CA2601158C - The use of a prostaglandin for treating mucosal disorders - Google Patents
The use of a prostaglandin for treating mucosal disorders Download PDFInfo
- Publication number
- CA2601158C CA2601158C CA2601158A CA2601158A CA2601158C CA 2601158 C CA2601158 C CA 2601158C CA 2601158 A CA2601158 A CA 2601158A CA 2601158 A CA2601158 A CA 2601158A CA 2601158 C CA2601158 C CA 2601158C
- Authority
- CA
- Canada
- Prior art keywords
- cancer
- compound
- prostaglandin
- carcinoma
- keto
- 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.)
- Expired - Fee Related
Links
- 150000003180 prostaglandins Chemical class 0.000 title description 32
- -1 prostaglandin compound Chemical class 0.000 claims abstract description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 210000004877 mucosa Anatomy 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 208000006994 Precancerous Conditions Diseases 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 208000023514 Barrett esophagus Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 7
- 208000023665 Barrett oesophagus Diseases 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 201000008275 breast carcinoma Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 201000009030 Carcinoma Diseases 0.000 claims description 4
- 229960000711 alprostadil Drugs 0.000 claims description 4
- 206010017758 gastric cancer Diseases 0.000 claims description 4
- 201000002313 intestinal cancer Diseases 0.000 claims description 4
- 206010005003 Bladder cancer Diseases 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 208000010749 gastric carcinoma Diseases 0.000 claims description 3
- 201000000498 stomach carcinoma Diseases 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 206010061424 Anal cancer Diseases 0.000 claims description 2
- 208000017897 Carcinoma of esophagus Diseases 0.000 claims description 2
- 206010061825 Duodenal neoplasm Diseases 0.000 claims description 2
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims description 2
- 201000003741 Gastrointestinal carcinoma Diseases 0.000 claims description 2
- 208000005016 Intestinal Neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
- 206010054184 Small intestine carcinoma Diseases 0.000 claims description 2
- 208000000277 Splenic Neoplasms Diseases 0.000 claims description 2
- 208000033781 Thyroid carcinoma Diseases 0.000 claims description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 201000007538 anal carcinoma Diseases 0.000 claims description 2
- 208000021780 appendiceal neoplasm Diseases 0.000 claims description 2
- 201000000312 duodenum cancer Diseases 0.000 claims description 2
- 201000005619 esophageal carcinoma Diseases 0.000 claims description 2
- 201000010175 gallbladder cancer Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 206010038038 rectal cancer Diseases 0.000 claims description 2
- 201000001275 rectum cancer Diseases 0.000 claims description 2
- 201000010174 renal carcinoma Diseases 0.000 claims description 2
- 201000002471 spleen cancer Diseases 0.000 claims description 2
- 230000002381 testicular Effects 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- 208000013077 thyroid gland carcinoma Diseases 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 206010046766 uterine cancer Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 27
- 238000011282 treatment Methods 0.000 abstract description 22
- 238000000034 method Methods 0.000 abstract description 15
- 230000004682 mucosal barrier function Effects 0.000 abstract description 12
- 238000011084 recovery Methods 0.000 abstract description 11
- 230000008859 change Effects 0.000 abstract description 9
- 210000001578 tight junction Anatomy 0.000 abstract description 8
- 102000000591 Tight Junction Proteins Human genes 0.000 abstract description 5
- 108010002321 Tight Junction Proteins Proteins 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 description 65
- 125000000217 alkyl group Chemical group 0.000 description 45
- 210000001519 tissue Anatomy 0.000 description 30
- 125000003545 alkoxy group Chemical group 0.000 description 22
- 230000000694 effects Effects 0.000 description 19
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 19
- 230000000302 ischemic effect Effects 0.000 description 18
- 208000028867 ischemia Diseases 0.000 description 16
- 230000004907 flux Effects 0.000 description 15
- 239000000594 mannitol Substances 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 230000004888 barrier function Effects 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 230000004044 response Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 12
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 11
- 208000035475 disorder Diseases 0.000 description 11
- 210000003405 ileum Anatomy 0.000 description 11
- 125000004043 oxo group Chemical group O=* 0.000 description 11
- 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 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 230000002496 gastric effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000004423 acyloxy group Chemical group 0.000 description 8
- 125000004104 aryloxy group Chemical group 0.000 description 8
- 210000000981 epithelium Anatomy 0.000 description 8
- 241000557626 Corvus corax Species 0.000 description 7
- 206010061218 Inflammation Diseases 0.000 description 7
- 210000001815 ascending colon Anatomy 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 description 7
- 230000004054 inflammatory process Effects 0.000 description 7
- 230000007358 intestinal barrier function Effects 0.000 description 7
- 230000000968 intestinal effect Effects 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 230000028327 secretion Effects 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 150000005215 alkyl ethers Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 5
- 206010022680 Intestinal ischaemia Diseases 0.000 description 5
- 238000003287 bathing Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 229960000905 indomethacin Drugs 0.000 description 5
- 208000037906 ischaemic injury Diseases 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000035479 physiological effects, processes and functions Effects 0.000 description 5
- 230000004936 stimulating effect Effects 0.000 description 5
- 229910052717 sulfur Chemical group 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 206010010774 Constipation Diseases 0.000 description 4
- 208000011231 Crohn disease Diseases 0.000 description 4
- 206010012735 Diarrhoea Diseases 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 description 4
- 208000025467 Gastrointestinal mucosal disease Diseases 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 230000004075 alteration Effects 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 210000001072 colon Anatomy 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000003745 diagnosis Methods 0.000 description 4
- 208000010643 digestive system disease Diseases 0.000 description 4
- 150000002066 eicosanoids Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 208000018685 gastrointestinal system disease Diseases 0.000 description 4
- 208000019423 liver disease Diseases 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000007310 pathophysiology Effects 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 4
- 206010009900 Colitis ulcerative Diseases 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 208000034486 Multi-organ failure Diseases 0.000 description 3
- 208000010718 Multiple Organ Failure Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000282887 Suidae Species 0.000 description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 206010009887 colitis Diseases 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 3
- 230000004890 epithelial barrier function Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 230000010412 perfusion Effects 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- 208000005623 Carcinogenesis Diseases 0.000 description 2
- 108091006146 Channels Proteins 0.000 description 2
- 208000027932 Collagen disease Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 206010018691 Granuloma Diseases 0.000 description 2
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000036952 cancer formation Effects 0.000 description 2
- 231100000504 carcinogenesis Toxicity 0.000 description 2
- 239000000799 cathartic agent Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 229960002986 dinoprostone Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 150000002373 hemiacetals Chemical class 0.000 description 2
- 238000010562 histological examination Methods 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 229940125721 immunosuppressive agent Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000007972 injectable composition Substances 0.000 description 2
- 210000005027 intestinal barrier Anatomy 0.000 description 2
- 210000004347 intestinal mucosa Anatomy 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 description 2
- 229960005249 misoprostol Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- 102220279244 rs1555053901 Human genes 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 201000009881 secretory diarrhea Diseases 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 239000006190 sub-lingual tablet Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000003826 tablet Substances 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
- 229960003279 thiopental Drugs 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- PNKZBZPLRKCVLI-UHFFFAOYSA-N (2-methylpropan-2-yl)oxybenzene Chemical compound CC(C)(C)OC1=CC=CC=C1 PNKZBZPLRKCVLI-UHFFFAOYSA-N 0.000 description 1
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical class CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- POEDHWVTLBLWDA-UHFFFAOYSA-N 1-butylindole-2,3-dione Chemical compound C1=CC=C2N(CCCC)C(=O)C(=O)C2=C1 POEDHWVTLBLWDA-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- DEBGMRXCXCOKTA-UHFFFAOYSA-N 1-methoxy-1-(1-methoxyethoxy)ethane Chemical compound COC(C)OC(C)OC DEBGMRXCXCOKTA-UHFFFAOYSA-N 0.000 description 1
- PRHCBRXAHBBRKA-UHFFFAOYSA-N 2-(2-hydroxypropan-2-yloxy)propan-2-ol Chemical compound CC(C)(O)OC(C)(C)O PRHCBRXAHBBRKA-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- PLNNBRYFKARCEV-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)methoxymethyl]phenol Chemical compound OC1=CC=CC=C1COCC1=CC=CC=C1O PLNNBRYFKARCEV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SAWMBRUFQYQNLJ-UHFFFAOYSA-N 3-ethyl-3-(3-ethyloctan-3-yloxy)octane Chemical compound CCCCCC(CC)(CC)OC(CC)(CC)CCCCC SAWMBRUFQYQNLJ-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- XHWSCQCJAPLELI-UHFFFAOYSA-N 4-(3,4-dimethoxyphenoxy)-1,2-dimethoxybenzene Chemical compound C1=C(OC)C(OC)=CC=C1OC1=CC=C(OC)C(OC)=C1 XHWSCQCJAPLELI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000027496 Behcet disease Diseases 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108010062745 Chloride Channels Proteins 0.000 description 1
- 102000011045 Chloride Channels Human genes 0.000 description 1
- 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 1
- 206010009657 Clostridium difficile colitis Diseases 0.000 description 1
- 206010009895 Colitis ischaemic Diseases 0.000 description 1
- 206010056979 Colitis microscopic Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 208000028399 Critical Illness Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 240000002989 Euphorbia neriifolia Species 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
- 241000590002 Helicobacter pylori Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010022678 Intestinal infections Diseases 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 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
- 241000124008 Mammalia Species 0.000 description 1
- 208000004535 Mesenteric Ischemia Diseases 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000002389 Pouchitis Diseases 0.000 description 1
- 206010036774 Proctitis Diseases 0.000 description 1
- 206010036783 Proctitis ulcerative Diseases 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
- 208000003100 Pseudomembranous Enterocolitis Diseases 0.000 description 1
- 101000897961 Rattus norvegicus Endothelial cell-specific molecule 1 Proteins 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000010162 Tukey test Methods 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- QUXMPZUVBXHUII-UHFFFAOYSA-N [1,1-bis(hydroxymethylamino)ethylamino]methanol Chemical class OCNC(C)(NCO)NCO QUXMPZUVBXHUII-UHFFFAOYSA-N 0.000 description 1
- PVQATPQSBYNMGE-UHFFFAOYSA-N [benzhydryloxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)C1=CC=CC=C1 PVQATPQSBYNMGE-UHFFFAOYSA-N 0.000 description 1
- XXFXTBNFFMQVKJ-UHFFFAOYSA-N [diphenyl(trityloxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XXFXTBNFFMQVKJ-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols 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
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001483 arginine derivatives Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 210000002469 basement membrane Anatomy 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229940075397 calomel Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000012292 cell migration Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 208000008609 collagenous colitis Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 230000002153 concerted effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000001120 cytoprotective effect Effects 0.000 description 1
- 230000008260 defense mechanism Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 208000014793 distal colitis Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 208000007784 diverticulitis Diseases 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 208000010227 enterocolitis Diseases 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 230000034964 establishment of cell polarity Effects 0.000 description 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- LZTCEQQSARXBHE-UHFFFAOYSA-N ethoxycyclopropane Chemical compound CCOC1CC1 LZTCEQQSARXBHE-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- CQYBANOHCYKAEE-UHFFFAOYSA-N ethynoxyethyne Chemical compound C#COC#C CQYBANOHCYKAEE-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000001200 fecal consistency Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004868 gas analysis Methods 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940037467 helicobacter pylori Drugs 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002962 histologic effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 201000008254 ileocolitis Diseases 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010874 in vitro model Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000035992 intercellular communication Effects 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 208000003243 intestinal obstruction Diseases 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 201000008222 ischemic colitis Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 208000004341 lymphocytic colitis Diseases 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000034956 maintenance of cell polarity Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 210000005075 mammary gland Anatomy 0.000 description 1
- 238000012961 medicinal therapy Methods 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 208000008275 microscopic colitis Diseases 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 238000007491 morphometric analysis Methods 0.000 description 1
- 230000003562 morphometric effect Effects 0.000 description 1
- 238000013425 morphometry Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 210000000754 myometrium Anatomy 0.000 description 1
- AIAKLPAJNLBVEA-UHFFFAOYSA-N n-[2-(2-benzamidophenoxy)phenyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC=C1 AIAKLPAJNLBVEA-UHFFFAOYSA-N 0.000 description 1
- 210000005170 neoplastic cell Anatomy 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 208000013236 oncocytic neoplasm Diseases 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000004466 pelleted feed Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 150000003165 prostaglandin E1 derivatives Chemical class 0.000 description 1
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 229940098466 sublingual tablet Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical group C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- UQZVCDCIMBLVNR-TWYODKAFSA-N sulprostone Chemical compound O[C@@H]1CC(=O)[C@H](C\C=C/CCCC(=O)NS(=O)(=O)C)[C@H]1\C=C\[C@@H](O)COC1=CC=CC=C1 UQZVCDCIMBLVNR-TWYODKAFSA-N 0.000 description 1
- 229960003400 sulprostone Drugs 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000030968 tissue homeostasis Effects 0.000 description 1
- 239000012929 tonicity agent Substances 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 206010044412 transitional cell carcinoma Diseases 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N trimethylxanthine Natural products CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 208000025835 ulcerative proctosigmoiditis Diseases 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 230000037314 wound repair Effects 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- 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
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- 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
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2831416A CA2831416C (en) | 2005-03-21 | 2006-03-22 | The use of a prostaglandin for treating mucosal disorders |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66320005P | 2005-03-21 | 2005-03-21 | |
| US60/663,200 | 2005-03-21 | ||
| US67992005P | 2005-05-11 | 2005-05-11 | |
| US60/679,920 | 2005-05-11 | ||
| US72197605P | 2005-09-30 | 2005-09-30 | |
| US60/721,976 | 2005-09-30 | ||
| PCT/JP2006/306380 WO2006101244A2 (en) | 2005-03-21 | 2006-03-22 | Method and composition for treating mucosal disorders |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2831416A Division CA2831416C (en) | 2005-03-21 | 2006-03-22 | The use of a prostaglandin for treating mucosal disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2601158A1 CA2601158A1 (en) | 2006-09-28 |
| CA2601158C true CA2601158C (en) | 2015-10-13 |
Family
ID=36754577
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2601158A Expired - Fee Related CA2601158C (en) | 2005-03-21 | 2006-03-22 | The use of a prostaglandin for treating mucosal disorders |
| CA2831416A Expired - Fee Related CA2831416C (en) | 2005-03-21 | 2006-03-22 | The use of a prostaglandin for treating mucosal disorders |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2831416A Expired - Fee Related CA2831416C (en) | 2005-03-21 | 2006-03-22 | The use of a prostaglandin for treating mucosal disorders |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20060281818A1 (enExample) |
| EP (3) | EP1861169B1 (enExample) |
| JP (2) | JP5219797B2 (enExample) |
| KR (2) | KR101456298B1 (enExample) |
| CN (1) | CN103948603A (enExample) |
| AU (1) | AU2006225515B2 (enExample) |
| BR (1) | BRPI0609672A2 (enExample) |
| CA (2) | CA2601158C (enExample) |
| ES (1) | ES2592283T3 (enExample) |
| IL (1) | IL185861A (enExample) |
| MX (1) | MX2007011645A (enExample) |
| NO (1) | NO20075361L (enExample) |
| NZ (3) | NZ562351A (enExample) |
| WO (1) | WO2006101244A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004037268A1 (en) * | 2002-10-23 | 2004-05-06 | Sucampo Ag | Prostaglandin compounds for the treatment of obesity |
| US20060281818A1 (en) * | 2005-03-21 | 2006-12-14 | Sucampo Ag, North Carolina State University | Method for treating mucosal disorders |
| EP2059247A1 (en) | 2006-09-06 | 2009-05-20 | Sucampo AG | Method and composition for promoting gastrointestinal bicarbonate secretion |
| WO2009055769A1 (en) | 2007-10-25 | 2009-04-30 | Phytoceutica, Inc. | Use of phy906 as treatment for inflammatory bowel disease and/or irritable bowel syndrome |
| US8871752B2 (en) * | 2008-02-19 | 2014-10-28 | Sucampo Ag | Method for modulating stem cell growth |
| US8569279B2 (en) | 2009-05-27 | 2013-10-29 | Sucampo Ag | Method for modulating claudin mediated functions |
| US20100305203A1 (en) * | 2009-05-27 | 2010-12-02 | Sucampo Ag | Method for modulating claudin mediated functions |
| US9084815B2 (en) * | 2009-09-16 | 2015-07-21 | Sucampo Ag | Method for treating damage induced by an anti-tumor agent, treating mucositis and treating tumor |
| EP2699244A4 (en) * | 2011-04-19 | 2014-10-22 | Sucampo Ag | METHOD FOR MODULATING CYTOKINACTIVITY |
| EP2701709A4 (en) * | 2011-04-27 | 2014-10-15 | Sucampo Ag | METHOD FOR MODULATING ION TRANSPORTERS |
| WO2014159679A1 (en) | 2013-03-12 | 2014-10-02 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Methods for using lubiprostone to absorb fluid from the subretinal space |
| US20150099802A1 (en) * | 2013-10-03 | 2015-04-09 | Sucampo Ag | Selective tumor treatment |
| US20160120840A1 (en) * | 2014-10-30 | 2016-05-05 | Sucampo Ag | Method and composition for treating nonerosive reflux disease |
| PL3292135T3 (pl) * | 2015-05-06 | 2023-01-02 | Wageningen Universiteit | Zastosowanie polipeptydu do wpływania na sygnalizację odpornościową i/lub wpływania na funkcję bariery jelitowej i/lub modulowania stanu metabolicznego |
| WO2024217532A1 (zh) * | 2023-04-20 | 2024-10-24 | 中南大学湘雅二医院 | Carboprost在制备抗肿瘤药物中的应用 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2645710C2 (de) * | 1976-10-09 | 1985-06-27 | Merck Patent Gmbh, 6100 Darmstadt | Phenoxy-amino-propanole, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitung |
| GB1581886A (en) * | 1977-05-26 | 1980-12-31 | May & Baker Ltd | Prostanol derivatives |
| JPS58216155A (ja) * | 1982-06-10 | 1983-12-15 | Ono Pharmaceut Co Ltd | 新規なプロスタグランジンｄ類似化合物 |
| JPS591463A (ja) * | 1982-06-28 | 1984-01-06 | Ono Pharmaceut Co Ltd | 新規なプロスタグランジンｄ類似化合物 |
| FR2608924B1 (fr) * | 1986-12-29 | 1990-07-20 | Pasteur Institut | Compositions therapeutiques contenant des derives soufres de prostaglandines, nouveaux derives soufres et leur procede de preparation |
| CA1322749C (en) | 1987-01-28 | 1993-10-05 | Ryuzo Ueno | Prostaglandins of the d series, and tranquilizers and soporifics containing the same |
| US5225439A (en) | 1987-01-28 | 1993-07-06 | K.K. Ueno Seiyaku Oyo Kenkyujo | Prostaglandins E and anti ulcers containing same |
| US5166174A (en) | 1987-01-28 | 1992-11-24 | K.K. Ueno Seiyaku Oyo Kenkyujo | Prostaglandins E and anti-ulcers containing same |
| CA1323364C (en) * | 1987-01-28 | 1993-10-19 | Ryuzo Ueno | Prostaglandins e and anti ulcer agents containing same |
| US5428062A (en) * | 1987-01-28 | 1995-06-27 | K.K. Ueno Seiyaku Oyo Kenkyujo | Prostaglandins E and anti ulcers containing same |
| US5221763A (en) | 1987-04-30 | 1993-06-22 | R-Tech Ueno, Ltd. | Prostaglandins of the F series |
| US5317032A (en) | 1987-10-02 | 1994-05-31 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Prostaglandin cathartic |
| JP2579193B2 (ja) * | 1988-07-19 | 1997-02-05 | 小野薬品工業株式会社 | １６，１６−ジフルオロ−１５−オキソ−１５−デオキシｐｇｅ誘導体 |
| CA2030345C (en) * | 1989-11-22 | 1998-12-08 | Ryuji Ueno | Use of 15-keto-prostaglandin compound for improvement of encephalic function |
| CA2039420C (en) | 1990-04-04 | 1996-12-10 | Ryuji Ueno | Treatment of cataract with 15-keto-prostaglandin compounds |
| CA2046069C (en) * | 1990-07-10 | 2002-04-09 | Ryuji Ueno | Treatment of inflammatory diseases with 15-keto-prostaglandin compounds |
| US5234858A (en) | 1990-11-16 | 1993-08-10 | Micron Technology, Inc. | Stacked surrounding wall capacitor |
| KR940007277B1 (ko) | 1992-02-14 | 1994-08-12 | 한국과학기술원 | 2차 전지 전극용 수소 저장 합금 |
| US5376034A (en) | 1992-05-27 | 1994-12-27 | Brunswick Corporation | Marine drive exhaust system |
| CA2150287C (en) | 1994-06-03 | 2004-08-10 | Ryuji Ueno | Agent for treating hepato-biliary diseases |
| JP3183615B2 (ja) * | 1994-06-03 | 2001-07-09 | 株式会社アールテック・ウエノ | 肝・胆道系疾患処置剤 |
| US6558708B1 (en) * | 1995-05-17 | 2003-05-06 | Cedars-Sinai Medical Center | Methods for manipulating upper gastrointestinal transit, blood flow, and satiety, and for treating visceral hyperalgesia |
| EP0857718B1 (en) | 1996-06-10 | 2002-08-14 | Sucampo AG | Endothelin antagonist |
| US5876034A (en) | 1997-12-17 | 1999-03-02 | Stafford; James R. | Sporting fishing board game |
| US6492417B1 (en) * | 1997-12-22 | 2002-12-10 | Alcon Manufacturing, Ltd. | 11-deoxy-16-fluoro-PGF2α analogs as FP receptor antagonists |
| US6610713B2 (en) * | 2000-05-23 | 2003-08-26 | North Shore - Long Island Jewish Research Institute | Inhibition of inflammatory cytokine production by cholinergic agonists and vagus nerve stimulation |
| US6414016B1 (en) | 2000-09-05 | 2002-07-02 | Sucampo, A.G. | Anti-constipation composition |
| US6919082B2 (en) * | 2001-02-13 | 2005-07-19 | Kirin Beer Kabushiki Kaisha | Pharmacological composition containing yeast cell wall fraction |
| GB2375349A (en) * | 2001-02-13 | 2002-11-13 | Glaxo Group Ltd | Chloride intracellular channel-related proteins |
| GB0111497D0 (en) * | 2001-05-11 | 2001-07-04 | Medical Res Council | Therapeutic methods |
| MXPA04002006A (es) * | 2001-08-31 | 2004-06-07 | Sucampo Ag | Analogos de prostagladina como abridor del canal de cloruro. |
| AR037524A1 (es) | 2001-11-14 | 2004-11-17 | Sucampo Ag | Unidad de dosificacion que comprende un analogo de prostaglandina para el tratamiento de la constipacion |
| US7732487B2 (en) | 2001-11-19 | 2010-06-08 | Sucampo Ag | Method for treating a disease or condition responsive to opening of C1C-2 channel |
| MXPA05006981A (es) * | 2002-12-27 | 2005-12-14 | Sucampo Ag | Derivados de prostaglandinas para el tratamiento de la molestia abdominal. |
| US7855226B2 (en) * | 2003-02-11 | 2010-12-21 | Allergan, Inc. | Treatment of inflammatory bowel disease |
| US7169807B2 (en) * | 2004-04-09 | 2007-01-30 | Allergan, Inc. | 10-Hydroxy-11-dihydroprostaglandin analogs as selective EP4 agonists |
| CA2585367A1 (en) * | 2004-10-26 | 2006-05-04 | Allergan, Inc. | Therapeutic and delivery methods of prostaglandin ep4 agonists |
| US20060281818A1 (en) * | 2005-03-21 | 2006-12-14 | Sucampo Ag, North Carolina State University | Method for treating mucosal disorders |
-
2006
- 2006-03-21 US US11/384,491 patent/US20060281818A1/en not_active Abandoned
- 2006-03-22 NZ NZ562351A patent/NZ562351A/en not_active IP Right Cessation
- 2006-03-22 JP JP2008502641A patent/JP5219797B2/ja not_active Expired - Fee Related
- 2006-03-22 KR KR1020077024144A patent/KR101456298B1/ko not_active Expired - Fee Related
- 2006-03-22 EP EP06730328.9A patent/EP1861169B1/en not_active Not-in-force
- 2006-03-22 WO PCT/JP2006/306380 patent/WO2006101244A2/en not_active Ceased
- 2006-03-22 AU AU2006225515A patent/AU2006225515B2/en not_active Ceased
- 2006-03-22 EP EP11170933.3A patent/EP2384791B1/en not_active Not-in-force
- 2006-03-22 MX MX2007011645A patent/MX2007011645A/es active IP Right Grant
- 2006-03-22 CA CA2601158A patent/CA2601158C/en not_active Expired - Fee Related
- 2006-03-22 CN CN201410192607.4A patent/CN103948603A/zh active Pending
- 2006-03-22 BR BRPI0609672-7A patent/BRPI0609672A2/pt active Search and Examination
- 2006-03-22 KR KR1020147010206A patent/KR20140072102A/ko not_active Ceased
- 2006-03-22 CA CA2831416A patent/CA2831416C/en not_active Expired - Fee Related
- 2006-03-22 EP EP11170921A patent/EP2384790A3/en not_active Withdrawn
- 2006-03-22 ES ES11170933.3T patent/ES2592283T3/es active Active
- 2006-03-22 NZ NZ597857A patent/NZ597857A/xx not_active IP Right Cessation
- 2006-03-22 NZ NZ588878A patent/NZ588878A/en not_active IP Right Cessation
-
2007
- 2007-09-10 IL IL185861A patent/IL185861A/en not_active IP Right Cessation
- 2007-10-19 NO NO20075361A patent/NO20075361L/no not_active Application Discontinuation
-
2012
- 2012-06-27 JP JP2012144537A patent/JP5777574B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| NO20075361L (no) | 2007-12-20 |
| CA2831416C (en) | 2016-12-13 |
| EP2384791A2 (en) | 2011-11-09 |
| IL185861A0 (en) | 2008-01-06 |
| IL185861A (en) | 2015-06-30 |
| EP2384791A3 (en) | 2011-12-28 |
| ES2592283T3 (es) | 2016-11-29 |
| JP2012180380A (ja) | 2012-09-20 |
| EP1861169B1 (en) | 2016-05-11 |
| KR20140072102A (ko) | 2014-06-12 |
| JP2008533195A (ja) | 2008-08-21 |
| CA2601158A1 (en) | 2006-09-28 |
| JP5777574B2 (ja) | 2015-09-09 |
| JP5219797B2 (ja) | 2013-06-26 |
| US20060281818A1 (en) | 2006-12-14 |
| WO2006101244A2 (en) | 2006-09-28 |
| MX2007011645A (es) | 2007-11-16 |
| AU2006225515B2 (en) | 2012-02-02 |
| KR20080012266A (ko) | 2008-02-11 |
| KR101456298B1 (ko) | 2014-11-03 |
| EP2384790A2 (en) | 2011-11-09 |
| WO2006101244A3 (en) | 2007-02-08 |
| AU2006225515A8 (en) | 2006-09-28 |
| NZ597857A (en) | 2013-08-30 |
| EP2384790A3 (en) | 2011-12-28 |
| CA2831416A1 (en) | 2006-09-28 |
| AU2006225515A1 (en) | 2006-09-28 |
| NZ588878A (en) | 2012-05-25 |
| NZ562351A (en) | 2010-12-24 |
| BRPI0609672A2 (pt) | 2010-04-20 |
| EP2384791B1 (en) | 2016-06-15 |
| CN103948603A (zh) | 2014-07-30 |
| EP1861169A2 (en) | 2007-12-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5777574B2 (ja) | 粘膜障害の処置のための方法および組成物 | |
| JP5427029B2 (ja) | 消化管の重炭酸分泌を促進するための方法および組成物 | |
| EP1871380B1 (en) | Combined use of prostaglandin compound and proton pump inhibitor for the treatment of gastrointestinal disorders | |
| RU2440338C2 (ru) | Способ и композиция для лечения заболеваний центральной нервной системы | |
| CN101180096B (zh) | 用于治疗粘膜疾病的方法和组合物 | |
| RU2445961C2 (ru) | Способ и композиция для лечения повреждений слизистых оболочек |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180322 |