JP5052726B2 - 金属イオンキレートとの胆汁酸複合体及びその使用 - Google Patents
金属イオンキレートとの胆汁酸複合体及びその使用 Download PDFInfo
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- JP5052726B2 JP5052726B2 JP2001564201A JP2001564201A JP5052726B2 JP 5052726 B2 JP5052726 B2 JP 5052726B2 JP 2001564201 A JP2001564201 A JP 2001564201A JP 2001564201 A JP2001564201 A JP 2001564201A JP 5052726 B2 JP5052726 B2 JP 5052726B2
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- Prior art keywords
- amino
- bis
- acid
- carbonyl
- ethyl
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- 229910021645 metal ion Inorganic materials 0.000 title claims abstract description 20
- 239000013522 chelant Substances 0.000 title claims abstract description 7
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 title description 16
- 239000003613 bile acid Substances 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 116
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 52
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 50
- -1 glucamine Chemical compound 0.000 claims description 41
- 125000000267 glycino group Chemical group [H]N([*])C([H])([H])C(=O)O[H] 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- 239000002738 chelating agent Substances 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
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- 238000003384 imaging method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
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- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 7
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 6
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- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 claims description 4
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- 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 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 210000005166 vasculature Anatomy 0.000 claims description 3
- CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 claims description 2
- 229960001091 chenodeoxycholic acid Drugs 0.000 claims description 2
- 210000004351 coronary vessel Anatomy 0.000 claims description 2
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 claims description 2
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- 238000002059 diagnostic imaging Methods 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 claims description 2
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- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 claims description 2
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- 229910052688 Gadolinium Inorganic materials 0.000 description 14
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- 206010015719 Exsanguination Diseases 0.000 description 1
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- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
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- 229930182558 Sterol Natural products 0.000 description 1
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- 239000000443 aerosol Substances 0.000 description 1
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- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
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- QSHQKIURKJITMZ-BRPMRXRMSA-N cholane Chemical group C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCC)[C@@]1(C)CC2 QSHQKIURKJITMZ-BRPMRXRMSA-N 0.000 description 1
- 125000003716 cholic acid group Chemical group 0.000 description 1
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- 229940039231 contrast media Drugs 0.000 description 1
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- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 1
- RYHQMKVRYNEBNJ-BMWGJIJESA-K gadoterate meglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 RYHQMKVRYNEBNJ-BMWGJIJESA-K 0.000 description 1
- GFSTXYOTEVLASN-UHFFFAOYSA-K gadoteric acid Chemical compound [Gd+3].OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 GFSTXYOTEVLASN-UHFFFAOYSA-K 0.000 description 1
- DPNNNPAKRZOSMO-UHFFFAOYSA-K gadoteridol Chemical compound [Gd+3].CC(O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 DPNNNPAKRZOSMO-UHFFFAOYSA-K 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 230000024924 glomerular filtration Effects 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007914 intraventricular administration Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
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- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 238000009206 nuclear medicine Methods 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 239000008363 phosphate buffer Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
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- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2000A000383 | 2000-02-29 | ||
| IT2000MI000383A IT1317862B1 (it) | 2000-02-29 | 2000-02-29 | Coniugati di acidi biliari con chelati complessi di ioni metallici eloro uso. |
| ITMI2000A000383 | 2000-02-29 | ||
| PCT/EP2001/001971 WO2001064708A1 (en) | 2000-02-29 | 2001-02-21 | Bile acids conjugates with metal ion chelates and the use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003525306A JP2003525306A (ja) | 2003-08-26 |
| JP2003525306A5 JP2003525306A5 (https=) | 2008-04-10 |
| JP5052726B2 true JP5052726B2 (ja) | 2012-10-17 |
Family
ID=11444243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001564201A Expired - Fee Related JP5052726B2 (ja) | 2000-02-29 | 2001-02-21 | 金属イオンキレートとの胆汁酸複合体及びその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6803030B2 (https=) |
| EP (1) | EP1259532B1 (https=) |
| JP (1) | JP5052726B2 (https=) |
| AT (1) | ATE294813T1 (https=) |
| AU (1) | AU4064401A (https=) |
| DE (1) | DE60110558T2 (https=) |
| IT (1) | IT1317862B1 (https=) |
| WO (1) | WO2001064708A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1318485B1 (it) * | 2000-04-21 | 2003-08-25 | Bracco Spa | Uso di derivati di acidi biliari coniugati con complessi di ionimetallici nella visualizzazione diagnostica di sistemi microvascolari |
| CA2488819A1 (en) * | 2002-03-28 | 2003-11-06 | Rutgers, The State University Of New Jersey | Bis-transition-metal-chelate-probes |
| US6919333B2 (en) * | 2002-11-12 | 2005-07-19 | Rutgers, The State University Of New Jersey | Bis-transition-metal-chelate probes |
| US7226577B2 (en) * | 2003-01-13 | 2007-06-05 | Bracco Imaging, S. P. A. | Gastrin releasing peptide compounds |
| CA2512310C (en) * | 2003-01-13 | 2012-09-25 | Bracco Imaging S.P.A. | Improved linkers for radiopharmaceutical compounds |
| US7850947B2 (en) | 2003-01-13 | 2010-12-14 | Bracco Imaging S.P.A. | Gastrin releasing peptide compounds |
| US8420050B2 (en) * | 2003-01-13 | 2013-04-16 | Bracco Imaging S.P.A. | Gastrin releasing peptide compounds |
| US7611692B2 (en) * | 2003-01-13 | 2009-11-03 | Bracco Imaging S.P.A. | Gastrin releasing peptide compounds |
| DE102004038134B4 (de) | 2004-08-05 | 2013-07-25 | Johann Wolfgang Goethe-Universität Frankfurt am Main | Multivalente Chelatoren zum Modifizieren und Organisieren von Zielmolekülen, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| JP2008508333A (ja) * | 2004-08-05 | 2008-03-21 | ヨハン ウォルフガング ゲーテ−ウニベルジテート フランクフルト アム マイン | 標的分子の改変および組織化のための多価キレーター |
| WO2006084257A2 (en) * | 2005-02-03 | 2006-08-10 | Epix Pharmaceuticals, Inc. | Steady state perfusion methods |
| EP2147684A1 (en) | 2008-07-22 | 2010-01-27 | Bracco Imaging S.p.A | Diagnostic Agents Selective Against Metalloproteases |
| US11524015B2 (en) | 2013-03-15 | 2022-12-13 | Brigham Young University | Methods for treating inflammation, autoimmune disorders and pain |
| WO2014151411A1 (en) | 2013-03-15 | 2014-09-25 | Brigham Young University | Methods for treating inflammation, autoimmune disorders and pain |
| US11690855B2 (en) | 2013-10-17 | 2023-07-04 | Brigham Young University | Methods for treating lung infections and inflammation |
| US20150203527A1 (en) | 2014-01-23 | 2015-07-23 | Brigham Young University | Cationic steroidal antimicrobials |
| US10227376B2 (en) * | 2014-08-22 | 2019-03-12 | Brigham Young University | Radiolabeled cationic steroid antimicrobials and diagnostic methods |
| EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
| US10226550B2 (en) | 2016-03-11 | 2019-03-12 | Brigham Young University | Cationic steroidal antimicrobial compositions for the treatment of dermal tissue |
| RU2755181C2 (ru) | 2016-11-28 | 2021-09-14 | Байер Фарма Акциенгезельшафт | Новые хелатные соединения гадолиния с высокой релаксивностью для применения в магнитно-резонансной визуализации |
| US10959433B2 (en) | 2017-03-21 | 2021-03-30 | Brigham Young University | Use of cationic steroidal antimicrobials for sporicidal activity |
| CN113164628A (zh) | 2018-11-23 | 2021-07-23 | 拜耳股份有限公司 | 造影介质制剂及其制备方法 |
| US12186328B2 (en) | 2019-05-23 | 2025-01-07 | Brigham Young University | Use of CSA compounds to stimulate stem cells and hair growth |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5057302A (en) * | 1987-02-13 | 1991-10-15 | Abbott Laboratories | Bifunctional chelating agents |
| NO940115D0 (no) * | 1994-01-13 | 1994-01-13 | Nycomed Imaging As | Kontrastmidler for roentgen- og magnettomografisk avbildning |
| GB9407812D0 (en) * | 1994-04-20 | 1994-06-15 | Nycomed Salutar Inc | Compounds |
| IT1269839B (it) * | 1994-05-26 | 1997-04-15 | Bracco Spa | Coniugati di acidi biliari, loro derivati con complessi metallici e relativi usi |
| IT1283218B1 (it) | 1996-03-08 | 1998-04-16 | Bracco Spa | Polichelanti, loro complessi con ioni metallici, loro preparazione e loro usi |
| IT1304501B1 (it) * | 1998-12-23 | 2001-03-19 | Bracco Spa | Uso di derivati di acidi biliari coniugati con complessi metallicicome "blood pool agents" per l'indagine diagnostica tramite risonanza |
-
2000
- 2000-02-29 IT IT2000MI000383A patent/IT1317862B1/it active
-
2001
- 2001-02-21 EP EP01911677A patent/EP1259532B1/en not_active Expired - Lifetime
- 2001-02-21 US US10/220,048 patent/US6803030B2/en not_active Expired - Fee Related
- 2001-02-21 JP JP2001564201A patent/JP5052726B2/ja not_active Expired - Fee Related
- 2001-02-21 WO PCT/EP2001/001971 patent/WO2001064708A1/en not_active Ceased
- 2001-02-21 AT AT01911677T patent/ATE294813T1/de not_active IP Right Cessation
- 2001-02-21 DE DE60110558T patent/DE60110558T2/de not_active Expired - Lifetime
- 2001-02-21 AU AU40644/01A patent/AU4064401A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU4064401A (en) | 2001-09-12 |
| US20030113265A1 (en) | 2003-06-19 |
| ATE294813T1 (de) | 2005-05-15 |
| DE60110558T2 (de) | 2005-09-22 |
| EP1259532A1 (en) | 2002-11-27 |
| ITMI20000383A1 (it) | 2001-08-29 |
| EP1259532B1 (en) | 2005-05-04 |
| IT1317862B1 (it) | 2003-07-15 |
| WO2001064708A1 (en) | 2001-09-07 |
| US6803030B2 (en) | 2004-10-12 |
| DE60110558D1 (de) | 2005-06-09 |
| JP2003525306A (ja) | 2003-08-26 |
| ITMI20000383A0 (it) | 2000-02-29 |
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