AU723663C - Aminosterol compounds useful as inhibitors of the sodium/proton exchanger (NHE), pharmaceutical methods and compositions employing such inhibitors, and processes for evaluating the NHE-inhibitory efficacy of compounds - Google Patents
Aminosterol compounds useful as inhibitors of the sodium/proton exchanger (NHE), pharmaceutical methods and compositions employing such inhibitors, and processes for evaluating the NHE-inhibitory efficacy of compoundsInfo
- Publication number
- AU723663C AU723663C AU63349/96A AU6334996A AU723663C AU 723663 C AU723663 C AU 723663C AU 63349/96 A AU63349/96 A AU 63349/96A AU 6334996 A AU6334996 A AU 6334996A AU 723663 C AU723663 C AU 723663C
- Authority
- AU
- Australia
- Prior art keywords
- compound
- cells
- administering
- effective amount
- nhe
- 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.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 484
- 238000000034 method Methods 0.000 title claims abstract description 103
- 239000003112 inhibitor Substances 0.000 title abstract description 51
- 239000011734 sodium Substances 0.000 title abstract description 19
- 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 title abstract description 17
- 229910052708 sodium Inorganic materials 0.000 title abstract description 17
- 239000000203 mixture Substances 0.000 title description 41
- 230000008569 process Effects 0.000 title description 12
- 239000000243 solution Substances 0.000 claims description 113
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- 238000003556 assay Methods 0.000 claims description 53
- 230000012010 growth Effects 0.000 claims description 51
- 210000001519 tissue Anatomy 0.000 claims description 40
- 230000002401 inhibitory effect Effects 0.000 claims description 36
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- UIRKNQLZZXALBI-UHFFFAOYSA-N Squalamine Natural products OC1CC2CC(NCCCNCCCCN)CCC2(C)C2C1C1CCC(C(C)CCC(C(C)C)OS(O)(=O)=O)C1(C)CC2 UIRKNQLZZXALBI-UHFFFAOYSA-N 0.000 description 145
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- 108091006649 SLC9A3 Proteins 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 102100030375 Sodium/hydrogen exchanger 3 Human genes 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
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- 239000002904 solvent Substances 0.000 description 35
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
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- 206010028980 Neoplasm Diseases 0.000 description 26
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
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- 102000001708 Protein Isoforms Human genes 0.000 description 24
- 108010029485 Protein Isoforms Proteins 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- -1 hydrogen ions Chemical class 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
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- 239000012267 brine Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
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- 230000001960 triggered effect Effects 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
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- G01N33/5011—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics for testing antineoplastic activity
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- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5044—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics involving specific cell types
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- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
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- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5082—Supracellular entities, e.g. tissue, organisms
- G01N33/5088—Supracellular entities, e.g. tissue, organisms of vertebrates
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Hematology (AREA)
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- Medicinal Chemistry (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Cell Biology (AREA)
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- Animal Behavior & Ethology (AREA)
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- Tropical Medicine & Parasitology (AREA)
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Applications Claiming Priority (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/483,059 US5840740A (en) | 1995-06-07 | 1995-06-07 | Aminosterol compounds and a method of treating infection using the aminosterol compounds |
| US08/479,455 US5994336A (en) | 1995-06-07 | 1995-06-07 | Method of inhibiting proliferation of cells by administering an aminosterol compound |
| US08/483059 | 1995-06-07 | ||
| US08/476,855 US5874597A (en) | 1995-06-07 | 1995-06-07 | Certain aminosterol compounds and pharmaceutical compositions including these compounds |
| US08/476855 | 1995-06-07 | ||
| US08/479,457 US5763430A (en) | 1995-06-07 | 1995-06-07 | Method of treating a viral infection by administering a steroid compound |
| US08/479457 | 1995-06-07 | ||
| US08/475,572 US5840936A (en) | 1995-06-07 | 1995-06-07 | Aminosterol compounds useful as inhibitors of the sodium/proton exchanger (NHE) |
| US08/483057 | 1995-06-07 | ||
| US08/479455 | 1995-06-07 | ||
| US08/483,057 US5795885A (en) | 1995-06-07 | 1995-06-07 | Method of inhibiting profileration of cells by administering an aminosterol compound |
| US08/487,443 US5847172A (en) | 1995-06-07 | 1995-06-07 | Certain aminosterol compounds and pharmaceutical compositions including these compounds |
| US08/475572 | 1995-06-07 | ||
| US08/487443 | 1995-06-07 | ||
| PCT/US1996/010508 WO1996040728A2 (en) | 1995-06-07 | 1996-06-07 | Aminosterol compounds useful as inhibitors of the sodium/proton exchanger (nhe), pharmaceutical methods and compositions employing such inhibitors, and processes for evaluating the nhe-inhibitory efficacy of compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU6334996A AU6334996A (en) | 1996-12-30 |
| AU723663B2 AU723663B2 (en) | 2000-08-31 |
| AU723663C true AU723663C (en) | 2001-11-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU63349/96A Ceased AU723663C (en) | 1995-06-07 | 1996-06-07 | Aminosterol compounds useful as inhibitors of the sodium/proton exchanger (NHE), pharmaceutical methods and compositions employing such inhibitors, and processes for evaluating the NHE-inhibitory efficacy of compounds |
Country Status (10)
| Country | Link |
|---|---|
| EP (2) | EP0832094B1 (enExample) |
| JP (2) | JP4104164B2 (enExample) |
| AT (1) | ATE259375T1 (enExample) |
| AU (1) | AU723663C (enExample) |
| CA (1) | CA2223910C (enExample) |
| DE (1) | DE69631527T2 (enExample) |
| DK (1) | DK0832094T3 (enExample) |
| ES (1) | ES2216049T3 (enExample) |
| PT (1) | PT832094E (enExample) |
| WO (1) | WO1996040728A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5856535A (en) * | 1994-08-18 | 1999-01-05 | Magainin Pharmaceuticals, Inc. | Aminosterol ester compounds |
| US6143738A (en) * | 1995-06-07 | 2000-11-07 | Magainin Pharmaceuticals, Inc. | Therapeutic uses for an aminosterol compound |
| US5792635A (en) * | 1995-06-07 | 1998-08-11 | Magainin Pharmaceuticals, Inc. | Method of inhibiting the sodium/proton exchanger NHE3 and method of inhibiting growth by administering squalamine |
| PT910382E (pt) * | 1996-04-26 | 2003-10-31 | Genaera Corp | Esqualamina em combinacao com outros agentes anti-cancro para o tratamento de tumores |
| US6596712B2 (en) | 1996-04-26 | 2003-07-22 | Genaera Corporation | Treatment of carcinomas using squalamine in combination with other anti-cancer agents or modalities |
| US7410959B1 (en) * | 2000-07-13 | 2008-08-12 | Genaera Corporation | Therapeutic uses for aminosterol compounds |
| CA2255856C (en) * | 1996-05-17 | 2008-05-13 | Magainin Pharmaceuticals Inc. | Therapeutic uses for an aminosterol compound |
| WO1998019682A1 (en) * | 1996-11-01 | 1998-05-14 | Magainin Pharmaceuticals Inc. | Certain aminosterol compounds and uses therefor |
| US6262283B1 (en) | 1996-12-06 | 2001-07-17 | Magainin Pharmaceuticals Inc. | Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds |
| DE19737463A1 (de) * | 1997-08-28 | 1999-03-04 | Hoechst Marion Roussel De Gmbh | Verwendung von Inhibitoren des Natrium-Wasserstoff-Austauschers zur Herstellung eines Arzneimittels zur Behandlung von Erkrankungen, die durch Protozoen verursacht werden |
| AU5342701A (en) | 2000-04-12 | 2001-10-30 | Genaera Corp | A process for the preparation of 7.alpha.-hydroxy 3-aminosubstituted sterols using intermediates with an unprotected 7.alpha.-hydroxy group |
| WO2006119211A2 (en) * | 2005-05-02 | 2006-11-09 | Genaera Corporation | Methods and compositions for treating ocular disorders |
| AU2007240652A1 (en) * | 2006-04-21 | 2007-11-01 | Genaera Corporation | Induction of weight loss and the selective inhibition of PTP1B |
| CA2985271A1 (en) * | 2007-09-06 | 2009-03-12 | Ohr Pharmaceutical, Inc. | A method for treating diabetes |
| JP5634985B2 (ja) | 2008-05-09 | 2014-12-03 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | インスリン抵抗性およびβ−細胞機能障害に関連する疾患を治療するためのリメポリドを含む医薬組成物 |
| CN103957919B (zh) * | 2011-09-19 | 2018-10-16 | 瑞士苏黎世联邦理工学院 | RORγ调节剂 |
| KR20150003798A (ko) | 2012-04-20 | 2015-01-09 | 오에이치알 파마서티컬, 인코포레이티드 | Ptp1b 연관 질병의 치료용 아미노스테로이드 |
| RU2669800C2 (ru) | 2013-03-15 | 2018-10-16 | Брихэм Янг Юниверсити | Способы лечения воспаления, аутоиммунных расстройств и боли |
| US11524015B2 (en) | 2013-03-15 | 2022-12-13 | Brigham Young University | Methods for treating inflammation, autoimmune disorders and pain |
| EP2781217A1 (en) * | 2013-03-18 | 2014-09-24 | ETH Zurich | ROR gamma modulators |
| US10040817B2 (en) | 2013-10-03 | 2018-08-07 | Enterin Laboratories, Inc. | Methods and compositions for stimulation of the intestinal enteroendocrine system for treating diseases or conditions related to the same |
| 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 |
| US10441595B2 (en) * | 2014-06-26 | 2019-10-15 | Brigham Young University | Methods for treating fungal infections |
| FR3033563B1 (fr) * | 2015-03-12 | 2018-04-13 | Virbac | Composes analogues de la squalamine utiles comme agents antibacteriens |
| FR3055801B1 (fr) * | 2016-09-15 | 2020-10-30 | Virbac | Derives esters de squalamine pour le traitement des infections |
| US11083735B2 (en) | 2017-09-08 | 2021-08-10 | Enterin, Inc. | Methods for treating sleep disorders, sleep disturbances, and related symptoms using aminosterol compositions |
| EP3829587A4 (en) * | 2018-08-03 | 2022-07-20 | Enterin, Inc. | COMPOSITIONS AND METHODS FOR TREATMENT OF BRAIN AND GUESS DISORDERS |
| US11464789B2 (en) | 2018-08-03 | 2022-10-11 | Enterin, Inc. | Aminosterol compositions and methods of using the same for treating schizophrenia |
| US12186328B2 (en) | 2019-05-23 | 2025-01-07 | Brigham Young University | Use of CSA compounds to stimulate stem cells and hair growth |
| CA3149479A1 (en) * | 2019-08-02 | 2021-02-11 | Enterin, Inc. | Human aminosterol ent-03 compounds, related compositions comprising the same, and methods of using the same |
| WO2021025974A1 (en) * | 2019-08-02 | 2021-02-11 | Enterin, Inc. | Human squalamine derivatives, related compositions comprising the same, and methods of using the same |
| CN112782300B (zh) * | 2020-12-25 | 2022-04-12 | 山东省食品药品检验研究院 | 一种胆烷酸的同分异构体及其检测方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993018773A1 (en) * | 1992-03-18 | 1993-09-30 | The Children's Hospital Of Philadelphia | Novel aminosterol antibiotic |
| WO1994020520A1 (en) * | 1993-03-10 | 1994-09-15 | Magainin Pharmaceuticals Inc. | Steroid derivatives, pharmaceutical compositions containing them, and their use as antibiotics or disinfectants |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994019366A1 (en) * | 1993-02-26 | 1994-09-01 | Magainin Pharmaceuticals Inc. | Chemical synthesis of squalamine |
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1996
- 1996-06-07 DK DK96922490T patent/DK0832094T3/da active
- 1996-06-07 EP EP96922490A patent/EP0832094B1/en not_active Expired - Lifetime
- 1996-06-07 CA CA002223910A patent/CA2223910C/en not_active Expired - Lifetime
- 1996-06-07 WO PCT/US1996/010508 patent/WO1996040728A2/en not_active Ceased
- 1996-06-07 ES ES96922490T patent/ES2216049T3/es not_active Expired - Lifetime
- 1996-06-07 AU AU63349/96A patent/AU723663C/en not_active Ceased
- 1996-06-07 EP EP04002943A patent/EP1420027A3/en not_active Withdrawn
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- 1996-06-07 AT AT96922490T patent/ATE259375T1/de not_active IP Right Cessation
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- 1996-06-07 DE DE69631527T patent/DE69631527T2/de not_active Expired - Lifetime
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2007
- 2007-08-29 JP JP2007223309A patent/JP2007314577A/ja not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993018773A1 (en) * | 1992-03-18 | 1993-09-30 | The Children's Hospital Of Philadelphia | Novel aminosterol antibiotic |
| WO1994020520A1 (en) * | 1993-03-10 | 1994-09-15 | Magainin Pharmaceuticals Inc. | Steroid derivatives, pharmaceutical compositions containing them, and their use as antibiotics or disinfectants |
Non-Patent Citations (1)
| Title |
|---|
| STEROIDS, 1993 58:370-78, WEHRLI ET AL * |
Also Published As
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| JP4104164B2 (ja) | 2008-06-18 |
| CA2223910A1 (en) | 1996-12-19 |
| EP0832094B1 (en) | 2004-02-11 |
| WO1996040728A2 (en) | 1996-12-19 |
| JP2007314577A (ja) | 2007-12-06 |
| CA2223910C (en) | 2008-09-16 |
| DE69631527T2 (de) | 2004-09-23 |
| ATE259375T1 (de) | 2004-02-15 |
| ES2216049T3 (es) | 2004-10-16 |
| JP2002515019A (ja) | 2002-05-21 |
| DE69631527D1 (de) | 2004-03-18 |
| AU6334996A (en) | 1996-12-30 |
| EP1420027A2 (en) | 2004-05-19 |
| DK0832094T3 (da) | 2004-05-17 |
| AU723663B2 (en) | 2000-08-31 |
| EP0832094A2 (en) | 1998-04-01 |
| WO1996040728A3 (en) | 1997-03-27 |
| EP1420027A3 (en) | 2012-01-04 |
| PT832094E (pt) | 2004-06-30 |
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