IE54561B1 - Pharmaceutical compositions containing 3-hydroxybutanois acid or a salt derived from this acid, and compounds derived from 3-hydroxybutanoic acid which can be used as medicaments - Google Patents
Pharmaceutical compositions containing 3-hydroxybutanois acid or a salt derived from this acid, and compounds derived from 3-hydroxybutanoic acid which can be used as medicamentsInfo
- Publication number
- IE54561B1 IE54561B1 IE366/83A IE36683A IE54561B1 IE 54561 B1 IE54561 B1 IE 54561B1 IE 366/83 A IE366/83 A IE 366/83A IE 36683 A IE36683 A IE 36683A IE 54561 B1 IE54561 B1 IE 54561B1
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- hydroxybutanoic acid
- amino acid
- derived
- hydroxybutanoic
- Prior art date
Links
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 150000003839 salts Chemical class 0.000 title claims abstract description 38
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 title claims description 22
- 239000003814 drug Substances 0.000 title claims description 5
- 239000002253 acid Substances 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 150000001413 amino acids Chemical class 0.000 claims abstract description 23
- 125000001477 organic nitrogen group Chemical group 0.000 claims abstract description 8
- 235000001014 amino acid Nutrition 0.000 claims description 22
- 229940024606 amino acid Drugs 0.000 claims description 22
- 210000004165 myocardium Anatomy 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 7
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 6
- 230000002503 metabolic effect Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 229930064664 L-arginine Natural products 0.000 claims description 3
- 235000014852 L-arginine Nutrition 0.000 claims description 3
- 230000017531 blood circulation Effects 0.000 claims description 3
- 230000004060 metabolic process Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 210000004903 cardiac system Anatomy 0.000 claims description 2
- 229960002885 histidine Drugs 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 229940127557 pharmaceutical product Drugs 0.000 claims 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 2
- 150000001457 metallic cations Chemical class 0.000 claims 2
- 235000019766 L-Lysine Nutrition 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 abstract description 10
- 230000000302 ischemic effect Effects 0.000 abstract description 6
- 208000031229 Cardiomyopathies Diseases 0.000 abstract description 4
- 239000004475 Arginine Substances 0.000 abstract description 3
- 150000001412 amines Chemical class 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 description 2
- 230000000069 prophylactic effect Effects 0.000 abstract description 2
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- 238000002474 experimental method Methods 0.000 description 44
- 230000000638 stimulation Effects 0.000 description 12
- 230000036284 oxygen consumption Effects 0.000 description 11
- 230000001800 adrenalinergic effect Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 230000002107 myocardial effect Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000001990 intravenous administration Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001483 arginine derivatives Chemical class 0.000 description 7
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- 235000021588 free fatty acids Nutrition 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 230000010412 perfusion Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000010255 intramuscular injection Methods 0.000 description 3
- 239000007927 intramuscular injection Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000002059 L-arginyl group Chemical class O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 244000246386 Mentha pulegium Species 0.000 description 2
- 235000016257 Mentha pulegium Nutrition 0.000 description 2
- 235000004357 Mentha x piperita Nutrition 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- -1 ampoules Substances 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 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
- 230000037396 body weight Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012154 double-distilled water Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000001050 hortel pimenta Nutrition 0.000 description 2
- 229910052751 metal Chemical class 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- 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
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 229940081974 saccharin Drugs 0.000 description 2
- 235000019204 saccharin Nutrition 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010027417 Metabolic acidosis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 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
- SPYUULCOLNMBGS-UHFFFAOYSA-L [Mg+2].O[Si](O)(O)O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound [Mg+2].O[Si](O)(O)O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SPYUULCOLNMBGS-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 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
- 238000001949 anaesthesia Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 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
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000000872 buffer 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
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000005796 circulatory shock Effects 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 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
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229940105631 nembutal Drugs 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
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 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
- 239000008024 pharmaceutical diluent Substances 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
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 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
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000002966 serum Anatomy 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
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection 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
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 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
- 230000001960 triggered effect Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000005303 weighing Methods 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 (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE830366L IE830366L (en) | 1983-08-23 |
| IE54561B1 true IE54561B1 (en) | 1989-11-22 |
Family
ID=9271331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE366/83A IE54561B1 (en) | 1982-02-23 | 1983-02-22 | Pharmaceutical compositions containing 3-hydroxybutanois acid or a salt derived from this acid, and compounds derived from 3-hydroxybutanoic acid which can be used as medicaments |
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) |
Families Citing this family (43)
| 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. |
| JP4598203B2 (ja) | 1995-12-01 | 2010-12-15 | ビーティージー・インターナショナル・リミテッド | 脳機能改善剤 |
| US6316038B1 (en) | 1997-03-17 | 2001-11-13 | Btg International Limited | Therapeutic compositions |
| CA2283642C (en) * | 1997-03-17 | 2012-05-15 | 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 |
| JPWO2008053982A1 (ja) | 2006-10-30 | 2010-02-25 | 株式会社オフテクス | アレルギー治療用組成物 |
| DK2914251T3 (da) | 2012-11-05 | 2019-11-04 | Us Health | Ketonlegemer til beskyttelse af væv mod beskadigelse som følge af ioniseringsstråling |
| KR20180088809A (ko) | 2015-11-19 | 2018-08-07 | 가부시키가이샤 오츠카 세이야쿠 코죠 | 3-히드록시이소발레르산의 1가 양이온염의 결정 및 그 결정의 제조 방법 |
| 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 |
| JP6710098B2 (ja) * | 2016-05-10 | 2020-06-17 | 大阪瓦斯株式会社 | 栄養剤組成物及び栄養補助食品 |
| 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 |
| 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 |
| US11969430B1 (en) | 2023-03-10 | 2024-04-30 | Axcess Global Sciences, Llc | Compositions containing paraxanthine and beta-hydroxybutyrate or precursor for increasing neurological and physiological performance |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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
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Legal Events
| Date | Code | Title | Description |
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| MM4A | Patent lapsed |