NL8601025A - Cyclopentylethers en de bereiding daarvan en farmaceutisch preparaat. - Google Patents

Cyclopentylethers en de bereiding daarvan en farmaceutisch preparaat. Download PDF

Info

Publication number: NL8601025A
Authority: NL; Netherlands
Prior art keywords: hydroxy; phenyl; group; pyran; tetrahydro
Prior art date: 1985-04-23

Application number

NL8601025A

Other languages

English (en)

Dutch (nl)

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

1986-11-17

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

1986-11-17 Publication of NL8601025A publication Critical patent/NL8601025A/nl

Links

-1 CYCLOPENTYL ETHERS Chemical class 0.000 title claims description 163
238000002360 preparation method Methods 0.000 title claims description 9
239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 127
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 24
238000000034 method Methods 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
239000000460 chlorine Chemical group 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
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 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
229910052801 chlorine Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 3
150000003839 salts Chemical class 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
125000001589 carboacyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000543 intermediate Substances 0.000 description 94
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 55
239000000243 solution Substances 0.000 description 53
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
239000003480 eluent Substances 0.000 description 33
239000002904 solvent Substances 0.000 description 28
238000004587 chromatography analysis Methods 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000000377 silicon dioxide Substances 0.000 description 17
239000007787 solid Substances 0.000 description 16
YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
238000004458 analytical method Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
UQDAEORWFCPQCU-UHFFFAOYSA-N acetic acid;oxolane;hydrate Chemical compound O.CC(O)=O.C1CCOC1 UQDAEORWFCPQCU-UHFFFAOYSA-N 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
239000000284 extract Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 8
238000001665 trituration Methods 0.000 description 8
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
239000003826 tablet Substances 0.000 description 7
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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012267 brine Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
230000009467 reduction Effects 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 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 4
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
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
125000002924 primary amino group Chemical group [H]N([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
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
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
229920000168 Microcrystalline cellulose Polymers 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
229910000365 copper sulfate Inorganic materials 0.000 description 3
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
125000001183 hydrocarbyl group Chemical group 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
239000008108 microcrystalline cellulose Substances 0.000 description 3
229940016286 microcrystalline cellulose Drugs 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 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
229940086542 triethylamine Drugs 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-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
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
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
208000025865 Ulcer Diseases 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000005002 aryl methyl group Chemical group 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 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
230000015572 biosynthetic process Effects 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
239000002775 capsule Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical class C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 description 2
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 2
229960002986 dinoprostone Drugs 0.000 description 2
230000000694 effects Effects 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
150000008282 halocarbons Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 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
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 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
150000007522 mineralic acids Chemical class 0.000 description 2
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 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
125000004043 oxo group Chemical group O=* 0.000 description 2
238000007911 parenteral administration Methods 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
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
230000000630 rising effect Effects 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
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
231100000397 ulcer Toxicity 0.000 description 2
238000005406 washing Methods 0.000 description 2
125000002861 (C1-C4) alkanoyl group Chemical group 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
125000004326 2H-pyran-2-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])(*)O1 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 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
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 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
239000005711 Benzoic acid Substances 0.000 description 1
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 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
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000792859 Enema Species 0.000 description 1
241001529251 Gallinago gallinago Species 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
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000253387 Rhodobiaceae Species 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
239000000924 antiasthmatic agent Substances 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229950005228 bromoform Drugs 0.000 description 1
230000003182 bronchodilatating effect Effects 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
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
HFPGRVHMFSJMOL-UHFFFAOYSA-N dibromomethane Chemical compound Br[CH]Br HFPGRVHMFSJMOL-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000007907 direct compression Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940095399 enema Drugs 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
ICGWWCLWBPLPDF-UHFFFAOYSA-N furan-2-ol Chemical compound OC1=CC=CO1 ICGWWCLWBPLPDF-UHFFFAOYSA-N 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
YISNETVZEKWQMX-UHFFFAOYSA-N hepta-2,3-dienoic acid Chemical compound CCCC=C=CC(O)=O YISNETVZEKWQMX-UHFFFAOYSA-N 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
NZIHDZDYXNHUTA-UHFFFAOYSA-N heptanoic acid;pentane Chemical compound CCCCC.CCCCCCC(O)=O NZIHDZDYXNHUTA-UHFFFAOYSA-N 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
229960001340 histamine Drugs 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052741 iridium Inorganic materials 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
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
230000003902 lesion Effects 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 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
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
244000045947 parasite Species 0.000 description 1
MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 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
229960005235 piperonyl butoxide Drugs 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 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
230000008569 process Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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
239000012047 saturated solution Substances 0.000 description 1
230000028327 secretion 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
238000010561 standard procedure Methods 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
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229950005792 tenoate Drugs 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000004809 thin layer chromatography Methods 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
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
229910052727 yttrium Inorganic materials 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)

NL8601025A 1985-04-23 1986-04-22 Cyclopentylethers en de bereiding daarvan en farmaceutisch preparaat. NL8601025A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8510277		1985-04-23
GB858510277A GB8510277D0 (en)	1985-04-23	1985-04-23	Carbocyclic compounds

Publications (1)

Publication Number	Publication Date
NL8601025A true NL8601025A (nl)	1986-11-17

Family

ID=10578043

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8601025A NL8601025A (nl)	1985-04-23	1986-04-22	Cyclopentylethers en de bereiding daarvan en farmaceutisch preparaat.

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

Family Cites Families (3)

* 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
GB8410396D0 (en) *	1984-04-24	1984-05-31	Glaxo Group Ltd	Carbocyclic compounds

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

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
FR2580632A1 (fr)	1986-10-24
JPS61249951A (ja)	1986-11-07
ES557828A0 (es)	1990-02-16
AT395421B (de)	1992-12-28
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	Description
1993-06-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US7674921B2 (en)	2010-03-09	Internal 1,15-lactones of fluprostenol and related prostaglandin F2α analogs and their use in the treatment of glaucoma and intraocular hypertension
NL8601025A (nl)	1986-11-17	Cyclopentylethers en de bereiding daarvan en farmaceutisch preparaat.
IE48178B1 (en)	1984-10-17	Prostacyclin analogs
DE2659217A1 (de)	1977-07-21	Prostaglandin-analoga
HU211554A9 (en)	1995-12-28	Circulation-active dibenzo/1,5/dioxocin-5-ones
KR850000388B1 (ko)	1985-03-25	복소환 화합물 및 이의 이성체의 제조방법
EP0130142A1 (de)	1985-01-02	Neue Prostacyclinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
US4079145A (en)	1978-03-14	Certain pyrrolidone derivatives and pharmaceutical use thereof
JP2799865B2 (ja)	1998-09-21	フッ素化アラキドン酸誘導体類
EP0410241A1 (en)	1991-01-30	Aryl alkenoic acid derivatives as leukotriene antagonists
FR2515642A1 (fr)	1983-05-06	Nouvelles (11r)-11-deoxy-11-alkyl-6-oxo-prostaglandines et compositions pharmaceutiques les contenant
US4847370A (en)	1989-07-11	Cyclopentyl ethers and their preparation and pharmaceutical formulation
KR960001207B1 (ko)	1996-01-24	벤조디옥산 프로스타시클린 유사체
EP0265247B1 (en)	1990-08-08	Cyclopentyl ethers and their preparation and pharmaceutical formulation
US4824993A (en)	1989-04-25	Cyclopentyl ethers and their preparation and pharmaceutical formulation
US4851523A (en)	1989-07-25	Cyclopentyl ethers and their preparation and pharmaceutical formulation
EP0046597B1 (en)	1985-07-03	2,4-diazabicyclo(3.3.0)octane-3-one derivatives, their preparation and their pharmaceutical formulation
DD233997A5 (de)	1986-03-19	Verfahren zur herstellung von carbacyclinen
WO1992009573A2 (de)	1992-06-11	Cyclopentanetherderivate, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
EP0139515A2 (en)	1985-05-02	Novel bicyclooctane compounds and production thereof
PL150839B1 (pl)	1990-07-31	Sposób wytwarzania nowych eterów cyklopentylowych
JPS6134422B2 (no)	1986-08-07
EP0063338A1 (de)	1982-10-27	4-Oxo-PGI2-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende pharmazeutische Präparate
CS257299B2 (cs)	1988-04-15	Způsob výroby derivátů bicyklo[4.2,0]oktanů