NO328651B1 - Syreaddisjonssalter av et hydropyridinderivat, medikamenter som inneholder disse, anvendelse av saltene til fremstilling av medikamenter og fremgangsmate for fremstilling av syreaddisjonssaltene av hydropyridinderivatet - Google Patents
Syreaddisjonssalter av et hydropyridinderivat, medikamenter som inneholder disse, anvendelse av saltene til fremstilling av medikamenter og fremgangsmate for fremstilling av syreaddisjonssaltene av hydropyridinderivatet Download PDFInfo
- Publication number
- NO328651B1 NO328651B1 NO20030022A NO20030022A NO328651B1 NO 328651 B1 NO328651 B1 NO 328651B1 NO 20030022 A NO20030022 A NO 20030022A NO 20030022 A NO20030022 A NO 20030022A NO 328651 B1 NO328651 B1 NO 328651B1
- Authority
- NO
- Norway
- Prior art keywords
- fluorobenzyl
- acetoxy
- tetrahydrothieno
- pyridine
- cyclopropylcarbonyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 31
- 239000003814 drug Substances 0.000 title claims abstract description 27
- 239000002253 acid Substances 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 26
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 25
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 15
- 208000005189 Embolism Diseases 0.000 claims abstract description 9
- 201000010099 disease Diseases 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 70
- 239000013078 crystal Substances 0.000 claims description 41
- DTGLZDAWLRGWQN-UHFFFAOYSA-N prasugrel Chemical class C1CC=2SC(OC(=O)C)=CC=2CN1C(C=1C(=CC=CC=1)F)C(=O)C1CC1 DTGLZDAWLRGWQN-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 16
- JALHGCPDPSNJNY-UHFFFAOYSA-N [5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-6,7-dihydro-4h-thieno[3,2-c]pyridin-2-yl] acetate;hydron;chloride Chemical group Cl.C1CC=2SC(OC(=O)C)=CC=2CN1C(C=1C(=CC=CC=1)F)C(=O)C1CC1 JALHGCPDPSNJNY-UHFFFAOYSA-N 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000011976 maleic acid Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- YFTPSWAPYMNPMX-BTJKTKAUSA-N (z)-but-2-enedioic acid;[5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-6,7-dihydro-4h-thieno[3,2-c]pyridin-2-yl] acetate Chemical group OC(=O)\C=C/C(O)=O.C1CC=2SC(OC(=O)C)=CC=2CN1C(C=1C(=CC=CC=1)F)C(=O)C1CC1 YFTPSWAPYMNPMX-BTJKTKAUSA-N 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 230000010102 embolization Effects 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 20
- 229940124597 therapeutic agent Drugs 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 8
- 230000002401 inhibitory effect Effects 0.000 abstract description 8
- 238000003860 storage Methods 0.000 abstract description 5
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 230000003449 preventive effect Effects 0.000 abstract 2
- WJFYLCXWEXZNHU-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-b]pyridine Chemical class N1C=CC=C2SCCC21 WJFYLCXWEXZNHU-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 241000282472 Canis lupus familiaris Species 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical class CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 239000008280 blood Substances 0.000 description 8
- 210000001772 blood platelet Anatomy 0.000 description 8
- 239000001913 cellulose Substances 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 210000002381 plasma Anatomy 0.000 description 7
- 230000000069 prophylactic effect Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 5
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000007903 gelatin capsule Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920000881 Modified starch Polymers 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 235000019426 modified starch Nutrition 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 230000036470 plasma concentration Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- -1 polyoxyethylene Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 3
- DWBGTJUQWKWYGB-UHFFFAOYSA-N 1-cyclopropyl-2-(2-fluorophenyl)ethanone Chemical compound FC1=CC=CC=C1CC(=O)C1CC1 DWBGTJUQWKWYGB-UHFFFAOYSA-N 0.000 description 2
- LMCZCCDXOZGIND-UHFFFAOYSA-N 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone Chemical compound FC1=CC=CC=C1C(Br)C(=O)C1CC1 LMCZCCDXOZGIND-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical compound CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000007902 hard capsule Substances 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 210000004731 jugular vein Anatomy 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 229940125670 thienopyridine Drugs 0.000 description 2
- 239000002175 thienopyridine Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FFWQLZFIMNTUCZ-UHFFFAOYSA-N 1-(bromomethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CBr FFWQLZFIMNTUCZ-UHFFFAOYSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 239000004287 Dehydroacetic acid Substances 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004373 Pullulan Substances 0.000 description 1
- 229920001218 Pullulan Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 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 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- DHUYBTBFCQGDRP-UHFFFAOYSA-N [5-[[6-(cyclopropanecarbonyl)-6-fluorocyclohexa-2,4-dien-1-yl]methyl]-6,7-dihydro-4H-thieno[3,2-c]pyridin-2-yl] acetate Chemical compound C1CC=2SC(OC(=O)C)=CC=2CN1CC1C=CC=CC1(F)C(=O)C1CC1 DHUYBTBFCQGDRP-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229940013361 cresol Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- AUQDITHEDVOTCU-UHFFFAOYSA-N cyclopropyl cyanide Chemical compound N#CC1CC1 AUQDITHEDVOTCU-UHFFFAOYSA-N 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000008011 inorganic excipient Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229940037627 magnesium lauryl sulfate Drugs 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
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- IHZQFSMUJTTZOK-UHFFFAOYSA-N n-[3-(4-fluorophenyl)-3-(furan-2-yl)propyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCC(C=1C=CC(F)=CC=1)C1=CC=CO1 IHZQFSMUJTTZOK-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- NGHMEZWZOZEZOH-UHFFFAOYSA-N silicic acid;hydrate Chemical compound O.O[Si](O)(O)O NGHMEZWZOZEZOH-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000001959 sucrose esters of fatty acids Substances 0.000 description 1
- 235000010965 sucrose esters of fatty acids Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000205396 | 2000-07-06 | ||
| JP2000266780 | 2000-09-04 | ||
| PCT/JP2001/005764 WO2002004461A1 (fr) | 2000-07-06 | 2001-07-03 | Sels d'addition acides de dérivés hydropyridine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030022D0 NO20030022D0 (no) | 2003-01-03 |
| NO20030022L NO20030022L (no) | 2003-03-05 |
| NO328651B1 true NO328651B1 (no) | 2010-04-19 |
Family
ID=26595526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030022A NO328651B1 (no) | 2000-07-06 | 2003-01-03 | Syreaddisjonssalter av et hydropyridinderivat, medikamenter som inneholder disse, anvendelse av saltene til fremstilling av medikamenter og fremgangsmate for fremstilling av syreaddisjonssaltene av hydropyridinderivatet |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6693115B2 (cs) |
| EP (2) | EP1728794B1 (cs) |
| KR (6) | KR20030014294A (cs) |
| CN (1) | CN1214031C (cs) |
| AT (2) | ATE346071T1 (cs) |
| AU (2) | AU6791601A (cs) |
| BR (1) | BR0112168A (cs) |
| CA (2) | CA2415558C (cs) |
| CY (3) | CY1107554T1 (cs) |
| CZ (1) | CZ302990B6 (cs) |
| DE (2) | DE60134508D1 (cs) |
| DK (2) | DK1298132T3 (cs) |
| ES (2) | ES2276801T3 (cs) |
| HK (2) | HK1051362A1 (cs) |
| HU (2) | HU230762B1 (cs) |
| IL (2) | IL153546A0 (cs) |
| MX (1) | MXPA03000031A (cs) |
| NO (1) | NO328651B1 (cs) |
| NZ (1) | NZ523416A (cs) |
| PL (1) | PL208386B1 (cs) |
| PT (2) | PT1298132E (cs) |
| RU (1) | RU2238275C1 (cs) |
| TW (1) | TWI290927B (cs) |
| WO (1) | WO2002004461A1 (cs) |
Families Citing this family (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA03005770A (es) | 2000-12-25 | 2003-09-10 | Sankyo Co | Composiciones medicinales que contienen aspirina. |
| RU2005104432A (ru) * | 2002-07-18 | 2005-08-10 | Санкио Компани, Лимитед (Jp) | Лекарственная композиция для лечения артериосклероза |
| WO2004098713A2 (en) * | 2003-05-05 | 2004-11-18 | Eli Lilly And Company | Treating cardiovascular diseases with a compound of formula (i) (cs 747 - prasugrel; rn 150322-43-4) |
| US8586085B2 (en) * | 2004-11-08 | 2013-11-19 | Biokey, Inc. | Methods and formulations for making pharmaceutical compositions containing bupropion |
| US20060099261A1 (en) * | 2004-11-08 | 2006-05-11 | Biokey, Inc. | Methods and formulations for making controlled release oral dosage form |
| US20060099262A1 (en) * | 2004-11-08 | 2006-05-11 | Biokey, Inc. | Methods and formulations for making controlled release oral dosage form |
| CN1318428C (zh) * | 2005-02-23 | 2007-05-30 | 天津药物研究院 | 噻吩并吡啶取代的乙酰肼衍生物 |
| TWI318571B (en) * | 2005-06-10 | 2009-12-21 | Lilly Co Eli | Formulation of a thienopyridine platelet aggregation inhibitor |
| BRPI0612624A2 (pt) * | 2005-06-17 | 2016-11-29 | Lilly Co Eli | métodos para tratar doença vascular em um humano, e para prevenção e/ou tratamento de uma doença induzida por trombose ou uma doença induzida por tromboembolismo em um humano, e, uso de um composto |
| WO2007024472A2 (en) * | 2005-08-19 | 2007-03-01 | Eli Lilly And Company | USE OF PAR- l/PAR- 4 INHIBITORS FOR TREATING OR PREVENTING VASCULAR DISEASES |
| US8056072B2 (en) | 2005-10-31 | 2011-11-08 | Microsoft Corporation | Rebootless display driver upgrades |
| TR201816133T4 (tr) | 2006-04-04 | 2018-11-21 | Kg Acquisition Llc | Bi̇r anti̇platelet ajan ve bi̇r asi̇t i̇nhi̇bi̇törü i̇çeren oral dozaj formlari. |
| TWI392681B (zh) * | 2006-04-06 | 2013-04-11 | Daiichi Sankyo Co Ltd | 高純度普拉格雷及其酸加成鹽之製法 |
| US20100204470A1 (en) * | 2006-06-27 | 2010-08-12 | Sandoz Ag | method for salt preparation |
| US20100062066A1 (en) * | 2006-11-14 | 2010-03-11 | Acusphere, Inc | Formulations of Tetrahydropyridine Antiplatelet Agents for Parenteral or Oral Administration |
| US20090291138A1 (en) * | 2006-12-07 | 2009-11-26 | Daiichi Sankyo Company, Limited | Film-coated preparation having improved stability |
| EP2100607A4 (en) * | 2006-12-07 | 2010-01-06 | Daiichi Sankyo Co Ltd | PHARMACEUTICAL COMPOSITION HAVING ENHANCED STORAGE STABILITY |
| KR101442862B1 (ko) * | 2006-12-07 | 2014-09-22 | 다이이찌 산쿄 가부시키가이샤 | 만니톨 또는 유당을 함유하는 고형 제제 |
| TWI405591B (zh) * | 2006-12-07 | 2013-08-21 | Daiichi Sankyo Co Ltd | 固形製劑之製造方法 |
| EP2100610A4 (en) * | 2006-12-07 | 2009-12-02 | Daiichi Sankyo Co Ltd | PHARMACEUTICAL COMPOSITION WITH LOW SUBSTITUTED HYDROXYPROPYL CELLULOSE |
| MY151726A (en) * | 2007-03-02 | 2014-06-30 | Daiichi Sankyo Co Ltd | Process for production of prasugrel hydrochloride having high purity |
| HUE053158T2 (hu) | 2007-04-27 | 2021-06-28 | Cydex Pharmaceuticals Inc | Clopidogrelt és szulfoalkiléter ciklodextrint tartalmazó készítmények és alkalmazási eljárások |
| CZ302135B6 (cs) * | 2007-07-09 | 2010-11-10 | Zentiva, A. S. | Zpusob výroby 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4, 5, 6, 7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu (prasugrelu) |
| US20100261908A1 (en) * | 2007-11-09 | 2010-10-14 | Dr. Reddy's Laboratories Ltd. | Processes for the preparation of prasugrel , and its salts and polymorphs |
| HU230261B1 (hu) * | 2007-11-27 | 2015-11-30 | Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság | Eljárás gyógyszeripari intermedierek előállítására |
| CN101177430A (zh) * | 2007-12-11 | 2008-05-14 | 鲁南制药集团股份有限公司 | 氢化吡啶衍生物及其盐的制备方法 |
| US20110003847A1 (en) * | 2008-02-06 | 2011-01-06 | Helm Ag | Prasugrel Salts with Improved Properties |
| WO2009129983A1 (en) * | 2008-04-21 | 2009-10-29 | Ratiopharm Gmbh | Acid addition salts of prasugrel and pharmaceutical compositions comprising the same |
| ATE482961T1 (de) * | 2008-04-25 | 2010-10-15 | Sandoz Ag | Hydrogensulfat von 2-acetoxy-5-(a- cyclopropylcarbonyl-2-fluorbenzyl)-4,5,6,7- tetrahydrothienoä3,2-cüpyridin und dessen zubereitung |
| US20090281136A1 (en) * | 2008-05-08 | 2009-11-12 | Sandeep Mhetre | Prasugrel pharmaceutical formulations |
| WO2009140092A1 (en) * | 2008-05-13 | 2009-11-19 | The Medicines Company | Maintenance of platelet inhibition during antiplatelet therapy |
| US20120141468A1 (en) * | 2008-05-13 | 2012-06-07 | Lisa Ruderman Chen | Maintenance of platelet inhibition during antiplatelet therapy |
| US8759316B2 (en) * | 2008-05-13 | 2014-06-24 | The Medicines Company | Maintenance of platelet inhibition during antiplatelet therapy |
| US20130303477A1 (en) * | 2008-05-13 | 2013-11-14 | The Medicines Company | Maintenance of Platelet Inhibition During Antiplatelet Therapy |
| US9427448B2 (en) | 2009-11-11 | 2016-08-30 | The Medicines Company | Methods of treating, reducing the incidence of, and/or preventing ischemic events |
| JP2011529859A (ja) * | 2008-08-02 | 2011-12-15 | ルナン ファーマシューティカル グループ コーポレーション | プラスグレル重硫酸塩及びその薬物組成物並びにその応用 |
| EP2398468B1 (en) | 2009-02-17 | 2016-11-30 | KRKA, D.D., Novo Mesto | Pharmaceutical compositions comprising prasugrel base or its pharmaceutically acceptable acid addition salts and processes for their preparation |
| RU2484094C1 (ru) * | 2009-03-31 | 2013-06-10 | Шанхай Инститьют Оф Фармасьютикал Индастри | Кристаллы гидробромата прасугреля |
| EP3061460A1 (en) | 2009-04-10 | 2016-08-31 | Tufts Medical Center, Inc. | Par-1 activation by metalloproteinase-1 (mmp-1) |
| PL3100728T3 (pl) * | 2009-05-13 | 2020-05-18 | Cydex Pharmaceuticals, Inc. | Kompozycje farmaceutyczne zawierające prasugrel i pochodne cyklodekstryny oraz sposoby ich wytwarzania i zastosowania |
| WO2011004392A1 (en) * | 2009-07-06 | 2011-01-13 | Glenmark Generics Limited | Crystalline form of prasugrel hydrobromide, preparation and application thereof |
| DE102009036646A1 (de) | 2009-08-07 | 2011-02-10 | Ratiopharm Gmbh | Prasugrel in nicht-kristalliner Form und pharmazeutische Zusammensetzung davon |
| CN101993447A (zh) | 2009-08-26 | 2011-03-30 | 浙江华海药业股份有限公司 | 一种人工合成普拉格雷的方法 |
| WO2011036533A1 (en) * | 2009-09-23 | 2011-03-31 | Glenmark Pharmaceuticals Limited | Pharmaceutical composition comprising prasugrel and triflusal |
| AU2010319612B2 (en) | 2009-11-11 | 2016-01-14 | Chiesi Farmaceutici S.P.A. | Methods of treating or preventing stent thrombosis |
| US10376532B2 (en) | 2009-11-11 | 2019-08-13 | Chiesi Farmaceutici, S.P.A. | Methods of treating, reducing the incidence of, and/or preventing ischemic events |
| CZ2009762A3 (cs) | 2009-11-16 | 2011-05-25 | Zentiva, K. S. | Nové soli 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráneným názvem prasugrel a zpusob jejich výroby |
| CZ2009763A3 (cs) | 2009-11-16 | 2011-05-25 | Zentiva, K. S. | Zpusob výroby vysoce cistého 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráneným názvem prasugrel a jeho nových farmaceuticky prijatelných solí. |
| CZ2009828A3 (cs) | 2009-12-09 | 2011-06-22 | Zentiva, K.S. | Zpusob prípravy hydrochloridu 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu (prasugrelu hydrochloridu) v polymorfní forme B |
| HU229035B1 (en) * | 2009-12-21 | 2013-07-29 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Process for producing prasurgel |
| WO2011092720A2 (en) * | 2010-02-01 | 2011-08-04 | Msn Laboratories Limited | Pharmaceutical composition of prasugrel and its pharmaceutically acceptable salts |
| EP2360159A1 (de) | 2010-02-11 | 2011-08-24 | Ratiopharm GmbH | Prasugrel in mikronisierter, kristalliner Form und pharmazeutische Zusammensetzung davon |
| EP2545059A1 (en) | 2010-03-09 | 2013-01-16 | Synthon BV | A process for making prasugrel |
| KR101184915B1 (ko) | 2010-03-11 | 2012-09-21 | 한미사이언스 주식회사 | 고순도 프라수그렐의 제조방법 |
| US20130053569A1 (en) | 2010-03-23 | 2013-02-28 | Jayaraman Venkat Raman | Process for the preparation of prasugrel hcl salt |
| EP2377520A1 (de) | 2010-03-24 | 2011-10-19 | Ratiopharm GmbH | Pharmazeutische Zusammensetzung des Prasugrels |
| CN102212068A (zh) * | 2010-04-06 | 2011-10-12 | 刘桂坤 | 噻吩衍生物及其制备方法和在药物上的应用 |
| PT2448945E (pt) | 2010-04-08 | 2015-04-09 | Teva Pharma | Formas cristalinas de sais de prasugrel |
| CN102212071B (zh) * | 2010-04-08 | 2014-03-26 | 上海医药工业研究院 | 普拉格雷盐酸盐乙酸溶剂合物及其结晶和制备方法 |
| ES2592280T3 (es) | 2010-04-19 | 2016-11-29 | Cadila Healthcare Limited | Una composición farmacéutica que comprende agentes antiplaquetarios y un agente estimulante de eritropoyesis |
| WO2012001486A1 (en) * | 2010-06-28 | 2012-01-05 | Mayuka Labs Pvt. Ltd. | An improved process for the preparation of prasugrel hydrochloride and its intermediates |
| TR201007926A1 (tr) | 2010-07-19 | 2012-02-21 | Sanovel İlaç San.Ve Ti̇c.A.Ş. | Prasugrel tablet formülasyonları. |
| EP2409685A3 (en) | 2010-07-19 | 2012-02-01 | Sanovel Ilac Sanayi ve Ticaret A.S. | Orally-disintegrating formulations of prasugrel |
| TR201005900A1 (tr) | 2010-07-19 | 2012-02-21 | Sanovel İlaç San. Ve Ti̇c. A.Ş. | Geliştirilmiş stabiliteye sahip prasugrel granülleri. |
| TR201006802A1 (tr) * | 2010-08-17 | 2012-03-21 | Sanovel İlaç San. Ve Ti̇c. A.Ş. | Prasugrelin oral yolla dağılan formülasyonları. |
| WO2012023145A2 (en) * | 2010-08-18 | 2012-02-23 | Hetero Research Foundation | Prasugrel hydrochloride crystalline particles |
| HUP1000565A2 (en) | 2010-10-22 | 2012-05-02 | Egis Gyogyszergyar Nyrt | Process for the preparation of pharmaceutically active compound and intermediers |
| CN101985450B (zh) * | 2010-11-02 | 2012-07-11 | 北京赛科药业有限责任公司 | 普拉格雷盐及其制备方法 |
| CN102532157A (zh) * | 2010-12-16 | 2012-07-04 | 瑞阳制药有限公司 | 普拉格雷的可药用酸加成盐化合物及其制备方法 |
| CZ305314B6 (cs) * | 2010-12-30 | 2015-07-29 | Zentiva, K.S. | Nový hydrobromid formy C 5-[2-cyklopropyl-1-(2-fluorofenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráněným názvem prasugrel a způsob jeho výroby |
| CN102199163A (zh) * | 2011-04-01 | 2011-09-28 | 中国药科大学 | 2-羟基四氢噻吩并吡啶衍生物及其制备方法与在制药中的用途 |
| CN102746318A (zh) * | 2011-04-20 | 2012-10-24 | 上海信谊药厂有限公司 | 用于制备普拉格雷盐酸盐的方法 |
| WO2012158983A2 (en) | 2011-05-17 | 2012-11-22 | Qiyong Peter Liu | Improved platelet storage using a sialidase inhibitor |
| US9788539B2 (en) | 2011-05-17 | 2017-10-17 | Velico Medical, Inc. | Platelet protection solution having beta-galactosidase and sialidase inhibitors |
| CN102838618A (zh) * | 2011-06-22 | 2012-12-26 | 广东东阳光药业有限公司 | 一种制备普拉格雷的方法及普拉格雷盐酸盐新晶型 |
| JP2014524929A (ja) | 2011-07-28 | 2014-09-25 | ラボラトリオス レスヴィ，エス．エル． | プラスグレルの調製方法 |
| CN103102355A (zh) * | 2011-11-09 | 2013-05-15 | 丁克 | 具有旋光性的四氢噻吩并吡啶化合物 |
| CZ2011872A3 (cs) | 2011-12-22 | 2013-07-03 | Zentiva, K.S. | Farmaceutická formulace prasugrelu hydrobromidu |
| US8603537B2 (en) | 2012-04-02 | 2013-12-10 | Egis Pharmaceuticals Plc | Prasugrel containing quickly released stable oral pharmaceutical compositions |
| CA2887083A1 (en) | 2012-10-05 | 2014-04-10 | Velico Medical, Inc. | Platelet additive solution having a beta-galactosidase inhibitor |
| EP2722036A1 (en) | 2012-10-19 | 2014-04-23 | Sanovel Ilac Sanayi ve Ticaret A.S. | Solid oral formulations of prasugrel |
| EP2722037A1 (en) | 2012-10-19 | 2014-04-23 | Sanovel Ilac Sanayi ve Ticaret A.S. | Prasugrel formulations |
| PL402028A1 (pl) | 2012-12-12 | 2014-06-23 | Instytut Farmaceutyczny | Sposób wytwarzania postaci polimorficznej B chlorowodorku prasugrelu o czystości farmaceutycznej |
| HU230649B1 (hu) | 2013-01-24 | 2017-05-29 | Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság | Javított eljárás prasugrel gyógyszeripari hatóanyag és az 1-ciklopropil-2-(2-fluorofenil)-etanon intermedier előállítására |
| WO2014120886A1 (en) | 2013-01-30 | 2014-08-07 | Velico Medical, Inc. | Platelet additive solution having a self-assembling hydrogel-forming peptide |
| KR102235732B1 (ko) | 2013-12-26 | 2021-04-02 | 에스케이플래닛 주식회사 | 쿠폰 관리 시스템 및 방법, 그리고 이를 위한 장치 및 컴퓨터 프로그램이 기록된 기록매체 |
| DE102014108210A1 (de) | 2014-06-11 | 2015-12-17 | Dietrich Gulba | Rodentizid |
| EP2979693A1 (en) | 2014-08-01 | 2016-02-03 | Zaklady Farmaceutyczne Polpharma SA | Pharmaceutical composition comprising prasugrel or pharmaceutically acceptable salt thereof and process for its preparation |
| CN104479502A (zh) * | 2014-12-31 | 2015-04-01 | 江阴市天邦涂料股份有限公司 | 一种水性防腐涂料 |
| WO2016122421A1 (en) | 2015-01-29 | 2016-08-04 | Pharmactive Ilaç Sanayi Ve Ticaret A.Ş. | Stable pharmaceutical compositions containing prasugrel base |
| EP3106151A1 (en) | 2015-06-19 | 2016-12-21 | Sanovel Ilac Sanayi ve Ticaret A.S. | Pharmaceutical compositions of prasugrel hydrobromide |
| EP3156049A1 (en) | 2015-10-15 | 2017-04-19 | Alembic Pharmaceuticals Limited | Pharmaceutical composition of prasugrel |
| EP3158993A1 (en) | 2015-10-22 | 2017-04-26 | Zaklady Farmaceutyczne Polpharma SA | Process for preparing a tablet comprising prasugrel or pharmaceutically acceptable salt thereof |
| HU231079B1 (hu) | 2016-06-23 | 2020-06-29 | Richter Gedeon Nyrt. | Eljárás nagytisztaságú Prasugrel előállítására bromopentil szennyezés eltávolításával |
| WO2018073437A1 (en) | 2016-10-21 | 2018-04-26 | Laboratorios Lesvi, Sl | Pharmaceutical formulations of prasugrel and processes for the preparation thereof |
| CN106632391A (zh) * | 2016-12-23 | 2017-05-10 | 山东鲁抗医药股份有限公司 | 一种盐酸普拉格雷化合物及其制备方法和含有盐酸普拉格雷的药物组合物 |
| WO2018234565A1 (en) | 2017-06-23 | 2018-12-27 | Chiesi Farmaceutici S.P.A. | METHOD FOR PREVENTING SHUNT THROMBOSIS FROM THE SYSTEMIC-PULMONARY ARTERY |
| KR102063862B1 (ko) | 2018-08-09 | 2020-01-08 | 한국기술교육대학교 산학협력단 | Qr코드 기반의 공유시점관리 시스템 |
| KR102491932B1 (ko) | 2020-11-18 | 2023-01-27 | 현대엠시스템즈 주식회사 | 통신 방식 가변형 원격 모니터링 제어 시스템 및 방법 |
| KR102485021B1 (ko) | 2020-11-18 | 2023-01-05 | 효성중공업 주식회사 | 델타구조 반도체변압기 기반 에너지 저장장치의 SoC 균등제어 장치 및 방법 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141894A (en) * | 1976-11-02 | 1979-02-27 | Eli Lilly And Company | Trans-5a-aryl-decahydrobenzazepines |
| FR2576901B1 (fr) | 1985-01-31 | 1987-03-20 | Sanofi Sa | Nouveaux derives de l'acide a-(oxo-2 hexahydro-2,4,5,6,7,7a thieno (3,2-c) pyridyl-5) phenyl acetique, leur procede de preparation et leur application therapeutique |
| JP2506376B2 (ja) * | 1987-07-16 | 1996-06-12 | 三菱化学株式会社 | ２−（４−メチルアミノブトキシ）ジフェニルメタン・塩酸塩の製造方法 |
| FI101150B (fi) | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
| US5342851A (en) * | 1992-10-07 | 1994-08-30 | Mcneil-Ppc, Inc. | Substituted thiazole derivatives useful as platelet aggregation inhibitors |
| JPH07188168A (ja) * | 1993-12-28 | 1995-07-25 | Fujisawa Pharmaceut Co Ltd | ジヒドロピリジン化合物およびその製造方法 |
| MXPA03005770A (es) * | 2000-12-25 | 2003-09-10 | Sankyo Co | Composiciones medicinales que contienen aspirina. |
| CZ2009762A3 (cs) | 2009-11-16 | 2011-05-25 | Zentiva, K. S. | Nové soli 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráneným názvem prasugrel a zpusob jejich výroby |
| CZ305314B6 (cs) | 2010-12-30 | 2015-07-29 | Zentiva, K.S. | Nový hydrobromid formy C 5-[2-cyklopropyl-1-(2-fluorofenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráněným názvem prasugrel a způsob jeho výroby |
-
2001
- 2001-07-03 CN CNB018151086A patent/CN1214031C/zh not_active Expired - Lifetime
- 2001-07-03 KR KR1020027018077A patent/KR20030014294A/ko not_active Application Discontinuation
- 2001-07-03 AT AT01945799T patent/ATE346071T1/de active
- 2001-07-03 KR KR1020097004397A patent/KR20090033917A/ko not_active Application Discontinuation
- 2001-07-03 EP EP06017487A patent/EP1728794B1/en not_active Expired - Lifetime
- 2001-07-03 RU RU2003100082A patent/RU2238275C1/ru active Protection Beyond IP Right Term
- 2001-07-03 CA CA2415558A patent/CA2415558C/en not_active Expired - Lifetime
- 2001-07-03 PT PT01945799T patent/PT1298132E/pt unknown
- 2001-07-03 KR KR1020127010456A patent/KR20120062906A/ko not_active Application Discontinuation
- 2001-07-03 DK DK01945799T patent/DK1298132T3/da active
- 2001-07-03 CA CA2703697A patent/CA2703697C/en not_active Expired - Lifetime
- 2001-07-03 PT PT06017487T patent/PT1728794E/pt unknown
- 2001-07-03 KR KR1020137026138A patent/KR20130118395A/ko active Search and Examination
- 2001-07-03 AU AU6791601A patent/AU6791601A/xx active Pending
- 2001-07-03 CZ CZ20030018A patent/CZ302990B6/cs not_active IP Right Cessation
- 2001-07-03 KR KR1020107017585A patent/KR20100105763A/ko not_active Application Discontinuation
- 2001-07-03 HU HU1100350A patent/HU230762B1/hu unknown
- 2001-07-03 ES ES01945799T patent/ES2276801T3/es not_active Expired - Lifetime
- 2001-07-03 BR BR0112168-5A patent/BR0112168A/pt not_active Application Discontinuation
- 2001-07-03 DE DE60134508T patent/DE60134508D1/de not_active Expired - Lifetime
- 2001-07-03 ES ES06017487T patent/ES2308633T3/es not_active Expired - Lifetime
- 2001-07-03 AU AU2001267916A patent/AU2001267916B2/en not_active Expired
- 2001-07-03 NZ NZ523416A patent/NZ523416A/en not_active IP Right Cessation
- 2001-07-03 DE DE60124712T patent/DE60124712T2/de not_active Expired - Lifetime
- 2001-07-03 HU HU0301645A patent/HU227746B1/hu unknown
- 2001-07-03 WO PCT/JP2001/005764 patent/WO2002004461A1/ja active IP Right Grant
- 2001-07-03 MX MXPA03000031A patent/MXPA03000031A/es active IP Right Grant
- 2001-07-03 KR KR1020087001896A patent/KR20080021152A/ko not_active Application Discontinuation
- 2001-07-03 EP EP01945799A patent/EP1298132B1/en not_active Expired - Lifetime
- 2001-07-03 DK DK06017487T patent/DK1728794T3/da active
- 2001-07-03 AT AT06017487T patent/ATE398624T1/de active
- 2001-07-03 PL PL359393A patent/PL208386B1/pl unknown
- 2001-07-03 IL IL15354601A patent/IL153546A0/xx active IP Right Grant
- 2001-07-06 TW TW090116563A patent/TWI290927B/zh active
-
2002
- 2002-12-19 IL IL153546A patent/IL153546A/en unknown
- 2002-12-26 US US10/329,629 patent/US6693115B2/en not_active Expired - Fee Related
-
2003
- 2003-01-03 NO NO20030022A patent/NO328651B1/no not_active IP Right Cessation
- 2003-05-13 HK HK03103335A patent/HK1051362A1/xx not_active IP Right Cessation
-
2007
- 2007-02-12 CY CY20071100188T patent/CY1107554T1/el unknown
- 2007-04-13 HK HK07103874A patent/HK1096684A1/xx not_active IP Right Cessation
-
2008
- 2008-09-11 CY CY20081100983T patent/CY1110395T1/el unknown
-
2009
- 2009-08-03 CY CY2009011C patent/CY2009011I2/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO328651B1 (no) | Syreaddisjonssalter av et hydropyridinderivat, medikamenter som inneholder disse, anvendelse av saltene til fremstilling av medikamenter og fremgangsmate for fremstilling av syreaddisjonssaltene av hydropyridinderivatet | |
| FI87216C (fi) | Foerfarande foer framstaellning av en hoegervridande enantiomer av metyl-alfa-5-(4,5,6,7-tetrahydro(3,2-c)tienopyridyl)-(2-klorfenyl)acetat | |
| EP2112155A1 (en) | Hydrogensulfate salt of 2-acetoxy-5-(a-cyclopropylcarbonyl-2-fluorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine and its preparation | |
| NZ571746A (en) | Process for producing high-purity prasugrel and acid addition salt thereof | |
| EP0505058B1 (en) | Thienopyridine derivatives and pharmaceutical compositions containing them | |
| JP4029974B2 (ja) | ヒドロピリジン誘導体酸付加塩を含有する医薬 | |
| RU2114845C1 (ru) | Производные имидазопиридина или их фармацевтически приемлемые соли, способ их получения и фармацевтическая композиция, проявляющая антагонистическую активность в отношении гистамина (h1) | |
| EP0274443B1 (en) | Heteroaryl 3-oxo-propanenitrile derivatives and process for their preparation | |
| JP4001199B2 (ja) | ヒドロピリジン誘導体酸付加塩 | |
| JP2013526488A (ja) | シアノ基を含有するチエノピリジンエステル誘導体、その調製方法、使用および組成物 | |
| CA2210571A1 (en) | Bicyclic benzazepine derivatives as vasopressin antagonists | |
| IE44122B1 (en) | New thienopyridine derivatives, and their application | |
| IE46288B1 (en) | Improvements in or relating to 4,5,6,7-tetrahydrothieno (28,3-c)-and(3,2-c)pyridines,process for their preparation and their applications | |
| GB2039882A (en) | Bicyclic thiadiaza compounds and their use as medicaments | |
| KR950014866B1 (ko) | 에르골리닐 헤테로사이클 | |
| NO159594B (no) | Analogifremgangsm te ved fremstilling av terapeutisk aktive dihydropyridin-3,5-dicarboxylsyreester-derivater. | |
| EP0668276A1 (en) | 2-alkoxy-5,6,7,8-tetrahydroquinoxaline derivative, process for producing the same, and use thereof | |
| EP1151993A1 (en) | Cyclic amine derivatives and uses thereof | |
| US20050153954A1 (en) | Novel crystalline polymorph form-vi of olanzapine and a process for preparation thereof | |
| JP2000072776A (ja) | チエノジピリジン誘導体、その製造法および用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |