NO327742B1 - Estere av L-karnitin eller alkanoyl L-karnitiner, anvendelse derav for fremstilling av liposomer, de oppnadde liposomer samt anvendelse derav samt farmasoytiske og kosmetiske sammensetninger - Google Patents

Estere av L-karnitin eller alkanoyl L-karnitiner, anvendelse derav for fremstilling av liposomer, de oppnadde liposomer samt anvendelse derav samt farmasoytiske og kosmetiske sammensetninger Download PDF

Info

Publication number: NO327742B1
Authority: NO; Norway
Prior art keywords: liposome; liposomes; acid; ester; group
Prior art date: 1999-04-13

Application number

NO20014985A

Other languages

English (en)

Norwegian (no)

Other versions

NO20014985L (no

NO20014985D0 (no

Inventor

Claudio Pisano

Mari Ornella Tinti

Mose Santaniello

Luciana Critelli

Giovanni Salvatori

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.)

1999-04-13

Filing date

2001-10-12

Publication date

2009-09-14

2001-10-12 Application filed by Sigma Tau Ind Farmaceuti filed Critical Sigma Tau Ind Farmaceuti

2001-10-12 Publication of NO20014985L publication Critical patent/NO20014985L/no

2001-10-12 Publication of NO20014985D0 publication Critical patent/NO20014985D0/no

2009-09-14 Publication of NO327742B1 publication Critical patent/NO327742B1/no

Links

239000002502 liposome Substances 0.000 title claims description 141
238000002360 preparation method Methods 0.000 title claims description 55
239000000203 mixture Substances 0.000 title claims description 46
-1 alkanoyl L-carnitines Chemical class 0.000 title claims description 22
PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title claims description 16
239000002537 cosmetic Substances 0.000 title claims description 10
150000002148 esters Chemical class 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims description 67
150000002632 lipids Chemical class 0.000 claims description 51
229940127093 camptothecin Drugs 0.000 claims description 39
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 28
239000013612 plasmid Substances 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 23
229960001592 paclitaxel Drugs 0.000 claims description 22
229930012538 Paclitaxel Natural products 0.000 claims description 21
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 20
239000000126 substance Substances 0.000 claims description 20
GCIOXBFOKSICTP-UHFFFAOYSA-N (3-hexadecanoyloxy-2,5-dihydroxy-4-oxopentyl) hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)C(C(=O)CO)OC(=O)CCCCCCCCCCCCCCC GCIOXBFOKSICTP-UHFFFAOYSA-N 0.000 claims description 19
230000000694 effects Effects 0.000 claims description 18
229940079593 drug Drugs 0.000 claims description 17
108090000623 proteins and genes Proteins 0.000 claims description 17
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 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 14
KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 11
238000001415 gene therapy Methods 0.000 claims description 11
108091033319 polynucleotide Proteins 0.000 claims description 11
239000002157 polynucleotide Substances 0.000 claims description 11
102000040430 polynucleotide Human genes 0.000 claims description 11
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 9
102000004169 proteins and genes Human genes 0.000 claims description 9
108090000765 processed proteins & peptides Proteins 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
239000002246 antineoplastic agent Substances 0.000 claims description 7
235000012000 cholesterol Nutrition 0.000 claims description 7
RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 claims description 6
229910019142 PO4 Inorganic materials 0.000 claims description 5
150000001450 anions Chemical class 0.000 claims description 5
230000002163 immunogen Effects 0.000 claims description 5
102000004196 processed proteins & peptides Human genes 0.000 claims description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 4
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
229940009098 aspartate Drugs 0.000 claims description 4
125000004432 carbon atom Chemical group C* 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
239000008194 pharmaceutical composition Substances 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
239000010452 phosphate Substances 0.000 claims description 4
229940095064 tartrate Drugs 0.000 claims description 4
SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims description 3
LRCNOZRCYBNMEP-SECBINFHSA-N O-isobutyryl-L-carnitine Chemical compound CC(C)C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C LRCNOZRCYBNMEP-SECBINFHSA-N 0.000 claims description 3
230000001093 anti-cancer Effects 0.000 claims description 3
230000000884 anti-protozoa Effects 0.000 claims description 3
229940121375 antifungal agent Drugs 0.000 claims description 3
IGQBPDJNUXPEMT-SNVBAGLBSA-N isovaleryl-L-carnitine Chemical compound CC(C)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C IGQBPDJNUXPEMT-SNVBAGLBSA-N 0.000 claims description 3
239000007922 nasal spray Substances 0.000 claims description 3
229960005486 vaccine Drugs 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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229940097496 nasal spray Drugs 0.000 claims description 2
125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000000668 oral spray Substances 0.000 claims description 2
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 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
125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
230000001772 anti-angiogenic effect Effects 0.000 claims 2
230000000844 anti-bacterial effect Effects 0.000 claims 2
230000000843 anti-fungal effect Effects 0.000 claims 2
230000000840 anti-viral effect Effects 0.000 claims 2
210000000748 cardiovascular system Anatomy 0.000 claims 2
239000004037 angiogenesis inhibitor Substances 0.000 claims 1
230000003217 anti-cancerogenic effect Effects 0.000 claims 1
229940041678 oral spray Drugs 0.000 claims 1
PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 53
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 33
108020004414 DNA Proteins 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000000725 suspension Substances 0.000 description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
210000004027 cell Anatomy 0.000 description 25
UIVFUQKYVFCEKJ-OPTOVBNMSA-N gimatecan Chemical compound C1=CC=C2C(\C=N\OC(C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UIVFUQKYVFCEKJ-OPTOVBNMSA-N 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
125000002091 cationic group Chemical group 0.000 description 22
238000012360 testing method Methods 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 17
238000001890 transfection Methods 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
238000004128 high performance liquid chromatography Methods 0.000 description 16
210000004072 lung Anatomy 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
238000001727 in vivo Methods 0.000 description 14
239000007787 solid Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 12
239000012528 membrane Substances 0.000 description 12
239000003480 eluent Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
108060001084 Luciferase Proteins 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 10
239000002953 phosphate buffered saline Substances 0.000 description 10
238000004879 turbidimetry Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000000523 sample Substances 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 8
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241000699670 Mus sp. Species 0.000 description 7
230000003834 intracellular effect Effects 0.000 description 7
230000003287 optical effect Effects 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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229960000583 acetic acid Drugs 0.000 description 6
210000000170 cell membrane Anatomy 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
230000003993 interaction Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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239000002904 solvent Substances 0.000 description 6
125000006527 (C1-C5) alkyl group Chemical group 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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231100000135 cytotoxicity Toxicity 0.000 description 5
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238000001476 gene delivery Methods 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
238000004020 luminiscence type Methods 0.000 description 5
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 5
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Dispersion Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Birds (AREA)
Immunology (AREA)
Molecular Biology (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Biophysics (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Emergency Medicine (AREA)
Communicable Diseases (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Oncology (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Cosmetics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)

NO20014985A 1999-04-13 2001-10-12 Estere av L-karnitin eller alkanoyl L-karnitiner, anvendelse derav for fremstilling av liposomer, de oppnadde liposomer samt anvendelse derav samt farmasoytiske og kosmetiske sammensetninger NO327742B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT1999RM000220A IT1306129B1 (it)	1999-04-13	1999-04-13	Esteri della l-carnitina o di alcanoil l-carnitine utilizzabili comelipidi cationici per l'immissione intracellulare di composti
PCT/IT2000/000137 WO2000061543A2 (fr)	1999-04-13	2000-04-11	Esters de l-carnitine ou de l-carnitines alcanoyles utilises comme lipides cationiques pour un apport intracellulaire de composes actifs d'un point de vue pharmacologique

Publications (3)

Publication Number	Publication Date
NO20014985L NO20014985L (no)	2001-10-12
NO20014985D0 NO20014985D0 (no)	2001-10-12
NO327742B1 true NO327742B1 (no)	2009-09-14

Family

ID=11406659

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO20014985A NO327742B1 (no)	1999-04-13	2001-10-12	Estere av L-karnitin eller alkanoyl L-karnitiner, anvendelse derav for fremstilling av liposomer, de oppnadde liposomer samt anvendelse derav samt farmasoytiske og kosmetiske sammensetninger
NO20085413A NO336949B1 (no)	1999-04-13	2008-12-30	Anvendelse av estere av L-karnitin eller alkanoyl L-karnitiner som kationiske lipider for intracellulær avlevering av farmakologisk aktive forbindelser

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO20085413A NO336949B1 (no)	1999-04-13	2008-12-30	Anvendelse av estere av L-karnitin eller alkanoyl L-karnitiner som kationiske lipider for intracellulær avlevering av farmakologisk aktive forbindelser

Country Status (34)

Country	Link
US (4)	US6797281B1 (fr)
EP (3)	EP1183228B1 (fr)
JP (2)	JP4703855B2 (fr)
KR (2)	KR100684378B1 (fr)
CN (2)	CN100402017C (fr)
AT (2)	ATE317257T1 (fr)
AU (2)	AU776301B2 (fr)
BG (3)	BG65501B1 (fr)
BR (2)	BRPI0017460B1 (fr)
CA (2)	CA2650202C (fr)
CZ (1)	CZ302628B6 (fr)
DE (2)	DE60025961T2 (fr)
DK (2)	DK1426044T3 (fr)
EA (2)	EA006021B1 (fr)
EE (2)	EE05719B1 (fr)
ES (2)	ES2258688T3 (fr)
HK (1)	HK1045145B (fr)
HR (1)	HRP20010740B1 (fr)
HU (1)	HU229366B1 (fr)
IL (4)	IL145765A0 (fr)
IS (2)	IS2476B (fr)
IT (1)	IT1306129B1 (fr)
ME (2)	ME00113B (fr)
MX (1)	MXPA01010359A (fr)
NO (2)	NO327742B1 (fr)
NZ (2)	NZ515270A (fr)
PL (2)	PL204418B1 (fr)
PT (2)	PT1183228E (fr)
RS (3)	RS52682B (fr)
SI (2)	SI1426044T1 (fr)
SK (2)	SK287253B6 (fr)
TR (2)	TR200202358T2 (fr)
WO (1)	WO2000061543A2 (fr)
ZA (1)	ZA200109291B (fr)

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GT200500310A (es) *	2004-11-19	2006-06-19		Compuestos organicos
WO2006094203A1 (fr) *	2005-03-02	2006-09-08	Northeastern University	Vesicules phospholipidiques mitochondriotropes
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US20080213385A1 (en) *	2005-08-10	2008-09-04	Oskar Kalb	Formulations for 7- (T-Butoxy) Iminomethyl Camptothecin
US20100178325A1 (en) *	2006-08-23	2010-07-15	Biodelivery Sciences International, Inc.	Amphiphilic nucleotide cochleate compositions and methods of using the same
KR20090115856A (ko) *	2007-02-01	2009-11-09	시그마타우 인두스트리에 파르마슈티케 리우니테 에스.피.에이.	캄포테신 유도체를 함유하는 약학적 조성물
WO2008101173A2 (fr) *	2007-02-16	2008-08-21	Cornell University	Compositions et matériaux biodégradables
WO2008144881A1 (fr) *	2007-05-28	2008-12-04	Genesis Group Inc.	Élastomères biodégradables préparés par la condensation d'un acide organique di-, tri- ou tétracarboxylique et d'un diol organique
MX2009013332A (es)	2007-06-08	2010-01-25	Mannkind Corp	Inhibidores de ire-1 alfa.
JP2011514809A (ja)	2008-03-13	2011-05-12	パーキンエルマーラスインコーポレイテッド	多重検出システムのための酵素基質
EP2532649B1 (fr) *	2011-06-07	2015-04-08	Incella GmbH	Lipides aminés, leur synthèse et utilisations associées
WO2013032643A2 (fr) *	2011-08-31	2013-03-07	Dicerna Pharmaceuticals, Inc.	Lipides pouvant supporter un changement conformationnel et utilisation de ces derniers dans des formulations afin d'apporter des agents thérapeutiques à des cellules
TWI773147B (zh)	2013-03-15	2022-08-01	美商珀金埃爾默健康科技公司	關於用於溶酶體儲積症之測試的化合物及方法
CA3016457A1 (fr)	2016-03-02	2017-09-08	The Board Of Regents Of The University Of Texas System	Nanovaccin activant sting pour l'immunotherapie
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
CN115177608B (zh) *	2022-07-26	2023-12-05	南方医科大学南方医院	长链酰基肉碱类化合物在制备预防和/或治疗肝癌的药物中的应用

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1999
- 1999-04-13 IT IT1999RM000220A patent/IT1306129B1/it active
2000
- 2000-04-11 TR TR2002/02358T patent/TR200202358T2/xx unknown
- 2000-04-11 EP EP00922852A patent/EP1183228B1/fr not_active Expired - Lifetime
- 2000-04-11 AU AU43123/00A patent/AU776301B2/en not_active Ceased
- 2000-04-11 SI SI200030799T patent/SI1426044T1/sl unknown
- 2000-04-11 DE DE60025961T patent/DE60025961T2/de not_active Expired - Lifetime
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- 2000-04-11 CA CA2650202A patent/CA2650202C/fr not_active Expired - Fee Related
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- 2000-04-11 EP EP03020049A patent/EP1426044B1/fr not_active Expired - Lifetime
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2001
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- 2001-10-04 IL IL145765A patent/IL145765A/en not_active IP Right Cessation
- 2001-10-12 NO NO20014985A patent/NO327742B1/no not_active IP Right Cessation
- 2001-11-12 ZA ZA200109291A patent/ZA200109291B/en unknown
2003
- 2003-07-23 US US10/624,645 patent/US7629003B2/en not_active Expired - Fee Related
2004
- 2004-01-28 US US10/765,091 patent/US20040186175A1/en not_active Abandoned
- 2004-10-29 AU AU2004224958A patent/AU2004224958B2/en not_active Ceased
2006
- 2006-05-01 IL IL175366A patent/IL175366A/en not_active IP Right Cessation
2007
- 2007-03-27 US US11/727,526 patent/US7585519B2/en not_active Expired - Fee Related
- 2007-08-23 IL IL185486A patent/IL185486A0/en not_active IP Right Cessation
2008
- 2008-03-07 IS IS8719A patent/IS2539B/is unknown
- 2008-12-30 NO NO20085413A patent/NO336949B1/no not_active IP Right Cessation
2010
- 2010-09-21 JP JP2010210849A patent/JP5420507B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
SK14312001A3 (sk)	2002-02-05
CA2650202A1 (fr)	2000-10-19
RS20090448A (sr)	2010-06-30
MXPA01010359A (es)	2002-05-06
US20040186175A1 (en)	2004-09-23
EE200100518A (et)	2002-12-16
HUP0201446A2 (en)	2002-08-28
HK1092732A1 (en)	2007-02-16
KR20060113799A (ko)	2006-11-02
AU4312300A (en)	2000-11-14
HU229366B1 (en)	2013-11-28
HK1045145A1 (en)	2002-11-15
DK1183228T3 (da)	2005-05-17
DE60017388T2 (de)	2006-03-30
NZ515270A (en)	2004-02-27
PL351112A1 (en)	2003-03-24
PL211710B1 (pl)	2012-06-29
JP4703855B2 (ja)	2011-06-15
BG65501B1 (bg)	2008-10-31
NO20014985L (no)	2001-10-12
NO20014985D0 (no)	2001-10-12
SI1426044T1 (sl)	2006-04-30
EP1183228B1 (fr)	2005-01-12
ATE317257T1 (de)	2006-02-15
KR20010113794A (ko)	2001-12-28
DK1426044T3 (da)	2006-06-12
RS50911B (sr)	2010-08-31
US7585519B2 (en)	2009-09-08
SK288246B6 (sk)	2015-03-03
IT1306129B1 (it)	2001-05-30
KR100798499B1 (ko)	2008-01-28
US20050079209A1 (en)	2005-04-14
EP1426044A1 (fr)	2004-06-09
AU2004224958A1 (en)	2004-11-25
DE60025961T2 (de)	2006-08-17
PT1426044E (pt)	2006-06-30
NO336949B1 (no)	2015-11-30
IS2539B (is)	2009-09-15
CN100402017C (zh)	2008-07-16
CZ20013617A3 (cs)	2002-02-13
EP1183228A2 (fr)	2002-03-06
BG105971A (en)	2002-08-30
EA200101076A1 (ru)	2002-04-25
BG65312B1 (bg)	2008-01-31
CZ302628B6 (cs)	2011-08-10
ATE286873T1 (de)	2005-01-15
JP5420507B2 (ja)	2014-02-19
ES2234591T3 (es)	2005-07-01
AU2004224958B2 (en)	2007-11-22
WO2000061543A3 (fr)	2001-01-11
EA006021B1 (ru)	2005-08-25
HRP20010740A2 (en)	2002-10-31
EE05719B1 (et)	2014-08-15
US7629003B2 (en)	2009-12-08
CN1359370A (zh)	2002-07-17
ES2258688T3 (es)	2006-09-01
CN1263730C (zh)	2006-07-12
HK1045145B (en)	2006-01-27
HUP0201446A3 (en)	2002-11-28
IL145765A (en)	2007-07-04
PL204418B1 (pl)	2010-01-29
AU776301B2 (en)	2004-09-02
BR0009765B1 (pt)	2013-11-05
CA2370143C (fr)	2011-06-21
YU70201A (sh)	2004-07-15
RS52682B (sr)	2013-08-30
WO2000061543A2 (fr)	2000-10-19
JP2011042657A (ja)	2011-03-03
IL175366A0 (en)	2006-09-05
KR100684378B1 (ko)	2007-02-20
DE60017388D1 (de)	2005-02-17
NO20085413L (no)	2001-10-12
IS2476B (is)	2008-12-15
MEP24008A (en)	2010-06-10
TR200202358T2 (tr)	2002-12-23
JP2002541238A (ja)	2002-12-03
CA2370143A1 (fr)	2000-10-19
EP1435232A1 (fr)	2004-07-07
IS6095A (is)	2001-09-28
IL175366A (en)	2010-12-30
CA2650202C (fr)	2012-12-11
IL145765A0 (en)	2002-07-25
PT1183228E (pt)	2005-04-29
NZ528874A (en)	2005-09-30
SI1183228T1 (en)	2005-04-30
CN1823731A (zh)	2006-08-30
US20070190128A1 (en)	2007-08-16
BRPI0017460B1 (pt)	2016-04-19
TR200102941T2 (tr)	2002-05-21
EE05514B1 (et)	2012-02-15
IL185486A0 (en)	2008-01-06
US6797281B1 (en)	2004-09-28
EA200300745A1 (ru)	2003-12-25
DE60025961D1 (de)	2006-04-20
BG109876A (en)	2008-02-29
SK287253B6 (sk)	2010-04-07
IS8719A (is)	2008-03-07
EP1426044B1 (fr)	2006-02-08
ITRM990220A1 (it)	2000-10-13
ME00113B (fr)	2010-10-10
ZA200109291B (en)	2002-08-16
EE201100028A (et)	2011-08-15
BR0009765A (pt)	2002-01-02
EA004459B1 (ru)	2004-04-29
HRP20010740B1 (en)	2005-08-31

Legal Events

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2017-11-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO327742B1 (no)	2009-09-14	Estere av L-karnitin eller alkanoyl L-karnitiner, anvendelse derav for fremstilling av liposomer, de oppnadde liposomer samt anvendelse derav samt farmasoytiske og kosmetiske sammensetninger
CN118255678A (zh)	2024-06-28	一种可电离脂质化合物及其应用
WO2025111454A9 (fr)	2026-02-12	Lipides ionisables, nanoparticules lipidiques pour administration d'arnm et leurs procédés de fabrication
AU2007214359B2 (en)	2009-02-12	Esters of L-carnitine or alkanoyl L-carnitines useful as cationic lipids for the intracellular delivery of pharmacologically active compounds
HK1092732B (en)	2009-02-13	Esters of l-carnitine or alkanoyl l-carnitines useful as cationic lipids for the intracellular delivery of pharmacologically active compounds