TW209170B - - Google Patents

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Publication number: TW209170B
Authority: TW; Taiwan
Prior art keywords: keto; compound; group; dihydro; mono
Prior art date: 1990-05-01

Application number

TW080103357A

Other languages

English (en)

Chinese (zh)

Original Assignee

Kabushikaisha Ueno Seiyaku Oyo Kenkyujo

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

1990-05-01

Filing date

1991-04-30

Publication date

1993-07-11

1991-04-30 Application filed by Kabushikaisha Ueno Seiyaku Oyo Kenkyujo filed Critical Kabushikaisha Ueno Seiyaku Oyo Kenkyujo

1993-07-11 Application granted granted Critical

1993-07-11 Publication of TW209170B publication Critical patent/TW209170B/zh

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150000001875 compounds Chemical class 0.000 claims abstract description 122
239000000203 mixture Substances 0.000 claims description 88
125000000217 alkyl group Chemical group 0.000 claims description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
125000004429 atom Chemical group 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 24
206010033645 Pancreatitis Diseases 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 7
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
RGPBQGGBWIMGMA-BJMVGYQFSA-N 5-[(e)-[5-(4-bromophenyl)-6-hydroxy-3,6-dihydro-1,3,4-oxadiazin-2-ylidene]methyl]-1h-pyrimidine-2,4-dione Chemical compound OC1O\C(=C\C=2C(NC(=O)NC=2)=O)NN=C1C1=CC=C(Br)C=C1 RGPBQGGBWIMGMA-BJMVGYQFSA-N 0.000 claims 1
YAVVGPBYBUYPSR-UHFFFAOYSA-N benzene;oxygen Chemical group [O].C1=CC=CC=C1 YAVVGPBYBUYPSR-UHFFFAOYSA-N 0.000 claims 1
229940125898 compound 5 Drugs 0.000 claims 1
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208000016222 Pancreatic disease Diseases 0.000 abstract description 11
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239000011541 reaction mixture Substances 0.000 description 38
238000011049 filling Methods 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
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238000000034 method Methods 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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238000007796 conventional method Methods 0.000 description 20
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238000002309 gasification Methods 0.000 description 17
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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125000001424 substituent group Chemical group 0.000 description 10
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238000003786 synthesis reaction Methods 0.000 description 7
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241001465754 Metazoa Species 0.000 description 6
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239000012300 argon atmosphere Substances 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
239000002775 capsule Substances 0.000 description 6
CCNWZGXOWHXIJE-UHFFFAOYSA-N ethoxyethane;oxane Chemical compound CCOCC.C1CCOCC1 CCNWZGXOWHXIJE-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 5
229920000858 Cyclodextrin Polymers 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
238000010511 deprotection reaction Methods 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
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239000012046 mixed solvent Substances 0.000 description 5
238000012545 processing Methods 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
239000002699 waste material Substances 0.000 description 5
GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 4
FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
125000005907 alkyl ester group Chemical group 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
235000010357 aspartame Nutrition 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
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238000007254 oxidation reaction Methods 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
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 4
239000007858 starting material Substances 0.000 description 4
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DICZUTMNXOMHQD-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one Chemical compound C1CCC2OC(=O)CC21 DICZUTMNXOMHQD-UHFFFAOYSA-N 0.000 description 3
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KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
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125000000468 ketone group Chemical group 0.000 description 1
150000003903 lactic acid esters Chemical class 0.000 description 1
150000002596 lactones Chemical group 0.000 description 1
239000008141 laxative Substances 0.000 description 1
230000002475 laxative effect Effects 0.000 description 1
238000002386 leaching Methods 0.000 description 1
239000002502 liposome Substances 0.000 description 1
NRUBUZBAZRTHHX-UHFFFAOYSA-N lithium;propan-2-ylazanide Chemical compound [Li+].CC(C)[NH-] NRUBUZBAZRTHHX-UHFFFAOYSA-N 0.000 description 1
210000005229 liver cell Anatomy 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000002175 menstrual effect Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229960001252 methamphetamine Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
238000003801 milling Methods 0.000 description 1
235000013536 miso Nutrition 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
238000012856 packing Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
230000008855 peristalsis Effects 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068965 polysorbates 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
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
LTUDISCZKZHRMJ-UHFFFAOYSA-N potassium;hydrate Chemical compound O.[K] LTUDISCZKZHRMJ-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000035935 pregnancy 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
DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical group CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 1
LOLJEILMPWPILA-UHFFFAOYSA-N prostaglandin 15-keto-F2alpha Natural products CCCCCC(=O)C=CC1C(O)CC(O)C1CC=CCCCC(O)=O LOLJEILMPWPILA-UHFFFAOYSA-N 0.000 description 1
WGCXTGBZBFBQPP-UHFFFAOYSA-N prostaglandin E2 methyl ester Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(=O)OC WGCXTGBZBFBQPP-UHFFFAOYSA-N 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000006215 rectal suppository Substances 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
210000004761 scalp Anatomy 0.000 description 1
230000028327 secretion Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229940063675 spermine Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003457 sulfones Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
WBWWGRHZICKQGZ-HZAMXZRMSA-N taurocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 WBWWGRHZICKQGZ-HZAMXZRMSA-N 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000101 thioether group Chemical group 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000009284 tracheal contraction Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
DYVOLUUJJDFBFC-UHFFFAOYSA-N tripotassium butan-1-olate Chemical compound [K+].[K+].[K+].CCCC[O-].CCCC[O-].CCCC[O-] DYVOLUUJJDFBFC-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
230000025033 vasoconstriction Effects 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
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229910052726 zirconium Inorganic materials 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
- A61K31/557—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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

TW080103357A 1990-05-01 1991-04-30 TW209170B (2)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP11613990		1990-05-01

Publications (1)

Publication Number	Publication Date
TW209170B true TW209170B (2)	1993-07-11

Family

ID=14679704

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW080103357A TW209170B (2)	1990-05-01	1991-04-30

Country Status (7)

Country	Link
US (1)	US5164415A (2)
EP (1)	EP0455448B1 (2)
KR (1)	KR970005174B1 (2)
AT (1)	ATE174221T1 (2)
CA (1)	CA2041417C (2)
DE (1)	DE69130586T2 (2)
TW (1)	TW209170B (2)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU223345B1 (hu)	1995-12-20	2004-08-30	Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt.	Eljárás alfa, béta-telítetlen ketonok sztereoszelektív redukciójára
AU739343B2 (en) *	1997-11-28	2001-10-11	Sucampo Ag	Endothelin antagonist
TWI225398B (en) *	1999-07-14	2004-12-21	R Tech Ueno Ltd	Composition for treatment of external secretion disorders
BRPI0014869B8 (pt) *	1999-10-15	2021-05-25	Sucampo Ag	prostaglandinas bicíclicas, composições estabilizadas das mesmas, bem como processo para sua estabilização
EP1267883B1 (en) *	2000-04-06	2009-06-17	Sucampo AG	Bile secretion promoting composition for liver transplantation containing a 15-keto-prostaglandin
US6414016B1 (en)	2000-09-05	2002-07-02	Sucampo, A.G.	Anti-constipation composition
TWI302100B (en) *	2001-05-02	2008-10-21	Sucampo Ag	Composition for treating drug-induced constipation
ATE387204T1 (de) *	2001-05-18	2008-03-15	Sucampo Ag	Zusammensetzung mit induzierendem kathartischen effekt
EP1420794B1 (en) *	2001-08-31	2017-12-27	Sucampo AG	Prostaglandin analogs as chloride channel openers
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
TWI263505B (en) *	2001-11-19	2006-10-11	Sucampo Ag	Pharmaceutical composition comprising a C1C-2 channel opener
EP1575596B1 (en) *	2002-12-27	2016-06-22	Sucampo AG	Derivatives of prostaglandins for treating irritable bowel syndrome and/or functional dyspepsia
US20060073328A1 (en) *	2004-09-21	2006-04-06	Andover Coated Products, Inc.	Strapping system with non-elastic cohesive tape
EP1803809A3 (en) *	2005-08-12	2007-12-19	Abgenomics Corporation	Modulation of peroxisome proliferator-activated receptors
MX2008009650A (es)	2006-01-24	2008-11-06	R Tech Ueno Ltd	Formulacion de capsula de gelatina suave.
US20090082442A1 (en) *	2007-09-26	2009-03-26	Protia, Llc	Deuterium-enriched lubiprostone
KR101950386B1 (ko)	2018-12-26	2019-02-20	성신여자대학교 연구 산학협력단	15-케토 프로스타글란딘 e2를 유효성분으로 포함하는 암 치료용 약학 조성물
EP4039741B1 (en) *	2019-09-30	2024-11-20	Bridgestone Corporation	Rubber composition, rubber-metal composite, conveyor belt, hose, crawler, and tire

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Publication number	Priority date	Publication date	Assignee	Title
JPS58203911A (ja) *	1982-05-25	1983-11-28	Ono Pharmaceut Co Ltd	プロスタグランジン類似化合物を有効成分として含有する細肪障害治療剤
EP0153858A3 (en) *	1984-02-29	1985-12-11	The Upjohn Company	The therapeutic use of prostaglandins
DE3869471D1 (de) *	1987-05-15	1992-04-30	Ueno Seiyaku Oyo Kenkyujo Kk	Fiebersteigende zusammensetzung.
DE3850676T2 (de) *	1987-09-18	1994-11-03	Ueno Seiyaku Oyo Kenkyujo Kk	Hypotensive okulare Mittel.
JPH03101622A (ja) *	1989-09-11	1991-04-26	Green Cross Corp:The	肝炎予防治療剤
CA2027814C (en) *	1989-10-20	1996-07-30	Ryuji Ueno	Treatment of hepatobiliary disease with 15-keto-prostaglandin compounds

1991
- 1991-04-29 AT AT91303856T patent/ATE174221T1/de not_active IP Right Cessation
- 1991-04-29 DE DE69130586T patent/DE69130586T2/de not_active Expired - Lifetime
- 1991-04-29 EP EP91303856A patent/EP0455448B1/en not_active Expired - Lifetime
- 1991-04-29 CA CA002041417A patent/CA2041417C/en not_active Expired - Lifetime
- 1991-04-30 TW TW080103357A patent/TW209170B/zh not_active IP Right Cessation
- 1991-04-30 US US07/693,219 patent/US5164415A/en not_active Expired - Lifetime
- 1991-05-01 KR KR1019910007058A patent/KR970005174B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE69130586T2 (de)	1999-06-17
DE69130586D1 (de)	1999-01-21
CA2041417A1 (en)	1991-11-02
KR970005174B1 (ko)	1997-04-14
EP0455448A2 (en)	1991-11-06
EP0455448A3 (en)	1992-07-08
KR910019620A (ko)	1991-12-19
EP0455448B1 (en)	1998-12-09
US5164415A (en)	1992-11-17
CA2041417C (en)	2002-05-21
ATE174221T1 (de)	1998-12-15

Legal Events

Date	Code	Title	Description
2011-06-21	MK4A	Expiration of patent term of an invention patent

Publication	Publication Date	Title
TW209170B (2)	1993-07-11
CA2030345C (en)	1998-12-08	Use of 15-keto-prostaglandin compound for improvement of encephalic function
CN100335049C (zh)	2007-09-05	泻药组合物
KR20000070903A (ko)	2000-11-25	11,15-ｏ-디알킬프로스타글란딘 ｅ 유도체, 이것의 제조 방법 및 이것을 유효 성분으로 함유하는 약제
US5346921A (en)	1994-09-13	Treatment of inflammation with 15-keto-prostaglandin compounds
EP0366279A2 (en)	1990-05-02	Ocular hypotensive agents
IL287119B2 (en)	2023-07-01	Bryostatin compounds and methods for their preparation
TWI320711B (en)	2010-02-21	Cathartic composition
WO1994008959A1 (fr)	1994-04-28	Derive de prostaglandine
JPS59167567A (ja)	1984-09-21	４，４，５，５―テトラデヒドロ　ｐｇｅ↓１
RU2440338C2 (ru)	2012-01-20	Способ и композиция для лечения заболеваний центральной нервной системы
FR2887882A1 (fr)	2007-01-05	Derives de pyrido[2,3-d] pyrimidine, leur preparation, leur application en therapeutique
TW205508B (2)	1993-05-11
CA2030344C (en)	2000-04-18	Treatment of pulmonary dysfunction with 15-keto-prostaglandin compounds
FR2733498A1 (fr)	1996-10-31	Nouveaux composes cyclohexaniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
JPS6144819A (ja)	1986-03-04	プロスタグランジンｉ２類縁化合物を含有する循環改善作用を有する薬剤
JPS60222475A (ja)	1985-11-07	新規なプロスタサイクリン系化合物
JPS6032763A (ja)	1985-02-19	新規な１１−オキソプロスタン酸誘導体ならびにその利用
JPS58150583A (ja)	1983-09-07	新規なハロゲン化プロスタサイクリン類、それらの製造法およびそれらを活性成分とする薬学的組成物
WO1991013869A1 (fr)	1991-09-19	Derive de 15-desoxyprostaglandine
EP0172233A1 (en)	1986-02-26	Punaglandins and pharmaceutical use thereof
TW210288B (2)	1993-08-01
JPS61500551A (ja)	1986-03-27	２０−アルキル−７−オキソプロスタサイクリン誘導体及びその製法
JPH01104040A (ja)	1989-04-21	プロスタグランジンｄ類およびそれを含む鎮静・睡眠剤
JP2016533329A (ja)	2016-10-27	Δ１２−ｐｇｊ３および関連化合物の合成