JP2018530610A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018530610A5 JP2018530610A5 JP2018537705A JP2018537705A JP2018530610A5 JP 2018530610 A5 JP2018530610 A5 JP 2018530610A5 JP 2018537705 A JP2018537705 A JP 2018537705A JP 2018537705 A JP2018537705 A JP 2018537705A JP 2018530610 A5 JP2018530610 A5 JP 2018530610A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pharmaceutical composition
- compound
- composition according
- pharmaceutically acceptable
- 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.)
- Granted
Links
- 239000008194 pharmaceutical composition Substances 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 35
- 229940125904 compound 1 Drugs 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 30
- 239000003463 adsorbent Substances 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229920002785 Croscarmellose sodium Polymers 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 15
- 239000000314 lubricant Substances 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000007884 disintegrant Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims description 11
- 239000000539 dimer Substances 0.000 claims description 11
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 10
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical group CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 claims description 9
- -1 hydroxy, methoxy Chemical group 0.000 claims description 9
- 239000006186 oral dosage form Substances 0.000 claims description 9
- 229940045902 sodium stearyl fumarate Drugs 0.000 claims description 9
- 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 8
- 239000000654 additive Substances 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 229960001681 croscarmellose sodium Drugs 0.000 claims description 8
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 claims description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 238000013112 stability test Methods 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 108010010803 Gelatin Proteins 0.000 claims description 4
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 claims description 4
- 229960005168 croscarmellose Drugs 0.000 claims description 4
- 229920000159 gelatin Polymers 0.000 claims description 4
- 239000008273 gelatin Substances 0.000 claims description 4
- 229940014259 gelatin Drugs 0.000 claims description 4
- 235000019322 gelatine Nutrition 0.000 claims description 4
- 235000011852 gelatine desserts Nutrition 0.000 claims description 4
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 229940049920 malate Drugs 0.000 claims description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 241000220479 Acacia Species 0.000 claims description 2
- 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 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- 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 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 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 claims description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 claims description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 239000000783 alginic acid Substances 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 229960001126 alginic acid Drugs 0.000 claims description 2
- 150000004781 alginic acids Chemical class 0.000 claims description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose 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-QUYVBRFLSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000001506 calcium phosphate Substances 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 229940105329 carboxymethylcellulose Drugs 0.000 claims description 2
- 239000002826 coolant Substances 0.000 claims description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 claims description 2
- 229940038472 dicalcium phosphate Drugs 0.000 claims description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000013355 food flavoring agent Nutrition 0.000 claims description 2
- 235000003599 food sweetener Nutrition 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 229940071676 hydroxypropylcellulose Drugs 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 229960001375 lactose Drugs 0.000 claims description 2
- 150000004701 malic acid derivatives Chemical class 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 229940069328 povidone Drugs 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 239000008109 sodium starch glycolate Substances 0.000 claims description 2
- 229940079832 sodium starch glycolate Drugs 0.000 claims description 2
- 229920003109 sodium starch glycolate Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 229960002920 sorbitol Drugs 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 229960004793 sucrose Drugs 0.000 claims description 2
- 239000003765 sweetening agent Substances 0.000 claims description 2
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- 229940081735 acetylcellulose Drugs 0.000 claims 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims 1
- 229920002301 cellulose acetate Polymers 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- 101000945318 Homo sapiens Calponin-1 Proteins 0.000 description 19
- 101000652736 Homo sapiens Transgelin Proteins 0.000 description 19
- 102100031013 Transgelin Human genes 0.000 description 19
- JJAHTWIKCUJRDK-UHFFFAOYSA-N succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate Chemical compound C1CC(CN2C(C=CC2=O)=O)CCC1C(=O)ON1C(=O)CCC1=O JJAHTWIKCUJRDK-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000002156 mixing Methods 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 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
- 229940078456 calcium stearate Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 229940068682 chewable tablet Drugs 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000007919 dispersible tablet Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940049654 glyceryl behenate Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 229940037627 magnesium lauryl sulfate Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- HBNDBUATLJAUQM-UHFFFAOYSA-L magnesium;dodecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O HBNDBUATLJAUQM-UHFFFAOYSA-L 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
- 229940042126 oral powder Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 238000009490 roller compaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940080350 sodium stearate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940033134 talc Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2015091536 | 2015-10-09 | ||
| CNPCT/CN2015/091536 | 2015-10-09 | ||
| PCT/CN2016/087857 WO2017059702A1 (en) | 2015-10-09 | 2016-06-30 | Pharmaceutical salts, physical forms, and compositions of pyrrolopyrimidine kinase inhibitors, and methods of making same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018530610A JP2018530610A (ja) | 2018-10-18 |
| JP2018530610A5 true JP2018530610A5 (https=) | 2019-07-11 |
| JP6889494B2 JP6889494B2 (ja) | 2021-06-18 |
Family
ID=58487279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018537705A Active JP6889494B2 (ja) | 2015-10-09 | 2016-06-30 | ピロロピリミジンキナーゼ阻害剤の薬学的塩、物理的形態、および組成物、ならびにそれらを作製する方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10533011B2 (https=) |
| EP (1) | EP3359159B1 (https=) |
| JP (1) | JP6889494B2 (https=) |
| KR (1) | KR20180067584A (https=) |
| CN (1) | CN107949388B (https=) |
| AR (1) | AR106301A1 (https=) |
| AU (1) | AU2016334141B2 (https=) |
| BR (1) | BR112018006939A2 (https=) |
| CA (1) | CA3001744C (https=) |
| MX (1) | MX2018004332A (https=) |
| RU (1) | RU2018115334A (https=) |
| TW (1) | TW201722431A (https=) |
| WO (1) | WO2017059702A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9034885B2 (en) | 2012-01-13 | 2015-05-19 | Acea Biosciences Inc. | EGFR modulators and uses thereof |
| CA2861010A1 (en) | 2012-01-13 | 2013-07-18 | Xiao Xu | Heterocyclic compounds and uses as anticancer agents |
| NZ715687A (en) | 2013-07-11 | 2019-04-26 | Acea Biosciences Inc | Pyrimidine derivatives as kinase inhibitors |
| KR20180067584A (ko) | 2015-10-09 | 2018-06-20 | 아세아 테라퓨틱스 인코포레이티드 | 피롤로피리미딘 키나아제 억제제의 약학적 염, 물리적 형태 및 조성물, 및 이들의 제조 방법 |
| WO2018049214A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
| AU2017408099A1 (en) | 2017-04-07 | 2019-11-07 | ACEA Therapeutics, Inc. | Pharmaceutical salts, physical forms, and compositions of pyrrolopyrimidine kinase inhibitors, and methods of making same |
| MA53388A (fr) | 2018-07-25 | 2021-06-02 | Novartis Ag | Inhibiteurs d'inflammasome nlrp3 |
| JP7675647B2 (ja) * | 2018-08-09 | 2025-05-13 | エイシア セラピューティクス， インコーポレイテッド | （ｓ）－ｎ－（３－（（２－（（４－（（１－アセチルピロリジン－３－イル）（メチル）アミノ）フェニル）アミノ）－５－メトキシピリミジン－４－イル）オキシ）フェニル）アクリルアミドの製造のためのプロセスおよびその製剤 |
| UY38687A (es) | 2019-05-17 | 2023-05-15 | Novartis Ag | Inhibidores del inflamasoma nlrp3, composiciones, combinaciones de los mismos y métodos para su uso |
| CN110407840A (zh) * | 2019-08-15 | 2019-11-05 | 重庆化工职业学院 | 一种艾维替尼的制备方法 |
| MX2023001725A (es) | 2020-08-14 | 2023-02-22 | Novartis Ag | Derivados de espiropiperidinilo sustituidos con heteroarilo y usos farmaceuticos de los mismos. |
| CN111848631B (zh) * | 2020-08-28 | 2022-04-19 | 四川大学华西医院 | 一种靶向EGFR突变的吡咯并[2,3-d]嘧啶衍生物及其制备方法和用途 |
| CN114573591B (zh) * | 2022-04-16 | 2023-04-25 | 成都施贝康生物医药科技有限公司 | 一种取代的吡咯并嘧啶化合物及其应用 |
| UY40374A (es) | 2022-08-03 | 2024-02-15 | Novartis Ag | Inhibidores de inflamasoma nlrp3 |
| WO2024092047A1 (en) | 2022-10-26 | 2024-05-02 | Sorrento Therapeutics, Inc. | Administration of pyrrolopyrimidine-based kinase inhibitors for treatment of psoriasis |
| CN120737091B (zh) * | 2025-08-29 | 2025-11-04 | 四川大学华西医院 | 一种以7-脱氮鸟嘌呤为骨架的化合物、药物组合物及用途 |
Family Cites Families (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3974277A (en) | 1974-09-06 | 1976-08-10 | Diamond Shamrock Corporation | 2-[2-(5-Nitro-2-furyl)vinyl]-4-(anilino)quinazolines as growth promotants and feed efficiency enhancing agents |
| EP1230225A2 (en) | 1999-11-01 | 2002-08-14 | Eli Lilly And Company | Pharmaceutically active 4-substituted pyrimidine derivatives |
| EP1369418B1 (en) | 2001-02-21 | 2010-07-28 | Mitsubishi Tanabe Pharma Corporation | Quinazoline derivatives |
| US6881737B2 (en) | 2001-04-11 | 2005-04-19 | Amgen Inc. | Substituted triazinyl acrylamide derivatives and methods of use |
| WO2003026664A1 (en) | 2001-09-26 | 2003-04-03 | Bayer Corporation | 2-phenylamino-4- (5-pyrazolylamino) -pyramidine derivatives as kinase inhibitors, in particular, src kinase inhibitors |
| US7732127B2 (en) | 2002-12-20 | 2010-06-08 | Acea Biosciences, Inc. | Dynamic monitoring of cell adhesion and spreading using the RT-CES system |
| US7192752B2 (en) | 2002-12-20 | 2007-03-20 | Acea Biosciences | Real time electronic cell sensing systems and applications for cell-based assays |
| US7468255B2 (en) | 2002-12-20 | 2008-12-23 | Acea Biosciences | Method for assaying for natural killer, cytotoxic T-lymphocyte and neutrophil-mediated killing of target cells using real-time microelectronic cell sensing technology |
| US7560269B2 (en) | 2002-12-20 | 2009-07-14 | Acea Biosciences, Inc. | Real time electronic cell sensing system and applications for cytotoxicity profiling and compound assays |
| WO2004010102A2 (en) | 2002-07-20 | 2004-01-29 | Acea Biosciences, Inc. | Impedance based apparatuses and methods for analyzing cells and particles |
| US7470533B2 (en) | 2002-12-20 | 2008-12-30 | Acea Biosciences | Impedance based devices and methods for use in assays |
| AU2003265636A1 (en) | 2002-09-06 | 2004-03-29 | Smithkline Beecham Corporation | Pyrrolo(2, 3-d)pyrimidine-4-yl and purin-6-yl urea compounds |
| TW200416034A (en) * | 2002-11-15 | 2004-09-01 | Mitsubishi Pharma Corp | Medicinal composition |
| CA2550361C (en) | 2003-12-19 | 2014-04-29 | Prabha Ibrahim | Compounds and methods for development of ret modulators |
| WO2005065156A2 (en) | 2003-12-23 | 2005-07-21 | First Data Corporation | Global positioning system |
| JP2007526339A (ja) | 2004-03-02 | 2007-09-13 | ニューロジェン・コーポレーション | アリール置換プリン類縁体 |
| CA2570817A1 (en) | 2004-06-17 | 2006-01-26 | Plexxikon, Inc. | Azaindoles modulating c-kit activity and uses therefor |
| CA2572331A1 (en) | 2004-07-02 | 2006-02-09 | Exelixis, Inc. | C-met modulators and method of use |
| BRPI0617167B8 (pt) | 2005-09-21 | 2021-05-25 | Nycomed Gmbh | sulfonilpirróis como inibidores de hdac's, seu uso, composição farmacêutica e combinação |
| WO2007042298A1 (en) | 2005-10-13 | 2007-04-19 | Glaxo Group Limited | Pyrrolopyrimidine derivatives as syk inhibitors |
| KR100832593B1 (ko) | 2005-11-08 | 2008-05-27 | 한미약품 주식회사 | 신호전달 저해제로서의 퀴나졸린 유도체 및 이의 제조방법 |
| GB0526246D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| CA2644494A1 (en) | 2006-03-03 | 2007-09-13 | Aveo Pharmaceuticals, Inc. | Processes for synthesizing 7-alkynyl-4-aminoquinazolines and a related intermediate |
| CA2647543A1 (en) | 2006-03-29 | 2007-11-08 | Foldrx Pharmaceuticals, Inc. | Inhibition of alpha-synuclein toxicity |
| WO2008039359A2 (en) | 2006-09-25 | 2008-04-03 | Janssen Pharmaceutica N.V. | Bicyclic pyrimidine kinase inhibitors |
| BRPI0720264B1 (pt) | 2006-12-08 | 2022-03-03 | Novartis Ag | Compostos e composições como inibidores de proteína cinase |
| CN101622001A (zh) | 2007-01-26 | 2010-01-06 | Irm责任有限公司 | 作为激酶抑制剂用于治疗疟原虫相关疾病的嘌呤化合物和组合物 |
| US8846704B2 (en) | 2007-01-31 | 2014-09-30 | YM Biosciences Austraila Pty Ltd | Thiopyrimidine-based compounds and uses thereof |
| SI2167033T1 (sl) | 2007-05-30 | 2017-08-31 | Veloxis Pharmaceuticals A/S | Odmerna oblika, ki obsega takrolimus, za dajanje enkrat na dan |
| TWI377944B (en) | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| WO2009017838A2 (en) | 2007-08-01 | 2009-02-05 | Exelixis, Inc. | Combinations of jak-2 inhibitors and other agents |
| US7981903B2 (en) | 2007-08-08 | 2011-07-19 | Glaxosmithkline Llc | 2-[2-{phenylamino}-1H-pyrrolo[2,3-D]pyrimidin-4-yl)amino] benzamide derivatives as IGF-1R inhibitors for the treatment of cancer |
| WO2009032703A1 (en) | 2007-08-28 | 2009-03-12 | Irm Llc | 2- (het) arylamino-6-aminopyridine derivatives and fused forms thereof as anaplastic lymphoma kinase inhibitors |
| CN105367503A (zh) | 2007-10-19 | 2016-03-02 | 阿维拉制药公司 | 杂芳基化合物和其用途 |
| US7989465B2 (en) | 2007-10-19 | 2011-08-02 | Avila Therapeutics, Inc. | 4,6-disubstituted pyrimidines useful as kinase inhibitors |
| NZ588830A (en) | 2008-04-22 | 2012-11-30 | Portola Pharm Inc | Inhibitors of protein kinases |
| PT2300013T (pt) | 2008-05-21 | 2017-10-31 | Ariad Pharma Inc | Derivados de fósforo como inibidores de cinases |
| US8338439B2 (en) | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| TWI546290B (zh) | 2008-06-27 | 2016-08-21 | 賽基艾維洛米斯研究股份有限公司 | 雜芳基化合物及其用途 |
| WO2010045451A1 (en) | 2008-10-16 | 2010-04-22 | Glaxosmithkline Llc | Pyrrolopyrimidine compounds |
| US20100204221A1 (en) | 2009-02-09 | 2010-08-12 | Hariprasad Vankayalapati | Pyrrolopyrimidinyl axl kinase inhibitors |
| KR101705158B1 (ko) | 2009-05-05 | 2017-02-09 | 다나-파버 캔서 인스티튜트 인크. | Ｅｇｆｒ 억제제 및 질환 치료방법 |
| US20110207736A1 (en) | 2009-12-23 | 2011-08-25 | Gatekeeper Pharmaceuticals, Inc. | Compounds that modulate egfr activity and methods for treating or preventing conditions therewith |
| US20130137709A1 (en) | 2010-05-05 | 2013-05-30 | Nathanael S. Gray | Compounds that modulate EGFR activity and methods for treating or preventing conditions therewith |
| PT2585470T (pt) | 2010-06-23 | 2017-03-06 | Hanmi Science Co Ltd | Novos derivados fundidos de pirimidina para inibição da actividade da tirosina cinase |
| EP2635285B1 (en) | 2010-11-01 | 2017-05-03 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| MX382354B (es) | 2010-11-01 | 2025-03-13 | Celgene Car Llc | Compuestos heterocíclicos y usos de los mismos. |
| JP5957003B2 (ja) | 2010-11-10 | 2016-07-27 | セルジーン アヴィロミクス リサーチ， インコーポレイテッド | 変異体選択的ｅｇｆｒ阻害剤およびその使用 |
| CN102583089B (zh) | 2011-01-11 | 2015-11-25 | 山东新北洋信息技术股份有限公司 | 薄片类介质处理装置 |
| JP2014511391A (ja) | 2011-03-07 | 2014-05-15 | フォンダッツィオーネ・テレソン | Ｔｆｅｂリン酸化阻害剤およびその使用 |
| EP2694486B1 (en) | 2011-04-01 | 2018-01-10 | University of Utah Research Foundation | Substituted n-(3-(pyrimidin-4-yl)phenyl)acrylamide analogs as tyrosine receptor kinase btk inhibitors |
| US9834518B2 (en) | 2011-05-04 | 2017-12-05 | Ariad Pharmaceuticals, Inc. | Compounds for inhibiting cell proliferation in EGFR-driven cancers |
| US8828391B2 (en) | 2011-05-17 | 2014-09-09 | Boehringer Ingelheim International Gmbh | Method for EGFR directed combination treatment of non-small cell lung cancer |
| CA2861010A1 (en) | 2012-01-13 | 2013-07-18 | Xiao Xu | Heterocyclic compounds and uses as anticancer agents |
| US9586965B2 (en) * | 2012-01-13 | 2017-03-07 | Acea Biosciences Inc. | Pyrrolo[2,3-d]pyrimidine compounds as inhibitors of protein kinases |
| US9464089B2 (en) | 2012-01-13 | 2016-10-11 | Acea Biosciences Inc. | Heterocyclic compounds and uses thereof |
| US9034885B2 (en) * | 2012-01-13 | 2015-05-19 | Acea Biosciences Inc. | EGFR modulators and uses thereof |
| JP6378171B2 (ja) * | 2012-04-24 | 2018-08-22 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ｄｎａ−ｐｋ阻害剤 |
| BR112015002709B1 (pt) * | 2012-08-06 | 2022-09-20 | Acea Biosciences Inc | Compostos, composição farmacêutica, uso dos mesmos e uso de uma combinação de composto ou composição farmacêutica e um segundo agente profilático ou agente terapêutico |
| NZ715687A (en) | 2013-07-11 | 2019-04-26 | Acea Biosciences Inc | Pyrimidine derivatives as kinase inhibitors |
| CN104306348B (zh) | 2014-09-30 | 2017-05-31 | 地奥集团成都药业股份有限公司 | 一种辛伐他汀片及其制备方法 |
| CN105185339B (zh) | 2015-10-08 | 2017-12-29 | 京东方科技集团股份有限公司 | 移位寄存器单元、栅线驱动装置以及驱动方法 |
| KR20180067584A (ko) | 2015-10-09 | 2018-06-20 | 아세아 테라퓨틱스 인코포레이티드 | 피롤로피리미딘 키나아제 억제제의 약학적 염, 물리적 형태 및 조성물, 및 이들의 제조 방법 |
| PL3377495T3 (pl) | 2015-11-16 | 2022-05-16 | Topadur Pharma Ag | Pochodne 2-fenylo-3,4-dihydropirolo[2,1-f] [1,2,4]triazynonu jako inhibitory fosfodiesterazy i ich zastosowania |
| AU2017408099A1 (en) | 2017-04-07 | 2019-11-07 | ACEA Therapeutics, Inc. | Pharmaceutical salts, physical forms, and compositions of pyrrolopyrimidine kinase inhibitors, and methods of making same |
-
2016
- 2016-06-30 KR KR1020187012886A patent/KR20180067584A/ko not_active Ceased
- 2016-06-30 EP EP16853009.5A patent/EP3359159B1/en active Active
- 2016-06-30 RU RU2018115334A patent/RU2018115334A/ru not_active Application Discontinuation
- 2016-06-30 BR BR112018006939-6A patent/BR112018006939A2/en not_active IP Right Cessation
- 2016-06-30 AU AU2016334141A patent/AU2016334141B2/en active Active
- 2016-06-30 US US15/766,736 patent/US10533011B2/en active Active
- 2016-06-30 CA CA3001744A patent/CA3001744C/en active Active
- 2016-06-30 MX MX2018004332A patent/MX2018004332A/es unknown
- 2016-06-30 CN CN201680021771.6A patent/CN107949388B/zh active Active
- 2016-06-30 JP JP2018537705A patent/JP6889494B2/ja active Active
- 2016-06-30 WO PCT/CN2016/087857 patent/WO2017059702A1/en not_active Ceased
- 2016-10-07 TW TW105132675A patent/TW201722431A/zh unknown
- 2016-10-07 AR ARP160103082A patent/AR106301A1/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018530610A5 (https=) | ||
| RU2018115334A (ru) | Фармацевтические соли, физические формы и композиции пирролопиримидиновых ингибиторов киназ, и способы их получения | |
| AU2022259767B2 (en) | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof | |
| US11007152B2 (en) | Pharmaceutical composition comprising amorphous lenalidomide and an antioxidant | |
| JP2023062189A (ja) | 癌を処置する方法 | |
| JP2018154596A (ja) | アジルサルタン含有固形医薬組成物 | |
| US10588892B2 (en) | Pharmaceutical composition comprising sacubitril and valsartan | |
| WO2012140604A1 (en) | Stable formulations of pramipexole hydrochloride | |
| RU2016106336A (ru) | Противотуберкулезная композиция, содержащая рифампицин, изониазид, этамбутол и пиразинамид, и способ ее получения | |
| AU2017254950B2 (en) | Solid oral formulations and crystalline forms of an inhibitor of apoptosis protein | |
| WO2020003196A1 (en) | Pharmaceutical composition of axitinib | |
| US10611772B2 (en) | Crystalline form of Ribociclib succinate | |
| TR2023003669A1 (tr) | Empagliflozi̇n i̇çeren kati bi̇r di̇spersi̇yonun bi̇r tablet formülasyonu | |
| JP2016216425A (ja) | カルベジロール含有錠剤 | |
| TR2023003672A1 (tr) | Empagli̇flozi̇n i̇çeren fi̇lm kapli tabletler | |
| TR2023002079A2 (tr) | Empagli̇flozi̇n i̇çeren bi̇r fi̇lm kapli tablet | |
| WO2024115680A1 (en) | Ribociclib salts and formulations thereof | |
| TR2021001817A2 (tr) | Naltrekson hi̇droklorür i̇çeren bi̇r fi̇lm kapli tablet | |
| WO2016135740A1 (en) | Process for preparing stable oral compositions of everolimus | |
| HK40007684A (en) | Preparation containing benzimidazole derivative | |
| EP4442252A1 (en) | A tablet formulation of a solid dispersion comprising empagliflozin | |
| JP2026513056A (ja) | 新規トリメタジジン固相 | |
| EP4420658A1 (en) | A film coated tablet comprising empagliflozin | |
| HK40007684B (en) | Preparation containing benzimidazole derivative | |
| TR2023003670A2 (tr) | Empagli̇flozi̇n ve sürfaktan i̇çeren bi̇r fi̇lm kapli tablet |