JP2016539953A5 - - Google Patents
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- Publication number
- JP2016539953A5 JP2016539953A5 JP2016536250A JP2016536250A JP2016539953A5 JP 2016539953 A5 JP2016539953 A5 JP 2016539953A5 JP 2016536250 A JP2016536250 A JP 2016536250A JP 2016536250 A JP2016536250 A JP 2016536250A JP 2016539953 A5 JP2016539953 A5 JP 2016539953A5
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- acid
- microparticles
- nanoparticles
- poly
- 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
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- 238000000034 method Methods 0.000 claims 17
- 239000002904 solvent Substances 0.000 claims 10
- 239000011859 microparticle Substances 0.000 claims 9
- 239000002105 nanoparticle Substances 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 229940124597 therapeutic agent Drugs 0.000 claims 7
- 239000004094 surface-active agent Substances 0.000 claims 6
- 239000011159 matrix material Substances 0.000 claims 5
- 229920000642 polymer Polymers 0.000 claims 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- 229920002678 cellulose Polymers 0.000 claims 4
- 229920001577 copolymer Polymers 0.000 claims 4
- 150000004676 glycans Chemical class 0.000 claims 4
- 125000005395 methacrylic acid group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 229920001282 polysaccharide Polymers 0.000 claims 4
- 239000005017 polysaccharide Substances 0.000 claims 4
- 150000003839 salts Chemical group 0.000 claims 4
- VSWBSWWIRNCQIJ-GJZGRUSLSA-N (R,R)-asenapine Chemical compound O1C2=CC=CC=C2[C@@H]2CN(C)C[C@H]2C2=CC(Cl)=CC=C21 VSWBSWWIRNCQIJ-GJZGRUSLSA-N 0.000 claims 3
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 claims 3
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims 3
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 3
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 3
- 229930012538 Paclitaxel Natural products 0.000 claims 3
- 150000001253 acrylic acids Chemical class 0.000 claims 3
- 229960004372 aripiprazole Drugs 0.000 claims 3
- 229960005245 asenapine Drugs 0.000 claims 3
- 229960005370 atorvastatin Drugs 0.000 claims 3
- 229920003086 cellulose ether Polymers 0.000 claims 3
- 239000011248 coating agent Substances 0.000 claims 3
- 238000000576 coating method Methods 0.000 claims 3
- 229960002866 duloxetine Drugs 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229960001592 paclitaxel Drugs 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- -1 propylcellulose Substances 0.000 claims 3
- 229960004431 quetiapine Drugs 0.000 claims 3
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims 3
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims 3
- 229960004622 raloxifene Drugs 0.000 claims 3
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims 3
- 229960000672 rosuvastatin Drugs 0.000 claims 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 3
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 2
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims 2
- 229920001661 Chitosan Polymers 0.000 claims 2
- 229920001287 Chondroitin sulfate Polymers 0.000 claims 2
- 229920002307 Dextran Polymers 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 229920002907 Guar gum Polymers 0.000 claims 2
- 229920001202 Inulin Polymers 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 229940072056 alginate Drugs 0.000 claims 2
- 235000010443 alginic acid Nutrition 0.000 claims 2
- 229920000615 alginic acid Polymers 0.000 claims 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims 2
- 229940045110 chitosan Drugs 0.000 claims 2
- 229940059329 chondroitin sulfate Drugs 0.000 claims 2
- 229960002086 dextran Drugs 0.000 claims 2
- 239000000665 guar gum Substances 0.000 claims 2
- 235000010417 guar gum Nutrition 0.000 claims 2
- 229960002154 guar gum Drugs 0.000 claims 2
- 229920002674 hyaluronan Polymers 0.000 claims 2
- 229960003160 hyaluronic acid Drugs 0.000 claims 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 2
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims 2
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims 2
- 229940029339 inulin Drugs 0.000 claims 2
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 claims 2
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 claims 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 229920001277 pectin Polymers 0.000 claims 2
- 239000001814 pectin Substances 0.000 claims 2
- 235000010987 pectin Nutrition 0.000 claims 2
- 229960000292 pectin Drugs 0.000 claims 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims 1
- CTPDSKVQLSDPLC-UHFFFAOYSA-N 2-(oxolan-2-ylmethoxy)ethanol Chemical compound OCCOCC1CCCO1 CTPDSKVQLSDPLC-UHFFFAOYSA-N 0.000 claims 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 claims 1
- 108010006654 Bleomycin Proteins 0.000 claims 1
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims 1
- 239000002083 C09CA01 - Losartan Substances 0.000 claims 1
- 239000002080 C09CA02 - Eprosartan Substances 0.000 claims 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 claims 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 claims 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 claims 1
- 239000001856 Ethyl cellulose Substances 0.000 claims 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 claims 1
- ITIONVBQFUNVJV-UHFFFAOYSA-N Etomidoline Chemical compound C12=CC=CC=C2C(=O)N(CC)C1NC(C=C1)=CC=C1OCCN1CCCCC1 ITIONVBQFUNVJV-UHFFFAOYSA-N 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 1
- 102000051325 Glucagon Human genes 0.000 claims 1
- 108060003199 Glucagon Proteins 0.000 claims 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims 1
- 108010007859 Lisinopril Proteins 0.000 claims 1
- UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 claims 1
- 239000005480 Olmesartan Substances 0.000 claims 1
- IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 claims 1
- VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 claims 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims 1
- 102000002852 Vasopressins Human genes 0.000 claims 1
- 108010004977 Vasopressins Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 229960002669 albendazole Drugs 0.000 claims 1
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 claims 1
- 229960004343 alendronic acid Drugs 0.000 claims 1
- 229940009944 amidoline Drugs 0.000 claims 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims 1
- 229960001561 bleomycin Drugs 0.000 claims 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims 1
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| PCT/EP2014/076455 WO2015082562A1 (en) | 2013-12-05 | 2014-12-03 | Process for the production of drug formulations for oral administration |
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| JP2016539953A JP2016539953A (ja) | 2016-12-22 |
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| WO2011006012A1 (en) | 2009-07-08 | 2011-01-13 | Charleston Laboratories Inc. | Pharmaceutical compositions |
| WO2016198113A1 (en) | 2015-06-11 | 2016-12-15 | Alrise Biosystems Gmbh | Process for the preparation of drug loaded microparticles |
| US10736855B2 (en) | 2016-02-25 | 2020-08-11 | Dexcel Pharma Technologies Ltd. | Compositions comprising proton pump inhibitors |
| JP2019507181A (ja) | 2016-03-04 | 2019-03-14 | チャールストン ラボラトリーズ，インコーポレイテッド | 医薬組成物 |
| JP2019511249A (ja) * | 2016-03-31 | 2019-04-25 | トゥッティフーディ・ベスローテン・フェンノートシャップ | 顆粒 |
| GB201609222D0 (en) | 2016-05-25 | 2016-07-06 | F2G Ltd | Pharmaceutical formulation |
| CA3047354A1 (en) | 2016-12-20 | 2018-06-28 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine and polysiloxane or polyisobutylene |
| CA3047451A1 (en) | 2016-12-20 | 2018-06-28 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
| CN110799180A (zh) | 2017-06-26 | 2020-02-14 | 罗曼治疗系统股份公司 | 含阿塞那平和硅氧烷丙烯酸杂化聚合物的经皮治疗系统 |
| TR201719919A2 (tr) * | 2017-12-08 | 2019-06-21 | Sanovel Ilac Sanayi Ve Ticaret Anonim Sirketi | The pharmaceutical combination comprising raloxifene and aripiprazole |
| KR102066402B1 (ko) * | 2017-12-22 | 2020-01-15 | 대화제약 주식회사 | 이리노테칸 또는 그의 약제학적으로 허용가능한 염을 포함하는 경구투여용 약제학적 조성물 |
| US12329862B2 (en) | 2018-06-20 | 2025-06-17 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
| BR112020026099A2 (pt) | 2018-06-20 | 2021-03-23 | Lts Lohmann Therapie-Systeme Ag | sistema terapêutico transdérmico que contém asenapina |
| CN108938588B (zh) * | 2018-08-16 | 2021-06-22 | 广州维奥康药业科技有限公司 | 一种依折麦布片 |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
| KR102185475B1 (ko) * | 2019-06-20 | 2020-12-02 | 대화제약 주식회사 | 이리노테칸 자유 염기를 포함하는 경구투여용 약학 조성물 |
| US11819576B2 (en) | 2019-10-31 | 2023-11-21 | Evonik Operations Gmbh | Process for preparing nano-or microparticles comprising a carrier-polymer and one or more biologically active ingredients |
| WO2022033743A1 (en) | 2020-08-14 | 2022-02-17 | Re-Organic As | Method to disperse nano-cellulose in polymers, and derived products |
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| US5102668A (en) * | 1990-10-05 | 1992-04-07 | Kingaform Technology, Inc. | Sustained release pharmaceutical preparation using diffusion barriers whose permeabilities change in response to changing pH |
| US5650173A (en) * | 1993-11-19 | 1997-07-22 | Alkermes Controlled Therapeutics Inc. Ii | Preparation of biodegradable microparticles containing a biologically active agent |
| US5792477A (en) * | 1996-05-07 | 1998-08-11 | Alkermes Controlled Therapeutics, Inc. Ii | Preparation of extended shelf-life biodegradable, biocompatible microparticles containing a biologically active agent |
| US6350786B1 (en) * | 1998-09-22 | 2002-02-26 | Hoffmann-La Roche Inc. | Stable complexes of poorly soluble compounds in ionic polymers |
| ES2310164T3 (es) * | 1999-02-10 | 2009-01-01 | Pfizer Products Inc. | Dispositivo de liberacion controlada por la matriz. |
| US7838037B2 (en) * | 1999-11-17 | 2010-11-23 | Tagra Biotechnologies Ltd. | Method of microencapsulation |
| US6824822B2 (en) * | 2001-08-31 | 2004-11-30 | Alkermes Controlled Therapeutics Inc. Ii | Residual solvent extraction method and microparticles produced thereby |
| AU2002232824A1 (en) * | 2000-12-21 | 2002-07-01 | Inhale Therapeutic Systems, Inc. | Induced phase transition method for the production of microparticles containing hydrophobic active agents |
| JP5123452B2 (ja) * | 2001-09-19 | 2013-01-23 | 帝三製薬株式会社 | 徐放性外用剤 |
| EP1469830A2 (en) * | 2002-02-01 | 2004-10-27 | Pfizer Products Inc. | Method for making homogeneous spray-dried solid amorphous drug dispersions using pressure nozzles |
| EP1344520B1 (en) * | 2002-03-15 | 2007-10-03 | Alrise Biosystems GmbH | Microparticles and method for their production |
| KR20060033859A (ko) * | 2003-04-30 | 2006-04-20 | 데비오 팜 소시에떼 아노님 | 생식선 자극 호르몬 방출 호르몬을 이용한 방법 및 조성물 |
| WO2008075320A2 (en) * | 2006-12-21 | 2008-06-26 | Ranbaxy Laboratories Limited | Antilipidemic pharmaceutical compositions and process for preparation thereof |
| EP2280711A1 (en) * | 2008-03-07 | 2011-02-09 | Pfizer Inc. | Methods, dosage forms, and kits for administering ziprasidone without food |
| JP4856752B2 (ja) * | 2009-11-30 | 2012-01-18 | ホソカワミクロン株式会社 | 薬物含有ナノ粒子の製造方法 |
| US8927619B2 (en) * | 2011-12-21 | 2015-01-06 | Jorg Thomas Wilken | Color-stabilized iodopropynyl butylcarbamate |
| CN102579362B (zh) * | 2012-02-23 | 2014-09-10 | 浙江工业大学 | 一种非洛地平缓释微球及其制备方法 |
| CN102579368B (zh) * | 2012-03-28 | 2013-07-10 | 广州万泽医药科技有限公司 | 美托洛尔缓释微球、缓释药用组合物及其制备方法 |
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2014
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- 2014-12-03 KR KR1020167013757A patent/KR20160093611A/ko not_active Withdrawn
- 2014-12-03 US US15/101,873 patent/US20160303102A1/en not_active Abandoned
- 2014-12-03 CA CA2928772A patent/CA2928772A1/en not_active Abandoned
- 2014-12-03 WO PCT/EP2014/076455 patent/WO2015082562A1/en not_active Ceased
- 2014-12-03 EP EP14808594.7A patent/EP3076951B1/en active Active
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