JPS58201746A - ３−ヒドロキシブタン酸またはこの酸から誘導された塩を含有する薬剤組成物、および３−ヒドロキシブタン酸から誘導され、医薬として使用できる化合物 - Google Patents
３−ヒドロキシブタン酸またはこの酸から誘導された塩を含有する薬剤組成物、および３−ヒドロキシブタン酸から誘導され、医薬として使用できる化合物Info
- Publication number
- JPS58201746A JPS58201746A JP58029197A JP2919783A JPS58201746A JP S58201746 A JPS58201746 A JP S58201746A JP 58029197 A JP58029197 A JP 58029197A JP 2919783 A JP2919783 A JP 2919783A JP S58201746 A JPS58201746 A JP S58201746A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound according
- hydroxybutanoic acid
- derived
- hydroxybutanoic
- 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.)
- Pending
Links
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 150000003839 salts Chemical class 0.000 title claims abstract description 36
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 title claims description 21
- 239000003814 drug Substances 0.000 title claims description 7
- 229940079593 drug Drugs 0.000 title description 3
- 150000001413 amino acids Chemical class 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 125000001477 organic nitrogen group Chemical group 0.000 claims abstract description 5
- 235000001014 amino acid Nutrition 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 210000004165 myocardium Anatomy 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
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- 238000004519 manufacturing process Methods 0.000 claims description 4
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- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- 230000017531 blood circulation Effects 0.000 claims description 3
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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 2
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- 229940126534 drug product Drugs 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 abstract description 10
- 230000000302 ischemic effect Effects 0.000 abstract description 6
- 239000004475 Arginine Substances 0.000 abstract description 5
- 208000031229 Cardiomyopathies Diseases 0.000 abstract description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 abstract description 3
- 238000009109 curative therapy Methods 0.000 abstract 1
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- 238000012360 testing method Methods 0.000 description 34
- 229940024606 amino acid Drugs 0.000 description 9
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
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- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 2
- 229930064664 L-arginine Natural products 0.000 description 2
- 235000014852 L-arginine Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
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- 239000003708 ampul Substances 0.000 description 2
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- 235000009697 arginine Nutrition 0.000 description 2
- 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 2
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- 229910052751 metal Chemical class 0.000 description 2
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 239000003826 tablet Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical compound CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000010444 Acidosis Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 206010027417 Metabolic acidosis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
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- 239000006172 buffering agent Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 239000003862 glucocorticoid Substances 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
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- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
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- 229960005181 morphine Drugs 0.000 description 1
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- 229920005615 natural polymer Polymers 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic 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
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- 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
-
- 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
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8203100A FR2521857B1 (fr) | 1982-02-23 | 1982-02-23 | Compositions pharmaceutiques contenant de l'acide 3-hydroxybutanoique ou un sel derive de cet acide et sels derives de l'acide 3-hydroxybutanoique et d'une base organique azotee |
| FR8203100 | 1982-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58201746A true JPS58201746A (ja) | 1983-11-24 |
Family
ID=9271331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58029197A Pending JPS58201746A (ja) | 1982-02-23 | 1983-02-23 | ３−ヒドロキシブタン酸またはこの酸から誘導された塩を含有する薬剤組成物、および３−ヒドロキシブタン酸から誘導され、医薬として使用できる化合物 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4579955A (enExample) |
| EP (1) | EP0087192B1 (enExample) |
| JP (1) | JPS58201746A (enExample) |
| KR (1) | KR910000143B1 (enExample) |
| AT (1) | ATE24478T1 (enExample) |
| AU (2) | AU560757B2 (enExample) |
| CA (1) | CA1203242A (enExample) |
| DE (1) | DE3368601D1 (enExample) |
| DK (1) | DK163235C (enExample) |
| ES (2) | ES8500240A1 (enExample) |
| FI (1) | FI79523C (enExample) |
| FR (1) | FR2521857B1 (enExample) |
| GR (1) | GR77934B (enExample) |
| IE (1) | IE54561B1 (enExample) |
| IL (1) | IL67965A0 (enExample) |
| MX (1) | MX156855A (enExample) |
| NO (1) | NO161909C (enExample) |
| NZ (1) | NZ203279A (enExample) |
| PH (1) | PH21561A (enExample) |
| PT (1) | PT76267A (enExample) |
| ZA (1) | ZA831019B (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0780123A1 (en) | 1995-12-01 | 1997-06-25 | Shimizu Pharmaceutical Co., Ltd. | Beta-hydroxybutyric acid or acetoacetic acid or salts or esters therof for use in improving cerebral function |
| JP2001515510A (ja) * | 1997-03-17 | 2001-09-18 | ビーティージー・インターナショナル・リミテッド | 治療用組成物 |
| WO2008053982A1 (en) | 2006-10-30 | 2008-05-08 | Ophtecs Corporation | Composition for treating allergy |
| JP2017201906A (ja) * | 2016-05-10 | 2017-11-16 | 大阪瓦斯株式会社 | 栄養剤組成物及び栄養補助食品 |
| WO2017222043A1 (ja) * | 2016-06-24 | 2017-12-28 | 協和発酵バイオ株式会社 | ３－ヒドロキシイソ吉草酸アミノ酸塩の結晶及びその製造方法 |
| US10647653B2 (en) | 2015-11-19 | 2020-05-12 | Kyowa Hakko Bio Co., Ltd. | Crystal of monovalent cation salt of 3-hydroxyisovaleric acid and process for producing the crystal |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2521857B1 (fr) * | 1982-02-23 | 1985-10-31 | Solvay | Compositions pharmaceutiques contenant de l'acide 3-hydroxybutanoique ou un sel derive de cet acide et sels derives de l'acide 3-hydroxybutanoique et d'une base organique azotee |
| US6020007A (en) * | 1984-06-22 | 2000-02-01 | Btg International Limited | Fluid therapy with l-lactate and/or pyruvate anions |
| USRE38604E1 (en) | 1984-06-22 | 2004-09-28 | Btg International Limited | Fluid therapy with L-lactate and/or pyruvate anions |
| US4777288A (en) * | 1987-06-11 | 1988-10-11 | Pfizer Inc. | Process for preparing a 4,4-diphenylbutanoic acid derivative |
| BE1001209A3 (fr) * | 1987-11-19 | 1989-08-22 | Solvay | Compositions pharmaceutiques contenant un derive de l'acide 3-hydroxybutanoique choisi parmi les oligomeres de cet acide et les esters de cet acide ou de ces oligomeres avec du 1,3-butanediol. |
| US5292774A (en) * | 1988-07-26 | 1994-03-08 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Substitution fluid preparation comprising 3-hydroxy-butyric acid (β-hydroxybutric acid) and its salts |
| DE4113984C2 (de) * | 1991-04-29 | 2002-05-08 | Koehler Chemie Dr Franz | Salze der 4-Hydroxy-Buttersäure |
| ES2051222B1 (es) * | 1992-03-12 | 1995-02-16 | Sanmiguel Gabriel Serrano | Procedimiento de neutralizacion de acido alfa-hidroxietanoico. |
| US6316038B1 (en) | 1997-03-17 | 2001-11-13 | Btg International Limited | Therapeutic compositions |
| US6323237B1 (en) * | 1997-03-17 | 2001-11-27 | Btg International Limited | Therapeutic compositions |
| US20090253781A1 (en) * | 2002-05-24 | 2009-10-08 | Btg International Limited | Therapeutic compositions |
| US6613356B1 (en) | 2000-10-10 | 2003-09-02 | Victor Vlahakos | Weight loss medication and method |
| GB0420856D0 (en) * | 2004-09-20 | 2004-10-20 | Ketocytonyx Inc | Cns modulators |
| WO2006020137A2 (en) * | 2004-07-16 | 2006-02-23 | Ketocytonyx Inc. | Oligomeric compounds |
| WO2006020179A2 (en) * | 2004-07-20 | 2006-02-23 | Ketocytonyx Inc. | Oligomeric ketone compounds |
| EP1778212A4 (en) * | 2004-07-23 | 2010-12-08 | Btg Int Ltd | SACCHARIDES CETOGENES |
| US20070197645A1 (en) * | 2004-09-21 | 2007-08-23 | Martin Keith F | Treatment of adhd |
| ES2574557T3 (es) * | 2004-09-21 | 2016-06-20 | Btg International Limited | Miméticos dopaminérgicos |
| RU2302239C1 (ru) * | 2006-07-14 | 2007-07-10 | Михаил Владимирович Покровский | Способ фармакологической коррекции ишемии конечности |
| DK2914251T3 (da) | 2012-11-05 | 2019-11-04 | Us Health | Ketonlegemer til beskyttelse af væv mod beskadigelse som følge af ioniseringsstråling |
| US11241403B2 (en) | 2016-03-11 | 2022-02-08 | Axcess Global Sciences, Llc | Beta-hydroxybutyrate mixed salt compositions and methods of use |
| US11103470B2 (en) | 2017-11-22 | 2021-08-31 | Axcess Global Sciences, Llc | Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use |
| US12109182B2 (en) | 2016-04-19 | 2024-10-08 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate and related compounds in humans |
| US10925843B2 (en) | 2018-04-18 | 2021-02-23 | Axcess Global Sciences, Llc | Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate |
| US11806324B2 (en) | 2018-04-18 | 2023-11-07 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
| US11202769B2 (en) | 2017-11-22 | 2021-12-21 | Axcess Global Sciences, Llc | Ketone body esters of s-beta-hydroxybutyrate and/or s-1,3-butanediol for modifying metabolic function |
| US12090129B2 (en) | 2017-11-22 | 2024-09-17 | Axcess Global Sciences, Llc | Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use |
| US11944598B2 (en) | 2017-12-19 | 2024-04-02 | Axcess Global Sciences, Llc | Compositions containing s-beta-hydroxybutyrate or non-racemic mixtures enriched with the s-enatiomer |
| US12329734B2 (en) | 2017-12-19 | 2025-06-17 | Axcess Global Sciences, Llc | Use of S-beta-hydroxybutyrate compounds for induction and maintenance of flow |
| US12472200B2 (en) | 2019-05-15 | 2025-11-18 | Axcess Global Sciences, Llc | Autobiotic compositions and method for promoting healthy gut microbiome |
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| US12167993B2 (en) | 2019-06-21 | 2024-12-17 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| US11950616B2 (en) | 2019-06-21 | 2024-04-09 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| CN112341331B (zh) * | 2019-08-07 | 2023-04-07 | 辽宁科硕营养科技股份有限公司 | 一种3-羟基丁酸盐及其制备方法与应用 |
| US12186297B2 (en) | 2020-08-26 | 2025-01-07 | Axcess Global Sciences, Llc | Compositions and methods for increasing lean-to-fat mass ratio |
| WO2024192165A1 (en) * | 2023-03-14 | 2024-09-19 | The Board Of Trustees Of The Leland Stanford Junior University | N-beta-hydroxybutyryl-amino acids and related compositions and methods |
| WO2025056246A1 (en) * | 2023-09-11 | 2025-03-20 | Societe Des Produits Nestle S.A. | Polymorphs and compositions comprising same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2101097A (en) * | 1934-07-26 | 1937-12-07 | Wm S Merrell Co | Products for rendering the urine bacteriostatic |
| US2799684A (en) * | 1954-06-18 | 1957-07-16 | Food Chemical And Res Lab Inc | Crystalline compounds of tryptophane and methods of manufacturing them |
| NL279760A (enExample) * | 1961-06-17 | |||
| US3830931A (en) * | 1972-11-06 | 1974-08-20 | Felice S De | Carnitine and its use in the treatment of arrhythmia and impaired cardiac function |
| US3879537A (en) * | 1973-09-04 | 1975-04-22 | Scott Eugene J Van | Treatment of ichthyosiform dermatoses |
| DE2733202A1 (de) * | 1976-08-04 | 1978-02-09 | Agroferm Ag | Verfahren zur herstellung der d(-)-3-hydroxybuttersaeure |
| US4412943A (en) * | 1981-02-23 | 1983-11-01 | Kao Soap Co., Ltd. | Liquid detergent composition |
| FR2521857B1 (fr) * | 1982-02-23 | 1985-10-31 | Solvay | Compositions pharmaceutiques contenant de l'acide 3-hydroxybutanoique ou un sel derive de cet acide et sels derives de l'acide 3-hydroxybutanoique et d'une base organique azotee |
-
1982
- 1982-02-23 FR FR8203100A patent/FR2521857B1/fr not_active Expired
-
1983
- 1983-02-15 DE DE8383200228T patent/DE3368601D1/de not_active Expired
- 1983-02-15 EP EP83200228A patent/EP0087192B1/fr not_active Expired
- 1983-02-15 NZ NZ203279A patent/NZ203279A/en unknown
- 1983-02-15 ZA ZA831019A patent/ZA831019B/xx unknown
- 1983-02-15 AT AT83200228T patent/ATE24478T1/de active
- 1983-02-17 AU AU11624/83A patent/AU560757B2/en not_active Ceased
- 1983-02-21 PH PH28545A patent/PH21561A/en unknown
- 1983-02-21 PT PT76267A patent/PT76267A/pt not_active IP Right Cessation
- 1983-02-21 GR GR70556A patent/GR77934B/el unknown
- 1983-02-21 IL IL67965A patent/IL67965A0/xx not_active IP Right Cessation
- 1983-02-22 ES ES519991A patent/ES8500240A1/es not_active Expired
- 1983-02-22 NO NO830618A patent/NO161909C/no unknown
- 1983-02-22 US US06/468,385 patent/US4579955A/en not_active Expired - Fee Related
- 1983-02-22 IE IE366/83A patent/IE54561B1/en not_active IP Right Cessation
- 1983-02-22 MX MX196357A patent/MX156855A/es unknown
- 1983-02-23 KR KR1019830000728A patent/KR910000143B1/ko not_active Expired
- 1983-02-23 JP JP58029197A patent/JPS58201746A/ja active Pending
- 1983-02-23 FI FI830603A patent/FI79523C/fi not_active IP Right Cessation
- 1983-02-23 CA CA000422215A patent/CA1203242A/fr not_active Expired
- 1983-02-23 DK DK081583A patent/DK163235C/da not_active IP Right Cessation
-
1984
- 1984-05-28 ES ES532880A patent/ES532880A0/es active Granted
-
1985
- 1985-10-23 US US06/790,391 patent/US4771074A/en not_active Expired - Fee Related
-
1987
- 1987-02-23 AU AU69161/87A patent/AU602329B2/en not_active Ceased
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0780123A1 (en) | 1995-12-01 | 1997-06-25 | Shimizu Pharmaceutical Co., Ltd. | Beta-hydroxybutyric acid or acetoacetic acid or salts or esters therof for use in improving cerebral function |
| US6136862A (en) * | 1995-12-01 | 2000-10-24 | Shimizu Pharmaceutical Co., Ltd. | Cerebral function improving agents |
| US6232345B1 (en) | 1995-12-01 | 2001-05-15 | Shimizu Pharmaceutical Co., Ltd. | Cerebral function improving agents |
| JP2001515510A (ja) * | 1997-03-17 | 2001-09-18 | ビーティージー・インターナショナル・リミテッド | 治療用組成物 |
| JP2015042644A (ja) * | 1997-03-17 | 2015-03-05 | ビーティージー・インターナショナル・リミテッド | 治療用組成物 |
| WO2008053982A1 (en) | 2006-10-30 | 2008-05-08 | Ophtecs Corporation | Composition for treating allergy |
| US10647653B2 (en) | 2015-11-19 | 2020-05-12 | Kyowa Hakko Bio Co., Ltd. | Crystal of monovalent cation salt of 3-hydroxyisovaleric acid and process for producing the crystal |
| JP2017201906A (ja) * | 2016-05-10 | 2017-11-16 | 大阪瓦斯株式会社 | 栄養剤組成物及び栄養補助食品 |
| WO2017222043A1 (ja) * | 2016-06-24 | 2017-12-28 | 協和発酵バイオ株式会社 | ３－ヒドロキシイソ吉草酸アミノ酸塩の結晶及びその製造方法 |
| JPWO2017222043A1 (ja) * | 2016-06-24 | 2019-06-20 | 協和発酵バイオ株式会社 | ３−ヒドロキシイソ吉草酸アミノ酸塩の結晶及びその製造方法 |
| US11098007B2 (en) | 2016-06-24 | 2021-08-24 | Kyowa Hakko Bio Co., Ltd. | Crystal of amino acid salt of 3-hydroxyisovaleric acid and production method thereof |
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