SE452004B - Acylderivat av karnitin och farmaceutisk komposition innehallande nemnda forening - Google Patents

Acylderivat av karnitin och farmaceutisk komposition innehallande nemnda forening

Info

Publication number: SE452004B
Authority: SE; Sweden
Prior art keywords: acid; carnitine; chloride; pharmaceutically acceptable; group
Prior art date: 1980-03-06

Application number

SE8101267A

Other languages

English (en)

Swedish (sv)

Other versions

SE8101267L (sv

Inventor

C Cavazza

Witt P De

M O Tinti

Original Assignee

Sigma Tau Ind Farmaceuti

Priority date (The priority date 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 date listed.)

1980-03-06

Filing date

1981-02-26

Publication date

1987-11-09

1981-02-26 Application filed by Sigma Tau Ind Farmaceuti filed Critical Sigma Tau Ind Farmaceuti

1981-09-07 Publication of SE8101267L publication Critical patent/SE8101267L/xx

1987-11-09 Publication of SE452004B publication Critical patent/SE452004B/sv

Links

239000008194 pharmaceutical composition Substances 0.000 title claims 2
PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title description 4
YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 10
-1 sulphate anion Chemical class 0.000 claims description 10
229960004203 carnitine Drugs 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims description 4
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims 6
QOGMZIQMZUXOKM-UHFFFAOYSA-N 2-(cyclopenten-1-yl)acetic acid Chemical compound OC(=O)CC1=CCCC1 QOGMZIQMZUXOKM-UHFFFAOYSA-N 0.000 claims 3
VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 claims 3
229910021653 sulphate ion Inorganic materials 0.000 claims 3
208000020446 Cardiac disease Diseases 0.000 claims 2
208000031226 Hyperlipidaemia Diseases 0.000 claims 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
150000004820 halides Chemical class 0.000 claims 2
208000019622 heart disease Diseases 0.000 claims 2
208000020346 hyperlipoproteinemia Diseases 0.000 claims 2
IBMRTYCHDPMBFN-UHFFFAOYSA-N monomethyl glutaric acid Chemical compound COC(=O)CCCC(O)=O IBMRTYCHDPMBFN-UHFFFAOYSA-N 0.000 claims 2
JDRMYOQETPMYQX-UHFFFAOYSA-N monomethyl succinate Chemical compound COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 claims 2
150000003839 salts Chemical class 0.000 claims 2
YGLOSNDZOKLBMA-UHFFFAOYSA-N 3-(carboxymethoxy)propanoic acid Chemical compound OC(=O)CCOCC(O)=O YGLOSNDZOKLBMA-UHFFFAOYSA-N 0.000 claims 1
MYMNBFURSYZQBR-UHFFFAOYSA-N 5-ethoxy-5-oxopentanoic acid Chemical compound CCOC(=O)CCCC(O)=O MYMNBFURSYZQBR-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 25
150000001875 compounds Chemical class 0.000 description 16
238000002360 preparation method Methods 0.000 description 13
238000003756 stirring Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
229960000678 carnitine chloride Drugs 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 6
230000000694 effects Effects 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000003480 eluent Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
210000004165 myocardium Anatomy 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
MEFKEPWMEQBLKI-AIRLBKTGSA-O S-adenosyl-L-methionine Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H]([NH3+])C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-O 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
230000002745 absorbent Effects 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 2
OZGUGVRKYBSDBN-UHFFFAOYSA-N 3-phenylmethoxypropanoic acid Chemical compound OC(=O)CCOCC1=CC=CC=C1 OZGUGVRKYBSDBN-UHFFFAOYSA-N 0.000 description 2
206010002660 Anoxia Diseases 0.000 description 2
241000976983 Anoxia Species 0.000 description 2
BNJBFDFJGWXTAX-UHFFFAOYSA-N COCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O Chemical compound COCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O BNJBFDFJGWXTAX-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000007953 anoxia Effects 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
235000011148 calcium chloride Nutrition 0.000 description 2
230000008602 contraction Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000004006 olive oil Substances 0.000 description 2
235000008390 olive oil Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
239000008213 purified water Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
150000003626 triacylglycerols Chemical class 0.000 description 2
239000008215 water for injection Substances 0.000 description 2
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
CHHASAIQKXOAOX-UHFFFAOYSA-N 1-(2,2-dimethylpropoxy)-2,2-dimethylpropane Chemical compound CC(C)(C)COCC(C)(C)C CHHASAIQKXOAOX-UHFFFAOYSA-N 0.000 description 1
DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 description 1
JATKHYVXNZXXFU-UHFFFAOYSA-N 3-carboxy-4-cyclohex-3-en-1-yl-3-hydroxy-4-(trimethylazaniumyl)butanoate Chemical compound C1(CC=CCC1)C(C(O)(CC([O-])=O)C(=O)O)[N+](C)(C)C JATKHYVXNZXXFU-UHFFFAOYSA-N 0.000 description 1
XJGNRXDOYOEFKR-UHFFFAOYSA-N 3-phenylmethoxypropanoyl chloride Chemical compound ClC(=O)CCOCC1=CC=CC=C1 XJGNRXDOYOEFKR-UHFFFAOYSA-N 0.000 description 1
QGEIMXDFBNXUTH-UHFFFAOYSA-N C(C)OCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O Chemical compound C(C)OCC(=O)C(O)(C[N+](C)(C)C)CC([O-])=O QGEIMXDFBNXUTH-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
102000004895 Lipoproteins Human genes 0.000 description 1
108090001030 Lipoproteins Proteins 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930003779 Vitamin B12 Natural products 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000006536 aerobic glycolysis Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000006538 anaerobic glycolysis Effects 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
230000003126 arrythmogenic effect Effects 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 description 1
CXWMHIRIXVNVQN-UHFFFAOYSA-N cyclohex-3-ene-1-carbonyl chloride Chemical compound ClC(=O)C1CCC=CC1 CXWMHIRIXVNVQN-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
SRXOJMOGPYFZKC-UHFFFAOYSA-N methyl 4-chloro-4-oxobutanoate Chemical compound COC(=O)CCC(Cl)=O SRXOJMOGPYFZKC-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
206010047302 ventricular tachycardia Diseases 0.000 description 1
239000011715 vitamin B12 Substances 0.000 description 1
235000019163 vitamin B12 Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Dispersion Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Dermatology (AREA)
Hematology (AREA)
Emergency Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Obesity (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SE8101267A 1980-03-06 1981-02-26 Acylderivat av karnitin och farmaceutisk komposition innehallande nemnda forening SE452004B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT48099/80A IT1145362B (it)	1980-03-06	1980-03-06	Classe di acil-derivati della carnitina procedimento per la loro preparazione e loro uso terapeutico

Publications (2)

Publication Number	Publication Date
SE8101267L SE8101267L (sv)	1981-09-07
SE452004B true SE452004B (sv)	1987-11-09

Family

ID=11264505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8101267A SE452004B (sv)	1980-03-06	1981-02-26	Acylderivat av karnitin och farmaceutisk komposition innehallande nemnda forening

Country Status (22)

Country	Link
US (2)	US4766222A (fr)
JP (1)	JPS56139442A (fr)
AR (1)	AR228591A1 (fr)
AT (1)	AT376200B (fr)
AU (1)	AU543799B2 (fr)
BE (1)	BE887695A (fr)
CA (1)	CA1178971A (fr)
CH (1)	CH653008A5 (fr)
DE (1)	DE3107743A1 (fr)
DK (1)	DK154424C (fr)
ES (1)	ES500131A0 (fr)
FI (1)	FI78680C (fr)
FR (1)	FR2477536B1 (fr)
GB (1)	GB2071091B (fr)
GR (1)	GR74440B (fr)
IE (1)	IE50959B1 (fr)
IL (1)	IL62189A (fr)
IT (1)	IT1145362B (fr)
LU (1)	LU83183A1 (fr)
MX (1)	MX155928A (fr)
NL (1)	NL8101067A (fr)
SE (1)	SE452004B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1145371B (it) *	1980-05-30	1986-11-05	Sigma Tau Ind Farmaceuti	Alcossi-acil carnitine procedimento per la loro preparazione e composizioni farmaceutiche che le contengono
IT1147079B (it) *	1980-05-30	1986-11-19	Sigma Tau Ind Farmacuetiche Ri	Esteri di alcossi-acil derivati della carnitina procedimento per la loro preparatione e composizioni farmaceutiche che li contengono
IT1238344B (it) *	1989-10-20	1993-07-13	Sigma Tau Ind Farmaceuti	Estere della l-carnitina con l'acido gamma-idrossibutirrico e composizioni farmaceutiche che lo contengono per l'inibizione della degenerazione neuronale e nel trattamento del coma
IT1240775B (it) *	1990-02-23	1993-12-17	Sigma Tau Ind Farmaceuti	Esteri della l-carnitina e di acil-l-carnitine con l'acido beta-idrossibutirrico e composizioni farmaceutiche che li contengono per la inibizione della degenerazione neuronale, della proteolisi epatica e nel trattamento del coma.
US6323237B1 (en) *	1997-03-17	2001-11-27	Btg International Limited	Therapeutic compositions
AU7828200A (en)	1999-09-23	2001-04-24	Juvenon Corporation	Nutritional supplement for increased energy and stamina
US6562869B1 (en)	1999-09-23	2003-05-13	Juvenon, Inc.	Nutritional supplement for increased energy and stamina
WO2001032168A1 (fr)	1999-11-03	2001-05-10	Juvenon, Inc.	Traitement de la perte de memoire benigne
JP4954864B2 (ja) *	2004-04-01	2012-06-20	カーディオムファーマコーポレイション	イオンチャネル調節化合物のプロドラッグおよびその使用
JP6296433B2 (ja) *	2012-11-22	2018-03-20	国立大学法人山形大学	生体適合性ポリマー及びその製造方法並びにそれを製造するための新規化合物
CN110997624B (zh) *	2017-06-06	2024-05-24	韦恩州立大学	与肉毒碱衍生的材料相关的方法和组合物

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1108125A (fr) *	1953-05-08	1956-01-09	Laboratoires Labaz Soc D	Procédé de préparation d'un dérivé stable de la carnitine
US3624887A (en) *	1970-03-02	1971-12-07	Bunker Ramo	Pin and socket removal tool
AU518617B2 (en) *	1977-04-29	1981-10-08	Sigma-Tau Industrie Farmaceutiche Riunite S.P.A.	Therapeutic application of acetyl-d, 1-carnitine
JPS5481963A (en) *	1977-12-13	1979-06-29	Ihachi Nosaka	Roll paper holder for lavatory
DE2903579A1 (de) *	1978-02-03	1979-08-09	Sigma Tau Ind Farmaceuti	Verwendung von acetylcarnitin und anderen acylderivaten des carnitins zur behandlung der hyperlipoproteinaemie und hyperlimpidaemie sowie arzneimittel
IT1156741B (it) *	1978-05-15	1987-02-04	Sigma Tau Ind Farmaceuti	Applicazione terapeutica della carnitina e di alcuni derivati acilati della carnitina nell'emodialisi
IT1156769B (it) *	1978-05-25	1987-02-04	Sigma Tau Ind Farmaceuti	Applicazione terapeutica della carnitina e di altri acil derivati della carnitina
IT1156840B (it) *	1978-06-27	1987-02-04	Sigma Tau Ind Farmaceuti	Acil derivati della carnitina
JPS5554821A (en) *	1978-10-18	1980-04-22	Iseki Agricult Mach	Discharging dust adjuster of thresher
US4518776A (en) *	1982-07-19	1985-05-21	Ciba Geigy Corporation	Process for producing sulfonylureas
DE3427847A1 (de) *	1983-12-09	1985-06-13	Bayer Ag, 5090 Leverkusen	Thiolan-2,4-dion-3-carboxamide
US4707491A (en) *	1985-12-20	1987-11-17	Washington University	Anticonvulsant γ-thiobutyrolactone derivatives

1980
- 1980-03-06 IT IT48099/80A patent/IT1145362B/it active
1981
- 1981-02-23 IL IL62189A patent/IL62189A/xx not_active IP Right Cessation
- 1981-02-23 IE IE359/81A patent/IE50959B1/en not_active IP Right Cessation
- 1981-02-26 SE SE8101267A patent/SE452004B/sv not_active IP Right Cessation
- 1981-02-26 BE BE0/203935A patent/BE887695A/fr not_active IP Right Cessation
- 1981-02-28 DE DE19813107743 patent/DE3107743A1/de not_active Ceased
- 1981-03-03 LU LU83183A patent/LU83183A1/fr unknown
- 1981-03-03 AU AU68028/81A patent/AU543799B2/en not_active Expired
- 1981-03-04 GR GR64312A patent/GR74440B/el unknown
- 1981-03-04 FR FR8104331A patent/FR2477536B1/fr not_active Expired
- 1981-03-04 GB GB8106836A patent/GB2071091B/en not_active Expired
- 1981-03-05 ES ES500131A patent/ES500131A0/es active Granted
- 1981-03-05 CH CH1485/81A patent/CH653008A5/it not_active IP Right Cessation
- 1981-03-05 DK DK100181A patent/DK154424C/da not_active IP Right Cessation
- 1981-03-05 MX MX186251A patent/MX155928A/es unknown
- 1981-03-05 CA CA000372368A patent/CA1178971A/fr not_active Expired
- 1981-03-05 FI FI810695A patent/FI78680C/fi not_active IP Right Cessation
- 1981-03-05 NL NL8101067A patent/NL8101067A/nl not_active Application Discontinuation
- 1981-03-06 AT AT0103981A patent/AT376200B/de not_active IP Right Cessation
- 1981-03-06 AR AR284535A patent/AR228591A1/es active
- 1981-03-06 JP JP3305481A patent/JPS56139442A/ja active Pending
1987
- 1987-06-30 US US07/068,748 patent/US4766222A/en not_active Expired - Lifetime
1988
- 1988-05-31 US US07/200,641 patent/US4859698A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
US4859698A (en)	1989-08-22
IT8048099A0 (it)	1980-03-06
JPS56139442A (en)	1981-10-30
AU6802881A (en)	1981-09-24
ES8201535A1 (es)	1982-01-01
IL62189A (en)	1985-10-31
DK100181A (da)	1981-09-07
NL8101067A (nl)	1981-10-01
FI78680B (fi)	1989-05-31
GR74440B (fr)	1984-06-28
FI78680C (fi)	1989-09-11
LU83183A1 (fr)	1981-06-24
ATA103981A (de)	1984-03-15
DK154424C (da)	1989-05-22
IE810359L (en)	1981-09-06
AR228591A1 (es)	1983-03-30
DE3107743A1 (de)	1981-12-03
AT376200B (de)	1984-10-25
AU543799B2 (en)	1985-05-02
IL62189A0 (en)	1981-03-31
DK154424B (da)	1988-11-14
MX155928A (es)	1988-05-24
CH653008A5 (it)	1985-12-13
FR2477536A1 (fr)	1981-09-11
CA1178971A (fr)	1984-12-04
SE8101267L (sv)	1981-09-07
FI810695L (fi)	1981-09-07
GB2071091A (en)	1981-09-16
GB2071091B (en)	1984-09-12
BE887695A (fr)	1981-06-15
FR2477536B1 (fr)	1986-04-04
US4766222A (en)	1988-08-23
IE50959B1 (en)	1986-08-20
ES500131A0 (es)	1982-01-01
IT1145362B (it)	1986-11-05

Publication	Publication Date	Title
SE447244B (sv)	1986-11-03	Acylkarnitinamider, sett att framstella desamma samt farmaceutiska kompositioner innehallande desamma
SE452004B (sv)	1987-11-09	Acylderivat av karnitin och farmaceutisk komposition innehallande nemnda forening
JPH0211579B2 (fr)	1990-03-14
US3987049A (en)	1976-10-19	Esters of dihydroapovincaminic acid
US3394181A (en)	1968-07-23	Phenoxy-lower-alkyl-amidoximes and phenylamino-lower-alkyl-amidoximes
EP0063084B1 (fr)	1984-09-12	Dérivés de phénéthanolamine, leur préparation et leur application en thérapeutique
EP0096279B1 (fr)	1985-11-06	N-(2-méthoxyéthyl)-noroxymorphone, ses sels acides d'addition, des médicaments la contenant et un procédé pour sa préparation
SE452005B (sv)	1987-11-09	Estrar av alkoxi-acylderivat av karnitin och farmaceutiska kompositioner innehallande desamma
SE450704B (sv)	1987-07-20	3,7-diazabicyklo /3,3,1/ nonaner, forfarande for framstellning och farmaceutisk beredning derav
US3637759A (en)	1972-01-25	Chromanes
JPS6225149B2 (fr)	1987-06-01
EP0187509A2 (fr)	1986-07-16	9-Aminoalkylfluorènes
US3428653A (en)	1969-02-18	3-indolylmethylguanidine
US4590209A (en)	1986-05-20	Alkoxy-acyl carnitines and pharmaceutical compositions containing same
Vidal	1959	Reaction of ethylene dibromide with triethylamine and the restoring action of some alkanebis (triethylammonium) ions upon sodium-deficient nerve fibers
US3912722A (en)	1975-10-14	Novel 6{62 -amino-steroids and production thereof
FI69464B (fi)	1985-10-31	Foerfarande foer framstaellning av farmakologiskt verksamma 10bromsandvicin och 10-bromisosandvicin
US3971798A (en)	1976-07-27	Pyridine derivative, processes of preparation and pharmaceutical compositions
US3646067A (en)	1972-02-29	Adamantylaminophenoxypropanols and ester derivatives
CH646170A5 (de)	1984-11-15	Pyrazolo(1,5-c)chinazolinderivate und diese enthaltende arzneimittel.
FI58119C (fi)	1980-12-10	Foerfarande foer framstaellning av dibensylglykolsyraderivat med terapeutisk verkan
KR850000569B1 (ko)	1985-04-29	카르니틴의 아실-유도체 제조방법
PL144546B1 (en)	1988-06-30	Method of obtaining novel derivatives of azabicyclo /3.3.1/nonane
US4670435A (en)	1987-06-02	10,11-dihydro-5H-dibenzo[a,d]cycloheptadiene derivatives in a method for treating cardiac arrhythmia
AT367015B (de)	1982-05-25	Verfahren zur herstellung von neuen substituierten phenylessigsaeuren, deren niederen alkylestern undsalzen

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