US20050080018A1 - Use of alkanoyl l-carnitine for the treatment of erectile dysfunction - Google Patents
Use of alkanoyl l-carnitine for the treatment of erectile dysfunction Download PDFInfo
- Publication number
- US20050080018A1 US20050080018A1 US10/497,498 US49749804A US2005080018A1 US 20050080018 A1 US20050080018 A1 US 20050080018A1 US 49749804 A US49749804 A US 49749804A US 2005080018 A1 US2005080018 A1 US 2005080018A1
- Authority
- US
- United States
- Prior art keywords
- treatment
- erectile dysfunction
- acid
- carnitine
- alkanoyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 alkanoyl l-carnitine Chemical compound 0.000 title claims abstract description 34
- 208000010228 Erectile Dysfunction Diseases 0.000 title claims abstract description 27
- 201000001881 impotence Diseases 0.000 title claims abstract description 27
- 229960001518 levocarnitine Drugs 0.000 title 1
- 239000003814 drug Substances 0.000 claims abstract description 35
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 claims description 24
- 229940079593 drug Drugs 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- 229960003310 sildenafil Drugs 0.000 claims description 12
- 206010012601 diabetes mellitus Diseases 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- UFAHZIUFPNSHSL-MRVPVSSYSA-N O-propanoyl-L-carnitine Chemical compound CCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C UFAHZIUFPNSHSL-MRVPVSSYSA-N 0.000 claims description 8
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- 229930008281 A03AD01 - Papaverine Natural products 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 229960001789 papaverine Drugs 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- WGAOZGUUHIBABN-UHFFFAOYSA-N 1-aminopentan-1-ol Chemical compound CCCCC(N)O WGAOZGUUHIBABN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- NDVRKEKNSBMTAX-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;phosphoric acid Chemical compound OP(O)(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O NDVRKEKNSBMTAX-BTVCFUMJSA-N 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- QWJSAWXRUVVRLH-LREBCSMRSA-M 2-hydroxyethyl(trimethyl)azanium;(2r,3r)-2,3,4-trihydroxy-4-oxobutanoate Chemical compound C[N+](C)(C)CCO.OC(=O)[C@H](O)[C@@H](O)C([O-])=O QWJSAWXRUVVRLH-LREBCSMRSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229940009098 aspartate Drugs 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229960005336 magnesium citrate Drugs 0.000 claims description 2
- 235000002538 magnesium citrate Nutrition 0.000 claims description 2
- 239000004337 magnesium citrate Substances 0.000 claims description 2
- 229940091250 magnesium supplement Drugs 0.000 claims description 2
- 229940095060 magnesium tartrate Drugs 0.000 claims description 2
- MUZDLCBWNVUYIR-ZVGUSBNCSA-L magnesium;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Mg+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O MUZDLCBWNVUYIR-ZVGUSBNCSA-L 0.000 claims description 2
- QUIOHQITLKCGNW-TYYBGVCCSA-L magnesium;(e)-but-2-enedioate Chemical compound [Mg+2].[O-]C(=O)\C=C\C([O-])=O QUIOHQITLKCGNW-TYYBGVCCSA-L 0.000 claims description 2
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 229940066528 trichloroacetate Drugs 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 7
- 210000005226 corpus cavernosum Anatomy 0.000 description 6
- 150000003180 prostaglandins Chemical class 0.000 description 6
- 210000003899 penis Anatomy 0.000 description 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000004907 flux Effects 0.000 description 4
- 230000004913 activation Effects 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- 229960000711 alprostadil Drugs 0.000 description 2
- 230000001713 cholinergic effect Effects 0.000 description 2
- 238000009552 doppler ultrasonography Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 2
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- 239000003071 vasodilator agent Substances 0.000 description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- WIZMKNQXIAYADR-UHFFFAOYSA-N 3-hydroxy-6-methyl-4-oxo-3-[(trimethylazaniumyl)methyl]heptanoate Chemical compound C(CC(C)C)(=O)C(O)(C[N+](C)(C)C)CC([O-])=O WIZMKNQXIAYADR-UHFFFAOYSA-N 0.000 description 1
- UCTWMZQNUQWSLP-UHFFFAOYSA-N Adrenaline Natural products CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 1
- 200000000007 Arterial disease Diseases 0.000 description 1
- 206010061666 Autonomic neuropathy Diseases 0.000 description 1
- 206010052004 Organic erectile dysfunction Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940102884 adrenalin Drugs 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 230000002567 autonomic effect Effects 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 230000001856 erectile effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000001129 nonadrenergic effect Effects 0.000 description 1
- 230000002536 noncholinergic effect Effects 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the present invention relates to the use of an alkanoyl L-carnitine for the treatment of the erectile dysfunction.
- the erectile dysfunction is a syndrome characterised by a persistent inability to obtain or maintain a penis erection, for a time sufficient for a sexual intercourse.
- the current knowledge indicates that the relaxation of the smooth musculature of the corpus cavernosum which is necessary for the erection is due to a non adrenergic, non cholinergic mechanism, mediated by nitric oxide (ON), in which prostaglandin (PG) is involved (Medicina Pratica, 2000; 12-16).
- ON nitric oxide
- PG prostaglandin
- the maximum relaxation level may not be sufficient to permit an haematic flux sufficient for a normal erection.
- VIP Vasoactive Intestinal Peptides
- cGMP guanosin mono phosphate cyclic
- alkanoyl L-carnitines wherein the alkanoyl group, linear or branched, has 2-6 carbon atoms, or a pharmaceutically acceptable salt thereof are useful agents for treating the erectile dysfunction.
- pharmacologically acceptable salt of an alkanoyl L-carnitine is any salt of the latter with an acid that does not give rise to unwanted toxic or side effects.
- Non-limiting examples of pharmacologically acceptable salts of alkanoyl L-carnitines are chloride, bromide, orotate, acid aspartate, acid citrate, magnesium citrate, acid phosphate, fumarate and acid fumarate, magnesium fumarate, lactate, maleate, acid maleate, mucate, acid oxalate, pamoate, acid pamoate, acid sulphate, glucose phosphate, tartrate, acid tartrate, magnesium tartrate, 2-amino ethansulphonate, magnesium 2-amino etansulphonate, Choline tartrate and trichloroacetate.
- alkanoyl L-carnitines are acetyl, propionyl, butyryl, isobutyryl, valeryl and isovalery L-carnitine.
- a further object of the present invention is the use of an alkanoyl L-carnitine for preparing a medicine for the treatment of erectile dysfunction in patients suffering from diabetes mellitus.
- propionyl L-carnitine is preferred.
- “useful drugs” it is intended any drug useful for treating E.D.
- a further object of the present invention are pharmaceutical compositions comprising as active ingredient an alkanoyl L-carnitine in combination with one or more of said useful drugs, and at least an excipient and/or diluent pharmaceutically acceptable.
- Non-limiting examples of said useful drugs are sildenafil, apomorphine, prostaglandin E1, pentolamine or papaverine.
- a further object of the present invention is the use of an alkanoyl L-carnitine, or a pharmaceutical acceptable salt thereof, in combination with one or more of said useful drugs, for preparing a medicine for the treatment of erectile dysfunction.
- a further object of the present invention is the use of an alkanoyl L-carnitine in combination with one or more of said useful drugs, for preparing a medicine for the treatment of erectile dysfunction in patients affected by diabetes mellitus.
- a further object of the present invention is the use of an alkanoyl L-carnitine in combination with one or more of said useful drugs, for preparing a medicine for the treatment of erectile dysfunction, wherein said patients do not respond to the treatment with said useful drugs.
- a further object of the present invention is the use of an alkanoyl L-carnitine in combination with one or more of said useful drugs, for preparing a medicine for the treatment of erectile dysfunction in patients suffering from diabetes mellitus, wherein said patients do not respond to the treatment with said useful drugs.
- propionyl L-carnitine is preferred.
- alkanoyl L-carnitines and the useful drugs above mentioned can be prepared for a simultaneous, sequential or separated administration.
- the daily dose will depend, according to the judgement of the primary care physician, on the patient's weight, age and general condition, it is generally advisable to administer 0.5 to 4 g/die of alkanoyl L-carnitine or a stoichiometrically equivalent amount of one of its pharmacologically acceptable salts. 1-2 g/die are preferred.
- the of administration regimen of the two active ingredients will depend on the primary care physician's judgement, the patient's weight, age and general conditions, it is generally advisable to administer the alkanoyl L-carnitine daily and said combined useful drug twice weekly.
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/649,796 US20070117762A1 (en) | 2001-12-04 | 2007-01-05 | Use of an alkanoyl L-carnitine for the treatment of the erectile dysfunction |
| US13/280,749 US8343979B2 (en) | 2001-12-04 | 2011-10-25 | Use of alkanoyl L-carnitine for the treatment of erectile dysfunction |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001RM000708A ITRM20010708A1 (it) | 2001-12-04 | 2001-12-04 | Uso di una alcanoil l-carnitina per il trattamento della disfunzione erettile. |
| ITRM2001A000708 | 2001-12-04 | ||
| PCT/IT2002/000758 WO2003047563A1 (en) | 2001-12-04 | 2002-12-04 | Use of alkanoyl l-carnitine for the treatment of erectile dysfunction |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IT2002/000758 A-371-Of-International WO2003047563A1 (en) | 2001-12-04 | 2002-12-04 | Use of alkanoyl l-carnitine for the treatment of erectile dysfunction |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/649,796 Division US20070117762A1 (en) | 2001-12-04 | 2007-01-05 | Use of an alkanoyl L-carnitine for the treatment of the erectile dysfunction |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20050080018A1 true US20050080018A1 (en) | 2005-04-14 |
Family
ID=11455907
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/497,498 Abandoned US20050080018A1 (en) | 2001-12-04 | 2002-12-04 | Use of alkanoyl l-carnitine for the treatment of erectile dysfunction |
| US11/649,796 Abandoned US20070117762A1 (en) | 2001-12-04 | 2007-01-05 | Use of an alkanoyl L-carnitine for the treatment of the erectile dysfunction |
| US13/280,749 Expired - Fee Related US8343979B2 (en) | 2001-12-04 | 2011-10-25 | Use of alkanoyl L-carnitine for the treatment of erectile dysfunction |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/649,796 Abandoned US20070117762A1 (en) | 2001-12-04 | 2007-01-05 | Use of an alkanoyl L-carnitine for the treatment of the erectile dysfunction |
| US13/280,749 Expired - Fee Related US8343979B2 (en) | 2001-12-04 | 2011-10-25 | Use of alkanoyl L-carnitine for the treatment of erectile dysfunction |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US20050080018A1 (ja) |
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| AT (1) | ATE309800T1 (ja) |
| AU (1) | AU2002365847A1 (ja) |
| CA (1) | CA2465471C (ja) |
| DE (1) | DE60207442T2 (ja) |
| DK (1) | DK1450782T3 (ja) |
| ES (1) | ES2250749T3 (ja) |
| HU (1) | HU229214B1 (ja) |
| IT (1) | ITRM20010708A1 (ja) |
| MX (1) | MXPA04005269A (ja) |
| PL (1) | PL211211B1 (ja) |
| SI (1) | SI1450782T1 (ja) |
| WO (1) | WO2003047563A1 (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITRM20040561A1 (it) * | 2004-11-11 | 2005-02-11 | Sigma Tau Ind Farmaceuti | Uso della acetil l-carnitina in combinazione con propionil l-carnitina e sildenafil per il trattamento della disfunzione erettile. |
| IT1397867B1 (it) * | 2010-02-03 | 2013-02-04 | Brotzu | Liposomi contenenti prostaglandina e1 (pge1), formulazioni che li contengono e loro uso |
| US20140303098A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| CN105377266A (zh) | 2013-04-18 | 2016-03-02 | 勃林格殷格翰国际有限公司 | 药物组合物、治疗方法及其用途 |
| US20180104268A1 (en) * | 2015-04-30 | 2018-04-19 | Boehringer Ingelheim International Gmbh | Methods and pharmaceutical compositions comprising a sglt2 inhibitor for treating or improving erectile dysfunction |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040087515A1 (en) * | 1999-04-12 | 2004-05-06 | Butler Terri L. | Compositions methods for improving cardio vascular function |
Family Cites Families (7)
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| 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 |
| ATE187329T1 (de) * | 1996-03-04 | 1999-12-15 | Sigma Tau Ind Farmaceuti | Carnitinderivat als arzneimittel zur behandlung von arteriosklerose obliterans |
| IT1290801B1 (it) * | 1996-07-05 | 1998-12-11 | Mendes Srl | Uso della acetil l-carnitina, della isovaleril l-carnitina, della propionil l-carnitina o dei loro sali farmacologicamente accettabili |
| US6133281A (en) * | 1996-10-24 | 2000-10-17 | Harbor-Ucla Research And Education Institute | NMDA receptor blockers in the therapy of urogenital disease |
| IT1293539B1 (it) * | 1997-07-16 | 1999-03-01 | Sigma Tau Ind Farmaceuti | Composizione nutritiva per soggetti in stato di debilitazione causato da stress |
| US6241471B1 (en) * | 1999-08-26 | 2001-06-05 | General Electric Co. | Turbine bucket tip shroud reinforcement |
| IT1306722B1 (it) * | 1999-10-08 | 2001-10-02 | Sigma Tau Healthscience Spa | Composizione per la prevenzione e/o il trattamento di disfunzionicircolatorie, comprendente derivati della l-carnitina ed estratti di |
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2001
- 2001-12-04 IT IT2001RM000708A patent/ITRM20010708A1/it unknown
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2002
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- 2002-12-04 WO PCT/IT2002/000758 patent/WO2003047563A1/en active IP Right Grant
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- 2002-12-04 DE DE60207442T patent/DE60207442T2/de not_active Expired - Lifetime
- 2002-12-04 US US10/497,498 patent/US20050080018A1/en not_active Abandoned
- 2002-12-04 KR KR1020047007882A patent/KR100907938B1/ko active IP Right Grant
- 2002-12-04 AU AU2002365847A patent/AU2002365847A1/en not_active Abandoned
- 2002-12-04 JP JP2003548819A patent/JP4370169B2/ja not_active Expired - Fee Related
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- 2002-12-04 EP EP02804338A patent/EP1450782B9/en not_active Expired - Lifetime
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040087515A1 (en) * | 1999-04-12 | 2004-05-06 | Butler Terri L. | Compositions methods for improving cardio vascular function |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2465471C (en) | 2010-10-19 |
| ITRM20010708A1 (it) | 2003-06-04 |
| ITRM20010708A0 (it) | 2001-12-04 |
| PL211211B1 (pl) | 2012-04-30 |
| US8343979B2 (en) | 2013-01-01 |
| SI1450782T1 (sl) | 2006-02-28 |
| HU229214B1 (hu) | 2013-09-30 |
| DK1450782T3 (da) | 2006-02-20 |
| ATE309800T1 (de) | 2005-12-15 |
| JP4370169B2 (ja) | 2009-11-25 |
| HUP0402062A3 (en) | 2012-09-28 |
| US20120041005A1 (en) | 2012-02-16 |
| WO2003047563A1 (en) | 2003-06-12 |
| JP2005511655A (ja) | 2005-04-28 |
| AU2002365847A1 (en) | 2003-06-17 |
| KR20050044594A (ko) | 2005-05-12 |
| EP1450782B1 (en) | 2005-11-16 |
| EP1450782A1 (en) | 2004-09-01 |
| MXPA04005269A (es) | 2004-10-11 |
| DE60207442D1 (de) | 2005-12-22 |
| EP1450782B9 (en) | 2006-05-17 |
| CA2465471A1 (en) | 2003-06-12 |
| DE60207442T2 (de) | 2006-07-27 |
| US20070117762A1 (en) | 2007-05-24 |
| KR100907938B1 (ko) | 2009-07-16 |
| HUP0402062A2 (hu) | 2005-02-28 |
| PL371131A1 (en) | 2005-06-13 |
| ES2250749T3 (es) | 2006-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A., Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KOVERECH, ALEARDO;LENZI, ANDREA;REEL/FRAME:015951/0724 Effective date: 20040430 |
|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |