JP2002506818A - スタチン−マトリックスメタロプロテイナーゼ阻害剤組み合わせ物 - Google Patents
スタチン−マトリックスメタロプロテイナーゼ阻害剤組み合わせ物Info
- Publication number
- JP2002506818A JP2002506818A JP2000536378A JP2000536378A JP2002506818A JP 2002506818 A JP2002506818 A JP 2002506818A JP 2000536378 A JP2000536378 A JP 2000536378A JP 2000536378 A JP2000536378 A JP 2000536378A JP 2002506818 A JP2002506818 A JP 2002506818A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- methyl
- phenyl
- ethyl
- amino
- Prior art date
- 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
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title description 18
- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 title description 18
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims abstract description 88
- 229940124761 MMP inhibitor Drugs 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
- -1 flindostatin Chemical compound 0.000 claims description 552
- 239000002253 acid Substances 0.000 claims description 116
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 238000011282 treatment Methods 0.000 claims description 29
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 25
- AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 claims description 22
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 claims description 22
- BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 claims description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 21
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 16
- 201000001320 Atherosclerosis Diseases 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 15
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 15
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 15
- 229960004844 lovastatin Drugs 0.000 claims description 15
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 15
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 13
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 claims description 13
- 229960005110 cerivastatin Drugs 0.000 claims description 13
- 229960003765 fluvastatin Drugs 0.000 claims description 13
- 229960002855 simvastatin Drugs 0.000 claims description 13
- 230000000747 cardiac effect Effects 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- VDSBXXDKCUBMQC-HNGSOEQISA-N (4r,6s)-6-[(e)-2-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexen-1-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C1=C(F)C(C)=CC(C=2CC(C)(C)CC(C)(C)C=2\C=C\[C@H]2OC(=O)C[C@H](O)C2)=C1 VDSBXXDKCUBMQC-HNGSOEQISA-N 0.000 claims description 11
- 206010002383 Angina Pectoris Diseases 0.000 claims description 11
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 11
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 11
- VGMFHMLQOYWYHN-UHFFFAOYSA-N Compactin Natural products OCC1OC(OC2C(O)C(O)C(CO)OC2Oc3cc(O)c4C(=O)C(=COc4c3)c5ccc(O)c(O)c5)C(O)C(O)C1O VGMFHMLQOYWYHN-UHFFFAOYSA-N 0.000 claims description 11
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims description 11
- VXDSGTRNDFHIJB-QQPOVDNESA-N [(1s,4ar)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1CCC[C@@H](C21)OC(=O)[C@@H](C)CC)=CC(C)C2CC[C@@H]1C[C@@H](O)CC(=O)O1 VXDSGTRNDFHIJB-QQPOVDNESA-N 0.000 claims description 11
- 229960005370 atorvastatin Drugs 0.000 claims description 11
- 229950003040 dalvastatin Drugs 0.000 claims description 11
- VXDSGTRNDFHIJB-UHFFFAOYSA-N dihydrocompactin Natural products C12C(OC(=O)C(C)CC)CCCC2C=CC(C)C1CCC1CC(O)CC(=O)O1 VXDSGTRNDFHIJB-UHFFFAOYSA-N 0.000 claims description 11
- 229950009116 mevastatin Drugs 0.000 claims description 11
- 229960002965 pravastatin Drugs 0.000 claims description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- OJRHUICOVVSGSY-RXMQYKEDSA-N (2s)-2-chloro-3-methylbutan-1-ol Chemical compound CC(C)[C@H](Cl)CO OJRHUICOVVSGSY-RXMQYKEDSA-N 0.000 claims description 7
- 229960001770 atorvastatin calcium Drugs 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 230000002411 adverse Effects 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 210000004351 coronary vessel Anatomy 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 210000001715 carotid artery Anatomy 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- FJLGEFLZQAZZCD-JUFISIKESA-N (3S,5R)-fluvastatin Chemical compound C12=CC=CC=C2N(C(C)C)C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 FJLGEFLZQAZZCD-JUFISIKESA-N 0.000 claims 9
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims 6
- 230000000055 hyoplipidemic effect Effects 0.000 claims 4
- GJOCABIDMCKCEG-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)C)C(O)=O)=CC=C1C1=CC=C(Br)C=C1 GJOCABIDMCKCEG-UHFFFAOYSA-N 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 230000002093 peripheral effect Effects 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 abstract description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 156
- XSFAQQLHYUBFKV-UHFFFAOYSA-N 4-(4-phenylphenyl)butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=CC=C1 XSFAQQLHYUBFKV-UHFFFAOYSA-N 0.000 description 104
- 150000001408 amides Chemical class 0.000 description 90
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 88
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 81
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 79
- 150000001875 compounds Chemical class 0.000 description 76
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 57
- 229960003136 leucine Drugs 0.000 description 55
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 53
- 239000004395 L-leucine Substances 0.000 description 52
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 49
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 46
- 235000019454 L-leucine Nutrition 0.000 description 39
- 229910052739 hydrogen Inorganic materials 0.000 description 39
- 239000001257 hydrogen Substances 0.000 description 39
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 36
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 35
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 32
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 32
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 29
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 28
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 26
- 150000002431 hydrogen Chemical class 0.000 description 25
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 24
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 24
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 23
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 239000004471 Glycine Substances 0.000 description 18
- BPKJNEIOHOEWLO-UHFFFAOYSA-N 2-amino-n,3,3-trimethylbutanamide Chemical compound CNC(=O)C(N)C(C)(C)C BPKJNEIOHOEWLO-UHFFFAOYSA-N 0.000 description 17
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 17
- 239000003814 drug Substances 0.000 description 15
- AYORUWNJMKYNAD-JEDNCBNOSA-N 2-aminoacetic acid;(2s)-2-amino-4-methylpentanoic acid Chemical compound NCC(O)=O.CC(C)C[C@H](N)C(O)=O AYORUWNJMKYNAD-JEDNCBNOSA-N 0.000 description 14
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- 230000003902 lesion Effects 0.000 description 14
- BVRKOQJETMBIDK-VIFPVBQESA-N (2s)-2-amino-n-methyl-3-phenylpropanamide Chemical compound CNC(=O)[C@@H](N)CC1=CC=CC=C1 BVRKOQJETMBIDK-VIFPVBQESA-N 0.000 description 13
- 206010020772 Hypertension Diseases 0.000 description 13
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 13
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 13
- 239000012458 free base Substances 0.000 description 12
- 210000002376 aorta thoracic Anatomy 0.000 description 11
- 238000003556 assay Methods 0.000 description 11
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- VPMJTASZJZRIMH-YFKPBYRVSA-N (2s)-n-methylpiperazine-2-carboxamide Chemical compound CNC(=O)[C@@H]1CNCCN1 VPMJTASZJZRIMH-YFKPBYRVSA-N 0.000 description 10
- 206010019280 Heart failures Diseases 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 10
- 150000002632 lipids Chemical class 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 230000002861 ventricular Effects 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 9
- 229960003767 alanine Drugs 0.000 description 9
- 235000012000 cholesterol Nutrition 0.000 description 9
- 208000029078 coronary artery disease Diseases 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 9
- 229960005190 phenylalanine Drugs 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
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 8
- 239000005711 Benzoic acid Substances 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 238000002586 coronary angiography Methods 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 210000002540 macrophage Anatomy 0.000 description 8
- 125000001402 nonanoyl 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])[H] 0.000 description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 235000010233 benzoic acid Nutrition 0.000 description 7
- 230000002526 effect on cardiovascular system Effects 0.000 description 7
- 238000002604 ultrasonography Methods 0.000 description 7
- XRBKJPNGRGETAO-UHFFFAOYSA-N 2-amino-3,3-dimethyl-n-(2-phenylethyl)butanamide Chemical compound CC(C)(C)C(N)C(=O)NCCC1=CC=CC=C1 XRBKJPNGRGETAO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 108010007622 LDL Lipoproteins Proteins 0.000 description 6
- 102000007330 LDL Lipoproteins Human genes 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 208000031816 Pathologic Dilatation Diseases 0.000 description 6
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 6
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 description 6
- 235000005911 diet Nutrition 0.000 description 6
- 230000037213 diet Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 125000006308 propyl amino group Chemical group 0.000 description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 5
- IVNJKQPHHPMONX-WCCKRBBISA-N 2-aminoacetic acid;(2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid Chemical compound NCC(O)=O.OC(=O)[C@@H](N)CCCNC(N)=N IVNJKQPHHPMONX-WCCKRBBISA-N 0.000 description 5
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 5
- 235000004279 alanine Nutrition 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- 125000006309 butyl amino group Chemical group 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- NITYDPDXAAFEIT-DYVFJYSZSA-N ilomastat Chemical compound C1=CC=C2C(C[C@@H](C(=O)NC)NC(=O)[C@H](CC(C)C)CC(=O)NO)=CNC2=C1 NITYDPDXAAFEIT-DYVFJYSZSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 5
- VPMJTASZJZRIMH-UHFFFAOYSA-N n-methylpiperazine-2-carboxamide Chemical compound CNC(=O)C1CNCCN1 VPMJTASZJZRIMH-UHFFFAOYSA-N 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 5
- 235000019260 propionic acid Nutrition 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- ZQXYDSXOIXNPBN-RUZDIDTESA-N (2r)-3-phenyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)C1=CC=CC=C1 ZQXYDSXOIXNPBN-RUZDIDTESA-N 0.000 description 4
- HEABEIGWLYMIBY-JOCHJYFZSA-N (2r)-4-methyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]pentanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@H](CC(C)C)C(O)=O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 HEABEIGWLYMIBY-JOCHJYFZSA-N 0.000 description 4
- ZQXYDSXOIXNPBN-VWLOTQADSA-N (2s)-3-phenyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)C1=CC=CC=C1 ZQXYDSXOIXNPBN-VWLOTQADSA-N 0.000 description 4
- HEABEIGWLYMIBY-QFIPXVFZSA-N (2s)-4-methyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]pentanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](CC(C)C)C(O)=O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 HEABEIGWLYMIBY-QFIPXVFZSA-N 0.000 description 4
- ORQXBVXKBGUSBA-UHFFFAOYSA-N 2-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)C(N)CC1CCCCC1 ORQXBVXKBGUSBA-UHFFFAOYSA-N 0.000 description 4
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- XOKVBTKTLBLNSW-UHFFFAOYSA-N 4-oxo-4-[4-(4-phenylpiperidin-1-yl)phenyl]butanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 XOKVBTKTLBLNSW-UHFFFAOYSA-N 0.000 description 4
- BYHDDXPKOZIZRV-UHFFFAOYSA-N 5-phenylpentanoic acid Chemical compound OC(=O)CCCCC1=CC=CC=C1 BYHDDXPKOZIZRV-UHFFFAOYSA-N 0.000 description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 description 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 4
- 229930182821 L-proline Natural products 0.000 description 4
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 4
- 239000000006 Nitroglycerin Substances 0.000 description 4
- OATSQCXMYKYFQO-UHFFFAOYSA-N S-methyl ethanethioic acid ester Natural products CSC(C)=O OATSQCXMYKYFQO-UHFFFAOYSA-N 0.000 description 4
- XFILPEOLDIKJHX-QYZOEREBSA-N batimastat Chemical compound C([C@@H](C(=O)NC)NC(=O)[C@H](CC(C)C)[C@H](CSC=1SC=CC=1)C(=O)NO)C1=CC=CC=C1 XFILPEOLDIKJHX-QYZOEREBSA-N 0.000 description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 229960003711 glyceryl trinitrate Drugs 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000010412 perfusion Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- 239000000902 placebo Substances 0.000 description 4
- 229940068196 placebo Drugs 0.000 description 4
- 229960002429 proline Drugs 0.000 description 4
- 238000011002 quantification Methods 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229940083542 sodium Drugs 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229960004799 tryptophan Drugs 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229960004295 valine Drugs 0.000 description 4
- ULOTXPTWJAUGGE-MHZLTWQESA-N (2s)-3-(1h-indol-3-yl)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)S(=O)(=O)C(C=C1)=CC=C1N(CC1)CCC1C1=CC=CC=C1 ULOTXPTWJAUGGE-MHZLTWQESA-N 0.000 description 3
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 3
- VKGPPZZCLLKFLA-UHFFFAOYSA-N 2-(butylamino)-n-methylacetamide Chemical compound CCCCNCC(=O)NC VKGPPZZCLLKFLA-UHFFFAOYSA-N 0.000 description 3
- NZZDABAGUVZGON-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[[2-(4-tert-butylphenoxy)acetyl]amino]hexanoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 NZZDABAGUVZGON-UHFFFAOYSA-N 0.000 description 3
- NMBNLIBIDNBQFI-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[[2-(cyclopenten-1-yl)acetyl]amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CCCC1 NMBNLIBIDNBQFI-UHFFFAOYSA-N 0.000 description 3
- MESYIOOBFZHROK-UHFFFAOYSA-N 2-amino-N,2,3-trimethylbutanamide Chemical compound CNC(=O)C(C)(N)C(C)C MESYIOOBFZHROK-UHFFFAOYSA-N 0.000 description 3
- SBXDENYROQKXBE-UHFFFAOYSA-N 2-phenylbenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 SBXDENYROQKXBE-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 3
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- WQIRLJOPXYUOCI-UHFFFAOYSA-N 6-[[2-(1,3-benzodioxol-5-yl)acetyl]amino]-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]hexanoic acid Chemical compound C=1C=C2OCOC2=CC=1CC(=O)NCCCCC(C(=O)O)NS(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Br)C=C1 WQIRLJOPXYUOCI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 102000029816 Collagenase Human genes 0.000 description 3
- 108060005980 Collagenase Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 108010010234 HDL Lipoproteins Proteins 0.000 description 3
- 101000879758 Homo sapiens Sjoegren syndrome nuclear autoantigen 1 Proteins 0.000 description 3
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 3
- 102100030417 Matrilysin Human genes 0.000 description 3
- 108090000855 Matrilysin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 102100037330 Sjoegren syndrome nuclear autoantigen 1 Human genes 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DSFVQIUBODXRLL-UHFFFAOYSA-N acetamide;dihydrochloride Chemical compound Cl.Cl.CC(N)=O DSFVQIUBODXRLL-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 210000000709 aorta Anatomy 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000003143 atherosclerotic effect Effects 0.000 description 3
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 229960002424 collagenase Drugs 0.000 description 3
- 210000002808 connective tissue Anatomy 0.000 description 3
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 3
- 229960001395 fenbufen Drugs 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 3
- 150000002596 lactones Chemical group 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- BSIZUMJRKYHEBR-QGZVFWFLSA-N n-hydroxy-2(r)-[[(4-methoxyphenyl)sulfonyl](3-picolyl)amino]-3-methylbutanamide hydrochloride Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N([C@H](C(C)C)C(=O)NO)CC1=CC=CN=C1 BSIZUMJRKYHEBR-QGZVFWFLSA-N 0.000 description 3
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- REKHMRWKZZYTDP-KLLZUTDZSA-N (2S)-2-(dibenzofuran-2-ylsulfonylamino)-3-methylpentanoic acid Chemical compound C1=C(C=CC=2OC3=C(C=21)C=CC=C3)S(=O)(=O)N[C@H](C(=O)O)C(CC)C REKHMRWKZZYTDP-KLLZUTDZSA-N 0.000 description 2
- DVIKVXSMRJYYDK-SFHVURJKSA-N (2S)-2-(dibenzofuran-2-ylsulfonylamino)-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2C3=CC=CC=C3OC2=CC=1)C1=CC=CC=C1 DVIKVXSMRJYYDK-SFHVURJKSA-N 0.000 description 2
- AMZYGAHWDZJLAN-HNNXBMFYSA-N (2S)-2-(dibenzofuran-2-ylsulfonylamino)-4-methylpentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)N[C@@H](CC(C)C)C(O)=O)=CC=C3OC2=C1 AMZYGAHWDZJLAN-HNNXBMFYSA-N 0.000 description 2
- YDGXLVKDGGLWPF-SCSAIBSYSA-N (2r)-1,3-thiazolidine-2-carboxamide Chemical compound NC(=O)[C@@H]1NCCS1 YDGXLVKDGGLWPF-SCSAIBSYSA-N 0.000 description 2
- CCLNNAZFIAEPBM-IBGZPJMESA-N (2r)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]-3-sulfanylpropanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](CS)C(=O)O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 CCLNNAZFIAEPBM-IBGZPJMESA-N 0.000 description 2
- XHTVHWPJPDRGQI-QNGWXLTQSA-N (2r)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]-3-tritylsulfanylpropanoic acid Chemical class C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XHTVHWPJPDRGQI-QNGWXLTQSA-N 0.000 description 2
- NUZCSVKFVKXZEM-GFCCVEGCSA-N (2r)-4-dibenzofuran-2-yl-4-oxo-2-[(2,2,2-trifluoroacetyl)amino]butanoic acid Chemical compound C1=CC=C2C3=CC(C(=O)C[C@H](C(=O)O)NC(=O)C(F)(F)F)=CC=C3OC2=C1 NUZCSVKFVKXZEM-GFCCVEGCSA-N 0.000 description 2
- YGNCGRVNRKDKCS-INIZCTEOSA-N (2s)-2-(dibenzofuran-2-ylsulfonylamino)-3-methylbutanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C3OC2=C1 YGNCGRVNRKDKCS-INIZCTEOSA-N 0.000 description 2
- YPOJAHGDLHWILP-IBGZPJMESA-N (2s)-2-(dibenzofuran-2-ylsulfonylamino)-4-phenylbutanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2C3=CC=CC=C3OC2=CC=1)CC1=CC=CC=C1 YPOJAHGDLHWILP-IBGZPJMESA-N 0.000 description 2
- DIMHQAITVXMHMQ-SANMLTNESA-N (2s)-2-[[4-(4-benzylpiperidin-1-yl)phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC=2C=CC=CC=2)CC1)C1=CC=CC=C1 DIMHQAITVXMHMQ-SANMLTNESA-N 0.000 description 2
- ADRXVXDGDFNWTL-JIDHJSLPSA-N (2s)-2-[[4-[4-(3-hydroxyphenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid;hydrobromide Chemical compound Br.C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCN(CC1)C=1C=C(O)C=CC=1)C1=CC=CC=C1 ADRXVXDGDFNWTL-JIDHJSLPSA-N 0.000 description 2
- HTOYWGIWQZQPSR-DEOSSOPVSA-N (2s)-2-[[4-[4-(4-chlorophenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCN(CC1)C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 HTOYWGIWQZQPSR-DEOSSOPVSA-N 0.000 description 2
- PNCLRHJDVNOKGF-DEOSSOPVSA-N (2s)-2-[[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCN(CC1)C=1C=CC(O)=CC=1)C1=CC=CC=C1 PNCLRHJDVNOKGF-DEOSSOPVSA-N 0.000 description 2
- DCXSZYLYDZGFMN-LBPRGKRZSA-N (2s)-2-amino-4-dibenzofuran-2-yl-4-oxobutanoic acid Chemical compound C1=CC=C2C3=CC(C(=O)C[C@H](N)C(O)=O)=CC=C3OC2=C1 DCXSZYLYDZGFMN-LBPRGKRZSA-N 0.000 description 2
- IPPBZBAQYUONQO-YTTGMZPUSA-N (2s)-3-(4-phenylmethoxyphenyl)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)C(C=C1)=CC=C1OCC1=CC=CC=C1 IPPBZBAQYUONQO-YTTGMZPUSA-N 0.000 description 2
- ZHMTXQMPTXZPIY-QHCPKHFHSA-N (2s)-4-dibenzofuran-2-yl-2-(dodecanoylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C3=CC(C(=O)C[C@H](NC(=O)CCCCCCCCCCC)C(O)=O)=CC=C3OC2=C1 ZHMTXQMPTXZPIY-QHCPKHFHSA-N 0.000 description 2
- NMCAXOLGEVSANY-IBGZPJMESA-N (2s)-4-dibenzofuran-2-yl-4-oxo-2-[(2-phenylacetyl)amino]butanoic acid Chemical compound N([C@@H](CC(=O)C=1C=C2C3=CC=CC=C3OC2=CC=1)C(=O)O)C(=O)CC1=CC=CC=C1 NMCAXOLGEVSANY-IBGZPJMESA-N 0.000 description 2
- DTTSJWNGBWEGJL-DEOSSOPVSA-N (2s)-4-dibenzofuran-2-yl-4-oxo-2-[(4-phenylbenzoyl)amino]butanoic acid Chemical compound N([C@@H](CC(=O)C=1C=C2C3=CC=CC=C3OC2=CC=1)C(=O)O)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DTTSJWNGBWEGJL-DEOSSOPVSA-N 0.000 description 2
- SMCUDZWBQOPQEA-SANMLTNESA-N (2s)-4-phenyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]butanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)CC1=CC=CC=C1 SMCUDZWBQOPQEA-SANMLTNESA-N 0.000 description 2
- ZGGHKIMDNBDHJB-RPQBTBOMSA-M (3S,5R)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@H](O)C[C@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-RPQBTBOMSA-M 0.000 description 2
- XDLSSXYTUMNOHY-AWEZNQCLSA-N (3s)-3-[(dibenzofuran-2-ylsulfonylamino)methyl]-5-methylhexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC[C@@H](CC(C)C)CC(O)=O)=CC=C3OC2=C1 XDLSSXYTUMNOHY-AWEZNQCLSA-N 0.000 description 2
- LNGVLSZEFFMWIU-OHYPFYFLSA-N (4z)-4-phenylmethoxyimino-4-[4-(4-phenylpiperidin-1-yl)phenyl]butanoic acid Chemical compound C=1C=C(N2CCC(CC2)C=2C=CC=CC=2)C=CC=1C(/CCC(=O)O)=N\OCC1=CC=CC=C1 LNGVLSZEFFMWIU-OHYPFYFLSA-N 0.000 description 2
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 2
- IDLCHIYQDJIYKY-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)acetic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NCC(=O)O)=CC=C3OC2=C1 IDLCHIYQDJIYKY-UHFFFAOYSA-N 0.000 description 2
- SZUBKECHPDTJKS-UHFFFAOYSA-N 2-[(2-ethoxyphenyl)methyl-octylsulfonylamino]-n-hydroxyacetamide Chemical compound CCCCCCCCS(=O)(=O)N(CC(=O)NO)CC1=CC=CC=C1OCC SZUBKECHPDTJKS-UHFFFAOYSA-N 0.000 description 2
- HPNHKFGCOBDJOL-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl-octylsulfonylamino]-n-hydroxyacetamide Chemical compound CCCCCCCCS(=O)(=O)N(CC(=O)NO)CC1=CC=C(Cl)C=C1 HPNHKFGCOBDJOL-UHFFFAOYSA-N 0.000 description 2
- LGJCTCXTISERQE-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenyl)phenyl]-2-hydroxyiminoethyl]-5-(1,3-dioxoisoindol-2-yl)-2-fluoropentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(F)(C(O)=O)CC(=NO)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 LGJCTCXTISERQE-UHFFFAOYSA-N 0.000 description 2
- QIOYIGUCVWDDSG-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenyl)phenyl]-2-hydroxyiminoethyl]-6-(1,3-dioxoisoindol-2-yl)-2-fluorohexanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCC(F)(C(O)=O)CC(=NO)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 QIOYIGUCVWDDSG-UHFFFAOYSA-N 0.000 description 2
- OUNUWEGDJDDKQT-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(2-naphthalen-1-yloxyacetyl)amino]hexanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1OCC(=O)NCCCCC(C(=O)O)NS(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Br)C=C1 OUNUWEGDJDDKQT-UHFFFAOYSA-N 0.000 description 2
- DLOYPNWOLLZVLA-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(2-pyridin-2-ylacetyl)amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CC=N1 DLOYPNWOLLZVLA-UHFFFAOYSA-N 0.000 description 2
- QDFHMGIGICIHTR-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(2-pyridin-3-ylacetyl)amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CN=C1 QDFHMGIGICIHTR-UHFFFAOYSA-N 0.000 description 2
- AFFUQTQAJDIUKC-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[3-(4-methoxyphenyl)propanoylamino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1CCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 AFFUQTQAJDIUKC-UHFFFAOYSA-N 0.000 description 2
- BAYMWVAVTBHBAI-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[4-(4-chloro-3-methylphenoxy)butanoylamino]hexanoic acid Chemical compound C1=C(Cl)C(C)=CC(OCCCC(=O)NCCCCC(NS(=O)(=O)C=2C=CC(=CC=2)C=2C=CC(Br)=CC=2)C(O)=O)=C1 BAYMWVAVTBHBAI-UHFFFAOYSA-N 0.000 description 2
- KCAUFUXREROFOX-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[[2-(4-nitrophenoxy)acetyl]amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)COC1=CC=C([N+]([O-])=O)C=C1 KCAUFUXREROFOX-UHFFFAOYSA-N 0.000 description 2
- ZEEYNQNRMIBLMK-DFWYDOINSA-N 2-aminoacetic acid;(2s)-2-aminopentanedioic acid Chemical compound NCC(O)=O.OC(=O)[C@@H](N)CCC(O)=O ZEEYNQNRMIBLMK-DFWYDOINSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- HJTFFMFCFQJNJZ-UHFFFAOYSA-N 2-dibenzofuran-2-yl-4-oxobutanoic acid Chemical compound C1=CC=C2C3=CC(C(CC=O)C(=O)O)=CC=C3OC2=C1 HJTFFMFCFQJNJZ-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 2
- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 2
- UYXSPCLQWKBUEW-UHFFFAOYSA-N 3-amino-1-methoxy-3,4-dihydroquinolin-2-one Chemical compound C1=CC=C2N(OC)C(=O)C(N)CC2=C1 UYXSPCLQWKBUEW-UHFFFAOYSA-N 0.000 description 2
- ANZIRVOGVJLJHE-UHFFFAOYSA-N 3-amino-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C(N)CC2=C1 ANZIRVOGVJLJHE-UHFFFAOYSA-N 0.000 description 2
- PKUGMMYQZAMIDX-UHFFFAOYSA-N 3-methyl-5-oxo-5-[4-(4-phenylpiperidin-1-yl)phenyl]pentanoic acid Chemical compound C1=CC(C(=O)CC(CC(O)=O)C)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 PKUGMMYQZAMIDX-UHFFFAOYSA-N 0.000 description 2
- LGJWPXGDZJETQK-UHFFFAOYSA-N 4-(2-phenylphenyl)butanoic acid Chemical compound OC(=O)CCCC1=CC=CC=C1C1=CC=CC=C1 LGJWPXGDZJETQK-UHFFFAOYSA-N 0.000 description 2
- ZYTOBAWIRVFDJA-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenyl)phenyl]-4-hydroxyiminobutanoic acid Chemical compound C1=CC(C(CCC(O)=O)=NO)=CC=C1C1=CC=C(Cl)C=C1Cl ZYTOBAWIRVFDJA-UHFFFAOYSA-N 0.000 description 2
- ZKAXZKMSZPJJAV-UHFFFAOYSA-N 4-[4-(4-bromo-2-fluorophenyl)phenyl]-4-hydroxyiminobutanoic acid Chemical compound C1=CC(C(CCC(O)=O)=NO)=CC=C1C1=CC=C(Br)C=C1F ZKAXZKMSZPJJAV-UHFFFAOYSA-N 0.000 description 2
- GIMDYSWWMCJCFQ-UHFFFAOYSA-N 4-[4-(4-bromophenyl)phenyl]-4-hydroxyiminobutanoic acid Chemical compound C1=CC(C(CCC(O)=O)=NO)=CC=C1C1=CC=C(Br)C=C1 GIMDYSWWMCJCFQ-UHFFFAOYSA-N 0.000 description 2
- IGXCIGJOOHSVAF-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2,2,3,3-tetrafluoro-4-hydroxyiminobutanoic acid Chemical compound C1=CC(C(=NO)C(F)(F)C(F)(F)C(O)=O)=CC=C1C1=CC=C(Cl)C=C1 IGXCIGJOOHSVAF-UHFFFAOYSA-N 0.000 description 2
- UTHIPJQXGSUBSL-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2-[2-(1,3-dioxobenzo[f]isoindol-2-yl)ethyl]-2-fluoro-4-hydroxyiminobutanoic acid Chemical compound O=C1C2=CC3=CC=CC=C3C=C2C(=O)N1CCC(F)(C(O)=O)CC(=NO)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 UTHIPJQXGSUBSL-UHFFFAOYSA-N 0.000 description 2
- PGMZAQDZZPRHLE-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-2-fluoro-4-hydroxyiminobutanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(F)(C(O)=O)CC(=NO)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 PGMZAQDZZPRHLE-UHFFFAOYSA-N 0.000 description 2
- ZJVVTRVFQVMDPY-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2-fluoro-4-hydroxyimino-2-(1H-indol-3-yl)-3-methylbutanoic acid Chemical compound ClC1=CC=C(C=C1)C1=CC=C(C=C1)C(C(C(C(=O)O)(C1=CNC2=CC=CC=C12)F)C)=NO ZJVVTRVFQVMDPY-UHFFFAOYSA-N 0.000 description 2
- RIPBPXRFYMYPAE-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2-fluoro-4-hydroxyimino-2-(2-phenylethyl)butanoic acid Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(=NO)CC(F)(C(O)=O)CCC1=CC=CC=C1 RIPBPXRFYMYPAE-UHFFFAOYSA-N 0.000 description 2
- QLOVCQFIZUKWFR-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2-fluoro-4-hydroxyimino-2-methylbutanoic acid Chemical compound C1=CC(C(=NO)CC(F)(C)C(O)=O)=CC=C1C1=CC=C(Cl)C=C1 QLOVCQFIZUKWFR-UHFFFAOYSA-N 0.000 description 2
- MZZSBYJTHHTGEM-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2-fluoro-4-hydroxyimino-3,3-dimethylbutanoic acid Chemical compound C1=CC(C(=NO)C(C)(C(F)C(O)=O)C)=CC=C1C1=CC=C(Cl)C=C1 MZZSBYJTHHTGEM-UHFFFAOYSA-N 0.000 description 2
- UGTUJSZRMWTLES-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-3-fluoro-4-oxobutanoic acid Chemical compound C1=CC(C(=O)C(F)CC(=O)O)=CC=C1C1=CC=C(Cl)C=C1 UGTUJSZRMWTLES-UHFFFAOYSA-N 0.000 description 2
- IYWKVPQGIPOZMN-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-4-hydroxybutanoic acid Chemical compound C1=CC(C(CCC(O)=O)O)=CC=C1C1=CC=C(Cl)C=C1 IYWKVPQGIPOZMN-UHFFFAOYSA-N 0.000 description 2
- JETIIFTUWCPZEG-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-4-methoxyiminobutanoic acid Chemical compound C1=CC(C(CCC(O)=O)=NOC)=CC=C1C1=CC=C(Cl)C=C1 JETIIFTUWCPZEG-UHFFFAOYSA-N 0.000 description 2
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 2
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 2
- SGJNBMOXAMANCI-UHFFFAOYSA-N 4-oxo-4-[4-(4-phenylpiperazin-1-yl)phenyl]butanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1N1CCN(C=2C=CC=CC=2)CC1 SGJNBMOXAMANCI-UHFFFAOYSA-N 0.000 description 2
- ZEUGUSAZSYOAMR-UHFFFAOYSA-N 7-amino-7-(1-methoxyethyl)-5,8-dihydro-[1,3]dioxolo[4,5-g]quinolin-6-one Chemical compound NC1(C(NC2=CC3=C(C=C2C1)OCO3)=O)C(C)OC ZEUGUSAZSYOAMR-UHFFFAOYSA-N 0.000 description 2
- 102100026802 72 kDa type IV collagenase Human genes 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- VTZRKSZNRLVLDI-UHFFFAOYSA-N C=1C=CC=CC=1C1=CC(CCCC(=O)O)=CC=C1C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C1=CC(CCCC(=O)O)=CC=C1C1=CC=CC=C1 VTZRKSZNRLVLDI-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 208000014882 Carotid artery disease Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 108010026132 Gelatinases Proteins 0.000 description 2
- 102000013382 Gelatinases Human genes 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 2
- 235000014852 L-arginine Nutrition 0.000 description 2
- 229930064664 L-arginine Natural products 0.000 description 2
- 108010028554 LDL Cholesterol Proteins 0.000 description 2
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 2
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 2
- 102000000422 Matrix Metalloproteinase 3 Human genes 0.000 description 2
- 108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- 102000056189 Neutrophil collagenases Human genes 0.000 description 2
- QPYYMFJNZAEBJP-XDOYNYLZSA-N O\N=C(\CCC(=O)O)/C1=CC=C(C=C1)N1CCC(CC1)C1=CC=CC=C1 Chemical compound O\N=C(\CCC(=O)O)/C1=CC=C(C=C1)N1CCC(CC1)C1=CC=CC=C1 QPYYMFJNZAEBJP-XDOYNYLZSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 208000031481 Pathologic Constriction Diseases 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 102100030416 Stromelysin-1 Human genes 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000002399 angioplasty Methods 0.000 description 2
- 239000004004 anti-anginal agent Substances 0.000 description 2
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 2
- 239000003529 anticholesteremic agent Substances 0.000 description 2
- 229940127226 anticholesterol agent Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229950001858 batimastat Drugs 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 229940000635 beta-alanine Drugs 0.000 description 2
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 2
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 2
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 208000037876 carotid Atherosclerosis Diseases 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001840 cholesterol esters Chemical class 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 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 description 2
- 230000007423 decrease Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 230000035487 diastolic blood pressure Effects 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- OCSMOTCMPXTDND-OUAUKWLOSA-N marimastat Chemical compound CNC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO OCSMOTCMPXTDND-OUAUKWLOSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 210000001616 monocyte Anatomy 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 230000000877 morphologic effect Effects 0.000 description 2
- 230000002107 myocardial effect Effects 0.000 description 2
- LXRAWBFAYXEXCY-UHFFFAOYSA-N n-hydroxy-2-[(2-methoxyphenyl)methyl-octylsulfonylamino]acetamide Chemical compound CCCCCCCCS(=O)(=O)N(CC(=O)NO)CC1=CC=CC=C1OC LXRAWBFAYXEXCY-UHFFFAOYSA-N 0.000 description 2
- BNOGOCHBBWMPKH-UHFFFAOYSA-N n-hydroxy-4-oxo-4-[4-(4-phenylpiperidin-1-yl)phenyl]butanamide Chemical compound C1=CC(C(=O)CCC(=O)NO)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 BNOGOCHBBWMPKH-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 229960001639 penicillamine Drugs 0.000 description 2
- 235000019371 penicillin G benzathine Nutrition 0.000 description 2
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 2
- OAWXZFGKDDFTGS-UHFFFAOYSA-N pyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCN1C(O)=O OAWXZFGKDDFTGS-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 102220240796 rs553605556 Human genes 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000036262 stenosis Effects 0.000 description 2
- 208000037804 stenosis Diseases 0.000 description 2
- 108091007196 stromelysin Proteins 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 230000035488 systolic blood pressure Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XONPOTGSFYKNMH-QHRIQVFBSA-N (1R,4S)-1-amino-4-[(2R)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoyl]-3-oxo-4,5-dihydro-2H-2-benzazepine-1-carboxylic acid Chemical compound OC(=O)[C@]1(N)NC(=O)[C@H](C(=O)[C@@H](CC(=O)NO)CC(C)C)CC2=CC=CC=C21 XONPOTGSFYKNMH-QHRIQVFBSA-N 0.000 description 1
- LSKVCOMPLXHQRD-KLLZUTDZSA-N (2S)-2-(dibenzofuran-2-ylsulfonylamino)-N-hydroxy-3-methylpentanamide Chemical compound ONC([C@H](C(CC)C)NS(=O)(=O)C1=CC2=C(OC3=C2C=CC=C3)C=C1)=O LSKVCOMPLXHQRD-KLLZUTDZSA-N 0.000 description 1
- KLJMAQDORBAMIU-LBPRGKRZSA-N (2S)-2-(dibenzofuran-2-ylsulfonylamino)butanedioic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)N[C@@H](CC(=O)O)C(O)=O)=CC=C3OC2=C1 KLJMAQDORBAMIU-LBPRGKRZSA-N 0.000 description 1
- ZIKZEEKTVYFKKF-VIFPVBQESA-N (2S)-2-(dibenzofuran-2-ylsulfonylamino)propanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)N[C@@H](C)C(O)=O)=CC=C3OC2=C1 ZIKZEEKTVYFKKF-VIFPVBQESA-N 0.000 description 1
- LWYIUYDHVWJHND-ZRFIFAGDSA-N (2S)-2-[3-(benzenesulfonyl)propyl]-5-[(3S)-3-(methylcarbamoyl)diazinan-4-yl]-5-oxopentanoic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)CCC[C@H](CCC(=O)C1[C@H](NNCC1)C(=O)NC)C(=O)O LWYIUYDHVWJHND-ZRFIFAGDSA-N 0.000 description 1
- TWIMRMWVRSEUBC-IXLXJOPFSA-N (2S)-2-[3-(benzenesulfonyl)propyl]-5-[(3S,4R)-1-[2-[2-(1H-imidazol-5-yl)phenyl]ethyl]-3-(methylcarbamoyl)diazinan-4-yl]-5-oxopentanoic acid Chemical compound N1C=NC(=C1)C1=C(C=CC=C1)CCN1N[C@@H]([C@@H](CC1)C(CC[C@H](C(=O)O)CCCS(=O)(=O)C1=CC=CC=C1)=O)C(=O)NC TWIMRMWVRSEUBC-IXLXJOPFSA-N 0.000 description 1
- FLOUJQGELDZGAD-IXLXJOPFSA-N (2S)-2-[3-(benzenesulfonyl)propyl]-5-[(3S,4R)-3-(methylcarbamoyl)-1-[2-[2-(1,3-oxazol-4-yl)phenyl]ethyl]diazinan-4-yl]-5-oxopentanoic acid Chemical compound O1C=NC(=C1)C1=C(C=CC=C1)CCN1N[C@@H]([C@@H](CC1)C(CC[C@H](C(=O)O)CCCS(=O)(=O)C1=CC=CC=C1)=O)C(=O)NC FLOUJQGELDZGAD-IXLXJOPFSA-N 0.000 description 1
- QWZQJTVPOJJYFH-IXLXJOPFSA-N (2S)-2-[3-(benzenesulfonyl)propyl]-5-[(3S,4R)-3-(methylcarbamoyl)-1-[2-[2-(1,3-thiazol-4-yl)phenyl]ethyl]diazinan-4-yl]-5-oxopentanoic acid Chemical compound S1C=NC(=C1)C1=C(C=CC=C1)CCN1N[C@@H]([C@@H](CC1)C(CC[C@H](C(=O)O)CCCS(=O)(=O)C1=CC=CC=C1)=O)C(=O)NC QWZQJTVPOJJYFH-IXLXJOPFSA-N 0.000 description 1
- ZWZUMHQJPFYTDW-CQSZACIVSA-N (2r)-2-[2-(4-propylphenyl)ethyl]pentanedioic acid Chemical compound CCCC1=CC=C(CC[C@H](CCC(O)=O)C(O)=O)C=C1 ZWZUMHQJPFYTDW-CQSZACIVSA-N 0.000 description 1
- PEYDLXUGPQEGEZ-SXOMAYOGSA-N (2r)-2-[[(2s)-1-(3,4-dihydro-1h-isoquinolin-2-yl)-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound C1CC2=CC=CC=C2CN1C(=O)[C@H](CC(C)C)N[C@@H](C(O)=O)CCN1C(=O)C2=CC3=CC=CC=C3C=C2C1=O PEYDLXUGPQEGEZ-SXOMAYOGSA-N 0.000 description 1
- ICHGEUHTXANQHK-RPWUZVMVSA-N (2r)-2-[[(2s)-1-(benzenesulfonamido)-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NS(=O)(=O)C1=CC=CC=C1 ICHGEUHTXANQHK-RPWUZVMVSA-N 0.000 description 1
- WFKFYEWTXWNLSQ-SXOMAYOGSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxo-5-phenylisoindol-2-yl)butanoic acid Chemical compound C([C@@H](N[C@@H](CC(C)C)C(=O)NCC=1C=CC=CC=1)C(O)=O)CN(C(C1=C2)=O)C(=O)C1=CC=C2C1=CC=CC=C1 WFKFYEWTXWNLSQ-SXOMAYOGSA-N 0.000 description 1
- IIWFEGCSOXADGA-IZLXSDGUSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxo-5-phenylmethoxyisoindol-2-yl)butanoic acid Chemical compound C([C@@H](N[C@@H](CC(C)C)C(=O)NCC=1C=CC=CC=1)C(O)=O)CN(C(C1=C2)=O)C(=O)C1=CC=C2OCC1=CC=CC=C1 IIWFEGCSOXADGA-IZLXSDGUSA-N 0.000 description 1
- OEVLRZHPDAKFSL-RPBOFIJWSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC=C1 OEVLRZHPDAKFSL-RPBOFIJWSA-N 0.000 description 1
- JTBZFSJOPYDYET-RTWAWAEBSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxoisoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC=CC=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC=C1 JTBZFSJOPYDYET-RTWAWAEBSA-N 0.000 description 1
- PMIJVUFNNNWTGM-RTWAWAEBSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(5-bromo-1,3-dioxoisoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC(Br)=CC=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC=C1 PMIJVUFNNNWTGM-RTWAWAEBSA-N 0.000 description 1
- MYKPZWYAUWGNBK-RTWAWAEBSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(5-hydroxy-1,3-dioxoisoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC(O)=CC=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC=C1 MYKPZWYAUWGNBK-RTWAWAEBSA-N 0.000 description 1
- NRTVWBJZZYOKED-YADHBBJMSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(5-methoxy-1,3-dioxoisoindol-2-yl)butanoic acid Chemical compound O=C([C@H](CC(C)C)N[C@H](CCN1C(=O)C2=CC=C(C=C2C1=O)OC)C(O)=O)NCC1=CC=CC=C1 NRTVWBJZZYOKED-YADHBBJMSA-N 0.000 description 1
- IXTKFCQDFVQZER-YADHBBJMSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(5-methyl-1,3-dioxoisoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC(C)=CC=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC=C1 IXTKFCQDFVQZER-YADHBBJMSA-N 0.000 description 1
- VCHWUNXMFWLHLZ-RTWAWAEBSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-(5-nitro-1,3-dioxoisoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC(=CC=C2C1=O)[N+]([O-])=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC=C1 VCHWUNXMFWLHLZ-RTWAWAEBSA-N 0.000 description 1
- SXQIDVASQRSUIF-YADHBBJMSA-N (2r)-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-4-[5-(methanesulfonamido)-1,3-dioxoisoindol-2-yl]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC(NS(C)(=O)=O)=CC=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC=C1 SXQIDVASQRSUIF-YADHBBJMSA-N 0.000 description 1
- OWGNKOYIRGADIM-RPBOFIJWSA-N (2r)-2-[[(2s)-1-[(2,4-difluorophenyl)methylamino]-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=C(F)C=C1F OWGNKOYIRGADIM-RPBOFIJWSA-N 0.000 description 1
- MHBFBUKLOWTBPY-RPBOFIJWSA-N (2r)-2-[[(2s)-1-[(3,4-difluorophenyl)methylamino]-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=C(F)C(F)=C1 MHBFBUKLOWTBPY-RPBOFIJWSA-N 0.000 description 1
- BNKKKKHJWPHQMB-RPBOFIJWSA-N (2r)-2-[[(2s)-1-[(3,5-difluorophenyl)methylamino]-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC(F)=CC(F)=C1 BNKKKKHJWPHQMB-RPBOFIJWSA-N 0.000 description 1
- AZLHBMNZAQOGTN-PKTZIBPZSA-N (2r)-2-[[(2s)-1-[2-(dimethylamino)ethyl-methylamino]-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound C1=CC=C2C=C(C(N(CC[C@@H](N[C@@H](CC(C)C)C(=O)N(C)CCN(C)C)C(O)=O)C3=O)=O)C3=CC2=C1 AZLHBMNZAQOGTN-PKTZIBPZSA-N 0.000 description 1
- GXWYXLCRFPADNN-PEXCGTIESA-N (2r)-2-[[(2s)-1-[4-(2,3-dihydroxypropyl)piperazin-1-yl]-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)N1CCN(CC(O)CO)CC1 GXWYXLCRFPADNN-PEXCGTIESA-N 0.000 description 1
- HINNHPLLAXUVHW-DSNGMDLFSA-N (2r)-2-[[(2s)-1-[[(3s)-1-azabicyclo[2.2.2]octan-3-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)[C@H](CC(C)C)N[C@@H](C(O)=O)CCN1C(=O)C2=CC3=CC=CC=C3C=C2C1=O HINNHPLLAXUVHW-DSNGMDLFSA-N 0.000 description 1
- LRKDRDGVDDKDFI-RTWAWAEBSA-N (2r)-2-[[(2s)-1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-(1,3-dioxobenzo[f]isoindol-2-yl)butanoic acid Chemical compound C1=CC=C2C=C(C(N(CC[C@@H](N[C@@H](CC(C)C)C(=O)NC(CO)(CO)CO)C(O)=O)C3=O)=O)C3=CC2=C1 LRKDRDGVDDKDFI-RTWAWAEBSA-N 0.000 description 1
- VKUYLANQOAKALN-LJQANCHMSA-N (2r)-2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N([C@H](CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-LJQANCHMSA-N 0.000 description 1
- NGBPLGFXVZXMPW-HXUWFJFHSA-N (2r)-2-cyclohexyl-n-hydroxy-2-[(4-methoxyphenyl)sulfonyl-(pyridin-3-ylmethyl)amino]acetamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N([C@H](C1CCCCC1)C(=O)NO)CC1=CC=CN=C1 NGBPLGFXVZXMPW-HXUWFJFHSA-N 0.000 description 1
- GAUZBXUVFZCFTL-HXUWFJFHSA-N (2r)-2-cyclohexyl-n-hydroxy-2-[(4-methoxyphenyl)sulfonyl-(pyridin-4-ylmethyl)amino]acetamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N([C@H](C1CCCCC1)C(=O)NO)CC1=CC=NC=C1 GAUZBXUVFZCFTL-HXUWFJFHSA-N 0.000 description 1
- KLTRUHCZEUFBCI-RTWAWAEBSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-1-(1h-imidazol-2-ylmethylamino)-4-methyl-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=NC=CN1 KLTRUHCZEUFBCI-RTWAWAEBSA-N 0.000 description 1
- XQLNWPJNKWCJNN-YPFKAFGZSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-1-[(1,1-dioxothiolan-3-yl)amino]-4-methyl-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NC1CCS(=O)(=O)C1 XQLNWPJNKWCJNN-YPFKAFGZSA-N 0.000 description 1
- ZPYLLHLHJRMHKM-RPBOFIJWSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-1-[(3-fluorophenyl)methylamino]-4-methyl-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC(F)=C1 ZPYLLHLHJRMHKM-RPBOFIJWSA-N 0.000 description 1
- AMUUVVZQQBNBAH-GEOZSUPMSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-1-[(4-hydroxy-1,1-dioxothiolan-3-yl)amino]-4-methyl-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NC1CS(=O)(=O)CC1O AMUUVVZQQBNBAH-GEOZSUPMSA-N 0.000 description 1
- XPJMBJXJAGTHDT-PKTZIBPZSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-1-[2-(1h-imidazol-5-yl)ethylamino]-4-methyl-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCCC1=CNC=N1 XPJMBJXJAGTHDT-PKTZIBPZSA-N 0.000 description 1
- RMIRCZYCHSFPLY-FTJBHMTQSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-1-[[3-(methanesulfonamido)phenyl]methylamino]-4-methyl-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC(NS(C)(=O)=O)=C1 RMIRCZYCHSFPLY-FTJBHMTQSA-N 0.000 description 1
- HKQCSEWOGBFFLV-RPWUZVMVSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-(2-morpholin-4-ylethylamino)-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCCN1CCOCC1 HKQCSEWOGBFFLV-RPWUZVMVSA-N 0.000 description 1
- IHNXSBCQZROJCS-PKTZIBPZSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-(4-methylpiperazin-1-yl)-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)N1CCN(C)CC1 IHNXSBCQZROJCS-PKTZIBPZSA-N 0.000 description 1
- CLDWFWQEHSJBDI-MOPGFXCFSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-(methylamino)-1-oxopentan-2-yl]amino]butanoic acid Chemical compound C1=CC=C2C=C(C(N(CC[C@@H](N[C@@H](CC(C)C)C(=O)NC)C(O)=O)C3=O)=O)C3=CC2=C1 CLDWFWQEHSJBDI-MOPGFXCFSA-N 0.000 description 1
- PUWSCJOQJNHFGL-UXHICEINSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-[(1-methyltetrazol-5-yl)methylamino]-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=NN=NN1C PUWSCJOQJNHFGL-UXHICEINSA-N 0.000 description 1
- XNTKFDGCIFUJAN-PKTZIBPZSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-[(2-methyl-6-oxo-1h-pyrimidin-5-yl)methylamino]-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CN=C(C)N=C1O XNTKFDGCIFUJAN-PKTZIBPZSA-N 0.000 description 1
- QNXOSJQPBDWRPV-RPBOFIJWSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-[(3-nitrophenyl)methylamino]-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC([N+]([O-])=O)=C1 QNXOSJQPBDWRPV-RPBOFIJWSA-N 0.000 description 1
- AFPQONWUVKKBTL-RPBOFIJWSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-[(4-nitrophenyl)methylamino]-1-oxopentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=C([N+]([O-])=O)C=C1 AFPQONWUVKKBTL-RPBOFIJWSA-N 0.000 description 1
- QQTWJGZZLJPVHO-OEBVTXOESA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-(1,2,3,4-tetrahydronaphthalen-1-ylamino)pentan-2-yl]amino]butanoic acid Chemical compound C1CCC2=CC=CC=C2C1NC(=O)[C@H](CC(C)C)N[C@@H](C(O)=O)CCN1C(=O)C2=CC3=CC=CC=C3C=C2C1=O QQTWJGZZLJPVHO-OEBVTXOESA-N 0.000 description 1
- QMKYZDVPHOZDSO-YADHBBJMSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-(1-oxo-1,4-thiazinan-4-yl)pentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)N1CCS(=O)CC1 QMKYZDVPHOZDSO-YADHBBJMSA-N 0.000 description 1
- YSOWDIROXDYGJM-FTJBHMTQSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-(2-phenylethylamino)pentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCCC1=CC=CC=C1 YSOWDIROXDYGJM-FTJBHMTQSA-N 0.000 description 1
- STUVZGRGAUKZRU-RPWUZVMVSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-(pyridin-2-ylmethylamino)pentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC=N1 STUVZGRGAUKZRU-RPWUZVMVSA-N 0.000 description 1
- FVPFSBPZTBSLES-KWXIBIRDSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-[(2r)-3-oxo-2-phenylpiperazin-1-yl]pentan-2-yl]amino]butanoic acid Chemical compound C1([C@@H]2C(=O)NCCN2C(=O)[C@@H](N[C@H](CCN2C(C3=CC4=CC=CC=C4C=C3C2=O)=O)C(O)=O)CC(C)C)=CC=CC=C1 FVPFSBPZTBSLES-KWXIBIRDSA-N 0.000 description 1
- FVPFSBPZTBSLES-PVHODMMVSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-[(2s)-3-oxo-2-phenylpiperazin-1-yl]pentan-2-yl]amino]butanoic acid Chemical compound C1([C@H]2C(=O)NCCN2C(=O)[C@@H](N[C@H](CCN2C(C3=CC4=CC=CC=C4C=C3C2=O)=O)C(O)=O)CC(C)C)=CC=CC=C1 FVPFSBPZTBSLES-PVHODMMVSA-N 0.000 description 1
- BOROQFAWARDBDC-RPBOFIJWSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-[(4-sulfamoylphenyl)methylamino]pentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=C(S(N)(=O)=O)C=C1 BOROQFAWARDBDC-RPBOFIJWSA-N 0.000 description 1
- XDYXNRAZWFJWNQ-RREDXGFBSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-[1-(6-oxo-1h-pyridazin-3-yl)ethylamino]pentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NC(C)C=1C=CC(=O)NN=1 XDYXNRAZWFJWNQ-RREDXGFBSA-N 0.000 description 1
- UAZHKINNICKCCP-BAEUJYSMSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-[[(1r)-1-phenylethyl]amino]pentan-2-yl]amino]butanoic acid Chemical compound C1([C@@H](C)NC(=O)[C@@H](N[C@H](CCN2C(C3=CC4=CC=CC=C4C=C3C2=O)=O)C(O)=O)CC(C)C)=CC=CC=C1 UAZHKINNICKCCP-BAEUJYSMSA-N 0.000 description 1
- UAZHKINNICKCCP-YZYNAAERSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-[[(1s)-1-phenylethyl]amino]pentan-2-yl]amino]butanoic acid Chemical compound C1([C@H](C)NC(=O)[C@@H](N[C@H](CCN2C(C3=CC4=CC=CC=C4C=C3C2=O)=O)C(O)=O)CC(C)C)=CC=CC=C1 UAZHKINNICKCCP-YZYNAAERSA-N 0.000 description 1
- OGMYPFNPKBZPNP-NJYVYQBISA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-[[(3r)-2-oxothiolan-3-yl]amino]pentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)N[C@@H]1CCSC1=O OGMYPFNPKBZPNP-NJYVYQBISA-N 0.000 description 1
- KXKANFPJEICPJZ-RPBOFIJWSA-N (2r)-4-(1,3-dioxobenzo[f]isoindol-2-yl)-2-[[(2s)-4-methyl-1-oxo-1-[[3-(trifluoromethyl)phenyl]methylamino]pentan-2-yl]amino]butanoic acid Chemical compound O=C([C@@H](N[C@H](CCN1C(C2=CC3=CC=CC=C3C=C2C1=O)=O)C(O)=O)CC(C)C)NCC1=CC=CC(C(F)(F)F)=C1 KXKANFPJEICPJZ-RPBOFIJWSA-N 0.000 description 1
- FOBJBXPKRCKRHZ-SXOMAYOGSA-N (2r)-4-[5-(benzenesulfonamido)-1,3-dioxoisoindol-2-yl]-2-[[(2s)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]butanoic acid Chemical compound C([C@@H](N[C@@H](CC(C)C)C(=O)NCC=1C=CC=CC=1)C(O)=O)CN(C(C1=C2)=O)C(=O)C1=CC=C2NS(=O)(=O)C1=CC=CC=C1 FOBJBXPKRCKRHZ-SXOMAYOGSA-N 0.000 description 1
- OIVAPLYJZKBFMV-KGLIPLIRSA-N (2r)-n'-hydroxy-n-[(3s)-1-methoxy-2-oxo-3,4-dihydroquinolin-3-yl]-2-(2-methylpropyl)butanediamide Chemical compound C1=CC=C2N(OC)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)CC(=O)NO)CC2=C1 OIVAPLYJZKBFMV-KGLIPLIRSA-N 0.000 description 1
- INENOFVMNCJCMW-STSQHVNTSA-N (2r,3r)-3-[(1s)-1-amino-3-oxo-4,5-dihydro-2h-2-benzazepine-1-carbonyl]-n-hydroxy-5-methyl-2-(morpholin-4-ylmethyl)hexanamide Chemical compound C([C@@H]([C@@H](CC(C)C)C(=O)[C@]1(N)C2=CC=CC=C2CCC(=O)N1)C(=O)NO)N1CCOCC1 INENOFVMNCJCMW-STSQHVNTSA-N 0.000 description 1
- DEFJQIDDEAULHB-BKLSDQPFSA-N (2s)-2-(2-aminopropanoylamino)propanoic acid Chemical compound CC(N)C(=O)N[C@@H](C)C(O)=O DEFJQIDDEAULHB-BKLSDQPFSA-N 0.000 description 1
- JWHMHRXXUPPKGV-INIZCTEOSA-N (2s)-2-(dibenzofuran-3-ylsulfonylamino)-3-methylbutanoic acid Chemical compound C1=CC=C2C3=CC=C(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)C=C3OC2=C1 JWHMHRXXUPPKGV-INIZCTEOSA-N 0.000 description 1
- JJPPFLGOODJQBO-LBPRGKRZSA-N (2s)-2-(dibenzofuran-3-ylsulfonylamino)butanedioic acid Chemical compound C1=CC=C2C3=CC=C(S(=O)(=O)N[C@@H](CC(=O)O)C(O)=O)C=C3OC2=C1 JJPPFLGOODJQBO-LBPRGKRZSA-N 0.000 description 1
- WTKYBFQVZPCGAO-LURJTMIESA-N (2s)-2-(pyridin-3-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CN=C1 WTKYBFQVZPCGAO-LURJTMIESA-N 0.000 description 1
- HLORENITWPXINR-CVRLYYSRSA-N (2s)-2-[2-[4-(3-hydroxypropyl)phenyl]ethyl]-4-methylpentanedioic acid Chemical compound OC(=O)C(C)C[C@@H](C(O)=O)CCC1=CC=C(CCCO)C=C1 HLORENITWPXINR-CVRLYYSRSA-N 0.000 description 1
- PGXLAZACGSXLAI-VWLOTQADSA-N (2s)-2-[[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)CC1 PGXLAZACGSXLAI-VWLOTQADSA-N 0.000 description 1
- NPDBDJFLKKQMCM-SCSAIBSYSA-N (2s)-2-amino-3,3-dimethylbutanoic acid Chemical compound CC(C)(C)[C@H](N)C(O)=O NPDBDJFLKKQMCM-SCSAIBSYSA-N 0.000 description 1
- MCBFGLOCAYSWIG-IBGZPJMESA-N (2s)-4-dibenzofuran-2-yl-2-(octanoylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C3=CC(C(=O)C[C@H](NC(=O)CCCCCCC)C(O)=O)=CC=C3OC2=C1 MCBFGLOCAYSWIG-IBGZPJMESA-N 0.000 description 1
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
- NTGUDLCGIIAOKV-VJBWXMMDSA-N (2s,4r)-2-butyl-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]-6-(4-propylphenyl)hexanoic acid Chemical compound C([C@H](C[C@H](CCCC)C(O)=O)C(=O)N1[C@@H](CCCN1)C(=O)NC)CC1=CC=C(CCC)C=C1 NTGUDLCGIIAOKV-VJBWXMMDSA-N 0.000 description 1
- NMQRDRTWRRRJMA-QTEQDKRBSA-N (2s,4r)-2-butyl-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]-6-[2-(1,3-oxazol-4-yl)phenyl]hexanoic acid Chemical compound C([C@H](C[C@H](CCCC)C(O)=O)C(=O)N1[C@@H](CCCN1)C(=O)NC)CC1=CC=CC=C1C1=COC=N1 NMQRDRTWRRRJMA-QTEQDKRBSA-N 0.000 description 1
- AJJNPAOFABBBSQ-QTEQDKRBSA-N (2s,4r)-2-butyl-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]-6-[2-(1,3-thiazol-4-yl)phenyl]hexanoic acid Chemical compound C([C@H](C[C@H](CCCC)C(O)=O)C(=O)N1[C@@H](CCCN1)C(=O)NC)CC1=CC=CC=C1C1=CSC=N1 AJJNPAOFABBBSQ-QTEQDKRBSA-N 0.000 description 1
- SQFAZTXLSZLFHF-SGNDLWITSA-N (2s,4r)-2-butyl-6-(4-butylphenyl)-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]hexanoic acid Chemical compound C([C@H](C[C@H](CCCC)C(O)=O)C(=O)N1[C@@H](CCCN1)C(=O)NC)CC1=CC=C(CCCC)C=C1 SQFAZTXLSZLFHF-SGNDLWITSA-N 0.000 description 1
- WQIFYYWGPPXAEB-GIWBLDEGSA-N (2s,4r)-2-butyl-6-(4-tert-butylphenyl)-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]hexanoic acid Chemical compound C([C@H](C[C@H](CCCC)C(O)=O)C(=O)N1[C@@H](CCCN1)C(=O)NC)CC1=CC=C(C(C)(C)C)C=C1 WQIFYYWGPPXAEB-GIWBLDEGSA-N 0.000 description 1
- PEBSIVPSJFEBIH-QTEQDKRBSA-N (2s,4r)-2-butyl-6-[2-(1h-imidazol-5-yl)phenyl]-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]hexanoic acid Chemical compound C([C@H](C[C@H](CCCC)C(O)=O)C(=O)N1[C@@H](CCCN1)C(=O)NC)CC1=CC=CC=C1C1=CN=CN1 PEBSIVPSJFEBIH-QTEQDKRBSA-N 0.000 description 1
- AUQXIHYGFLFQJD-USZFVNFHSA-N (2s,4r)-2-butyl-6-[4-(4-fluorophenyl)phenyl]-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]hexanoic acid Chemical compound C([C@H](C[C@H](CCCC)C(O)=O)C(=O)N1[C@@H](CCCN1)C(=O)NC)CC(C=C1)=CC=C1C1=CC=C(F)C=C1 AUQXIHYGFLFQJD-USZFVNFHSA-N 0.000 description 1
- KUGJOAKBWCLXEE-VPWXQRGCSA-N (2s,4r)-2-methyl-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]-6-[2-(1,3-oxazol-4-yl)phenyl]hexanoic acid Chemical compound CNC(=O)[C@@H]1CCCNN1C(=O)[C@@H](C[C@H](C)C(O)=O)CCC1=CC=CC=C1C1=COC=N1 KUGJOAKBWCLXEE-VPWXQRGCSA-N 0.000 description 1
- PRPWIDNKXWHYGQ-VPWXQRGCSA-N (2s,4r)-2-methyl-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]-6-[2-(1,3-thiazol-4-yl)phenyl]hexanoic acid Chemical compound CNC(=O)[C@@H]1CCCNN1C(=O)[C@@H](C[C@H](C)C(O)=O)CCC1=CC=CC=C1C1=CSC=N1 PRPWIDNKXWHYGQ-VPWXQRGCSA-N 0.000 description 1
- XPFPAABSECIGSG-QQNWGBJXSA-N (2s,4r)-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]-2-(3-phenylpropyl)-6-[2-(1,3-thiazol-4-yl)phenyl]hexanoic acid Chemical compound CNC(=O)[C@@H]1CCCNN1C(=O)[C@@H](C[C@H](CCCC=1C=CC=CC=1)C(O)=O)CCC1=CC=CC=C1C1=CSC=N1 XPFPAABSECIGSG-QQNWGBJXSA-N 0.000 description 1
- NNHGBKOOUBDMGL-VPWXQRGCSA-N (2s,4r)-6-[2-(1h-imidazol-5-yl)phenyl]-2-methyl-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]hexanoic acid Chemical compound CNC(=O)[C@@H]1CCCNN1C(=O)[C@@H](C[C@H](C)C(O)=O)CCC1=CC=CC=C1C1=CN=CN1 NNHGBKOOUBDMGL-VPWXQRGCSA-N 0.000 description 1
- ZUKJSHRYSDDETJ-LXBDKUERSA-N (2s,4r)-6-[4-(4-fluorophenyl)phenyl]-2-methyl-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]hexanoic acid Chemical compound CNC(=O)[C@@H]1CCCNN1C(=O)[C@@H](C[C@H](C)C(O)=O)CCC1=CC=C(C=2C=CC(F)=CC=2)C=C1 ZUKJSHRYSDDETJ-LXBDKUERSA-N 0.000 description 1
- DBWVBKROPMXJCV-PKTNWEFCSA-N (2s,4r)-6-[4-[(dimethylamino)methyl]phenyl]-4-[(6s)-6-(methylcarbamoyl)diazinane-1-carbonyl]-2-(3-phenylpropyl)hexanoic acid Chemical compound CNC(=O)[C@@H]1CCCNN1C(=O)[C@@H](C[C@H](CCCC=1C=CC=CC=1)C(O)=O)CCC1=CC=C(CN(C)C)C=C1 DBWVBKROPMXJCV-PKTNWEFCSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- PQTBEOWWLSYOIX-WUFLDLQOSA-N (3s)-2-[(2r)-2-[1-(hydroxyamino)-1-oxo-5-phenylpentan-2-yl]nonanoyl]-n-(2,2,6,6-tetramethylpiperidin-4-yl)diazinane-3-carboxamide Chemical compound ONC(=O)C([C@@H](CCCCCCC)C(=O)N1[C@@H](CCCN1)C(=O)NC1CC(C)(C)NC(C)(C)C1)CCCC1=CC=CC=C1 PQTBEOWWLSYOIX-WUFLDLQOSA-N 0.000 description 1
- FXPAVRINCIUVML-OEBVTXOESA-N (3s)-n-cyclohexyl-2-[(2r)-2-[1-(hydroxyamino)-1-oxo-5-phenylpentan-2-yl]nonanoyl]diazinane-3-carboxamide Chemical compound ONC(=O)C([C@@H](CCCCCCC)C(=O)N1[C@@H](CCCN1)C(=O)NC1CCCCC1)CCCC1=CC=CC=C1 FXPAVRINCIUVML-OEBVTXOESA-N 0.000 description 1
- QTIGZMMLNFOOJQ-PKHIMPSTSA-N (4-amino-1,3-dioxoisoindol-2-yl)methyl-[4-methyl-2-[[(2s)-4-methyl-1-(methylamino)-1-oxopentan-2-yl]carbamoyl]pentyl]phosphinic acid Chemical compound C1=CC(N)=C2C(=O)N(CP(O)(=O)CC(CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NC)C(=O)C2=C1 QTIGZMMLNFOOJQ-PKHIMPSTSA-N 0.000 description 1
- KJTLQQUUPVSXIM-ZCFIWIBFSA-M (R)-mevalonate Chemical compound OCC[C@](O)(C)CC([O-])=O KJTLQQUUPVSXIM-ZCFIWIBFSA-M 0.000 description 1
- 125000004747 1,1-dimethylethoxycarbonyl group Chemical group CC(C)(OC(=O)*)C 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- OTFKRHOATUETFR-UHFFFAOYSA-N 1-(4-phenylpiperazin-1-yl)propan-1-one Chemical compound C1CN(C(=O)CC)CCN1C1=CC=CC=C1 OTFKRHOATUETFR-UHFFFAOYSA-N 0.000 description 1
- LZGWJYFOISWDMK-UHFFFAOYSA-N 1-(dibenzofuran-2-ylsulfonylamino)cyclopropane-1-carboxylic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC1(C(=O)O)CC1 LZGWJYFOISWDMK-UHFFFAOYSA-N 0.000 description 1
- PDLGREGRADYARF-UHFFFAOYSA-N 1-amino-2-(hydroxymethyl)propane-1,3-diol Chemical compound NC(O)C(CO)CO PDLGREGRADYARF-UHFFFAOYSA-N 0.000 description 1
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 1
- RUYZJEIKQYLEGZ-UHFFFAOYSA-N 1-fluoro-4-phenylbenzene Chemical group C1=CC(F)=CC=C1C1=CC=CC=C1 RUYZJEIKQYLEGZ-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- SWZKXIPDGAAYKE-UHFFFAOYSA-N 1-morpholin-4-ylpropan-2-amine Chemical compound CC(N)CN1CCOCC1 SWZKXIPDGAAYKE-UHFFFAOYSA-N 0.000 description 1
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 1
- UCOSRTUSVXHIMK-UHFFFAOYSA-N 1h-benzimidazol-2-ylmethanamine Chemical compound C1=CC=C2NC(CN)=NC2=C1 UCOSRTUSVXHIMK-UHFFFAOYSA-N 0.000 description 1
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical group O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
- ITFDYXKCBZEBDG-UHFFFAOYSA-N 2-(1-methylpyrrol-2-yl)ethanamine Chemical compound CN1C=CC=C1CCN ITFDYXKCBZEBDG-UHFFFAOYSA-N 0.000 description 1
- RUZFOVWVTZFBEY-UHFFFAOYSA-N 2-(2-dibenzofuran-2-yl-2-hydroxyiminoethyl)-4-methylpentanoic acid Chemical compound C1=CC=C2C3=CC(C(=NO)CC(CC(C)C)C(O)=O)=CC=C3OC2=C1 RUZFOVWVTZFBEY-UHFFFAOYSA-N 0.000 description 1
- HDBJBHBTWZQDCD-UHFFFAOYSA-N 2-(2-dibenzofuran-2-yl-2-hydroxyiminoethyl)-5-(4-fluorophenyl)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1C(=NO)CC(C(O)=O)CCCC1=CC=C(F)C=C1 HDBJBHBTWZQDCD-UHFFFAOYSA-N 0.000 description 1
- SJPIHNMYAACOJG-UHFFFAOYSA-N 2-(2-dibenzofuran-2-yl-2-hydroxyiminoethyl)-5-(4-methoxyphenyl)pentanoic acid Chemical compound C1=CC(OC)=CC=C1CCCC(C(O)=O)CC(=NO)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 SJPIHNMYAACOJG-UHFFFAOYSA-N 0.000 description 1
- FYAJIJFVPRYYKV-UHFFFAOYSA-N 2-(2-dibenzofuran-2-yl-2-hydroxyiminoethyl)-5-phenylpentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1C(=NO)CC(C(O)=O)CCCC1=CC=CC=C1 FYAJIJFVPRYYKV-UHFFFAOYSA-N 0.000 description 1
- TUOZACADWRCCNC-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-2-(4-methoxyphenyl)acetic acid Chemical compound C1=CC(OC)=CC=C1C(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 TUOZACADWRCCNC-UHFFFAOYSA-N 0.000 description 1
- JENZVHXFRQGOFL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-2-phenylacetic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)C1=CC=CC=C1 JENZVHXFRQGOFL-UHFFFAOYSA-N 0.000 description 1
- QPCALSWJZUJWLK-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-(1h-imidazol-5-yl)propanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CC1=CNC=N1 QPCALSWJZUJWLK-UHFFFAOYSA-N 0.000 description 1
- SJPXJSANXSAHSU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-(4-fluorophenyl)propanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CC1=CC=C(F)C=C1 SJPXJSANXSAHSU-UHFFFAOYSA-N 0.000 description 1
- QUKJSCLIIFHJOF-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-(4-phenylmethoxyphenyl)propanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CC(C=C1)=CC=C1OCC1=CC=CC=C1 QUKJSCLIIFHJOF-UHFFFAOYSA-N 0.000 description 1
- COJSFTGHLOFDLF-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic acid Chemical compound C1=CC(OC(C)(C)C)=CC=C1CC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 COJSFTGHLOFDLF-UHFFFAOYSA-N 0.000 description 1
- UFYNTEKFUSRPMK-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-hydroxypropanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CO)C(O)=O)=CC=C3OC2=C1 UFYNTEKFUSRPMK-UHFFFAOYSA-N 0.000 description 1
- SDUOASNEYVEUJP-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-phenylmethoxypropanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)COCC1=CC=CC=C1 SDUOASNEYVEUJP-UHFFFAOYSA-N 0.000 description 1
- NOYWCELMDAGFET-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-4-sulfanylbutanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCS)C(=O)O)=CC=C3OC2=C1 NOYWCELMDAGFET-UHFFFAOYSA-N 0.000 description 1
- DMQDCKWVHYQISX-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCNC(=O)OCC1=CC=CC=C1 DMQDCKWVHYQISX-UHFFFAOYSA-N 0.000 description 1
- CPAXWZYVQBSDOD-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)OCC1=CC=CC=C1 CPAXWZYVQBSDOD-UHFFFAOYSA-N 0.000 description 1
- MPEIORQQCYVONP-UHFFFAOYSA-N 2-(heptanoylamino)butanoic acid Chemical compound CCCCCCC(=O)NC(CC)C(O)=O MPEIORQQCYVONP-UHFFFAOYSA-N 0.000 description 1
- OWLKLJCJVGNTAW-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-2-oxoethyl]-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)CC(=O)C1=CC=C(Cl)C=C1 OWLKLJCJVGNTAW-UHFFFAOYSA-N 0.000 description 1
- SJCPIQJOCMVHBA-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenyl)phenyl]-2-hydroxyethyl]-4-methylpentanoic acid Chemical compound C1=CC(C(O)CC(CC(C)C)C(O)=O)=CC=C1C1=CC=C(Cl)C=C1 SJCPIQJOCMVHBA-UHFFFAOYSA-N 0.000 description 1
- ACTQLAONUVECDR-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenyl)phenyl]-2-hydroxyiminoethyl]-2-fluoro-6-phenylhexanoic acid Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(=NO)CC(F)(C(O)=O)CCCCC1=CC=CC=C1 ACTQLAONUVECDR-UHFFFAOYSA-N 0.000 description 1
- UXRQPYBOLVQYQD-UHFFFAOYSA-N 2-[2-methylpropyl-[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]acetic acid Chemical class C1=CC(S(=O)(=O)N(CC(O)=O)CC(C)C)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 UXRQPYBOLVQYQD-UHFFFAOYSA-N 0.000 description 1
- MTRJGVMFMHSBCX-UHFFFAOYSA-N 2-[[2-[[4-(4-bromophenyl)phenyl]sulfonylamino]acetyl]amino]-6-phenylhexanoic acid Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)S(=O)(=O)NCC(=O)NC(C(=O)O)CCCCC1=CC=CC=C1 MTRJGVMFMHSBCX-UHFFFAOYSA-N 0.000 description 1
- MEOHTIBKCWWFRM-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(2-methylpropoxycarbonylamino)hexanoic acid Chemical compound C1=CC(S(=O)(=O)NC(CCCCNC(=O)OCC(C)C)C(O)=O)=CC=C1C1=CC=C(Br)C=C1 MEOHTIBKCWWFRM-UHFFFAOYSA-N 0.000 description 1
- VFLNACNIZOYMQK-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(2-phenoxybutanoylamino)hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(O)=O)CCCCNC(=O)C(CC)OC1=CC=CC=C1 VFLNACNIZOYMQK-UHFFFAOYSA-N 0.000 description 1
- JRPGFSSCBLWDMU-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(2-phenylethenylsulfonylamino)hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNS(=O)(=O)C=CC1=CC=CC=C1 JRPGFSSCBLWDMU-UHFFFAOYSA-N 0.000 description 1
- ZYCHFPRCALZWEG-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(3-phenylprop-2-enoylamino)hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)C=CC1=CC=CC=C1 ZYCHFPRCALZWEG-UHFFFAOYSA-N 0.000 description 1
- JBXVKSCRNTWNDQ-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(4-phenylbutanoylamino)hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCCC1=CC=CC=C1 JBXVKSCRNTWNDQ-UHFFFAOYSA-N 0.000 description 1
- JQAGVCGXDHYBPP-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(4-thiophen-2-ylbutanoylamino)hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCCC1=CC=CS1 JQAGVCGXDHYBPP-UHFFFAOYSA-N 0.000 description 1
- LNTCNQRVHFQNPD-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(6-phenylhexanoylamino)hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCCCCC1=CC=CC=C1 LNTCNQRVHFQNPD-UHFFFAOYSA-N 0.000 description 1
- DBXQAOWUJZDGHG-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(7-phenylheptanoylamino)hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCCCCCC1=CC=CC=C1 DBXQAOWUJZDGHG-UHFFFAOYSA-N 0.000 description 1
- FKNSXHLHWUDZGZ-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(naphthalen-1-ylsulfonylamino)hexanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)NCCCCC(C(=O)O)NS(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Br)C=C1 FKNSXHLHWUDZGZ-UHFFFAOYSA-N 0.000 description 1
- UZRHUJZRSKTUCF-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(naphthalen-2-ylsulfonylamino)hexanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)NCCCCC(C(=O)O)NS(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Br)C=C1 UZRHUJZRSKTUCF-UHFFFAOYSA-N 0.000 description 1
- RHNDFMCTIVLGNU-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-(pentylsulfonylamino)hexanoic acid Chemical compound C1=CC(S(=O)(=O)NC(CCCCNS(=O)(=O)CCCCC)C(O)=O)=CC=C1C1=CC=C(Br)C=C1 RHNDFMCTIVLGNU-UHFFFAOYSA-N 0.000 description 1
- HUZVKTZXGMIXHI-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(2-phenoxyacetyl)amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)COC1=CC=CC=C1 HUZVKTZXGMIXHI-UHFFFAOYSA-N 0.000 description 1
- WDYYQYASJAXGNZ-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(2-phenylsulfanylacetyl)amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CSC1=CC=CC=C1 WDYYQYASJAXGNZ-UHFFFAOYSA-N 0.000 description 1
- VSINVXYMZZGHSR-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(2-pyridin-4-ylsulfanylacetyl)amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CSC1=CC=NC=C1 VSINVXYMZZGHSR-UHFFFAOYSA-N 0.000 description 1
- ZBNKGFPVBNPNHG-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(2-thiophen-2-ylacetyl)amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CS1 ZBNKGFPVBNPNHG-UHFFFAOYSA-N 0.000 description 1
- JTSNKVXAGWTTQL-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(4-bromophenyl)sulfonylamino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNS(=O)(=O)C1=CC=C(Br)C=C1 JTSNKVXAGWTTQL-UHFFFAOYSA-N 0.000 description 1
- ICJJXTKALACFIO-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(4-fluorophenyl)sulfonylamino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNS(=O)(=O)C1=CC=C(F)C=C1 ICJJXTKALACFIO-UHFFFAOYSA-N 0.000 description 1
- NVRZZLBQPPYVGP-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[(4-methoxyphenyl)sulfonylamino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 NVRZZLBQPPYVGP-UHFFFAOYSA-N 0.000 description 1
- IHQHZDHUABWQAP-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[3-(4-chlorophenyl)propanoylamino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCC1=CC=C(Cl)C=C1 IHQHZDHUABWQAP-UHFFFAOYSA-N 0.000 description 1
- VANLASLGRAWOAL-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[[2,4,6-tri(propan-2-yl)benzoyl]amino]hexanoic acid Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 VANLASLGRAWOAL-UHFFFAOYSA-N 0.000 description 1
- VEEKBYDZLWFBLA-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[[2-(2,4-dichlorophenoxy)acetyl]amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)COC1=CC=C(Cl)C=C1Cl VEEKBYDZLWFBLA-UHFFFAOYSA-N 0.000 description 1
- LXDNQRMWUMGTNW-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[[2-(3,4-dimethoxyphenyl)acetyl]amino]hexanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 LXDNQRMWUMGTNW-UHFFFAOYSA-N 0.000 description 1
- YYUNOKHFOONFCA-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[[2-(4-chlorophenoxy)acetyl]amino]hexanoic acid Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)COC1=CC=C(Cl)C=C1 YYUNOKHFOONFCA-UHFFFAOYSA-N 0.000 description 1
- YCJXGDWGYODKOA-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-6-[[2-(4-methoxyphenoxy)acetyl]amino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1OCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 YCJXGDWGYODKOA-UHFFFAOYSA-N 0.000 description 1
- SQTBYARBJNHGQJ-UHFFFAOYSA-N 2-[[4-(4-phenylpiperazin-1-yl)phenyl]sulfonylamino]acetic acid Chemical compound C1=CC(S(=O)(=O)NCC(=O)O)=CC=C1N1CCN(C=2C=CC=CC=2)CC1 SQTBYARBJNHGQJ-UHFFFAOYSA-N 0.000 description 1
- BNOKHOUVRPYUSP-UHFFFAOYSA-N 2-[benzyl(octylsulfonyl)amino]-n-hydroxyacetamide Chemical compound CCCCCCCCS(=O)(=O)N(CC(=O)NO)CC1=CC=CC=C1 BNOKHOUVRPYUSP-UHFFFAOYSA-N 0.000 description 1
- VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 1
- ZKMLNPOVUPBBCF-UHFFFAOYSA-N 2-[decyl-(4-methylphenyl)sulfonylamino]-n-hydroxyacetamide Chemical compound CCCCCCCCCCN(CC(=O)NO)S(=O)(=O)C1=CC=C(C)C=C1 ZKMLNPOVUPBBCF-UHFFFAOYSA-N 0.000 description 1
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 description 1
- FZUBHJJEYNHYFU-DKWTVANSSA-N 2-aminoacetic acid;(2s)-2,4-diamino-4-oxobutanoic acid Chemical compound NCC(O)=O.OC(=O)[C@@H](N)CC(N)=O FZUBHJJEYNHYFU-DKWTVANSSA-N 0.000 description 1
- VDFRQZSFJVSJQY-WCCKRBBISA-N 2-aminoacetic acid;(2s)-2,5-diaminopentanoic acid Chemical compound NCC(O)=O.NCCC[C@H](N)C(O)=O VDFRQZSFJVSJQY-WCCKRBBISA-N 0.000 description 1
- BKKWZCSSYWYNDS-JEDNCBNOSA-N 2-aminoacetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCC(O)=O.NCCCC[C@H](N)C(O)=O BKKWZCSSYWYNDS-JEDNCBNOSA-N 0.000 description 1
- QPYGLMKJCFDDKV-FJXQXJEOSA-N 2-aminoacetic acid;(2s)-2-amino-2-phenylacetic acid Chemical compound NCC(O)=O.OC(=O)[C@@H](N)C1=CC=CC=C1 QPYGLMKJCFDDKV-FJXQXJEOSA-N 0.000 description 1
- HVBRJSWZFSWZKB-FVGYRXGTSA-N 2-aminoacetic acid;(2s)-2-amino-3-(1h-indol-3-yl)propanoic acid Chemical compound NCC(O)=O.C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 HVBRJSWZFSWZKB-FVGYRXGTSA-N 0.000 description 1
- FCWAUFMDOCOONS-QRPNPIFTSA-N 2-aminoacetic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid Chemical compound NCC(O)=O.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 FCWAUFMDOCOONS-QRPNPIFTSA-N 0.000 description 1
- ZVEUWSJUXREOBK-DKWTVANSSA-N 2-aminoacetic acid;(2s)-2-amino-3-hydroxypropanoic acid Chemical compound NCC(O)=O.OC[C@H](N)C(O)=O ZVEUWSJUXREOBK-DKWTVANSSA-N 0.000 description 1
- NYOGGQBMEGUVIX-WCCKRBBISA-N 2-aminoacetic acid;(2s)-2-amino-3-methylbutanoic acid Chemical compound NCC(O)=O.CC(C)[C@H](N)C(O)=O NYOGGQBMEGUVIX-WCCKRBBISA-N 0.000 description 1
- DQSIXGDDUJJEQH-QRPNPIFTSA-N 2-aminoacetic acid;(2s)-2-amino-3-phenylpropanoic acid Chemical compound NCC(O)=O.OC(=O)[C@@H](N)CC1=CC=CC=C1 DQSIXGDDUJJEQH-QRPNPIFTSA-N 0.000 description 1
- LTDYEDCDJFHPFI-DKWTVANSSA-N 2-aminoacetic acid;(2s)-2-aminopropanoic acid Chemical compound NCC(O)=O.C[C@H](N)C(O)=O LTDYEDCDJFHPFI-DKWTVANSSA-N 0.000 description 1
- XGKCWNGHLZXLTK-MUWMCQJSSA-N 2-aminoacetic acid;(2s,3r)-2-amino-3-hydroxybutanoic acid Chemical compound NCC(O)=O.C[C@@H](O)[C@H](N)C(O)=O XGKCWNGHLZXLTK-MUWMCQJSSA-N 0.000 description 1
- MNQVNFIVCSQNGY-FHAQVOQBSA-N 2-aminoacetic acid;(2s,3s)-2-amino-3-methylpentanoic acid Chemical compound NCC(O)=O.CC[C@H](C)[C@H](N)C(O)=O MNQVNFIVCSQNGY-FHAQVOQBSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- AWZLXVAPLHUDSY-UHFFFAOYSA-N 2-ethyl-1-methylpiperazine Chemical compound CCC1CNCCN1C AWZLXVAPLHUDSY-UHFFFAOYSA-N 0.000 description 1
- 102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SEINETSKRAZANU-UHFFFAOYSA-N 2-methylsulfanyl-1h-indole Chemical compound C1=CC=C2NC(SC)=CC2=C1 SEINETSKRAZANU-UHFFFAOYSA-N 0.000 description 1
- MIIIXQJBDGSIKL-UHFFFAOYSA-N 2-morpholin-4-ylethanesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)CCN1CCOCC1 MIIIXQJBDGSIKL-UHFFFAOYSA-N 0.000 description 1
- QEJTYZRPRCPARS-UHFFFAOYSA-N 2-propylbutanediamide Chemical compound CCCC(C(N)=O)CC(N)=O QEJTYZRPRCPARS-UHFFFAOYSA-N 0.000 description 1
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- QITHUWZVKZAWGW-UHFFFAOYSA-N 3-(1,3-dihydroisoindol-2-yl)butanoic acid Chemical compound C1=CC=C2CN(C(CC(O)=O)C)CC2=C1 QITHUWZVKZAWGW-UHFFFAOYSA-N 0.000 description 1
- CLUFNZTWUVTPGT-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(dibenzofuran-2-ylsulfonylamino)propanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CC1=CC=C(Cl)C=C1 CLUFNZTWUVTPGT-UHFFFAOYSA-N 0.000 description 1
- WWISHLRUOQVYLD-UHFFFAOYSA-N 3-(c-dibenzofuran-2-yl-n-hydroxycarbonimidoyl)-5-methylhexanoic acid Chemical compound C1=CC=C2C3=CC(C(=NO)C(CC(O)=O)CC(C)C)=CC=C3OC2=C1 WWISHLRUOQVYLD-UHFFFAOYSA-N 0.000 description 1
- XZIGLAWFTBSBMY-UHFFFAOYSA-N 3-(c-dibenzofuran-2-yl-n-hydroxycarbonimidoyl)-5-phenylpentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1C(=NO)C(CC(O)=O)CCC1=CC=CC=C1 XZIGLAWFTBSBMY-UHFFFAOYSA-N 0.000 description 1
- FTFHWIIEOHDQBV-UHFFFAOYSA-N 3-(c-dibenzofuran-2-yl-n-hydroxycarbonimidoyl)-6-(4-fluorophenyl)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1C(=NO)C(CC(O)=O)CCCC1=CC=C(F)C=C1 FTFHWIIEOHDQBV-UHFFFAOYSA-N 0.000 description 1
- OBVHTYKXSIHXDM-UHFFFAOYSA-N 3-(c-dibenzofuran-2-yl-n-hydroxycarbonimidoyl)-6-(4-methoxyphenyl)hexanoic acid Chemical compound C1=CC(OC)=CC=C1CCCC(CC(O)=O)C(=NO)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 OBVHTYKXSIHXDM-UHFFFAOYSA-N 0.000 description 1
- IHWRMEDAWMDWND-UHFFFAOYSA-N 3-(c-dibenzofuran-2-yl-n-hydroxycarbonimidoyl)-6-(4-methylphenyl)hexanoic acid Chemical compound C1=CC(C)=CC=C1CCCC(CC(O)=O)C(=NO)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 IHWRMEDAWMDWND-UHFFFAOYSA-N 0.000 description 1
- WXDHEKCNKUOATG-UHFFFAOYSA-N 3-[(3,4-dimethoxyphenyl)sulfonyl-[2-(hydroxyamino)-2-oxoethyl]amino]propanoic acid Chemical compound COC1=CC=C(S(=O)(=O)N(CCC(O)=O)CC(=O)NO)C=C1OC WXDHEKCNKUOATG-UHFFFAOYSA-N 0.000 description 1
- RDUOXXVFDHHAPP-UHFFFAOYSA-N 3-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C1=CC(S(=O)(=O)NCCC(=O)O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 RDUOXXVFDHHAPP-UHFFFAOYSA-N 0.000 description 1
- MFDBLXRLOJEAHS-UHFFFAOYSA-N 3-amino-1-(methoxymethyl)-3,4-dihydroquinolin-2-one Chemical compound NC1C(N(C2=CC=CC=C2C1)COC)=O MFDBLXRLOJEAHS-UHFFFAOYSA-N 0.000 description 1
- YYYANCULBDKRSC-UHFFFAOYSA-N 3-amino-3-(1-methoxyethoxymethyl)-1,4-dihydroquinolin-2-one Chemical compound NC1(C(NC2=CC=CC=C2C1)=O)COC(C)OC YYYANCULBDKRSC-UHFFFAOYSA-N 0.000 description 1
- ZZQNOJZLOXKABD-UHFFFAOYSA-N 3-amino-3-(1-methoxyethyl)-1,4-dihydroquinolin-2-one Chemical compound NC1(C(NC2=CC=CC=C2C1)=O)C(C)OC ZZQNOJZLOXKABD-UHFFFAOYSA-N 0.000 description 1
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 1
- IIJJEHHIFYIZAN-UHFFFAOYSA-N 3-chloro-2-(dibenzofuran-2-ylsulfonylamino)propanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCl)C(=O)O)=CC=C3OC2=C1 IIJJEHHIFYIZAN-UHFFFAOYSA-N 0.000 description 1
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 1
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- ZVQAMRMZOISPNF-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2,2-difluoro-4-hydroxyiminobutanoic acid Chemical compound C1=CC(C(CC(F)(F)C(O)=O)=NO)=CC=C1C1=CC=C(Cl)C=C1 ZVQAMRMZOISPNF-UHFFFAOYSA-N 0.000 description 1
- IRBKJJBJLGTLKN-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-3,3-difluoro-4-hydroxyiminobutanoic acid Chemical compound C1=CC(C(=NO)C(F)(F)CC(O)=O)=CC=C1C1=CC=C(Cl)C=C1 IRBKJJBJLGTLKN-UHFFFAOYSA-N 0.000 description 1
- RQJMLGGTENDEFM-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-4-hydroxyiminobutanoic acid Chemical compound C1=CC(C(CCC(O)=O)=NO)=CC=C1C1=CC=C(Cl)C=C1 RQJMLGGTENDEFM-UHFFFAOYSA-N 0.000 description 1
- BDFLUKICTBVNKJ-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=C(Cl)C=C1 BDFLUKICTBVNKJ-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- NCSLXBHBPUGLDK-UHFFFAOYSA-N 4-dibenzofuran-2-yl-4-hydroxyimino-2-(2-phenylethyl)butanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1C(=NO)CC(C(O)=O)CCC1=CC=CC=C1 NCSLXBHBPUGLDK-UHFFFAOYSA-N 0.000 description 1
- ODQJWIMYDRXPBG-UHFFFAOYSA-N 4-dibenzofuran-2-yl-4-hydroxyiminobutanoic acid Chemical compound C1=CC=C2C3=CC(C(CCC(O)=O)=NO)=CC=C3OC2=C1 ODQJWIMYDRXPBG-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- NTPKBGKSVCBASL-UHFFFAOYSA-N 4-hydroxyimino-4-[4-[4-(trifluoromethyl)phenyl]phenyl]butanoic acid Chemical compound C1=CC(C(CCC(O)=O)=NO)=CC=C1C1=CC=C(C(F)(F)F)C=C1 NTPKBGKSVCBASL-UHFFFAOYSA-N 0.000 description 1
- ZOKJAOHTJOEFEC-UHFFFAOYSA-N 4-isoindol-2-ylbutanoic acid Chemical compound C1=CC=CC2=CN(CCCC(=O)O)C=C21 ZOKJAOHTJOEFEC-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- PBTTWSCESNIZPN-UHFFFAOYSA-N 4-oxo-4-[4-[4-(pentanoylamino)phenyl]phenyl]-2-(2-phenylethyl)butanoic acid Chemical compound C1=CC(NC(=O)CCCC)=CC=C1C1=CC=C(C(=O)CC(CCC=2C=CC=CC=2)C(O)=O)C=C1 PBTTWSCESNIZPN-UHFFFAOYSA-N 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- CZDKQKOAHAICSF-JSAMMMMSSA-N 4beta-hydroxycholesterol Chemical compound C1C=C2[C@@H](O)[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 CZDKQKOAHAICSF-JSAMMMMSSA-N 0.000 description 1
- YHKUPPYODIHLRV-UHFFFAOYSA-N 5-nitro-2-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1S YHKUPPYODIHLRV-UHFFFAOYSA-N 0.000 description 1
- YIBZPVVKWIHFLM-UHFFFAOYSA-N 5-phenyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]pentanoic acid Chemical compound C=1C=C(N2CCC(CC2)C=2C=CC=CC=2)C=CC=1S(=O)(=O)NC(C(=O)O)CCCC1=CC=CC=C1 YIBZPVVKWIHFLM-UHFFFAOYSA-N 0.000 description 1
- HMPGIJYWBLUOLP-UHFFFAOYSA-N 6-(1-adamantyloxycarbonylamino)-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]hexanoic acid Chemical compound C1C(C2)CC(C3)CC2CC13OC(=O)NCCCCC(C(=O)O)NS(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Br)C=C1 HMPGIJYWBLUOLP-UHFFFAOYSA-N 0.000 description 1
- DXLFNVCVAVAXPH-UHFFFAOYSA-N 6-[(2-acetamido-1,3-thiazol-5-yl)sulfonylamino]-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]hexanoic acid Chemical compound S1C(NC(=O)C)=NC=C1S(=O)(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 DXLFNVCVAVAXPH-UHFFFAOYSA-N 0.000 description 1
- PDDOKSGSYBRHKK-UHFFFAOYSA-N 6-[(4-acetamidophenyl)sulfonylamino]-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]hexanoic acid Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(C=2C=CC(Br)=CC=2)C=C1 PDDOKSGSYBRHKK-UHFFFAOYSA-N 0.000 description 1
- HTAPCROOMANAQD-UHFFFAOYSA-N 6-isoindol-2-ylhexanoic acid Chemical compound C1=CC=CC2=CN(CCCCCC(=O)O)C=C21 HTAPCROOMANAQD-UHFFFAOYSA-N 0.000 description 1
- 101710151806 72 kDa type IV collagenase Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 108010027006 Apolipoproteins B Proteins 0.000 description 1
- 102000018616 Apolipoproteins B Human genes 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SJXHTLCGNPINLR-GLMQBPPQSA-N C(=O)(O)[C@@H](C)OC(C1=CC=CC=C1)N[C@@](C1=CC=CC=C1)(C(=O)O)CCC Chemical compound C(=O)(O)[C@@H](C)OC(C1=CC=CC=C1)N[C@@](C1=CC=CC=C1)(C(=O)O)CCC SJXHTLCGNPINLR-GLMQBPPQSA-N 0.000 description 1
- GBJADNBEGCVFLZ-BBWFWOEESA-N C(CCCCCCC)[C@@H](C(=O)N1N[C@@H](CCC1)C(=O)NC)C[C@@H](C(=O)O)C Chemical compound C(CCCCCCC)[C@@H](C(=O)N1N[C@@H](CCC1)C(=O)NC)C[C@@H](C(=O)O)C GBJADNBEGCVFLZ-BBWFWOEESA-N 0.000 description 1
- LRIXQMXPAGKQHJ-YDALLXLXSA-N C1(=CC=CC2=CC=CC=C12)C[C@H](N)C(=O)O.NCC(=O)O Chemical compound C1(=CC=CC2=CC=CC=C12)C[C@H](N)C(=O)O.NCC(=O)O LRIXQMXPAGKQHJ-YDALLXLXSA-N 0.000 description 1
- BIEVKPKJUVQWOT-UHFFFAOYSA-N C1=CC(=CC(=C1)I)CCC(CC(=O)C2=CC=C(C=C2)C3=CC=C(C=C3)Cl)C(=O)O Chemical compound C1=CC(=CC(=C1)I)CCC(CC(=O)C2=CC=C(C=C2)C3=CC=C(C=C3)Cl)C(=O)O BIEVKPKJUVQWOT-UHFFFAOYSA-N 0.000 description 1
- OIDQLLOOFLRALV-UHFFFAOYSA-N C1=CC(OCCC)=CC=C1C1=CC=C(C(=O)CC(CCCC=2C=CC=CC=2)C(O)=O)C=C1 Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C(=O)CC(CCCC=2C=CC=CC=2)C(O)=O)C=C1 OIDQLLOOFLRALV-UHFFFAOYSA-N 0.000 description 1
- ADUNTANYGKFULY-UHFFFAOYSA-N C1=CC=C(C=C1)C2=CC(=C(C=C2)CCCC(=O)O)C3=CC=C(C=C3)C4=CC=C(C=C4)Cl Chemical compound C1=CC=C(C=C1)C2=CC(=C(C=C2)CCCC(=O)O)C3=CC=C(C=C3)C4=CC=C(C=C4)Cl ADUNTANYGKFULY-UHFFFAOYSA-N 0.000 description 1
- WOYGWFKBWDOKAA-UHFFFAOYSA-N C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(=NO)CC(F)(C(O)=O)CCC(=O)NCCC1=CC=CC=C1 Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(=NO)CC(F)(C(O)=O)CCC(=O)NCCC1=CC=CC=C1 WOYGWFKBWDOKAA-UHFFFAOYSA-N 0.000 description 1
- NJTAHIJXICWATI-UHFFFAOYSA-N CC(C)CC(CCC1=CC=C(C=C1)C2=CC=CC=C2)C(=O)O Chemical compound CC(C)CC(CCC1=CC=C(C=C1)C2=CC=CC=C2)C(=O)O NJTAHIJXICWATI-UHFFFAOYSA-N 0.000 description 1
- MJUKQLMRSKBSGY-UHFFFAOYSA-N CC1=C(C=CC(=C1)OCCCCNCCCCC(C(=O)O)NS(=O)(=O)C2=CC=C(C=C2)C3=CC=C(C=C3)Br)Cl Chemical compound CC1=C(C=CC(=C1)OCCCCNCCCCC(C(=O)O)NS(=O)(=O)C2=CC=C(C=C2)C3=CC=C(C=C3)Br)Cl MJUKQLMRSKBSGY-UHFFFAOYSA-N 0.000 description 1
- WRGFOZGFNPZYFZ-UHFFFAOYSA-N CCC(CC=NO)C(C(O)=O)=C(C1)C=CC2=C1C(C=CC=C1)=C1O2 Chemical compound CCC(CC=NO)C(C(O)=O)=C(C1)C=CC2=C1C(C=CC=C1)=C1O2 WRGFOZGFNPZYFZ-UHFFFAOYSA-N 0.000 description 1
- JNLWWPRXCVAFNW-UHFFFAOYSA-N CCC(CCCC1=CC=C(C=C1)Cl)C(=NO)C2=CC3=C(C=C2)OC4=CC=CC=C43 Chemical compound CCC(CCCC1=CC=C(C=C1)Cl)C(=NO)C2=CC3=C(C=C2)OC4=CC=CC=C43 JNLWWPRXCVAFNW-UHFFFAOYSA-N 0.000 description 1
- OQQONJSUWDBNPY-UHFFFAOYSA-N CCC(CCCC1=CC=CC=C1)C(=NO)C2=CC3=C(C=C2)OC4=CC=CC=C43 Chemical compound CCC(CCCC1=CC=CC=C1)C(=NO)C2=CC3=C(C=C2)OC4=CC=CC=C43 OQQONJSUWDBNPY-UHFFFAOYSA-N 0.000 description 1
- CLRZIEWUXVTEHB-UHFFFAOYSA-N CCC1=CC=C(C=C1)C2=CC=C(C=C2)CCC(CC(C)C)C(=O)O Chemical compound CCC1=CC=C(C=C1)C2=CC=C(C=C2)CCC(CC(C)C)C(=O)O CLRZIEWUXVTEHB-UHFFFAOYSA-N 0.000 description 1
- KQOLUHIIFZWZPN-QMMMGPOBSA-N CCCC(=O)NC(=O)[C@H](CC(C)C)N Chemical compound CCCC(=O)NC(=O)[C@H](CC(C)C)N KQOLUHIIFZWZPN-QMMMGPOBSA-N 0.000 description 1
- MDWHMPCYCAETKO-UHFFFAOYSA-N CCCC1=CCC(C=C1)(OC2=CC=CC=C2)S(=O)(=O)NCC(=O)NO Chemical compound CCCC1=CCC(C=C1)(OC2=CC=CC=C2)S(=O)(=O)NCC(=O)NO MDWHMPCYCAETKO-UHFFFAOYSA-N 0.000 description 1
- ZXSBGCGMVHHFIX-LJAQVGFWSA-N CCCCCCCCCCCC([C@@](CC(C(C=C1)=CC2=C1OC1=C2C=CC=C1)=O)(C(O)=O)NC(C(F)(F)F)=O)=O Chemical compound CCCCCCCCCCCC([C@@](CC(C(C=C1)=CC2=C1OC1=C2C=CC=C1)=O)(C(O)=O)NC(C(F)(F)F)=O)=O ZXSBGCGMVHHFIX-LJAQVGFWSA-N 0.000 description 1
- DOZWTRWNDCQFLA-UBFHEZILSA-N CSCCC(P(O)(O)=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=CC=C1 Chemical compound CSCCC(P(O)(O)=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=CC=C1 DOZWTRWNDCQFLA-UBFHEZILSA-N 0.000 description 1
- XUSTXZWFDRQYBE-QRWLVFNGSA-N C[C@H](CCN1C(=O)C2=CC3=CC=CC=C3C=C2C1=O)N[C@@H](CC(C)C)C(=O)NCC4=NC(=NN4)N Chemical compound C[C@H](CCN1C(=O)C2=CC3=CC=CC=C3C=C2C1=O)N[C@@H](CC(C)C)C(=O)NCC4=NC(=NN4)N XUSTXZWFDRQYBE-QRWLVFNGSA-N 0.000 description 1
- MCVRAVYDLNZUCY-ONEGZZNKSA-N C\C=C\CCC(C)C(O)=O Chemical compound C\C=C\CCC(C)C(O)=O MCVRAVYDLNZUCY-ONEGZZNKSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010071200 Carbohydrate intolerance Diseases 0.000 description 1
- 206010008479 Chest Pain Diseases 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 description 1
- 101100410079 Dictyostelium discoideum psrA gene Proteins 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- MTFCXMJOGMHYAE-UHFFFAOYSA-N Ethyl piperazinoacetate Chemical compound CCOC(=O)CN1CCNCC1 MTFCXMJOGMHYAE-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 206010026673 Malignant Pleural Effusion Diseases 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 1
- 108010076497 Matrix Metalloproteinase 10 Proteins 0.000 description 1
- 108010016165 Matrix Metalloproteinase 2 Proteins 0.000 description 1
- 108010016160 Matrix Metalloproteinase 3 Proteins 0.000 description 1
- 102000001776 Matrix metalloproteinase-9 Human genes 0.000 description 1
- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 101150101095 Mmp12 gene Proteins 0.000 description 1
- 108010030545 N-(2(R)-2-(hydroxamidocarbonylmethyl)-4-methylpentanoyl)-L-tryptophan methylamide Proteins 0.000 description 1
- IBZYLASMHDEERU-BCNZCGCRSA-N N-[(2S)-3-[1-[(2S)-2-amino-4-methylpentanoyl]cyclohexa-2,4-dien-1-yl]-1-(methylamino)-1-oxopropan-2-yl]-4-(1,3-dioxoisoindol-2-yl)-2-sulfanylbutanamide Chemical compound CNC([C@@H](NC(C(CCN1C(C=2C(C1=O)=CC=CC=2)=O)S)=O)CC1(CC=CC=C1)C([C@@H](N)CC(C)C)=O)=O IBZYLASMHDEERU-BCNZCGCRSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- HMNXCXBRSOBSLW-JEDNCBNOSA-N N[C@@H](CCCC)C(=O)O.NCC(=O)O Chemical compound N[C@@H](CCCC)C(=O)O.NCC(=O)O HMNXCXBRSOBSLW-JEDNCBNOSA-N 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 108030001564 Neutrophil collagenases Proteins 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLQDYWIDEVCIOV-UHFFFAOYSA-N OC(CNS(C(C=C1)=CCC1(C1=CC=CC=C1)N(CC1)CCC1C1=CC=CC=C1)(=O)=O)=O Chemical compound OC(CNS(C(C=C1)=CCC1(C1=CC=CC=C1)N(CC1)CCC1C1=CC=CC=C1)(=O)=O)=O ZLQDYWIDEVCIOV-UHFFFAOYSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 102000016387 Pancreatic elastase Human genes 0.000 description 1
- 108010067372 Pancreatic elastase Proteins 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102000016611 Proteoglycans Human genes 0.000 description 1
- 108010067787 Proteoglycans Proteins 0.000 description 1
- 229940123934 Reductase inhibitor Drugs 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 101710108790 Stromelysin-1 Proteins 0.000 description 1
- 102100028848 Stromelysin-2 Human genes 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010042434 Sudden death Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JJXQJRXVCKXJRM-NTZARQNWSA-N [1-[[(2s)-4-methyl-1-[[(2s)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-(phenylmethoxycarbonylamino)propyl]phosphonic acid Chemical compound C([C@@H](C(=O)NC)NC(=O)[C@H](CC(C)C)NC(CCNC(=O)OCC=1C=CC=CC=1)P(O)(O)=O)C1=CC=CC=C1 JJXQJRXVCKXJRM-NTZARQNWSA-N 0.000 description 1
- LDPMUHRCTWJLHO-FETUBVHVSA-N [1-[[(2s)-4-methyl-1-[[(2s)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-methylsulfinylpropyl]phosphonic acid Chemical compound CS(=O)CCC(P(O)(O)=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=CC=C1 LDPMUHRCTWJLHO-FETUBVHVSA-N 0.000 description 1
- QYTKSXGBSMQUIT-UBFHEZILSA-N [1-[[(2s)-4-methyl-1-[[(2s)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-methylsulfonylpropyl]phosphonic acid Chemical compound CS(=O)(=O)CCC(P(O)(O)=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC)CC1=CC=CC=C1 QYTKSXGBSMQUIT-UBFHEZILSA-N 0.000 description 1
- LYFTYDBNWKYIJK-OJSMNCEXSA-N [1-[[(2s)-4-methyl-1-[[(2s)-1-(methylamino)-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-phenylpropyl]phosphonic acid Chemical compound C([C@@H](C(=O)NC)NC(=O)[C@H](CC(C)C)NC(CCC=1C=CC=CC=1)P(O)(O)=O)C1=CC=CC=C1 LYFTYDBNWKYIJK-OJSMNCEXSA-N 0.000 description 1
- GNSLACGSDSJAIQ-UHFFFAOYSA-N [4-(4-phenyl-piperidin-1-yl)-benzenesulfonylamino]-acetic acid Chemical compound C1=CC(S(=O)(=O)NCC(=O)O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 GNSLACGSDSJAIQ-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229960001171 acetohydroxamic acid Drugs 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Natural products OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000003257 anti-anginal effect Effects 0.000 description 1
- 230000001315 anti-hyperlipaemic effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 210000001765 aortic valve Anatomy 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- SHZPNDRIDUBNMH-NIJVSVLQSA-L atorvastatin calcium trihydrate Chemical group O.O.O.[Ca+2].C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 SHZPNDRIDUBNMH-NIJVSVLQSA-L 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000012742 biochemical analysis Methods 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000005516 coenzyme A Substances 0.000 description 1
- 229940093530 coenzyme a Drugs 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 201000007717 corneal ulcer Diseases 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NGFQXYLWQODUIL-UHFFFAOYSA-N cyclohexylazanide Chemical compound [NH-]C1CCCCC1 NGFQXYLWQODUIL-UHFFFAOYSA-N 0.000 description 1
- 230000000093 cytochemical effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000002592 echocardiography Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000007446 glucose tolerance test Methods 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 108010015792 glycyllysine Proteins 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N hexanoic acid methyl ester Natural products CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002657 hormone replacement therapy Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
- 229960003827 isosorbide mononitrate Drugs 0.000 description 1
- 230000000366 juvenile effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 108010091798 leucylleucine Proteins 0.000 description 1
- 229940002661 lipitor Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 229950008959 marimastat Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- GXHMMDRXHUIUMN-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O GXHMMDRXHUIUMN-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- AXLHVTKGDPVANO-UHFFFAOYSA-N methyl 2-amino-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound COC(=O)C(N)CNC(=O)OC(C)(C)C AXLHVTKGDPVANO-UHFFFAOYSA-N 0.000 description 1
- BPGCKMCHSYSDJD-UHFFFAOYSA-N methyl 4-formamidobenzoate Chemical compound COC(=O)C1=CC=C(NC=O)C=C1 BPGCKMCHSYSDJD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007491 morphometric analysis Methods 0.000 description 1
- 230000003562 morphometric effect Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- WACQAUOWMWPNQS-UHFFFAOYSA-N n-hydroxy-2-[(4-methoxyphenyl)sulfonyl-nonylamino]acetamide Chemical compound CCCCCCCCCN(CC(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 WACQAUOWMWPNQS-UHFFFAOYSA-N 0.000 description 1
- XTZSTNYJRISMQA-UHFFFAOYSA-N n-hydroxy-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]acetamide Chemical compound C1=CC(S(=O)(=O)NCC(=O)NO)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 XTZSTNYJRISMQA-UHFFFAOYSA-N 0.000 description 1
- DKGQJJYMQYEUDM-UHFFFAOYSA-N n-hydroxy-2-[naphthalen-2-ylmethyl(octylsulfonyl)amino]acetamide Chemical compound C1=CC=CC2=CC(CN(CC(=O)NO)S(=O)(=O)CCCCCCCC)=CC=C21 DKGQJJYMQYEUDM-UHFFFAOYSA-N 0.000 description 1
- YARQTRUESJBNGG-UHFFFAOYSA-N n-hydroxy-5-methyl-3-[3-(methylamino)-3-oxopropyl]sulfinylhexanamide Chemical compound CNC(=O)CCS(=O)C(CC(C)C)CC(=O)NO YARQTRUESJBNGG-UHFFFAOYSA-N 0.000 description 1
- RGUVUPQQFXCJFC-UHFFFAOYSA-N n-hydroxyoctanamide Chemical compound CCCCCCCC(=O)NO RGUVUPQQFXCJFC-UHFFFAOYSA-N 0.000 description 1
- QJPFSIALJNAOIO-UHFFFAOYSA-N n-methyl-3,4-dihydro-2h-quinoxaline-1-carboxamide Chemical compound C1=CC=C2N(C(=O)NC)CCNC2=C1 QJPFSIALJNAOIO-UHFFFAOYSA-N 0.000 description 1
- HPYONZVIPMACEZ-UHFFFAOYSA-N n-methylpiperazine-1-carboxamide Chemical compound CNC(=O)N1CCNCC1 HPYONZVIPMACEZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960005141 piperazine Drugs 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960001495 pravastatin sodium Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 235000021076 total caloric intake Nutrition 0.000 description 1
- 239000006211 transdermal dosage form Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7826598P | 1998-03-17 | 1998-03-17 | |
| US60/078,265 | 1998-03-17 | ||
| PCT/US1998/024681 WO1999047138A1 (en) | 1998-03-17 | 1998-11-20 | Statin-matrix metalloproteinase inhibitor combinations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002506818A true JP2002506818A (ja) | 2002-03-05 |
| JP2002506818A5 JP2002506818A5 (enExample) | 2006-01-19 |
Family
ID=22142950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000536378A Pending JP2002506818A (ja) | 1998-03-17 | 1998-11-20 | スタチン−マトリックスメタロプロテイナーゼ阻害剤組み合わせ物 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1063991A1 (enExample) |
| JP (1) | JP2002506818A (enExample) |
| KR (1) | KR20010041916A (enExample) |
| AR (1) | AR018113A1 (enExample) |
| AU (1) | AU1591699A (enExample) |
| BR (1) | BR9815745A (enExample) |
| CA (1) | CA2309588A1 (enExample) |
| CO (1) | CO5070670A1 (enExample) |
| GT (1) | GT199900039A (enExample) |
| HN (1) | HN1999000029A (enExample) |
| MY (1) | MY140504A (enExample) |
| NZ (1) | NZ505994A (enExample) |
| PA (1) | PA8469001A1 (enExample) |
| PE (1) | PE20000348A1 (enExample) |
| SV (1) | SV1999000026A (enExample) |
| UY (1) | UY25436A1 (enExample) |
| WO (1) | WO1999047138A1 (enExample) |
| ZA (1) | ZA992106B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009514848A (ja) * | 2005-11-08 | 2009-04-09 | ランバクシー ラボラトリーズ リミテッド | 医薬組成物 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| GB0100761D0 (en) | 2001-01-11 | 2001-02-21 | Biocompatibles Ltd | Drug delivery from stents |
| AU2005315608B2 (en) | 2004-12-15 | 2011-03-31 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising NEP-inhibitors, inhibitors of the endogenous endothelin producing system and HMG CoA reductase inhibitors |
| WO2010005389A1 (en) * | 2008-07-11 | 2010-01-14 | Forskarpatent I Syd Ab | Oxidized ldl specific antibody-fusion and conjugated proteins |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1217656C (zh) * | 1995-11-02 | 2005-09-07 | 沃尼尔·朗伯公司 | 用于调节脂浓度的方法和药物组合物 |
| EP0901466B1 (en) * | 1996-05-17 | 2001-10-31 | Warner-Lambert Company | Biphenylsulfonamide matrix metalloproteinase inhibitors |
| NZ334897A (en) * | 1996-12-09 | 2001-02-23 | Warner Lambert Co | Medicaments for treating and preventing heart failure and ventricular dilatation |
| TW536540B (en) * | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| GT199800126A (es) * | 1997-08-29 | 2000-01-29 | Terapia de combinacion. |
-
1998
- 1998-11-20 KR KR1020007010223A patent/KR20010041916A/ko not_active Ceased
- 1998-11-20 EP EP98960279A patent/EP1063991A1/en not_active Withdrawn
- 1998-11-20 JP JP2000536378A patent/JP2002506818A/ja active Pending
- 1998-11-20 WO PCT/US1998/024681 patent/WO1999047138A1/en not_active Ceased
- 1998-11-20 AU AU15916/99A patent/AU1591699A/en not_active Abandoned
- 1998-11-20 NZ NZ505994A patent/NZ505994A/xx unknown
- 1998-11-20 BR BR9815745-0A patent/BR9815745A/pt not_active Application Discontinuation
- 1998-11-20 CA CA002309588A patent/CA2309588A1/en not_active Abandoned
-
1999
- 1999-02-24 AR ARP990100751A patent/AR018113A1/es unknown
- 1999-03-15 MY MYPI99000951A patent/MY140504A/en unknown
- 1999-03-16 CO CO99016109A patent/CO5070670A1/es unknown
- 1999-03-16 GT GT199900039A patent/GT199900039A/es unknown
- 1999-03-16 ZA ZA9902106A patent/ZA992106B/xx unknown
- 1999-03-16 UY UY25436A patent/UY25436A1/es not_active Application Discontinuation
- 1999-03-16 PA PA19998469001A patent/PA8469001A1/es unknown
- 1999-03-16 HN HN1999000029A patent/HN1999000029A/es unknown
- 1999-03-16 SV SV1999000026A patent/SV1999000026A/es not_active Application Discontinuation
- 1999-03-16 PE PE1999000217A patent/PE20000348A1/es not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009514848A (ja) * | 2005-11-08 | 2009-04-09 | ランバクシー ラボラトリーズ リミテッド | 医薬組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2309588A1 (en) | 1999-09-23 |
| EP1063991A1 (en) | 2001-01-03 |
| AR018113A1 (es) | 2001-10-31 |
| BR9815745A (pt) | 2000-11-14 |
| CO5070670A1 (es) | 2001-08-28 |
| NZ505994A (en) | 2003-10-31 |
| PE20000348A1 (es) | 2000-05-22 |
| HN1999000029A (es) | 1999-09-29 |
| AU1591699A (en) | 1999-10-11 |
| WO1999047138A1 (en) | 1999-09-23 |
| SV1999000026A (es) | 2000-01-18 |
| KR20010041916A (ko) | 2001-05-25 |
| GT199900039A (es) | 2000-09-06 |
| UY25436A1 (es) | 2001-10-25 |
| MY140504A (en) | 2009-12-31 |
| PA8469001A1 (es) | 2002-09-17 |
| ZA992106B (en) | 1999-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU741768B2 (en) | Method for treating and preventing heart failure and ventricular dilatation | |
| US6133304A (en) | ACE inhibitor-MMP inhibitor combinations | |
| US6340709B1 (en) | Use of matrix metalloproteinase inhibitors for treating neurological disorders and promoting wound healing | |
| JP2002521328A (ja) | アテローム性動脈硬化症病変の治療のためのacat阻害剤およびmmp阻害剤の併用投与 | |
| US20040176393A1 (en) | Statin-MMP inhibitor combinations | |
| JP2002506818A (ja) | スタチン−マトリックスメタロプロテイナーゼ阻害剤組み合わせ物 | |
| US20050020607A1 (en) | Statin-MMP inhibitor combinations | |
| AU2003248291A1 (en) | Statin-matrix metalloproteinase inhibitor combinations | |
| MXPA00005034A (en) | Statin-matrix metalloproteinase inhibitor combinations | |
| MXPA00003736A (en) | Ace inhibitor-mmp inhibitor combinations | |
| EP1366765A1 (en) | Use of matrix metalloproteinase inhibitors for treating neurological disorders and promoting wound healing | |
| MXPA01000780A (en) | Coadministration of acat and mmp inhibitors for the treatment of atherosclerotic lesions | |
| MXPA99002254A (en) | Use of matrix metalloproteinase inhibitors for treating neurological disorders and promoting wound healing |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20051117 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20051117 |
|
| A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20051117 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20051117 |
|
| A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20051214 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20060117 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20060414 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20060421 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060718 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20060822 |