AU2001228721A1 - Compositions of N-(methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridyl-sulfonamide and cyclic oligosaccharides - Google Patents
Compositions of N-(methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridyl-sulfonamide and cyclic oligosaccharidesInfo
- Publication number
- AU2001228721A1 AU2001228721A1 AU2001228721A AU2872101A AU2001228721A1 AU 2001228721 A1 AU2001228721 A1 AU 2001228721A1 AU 2001228721 A AU2001228721 A AU 2001228721A AU 2872101 A AU2872101 A AU 2872101A AU 2001228721 A1 AU2001228721 A1 AU 2001228721A1
- Authority
- AU
- Australia
- Prior art keywords
- cyclodextrin
- torasemide
- derivatives
- cyclodextrins
- alkyl
- 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
- -1 cyclic oligosaccharides Chemical class 0.000 title claims description 30
- 239000000203 mixture Substances 0.000 title claims description 13
- 229920001542 oligosaccharide Polymers 0.000 title description 4
- KMYFTLHVDUDUPD-UHFFFAOYSA-N 1-ethyl-1-methyl-3-[4-(3-methylanilino)pyridin-3-yl]sulfonylurea Chemical group CCN(C)C(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 KMYFTLHVDUDUPD-UHFFFAOYSA-N 0.000 title 1
- 229920000858 Cyclodextrin Polymers 0.000 claims description 114
- NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 claims description 61
- 229960005461 torasemide Drugs 0.000 claims description 59
- 238000012986 modification Methods 0.000 claims description 43
- 230000004048 modification Effects 0.000 claims description 43
- 229960004853 betadex Drugs 0.000 claims description 41
- 239000001116 FEMA 4028 Substances 0.000 claims description 40
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 39
- 229940097362 cyclodextrins Drugs 0.000 claims description 35
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 34
- 239000006069 physical mixture Substances 0.000 claims description 30
- 239000013543 active substance Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 19
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 206010006451 bronchitis Diseases 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- 238000004108 freeze drying Methods 0.000 claims description 8
- 208000028867 ischemia Diseases 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 235000010980 cellulose Nutrition 0.000 claims description 6
- 239000002934 diuretic Substances 0.000 claims description 6
- 230000001882 diuretic effect Effects 0.000 claims description 6
- 238000001694 spray drying Methods 0.000 claims description 6
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims description 5
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 5
- QGKBSGBYSPTPKJ-UZMKXNTCSA-N 2,6-di-o-methyl-β-cyclodextrin Chemical compound COC[C@H]([C@H]([C@@H]([C@H]1OC)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O[C@H]3O[C@H](COC)[C@H]([C@@H]([C@H]3OC)O)O3)[C@H](O)[C@H]2OC)COC)O[C@@H]1O[C@H]1[C@H](O)[C@@H](OC)[C@@H]3O[C@@H]1COC QGKBSGBYSPTPKJ-UZMKXNTCSA-N 0.000 claims description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 206010048962 Brain oedema Diseases 0.000 claims description 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 206010010254 Concussion Diseases 0.000 claims description 4
- 208000016998 Conn syndrome Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 4
- 229920000881 Modified starch Polymers 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 206010037423 Pulmonary oedema Diseases 0.000 claims description 4
- 206010039808 Secondary aldosteronism Diseases 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 230000005856 abnormality Effects 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 239000013566 allergen Substances 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 208000006752 brain edema Diseases 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
- 230000003683 cardiac damage Effects 0.000 claims description 4
- 208000007451 chronic bronchitis Diseases 0.000 claims description 4
- 230000009514 concussion Effects 0.000 claims description 4
- 230000001037 epileptic effect Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 210000005003 heart tissue Anatomy 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 230000004410 intraocular pressure Effects 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 claims description 4
- 230000002503 metabolic effect Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 235000019426 modified starch Nutrition 0.000 claims description 4
- 208000013846 primary aldosteronism Diseases 0.000 claims description 4
- 208000005333 pulmonary edema Diseases 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 230000000451 tissue damage Effects 0.000 claims description 4
- 231100000827 tissue damage Toxicity 0.000 claims description 4
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 230000000181 anti-adherent effect Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000033228 biological regulation Effects 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000004570 mortar (masonry) Substances 0.000 claims description 2
- 238000007738 vacuum evaporation Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 2
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims 1
- 238000000265 homogenisation Methods 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 33
- 238000004090 dissolution Methods 0.000 description 23
- 239000008247 solid mixture Substances 0.000 description 13
- 238000002329 infrared spectrum Methods 0.000 description 12
- 239000000843 powder Substances 0.000 description 10
- 229960000965 nimesulide Drugs 0.000 description 8
- HYWYRSMBCFDLJT-UHFFFAOYSA-N nimesulide Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1=CC=CC=C1 HYWYRSMBCFDLJT-UHFFFAOYSA-N 0.000 description 8
- 229960004535 oxazepam Drugs 0.000 description 7
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000536 complexating effect Effects 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229960001259 diclofenac Drugs 0.000 description 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 2
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- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 2
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- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 2
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- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 2
- 229960001180 norfloxacin Drugs 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
- OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 description 1
- TYNLGDBUJLVSMA-UHFFFAOYSA-N 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid Chemical compound O=C1C2=CC(C(O)=O)=CC(OC(C)=O)=C2C(=O)C2=C1C=CC=C2OC(=O)C TYNLGDBUJLVSMA-UHFFFAOYSA-N 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
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- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
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- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000002171 loop diuretic Substances 0.000 description 1
- 229960004391 lorazepam Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960004296 megestrol acetate Drugs 0.000 description 1
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
- 229960002509 miconazole Drugs 0.000 description 1
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- TZGBBMBARSFJBG-UKTHLTGXSA-N naftazone Chemical compound C1=CC=C2C(=O)C(=N/NC(=O)N)/C=CC2=C1 TZGBBMBARSFJBG-UKTHLTGXSA-N 0.000 description 1
- 229960001556 naftazone Drugs 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229960003642 nicergoline Drugs 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000002464 physical blending Methods 0.000 description 1
- 239000000590 phytopharmaceutical Substances 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- PTTPUWGBPLLBKW-UHFFFAOYSA-M sodium;2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound [Na+].CC(C)CC1=CC=C(C(C)C([O-])=O)C=C1 PTTPUWGBPLLBKW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/724—Cyclodextrins
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- 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
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Nanotechnology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR20000765A HRP20000765A2 (en) | 2000-11-10 | 2000-11-10 | Compositions of n-(1-methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridylsulfonamide and cyclic oligosaccharides with increased release |
| HRP20000765A | 2000-11-10 | ||
| PCT/HR2001/000004 WO2002038186A1 (en) | 2000-11-10 | 2001-01-31 | Compositions of n-(methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridylsulfonamide and cyclic oligosaccharides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001228721A1 true AU2001228721A1 (en) | 2002-05-21 |
Family
ID=10947206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001228721A Abandoned AU2001228721A1 (en) | 2000-11-10 | 2001-01-31 | Compositions of N-(methylethylaminocarbonyl)-4-(3-methylphenylamino)-3-pyridyl-sulfonamide and cyclic oligosaccharides |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US7037928B2 (hu) |
| EP (1) | EP1347780B1 (hu) |
| JP (1) | JP2004513155A (hu) |
| KR (1) | KR20030060929A (hu) |
| CN (1) | CN1477977A (hu) |
| AR (1) | AR026815A1 (hu) |
| AU (1) | AU2001228721A1 (hu) |
| BG (1) | BG107896A (hu) |
| BR (1) | BR0115281A (hu) |
| CA (1) | CA2428179A1 (hu) |
| CZ (1) | CZ20031490A3 (hu) |
| DE (1) | DE60125828T2 (hu) |
| EA (1) | EA005111B1 (hu) |
| EE (1) | EE200300197A (hu) |
| GE (1) | GEP20043403B (hu) |
| HR (1) | HRP20000765A2 (hu) |
| HU (1) | HUP0400776A2 (hu) |
| IL (1) | IL155818A0 (hu) |
| IS (1) | IS6810A (hu) |
| MX (1) | MXPA03004111A (hu) |
| NO (1) | NO20032091L (hu) |
| PL (1) | PL361667A1 (hu) |
| SK (1) | SK6722003A3 (hu) |
| WO (1) | WO2002038186A1 (hu) |
| YU (1) | YU35303A (hu) |
| ZA (1) | ZA200303601B (hu) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI21703A (en) * | 2004-01-14 | 2005-08-31 | Lek Farmacevtska Druzba Dd | Inclusion complexes of perindopril, procedure of their preparation, pharmaceutical compositions containing these complexes and their application in treatment of hypertensia |
| DE602005002930T2 (de) * | 2004-01-22 | 2008-07-24 | Pfizer Inc. | Sulfonamidderivate zur behandlung von krankheiten |
| CN100372534C (zh) * | 2006-04-20 | 2008-03-05 | 南京海辰药业有限公司 | 托拉塞米冻干制剂及制备方法 |
| EP2591783A1 (en) | 2007-04-13 | 2013-05-15 | Millennium Pharmaceuticals, Inc. | Combination anticoagulant therapy with a compound that acts as a factor Xa inhibitor |
| BR102012009317B1 (pt) * | 2012-04-20 | 2022-05-31 | Universidade Federal De Minas Gerais - Ufmg | Processo de preparação de compostos de inclusão envolvendo ciclodextrinas e fármacos, usando um sistema de fluxo contínuo |
| WO2020141224A1 (en) | 2019-01-04 | 2020-07-09 | Sq Innovation Ag | Pharmaceutical compositions of furosemide and uses thereof |
| EP3906020A1 (en) * | 2019-01-04 | 2021-11-10 | SQ Innovation AG | Pharmaceutical compositions of torsemide and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US576511A (en) * | 1897-02-02 | Georg steinike and friedrich schmidt | ||
| DE3529529A1 (de) * | 1985-08-17 | 1987-02-19 | Boehringer Mannheim Gmbh | Verfahren zur herstellung einer stabilen modifikation von torasemid |
| WO1997021312A2 (en) * | 1995-12-01 | 1997-06-12 | Philips Electronics N.V. | A digital cordless telephony system, a radio base station, and a combination of a radio base station and a cordless handset |
| US6828334B2 (en) * | 2002-05-23 | 2004-12-07 | Usv Limited | Fenofibrate-cyclodextrin inclusion complexes and their pharmaceutical composition |
-
2000
- 2000-11-10 HR HR20000765A patent/HRP20000765A2/hr not_active Application Discontinuation
-
2001
- 2001-01-09 AR ARP010100079A patent/AR026815A1/es not_active Application Discontinuation
- 2001-01-31 SK SK672-2003A patent/SK6722003A3/sk unknown
- 2001-01-31 AU AU2001228721A patent/AU2001228721A1/en not_active Abandoned
- 2001-01-31 MX MXPA03004111A patent/MXPA03004111A/es unknown
- 2001-01-31 JP JP2002540768A patent/JP2004513155A/ja active Pending
- 2001-01-31 EE EEP200300197A patent/EE200300197A/xx unknown
- 2001-01-31 KR KR10-2003-7006357A patent/KR20030060929A/ko not_active Application Discontinuation
- 2001-01-31 CZ CZ20031490A patent/CZ20031490A3/cs unknown
- 2001-01-31 WO PCT/HR2001/000004 patent/WO2002038186A1/en active IP Right Grant
- 2001-01-31 HU HU0400776A patent/HUP0400776A2/hu unknown
- 2001-01-31 ZA ZA200303601A patent/ZA200303601B/xx unknown
- 2001-01-31 YU YU35303A patent/YU35303A/sh unknown
- 2001-01-31 DE DE60125828T patent/DE60125828T2/de not_active Expired - Fee Related
- 2001-01-31 BR BR0115281-5A patent/BR0115281A/pt not_active IP Right Cessation
- 2001-01-31 PL PL01361667A patent/PL361667A1/xx unknown
- 2001-01-31 US US10/416,303 patent/US7037928B2/en not_active Expired - Fee Related
- 2001-01-31 CA CA002428179A patent/CA2428179A1/en not_active Abandoned
- 2001-01-31 GE GE5156A patent/GEP20043403B/en unknown
- 2001-01-31 EP EP01993478A patent/EP1347780B1/en not_active Expired - Lifetime
- 2001-01-31 EA EA200300556A patent/EA005111B1/ru not_active IP Right Cessation
- 2001-01-31 CN CNA018198309A patent/CN1477977A/zh active Pending
- 2001-01-31 IL IL15581801A patent/IL155818A0/xx unknown
-
2003
- 2003-05-08 IS IS6810A patent/IS6810A/is unknown
- 2003-05-09 NO NO20032091A patent/NO20032091L/no not_active Application Discontinuation
- 2003-06-10 BG BG107896A patent/BG107896A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20032091D0 (no) | 2003-05-09 |
| PL361667A1 (en) | 2004-10-04 |
| KR20030060929A (ko) | 2003-07-16 |
| GEP20043403B (en) | 2004-06-10 |
| EP1347780B1 (en) | 2007-01-03 |
| EA200300556A1 (ru) | 2003-08-28 |
| DE60125828D1 (de) | 2007-02-15 |
| MXPA03004111A (es) | 2004-05-05 |
| JP2004513155A (ja) | 2004-04-30 |
| BG107896A (bg) | 2004-01-30 |
| DE60125828T2 (de) | 2007-08-16 |
| HUP0400776A2 (hu) | 2004-08-30 |
| CA2428179A1 (en) | 2002-05-16 |
| YU35303A (sh) | 2006-03-03 |
| ZA200303601B (en) | 2004-07-19 |
| CZ20031490A3 (cs) | 2003-08-13 |
| EE200300197A (et) | 2003-08-15 |
| EA005111B1 (ru) | 2004-10-28 |
| WO2002038186A1 (en) | 2002-05-16 |
| IS6810A (is) | 2003-05-08 |
| HRP20000765A2 (en) | 2002-06-30 |
| BR0115281A (pt) | 2003-07-29 |
| US20040039204A1 (en) | 2004-02-26 |
| IL155818A0 (en) | 2003-12-23 |
| SK6722003A3 (en) | 2003-10-07 |
| US7037928B2 (en) | 2006-05-02 |
| CN1477977A (zh) | 2004-02-25 |
| EP1347780A1 (en) | 2003-10-01 |
| NO20032091L (no) | 2003-07-02 |
| AR026815A1 (es) | 2003-02-26 |
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