AT395421B - Verfahren zur herstellung von neuen cyclopenthylethern - Google Patents

Verfahren zur herstellung von neuen cyclopenthylethern Download PDF

Info

Publication number: AT395421B
Authority: AT; Austria
Prior art keywords: oxy; pyran; tetrahydro; group; phenyl
Prior art date: 1985-04-23

Application number

AT0106986A

Other languages

German (de)

English (en)

Other versions

ATA106986A (de

Original Assignee

Glaxo Group Ltd

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.)

1985-04-23

Filing date

1986-04-22

Publication date

1992-12-28

1986-04-22 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1992-05-15 Publication of ATA106986A publication Critical patent/ATA106986A/de

1992-12-28 Application granted granted Critical

1992-12-28 Publication of AT395421B publication Critical patent/AT395421B/de

Links

150000002170 ethers Chemical class 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 126
-1 hydroxypropyl methyl Chemical group 0.000 claims description 76
239000000203 mixture Substances 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
238000000034 method Methods 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 2
239000002775 capsule Substances 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 8
229920002472 Starch Polymers 0.000 claims 4
235000019359 magnesium stearate Nutrition 0.000 claims 4
239000008107 starch Substances 0.000 claims 4
235000019698 starch Nutrition 0.000 claims 4
229920000168 Microcrystalline cellulose Polymers 0.000 claims 3
235000019813 microcrystalline cellulose Nutrition 0.000 claims 3
239000008108 microcrystalline cellulose Substances 0.000 claims 3
229940016286 microcrystalline cellulose Drugs 0.000 claims 3
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
230000006835 compression Effects 0.000 claims 1
238000007906 compression Methods 0.000 claims 1
239000007903 gelatin capsule Substances 0.000 claims 1
239000000463 material Substances 0.000 claims 1
229920000609 methyl cellulose Polymers 0.000 claims 1
239000001923 methylcellulose Substances 0.000 claims 1
235000010981 methylcellulose Nutrition 0.000 claims 1
238000010561 standard procedure Methods 0.000 claims 1
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 89
239000000543 intermediate Substances 0.000 description 68
239000000243 solution Substances 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
239000003480 eluent Substances 0.000 description 31
239000002904 solvent Substances 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
238000004587 chromatography analysis Methods 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
229910052739 hydrogen Inorganic materials 0.000 description 17
239000000377 silicon dioxide Substances 0.000 description 17
239000007787 solid Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
238000004458 analytical method Methods 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
UQDAEORWFCPQCU-UHFFFAOYSA-N acetic acid;oxolane;hydrate Chemical compound O.CC(O)=O.C1CCOC1 UQDAEORWFCPQCU-UHFFFAOYSA-N 0.000 description 13
239000002253 acid Substances 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
239000003921 oil Substances 0.000 description 8
238000001665 trituration Methods 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 7
239000000284 extract Substances 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
238000003756 stirring Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000001183 hydrocarbyl group Chemical group 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
125000005002 aryl methyl group Chemical group 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
238000010992 reflux Methods 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
208000007107 Stomach Ulcer Diseases 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
229910000365 copper sulfate Inorganic materials 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
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 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003166 prostaglandin E2 derivatives Chemical class 0.000 description 2
NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
239000003826 tablet Substances 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
NKVJKVMGJABKHV-UHFFFAOYSA-N 3-carboxypropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC(=O)O)C1=CC=CC=C1 NKVJKVMGJABKHV-UHFFFAOYSA-N 0.000 description 1
HLLSOEKIMZEGFV-UHFFFAOYSA-N 4-(dibutylsulfamoyl)benzoic acid Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 HLLSOEKIMZEGFV-UHFFFAOYSA-N 0.000 description 1
GIDLWOPUFGMILA-UHFFFAOYSA-N 4-(oxan-2-yloxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1OCCCC1 GIDLWOPUFGMILA-UHFFFAOYSA-N 0.000 description 1
OOKSYCBCCXZJHD-UHFFFAOYSA-N 7-(2-heptoxy-3-hydroxy-5-oxocyclopentyl)heptanoic acid Chemical compound CCCCCCCOC1C(O)CC(=O)C1CCCCCCC(O)=O OOKSYCBCCXZJHD-UHFFFAOYSA-N 0.000 description 1
KEXKSENTJFOUPR-UHFFFAOYSA-N 7-[2-[3-(4-fluorophenoxy)-2-hydroxypropoxy]-3-hydroxy-5-oxocyclopentyl]-2-(4-methoxyphenyl)hept-5-enoic acid Chemical compound COC1=CC=C(C=C1)C(CCC=CCC2C(C(CC2=O)O)OCC(COC3=CC=C(C=C3)F)O)C(=O)O KEXKSENTJFOUPR-UHFFFAOYSA-N 0.000 description 1
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101150046236 CNR1 gene Proteins 0.000 description 1
101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
102000011045 Chloride Channels Human genes 0.000 description 1
108010062745 Chloride Channels Proteins 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
241000792859 Enema Species 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
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125000004432 carbon atom Chemical group C* 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 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
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239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
229960002944 cyclofenil Drugs 0.000 description 1
BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical class C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000007920 enema Substances 0.000 description 1
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230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
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229960000905 indomethacin Drugs 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
150000007517 lewis acids Chemical class 0.000 description 1
230000004130 lipolysis Effects 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
QIVUHUKWYWGANJ-UHFFFAOYSA-N n-(4-hydroxyphenyl)-4-(oxan-2-yloxy)benzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C(C=C1)=CC=C1OC1OCCCC1 QIVUHUKWYWGANJ-UHFFFAOYSA-N 0.000 description 1
CVPWYDXAVJCNAG-UHFFFAOYSA-N n-(4-hydroxyphenyl)benzamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=CC=C1 CVPWYDXAVJCNAG-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
LBZIXWRZFXPLJU-UHFFFAOYSA-N propan-2-one;sulfuric acid Chemical compound CC(C)=O.OS(O)(=O)=O LBZIXWRZFXPLJU-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

AT0106986A 1985-04-23 1986-04-22 Verfahren zur herstellung von neuen cyclopenthylethern AT395421B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858510277A GB8510277D0 (en)	1985-04-23	1985-04-23	Carbocyclic compounds

Publications (2)

Publication Number	Publication Date
ATA106986A ATA106986A (de)	1992-05-15
AT395421B true AT395421B (de)	1992-12-28

Family

ID=10578043

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT0106986A AT395421B (de)	1985-04-23	1986-04-22	Verfahren zur herstellung von neuen cyclopenthylethern

Country Status (29)

Country	Link
JP (1)	JPS61249951A (no)
KR (1)	KR860008132A (no)
CN (1)	CN1011783B (no)
AT (1)	AT395421B (no)
AU (1)	AU593797B2 (no)
BE (1)	BE904656A (no)
CA (1)	CA1275094A (no)
CH (1)	CH667265A5 (no)
DE (1)	DE3613573A1 (no)
DK (1)	DK183986A (no)
ES (3)	ES8802137A1 (no)
FI (1)	FI85368C (no)
FR (1)	FR2580632B1 (no)
GB (2)	GB8510277D0 (no)
GR (1)	GR861060B (no)
HK (1)	HK51691A (no)
HU (1)	HU199411B (no)
IL (1)	IL78552A (no)
IT (1)	IT1190277B (no)
LU (1)	LU86404A1 (no)
MY (1)	MY100829A (no)
NL (1)	NL8601025A (no)
NO (1)	NO165069C (no)
NZ (1)	NZ215910A (no)
PH (1)	PH23597A (no)
PT (1)	PT82440B (no)
SE (1)	SE460193B (no)
SG (1)	SG92990G (no)
ZA (1)	ZA863006B (no)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0265247B1 (en) *	1986-10-22	1990-08-08	Glaxo Group Limited	Cyclopentyl ethers and their preparation and pharmaceutical formulation
GB8625322D0 (en) *	1986-10-22	1986-11-26	Glaxo Group Ltd	Chemical compounds
GB8625321D0 (en) *	1986-10-22	1986-11-26	Glaxo Group Ltd	Chemical compounds
GB8625325D0 (en) *	1986-10-22	1986-11-26	Glaxo Group Ltd	Chemical compounds
GB8625326D0 (en) *	1986-10-22	1986-11-26	Glaxo Group Ltd	Medicaments
US5231208A (en) *	1987-06-16	1993-07-27	Nissan Chemical Industries, Ltd.	Substituted cyclic ketones, substituted cyclic enones, and process for producing the same
US5254708A (en) *	1987-06-16	1993-10-19	Nissan Chemical Industries, Ltd.	Substituted cyclic ketones, substituted cyclic enones, and process for producing the same
US5227505A (en) *	1987-06-16	1993-07-13	Nissan Chemical Industries, Ltd.	Substituted cyclic ketones, substituted cyclic enones, and process for producing the same
JP2696933B2 (ja) *	1987-06-16	1998-01-14	日産化学工業株式会社	置換環状ケトン及び置換環状エノン並びにそれらの製造法
GB8822141D0 (en) *	1988-09-21	1988-10-26	Glaxo Group Ltd	Chemical compounds
AU1709699A (en)	1997-12-22	1999-07-12	Alcon Laboratories, Inc.	13-oxa prostaglandins for the treatment of glaucoma and ocular hypertension
JP4666257B2 (ja)	2003-07-25	2011-04-06	小野薬品工業株式会社	軟骨関連疾患治療剤

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0160495A2 (en) *	1984-04-24	1985-11-06	Glaxo Group Limited	Cyclopentyl ethers and their preparation and pharmaceutical formulation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ197729A (en) *	1980-08-12	1985-03-20	Sanofi Sa	13-oxaprostanoic acid derivatives and pharmaceutical compositions
GB2082176B (en) *	1980-08-12	1984-07-11	Sanofi Sa	Heteroprostaglandin derivatives and processes for preparing them

1985
- 1985-04-23 GB GB858510277A patent/GB8510277D0/en active Pending
1986
- 1986-04-21 IL IL78552A patent/IL78552A/xx not_active IP Right Cessation
- 1986-04-22 IT IT47919/86A patent/IT1190277B/it active
- 1986-04-22 AU AU56461/86A patent/AU593797B2/en not_active Ceased
- 1986-04-22 FI FI861687A patent/FI85368C/fi not_active IP Right Cessation
- 1986-04-22 CN CN86102778A patent/CN1011783B/zh not_active Expired
- 1986-04-22 NO NO861584A patent/NO165069C/no unknown
- 1986-04-22 ES ES554238A patent/ES8802137A1/es not_active Expired
- 1986-04-22 CA CA000507274A patent/CA1275094A/en not_active Expired - Fee Related
- 1986-04-22 BE BE0/216578A patent/BE904656A/fr not_active IP Right Cessation
- 1986-04-22 GR GR861060A patent/GR861060B/el unknown
- 1986-04-22 CH CH1622/86A patent/CH667265A5/de not_active IP Right Cessation
- 1986-04-22 SE SE8601852A patent/SE460193B/sv not_active IP Right Cessation
- 1986-04-22 LU LU86404A patent/LU86404A1/fr unknown
- 1986-04-22 NL NL8601025A patent/NL8601025A/nl not_active Application Discontinuation
- 1986-04-22 DK DK183986A patent/DK183986A/da not_active Application Discontinuation
- 1986-04-22 NZ NZ215910A patent/NZ215910A/xx unknown
- 1986-04-22 KR KR1019860003086A patent/KR860008132A/ko not_active Application Discontinuation
- 1986-04-22 ZA ZA863006A patent/ZA863006B/xx unknown
- 1986-04-22 PH PH33693A patent/PH23597A/en unknown
- 1986-04-22 DE DE19863613573 patent/DE3613573A1/de not_active Withdrawn
- 1986-04-22 AT AT0106986A patent/AT395421B/de not_active IP Right Cessation
- 1986-04-22 GB GB08609821A patent/GB2174702B/en not_active Expired
- 1986-04-22 PT PT82440A patent/PT82440B/pt not_active IP Right Cessation
- 1986-04-22 FR FR868605781A patent/FR2580632B1/fr not_active Expired
- 1986-04-23 JP JP61092446A patent/JPS61249951A/ja active Pending
- 1986-10-03 HU HU864173A patent/HU199411B/hu not_active IP Right Cessation
- 1986-12-30 MY MYPI86000259A patent/MY100829A/en unknown
1987
- 1987-08-12 ES ES557659A patent/ES8900044A1/es not_active Expired
1988
- 1988-04-12 ES ES557828A patent/ES9000022A1/es not_active Expired - Fee Related
1990
- 1990-11-15 SG SG929/90A patent/SG92990G/en unknown
1991
- 1991-07-04 HK HK516/91A patent/HK51691A/xx unknown

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0160495A2 (en) *	1984-04-24	1985-11-06	Glaxo Group Limited	Cyclopentyl ethers and their preparation and pharmaceutical formulation

Also Published As

Publication number	Publication date
AU5646186A (en)	1986-10-30
CN86102778A (zh)	1986-10-22
IT8647919A0 (it)	1986-04-22
HK51691A (en)	1991-07-12
ES557659A0 (es)	1988-11-16
CH667265A5 (de)	1988-09-30
IL78552A0 (en)	1986-08-31
DK183986D0 (da)	1986-04-22
IT1190277B (it)	1988-02-16
ATA106986A (de)	1992-05-15
ES8900044A1 (es)	1988-11-16
NO165069B (no)	1990-09-10
DE3613573A1 (de)	1986-10-30
HU199411B (en)	1990-02-28
ES554238A0 (es)	1988-04-01
NO165069C (no)	1990-12-19
AU593797B2 (en)	1990-02-22
HUT45010A (en)	1988-05-30
SE8601852L (sv)	1986-10-24
GB8609821D0 (en)	1986-05-29
FR2580632B1 (fr)	1989-09-15
BE904656A (fr)	1986-10-22
FI85368C (fi)	1992-04-10
DK183986A (da)	1986-10-24
NO861584L (no)	1986-10-24
PT82440B (pt)	1988-03-03
GB8510277D0 (en)	1985-05-30
ES9000022A1 (es)	1990-02-16
KR860008132A (ko)	1986-11-12
SE8601852D0 (sv)	1986-04-22
ZA863006B (en)	1986-12-30
GB2174702B (en)	1988-06-15
PH23597A (en)	1989-09-11
NL8601025A (nl)	1986-11-17
FR2580632A1 (fr)	1986-10-24
JPS61249951A (ja)	1986-11-07
ES557828A0 (es)	1990-02-16
FI861687A (fi)	1986-10-24
LU86404A1 (fr)	1986-11-05
SG92990G (en)	1991-01-18
FI85368B (fi)	1991-12-31
FI861687A0 (fi)	1986-04-22
ES8802137A1 (es)	1988-04-01
IL78552A (en)	1989-12-15
MY100829A (en)	1991-03-15
NZ215910A (en)	1989-08-29
CA1275094A (en)	1990-10-09
GB2174702A (en)	1986-11-12
GR861060B (en)	1986-08-25
PT82440A (en)	1986-05-01
SE460193B (sv)	1989-09-18
CN1011783B (zh)	1991-02-27

Legal Events

Date	Code	Title
1994-02-15	ELJ	Ceased due to non-payment of the annual fee
1995-03-15	UEP	Publication of translation of european patent specification
1998-07-15	REN	Ceased due to non-payment of the annual fee

Publication	Publication Date	Title
EP0185359B1 (de)	1991-12-04	Oxetanone
DE2731868C2 (no)	1987-06-04
DE69809268T2 (de)	2003-08-28	Aromatische c16-c20-substituierte tetrahydro-prostaglandine und ihre verwendung als prostaglandin f agonisten
CH648286A5 (de)	1985-03-15	Prostaglandinderivate, ihre herstellung und diese derivate enthaltende pharmazeutische zusammensetzungen.
AT395421B (de)	1992-12-28	Verfahren zur herstellung von neuen cyclopenthylethern
DE2355540C2 (de)	1982-11-18	16-Phenoxy-&omega;-tetranorprostaglandinderivate
DE60016181T2 (de)	2005-04-14	C-16 ungesätigte fp-selektive prostaglandin analoge
EP0133935A2 (de)	1985-03-13	p-Oxibenzoesäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Arzneimitteln mit hypolipämischer Wirkung
DE2721534A1 (de)	1977-12-15	Omega-nor-aromatische-13,14-dehydro-prostaglandine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische und veterinaermittel
DE2739277A1 (de)	1978-03-16	11-deoxy-11-oxaprostaglandinverbindungen
CH638510A5 (de)	1983-09-30	Prostacyclinanaloga.
DE69611303T2 (de)	2001-07-05	Benzolsulfonamidderivate, ihre herstellung und ihre therapeutische verwendung
DE2346706A1 (de)	1975-04-03	Neue, nicht natuerlich vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung
DE2610718A1 (de)	1976-10-14	Neue 16-phenoxy-prostaglandin-verbindungen
US4054604A (en)	1977-10-18	Amide derivatives of 9-oxo-13-trans-prostenoic acid
DE2644972C2 (de)	1986-06-19	Thiaprostansäurederivate, deren Herstellung und diese Verbindungen enthaltende Mittel
CH640847A5 (en)	1984-01-31	Process for preparing analogues of 5,6-dihydroprostacyclin
DE2945781A1 (de)	1980-06-12	Prostacyclinzwischenprodukte und protacyclinanaloge
EP0301401B1 (de)	1991-11-27	Leukotrienantagonisten, Verfahren zu ihrer Herstellung, ihre Anwendung zur Behandlung von Krankheiten
DE2737807A1 (de)	1978-03-09	C tief 1 -p-biphenylester von omega-pentanorprostaglandinen
CH623570A5 (no)	1981-06-15
CH634297A5 (de)	1983-01-31	Prostaglandin-analoga.
DE2359955A1 (de)	1975-06-05	Neue sulfide
DE2513371C2 (de)	1982-07-15	9,11,15-Trihydroxy-13-thia-5-prostensäure-Derivate und diese enthaltende pharmazeutische Zubereitungen
DE2331081A1 (de)	1975-01-23	Neue cyclopentanderivate und verfahren zu ihrer herstellung