CA2297025A1 - Compositions pharmaceutiques a base de polymeres destinees a une administration ciblee d'agents biologiquement actifs - Google Patents
Compositions pharmaceutiques a base de polymeres destinees a une administration ciblee d'agents biologiquement actifs Download PDFInfo
- Publication number
- CA2297025A1 CA2297025A1 CA002297025A CA2297025A CA2297025A1 CA 2297025 A1 CA2297025 A1 CA 2297025A1 CA 002297025 A CA002297025 A CA 002297025A CA 2297025 A CA2297025 A CA 2297025A CA 2297025 A1 CA2297025 A1 CA 2297025A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- polymeric
- serotonin
- construct
- polymer
- 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.)
- Abandoned
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 70
- 239000013543 active substance Substances 0.000 title claims abstract description 38
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 16
- 239000011159 matrix material Substances 0.000 claims abstract description 31
- 229920001577 copolymer Polymers 0.000 claims abstract description 23
- 241000124008 Mammalia Species 0.000 claims abstract description 15
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 177
- 229940076279 serotonin Drugs 0.000 claims description 83
- -1 poly(lactic acid) Polymers 0.000 claims description 74
- 150000001412 amines Chemical class 0.000 claims description 46
- 230000000035 biogenic effect Effects 0.000 claims description 42
- 229920001661 Chitosan Polymers 0.000 claims description 23
- SJBOEHIKNDEHHO-UHFFFAOYSA-N 2-[2-aminoethyl(carboxymethyl)amino]acetic acid Chemical class NCCN(CC(O)=O)CC(O)=O SJBOEHIKNDEHHO-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 239000000952 serotonin receptor agonist Substances 0.000 claims description 17
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical class OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 16
- 108010088751 Albumins Proteins 0.000 claims description 15
- 102000009027 Albumins Human genes 0.000 claims description 15
- 230000008685 targeting Effects 0.000 claims description 14
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 235000001014 amino acid Nutrition 0.000 claims description 10
- 229940024606 amino acid Drugs 0.000 claims description 10
- 229930195712 glutamate Natural products 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 235000013922 glutamic acid Nutrition 0.000 claims description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 235000003704 aspartic acid Nutrition 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- UDUSOMRJOPCWHT-UHFFFAOYSA-N disofenin Chemical group CC(C)C1=CC=CC(C(C)C)=C1NC(=O)CN(CC(O)=O)CC(O)=O UDUSOMRJOPCWHT-UHFFFAOYSA-N 0.000 claims description 7
- 210000004185 liver Anatomy 0.000 claims description 6
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 claims description 5
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 5
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 claims description 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004472 Lysine Substances 0.000 claims description 5
- 239000004220 glutamic acid Substances 0.000 claims description 5
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 claims description 4
- 229920002305 Schizophyllan Polymers 0.000 claims description 4
- 150000001510 aspartic acids Chemical class 0.000 claims description 4
- 150000002307 glutamic acids Chemical class 0.000 claims description 4
- 210000003494 hepatocyte Anatomy 0.000 claims description 4
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N noradrenaline Chemical compound NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 229920001285 xanthan gum Polymers 0.000 claims description 4
- 239000000230 xanthan gum Substances 0.000 claims description 4
- 235000010493 xanthan gum Nutrition 0.000 claims description 4
- 229940082509 xanthan gum Drugs 0.000 claims description 4
- 229930182837 (R)-adrenaline Natural products 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229920002230 Pectic acid Polymers 0.000 claims description 3
- 229920001710 Polyorthoester Polymers 0.000 claims description 3
- 239000000150 Sympathomimetic Substances 0.000 claims description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 3
- 229960004373 acetylcholine Drugs 0.000 claims description 3
- 239000003833 bile salt Substances 0.000 claims description 3
- 229940093761 bile salts Drugs 0.000 claims description 3
- 239000002872 contrast media Substances 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 229960005139 epinephrine Drugs 0.000 claims description 3
- 229920001308 poly(aminoacid) Polymers 0.000 claims description 3
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 3
- 239000010318 polygalacturonic acid Substances 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 2
- LXUKTWZYHRVQQL-HNNXBMFYSA-N (2S)-2-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methylideneamino]-3-phenylpropanoic acid Chemical compound Cc1ncc(CO)c(C=N[C@@H](Cc2ccccc2)C(O)=O)c1O LXUKTWZYHRVQQL-HNNXBMFYSA-N 0.000 claims description 2
- KDIGYCWRAAYWTQ-JTQLQIEISA-N (2S)-2-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methylideneamino]pentanedioic acid Chemical compound C(C=1C(CO)=CN=C(C)C=1O)=N[C@@H](CCC(=O)O)C(=O)O KDIGYCWRAAYWTQ-JTQLQIEISA-N 0.000 claims description 2
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims description 2
- XMENKXFLWCNNNV-UHFFFAOYSA-N 1h-benzimidazole;2-[carboxymethyl(methyl)amino]acetic acid Chemical compound C1=CC=C2NC=NC2=C1.OC(=O)CN(C)CC(O)=O XMENKXFLWCNNNV-UHFFFAOYSA-N 0.000 claims description 2
- DHPPAEHXIRAWPY-UHFFFAOYSA-N 2-[(2-acetylnaphthalen-1-yl)-(carboxymethyl)amino]acetic acid Chemical compound C1=CC=CC2=C(N(CC(O)=O)CC(O)=O)C(C(=O)C)=CC=C21 DHPPAEHXIRAWPY-UHFFFAOYSA-N 0.000 claims description 2
- GCBNPHYPETXYJJ-UHFFFAOYSA-N 2-[[2-(2-butylanilino)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical group CCCCC1=CC=CC=C1NC(=O)CN(CC(O)=O)CC(O)=O GCBNPHYPETXYJJ-UHFFFAOYSA-N 0.000 claims description 2
- XNORVCNKXNZYSE-UHFFFAOYSA-N 2-[[2-(3-butoxyanilino)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical group CCCCOC1=CC=CC(NC(=O)CN(CC(O)=O)CC(O)=O)=C1 XNORVCNKXNZYSE-UHFFFAOYSA-N 0.000 claims description 2
- XSYSSUAGVNOMCE-UHFFFAOYSA-N 2-[[2-(4-butylanilino)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical group CCCCC1=CC=C(NC(=O)CN(CC(O)=O)CC(O)=O)C=C1 XSYSSUAGVNOMCE-UHFFFAOYSA-N 0.000 claims description 2
- OVRQCZURNANBSK-UHFFFAOYSA-N 2-[[2-(4-tert-butylanilino)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical group CC(C)(C)C1=CC=C(NC(=O)CN(CC(O)=O)CC(O)=O)C=C1 OVRQCZURNANBSK-UHFFFAOYSA-N 0.000 claims description 2
- QHKMTHBQSIKVAC-UHFFFAOYSA-N 2-[[5-[1-[3-[[bis(carboxymethyl)amino]methyl]-4-hydroxyphenyl]-3-oxo-2-benzofuran-1-yl]-2-hydroxyphenyl]methyl-(carboxymethyl)amino]acetic acid Chemical compound C1=C(O)C(CN(CC(O)=O)CC(=O)O)=CC(C2(C3=CC=CC=C3C(=O)O2)C=2C=C(CN(CC(O)=O)CC(O)=O)C(O)=CC=2)=C1 QHKMTHBQSIKVAC-UHFFFAOYSA-N 0.000 claims description 2
- AIYRRERVRZFPKN-UHFFFAOYSA-N 2-[carboxymethyl-[2-(2,3-dimethylanilino)-2-oxoethyl]amino]acetic acid Chemical group CC1=CC=CC(NC(=O)CN(CC(O)=O)CC(O)=O)=C1C AIYRRERVRZFPKN-UHFFFAOYSA-N 0.000 claims description 2
- WNIDXAKKFOKNEF-UHFFFAOYSA-N 2-[carboxymethyl-[2-(2,6-diethylanilino)-2-oxoethyl]amino]acetic acid Chemical group CCC1=CC=CC(CC)=C1NC(=O)CN(CC(O)=O)CC(O)=O WNIDXAKKFOKNEF-UHFFFAOYSA-N 0.000 claims description 2
- OVMLLDXAYBWFBC-UHFFFAOYSA-N 2-[carboxymethyl-[2-(2-hexoxyanilino)-2-oxoethyl]amino]acetic acid Chemical group CCCCCCOC1=CC=CC=C1NC(=O)CN(CC(O)=O)CC(O)=O OVMLLDXAYBWFBC-UHFFFAOYSA-N 0.000 claims description 2
- BVXRFBZNNRXJGR-UHFFFAOYSA-N 2-[carboxymethyl-[2-[(3-cyano-4,5-dimethyl-1h-pyrrol-2-yl)amino]-2-oxoethyl]amino]acetic acid Chemical compound CC=1NC(NC(=O)CN(CC(O)=O)CC(O)=O)=C(C#N)C=1C BVXRFBZNNRXJGR-UHFFFAOYSA-N 0.000 claims description 2
- XFQYOFLFNKCHLG-UHFFFAOYSA-N 3-acetyl-6-bromochromen-2-one Chemical group BrC1=CC=C2OC(=O)C(C(=O)C)=CC2=C1 XFQYOFLFNKCHLG-UHFFFAOYSA-N 0.000 claims description 2
- FPTRWYHXARAFPO-UHFFFAOYSA-N Iprofenin Chemical group CC(C)C1=CC=C(NC(=O)CN(CC(O)=O)CC(O)=O)C=C1 FPTRWYHXARAFPO-UHFFFAOYSA-N 0.000 claims description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 2
- SULVSHBBSDLJAM-UHFFFAOYSA-N N=C1C=C2C=CC=CC2=C(C(C(O)=O)C(O)=O)C1C(=O)C1C(=N)C=C2C=CC=CC2=C1C(C(O)=O)C(=O)O Chemical class N=C1C=C2C=CC=CC2=C(C(C(O)=O)C(O)=O)C1C(=O)C1C(=N)C=C2C=CC=CC2=C1C(C(O)=O)C(=O)O SULVSHBBSDLJAM-UHFFFAOYSA-N 0.000 claims description 2
- 229920000954 Polyglycolide Polymers 0.000 claims description 2
- 229940100389 Sulfonylurea Drugs 0.000 claims description 2
- 239000004098 Tetracycline Substances 0.000 claims description 2
- RGHRJBIKIYUHEV-SGPDEFQSSA-N Thyroxine glucuronide Chemical compound IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC(C=C1I)=CC(I)=C1OC1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O1 RGHRJBIKIYUHEV-SGPDEFQSSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 2
- ARIFZLJIERKKEL-SNNHKCHZSA-N [(z)-[(1e)-1-(carbamothioylhydrazinylidene)-3-ethoxybutan-2-ylidene]amino]thiourea Chemical compound CCOC(C)\C(=N/NC(N)=S)\C=N\NC(N)=S ARIFZLJIERKKEL-SNNHKCHZSA-N 0.000 claims description 2
- FFINMCNLQNTKLU-UHFFFAOYSA-N adipiodone Chemical compound OC(=O)C1=C(I)C=C(I)C(NC(=O)CCCCC(=O)NC=2C(=C(C(O)=O)C(I)=CC=2I)I)=C1I FFINMCNLQNTKLU-UHFFFAOYSA-N 0.000 claims description 2
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 claims description 2
- GHAFORRTMVIXHS-UHFFFAOYSA-L bromosulfophthalein sodium Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(O)=CC=C1C1(C=2C=C(C(O)=CC=2)S([O-])(=O)=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C(=O)O1 GHAFORRTMVIXHS-UHFFFAOYSA-L 0.000 claims description 2
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 claims description 2
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 claims description 2
- 229960001340 histamine Drugs 0.000 claims description 2
- 229960002474 hydralazine Drugs 0.000 claims description 2
- 229960004657 indocyanine green Drugs 0.000 claims description 2
- MOFVSTNWEDAEEK-UHFFFAOYSA-M indocyanine green Chemical compound [Na+].[O-]S(=O)(=O)CCCCN1C2=CC=C3C=CC=CC3=C2C(C)(C)C1=CC=CC=CC=CC1=[N+](CCCCS([O-])(=O)=O)C2=CC=C(C=CC=C3)C3=C2C1(C)C MOFVSTNWEDAEEK-UHFFFAOYSA-M 0.000 claims description 2
- 229940029355 iodipamide Drugs 0.000 claims description 2
- 229960004876 ioglycamic acid Drugs 0.000 claims description 2
- FZDZULUFHNDEDJ-UHFFFAOYSA-N ioglycamic acid Chemical compound OC(=O)C1=C(I)C=C(I)C(NC(=O)COCC(=O)NC=2C(=C(C(O)=O)C(I)=CC=2I)I)=C1I FZDZULUFHNDEDJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960000310 isoleucine Drugs 0.000 claims description 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 2
- MHPZZZZLAQGTHT-UHFFFAOYSA-N mebrofenin Chemical compound CC1=CC(C)=C(NC(=O)CN(CC(O)=O)CC(O)=O)C(C)=C1Br MHPZZZZLAQGTHT-UHFFFAOYSA-N 0.000 claims description 2
- 229960001428 mercaptopurine Drugs 0.000 claims description 2
- 229960002748 norepinephrine Drugs 0.000 claims description 2
- 229960001639 penicillamine Drugs 0.000 claims description 2
- 229960005382 phenolphthalein Drugs 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 229940081623 rose bengal Drugs 0.000 claims description 2
- 229930187593 rose bengal Natural products 0.000 claims description 2
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 claims description 2
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 claims description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 2
- 229960002180 tetracycline Drugs 0.000 claims description 2
- 229930101283 tetracycline Natural products 0.000 claims description 2
- 235000019364 tetracycline Nutrition 0.000 claims description 2
- 150000003522 tetracyclines Chemical class 0.000 claims description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims description 2
- 229950003937 tolonium Drugs 0.000 claims description 2
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 claims description 2
- XBBDACCLCFWBSI-UHFFFAOYSA-N methyl 2-amino-3-(3,4-dihydroxyphenyl)propanoate Chemical compound COC(=O)C(N)CC1=CC=C(O)C(O)=C1 XBBDACCLCFWBSI-UHFFFAOYSA-N 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- PAYYOEIKGWDQKN-UHFFFAOYSA-N 2-[[2-(3-butylanilino)-2-oxoethyl]-(carboxymethyl)amino]acetic acid Chemical group CCCCC1=CC=CC(NC(=O)CN(CC(O)=O)CC(O)=O)=C1 PAYYOEIKGWDQKN-UHFFFAOYSA-N 0.000 claims 1
- IYPHTGWJAAENCL-UHFFFAOYSA-N 2-[carboxymethyl-[2-(4-hexoxyanilino)-2-oxoethyl]amino]acetic acid Chemical group CCCCCCOC1=CC=C(NC(=O)CN(CC(O)=O)CC(O)=O)C=C1 IYPHTGWJAAENCL-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- 230000001975 sympathomimetic effect Effects 0.000 claims 1
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- 239000000706 filtrate Substances 0.000 description 28
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- MDIGAZPGKJFIAH-UHFFFAOYSA-N Serotonin hydrochloride Chemical compound Cl.C1=C(O)C=C2C(CCN)=CNC2=C1 MDIGAZPGKJFIAH-UHFFFAOYSA-N 0.000 description 24
- 230000000717 retained effect Effects 0.000 description 19
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- 230000003993 interaction Effects 0.000 description 15
- 238000009472 formulation Methods 0.000 description 13
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000007995 HEPES buffer Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 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 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 239000011259 mixed solution Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
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- 239000001509 sodium citrate Substances 0.000 description 1
- 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 1
- DCQXTYAFFMSNNH-UHFFFAOYSA-M sodium;2-[bis(2-hydroxyethyl)amino]ethanol;acetate Chemical compound [Na+].CC([O-])=O.OCCN(CCO)CCO DCQXTYAFFMSNNH-UHFFFAOYSA-M 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
Classifications
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- 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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/417—Imidazole-alkylamines, e.g. histamine, phentolamine
-
- 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
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
-
- 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
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Cette invention concerne une construction polymère permettant d'administrer un agent biologiquement actif à un mammifère, laquelle construction comprend une première matrice polymère, un agent biologiquement actif contenu dans la matrice polymère et un second polymère chimiquement lié à l'agent biologiquement actif, ledit second polymère comprenant un copolymère d'acides aminés, ledit second polymère étant présent selon une dose efficace, pour réduire la fuite de l'agent actif de la construction polymère avant l'administration à l'emplacement voulu.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5372997P | 1997-07-25 | 1997-07-25 | |
US60/053,729 | 1997-07-25 | ||
PCT/US1998/015457 WO1999004824A1 (fr) | 1997-07-25 | 1998-07-24 | Compositions pharmaceutiques a base de polymeres destinees a une administration ciblee d'agents biologiquement actifs |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2297025A1 true CA2297025A1 (fr) | 1999-02-04 |
Family
ID=21986168
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002297025A Abandoned CA2297025A1 (fr) | 1997-07-25 | 1998-07-24 | Compositions pharmaceutiques a base de polymeres destinees a une administration ciblee d'agents biologiquement actifs |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0999855A1 (fr) |
JP (1) | JP2001510811A (fr) |
CN (1) | CN1264310A (fr) |
AU (1) | AU8591298A (fr) |
CA (1) | CA2297025A1 (fr) |
WO (1) | WO1999004824A1 (fr) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4586022B2 (ja) | 2003-09-29 | 2010-11-24 | 日東電工株式会社 | インビボポリヌクレオチド送達用生分解性ポリアセタール |
US7674452B2 (en) | 2005-03-16 | 2010-03-09 | Nitto Denko Corporation | Polymer coating of cells |
US7588754B2 (en) | 2005-05-10 | 2009-09-15 | Nitto Denko Corporation | Biodegradable polyacetals and methods |
WO2018140834A1 (fr) * | 2017-01-27 | 2018-08-02 | Cornell University | Polymères et hydrogels modifiés de manière zwitterionique |
US10611857B2 (en) | 2017-08-02 | 2020-04-07 | Exxonmobil Chemical Patents Inc. | Bisphenolate transition metal complexes, production and use thereof |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3360633D1 (en) * | 1982-02-12 | 1985-10-03 | Unitika Ltd | Anti-cancer device |
SE8804164A0 (sv) * | 1988-11-17 | 1990-05-18 | Per Prisell | Farmaceutisk beredning |
CA2046830C (fr) * | 1990-07-19 | 1999-12-14 | Patrick P. Deluca | Systeme d'administration des medicaments comprenant une interaction entre une proteine ou une polypeptide et un polymere hydrophobe biodegradable |
WO1994011015A1 (fr) * | 1992-11-12 | 1994-05-26 | Molecular Dynamics, Inc. | Porteurs lipophiles a base de peptides destines a l'administration ciblee de medicaments selon un concept rationnel de fixation des medicaments |
WO1995000547A1 (fr) * | 1993-06-22 | 1995-01-05 | E.I. Du Pont De Nemours And Company | Composition antimicrobienne comprenant un polymere et un peptide formant des helices amphiphiles du type magainine |
AU3275595A (en) * | 1994-08-05 | 1996-03-04 | Molecular/Structural Biotechnologies, Inc. | Site-specific biomolecular complexes |
-
1998
- 1998-07-24 JP JP2000503875A patent/JP2001510811A/ja active Pending
- 1998-07-24 CA CA002297025A patent/CA2297025A1/fr not_active Abandoned
- 1998-07-24 EP EP98937127A patent/EP0999855A1/fr not_active Withdrawn
- 1998-07-24 WO PCT/US1998/015457 patent/WO1999004824A1/fr not_active Application Discontinuation
- 1998-07-24 AU AU85912/98A patent/AU8591298A/en not_active Abandoned
- 1998-07-24 CN CN 98807413 patent/CN1264310A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
EP0999855A1 (fr) | 2000-05-17 |
WO1999004824A1 (fr) | 1999-02-04 |
AU8591298A (en) | 1999-02-16 |
CN1264310A (zh) | 2000-08-23 |
JP2001510811A (ja) | 2001-08-07 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |