TW200808315A - A novel composition for treating organ or tissue fibrosis comprising 5-methyl-1-(substituted phenyl)-2-(1H)pyridone - Google Patents
A novel composition for treating organ or tissue fibrosis comprising 5-methyl-1-(substituted phenyl)-2-(1H)pyridone Download PDFInfo
- Publication number
- TW200808315A TW200808315A TW095128659A TW95128659A TW200808315A TW 200808315 A TW200808315 A TW 200808315A TW 095128659 A TW095128659 A TW 095128659A TW 95128659 A TW95128659 A TW 95128659A TW 200808315 A TW200808315 A TW 200808315A
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- pyridone
- group
- flufenidone
- fibrosis
- Prior art date
Links
- 206010016654 Fibrosis Diseases 0.000 title claims abstract description 53
- 230000004761 fibrosis Effects 0.000 title claims abstract description 53
- -1 5-methyl-1-(substituted phenyl)-2-(1H)pyridone Chemical class 0.000 title claims abstract description 43
- 239000000203 mixture Substances 0.000 title claims abstract 7
- 210000000056 organ Anatomy 0.000 title claims description 36
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims abstract description 88
- 229960003073 pirfenidone Drugs 0.000 claims abstract description 84
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 27
- 230000003510 anti-fibrotic effect Effects 0.000 claims abstract description 12
- JDZYVVUJIQYGRX-UHFFFAOYSA-N 1-(3-fluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(F)=C1 JDZYVVUJIQYGRX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- 206010050207 Skin fibrosis Diseases 0.000 claims abstract 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 135
- 230000000694 effects Effects 0.000 claims description 68
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 claims description 60
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 60
- 241000700159 Rattus Species 0.000 claims description 58
- 210000001519 tissue Anatomy 0.000 claims description 58
- 210000004027 cell Anatomy 0.000 claims description 56
- 239000003814 drug Substances 0.000 claims description 51
- 229940079593 drug Drugs 0.000 claims description 46
- 230000035755 proliferation Effects 0.000 claims description 45
- 239000002609 medium Substances 0.000 claims description 35
- 210000002950 fibroblast Anatomy 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 238000002474 experimental method Methods 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 24
- 239000002689 soil Substances 0.000 claims description 24
- 150000002576 ketones Chemical class 0.000 claims description 23
- 210000002966 serum Anatomy 0.000 claims description 23
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 claims description 22
- 244000309466 calf Species 0.000 claims description 21
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 21
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 20
- 208000015181 infectious disease Diseases 0.000 claims description 19
- 210000004072 lung Anatomy 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 16
- 241001465754 Metazoa Species 0.000 claims description 16
- 241000699670 Mus sp. Species 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000006378 damage Effects 0.000 claims description 16
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 230000003176 fibrotic effect Effects 0.000 claims description 15
- 208000027418 Wounds and injury Diseases 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 208000014674 injury Diseases 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 201000004409 schistosomiasis Diseases 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 13
- 206010012601 diabetes mellitus Diseases 0.000 claims description 13
- 235000013601 eggs Nutrition 0.000 claims description 13
- 210000003584 mesangial cell Anatomy 0.000 claims description 13
- 241000699666 Mus <mouse, genus> Species 0.000 claims description 12
- 210000001054 cardiac fibroblast Anatomy 0.000 claims description 12
- 239000006285 cell suspension Substances 0.000 claims description 12
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 12
- 210000003734 kidney Anatomy 0.000 claims description 12
- 238000001356 surgical procedure Methods 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 210000003245 peritoneal mesothelial cell Anatomy 0.000 claims description 11
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 11
- 239000012679 serum free medium Substances 0.000 claims description 11
- 108010061435 Enalapril Proteins 0.000 claims description 10
- 102000014150 Interferons Human genes 0.000 claims description 10
- 108010050904 Interferons Proteins 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical group C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 claims description 10
- 229960000873 enalapril Drugs 0.000 claims description 10
- 229940079322 interferon Drugs 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 10
- 102000004127 Cytokines Human genes 0.000 claims description 9
- 108090000695 Cytokines Proteins 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 230000003902 lesion Effects 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 231100000241 scar Toxicity 0.000 claims description 9
- 231100000419 toxicity Toxicity 0.000 claims description 9
- 230000001988 toxicity Effects 0.000 claims description 9
- 239000004072 C09CA03 - Valsartan Substances 0.000 claims description 8
- 238000012449 Kunming mouse Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 210000004024 hepatic stellate cell Anatomy 0.000 claims description 8
- 210000004185 liver Anatomy 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical group C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 claims description 8
- 229960004699 valsartan Drugs 0.000 claims description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
- 238000010171 animal model Methods 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- 230000001434 glomerular Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 102000008186 Collagen Human genes 0.000 claims description 6
- 108010035532 Collagen Proteins 0.000 claims description 6
- 102000008070 Interferon-gamma Human genes 0.000 claims description 6
- 108010074328 Interferon-gamma Proteins 0.000 claims description 6
- 231100000403 acute toxicity Toxicity 0.000 claims description 6
- 230000007059 acute toxicity Effects 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 210000004369 blood Anatomy 0.000 claims description 6
- 239000008280 blood Substances 0.000 claims description 6
- 229920001436 collagen Polymers 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- VYKKDKFTDMVOBU-UHFFFAOYSA-N flusalan Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 VYKKDKFTDMVOBU-UHFFFAOYSA-N 0.000 claims description 6
- 229950004696 flusalan Drugs 0.000 claims description 6
- 229940044627 gamma-interferon Drugs 0.000 claims description 6
- 230000007246 mechanism Effects 0.000 claims description 6
- 210000004738 parenchymal cell Anatomy 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 claims description 5
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 claims description 5
- SOHMZGMHXUQHGE-UHFFFAOYSA-N 5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1 SOHMZGMHXUQHGE-UHFFFAOYSA-N 0.000 claims description 5
- 108010006654 Bleomycin Proteins 0.000 claims description 5
- 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 claims description 5
- 102000004887 Transforming Growth Factor beta Human genes 0.000 claims description 5
- 108090001012 Transforming Growth Factor beta Proteins 0.000 claims description 5
- 238000009825 accumulation Methods 0.000 claims description 5
- 230000002300 anti-fibrosis Effects 0.000 claims description 5
- 229960001561 bleomycin Drugs 0.000 claims description 5
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 claims description 5
- 230000037396 body weight Effects 0.000 claims description 5
- 230000004663 cell proliferation Effects 0.000 claims description 5
- 230000034994 death Effects 0.000 claims description 5
- 231100000517 death Toxicity 0.000 claims description 5
- 238000011161 development Methods 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 238000007490 hematoxylin and eosin (H&E) staining Methods 0.000 claims description 5
- 210000005228 liver tissue Anatomy 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 238000000386 microscopy Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 4
- 208000010159 IgA glomerulonephritis Diseases 0.000 claims description 4
- 206010021263 IgA nephropathy Diseases 0.000 claims description 4
- 241000700157 Rattus norvegicus Species 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 239000003102 growth factor Substances 0.000 claims description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 238000011552 rat model Methods 0.000 claims description 4
- 238000011160 research Methods 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 230000002485 urinary effect Effects 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- DCDSWTUVNHBRJZ-UHFFFAOYSA-N 1-(2-iodophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1I DCDSWTUVNHBRJZ-UHFFFAOYSA-N 0.000 claims description 3
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 3
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 206010028594 Myocardial fibrosis Diseases 0.000 claims description 3
- 206010039710 Scleroderma Diseases 0.000 claims description 3
- 208000031737 Tissue Adhesions Diseases 0.000 claims description 3
- 208000004608 Ureteral Obstruction Diseases 0.000 claims description 3
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 claims description 3
- 238000011047 acute toxicity test Methods 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 210000002744 extracellular matrix Anatomy 0.000 claims description 3
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 claims description 3
- 229960002428 fentanyl Drugs 0.000 claims description 3
- 238000000338 in vitro Methods 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000002611 ovarian Effects 0.000 claims description 3
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 3
- 229960002957 praziquantel Drugs 0.000 claims description 3
- 201000002793 renal fibrosis Diseases 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 150000003505 terpenes Chemical class 0.000 claims description 3
- 235000007586 terpenes Nutrition 0.000 claims description 3
- IFCIIDXNZSQOPD-UHFFFAOYSA-N 1-(2,3-dibromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(Br)=C1Br IFCIIDXNZSQOPD-UHFFFAOYSA-N 0.000 claims description 2
- VANOHWLVAFCHBO-UHFFFAOYSA-N 5-ethyl-1-phenylpyridin-2-one Chemical compound C1=C(CC)C=CC(=O)N1C1=CC=CC=C1 VANOHWLVAFCHBO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005541 ACE inhibitor Substances 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 2
- 208000019693 Lung disease Diseases 0.000 claims description 2
- 206010048654 Muscle fibrosis Diseases 0.000 claims description 2
- 208000013901 Nephropathies and tubular disease Diseases 0.000 claims description 2
- 206010034665 Peritoneal fibrosis Diseases 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
- 241000242677 Schistosoma japonicum Species 0.000 claims description 2
- 206010039610 Schistosomiasis liver Diseases 0.000 claims description 2
- 230000003187 abdominal effect Effects 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- 230000001772 anti-angiogenic effect Effects 0.000 claims description 2
- 230000004071 biological effect Effects 0.000 claims description 2
- 230000033228 biological regulation Effects 0.000 claims description 2
- 238000004364 calculation method Methods 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims description 2
- 230000005779 cell damage Effects 0.000 claims description 2
- 208000037887 cell injury Diseases 0.000 claims description 2
- 229940125898 compound 5 Drugs 0.000 claims description 2
- 210000002808 connective tissue Anatomy 0.000 claims description 2
- 230000007850 degeneration Effects 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
- 238000002405 diagnostic procedure Methods 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 230000004064 dysfunction Effects 0.000 claims description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 2
- 238000003304 gavage Methods 0.000 claims description 2
- 230000000004 hemodynamic effect Effects 0.000 claims description 2
- 230000036039 immunity Effects 0.000 claims description 2
- 229960000905 indomethacin Drugs 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims description 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 2
- 238000011835 investigation Methods 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 231100001231 less toxic Toxicity 0.000 claims description 2
- 210000002540 macrophage Anatomy 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 210000004379 membrane Anatomy 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 210000000651 myofibroblast Anatomy 0.000 claims description 2
- 230000017074 necrotic cell death Effects 0.000 claims description 2
- 230000035407 negative regulation of cell proliferation Effects 0.000 claims description 2
- 238000013059 nephrectomy Methods 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 230000036961 partial effect Effects 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims description 2
- 210000004303 peritoneum Anatomy 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 230000001766 physiological effect Effects 0.000 claims description 2
- 239000002504 physiological saline solution Substances 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 210000005084 renal tissue Anatomy 0.000 claims description 2
- 230000000284 resting effect Effects 0.000 claims description 2
- 230000036573 scar formation Effects 0.000 claims description 2
- 238000012453 sprague-dawley rat model Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims description 2
- 231100000167 toxic agent Toxicity 0.000 claims description 2
- 239000003440 toxic substance Substances 0.000 claims description 2
- 210000003437 trachea Anatomy 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 210000000626 ureter Anatomy 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims 10
- 239000007924 injection Substances 0.000 claims 10
- 238000011200 topical administration Methods 0.000 claims 6
- 210000003491 skin Anatomy 0.000 claims 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 4
- 239000010931 gold Substances 0.000 claims 4
- 229910052737 gold Inorganic materials 0.000 claims 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 3
- 206010036790 Productive cough Diseases 0.000 claims 3
- 210000003802 sputum Anatomy 0.000 claims 3
- 208000024794 sputum Diseases 0.000 claims 3
- AANMVENRNJYEMK-UHFFFAOYSA-N 4-propan-2-ylcyclohex-2-en-1-one Chemical compound CC(C)C1CCC(=O)C=C1 AANMVENRNJYEMK-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 241000700721 Hepatitis B virus Species 0.000 claims 2
- 206010020880 Hypertrophy Diseases 0.000 claims 2
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims 2
- 239000012888 bovine serum Substances 0.000 claims 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims 2
- 239000002917 insecticide Substances 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 claims 2
- 210000002307 prostate Anatomy 0.000 claims 2
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 claims 2
- UXJHQQLYKUVLIE-UHFFFAOYSA-N 1,2-dihydroacridine Chemical compound C1=CC=C2N=C(C=CCC3)C3=CC2=C1 UXJHQQLYKUVLIE-UHFFFAOYSA-N 0.000 claims 1
- MMWRGWQTAMNAFC-UHFFFAOYSA-N 1,2-dihydropyridine Chemical compound C1NC=CC=C1 MMWRGWQTAMNAFC-UHFFFAOYSA-N 0.000 claims 1
- MIUCEBJFPNOZFC-UHFFFAOYSA-N 1-(2,3-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(F)=C1F MIUCEBJFPNOZFC-UHFFFAOYSA-N 0.000 claims 1
- ICETYRMEWRWSJX-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(F)C=C1F ICETYRMEWRWSJX-UHFFFAOYSA-N 0.000 claims 1
- XBUPCRKIBSIBGJ-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC(OC)=CC=C1N1C(=O)C=CC(C)=C1 XBUPCRKIBSIBGJ-UHFFFAOYSA-N 0.000 claims 1
- MJWRQZILSOKOTB-UHFFFAOYSA-N 1-(2-methoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC=CC=C1N1C(=O)C=CC(C)=C1 MJWRQZILSOKOTB-UHFFFAOYSA-N 0.000 claims 1
- SGVKQHZMSAOGLV-UHFFFAOYSA-N 1-(3,5-difluorophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(F)=CC(F)=C1 SGVKQHZMSAOGLV-UHFFFAOYSA-N 0.000 claims 1
- MCAAQJLJBILPBZ-UHFFFAOYSA-N 1-(3-bromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(Br)=C1 MCAAQJLJBILPBZ-UHFFFAOYSA-N 0.000 claims 1
- NUUFOILDYXVXLL-UHFFFAOYSA-N 1-(3-methoxyphenyl)-5-methylpyridin-2-one Chemical compound COC1=CC=CC(N2C(C=CC(C)=C2)=O)=C1 NUUFOILDYXVXLL-UHFFFAOYSA-N 0.000 claims 1
- PYZJZGLJFOVHRH-UHFFFAOYSA-N 1-(4-bromophenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(Br)C=C1 PYZJZGLJFOVHRH-UHFFFAOYSA-N 0.000 claims 1
- QQOSQRFHCXTCMT-UHFFFAOYSA-N 1-[2,6-bis(trifluoromethyl)phenyl]-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=C(C(F)(F)F)C=CC=C1C(F)(F)F QQOSQRFHCXTCMT-UHFFFAOYSA-N 0.000 claims 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 claims 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- RSFSUBQOZSKHFU-UHFFFAOYSA-N 2-methyl-6-pyridin-3-yloxazinane Chemical group O1N(C)CCCC1C1=CC=CN=C1 RSFSUBQOZSKHFU-UHFFFAOYSA-N 0.000 claims 1
- UWDHESVDMJZCAI-UHFFFAOYSA-N 2-pyridin-2-yl-4h-pyridin-3-one Chemical compound O=C1CC=CN=C1C1=CC=CC=N1 UWDHESVDMJZCAI-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims 1
- NDGCMBKTLPWHDG-UHFFFAOYSA-N 5-methyl-1-(3-methylphenyl)pyridin-2-one Chemical compound CC1=CC=CC(N2C(C=CC(C)=C2)=O)=C1 NDGCMBKTLPWHDG-UHFFFAOYSA-N 0.000 claims 1
- RRHMWKBGPCGEOI-UHFFFAOYSA-N 5-methyl-1-[2-(trifluoromethyl)phenyl]pyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1C(F)(F)F RRHMWKBGPCGEOI-UHFFFAOYSA-N 0.000 claims 1
- IKTCWTVJVXLKRU-UHFFFAOYSA-N 5-methyl-1-[4-(trifluoromethyl)phenyl]pyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=C(C(F)(F)F)C=C1 IKTCWTVJVXLKRU-UHFFFAOYSA-N 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 1
- 102000015427 Angiotensins Human genes 0.000 claims 1
- 108010064733 Angiotensins Proteins 0.000 claims 1
- 241001480043 Arthrodermataceae Species 0.000 claims 1
- 241001532704 Azolla Species 0.000 claims 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 1
- 208000017667 Chronic Disease Diseases 0.000 claims 1
- 102000002322 Egg Proteins Human genes 0.000 claims 1
- 108010000912 Egg Proteins Proteins 0.000 claims 1
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical group OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 claims 1
- 239000005899 Fipronil Substances 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 241000711549 Hepacivirus C Species 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010053159 Organ failure Diseases 0.000 claims 1
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 claims 1
- 241000270666 Testudines Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-O acridine;hydron Chemical compound C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-O 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 230000003440 anti-fibrillation Effects 0.000 claims 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 125000004799 bromophenyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000001516 cell proliferation assay Methods 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 210000004748 cultured cell Anatomy 0.000 claims 1
- 230000037304 dermatophytes Effects 0.000 claims 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims 1
- 229960003957 dexamethasone Drugs 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 238000005516 engineering process Methods 0.000 claims 1
- 229940013764 fipronil Drugs 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 238000010255 intramuscular injection Methods 0.000 claims 1
- 239000007927 intramuscular injection Substances 0.000 claims 1
- 229930002839 ionone Natural products 0.000 claims 1
- 150000002499 ionone derivatives Chemical class 0.000 claims 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- 210000005033 mesothelial cell Anatomy 0.000 claims 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 claims 1
- 210000004681 ovum Anatomy 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 230000007096 poisonous effect Effects 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 238000012216 screening Methods 0.000 claims 1
- 210000004927 skin cell Anatomy 0.000 claims 1
- 229960001052 streptozocin Drugs 0.000 claims 1
- 238000005556 structure-activity relationship Methods 0.000 claims 1
- 238000010189 synthetic method Methods 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 230000002110 toxicologic effect Effects 0.000 claims 1
- 231100000027 toxicology Toxicity 0.000 claims 1
- 210000002700 urine Anatomy 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 description 3
- 241000242678 Schistosoma Species 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000006882 induction of apoptosis Effects 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 230000008506 pathogenesis Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- ILFPCMXTASDZKM-YFKPBYRVSA-N (1s)-2-methylidene-3-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@H]1CCC(=O)C1=C ILFPCMXTASDZKM-YFKPBYRVSA-N 0.000 description 1
- DLAIQUGBQRXOBE-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-5-methylpyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC(C)=CC(C)=C1 DLAIQUGBQRXOBE-UHFFFAOYSA-N 0.000 description 1
- IPFDTWHBEBJTLE-UHFFFAOYSA-N 2h-acridin-1-one Chemical compound C1=CC=C2C=C3C(=O)CC=CC3=NC2=C1 IPFDTWHBEBJTLE-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
- 102000008873 Angiotensin II receptor Human genes 0.000 description 1
- 108050000824 Angiotensin II receptor Proteins 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical group FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102100039131 Integrator complex subunit 5 Human genes 0.000 description 1
- 101710092888 Integrator complex subunit 5 Proteins 0.000 description 1
- 208000011948 Multi-organ disease Diseases 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000007131 anti Alzheimer effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 238000010827 pathological analysis Methods 0.000 description 1
- ILFPCMXTASDZKM-UHFFFAOYSA-N sarkomycin Natural products OC(=O)C1CCC(=O)C1=C ILFPCMXTASDZKM-UHFFFAOYSA-N 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 239000004017 serum-free culture medium Substances 0.000 description 1
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
- 210000004500 stellate cell Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Rheumatology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2005100314457A CN1846699A (zh) | 2005-04-13 | 2005-04-13 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
| PCT/CN2006/000651 WO2006108354A1 (fr) | 2005-04-13 | 2006-04-11 | 5-méthyl-2-(1h)-pyridone substituée en 1 par un groupement phényle dans la fabrication de médicaments pour le traitement de la fibrose d'organes ou de tissus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200808315A true TW200808315A (en) | 2008-02-16 |
Family
ID=37076581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW095128659A TW200808315A (en) | 2005-04-13 | 2006-08-04 | A novel composition for treating organ or tissue fibrosis comprising 5-methyl-1-(substituted phenyl)-2-(1H)pyridone |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US20090005424A9 (enExample) |
| EP (1) | EP1878428A4 (enExample) |
| JP (1) | JP2008535871A (enExample) |
| KR (1) | KR20080018857A (enExample) |
| CN (2) | CN1846699A (enExample) |
| AU (1) | AU2006233433A1 (enExample) |
| CA (1) | CA2603763A1 (enExample) |
| RU (1) | RU2007141892A (enExample) |
| TW (1) | TW200808315A (enExample) |
| WO (1) | WO2006108354A1 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9733625B2 (en) | 2006-03-20 | 2017-08-15 | General Electric Company | Trip optimization system and method for a train |
| US10569792B2 (en) | 2006-03-20 | 2020-02-25 | General Electric Company | Vehicle control system and method |
| US10308265B2 (en) | 2006-03-20 | 2019-06-04 | Ge Global Sourcing Llc | Vehicle control system and method |
| US8924049B2 (en) | 2003-01-06 | 2014-12-30 | General Electric Company | System and method for controlling movement of vehicles |
| US7825133B2 (en) | 2003-11-14 | 2010-11-02 | Shanghai Genomics, Inc. | Derivatives of pyridone and the use of them |
| CN1846699A (zh) * | 2005-04-13 | 2006-10-18 | 中南大学湘雅医院 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
| AP2007004244A0 (en) | 2005-05-10 | 2007-12-31 | Intermune Inc | Method of modulating stress-activated protein kinase system |
| US9156477B2 (en) | 2006-03-20 | 2015-10-13 | General Electric Company | Control system and method for remotely isolating powered units in a vehicle system |
| US9689681B2 (en) | 2014-08-12 | 2017-06-27 | General Electric Company | System and method for vehicle operation |
| US8126601B2 (en) | 2006-03-20 | 2012-02-28 | General Electric Company | System and method for predicting a vehicle route using a route network database |
| US8290645B2 (en) | 2006-03-20 | 2012-10-16 | General Electric Company | Method and computer software code for determining a mission plan for a powered system when a desired mission parameter appears unobtainable |
| US8370006B2 (en) | 2006-03-20 | 2013-02-05 | General Electric Company | Method and apparatus for optimizing a train trip using signal information |
| WO2009039773A1 (fr) * | 2007-09-19 | 2009-04-02 | Central South University | Nouvelle utilisation thérapeutique d'une aryl-2(1h)-pyridone substituée en position 1 |
| CN101235013A (zh) * | 2008-03-10 | 2008-08-06 | 广东东阳光药业有限公司 | 结晶型1-（3-氟苯基）-5-甲基-2-（1h）吡啶酮、其制备方法、及其组合物和应用 |
| EP2296653B1 (en) | 2008-06-03 | 2016-01-27 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| WO2010045871A1 (en) * | 2008-10-21 | 2010-04-29 | Dieretech Investment Limited | Composition and method for treating proteinuria |
| US7566729B1 (en) | 2008-11-10 | 2009-07-28 | Intermune, Inc. | Modifying pirfenidone treatment for patients with atypical liver function |
| US7635707B1 (en) | 2008-11-10 | 2009-12-22 | Intermune, Inc. | Pirfenidone treatment for patients with atypical liver function |
| US8016980B2 (en) | 2008-11-25 | 2011-09-13 | Dixie Consumer Products Llc | Paper products |
| US9834237B2 (en) | 2012-11-21 | 2017-12-05 | General Electric Company | Route examining system and method |
| CN101921225B (zh) * | 2009-06-11 | 2013-04-03 | 北京凯得尔森生物技术有限公司 | 吡啡尼酮类化合物、其制备方法和应用 |
| US7816383B1 (en) | 2009-12-04 | 2010-10-19 | Intermune, Inc. | Methods of administering pirfenidone therapy |
| US8084475B2 (en) | 2009-12-04 | 2011-12-27 | Intermune, Inc. | Pirfenidone therapy and inducers of cytochrome P450 |
| US10105356B2 (en) | 2011-01-31 | 2018-10-23 | Avalyn Pharma Inc. | Aerosol pirfenidone and pyridone analog compounds and uses thereof |
| HUE058753T2 (hu) | 2011-01-31 | 2022-09-28 | Avalyn Pharma Inc | Aeroszol formájú pirfenidon- és piridon-analóg vegyületek és alkalmazásaik |
| US9434695B2 (en) | 2012-07-18 | 2016-09-06 | Sunshine Lake Pharma Co., Ltd | Nitrogenous heterocyclic derivatives and their application in drugs |
| CA2819967C (en) | 2012-08-31 | 2016-03-22 | Intermune, Inc. | Use of pirfenidone concomitantly with ciprofloxacin |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| US9669851B2 (en) | 2012-11-21 | 2017-06-06 | General Electric Company | Route examination system and method |
| US9682716B2 (en) | 2012-11-21 | 2017-06-20 | General Electric Company | Route examining system and method |
| JP6454348B2 (ja) * | 2013-12-19 | 2019-01-16 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． | 窒素複素環誘導体およびその医薬品への応用 |
| JP7066321B2 (ja) | 2014-01-10 | 2022-05-13 | アヴァリン ファーマ インク． | エアロゾルのピルフェニドン及びピリドンのアナログの化合物、及び、その使用 |
| BR112016020987B1 (pt) | 2014-03-12 | 2023-11-14 | Western Sydney Local Health District | Método de identificação de receptores de aloenxerto renal e método de seleção de receptor do aloenxerto renal |
| RU2692485C2 (ru) | 2014-04-02 | 2019-06-25 | Интермьюн, Инк. | Противофиброзные пиридиноны |
| ES2850281T3 (es) | 2014-06-26 | 2021-08-26 | Icahn School Med Mount Sinai | Método para diagnosticar el rechazo agudo subclínico y clínico mediante el análisis de conjuntos de genes predictivos, un agente terapéutico para usar en el tratamiento y kits para determinar la expresión |
| WO2016044153A1 (en) * | 2014-09-18 | 2016-03-24 | Rush University Medical Center | Methods for preventing or treating osteoarthritis |
| DE102015217418A1 (de) | 2015-09-11 | 2017-03-16 | Mühlbauer Technology Gmbh | Radikalisch polymerisierbares Dentalmaterial |
| EP3308765B1 (de) | 2016-10-17 | 2022-07-13 | Mühlbauer Technology GmbH | Radikalisch polymerisierbare verbindung |
| WO2019011163A1 (en) * | 2017-07-14 | 2019-01-17 | Sunshine Lake Pharma Co., Ltd. | PROCESS FOR THE PREPARATION OF A PYRIMIDONE COMPOUND |
| JP7464279B2 (ja) | 2018-04-16 | 2024-04-09 | アイカーン スクール オブ メディスン アット マウント シナイ | レシピエント血液における移植前トランスクリプトームシグネチャーを使用した急性拒絶反応および腎臓同種異系移植喪失の予測のための方法およびキット |
| CN113456636A (zh) * | 2021-07-09 | 2021-10-01 | 中南大学 | 一种氟非尼酮在制备急性肝损伤药物中的应用 |
| CN113274389B (zh) * | 2021-07-09 | 2022-11-08 | 中南大学 | 氟非尼酮在制备治疗急性肺损伤药物中的应用 |
| CN114716365B (zh) * | 2022-01-04 | 2024-03-01 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮化合物或其可药用盐在治疗肺纤维化中的应用 |
| WO2024235145A1 (zh) * | 2023-05-12 | 2024-11-21 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮及内过氧化物的制备和应用 |
| CN121695138A (zh) * | 2023-10-30 | 2026-03-20 | 大连理工大学 | 一类n-取代苯基-2-吡啶酮化合物在治疗癌症中的应用 |
| CN120053452B (zh) * | 2023-11-30 | 2025-12-05 | 长沙晶易医药科技股份有限公司 | 一种2,4-二取代-5-氟嘧啶衍生物的新用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4052509A (en) | 1972-12-18 | 1977-10-04 | Affiliated Medical Research, Inc. | Method for reducing serum uric acid levels |
| US4042699A (en) | 1972-12-18 | 1977-08-16 | Affiliated Medical Research, Inc. | Method for reducing serum glucose levels |
| CA1049411A (en) | 1972-12-18 | 1979-02-27 | Affiliated Medical Research | N-substituted pyridone and general method for preparing pyridones |
| US3839346A (en) | 1972-12-18 | 1974-10-01 | Affiliated Med Res | N-substituted pyridone and general method for preparing pyridones |
| JPH02215719A (ja) * | 1989-02-15 | 1990-08-28 | Yamauchi Akitomo | 線維化病変組織の修復並びに線維化病変の阻止剤 |
| US5518729A (en) | 1989-11-22 | 1996-05-21 | Margolin; Solomon B. | Compositions and methods for reparation and prevention of fibrotic lesions |
| US5310562A (en) * | 1989-11-22 | 1994-05-10 | Margolin Solomon B | Composition and method for reparation and prevention of fibrotic lesions |
| US5716632A (en) | 1989-11-22 | 1998-02-10 | Margolin; Solomon B. | Compositions and methods for reparation and prevention of fibrotic lesions |
| CN2114190U (zh) | 1992-01-09 | 1992-08-26 | 王刚 | 恒流一体化集成电源器件 |
| US5716623A (en) * | 1994-12-07 | 1998-02-10 | Immunex Corporation | Isolated Herpesvirus saimiri proteins that bind MHC Class II molecules |
| JP3496553B2 (ja) * | 1998-08-07 | 2004-02-16 | 株式会社高尾 | 弾球遊技機 |
| CN1218942C (zh) * | 2002-06-11 | 2005-09-14 | 中南大学湘雅医学院 | 抗纤维化吡啶酮化合物及其生产工艺方法 |
| CN1846699A (zh) * | 2005-04-13 | 2006-10-18 | 中南大学湘雅医院 | 1－(取代苯基)－5－甲基－2－(1h) 吡啶酮(i)化合物用于制备抗除肾间质纤维化外其他器官纤维化或组织纤维化药物的应用 |
-
2005
- 2005-04-13 CN CNA2005100314457A patent/CN1846699A/zh active Pending
-
2006
- 2006-04-11 AU AU2006233433A patent/AU2006233433A1/en not_active Abandoned
- 2006-04-11 EP EP06722303A patent/EP1878428A4/en not_active Withdrawn
- 2006-04-11 KR KR1020077018590A patent/KR20080018857A/ko not_active Ceased
- 2006-04-11 JP JP2008505716A patent/JP2008535871A/ja active Pending
- 2006-04-11 RU RU2007141892/15A patent/RU2007141892A/ru not_active Application Discontinuation
- 2006-04-11 CA CA002603763A patent/CA2603763A1/en not_active Abandoned
- 2006-04-11 WO PCT/CN2006/000651 patent/WO2006108354A1/zh not_active Ceased
- 2006-04-11 CN CN2006800002161A patent/CN1953749B/zh not_active Expired - Lifetime
- 2006-08-04 TW TW095128659A patent/TW200808315A/zh unknown
-
2007
- 2007-05-01 US US11/742,664 patent/US20090005424A9/en not_active Abandoned
-
2008
- 2008-09-04 US US12/204,629 patent/US20080319027A1/en not_active Abandoned
-
2009
- 2009-06-25 US US12/491,506 patent/US20090258911A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090005424A9 (en) | 2009-01-01 |
| US20090258911A1 (en) | 2009-10-15 |
| EP1878428A1 (en) | 2008-01-16 |
| EP1878428A4 (en) | 2008-09-03 |
| CA2603763A1 (en) | 2006-10-19 |
| CN1953749A (zh) | 2007-04-25 |
| JP2008535871A (ja) | 2008-09-04 |
| US20080319027A1 (en) | 2008-12-25 |
| CN1953749B (zh) | 2010-04-14 |
| KR20080018857A (ko) | 2008-02-28 |
| AU2006233433A1 (en) | 2006-10-19 |
| US20070203203A1 (en) | 2007-08-30 |
| WO2006108354A1 (fr) | 2006-10-19 |
| RU2007141892A (ru) | 2009-05-20 |
| CN1846699A (zh) | 2006-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1953749B (zh) | 1-(取代苯基)-5-甲基-2-(1h)吡啶酮(ⅰ)化合物用于制备抗器官或组织纤维化药物的应用 | |
| CA2747251A1 (en) | Methods for treating acute myocardial infarctions and associated disorders | |
| TW200401768A (en) | Methods of treatment with CETP inhibitors and antihypertensive agents | |
| JP2010209123A (ja) | 有機化合物の組合せ | |
| CA3083347A1 (en) | Compositions and methods of treatment for neurological disorders comprising motor neuron diseases | |
| EP4426298B1 (en) | New therapeutic combinations comprising pirfenidone and pde4-inhibitor for the treatment of progressive fibrosing interstitial lung diseases | |
| Fink et al. | Therapeutic potential of P irfenidone for treating equine corneal scarring | |
| JP2017014224A (ja) | 帯状疱疹関連痛の急性期疼痛の予防又は治療剤 | |
| KR20020075797A (ko) | 엔도텔린 유발성 질환 치료제 | |
| WO2001008705A1 (en) | Remedies for neurogenic pains | |
| EP1485083A2 (en) | Dexanabinol and dexanabinol analogs regulate inflammation related genes | |
| JPH11509830A (ja) | 再狭窄を処置する薬剤を製造するためのレチノイドの使用 | |
| WO2008020651A1 (fr) | antagoniste de récepteur P2X4 | |
| US20050137251A1 (en) | Dexanabinol and dexanabinol analogs regulate inflammation related genes | |
| TW202327579A (zh) | Ｔｅａｄ抑制劑的給藥方案 | |
| JP2019516699A (ja) | 純粋な５−ｈｔ６受容体アンタゴニストとアセチルコリンエステラーゼ阻害剤の組合せ | |
| CN107334767B (zh) | 一种哒嗪酮类化合物在肿瘤治疗中的应用 | |
| CN113730407A (zh) | 使用s-羟氯喹进行的红斑性狼疮的治疗 | |
| WO2017143964A1 (zh) | Quisinostat，一种新型的高效抗疟药物 | |
| JPH04225917A (ja) | 記憶増強剤として有用な５−アリ−ル−４−アルキル−３ｈ−１，２，４−トリアゾール−３−チオン類 | |
| KR20070034070A (ko) | 신경병성 통증, 섬유근통 또는 류마티스성 관절염의 치료 | |
| JP2019516696A (ja) | 純粋な５−ｈｔ６受容体アンタゴニストのｎｍｄａ受容体アンタゴニストとの組合せ | |
| CA3250489A1 (en) | PREVENTION AND TREATMENT OF POSTOPERATIVE COGNITIVE DYSFUNCTIONS | |
| KR20060130619A (ko) | 유기 화합물의 조합물 | |
| JP4634303B2 (ja) | 血管新生抑制薬 |