JP2002502852A5 - - Google Patents

Info

Publication number

JP2002502852A5

JP2002502852A5 JP2000530517A JP2000530517A JP2002502852A5 JP 2002502852 A5 JP2002502852 A5 JP 2002502852A5 JP 2000530517 A JP2000530517 A JP 2000530517A JP 2000530517 A JP2000530517 A JP 2000530517A JP 2002502852 A5 JP2002502852 A5 JP 2002502852A5

Authority

JP

Japan

Prior art keywords

thiazol

methylthiothiophene

carboxamidine

acid

alkyl

Prior art date

1999-02-09

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

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• -1 amino, hydroxy Chemical group 0.000 description 193
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 134
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 102
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 94
• 150000001875 compounds Chemical class 0.000 description 94
• 125000000217 alkyl group Chemical group 0.000 description 68
• 239000002253 acid Substances 0.000 description 54
• 239000002904 solvent Substances 0.000 description 53
• 239000000243 solution Substances 0.000 description 52
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 47
• 150000001409 amidines Chemical class 0.000 description 46
• 239000000377 silicon dioxide Substances 0.000 description 46
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• 239000000460 chlorine Substances 0.000 description 44
• 238000006243 chemical reaction Methods 0.000 description 43
• 229910052739 hydrogen Inorganic materials 0.000 description 43
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
• 230000015572 biosynthetic process Effects 0.000 description 41
• 239000001257 hydrogen Substances 0.000 description 41
• 125000003545 alkoxy group Chemical group 0.000 description 39
• 238000000034 method Methods 0.000 description 37
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
• 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 33
• 125000003118 aryl group Chemical group 0.000 description 33
• 238000003786 synthesis reaction Methods 0.000 description 33
• 125000004093 cyano group Chemical group *C#N 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• 150000001412 amines Chemical class 0.000 description 28
• 239000003153 chemical reaction reagent Substances 0.000 description 27
• 239000000203 mixture Substances 0.000 description 27
• 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 26
• 229910052736 halogen Inorganic materials 0.000 description 26
• 150000002367 halogens Chemical class 0.000 description 26
• 229960005356 urokinase Drugs 0.000 description 26
• 239000002585 base Substances 0.000 description 25
• 229910052757 nitrogen Inorganic materials 0.000 description 24
• 238000005160 1H NMR spectroscopy Methods 0.000 description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• 235000019270 ammonium chloride Nutrition 0.000 description 23
• 239000007787 solid Substances 0.000 description 23
• 150000002148 esters Chemical class 0.000 description 22
• 150000002431 hydrogen Chemical class 0.000 description 22
• 238000001819 mass spectrum Methods 0.000 description 22
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 22
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
• 239000011541 reaction mixture Substances 0.000 description 19
• 150000001408 amides Chemical class 0.000 description 18
• 210000004027 cell Anatomy 0.000 description 18
• 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 18
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
• 125000004414 alkyl thio group Chemical group 0.000 description 17
• 125000005110 aryl thio group Chemical group 0.000 description 17
• 125000004104 aryloxy group Chemical group 0.000 description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
• 239000002002 slurry Substances 0.000 description 17
• NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 16
• AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical compound OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 16
• 239000011521 glass Substances 0.000 description 16
• 125000000623 heterocyclic group Chemical group 0.000 description 16
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 16
• 239000011159 matrix material Substances 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• 108010088842 Fibrinolysin Proteins 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 229940012957 plasmin Drugs 0.000 description 15
• 150000003839 salts Chemical class 0.000 description 15
• 229910052717 sulfur Inorganic materials 0.000 description 15
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
• 125000004442 acylamino group Chemical group 0.000 description 14
• 125000000266 alpha-aminoacyl group Chemical group 0.000 description 14
• 125000004663 dialkyl amino group Chemical group 0.000 description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 14
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• 108091005804 Peptidases Proteins 0.000 description 13
• 102000035195 Peptidases Human genes 0.000 description 13
• 239000012043 crude product Substances 0.000 description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
• 238000010992 reflux Methods 0.000 description 13
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
• 206010028980 Neoplasm Diseases 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 12
• 125000001424 substituent group Chemical group 0.000 description 12
• 239000004365 Protease Substances 0.000 description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 11
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 11
• 230000008878 coupling Effects 0.000 description 11
• 238000010168 coupling process Methods 0.000 description 11
• 238000005859 coupling reaction Methods 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• 125000000335 thiazolyl group Chemical group 0.000 description 11
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 10
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 10
• 125000003710 aryl alkyl group Chemical group 0.000 description 10
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
• 229910052760 oxygen Inorganic materials 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• 239000011593 sulfur Chemical group 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 206010027476 Metastases Diseases 0.000 description 9
• 108090000190 Thrombin Proteins 0.000 description 9
• 125000005140 aralkylsulfonyl group Chemical group 0.000 description 9
• 125000004659 aryl alkyl thio group Chemical group 0.000 description 9
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 9
• 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 150000002576 ketones Chemical class 0.000 description 9
• 230000009401 metastasis Effects 0.000 description 9
• 229910052763 palladium Inorganic materials 0.000 description 9
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 8
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 8
• 239000002841 Lewis acid Substances 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• 206010060862 Prostate cancer Diseases 0.000 description 8
• 208000004403 Prostatic Hyperplasia Diseases 0.000 description 8
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 8
• 201000004681 Psoriasis Diseases 0.000 description 8
• 235000011054 acetic acid Nutrition 0.000 description 8
• 125000003282 alkyl amino group Chemical group 0.000 description 8
• 229910021529 ammonia Inorganic materials 0.000 description 8
• 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 8
• 125000004181 carboxyalkyl group Chemical group 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 238000010438 heat treatment Methods 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• 150000007517 lewis acids Chemical class 0.000 description 8
• 125000002971 oxazolyl group Chemical group 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 230000017854 proteolysis Effects 0.000 description 8
• 239000012453 solvate Substances 0.000 description 8
• 108010074860 Factor Xa Proteins 0.000 description 7
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 7
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
• 102100031358 Urokinase-type plasminogen activator Human genes 0.000 description 7
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 7
• 239000003638 chemical reducing agent Substances 0.000 description 7
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 7
• 239000007789 gas Substances 0.000 description 7
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 7
• 239000008194 pharmaceutical composition Substances 0.000 description 7
• 125000001544 thienyl group Chemical group 0.000 description 7
• 229960004072 thrombin Drugs 0.000 description 7
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 6
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 6
• 108090000631 Trypsin Proteins 0.000 description 6
• 102000004142 Trypsin Human genes 0.000 description 6
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 6
• 230000029936 alkylation Effects 0.000 description 6
• 238000005804 alkylation reaction Methods 0.000 description 6
• 239000012131 assay buffer Substances 0.000 description 6
• 210000002469 basement membrane Anatomy 0.000 description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
• 230000003197 catalytic effect Effects 0.000 description 6
• 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 description 6
• 210000002744 extracellular matrix Anatomy 0.000 description 6
• 125000001072 heteroaryl group Chemical group 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 125000002883 imidazolyl group Chemical group 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 125000004076 pyridyl group Chemical group 0.000 description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
• 239000012588 trypsin Substances 0.000 description 6
• 229960001322 trypsin Drugs 0.000 description 6
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
• FZRKAZHKEDOPNN-UHFFFAOYSA-N Nitric oxide anion Chemical compound O=[N-] FZRKAZHKEDOPNN-UHFFFAOYSA-N 0.000 description 5
• 239000004793 Polystyrene Substances 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• 239000002168 alkylating agent Substances 0.000 description 5
• 229940100198 alkylating agent Drugs 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• 201000011510 cancer Diseases 0.000 description 5
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
• DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 5
• XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• 229940088598 enzyme Drugs 0.000 description 5
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 5
• 239000001301 oxygen Substances 0.000 description 5
• 239000002797 plasminogen activator inhibitor Substances 0.000 description 5
• 229920002223 polystyrene Polymers 0.000 description 5
• 208000037803 restenosis Diseases 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 125000000547 substituted alkyl group Chemical group 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
• 108090000317 Chymotrypsin Proteins 0.000 description 4
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
• 102000013566 Plasminogen Human genes 0.000 description 4
• 108010051456 Plasminogen Proteins 0.000 description 4
• 125000002252 acyl group Chemical group 0.000 description 4
• 229910052782 aluminium Inorganic materials 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 4
• 230000033115 angiogenesis Effects 0.000 description 4
• 150000001450 anions Chemical class 0.000 description 4
• 230000003110 anti-inflammatory effect Effects 0.000 description 4
• 230000003262 anti-osteoporosis Effects 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
• 229960002376 chymotrypsin Drugs 0.000 description 4
• 125000000753 cycloalkyl group Chemical group 0.000 description 4
• 230000001419 dependent effect Effects 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 125000002541 furyl group Chemical group 0.000 description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
• 230000002401 inhibitory effect Effects 0.000 description 4
• 125000005647 linker group Chemical group 0.000 description 4
• 150000004702 methyl esters Chemical class 0.000 description 4
• 150000002825 nitriles Chemical class 0.000 description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• 239000011347 resin Substances 0.000 description 4
• 229920005989 resin Polymers 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 4
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 4
• 150000003573 thiols Chemical class 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• 210000001519 tissue Anatomy 0.000 description 4
• KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 description 4
• LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 3
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 3
• OMMIMDGHTTXEFT-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-5-methylsulfanylthiophene-2-carboximidamide Chemical compound S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C=CC(Cl)=CC=2)=C1SC OMMIMDGHTTXEFT-UHFFFAOYSA-N 0.000 description 3
• LKDMKWNDBAVNQZ-UHFFFAOYSA-N 4-[[1-[[1-[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC(C)C(=O)NC(C)C(=O)N1CCCC1C(=O)NC(C(=O)NC=1C=CC(=CC=1)[N+]([O-])=O)CC1=CC=CC=C1 LKDMKWNDBAVNQZ-UHFFFAOYSA-N 0.000 description 3
• TVQSONUSFKVUHY-UHFFFAOYSA-N 5-methylsulfanyl-4-[4-(4-phenylphenyl)-1,3-thiazol-2-yl]thiophene-2-carboximidamide;hydrochloride Chemical compound Cl.S1C(C(N)=N)=CC(C=2SC=C(N=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1SC TVQSONUSFKVUHY-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• 125000005914 C6-C14 aryloxy group Chemical group 0.000 description 3
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