NO964514L - Angiogeneseinhibitor - Google Patents
AngiogeneseinhibitorInfo
- Publication number
- NO964514L NO964514L NO964514A NO964514A NO964514L NO 964514 L NO964514 L NO 964514L NO 964514 A NO964514 A NO 964514A NO 964514 A NO964514 A NO 964514A NO 964514 L NO964514 L NO 964514L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- angiogenesis inhibitor
- optionally substituted
- inhibitor according
- carbonyl
- Prior art date
Links
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 title claims description 58
- 239000004037 angiogenesis inhibitor Substances 0.000 title claims description 58
- 229940121369 angiogenesis inhibitor Drugs 0.000 title claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 124
- 125000003118 aryl group Chemical group 0.000 claims description 94
- -1 aldehyde compounds Chemical class 0.000 claims description 84
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 62
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 230000002401 inhibitory effect Effects 0.000 claims description 34
- 102000005927 Cysteine Proteases Human genes 0.000 claims description 27
- 108010005843 Cysteine Proteases Proteins 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 102100035037 Calpastatin Human genes 0.000 claims description 18
- 108010044208 calpastatin Proteins 0.000 claims description 18
- ZXJCOYBPXOBJMU-HSQGJUDPSA-N calpastatin peptide Ac 184-210 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CCSC)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(O)=O)NC(C)=O)[C@@H](C)O)C1=CC=C(O)C=C1 ZXJCOYBPXOBJMU-HSQGJUDPSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 108010032088 Calpain Proteins 0.000 claims description 15
- 102000007590 Calpain Human genes 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- DCEMCPAKSGRHCN-UHFFFAOYSA-N oxirane-2,3-dicarboxylic acid Chemical compound OC(=O)C1OC1C(O)=O DCEMCPAKSGRHCN-UHFFFAOYSA-N 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- 150000001413 amino acids Chemical group 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 claims description 9
- GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 claims description 9
- 108010052968 leupeptin Proteins 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000003857 carboxamides Chemical class 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 102000000584 Calmodulin Human genes 0.000 claims description 6
- 108010041952 Calmodulin Proteins 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000000101 thioether group Chemical group 0.000 claims description 4
- 150000003568 thioethers Chemical class 0.000 claims description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000004797 ketoamides Chemical class 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 125000003151 isocoumarinyl group Chemical class C1(=O)OC(=CC2=CC=CC=C12)* 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 188
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 154
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 95
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 78
- 238000000034 method Methods 0.000 description 75
- 239000013078 crystal Substances 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 63
- 235000002639 sodium chloride Nutrition 0.000 description 57
- 239000000203 mixture Substances 0.000 description 53
- 239000004593 Epoxy Substances 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- 239000008188 pellet Substances 0.000 description 44
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000002253 acid Substances 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 25
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 25
- 229960004295 valine Drugs 0.000 description 25
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 210000004087 cornea Anatomy 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 235000017557 sodium bicarbonate Nutrition 0.000 description 20
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
- 229910052799 carbon Inorganic materials 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- IHXVJRCMRFOIAM-UHFFFAOYSA-N 2-amino-1-[4-(4-fluorophenyl)piperazin-1-yl]-3-phenylpropan-1-one;hydrochloride Chemical compound Cl.C1CN(C=2C=CC(F)=CC=2)CCN1C(=O)C(N)CC1=CC=CC=C1 IHXVJRCMRFOIAM-UHFFFAOYSA-N 0.000 description 17
- 238000001816 cooling Methods 0.000 description 17
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 15
- 238000002054 transplantation Methods 0.000 description 15
- 239000004474 valine Substances 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 14
- 230000033115 angiogenesis Effects 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000011259 mixed solution Substances 0.000 description 12
- 239000012230 colorless oil Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 238000006735 epoxidation reaction Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- DZQVAQAZQDURKX-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine;dihydrochloride Chemical compound [Cl-].[Cl-].C1=CC(F)=CC=C1[NH+]1CC[NH2+]CC1 DZQVAQAZQDURKX-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 210000002889 endothelial cell Anatomy 0.000 description 9
- FKWIHZLJWZCQFV-UHFFFAOYSA-N tert-butyl n-[1-[4-(4-fluorophenyl)piperazin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound C1CN(C=2C=CC(F)=CC=2)CCN1C(=O)C(NC(=O)OC(C)(C)C)CC1=CC=CC=C1 FKWIHZLJWZCQFV-UHFFFAOYSA-N 0.000 description 9
- NPDBDJFLKKQMCM-UHFFFAOYSA-N tert-butylglycine Chemical compound CC(C)(C)C(N)C(O)=O NPDBDJFLKKQMCM-UHFFFAOYSA-N 0.000 description 9
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 8
- 239000004365 Protease Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 210000004204 blood vessel Anatomy 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000008213 purified water Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 7
- 108090000624 Cathepsin L Proteins 0.000 description 7
- 102000004172 Cathepsin L Human genes 0.000 description 7
- 241000700199 Cavia porcellus Species 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 229940024606 amino acid Drugs 0.000 description 7
- 235000001014 amino acid Nutrition 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 102000009027 Albumins Human genes 0.000 description 6
- 108010088751 Albumins Proteins 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 101000749287 Clitocybe nebularis Clitocypin Proteins 0.000 description 6
- 101000767029 Clitocybe nebularis Clitocypin-1 Proteins 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 229940094664 Cysteine protease inhibitor Drugs 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- 239000003889 eye drop Substances 0.000 description 6
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
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- 108090000526 Papain Proteins 0.000 description 5
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- 150000002148 esters Chemical class 0.000 description 5
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
- 150000007529 inorganic bases Chemical class 0.000 description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
- 239000012588 trypsin Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 241000700198 Cavia Species 0.000 description 4
- KZSNJWFQEVHDMF-SCSAIBSYSA-N D-valine Chemical compound CC(C)[C@@H](N)C(O)=O KZSNJWFQEVHDMF-SCSAIBSYSA-N 0.000 description 4
- 229930182831 D-valine Natural products 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 238000002513 implantation Methods 0.000 description 4
- 150000002512 isocoumarins Chemical class 0.000 description 4
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27748595 | 1995-10-25 | ||
JP24804696 | 1996-09-19 |
Publications (2)
Publication Number | Publication Date |
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NO964514D0 NO964514D0 (no) | 1996-10-24 |
NO964514L true NO964514L (no) | 1997-04-28 |
Family
ID=26538555
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO964514A NO964514L (no) | 1995-10-25 | 1996-10-24 | Angiogeneseinhibitor |
Country Status (13)
Country | Link |
---|---|
US (2) | US6057290A (es) |
EP (2) | EP0927716B1 (es) |
AR (1) | AR004694A1 (es) |
AT (3) | ATE230275T1 (es) |
AU (1) | AU716495B2 (es) |
BR (1) | BR9605267A (es) |
CA (1) | CA2188817C (es) |
DE (3) | DE69625622T2 (es) |
ES (2) | ES2193615T3 (es) |
HU (1) | HUP9602943A3 (es) |
MX (1) | MX9605156A (es) |
NO (1) | NO964514L (es) |
PL (1) | PL316669A1 (es) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1195343A (zh) * | 1995-07-13 | 1998-10-07 | 千寿制药株式会社 | 哌啶衍生物及其用途 |
US6214800B1 (en) * | 1995-10-25 | 2001-04-10 | Senju Pharmaceutical Co., Ltd. | Angiogenesis inhibitor |
DE19718826A1 (de) * | 1997-05-05 | 1998-11-12 | Marion S Dr Eckmiller | Verwendung biologisch aktiver Wirkstoffe zum Beeinflussen des Extrazellulär-Raumes von Sinneszellen und Verfahren zur Wirkstoff-Administrationssteuerung |
JP4336039B2 (ja) * | 1997-09-04 | 2009-09-30 | 日本ケミファ株式会社 | エポキシコハク酸アミド誘導体 |
US6015787A (en) * | 1997-11-04 | 2000-01-18 | New England Medical Center Hospitals, Inc. | Cell-permeable protein inhibitors of calpain |
DE69939075D1 (de) * | 1998-03-05 | 2008-08-21 | Senju Pharma Co | Pharmazeutische Zusammenstellung zur Vorbeugung und Behandlung von mit Zellkrankheiten des Augenhintergrundes zusammenhängenden Krankheiten |
KR20010041967A (ko) * | 1998-03-20 | 2001-05-25 | 요시다 쇼지 | 뇌조직 장애를 예방 및 치료하기 위한 시스테인프로테아제 억제제 함유 약제학적 조성물 |
GB9819860D0 (en) * | 1998-09-12 | 1998-11-04 | Zeneca Ltd | Chemical compounds |
WO2000038730A2 (en) | 1998-12-23 | 2000-07-06 | G.D. Searle & Co. | Use of a cyclooxygenase-2 inhibitor and one or more antineoplastic agents for combination therapy in neoplasia |
AU3196300A (en) * | 1999-03-26 | 2000-10-16 | Shionogi & Co., Ltd. | Carbocyclic sulfonamide derivatives |
KR20010001270A (ko) * | 1999-06-03 | 2001-01-05 | 복성해 | 혈관신생을 억제하는 새로운 이소쿠마린 유도체 |
WO2001026648A1 (fr) | 1999-10-13 | 2001-04-19 | Senju Pharmaceutical Co., Ltd. | Preparation d'adhesif a usage ophtalmique pour l'absorption par voie percutanee |
WO2001041757A1 (fr) * | 1999-12-10 | 2001-06-14 | Senju Pharmaceutical Co., Ltd. | Composition pharmaceutique contenant de la cyclodextrine |
US7572833B2 (en) * | 2000-10-26 | 2009-08-11 | Senju Pharmaceutical Co., Ltd. | Drug composition comprising dipeptidyl aldehyde derivative |
WO2002048096A1 (fr) * | 2000-12-12 | 2002-06-20 | Senju Pharmaceutical Co., Ltd. | Derives d'hydrazone et utilisation de ceux-ci dans des medicaments |
MXPA03011197A (es) * | 2001-06-06 | 2004-02-26 | Lilly Co Eli | Benzoilsufonamidas y sulfonilbenzamidinas que se usan como agentes antitumorales. |
US7115607B2 (en) * | 2001-07-25 | 2006-10-03 | Amgen Inc. | Substituted piperazinyl amides and methods of use |
WO2003078415A1 (fr) * | 2002-03-15 | 2003-09-25 | Senju Pharmaceutical Co., Ltd. | Derive de l'hemiacetal cyclique et son utilisation |
ES2348534T3 (es) * | 2002-03-29 | 2010-12-09 | Senju Pharmaceutical Co., Ltd. | Derivador de hidroximordolinona y uso medicinal del mismo. |
EP1354586A1 (en) * | 2002-04-20 | 2003-10-22 | Aventis Pharma Deutschland GmbH | The use of hydroxpyridone-derivatives in wound healing |
DE60330038D1 (de) * | 2002-07-22 | 2009-12-24 | Senju Pharma Co | Neue alpha-ketoamidderivate und deren verwendung |
GB0314262D0 (en) | 2003-06-19 | 2003-07-23 | Univ Nottingham Trent | Novel compounds and methods of using the same |
US7615556B2 (en) | 2006-01-27 | 2009-11-10 | Bristol-Myers Squibb Company | Piperazinyl derivatives as modulators of chemokine receptor activity |
US8236798B2 (en) | 2009-05-07 | 2012-08-07 | Abbott Gmbh & Co. Kg | Carboxamide compounds and their use as calpain inhibitors |
US20120065793A1 (en) | 2010-02-25 | 2012-03-15 | Kaji Mitsuru | Demand and supply control apparatus, demand and supply control method, and program |
JP5823484B2 (ja) | 2010-07-14 | 2015-11-25 | 千寿製薬株式会社 | α―ケトアミド誘導体固体分散体 |
GB201218084D0 (en) * | 2012-10-09 | 2012-11-21 | Univ Aston | Novel compounds and methods for use in medicine |
GB201220474D0 (en) * | 2012-11-14 | 2012-12-26 | Sagetis Biotech Sl | Polypeptides |
US20210145930A1 (en) * | 2018-05-07 | 2021-05-20 | NeuroTheranostics, Inc. | Multiple layer article with interactive reinforcements linear ribbon fiber reinforcement for composite forms |
US20240150396A1 (en) * | 2021-03-03 | 2024-05-09 | The Texas A&M University System | Inhibitors of cysteine proteases |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50137951A (es) | 1974-04-27 | 1975-11-01 | ||
JPS5754157A (en) | 1980-09-19 | 1982-03-31 | Nippon Kayaku Co Ltd | L-argininal derivative and its preparation |
PT84170B (pt) * | 1986-01-24 | 1989-03-30 | Sanofi Sa | Processo para a preparacao de derivados n alfa-substituidos das n alfa-aril-sulfonilaminoacil d-amidinofenil-alaninamidas |
JP2536754B2 (ja) * | 1987-05-08 | 1996-09-18 | 日本ケミファ株式会社 | ピペラジン誘導体 |
JPH0832698B2 (ja) * | 1987-05-08 | 1996-03-29 | 日本ケミファ株式会社 | ピペラジン誘導体 |
US5510531A (en) | 1989-04-10 | 1996-04-23 | Suntory Limited | Proteinase inhibitor |
JP2701932B2 (ja) | 1989-04-10 | 1998-01-21 | サントリー株式会社 | タンパク質分解酵素阻害剤 |
EP0395309B1 (en) * | 1989-04-28 | 1995-12-27 | Takara Shuzo Co. Ltd. | Human calpastatin-like polypeptide |
ZA921279B (en) | 1991-02-22 | 1993-08-23 | Du Pont Merck Pharma | Substituted alpha-aminoaldehydes and derivatives |
EP0504938A3 (en) * | 1991-03-22 | 1993-04-14 | Suntory Limited | Prophylactic and therapeutic agent for bone diseases comprising di- or tripeptide derivative as active ingredient |
CA2071621C (en) * | 1991-06-19 | 1996-08-06 | Ahihiko Hosoda | Aldehyde derivatives |
JP2848232B2 (ja) | 1993-02-19 | 1999-01-20 | 武田薬品工業株式会社 | アルデヒド誘導体 |
US5607831A (en) | 1993-03-25 | 1997-03-04 | The United States Of America As Represented By The Department Of Health And Human Services | In vitro methods for assessing the susceptibility of HIV-1-infected individuals to cysteine protease-mediated activation-induced programmed cell death |
US5658885A (en) | 1993-04-27 | 1997-08-19 | The Dupont Merck Pharmaceutical Company | Amidino and guanidino substituted boronic acid inhibitors of trypsin-like enzymes |
JP3599287B2 (ja) * | 1993-04-28 | 2004-12-08 | 三菱化学株式会社 | スルホンアミド誘導体 |
WO1996010014A1 (en) * | 1994-09-27 | 1996-04-04 | Takeda Chemical Industries, Ltd. | Aldehyde derivatives as upsteine protease inhibitors |
US5614649A (en) | 1994-11-14 | 1997-03-25 | Cephalon, Inc. | Multicatalytic protease inhibitors |
EP0731107A1 (en) * | 1995-02-13 | 1996-09-11 | Takeda Chemical Industries, Ltd. | Production of aldehyde derivatives |
CA2217850A1 (en) | 1995-05-10 | 1996-11-14 | Chirotech Technology Limited | Peptide compounds which inhibit metalloproteinase and tnf liberation, and their therapeutic use |
CN1195343A (zh) * | 1995-07-13 | 1998-10-07 | 千寿制药株式会社 | 哌啶衍生物及其用途 |
ATE377006T1 (de) | 1995-11-28 | 2007-11-15 | Cephalon Inc | Aus d-aminosäuren abgeleitete cystein- und serinproteasehemmer |
-
1996
- 1996-10-23 ES ES99106760T patent/ES2193615T3/es not_active Expired - Lifetime
- 1996-10-23 DE DE69625622T patent/DE69625622T2/de not_active Expired - Lifetime
- 1996-10-23 ES ES99102501T patent/ES2190139T3/es not_active Expired - Lifetime
- 1996-10-23 EP EP99106760A patent/EP0927716B1/en not_active Expired - Lifetime
- 1996-10-23 AT AT96116994T patent/ATE230275T1/de not_active IP Right Cessation
- 1996-10-23 AT AT99106760T patent/ATE239698T1/de not_active IP Right Cessation
- 1996-10-23 DE DE69625575T patent/DE69625575T2/de not_active Expired - Lifetime
- 1996-10-23 DE DE69628050T patent/DE69628050T2/de not_active Expired - Lifetime
- 1996-10-23 EP EP96116994A patent/EP0771565B1/en not_active Expired - Lifetime
- 1996-10-23 AT AT99102501T patent/ATE230389T1/de not_active IP Right Cessation
- 1996-10-24 MX MX9605156A patent/MX9605156A/es unknown
- 1996-10-24 US US08/740,069 patent/US6057290A/en not_active Expired - Lifetime
- 1996-10-24 CA CA2188817A patent/CA2188817C/en not_active Expired - Fee Related
- 1996-10-24 PL PL96316669A patent/PL316669A1/xx unknown
- 1996-10-24 NO NO964514A patent/NO964514L/no not_active Application Discontinuation
- 1996-10-24 AU AU70384/96A patent/AU716495B2/en not_active Ceased
- 1996-10-24 HU HU9602943A patent/HUP9602943A3/hu unknown
- 1996-10-25 BR BR9605267A patent/BR9605267A/pt not_active Application Discontinuation
- 1996-10-25 AR ARP960104906A patent/AR004694A1/es unknown
-
1999
- 1999-02-03 US US09/243,822 patent/US6551999B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ES2190139T3 (es) | 2003-07-16 |
CA2188817A1 (en) | 1997-04-26 |
DE69628050T2 (de) | 2004-04-01 |
NO964514D0 (no) | 1996-10-24 |
AU7038496A (en) | 1997-05-01 |
DE69625575D1 (de) | 2003-02-06 |
ATE230275T1 (de) | 2003-01-15 |
DE69625622D1 (de) | 2003-02-06 |
ATE239698T1 (de) | 2003-05-15 |
DE69625575T2 (de) | 2003-09-25 |
EP0771565B1 (en) | 2003-01-02 |
EP0927716A1 (en) | 1999-07-07 |
DE69625622T2 (de) | 2003-08-14 |
ES2193615T3 (es) | 2003-11-01 |
EP0771565A3 (en) | 1998-11-04 |
EP0771565A2 (en) | 1997-05-07 |
DE69628050D1 (de) | 2003-06-12 |
US6551999B1 (en) | 2003-04-22 |
BR9605267A (pt) | 1998-07-21 |
CA2188817C (en) | 2010-01-26 |
HUP9602943A2 (en) | 1997-08-28 |
HUP9602943A3 (en) | 1998-03-02 |
AU716495B2 (en) | 2000-02-24 |
ATE230389T1 (de) | 2003-01-15 |
AR004694A1 (es) | 1999-03-10 |
EP0927716B1 (en) | 2003-05-07 |
MX9605156A (es) | 1998-05-31 |
PL316669A1 (en) | 1997-04-28 |
US6057290A (en) | 2000-05-02 |
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