is characterised in that consist of the following compositions:
1) 4- [3- chloro- 4- (cyclopropylaminocarbonyl) amino-benzene oxygen] -7- methoxyl group -6- quinoline formyl amine or its pharmacologically
Acceptable salt；
2) arginine, 5~20%；
3) saleratus, 10~40%；
4) mannitol, 30%~60%；
5) low-substituted hydroxypropyl cellulose, 1%~10%；
6) hydroxypropyl cellulose, 1%~5%；
7) talcum powder, 1%~5%.
20. pharmaceutical composition according to claim 1, wherein pharmacologically acceptable salt is selected from hydrochloride, hydrobromic acid
Salt, tosilate, mesylate, sulfate or esilate.
21. pharmaceutical composition according to claim 20, wherein pharmacologically acceptable salt is mesylate.
22. purposes of the pharmaceutical composition described in any one of claim 1 to 21 in the drug of preparation treating cancer.
23. purposes according to claim 22, wherein the cancer is selected from thyroid cancer, lung cancer or melanoma.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2015105061612 | 2015-08-17 | ||
| CN201510506161 | 2015-08-17 | ||
| PCT/CN2016/091717 WO2017028660A1 (en) | 2015-08-17 | 2016-07-26 | Pharmaceutical composition containing quinoline derivative or salt thereof |
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| Publication Number | Publication Date |
|---|---|
| CN106999483A CN106999483A (en) | 2017-08-01 |
| CN106999483B true CN106999483B (en) | 2019-05-03 |
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| CN201680003848.7A Active CN106999483B (en) | 2015-08-17 | 2016-07-26 | A kind of pharmaceutical composition containing quinoline or its salt |
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| Country | Link |
|---|---|
| CN (1) | CN106999483B (en) |
| TW (1) | TWI739756B (en) |
| WO (1) | WO2017028660A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3384901A1 (en) * | 2017-04-04 | 2018-10-10 | Synthon B.V. | Pharmaceutical composition comprising lenvatinib mesylate |
| US10583133B2 (en) | 2018-03-12 | 2020-03-10 | Shilpa Medicare Limited | Pharmaceutical compositions of lenvatinib |
| CN115397416B (en) * | 2020-05-09 | 2023-12-05 | 北京睿创康泰医药研究院有限公司 | Pharmaceutical composition containing molecular level of lenvatinib, preparation method and application thereof |
| EP4147689A1 (en) * | 2021-09-13 | 2023-03-15 | Lotus Pharmaceutical Co., Ltd. | Lenvatinib formulation |
| CN115068620A (en) * | 2022-07-20 | 2022-09-20 | 天津睿创康泰生物技术有限公司 | Pharmaceutical composition capable of reducing generation of arylamine impurities |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101001629A (en) * | 2004-09-17 | 2007-07-18 | 卫材R&D管理有限公司 | Medicinal composition |
| CN102470133A (en) * | 2009-08-19 | 2012-05-23 | 卫材R&D管理有限公司 | Quinoline derivative-containing pharmaceutical composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004101526A1 (en) * | 2003-04-22 | 2004-11-25 | Eisai Co., Ltd. | Polymorphous crystal of 4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-qunolinecarboxamide and method for preparation thereof |
| CN101316590B (en) * | 2005-11-07 | 2011-08-03 | 卫材R&D管理有限公司 | Use of combination of anti-angiogenic substance and c-kit kinase inhibitor |
| TWI501950B (en) * | 2011-02-09 | 2015-10-01 | Eisai R&D Man Co Ltd | Pharmaceutical composition comprising quinoline derivative |
-
2016
- 2016-07-26 WO PCT/CN2016/091717 patent/WO2017028660A1/en active Application Filing
- 2016-07-26 CN CN201680003848.7A patent/CN106999483B/en active Active
- 2016-08-10 TW TW105125414A patent/TWI739756B/en active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101001629A (en) * | 2004-09-17 | 2007-07-18 | 卫材R&D管理有限公司 | Medicinal composition |
| CN102470133A (en) * | 2009-08-19 | 2012-05-23 | 卫材R&D管理有限公司 | Quinoline derivative-containing pharmaceutical composition |
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| Publication number | Publication date |
|---|---|
| WO2017028660A1 (en) | 2017-02-23 |
| TWI739756B (en) | 2021-09-21 |
| TW201707702A (en) | 2017-03-01 |
| CN106999483A (en) | 2017-08-01 |
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