NO964514L - Angiogeneseinhibitor - Google Patents

Angiogeneseinhibitor

Info

Publication number: NO964514L
Authority: NO; Norway
Prior art keywords: compound; angiogenesis inhibitor; optionally substituted; inhibitor according; carbonyl
Prior art date: 1995-10-25

Application number

NO964514A

Other languages

English (en)

Norwegian (no)

Other versions

NO964514D0 (no

Inventor

Chiho Fukiage

Mitsuyoshi Azuma

Jun Inoue

Masayuki Nakamura

Yuka Yoshida

Original Assignee

Senju Pharma Co

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.)

1995-10-25

Filing date

1996-10-24

Publication date

1997-04-28

1996-10-24 Application filed by Senju Pharma Co filed Critical Senju Pharma Co

1996-10-24 Publication of NO964514D0 publication Critical patent/NO964514D0/no

1997-04-28 Publication of NO964514L publication Critical patent/NO964514L/no

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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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
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
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OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
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YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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ALGYZDJCQFKVJF-UHFFFAOYSA-N tert-butyl n-[1-[4-(4-chlorophenyl)piperazin-1-yl]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound C1CN(C(=O)C(NC(=O)OC(C)(C)C)CC(C)C)CCN1C1=CC=C(Cl)C=C1 ALGYZDJCQFKVJF-UHFFFAOYSA-N 0.000 description 1
IUZVMYNNUGHDPN-UHFFFAOYSA-N tert-butyl n-[1-[4-(dimethylsulfamoyl)piperazin-1-yl]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(CC(C)C)C(=O)N1CCN(S(=O)(=O)N(C)C)CC1 IUZVMYNNUGHDPN-UHFFFAOYSA-N 0.000 description 1
SHYHFWWIJKDCBR-UHFFFAOYSA-N tert-butyl n-[4-methyl-1-[4-(4-methylphenyl)sulfonylpiperazin-1-yl]-1-oxopentan-2-yl]carbamate Chemical compound C1CN(C(=O)C(NC(=O)OC(C)(C)C)CC(C)C)CCN1S(=O)(=O)C1=CC=C(C)C=C1 SHYHFWWIJKDCBR-UHFFFAOYSA-N 0.000 description 1
OLDVXYSSEXJKPS-UHFFFAOYSA-N tert-butyl n-[4-methyl-1-oxo-1-(4-phenylpiperazin-1-yl)pentan-2-yl]carbamate Chemical compound C1CN(C(=O)C(NC(=O)OC(C)(C)C)CC(C)C)CCN1C1=CC=CC=C1 OLDVXYSSEXJKPS-UHFFFAOYSA-N 0.000 description 1
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YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
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QYEFBJRXKKSABU-UHFFFAOYSA-N xylazine hydrochloride Chemical compound Cl.CC1=CC=CC(C)=C1NC1=NCCCS1 QYEFBJRXKKSABU-UHFFFAOYSA-N 0.000 description 1
229960004175 xylazine hydrochloride Drugs 0.000 description 1

Classifications

- 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)
Proteomics, Peptides & Aminoacids (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Gastroenterology & Hepatology (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (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)

NO964514A 1995-10-25 1996-10-24 Angiogeneseinhibitor NO964514L (no)

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
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 (de)
EP (2)	EP0927716B1 (de)
AR (1)	AR004694A1 (de)
AT (3)	ATE230275T1 (de)
AU (1)	AU716495B2 (de)
BR (1)	BR9605267A (de)
CA (1)	CA2188817C (de)
DE (3)	DE69628050T2 (de)
ES (2)	ES2190139T3 (de)
HU (1)	HUP9602943A3 (de)
MX (1)	MX9605156A (de)
NO (1)	NO964514L (de)
PL (1)	PL316669A1 (de)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2226740A1 (en) *	1995-07-13	1997-01-30	Mitsuyoshi Azuma	Piperazine derivative and its uses
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
BR9908566A (pt) *	1998-03-05	2000-11-21	Senju Pharma Co	Composição farmacêutica para profilaxia e terapia de doenças associadas a citopatia do tecido do fundo ocular
US6342531B1 (en) *	1998-03-20	2002-01-29	Senju Pharmaceutical Co., Ltd.	Pharmaceutical composition containing a cysteine protease inhibitor for prophylaxis and therapy of brain tissue impairment
GB9819860D0 (en) *	1998-09-12	1998-11-04	Zeneca Ltd	Chemical compounds
CA2356929A1 (en)	1998-12-23	2000-07-06	G.D. Searle & Co.	Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combonation therapy in the treatment of neoplasia
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1996
- 1996-10-23 ES ES99102501T patent/ES2190139T3/es not_active Expired - Lifetime
- 1996-10-23 AT AT96116994T patent/ATE230275T1/de not_active IP Right Cessation
- 1996-10-23 AT AT99102501T patent/ATE230389T1/de not_active IP Right Cessation
- 1996-10-23 EP EP99106760A patent/EP0927716B1/de not_active Expired - Lifetime
- 1996-10-23 ES ES99106760T patent/ES2193615T3/es not_active Expired - Lifetime
- 1996-10-23 AT AT99106760T patent/ATE239698T1/de not_active IP Right Cessation
- 1996-10-23 DE DE69628050T patent/DE69628050T2/de not_active Expired - Lifetime
- 1996-10-23 DE DE69625622T patent/DE69625622T2/de not_active Expired - Lifetime
- 1996-10-23 DE DE69625575T patent/DE69625575T2/de not_active Expired - Lifetime
- 1996-10-23 EP EP96116994A patent/EP0771565B1/de not_active Expired - Lifetime
- 1996-10-24 AU AU70384/96A patent/AU716495B2/en not_active Ceased
- 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 NO NO964514A patent/NO964514L/no not_active Application Discontinuation
- 1996-10-24 PL PL96316669A patent/PL316669A1/xx unknown
- 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
DE69625575T2 (de)	2003-09-25
EP0771565B1 (de)	2003-01-02
PL316669A1 (en)	1997-04-28
EP0927716A1 (de)	1999-07-07
CA2188817A1 (en)	1997-04-26
EP0771565A3 (de)	1998-11-04
AU716495B2 (en)	2000-02-24
ATE230389T1 (de)	2003-01-15
EP0771565A2 (de)	1997-05-07
US6551999B1 (en)	2003-04-22
DE69625622T2 (de)	2003-08-14
DE69625575D1 (de)	2003-02-06
AU7038496A (en)	1997-05-01
NO964514D0 (no)	1996-10-24
ATE230275T1 (de)	2003-01-15
US6057290A (en)	2000-05-02
BR9605267A (pt)	1998-07-21
DE69628050D1 (de)	2003-06-12
HUP9602943A2 (en)	1997-08-28
ES2193615T3 (es)	2003-11-01
DE69625622D1 (de)	2003-02-06
ATE239698T1 (de)	2003-05-15
AR004694A1 (es)	1999-03-10
MX9605156A (es)	1998-05-31
HUP9602943A3 (en)	1998-03-02
CA2188817C (en)	2010-01-26
EP0927716B1 (de)	2003-05-07
DE69628050T2 (de)	2004-04-01
ES2190139T3 (es)	2003-07-16

Legal Events

Date	Code	Title	Description
2003-04-07	FC2A	Withdrawal, rejection or dismissal of laid open patent application

Publication	Publication Date	Title
EP0771565B1 (de)	2003-01-02	Angiogense-Inhibitor
AU714324B2 (en)	2000-01-06	D-amino acid derived inhibitors of cysteine and serine proteases
EP0337714A2 (de)	1989-10-18	HIV-Protease-Inhibitoren zur Behandlung von AIDS
JPH0859610A (ja)	1996-03-05	ファルネシル蛋白質トランスフェラーゼの抑制剤
CS107990A2 (en)	1991-08-13	Method of aminoacids' new derivatives production
US6608100B1 (en)	2003-08-19	HIV protease inhibitors based on amino acid derivatives
US5935959A (en)	1999-08-10	Piperazine derivatives and use as cysteine inhibitors
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US6214800B1 (en)	2001-04-10	Angiogenesis inhibitor
AU753986B2 (en)	2002-10-31	Angiogenesis inhibitor
KR100472914B1 (ko)	2005-11-16	혈관형성억제제
EP0928786A1 (de)	1999-07-14	Angiogenese Inhibitoren
KR20010034168A (ko)	2001-04-25	매트릭스 메탈로프로테이나제 억제제
JP3185700B2 (ja)	2001-07-11	ペプチジルアルデヒド誘導体およびその用途
JP3999939B2 (ja)	2007-10-31	ぺプチジルアルデヒド誘導体およびその用途
JPWO1997003060A1 (ja)	1998-08-25	ピペラジン誘導体およびその用途
US20040209822A1 (en)	2004-10-21	Novel compounds