US20180065992A1 - Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same - Google Patents
Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same Download PDFInfo
- Publication number
- US20180065992A1 US20180065992A1 US15/699,706 US201715699706A US2018065992A1 US 20180065992 A1 US20180065992 A1 US 20180065992A1 US 201715699706 A US201715699706 A US 201715699706A US 2018065992 A1 US2018065992 A1 US 2018065992A1
- Authority
- US
- United States
- Prior art keywords
- hca
- compound
- monomeric
- subject
- condition
- 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
- LPBKGNZOZQUKAM-UHFFFAOYSA-M [H]C(O)(C(=O)O[Y])C1(O)CC(=O)OCOC1=O Chemical compound [H]C(O)(C(=O)O[Y])C1(O)CC(=O)OCOC1=O LPBKGNZOZQUKAM-UHFFFAOYSA-M 0.000 description 5
- DGDLKTSUUPERAZ-UHFFFAOYSA-N [H]C(O)(C(C)=O)C1(O)CC(=O)OCOC1=O Chemical compound [H]C(O)(C(C)=O)C1(O)CC(=O)OCOC1=O DGDLKTSUUPERAZ-UHFFFAOYSA-N 0.000 description 3
- MXRHPFQGGQNDNY-UHFFFAOYSA-N [H]OC(=O)C(O)C1(O)CC(=O)OCOC1=O Chemical compound [H]OC(=O)C(O)C1(O)CC(=O)OCOC1=O MXRHPFQGGQNDNY-UHFFFAOYSA-N 0.000 description 3
- 0 C=O.[H]C(O)(C(=O)O[K])C1(CC(=O)O[K])O[Ca]OC1=O.[H]C([H])(C(=O)O[K])C1(O)C(=O)O[Ca](O)OC(=O)C1([H])O.[H]C([H])(COO[Ca]OC(=O)C([H])(O)C(O)(C(=O)O[K])C([H])([H])C(=O)O[K])C1(O)O(C=O)[Mg]OC1([H])O Chemical compound C=O.[H]C(O)(C(=O)O[K])C1(CC(=O)O[K])O[Ca]OC1=O.[H]C([H])(C(=O)O[K])C1(O)C(=O)O[Ca](O)OC(=O)C1([H])O.[H]C([H])(COO[Ca]OC(=O)C([H])(O)C(O)(C(=O)O[K])C([H])([H])C(=O)O[K])C1(O)O(C=O)[Mg]OC1([H])O 0.000 description 2
- OZQPTQZKTPHWTE-UHFFFAOYSA-N COC(=O)C(O)C1(O)CC(=O)OCOC1=O Chemical compound COC(=O)C(O)C1(O)CC(=O)OCOC1=O OZQPTQZKTPHWTE-UHFFFAOYSA-N 0.000 description 1
- ZMJBYMUCKBYSCP-UHFFFAOYSA-N [H]C(O)(C(=O)O)C(O)(CC(=O)O)C(=O)O Chemical compound [H]C(O)(C(=O)O)C(O)(CC(=O)O)C(=O)O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 description 1
- QFHBLJOYISJMGJ-UHFFFAOYSA-K [H]C(O)(C(=O)OO[K])C1(O)CC(=O)O[Mg]OC1=O Chemical compound [H]C(O)(C(=O)OO[K])C1(O)CC(=O)O[Mg]OC1=O QFHBLJOYISJMGJ-UHFFFAOYSA-K 0.000 description 1
- HCGJJRADHTUIFJ-UHFFFAOYSA-M [H]C(O)(C(=O)O[K])C1(O)C(=O)OCOC(=O)C1([H])O Chemical compound [H]C(O)(C(=O)O[K])C1(O)C(=O)OCOC(=O)C1([H])O HCGJJRADHTUIFJ-UHFFFAOYSA-M 0.000 description 1
- KRFJAFSLTARWEA-UHFFFAOYSA-N [H]C([H])(C(=O)O)C(O)(C(=O)O)C([H])(O)C(=O)O.[H]C([H])(C(=O)O)C(O)(C(=O)O)C([H])(O)C(=O)O.[H]C([H])(C(=O)O)C(O)(OC=O)C([H])(O)C(=O)O.[H]C([H])(C(=O)O)C(O)(OC=O)C([H])(O)C(=O)O Chemical compound [H]C([H])(C(=O)O)C(O)(C(=O)O)C([H])(O)C(=O)O.[H]C([H])(C(=O)O)C(O)(C(=O)O)C([H])(O)C(=O)O.[H]C([H])(C(=O)O)C(O)(OC=O)C([H])(O)C(=O)O.[H]C([H])(C(=O)O)C(O)(OC=O)C([H])(O)C(=O)O KRFJAFSLTARWEA-UHFFFAOYSA-N 0.000 description 1
- GJAFXVPJBUZERY-UHFFFAOYSA-N [H]C([H])C(=O)OCOC(=O)C(O)C(O)C(=O)[O+]([H-]O)[H-]O.[H][O+]([H])[CH2-].[H][O+]([H])[CH2-].[K+] Chemical compound [H]C([H])C(=O)OCOC(=O)C(O)C(O)C(=O)[O+]([H-]O)[H-]O.[H][O+]([H])[CH2-].[H][O+]([H])[CH2-].[K+] GJAFXVPJBUZERY-UHFFFAOYSA-N 0.000 description 1
- FYUWTCQPFJFFGB-UHFFFAOYSA-N [H]C1([H])C(=O)CCOCC([H])(C(=O)O)C1(O)C(=O)O.[H]C1([H])C(=O)CCOCC([H])(C(=O)O)C1(O)OC=O Chemical compound [H]C1([H])C(=O)CCOCC([H])(C(=O)O)C1(O)C(=O)O.[H]C1([H])C(=O)CCOCC([H])(C(=O)O)C1(O)OC=O FYUWTCQPFJFFGB-UHFFFAOYSA-N 0.000 description 1
- LSBGRRYQDLDLIB-UHFFFAOYSA-L [H]C1([H])C(=O)OCOC(=O)C1(O)C(O)C(=O)[O-].[H]C1([H])C(=O)OCOC(=O)C1(O)C([H])(O)C(=O)O[Y].[H]O.[H]O.[H]O[H].[H]O[H].[Y+] Chemical compound [H]C1([H])C(=O)OCOC(=O)C1(O)C(O)C(=O)[O-].[H]C1([H])C(=O)OCOC(=O)C1(O)C([H])(O)C(=O)O[Y].[H]O.[H]O.[H]O[H].[H]O[H].[Y+] LSBGRRYQDLDLIB-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic System
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/02—Magnesium compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic System without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/699,706 US20180065992A1 (en) | 2016-09-08 | 2017-09-08 | Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same |
| US16/869,097 US11066423B2 (en) | 2016-09-08 | 2020-05-07 | Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662384963P | 2016-09-08 | 2016-09-08 | |
| US15/699,706 US20180065992A1 (en) | 2016-09-08 | 2017-09-08 | Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US16/869,097 Continuation US11066423B2 (en) | 2016-09-08 | 2020-05-07 | Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20180065992A1 true US20180065992A1 (en) | 2018-03-08 |
Family
ID=61281985
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US15/699,706 Abandoned US20180065992A1 (en) | 2016-09-08 | 2017-09-08 | Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same |
| US16/869,097 Active US11066423B2 (en) | 2016-09-08 | 2020-05-07 | Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US16/869,097 Active US11066423B2 (en) | 2016-09-08 | 2020-05-07 | Monomeric bimetal hydroxycitric acid compounds and methods of making and using the same |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US20180065992A1 (fr) |
| EP (1) | EP3509578B1 (fr) |
| CN (1) | CN110087646A (fr) |
| WO (1) | WO2018049216A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023074894A1 (fr) * | 2021-11-01 | 2023-05-04 | 小林製薬株式会社 | Agent pour favoriser la régénération de cartilages |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11292759B2 (en) | 2018-03-07 | 2022-04-05 | Nutrition Research Group, Limited | Hydroxycitric acid metal heterocyclic compounds with covalent characteristics |
| CN115475156A (zh) * | 2022-09-15 | 2022-12-16 | 广州医科大学附属第一医院（广州呼吸中心） | 羟基柠檬酸在制备防治兰德尔斑药物中的应用 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000048983A1 (fr) * | 1999-02-18 | 2000-08-24 | Vittal Mallya Scientific Research Foundation | Sel double soluble de metaux des groupes ia et iia d'acide (-) hydroxycitrique |
| US6160172A (en) * | 1997-08-27 | 2000-12-12 | Vittal Mallya Scientific Research Foundation | Soluble double metal salt of group IA and IIA of (-) hydroxycitric acid, process of preparing the same and its use in beverages and other food products without effecting their flavor and properties |
| WO2005025544A1 (fr) * | 2003-09-11 | 2005-03-24 | Glykon Technologies Group, Llc | Administration enterique d'acide (-)-hydroxycitrique |
| WO2005030195A1 (fr) * | 2003-09-20 | 2005-04-07 | Glykon Technologies Group, Llc | Acide (-)-hydroxycitrique pour retarder la vidange gastrique |
| US20060025482A1 (en) * | 2004-07-29 | 2006-02-02 | Clouatre Dallas L | (-)-Hydroxycitric acid for the modulation of angiotensin-converting enzyme |
| US20080145408A1 (en) * | 2006-12-15 | 2008-06-19 | Alex Moffett | Dimeric Double Metal Salts of (-) Hydroxycitric Acid, Methods of Making and Uses of Same |
| US20110274654A1 (en) * | 2010-05-05 | 2011-11-10 | Bahadoor Adilah | Triazoles as inhibitors of fatty acid synthase |
| JP2014218442A (ja) * | 2013-05-01 | 2014-11-20 | 昭和電工株式会社 | ヒドロキシトリカルボン酸のベンジル化方法 |
| US20180110750A1 (en) * | 2016-10-25 | 2018-04-26 | Glykon Technologies Group, Llc | Hydroxycitric acid compounds and capsule liquid delivery |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1011660A1 (fr) | 1997-07-14 | 2000-06-28 | Inter-Health Nutraceuticals Incorporated | Compositions d'acide hydroxycitrique, complements alimentaires et pharmaceutiques et produits alimentaires fabriques a partir de ces compositions, et procede d'utilisation de tels produits pour la reduction du poids corporel |
| US6287607B2 (en) * | 1999-07-19 | 2001-09-11 | Mission Pharmacal Company | Potassium calcium citrate compositions and methods therefor |
| US6447807B1 (en) | 1999-09-14 | 2002-09-10 | Dallas L. Clouatre | Potassium (-)-hydroxycitric acid methods for pharmaceutical preparations for stable and controlled delivery |
| US6207714B1 (en) | 1999-09-14 | 2001-03-27 | Dallas L. Clouatre | Methods and pharmaceutical preparations for improving glucose metabolism with (−)-hydroxycitric acid |
| US7015250B2 (en) | 2000-02-09 | 2006-03-21 | Glykon Technologies Group, Llc | Methods and pharmaceutical preparations for normalizing blood pressure with (-)-hydroxycitric acid |
| US6476071B1 (en) | 2001-05-07 | 2002-11-05 | Dallas L. Clouatre | Correcting polymorphic metabolic dysfunction with (−)-hydroxycitric acid |
| US6441041B1 (en) | 2001-06-20 | 2002-08-27 | Dallas L. Clouatre | (-)-hydroxycitric acid for the prevention of osteoporosis |
| US6482858B1 (en) | 2001-06-20 | 2002-11-19 | Dallas L Clouatre | (−)-hydroxycitric acid for wound healing and immunomodulation |
| US8394856B2 (en) | 2002-07-02 | 2013-03-12 | Glykon Technologies Group, Llc | (-)-Hydroxycitric acid for controlling inflammation |
| US7189416B2 (en) | 2002-11-23 | 2007-03-13 | Glykon Technologies Group, Llc | Method for stable and controlled delivery of (-)-hydroxycitric acid |
| US20040219124A1 (en) * | 2003-05-01 | 2004-11-04 | Gupta Shyam K. | Cosmetic and Pharmaceutical Masks Based on Ion-Pair Delivery System |
| AU2003241151A1 (en) * | 2003-05-19 | 2004-12-03 | Indfrag Limited | A novel composition of complex metal salt of garcinia acid, a process for preparing the same and use thereof |
| JP2007502331A (ja) | 2003-05-29 | 2007-02-08 | グリュコン テクノロジーズ グループ エルエルシー | （−）−ヒドロキシクエン酸を安定して制御送達するための方法および組成物 |
| US20050009919A1 (en) | 2003-07-07 | 2005-01-13 | Clouatre Dallas L. | Treating cachexia and excessive catabolism with (-)-hydroxycitric acid |
| US20060025483A1 (en) * | 2004-07-29 | 2006-02-02 | Clouatre Dallas L | (-)-Hydroxycitric acid for protection against soft tissue and arterial calcification |
| US20060074108A1 (en) | 2004-10-04 | 2006-04-06 | Bioderm Research | Matrix metalloprotease (MMP) inhibitors and their application in cosmetic and pharmaceutical composition |
| WO2008048574A2 (fr) | 2006-10-18 | 2008-04-24 | Dallas Clouatre | Hca pour assurer un meilleur profil sérique de lipides hdl |
| EP2125691A4 (fr) * | 2007-02-16 | 2012-02-01 | Vittal Mallya Scient Res Foundation | Dérivés de sel de métal de l'acide (-) hydroxycitrique de grande pureté et leur procédé de préparation |
| WO2008140444A1 (fr) | 2007-05-09 | 2008-11-20 | Clouatre Dallas L | Sels dimères solubles bimétalliques de l'acide hydroxycitrique, et leurs méthodes d'élaboration et d'utilisation |
| WO2010128949A1 (fr) | 2009-05-08 | 2010-11-11 | Asian Phytoceuticals Public Company Limited | Composition nutraceutique |
| US20100323031A1 (en) * | 2009-06-22 | 2010-12-23 | Glykon Technologies Group, Llc | Synergistic combination to enhance blood glucose and insulin metabolism |
| UA108077C2 (xx) | 2009-07-02 | 2015-03-25 | Синтез динатрієвої солі n4-(2,2-диметил-4-$(дигідрофосфонокси)метил]-3-оксо-5-піридо$1,4]оксазин-6-іл)-5-фтор-n2-(3,4,5-триметоксифеніл)-2,4-піримідиндіаміну | |
| US20110105600A1 (en) | 2009-10-29 | 2011-05-05 | Glykon Technologies Group, Llc | Synergistic composition of (-)-hydroxycitric acid with monoterpene and a method to enhance satiety |
| JPWO2016067968A1 (ja) | 2014-10-29 | 2017-04-27 | 昭和電工株式会社 | ミトコンドリア機能改善剤 |
| US9789076B2 (en) * | 2014-11-18 | 2017-10-17 | Glykon Technologies Group, Llc | Bolus dose of hydroxycitric acid with glycerol |
| CN104844447B (zh) * | 2015-04-15 | 2017-01-18 | 义乌章舸生物工程有限公司 | 一种以藤黄果为原料制备高纯度羟基柠檬酸的方法 |
| CN105669428B (zh) * | 2016-03-07 | 2018-06-01 | 江苏国信协联能源有限公司 | 一种柠檬酸氢钙的生产方法 |
-
2017
- 2017-09-08 WO PCT/US2017/050759 patent/WO2018049216A1/fr unknown
- 2017-09-08 CN CN201780069223.5A patent/CN110087646A/zh active Pending
- 2017-09-08 EP EP17849647.7A patent/EP3509578B1/fr active Active
- 2017-09-08 US US15/699,706 patent/US20180065992A1/en not_active Abandoned
-
2020
- 2020-05-07 US US16/869,097 patent/US11066423B2/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6160172A (en) * | 1997-08-27 | 2000-12-12 | Vittal Mallya Scientific Research Foundation | Soluble double metal salt of group IA and IIA of (-) hydroxycitric acid, process of preparing the same and its use in beverages and other food products without effecting their flavor and properties |
| WO2000048983A1 (fr) * | 1999-02-18 | 2000-08-24 | Vittal Mallya Scientific Research Foundation | Sel double soluble de metaux des groupes ia et iia d'acide (-) hydroxycitrique |
| WO2005025544A1 (fr) * | 2003-09-11 | 2005-03-24 | Glykon Technologies Group, Llc | Administration enterique d'acide (-)-hydroxycitrique |
| WO2005030195A1 (fr) * | 2003-09-20 | 2005-04-07 | Glykon Technologies Group, Llc | Acide (-)-hydroxycitrique pour retarder la vidange gastrique |
| US20060025482A1 (en) * | 2004-07-29 | 2006-02-02 | Clouatre Dallas L | (-)-Hydroxycitric acid for the modulation of angiotensin-converting enzyme |
| US20080145408A1 (en) * | 2006-12-15 | 2008-06-19 | Alex Moffett | Dimeric Double Metal Salts of (-) Hydroxycitric Acid, Methods of Making and Uses of Same |
| US20110274654A1 (en) * | 2010-05-05 | 2011-11-10 | Bahadoor Adilah | Triazoles as inhibitors of fatty acid synthase |
| JP2014218442A (ja) * | 2013-05-01 | 2014-11-20 | 昭和電工株式会社 | ヒドロキシトリカルボン酸のベンジル化方法 |
| US20180110750A1 (en) * | 2016-10-25 | 2018-04-26 | Glykon Technologies Group, Llc | Hydroxycitric acid compounds and capsule liquid delivery |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023074894A1 (fr) * | 2021-11-01 | 2023-05-04 | 小林製薬株式会社 | Agent pour favoriser la régénération de cartilages |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2018049216A1 (fr) | 2018-03-15 |
| US20200331930A1 (en) | 2020-10-22 |
| EP3509578B1 (fr) | 2022-12-21 |
| EP3509578A4 (fr) | 2020-05-27 |
| EP3509578A1 (fr) | 2019-07-17 |
| US11066423B2 (en) | 2021-07-20 |
| CN110087646A (zh) | 2019-08-02 |
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