ES2654927T3 - Formulaciones orales de derivados de pirrolidina - Google Patents
Formulaciones orales de derivados de pirrolidina Download PDFInfo
- Publication number
- ES2654927T3 ES2654927T3 ES14820814.3T ES14820814T ES2654927T3 ES 2654927 T3 ES2654927 T3 ES 2654927T3 ES 14820814 T ES14820814 T ES 14820814T ES 2654927 T3 ES2654927 T3 ES 2654927T3
- Authority
- ES
- Spain
- Prior art keywords
- volumes
- methyl
- biphenyl
- carbonyl
- hydroxymethyl
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title description 72
- 238000009472 formulation Methods 0.000 title description 45
- 150000003235 pyrrolidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 33
- 239000007919 dispersible tablet Substances 0.000 abstract description 31
- 239000000546 pharmaceutical excipient Substances 0.000 abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 239000003826 tablet Substances 0.000 description 33
- 239000002775 capsule Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000008187 granular material Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 238000004090 dissolution Methods 0.000 description 15
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
- 238000001556 precipitation Methods 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000011282 treatment Methods 0.000 description 11
- 241000282472 Canis lupus familiaris Species 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 239000002207 metabolite Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- -1 2'-methyl-1,1'-biphenyl-4-yl Chemical group 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229960002537 betamethasone Drugs 0.000 description 9
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 9
- 239000000378 calcium silicate Substances 0.000 description 9
- 229910052918 calcium silicate Inorganic materials 0.000 description 9
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- CTKXFMQHOOWWEB-UHFFFAOYSA-N Ethylene oxide/propylene oxide copolymer Chemical compound CCCOC(C)COCCO CTKXFMQHOOWWEB-UHFFFAOYSA-N 0.000 description 7
- 239000012296 anti-solvent Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000036470 plasma concentration Effects 0.000 description 7
- 229920001993 poloxamer 188 Polymers 0.000 description 7
- 229940044519 poloxamer 188 Drugs 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 238000005550 wet granulation Methods 0.000 description 7
- GNWCZBXSKIIURR-UHFFFAOYSA-N (2-docosanoyloxy-3-hydroxypropyl) docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCCCCCC GNWCZBXSKIIURR-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 238000001694 spray drying Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.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 WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 208000006399 Premature Obstetric Labor Diseases 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012738 dissolution medium Substances 0.000 description 5
- 229960001021 lactose monohydrate Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000002604 ultrasonography Methods 0.000 description 5
- 229920002785 Croscarmellose sodium Polymers 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 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 description 4
- 229960001681 croscarmellose sodium Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-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 3
- 241001465754 Metazoa Species 0.000 description 3
- SJYKZNVCYBDVTO-UHFFFAOYSA-N OCC1N(CCC1=O)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C Chemical compound OCC1N(CCC1=O)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C SJYKZNVCYBDVTO-UHFFFAOYSA-N 0.000 description 3
- 206010036595 Premature delivery Diseases 0.000 description 3
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000003246 corticosteroid Substances 0.000 description 3
- 229960001334 corticosteroids Drugs 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 208000000509 infertility Diseases 0.000 description 3
- 230000036512 infertility Effects 0.000 description 3
- 210000001161 mammalian embryo Anatomy 0.000 description 3
- 238000007909 melt granulation Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000011002 quantification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 description 2
- NDNIPPKLIDCYGD-UHFFFAOYSA-N 4-(2-methylphenyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1 NDNIPPKLIDCYGD-UHFFFAOYSA-N 0.000 description 2
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 208000005171 Dysmenorrhea Diseases 0.000 description 2
- 206010013935 Dysmenorrhoea Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 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 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 239000002156 adsorbate Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 235000013681 dietary sucrose Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 230000032692 embryo implantation Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-M prolinate Chemical compound [O-]C(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 210000004291 uterus Anatomy 0.000 description 2
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- FPIFOOSMBNMTBX-SFHVURJKSA-N (2s)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxylic acid Chemical compound C1C(=NOC)C[C@@H](C(O)=O)N1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 FPIFOOSMBNMTBX-SFHVURJKSA-N 0.000 description 1
- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 description 1
- BNPUEPYZSZOTKI-UHFFFAOYSA-N 1-[4-(2-methylphenyl)benzoyl]pyrrolidin-3-one Chemical compound CC1=CC=CC=C1C1=CC=C(C(=O)N2CC(=O)CC2)C=C1 BNPUEPYZSZOTKI-UHFFFAOYSA-N 0.000 description 1
- CKACLTLWGSHBQM-UHFFFAOYSA-N 5-(hydroxymethyl)-1-[4-(2-methylphenyl)benzoyl]pyrrolidin-3-one Chemical compound CC1=CC=CC=C1C1=CC=C(C(=O)N2C(CC(=O)C2)CO)C=C1 CKACLTLWGSHBQM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028974 Neonatal respiratory distress syndrome Diseases 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- 206010036600 Premature labour Diseases 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- OLUJSZLBWZWGJT-HGBKYHTQSA-N [(2s,4z)-2-(hydroxymethyl)-4-methoxyiminopyrrolidin-1-yl]-[4-(2-methylphenyl)phenyl]methanone Chemical compound C1C(=N/OC)\C[C@@H](CO)N1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 OLUJSZLBWZWGJT-HGBKYHTQSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 229960004977 anhydrous lactose Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000037020 contractile activity Effects 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 108010037444 diisopropylglutathione ester Proteins 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 201000003511 ectopic pregnancy Diseases 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 210000004696 endometrium Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 208000021267 infertility disease Diseases 0.000 description 1
- 230000009027 insemination Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 230000007040 lung development Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 206010036596 premature ejaculation Diseases 0.000 description 1
- 208000026440 premature labor Diseases 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000010346 psychosocial stress Effects 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000011273 social behavior Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/401—Proline; Derivatives thereof, e.g. captopril
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Inorganic Chemistry (AREA)
- Reproductive Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13197606 | 2013-12-17 | ||
| EP13197606.0A EP2886107A1 (en) | 2013-12-17 | 2013-12-17 | Oral formulations of pyrrolydine derivatives |
| PCT/EP2014/077767 WO2015091365A1 (en) | 2013-12-17 | 2014-12-15 | Oral formulations of pyrrolidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2654927T3 true ES2654927T3 (es) | 2018-02-15 |
Family
ID=49765403
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14820814.3T Active ES2654927T3 (es) | 2013-12-17 | 2014-12-15 | Formulaciones orales de derivados de pirrolidina |
| ES17188131T Active ES2726730T3 (es) | 2013-12-17 | 2014-12-15 | Formulaciones orales de derivados de pirrolidina |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES17188131T Active ES2726730T3 (es) | 2013-12-17 | 2014-12-15 | Formulaciones orales de derivados de pirrolidina |
Country Status (19)
| Country | Link |
|---|---|
| US (5) | US20170065556A1 (OSRAM) |
| EP (4) | EP2886107A1 (OSRAM) |
| JP (2) | JP6479800B2 (OSRAM) |
| KR (1) | KR102350156B1 (OSRAM) |
| CN (2) | CN110960495B (OSRAM) |
| AU (1) | AU2014364962B2 (OSRAM) |
| CA (1) | CA2931592C (OSRAM) |
| CY (1) | CY1119728T1 (OSRAM) |
| DK (1) | DK3082773T3 (OSRAM) |
| EA (2) | EA031530B1 (OSRAM) |
| ES (2) | ES2654927T3 (OSRAM) |
| HK (1) | HK1249050B (OSRAM) |
| HU (1) | HUE035212T2 (OSRAM) |
| IL (2) | IL245855B (OSRAM) |
| MX (2) | MX363697B (OSRAM) |
| PT (1) | PT3082773T (OSRAM) |
| SI (1) | SI3082773T1 (OSRAM) |
| UA (1) | UA116824C2 (OSRAM) |
| WO (1) | WO2015091365A1 (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2845850A1 (en) | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidine derivatives as oxytocin/vasopressin V1a receptors antagonists |
| EP2886107A1 (en) * | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Oral formulations of pyrrolydine derivatives |
| EP3753921A1 (en) | 2014-07-02 | 2020-12-23 | ObsEva S.A. | Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime useful in methods of treating conditions related to the ot-r activity |
| TWI829098B (zh) | 2015-01-02 | 2024-01-11 | 美商梅拉洛伊卡公司 | 細菌組成物 |
| ES2915948T3 (es) | 2016-01-04 | 2022-06-27 | ObsEva SA | Administración conjunta de alfa-aminoéster de derivado de hidroxipropiltiazolidin-carboxamida y un agente tocolítico |
| WO2018015497A2 (en) * | 2016-07-21 | 2018-01-25 | ObsEva S.A. | Oxytocin antagonist dosing regimens for promoting embryo implantation and preventing miscarriage |
| IT201600101413A1 (it) | 2016-10-10 | 2018-04-10 | Sofar Swiss S A | Composizione liquida per uso nel trattamento del reflusso gastroesofageo |
| IT201700124434A1 (it) * | 2017-10-31 | 2019-05-01 | Sofar Swiss Sa | Compressa da succhiare e/o sciogliere in bocca a base di acido ialuronico e condroitina solfato e loro sali per uso nel trattamento di una sottopopolazione di pazienti GERD. |
| IT201700124424A1 (it) | 2017-10-31 | 2019-05-01 | Sofar Swiss Sa | Compressa da succhiare e/o sciogliere in bocca a base di acido ialuronico e condroitina solfato e loro sali |
| GB201910125D0 (en) * | 2019-07-15 | 2019-08-28 | Kalvista Pharmaceuticals Ltd | Treatments of angioedema |
| GB201910116D0 (en) * | 2019-07-15 | 2019-08-28 | Kalvista Pharmaceuticals Ltd | Treatments of hereditary angioedema |
| EP4025207A1 (en) * | 2019-09-03 | 2022-07-13 | ObsEva S.A. | Oxytocin antagonist dosing regimens for promoting embryo implantation and preventing miscarriage |
| AU2021218895A1 (en) | 2020-02-10 | 2022-09-15 | ObsEva S.A. | Biomarkers for oxytocin receptor antagonist therapy |
| SMT202200411T1 (it) | 2020-05-18 | 2022-11-18 | Orexo Ab | Nuova composizione farmaceutica per il rilascio controllato di farmaci |
| AU2022395920A1 (en) | 2021-11-25 | 2024-05-30 | Orexo Ab | Pharmaceutical composition comprising adrenaline |
| GB202117016D0 (en) | 2021-11-25 | 2022-01-12 | Orexo Ab | New pharmaceutical device |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3482815A (en) | 1967-07-07 | 1969-12-09 | Victor Naturale | Collapsible core for a mold |
| YU120988A (en) * | 1988-06-23 | 1990-06-30 | Lek Tovarna Farmacevtskih | Process for preparing new dispersion pills of cimetidine |
| US4832307A (en) | 1988-09-15 | 1989-05-23 | Toshiba Kikai Kabushiki Kaisha | Injection mold |
| YU183988A (en) * | 1988-09-30 | 1990-08-31 | Lek Tovarna Farmacevtskih | Process for preparing dispersion pills of dihydroergotoxine |
| US5089043A (en) | 1989-11-09 | 1992-02-18 | Shionogi & Co., Ltd. | Heterocyclic oxy-phenoxyacetic acid derivatives and their use as herbicides |
| US5889001A (en) | 1993-07-29 | 1999-03-30 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| JP2869854B2 (ja) | 1994-10-19 | 1999-03-10 | 株式会社トスカ | 合成樹脂の成形方法とその装置 |
| JP3534903B2 (ja) | 1995-06-09 | 2004-06-07 | 鐘淵化学工業株式会社 | １−［３−クロロ−（２ｓ）−メチルプロピオニル］−ピロリジン−（２ｓ）−カルボン酸の製造方法 |
| GB9603699D0 (en) * | 1996-02-21 | 1996-04-17 | Boots Co Plc | Therapeutic composition |
| US6696484B2 (en) * | 1997-10-31 | 2004-02-24 | University Of Chicago Office Of Technology And Intellectual Property | Method and compositions for regulation of 5-alpha reductase activity |
| US6329418B1 (en) | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| US20030180352A1 (en) * | 1999-11-23 | 2003-09-25 | Patel Mahesh V. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| DE60027761T2 (de) * | 1999-12-09 | 2007-01-25 | Reckitt Benckiser Healthcare (Uk) Ltd., Slough | Komprimierte zubereitung enthaltend nichtsteroidale entzündungshemmer |
| ES2261404T3 (es) | 2000-03-27 | 2006-11-16 | Applied Research Systems Ars Holding N.V. | Derivados de pirrolidina utiles como inhibidores de bax. |
| DK1268418T3 (da) | 2000-03-27 | 2006-09-25 | Applied Research Systems | Farmaceutisk aktive pyrrolidinderivater som Bax-inhibitorer |
| IL157995A0 (en) | 2001-03-20 | 2004-03-28 | Applied Research Systems | The use of pyrrolidine ester derivatives in modulation of oxytoxin activity, some new such derivatives, their preparation and pharmaceutical compositions containing them |
| EP1444225B1 (en) | 2001-06-18 | 2012-10-10 | Merck Serono SA | Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. |
| JP2003192582A (ja) * | 2001-12-12 | 2003-07-09 | Merck Patent Gmbh | ナプロキセンナトリウムを含む速放性錠剤 |
| UA78058C2 (en) | 2002-07-05 | 2007-02-15 | Applied Research Systems | Pyrrolidine derivative as oxitocin antagonists |
| ES2333719T3 (es) | 2003-02-27 | 2010-02-26 | Merck Serono Sa | Derivados de pirrolidina en calidad de antagonistas de oxitocina. |
| EA011026B1 (ru) | 2004-02-26 | 2008-12-30 | Лаборатуар Сероно Са | Способ получения пирролидиноксимов |
| GB2411355B (en) * | 2004-02-27 | 2006-02-22 | Niche Generics Ltd | Pharmaceutical composition |
| KR100985449B1 (ko) * | 2005-05-10 | 2010-10-05 | 페링 인터내셔널 센터 에스 에이 | 옥시톡신 및/또는 바소프레신 길항제의 용도 |
| WO2007052289A2 (en) * | 2005-07-22 | 2007-05-10 | Rubicon Research Pvt Ltd. | Novel dispersible tablet composition |
| EP1978939A2 (en) * | 2005-12-27 | 2008-10-15 | Jubilant Organosys Limited | Mouth dissolving pharmaceutical composition and process for preparing the same using a high amount of silicon dioxine |
| JP2008189732A (ja) | 2007-02-01 | 2008-08-21 | Fujifilm Corp | セルロースアシレート組成物、セルロースアシレートフィルム、光学補償シート、偏光板および液晶表示装置 |
| US20090152770A1 (en) | 2007-08-07 | 2009-06-18 | Canon Virginia Inc. | Mechanically collapsible core for injection molding |
| PT2572705T (pt) * | 2007-10-01 | 2017-11-08 | Lesvi Laboratorios Sl | Comprimidos orodispersíveis |
| US9201077B2 (en) | 2009-07-27 | 2015-12-01 | Colorado State University Research Foundation | Direct enzyme immunoassay for measurement of serum progesterone levels |
| HK1213454A1 (zh) | 2012-11-26 | 2016-07-08 | Ferring B.V. | 使用图像分析诊断子宫收缩水平的方法和系统 |
| JP5942815B2 (ja) | 2012-11-26 | 2016-06-29 | 株式会社ジェイテクト | 等速ジョイント用ブーツの成形金型 |
| EP2845850A1 (en) | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidine derivatives as oxytocin/vasopressin V1a receptors antagonists |
| EP2886107A1 (en) * | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Oral formulations of pyrrolydine derivatives |
| EP3753921A1 (en) | 2014-07-02 | 2020-12-23 | ObsEva S.A. | Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime useful in methods of treating conditions related to the ot-r activity |
| PL3037101T3 (pl) | 2014-12-22 | 2019-06-28 | Ferring B.V. | Terapia antagonistą receptora oksytocyny w fazie lutealnej w celu implantacji i uzyskania ciąży u kobiet poddawanych technikom wspomaganego rozrodu |
-
2013
- 2013-12-17 EP EP13197606.0A patent/EP2886107A1/en not_active Withdrawn
-
2014
- 2014-12-15 EA EA201691061A patent/EA031530B1/ru unknown
- 2014-12-15 CA CA2931592A patent/CA2931592C/en active Active
- 2014-12-15 JP JP2016534249A patent/JP6479800B2/ja active Active
- 2014-12-15 DK DK14820814.3T patent/DK3082773T3/en active
- 2014-12-15 WO PCT/EP2014/077767 patent/WO2015091365A1/en not_active Ceased
- 2014-12-15 ES ES14820814.3T patent/ES2654927T3/es active Active
- 2014-12-15 EP EP14820814.3A patent/EP3082773B1/en active Active
- 2014-12-15 CN CN201910736559.3A patent/CN110960495B/zh active Active
- 2014-12-15 MX MX2016007930A patent/MX363697B/es unknown
- 2014-12-15 PT PT148208143T patent/PT3082773T/pt unknown
- 2014-12-15 EA EA201892033A patent/EA201892033A3/ru unknown
- 2014-12-15 HU HUE14820814A patent/HUE035212T2/en unknown
- 2014-12-15 ES ES17188131T patent/ES2726730T3/es active Active
- 2014-12-15 US US15/104,683 patent/US20170065556A1/en not_active Abandoned
- 2014-12-15 UA UAA201606432A patent/UA116824C2/uk unknown
- 2014-12-15 SI SI201430538T patent/SI3082773T1/en unknown
- 2014-12-15 EP EP19150037.0A patent/EP3494967A1/en active Pending
- 2014-12-15 CN CN201480075770.0A patent/CN106029057B/zh active Active
- 2014-12-15 AU AU2014364962A patent/AU2014364962B2/en active Active
- 2014-12-15 EP EP17188131.1A patent/EP3266449B1/en active Active
- 2014-12-15 KR KR1020167018856A patent/KR102350156B1/ko active Active
- 2014-12-16 US US14/571,615 patent/US9962367B2/en active Active
-
2016
- 2016-05-25 IL IL245855A patent/IL245855B/en active IP Right Grant
- 2016-06-16 MX MX2019003598A patent/MX2019003598A/es unknown
-
2017
- 2017-12-28 CY CY20171101354T patent/CY1119728T1/el unknown
-
2018
- 2018-04-13 US US15/952,934 patent/US10478420B2/en active Active
- 2018-07-09 HK HK18108881.5A patent/HK1249050B/en unknown
-
2019
- 2019-01-15 IL IL264259A patent/IL264259A/en unknown
- 2019-02-06 JP JP2019019345A patent/JP2019108336A/ja active Pending
- 2019-09-12 US US16/569,065 patent/US11419851B2/en active Active
-
2022
- 2022-08-22 US US17/892,833 patent/US20230226021A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20230226021A1 (en) | Oral formulations of pyrrolidine derivatives | |
| HK1249050A1 (en) | Oral formulations of pyrrolidine derivatives | |
| ES2774789T3 (es) | O-Metiloxima de (3Z,5S)-5-(hidroximetil)-1-[(2'-metil-1,1'-bifenil-4-il)carbonil]pirrolidin-3-ona cristalina útil en métodos de tratamiento de estados relacionados con la actividad del OT-R | |
| CA3181126A1 (en) | Synthetic methods for preparation of 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine | |
| PT2595960E (pt) | Sal e solvatos de um derivado de tetra-hidroisoquinolina | |
| JP7241807B2 (ja) | １５β－ヒドロキシ－酢酸オサテロンの結晶多形 | |
| ES2172481B2 (es) | Composicion farmaceutica que contiene citalopram. | |
| ES2351881T3 (es) | Compuestos estrogénicos novedosos, que pueden obtenerse mediante tratamiento térmico de estrógenos conjugados en alta humedad. | |
| ES2291503T3 (es) | Formas pseudopolimorficas de carvedilol. | |
| KR101210693B1 (ko) | 토실산 서플라타스트 결정의 균일성의 평가방법 및 균일한 결정 및 그의 제조방법 | |
| HK40010092A (en) | Oral formulations of pyrrolidine derivatives | |
| HK1228771B (en) | Oral formulations of pyrrolidine derivatives | |
| HK1228771A1 (en) | Oral formulations of pyrrolidine derivatives | |
| WO2026046113A1 (zh) | 一种irak-4降解剂的多晶型 | |
| BR112016013816B1 (pt) | Comprimido dispersível, processo para a preparação de um comprimido dispersível e kit |