NO313227B1 - Terapeutisk forbindelse - fettsyrekonjugater - Google Patents
Terapeutisk forbindelse - fettsyrekonjugater Download PDFInfo
- Publication number
- NO313227B1 NO313227B1 NO19960389A NO960389A NO313227B1 NO 313227 B1 NO313227 B1 NO 313227B1 NO 19960389 A NO19960389 A NO 19960389A NO 960389 A NO960389 A NO 960389A NO 313227 B1 NO313227 B1 NO 313227B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- indomethacin
- compound according
- tris
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 138
- 239000000194 fatty acid Substances 0.000 title claims abstract description 47
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 46
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 46
- 230000001225 therapeutic effect Effects 0.000 title abstract description 10
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims abstract description 45
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 44
- 125000002252 acyl group Chemical group 0.000 claims abstract description 41
- 230000003637 steroidlike Effects 0.000 claims abstract description 29
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 6
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 120
- 229960000905 indomethacin Drugs 0.000 claims description 60
- 239000007983 Tris buffer Substances 0.000 claims description 53
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 48
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 31
- 229960001680 ibuprofen Drugs 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- -1 zomepirak Chemical compound 0.000 claims description 18
- 235000001014 amino acid Nutrition 0.000 claims description 15
- 150000001413 amino acids Chemical class 0.000 claims description 15
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 14
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 14
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 claims description 12
- 125000006850 spacer group Chemical group 0.000 claims description 12
- 239000004471 Glycine Substances 0.000 claims description 11
- MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 claims description 10
- 229940068372 acetyl salicylate Drugs 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229960001860 salicylate Drugs 0.000 claims description 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 10
- 150000003254 radicals Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 235000004279 alanine Nutrition 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 claims description 6
- 229960000616 diflunisal Drugs 0.000 claims description 6
- HAWWPSYXSLJRBO-UHFFFAOYSA-N fendosal Chemical compound C1=C(O)C(C(=O)O)=CC(N2C(=CC=3C4=CC=CC=C4CCC=32)C=2C=CC=CC=2)=C1 HAWWPSYXSLJRBO-UHFFFAOYSA-N 0.000 claims description 6
- 229950005416 fendosal Drugs 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229960000953 salsalate Drugs 0.000 claims description 6
- RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 claims description 5
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims description 5
- SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 claims description 5
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 5
- JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 claims description 5
- FSQKKOOTNAMONP-UHFFFAOYSA-N acemetacin Chemical compound CC1=C(CC(=O)OCC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 FSQKKOOTNAMONP-UHFFFAOYSA-N 0.000 claims description 5
- 229960004892 acemetacin Drugs 0.000 claims description 5
- 229960005430 benoxaprofen Drugs 0.000 claims description 5
- 229960003184 carprofen Drugs 0.000 claims description 5
- IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 claims description 5
- NKPPORKKCMYYTO-DHZHZOJOSA-N cinmetacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)\C=C\C1=CC=CC=C1 NKPPORKKCMYYTO-DHZHZOJOSA-N 0.000 claims description 5
- 229950011171 cinmetacin Drugs 0.000 claims description 5
- CLOMYZFHNHFSIQ-UHFFFAOYSA-N clonixin Chemical compound CC1=C(Cl)C=CC=C1NC1=NC=CC=C1C(O)=O CLOMYZFHNHFSIQ-UHFFFAOYSA-N 0.000 claims description 5
- 229960001209 clonixin Drugs 0.000 claims description 5
- 229960001259 diclofenac Drugs 0.000 claims description 5
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 5
- 229960001419 fenoprofen Drugs 0.000 claims description 5
- 229960004369 flufenamic acid Drugs 0.000 claims description 5
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 claims description 5
- NOOCSNJCXJYGPE-UHFFFAOYSA-N flunixin Chemical compound C1=CC=C(C(F)(F)F)C(C)=C1NC1=NC=CC=C1C(O)=O NOOCSNJCXJYGPE-UHFFFAOYSA-N 0.000 claims description 5
- 229960000588 flunixin Drugs 0.000 claims description 5
- 229960002390 flurbiprofen Drugs 0.000 claims description 5
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 5
- 229960004187 indoprofen Drugs 0.000 claims description 5
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 5
- 229960000991 ketoprofen Drugs 0.000 claims description 5
- 229940013798 meclofenamate Drugs 0.000 claims description 5
- 229960003464 mefenamic acid Drugs 0.000 claims description 5
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 claims description 5
- 229960002009 naproxen Drugs 0.000 claims description 5
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 5
- 229960000916 niflumic acid Drugs 0.000 claims description 5
- PIDSZXPFGCURGN-UHFFFAOYSA-N pirprofen Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1CC=CC1 PIDSZXPFGCURGN-UHFFFAOYSA-N 0.000 claims description 5
- 229960000851 pirprofen Drugs 0.000 claims description 5
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 claims description 5
- 229960000894 sulindac Drugs 0.000 claims description 5
- 229960002905 tolfenamic acid Drugs 0.000 claims description 5
- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 claims description 5
- 229960001017 tolmetin Drugs 0.000 claims description 5
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 claims 1
- 150000002169 ethanolamines Chemical class 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229960000281 trometamol Drugs 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000004128 high performance liquid chromatography Methods 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 15
- 206010030113 Oedema Diseases 0.000 description 13
- 125000005647 linker group Chemical group 0.000 description 13
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000004224 protection Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- 206010015150 Erythema Diseases 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 231100000321 erythema Toxicity 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000002035 prolonged effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- AXAVXPMQTGXXJZ-UHFFFAOYSA-N 2-aminoacetic acid;2-amino-2-(hydroxymethyl)propane-1,3-diol Chemical compound NCC(O)=O.OCC(N)(CO)CO AXAVXPMQTGXXJZ-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- 101100266802 Escherichia coli (strain K12) ychF gene Proteins 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 101100167281 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CIN4 gene Proteins 0.000 description 4
- 101100016060 Schizosaccharomyces pombe (strain 972 / ATCC 24843) gtp1 gene Proteins 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- 238000002953 preparative HPLC Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 229940106681 chloroacetic acid Drugs 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000004820 halides Chemical group 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- NNWAARLSYSBVPB-UHFFFAOYSA-N 1h-imidazole-4,5-dicarboxamide Chemical compound NC(=O)C=1N=CNC=1C(N)=O NNWAARLSYSBVPB-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 101150072179 ATP1 gene Proteins 0.000 description 2
- 101150015935 ATP2 gene Proteins 0.000 description 2
- 101100003366 Arabidopsis thaliana ATPA gene Proteins 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 102100021649 Elongator complex protein 6 Human genes 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 101100065219 Homo sapiens ELP6 gene Proteins 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 206010058679 Skin oedema Diseases 0.000 description 2
- 206010042496 Sunburn Diseases 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 101150081894 atp3 gene Proteins 0.000 description 2
- 101150026213 atpB gene Proteins 0.000 description 2
- 101150105046 atpI gene Proteins 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000003029 glycosylic effect Effects 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- 108700039855 mouse a Proteins 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical group C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HOHIAEPXOHCCGW-UHFFFAOYSA-N 2-aminoethanesulfonic acid Chemical compound NCCS(O)(=O)=O.NCCS(O)(=O)=O HOHIAEPXOHCCGW-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- BBHJTCADCKZYSO-UHFFFAOYSA-N 4-(4-ethylcyclohexyl)benzonitrile Chemical compound C1CC(CC)CCC1C1=CC=C(C#N)C=C1 BBHJTCADCKZYSO-UHFFFAOYSA-N 0.000 description 1
- 101150072037 ATP6V0C gene Proteins 0.000 description 1
- 102100022936 ATPase inhibitor, mitochondrial Human genes 0.000 description 1
- 102000003741 Actin-related protein 3 Human genes 0.000 description 1
- 108090000104 Actin-related protein 3 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 description 1
- 101000902767 Homo sapiens ATPase inhibitor, mitochondrial Proteins 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000011804 SKH1 hairless mouse Methods 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- QVTMGLKIERGFFS-UHFFFAOYSA-N acetic acid;isocyanatoethane Chemical compound CC(O)=O.CCN=C=O QVTMGLKIERGFFS-UHFFFAOYSA-N 0.000 description 1
- 231100000569 acute exposure Toxicity 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000341 effect on erythema Effects 0.000 description 1
- 230000002874 effect on oedema Effects 0.000 description 1
- 239000012149 elution buffer Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 150000002190 fatty acyls Chemical class 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000030304 gastrointestinal bleeding Diseases 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036732 histological change Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 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 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940100613 topical solution Drugs 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom
- C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPM032593 | 1993-08-02 | ||
PCT/AU1994/000440 WO1995004030A1 (en) | 1993-08-02 | 1994-08-02 | Therapeutic compound - fatty acid conjugates |
Publications (3)
Publication Number | Publication Date |
---|---|
NO960389D0 NO960389D0 (no) | 1996-01-30 |
NO960389L NO960389L (no) | 1996-01-30 |
NO313227B1 true NO313227B1 (no) | 2002-09-02 |
Family
ID=3777106
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19960389A NO313227B1 (no) | 1993-08-02 | 1996-01-30 | Terapeutisk forbindelse - fettsyrekonjugater |
Country Status (14)
Country | Link |
---|---|
US (2) | US5792786A (da) |
EP (1) | EP0712389B1 (da) |
JP (1) | JPH09501655A (da) |
CN (1) | CN1125040C (da) |
AT (1) | ATE198880T1 (da) |
CA (1) | CA2167818A1 (da) |
DE (1) | DE69426629T2 (da) |
DK (1) | DK0712389T3 (da) |
ES (1) | ES2156156T3 (da) |
FI (1) | FI960504A (da) |
NO (1) | NO313227B1 (da) |
NZ (1) | NZ269773A (da) |
RU (1) | RU2137755C1 (da) |
WO (1) | WO1995004030A1 (da) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AUPM747694A0 (en) * | 1994-08-16 | 1994-09-08 | Commonwealth Scientific And Industrial Research Organisation | Delivery of nucleic acids and peptides |
WO1996022303A1 (en) * | 1995-01-16 | 1996-07-25 | Commonwealth Scientific And Industrial Research Organisation | Therapeutic compound - fatty acid conjugates |
USRE40546E1 (en) * | 1996-05-01 | 2008-10-21 | Scarista, Ltd. | 1,3-Propane diol esters and ethers and methods for their use in drug delivery |
EP0823897B1 (en) * | 1995-05-01 | 2004-07-28 | Scarista Limited | Nicotinic acid esters and pharmaceutical compositions containing them |
MY118354A (en) * | 1995-05-01 | 2004-10-30 | Scarista Ltd | 1,3-propane diol derivatives as bioactive compounds |
AUPN741696A0 (en) * | 1996-01-05 | 1996-01-25 | Commonwealth Scientific And Industrial Research Organisation | Delivery of nucleic acids ii |
DE19631189A1 (de) | 1996-08-02 | 1998-02-05 | Max Delbrueck Centrum | Neuartige kationische Amphiphile für den liposomalen Gentransfer |
AUPP751398A0 (en) * | 1998-12-04 | 1999-01-07 | Commonwealth Scientific And Industrial Research Organisation | Methotrexate derivatives |
US6762182B1 (en) | 1999-01-07 | 2004-07-13 | Vanderbilt University | Converting cox inhibition compounds that are not COX-2 selective inhibitors to derivatives that are COX-2 selective inhibitors |
US6207700B1 (en) | 1999-01-07 | 2001-03-27 | Vanderbilt University | Amide derivatives for antiangiogenic and/or antitumorigenic use |
US6716452B1 (en) * | 2000-08-22 | 2004-04-06 | New River Pharmaceuticals Inc. | Active agent delivery systems and methods for protecting and administering active agents |
US6306890B1 (en) | 1999-08-30 | 2001-10-23 | Vanderbilt University | Esters derived from indolealkanols and novel amides derived from indolealkylamides that are selective COX-2 inhibitors |
US8394813B2 (en) | 2000-11-14 | 2013-03-12 | Shire Llc | Active agent delivery systems and methods for protecting and administering active agents |
TWI255186B (en) * | 2001-06-05 | 2006-05-21 | Control Delivery Sys Inc | Sustained-release analgesic compounds |
US20060014697A1 (en) | 2001-08-22 | 2006-01-19 | Travis Mickle | Pharmaceutical compositions for prevention of overdose or abuse |
US7169752B2 (en) | 2003-09-30 | 2007-01-30 | New River Pharmaceuticals Inc. | Compounds and compositions for prevention of overdose of oxycodone |
US20030148379A1 (en) * | 2002-02-06 | 2003-08-07 | Roitman Daniel B. | Methods for making microbar encoders for bioprobes |
BRPI0410792B8 (pt) * | 2003-05-29 | 2021-05-25 | New River Pharmaceuticals Inc | compostos de anfetamina resistentes à dependencia |
US7491744B2 (en) | 2004-04-26 | 2009-02-17 | Vanderbilt University | Indoleacetic acid and indenacetic acid derivatives as therapeutic agents with reduced gastrointestinal toxicity |
US8512734B2 (en) | 2004-07-05 | 2013-08-20 | Katholieke Universiteit Leuven, K.U.Leuven R&D | Biocompatible coating of medical devices |
US7691364B2 (en) * | 2005-01-28 | 2010-04-06 | Bezwada Biomedical, Llc | Functionalized drugs and polymers derived therefrom |
EP2322183B1 (en) * | 2006-06-01 | 2014-10-22 | Santen SAS | Use of prodrugs for ocular intravitreous administration |
US7736624B2 (en) | 2006-06-19 | 2010-06-15 | Univ Vanderbilt | Methods and compositions for diagnostic and therapeutic targeting of COX-2 |
CN101500984A (zh) * | 2006-07-27 | 2009-08-05 | 于崇曦 | 具有快速皮肤穿透速度的带正电荷的水溶性酮洛芬及相关化合物的前药 |
US9085527B2 (en) | 2008-07-08 | 2015-07-21 | Catabasis Pharmaceuticals, Inc. | Fatty acid acylated salicylates and their uses |
MX2011000273A (es) | 2008-07-08 | 2011-05-23 | Catabasis Pharmaceuticals Inc | Salicilatos acetilados con acidos grasos y sus usos. |
EP3078374B1 (en) | 2011-10-17 | 2019-06-19 | Vanderbilt University | Indomethacin analogs for the treatment of castrate-resistant prostate cancer |
JP6333244B2 (ja) * | 2012-06-26 | 2018-05-30 | ポリアクティヴァ・プロプライエタリー・リミテッド | ポリマー−nsaidコンジュゲート |
BR112017014194A2 (pt) * | 2015-01-23 | 2018-01-09 | Novartis Ag | conjugados de ácido graxo de apelina sintéticos com meia-vida melhorada |
WO2024018762A1 (ja) * | 2022-07-19 | 2024-01-25 | 国立大学法人北海道大学 | pH感受性カチオン性脂質及び脂質ナノ粒子 |
CN116496193A (zh) * | 2023-03-10 | 2023-07-28 | 圣诺生物医药技术(苏州)有限公司 | 一种氨基酸脂质形成的纳米递送系统及其应用 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3686238A (en) * | 1970-01-19 | 1972-08-22 | Syntex Corp | Glycerol esterified with 2-naphthyl-acetic acids and fatty acids |
BE871709A (fr) * | 1978-10-31 | 1979-02-15 | Abbott Lab | Procede de preparation de composes doues d'une activite anti-inflammatoire |
DE3904119A1 (de) | 1989-02-11 | 1990-08-16 | Hoechst Ag | Polymerfixiertes methotrexat, verfahren zur herstellung und verwendung |
ES2084150T3 (es) * | 1989-12-22 | 1996-05-01 | Commw Scient Ind Res Org | Aminoacidos, peptidos o sus derivados asociados a las grasas. |
WO1992016236A1 (en) | 1991-03-19 | 1992-10-01 | Rajadhyaksha Vithal J | Compositions and method comprising aminoalcohol derivatives as membrane penetration enhancers |
ATE191147T1 (de) * | 1991-07-26 | 2000-04-15 | Commw Scient Ind Res Org | System der bereitstellung eines impfstoffes auf peptidbasis, das sein eigenes adjuvans bildet, und seine herstellung |
DE4311987A1 (de) | 1993-04-07 | 1994-10-13 | Schering Ag | Neue Glucocorticoide |
-
1994
- 1994-08-02 US US08/592,399 patent/US5792786A/en not_active Expired - Fee Related
- 1994-08-02 DE DE69426629T patent/DE69426629T2/de not_active Expired - Fee Related
- 1994-08-02 DK DK94922189T patent/DK0712389T3/da active
- 1994-08-02 RU RU96104379A patent/RU2137755C1/ru not_active IP Right Cessation
- 1994-08-02 CA CA002167818A patent/CA2167818A1/en not_active Abandoned
- 1994-08-02 ES ES94922189T patent/ES2156156T3/es not_active Expired - Lifetime
- 1994-08-02 EP EP94922189A patent/EP0712389B1/en not_active Expired - Lifetime
- 1994-08-02 CN CN94192985A patent/CN1125040C/zh not_active Expired - Fee Related
- 1994-08-02 AT AT94922189T patent/ATE198880T1/de not_active IP Right Cessation
- 1994-08-02 WO PCT/AU1994/000440 patent/WO1995004030A1/en active IP Right Grant
- 1994-08-02 JP JP7505456A patent/JPH09501655A/ja active Pending
- 1994-08-02 NZ NZ269773A patent/NZ269773A/en unknown
-
1996
- 1996-01-30 NO NO19960389A patent/NO313227B1/no not_active IP Right Cessation
- 1996-02-02 FI FI960504A patent/FI960504A/fi not_active IP Right Cessation
-
1998
- 1998-01-30 US US09/016,633 patent/US6353124B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US5792786A (en) | 1998-08-11 |
WO1995004030A1 (en) | 1995-02-09 |
DE69426629T2 (de) | 2001-08-02 |
CN1125040C (zh) | 2003-10-22 |
NO960389D0 (no) | 1996-01-30 |
US6353124B1 (en) | 2002-03-05 |
DK0712389T3 (da) | 2001-06-05 |
EP0712389B1 (en) | 2001-01-24 |
JPH09501655A (ja) | 1997-02-18 |
RU2137755C1 (ru) | 1999-09-20 |
CN1128531A (zh) | 1996-08-07 |
ES2156156T3 (es) | 2001-06-16 |
EP0712389A1 (en) | 1996-05-22 |
FI960504A0 (fi) | 1996-02-02 |
DE69426629D1 (de) | 2001-03-01 |
NZ269773A (en) | 1997-11-24 |
CA2167818A1 (en) | 1995-02-09 |
NO960389L (no) | 1996-01-30 |
EP0712389A4 (en) | 1997-04-09 |
ATE198880T1 (de) | 2001-02-15 |
FI960504A (fi) | 1996-02-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO313227B1 (no) | Terapeutisk forbindelse - fettsyrekonjugater | |
US5221752A (en) | α-keto amide derivatives | |
KR900008004B1 (ko) | 펩티다제 억제물의 제조방법 | |
JPS6256458A (ja) | 新規なアミノ酸誘導体 | |
JPS61236770A (ja) | 新規なアミノ酸誘導体 | |
LT3953B (en) | Oxalylamino acids derivatives, process for the preparation and use thereof | |
US4333879A (en) | Epoxysuccinic acid derivatives | |
US4970297A (en) | Transglutaminase inhibitors | |
Kempf et al. | Renin inhibitors based on novel dipeptide analogs. Incorporation of the dehydrohydroxyethylene isostere at the scissile bond | |
Esteves et al. | Synthesis and characterization of novel fluorescent N-glycoconjugates | |
JPH0680077B2 (ja) | プロリンエンドペプチダ−ゼインヒビタ−活性を有する新規ペプチド化合物 | |
JP4784725B2 (ja) | メイラード反応阻害剤 | |
Harada et al. | A practical synthesis of the [(2R)-3-(morpholinocarbonyl)-2-(1-naphthylmethyl) propionyl]-L-histidine moiety (P4-P2) in renin inhibitors | |
EP0333000A2 (en) | Peptides with inhibitory activity of enzymatic systems, process for their preparation and pharmaceutical compositions containing them | |
AU683289B2 (en) | Therapeutic compound - fatty acid conjugates | |
Abdel-Monem et al. | Polyamine Metabolism I: Synthesislof Dansyl Derivatives of N-(Monoaminoalkyl)-and N-(Polyaminoalkyl) acetamides and Elucidation in Urine of a Cancer Patient | |
Zlatoidsky et al. | Synthesis and structure-activity relationship study of the new set of trypsin-like proteinase inhibitors | |
US3891692A (en) | N-(cyclopropylalkoxycarbonyl)amino acids | |
JPH11228526A (ja) | ペプチド誘導体及びその薬学的に許容される塩、その製造方法及びその用途 | |
Himaja et al. | Synthesis and biological evaluation of Pseudostellarin D | |
Freskos et al. | Synthesis of succinate containing dipeptide isosteres via carbonylation of enol triflates. | |
US6063919A (en) | Process for the synthesis of exochelins | |
JPH0745501B2 (ja) | 新規環状ジペプチド化合物 | |
JORGENSEN et al. | Thyroxine Analogs. IV. 1 Synthesis of Aliphatic and Alicyclic Ethers of 3, 5-Diiodo-DL-tyrosine2 | |
Kovacs et al. | Racemization mechanism of cysteine dipeptide active ester derivatives |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |