CH623036A5 - - Google Patents

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Info

Publication number: CH623036A5
Authority: CH; Switzerland
Prior art keywords: group; prostadien; acid; ether; iir
Prior art date: 1975-05-26

Application number

CH640376A

Other languages

German (de)

English (en)

Inventor

Werner Dr Skuballa

Bernd Dr Raduechel

Helmut Dr Vorbrueggen

Walter Dr Elger

Eckehard Dr Schillinger

Olaf Dr Loge

Original Assignee

Schering Ag

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.)

1975-05-26

Filing date

1976-05-21

Publication date

1981-05-15

1975-05-26 Priority claimed from DE19752523676 external-priority patent/DE2523676A1/de

1976-04-12 Priority claimed from DE19762616304 external-priority patent/DE2616304A1/de

1976-05-21 Application filed by Schering Ag filed Critical Schering Ag

1981-05-15 Publication of CH623036A5 publication Critical patent/CH623036A5/de

Links

-1 hydroxymethylene group Chemical group 0.000 claims description 143
150000001875 compounds Chemical class 0.000 claims description 95
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
238000000034 method Methods 0.000 claims description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
230000032050 esterification Effects 0.000 claims description 11
238000005886 esterification reaction Methods 0.000 claims description 11
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
125000000468 ketone group Chemical group 0.000 claims description 9
238000005907 ketalization reaction Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
210000002307 prostate Anatomy 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
229910052721 tungsten Inorganic materials 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
229910052796 boron Inorganic materials 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
150000003457 sulfones Chemical class 0.000 claims 2
KPDBEGMTSLMZFK-LEWJYISDSA-N CCCCCCCC[C@H]1CCC(=O)[C@@H]1CCCC=CC=C(C)C Chemical compound CCCCCCCC[C@H]1CCC(=O)[C@@H]1CCCC=CC=C(C)C KPDBEGMTSLMZFK-LEWJYISDSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 163
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 60
239000012230 colorless oil Substances 0.000 description 60
239000000203 mixture Substances 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 51
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000741 silica gel Substances 0.000 description 36
229910002027 silica gel Inorganic materials 0.000 description 36
239000000243 solution Substances 0.000 description 34
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
229960000583 acetic acid Drugs 0.000 description 24
239000007983 Tris buffer Substances 0.000 description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
238000004587 chromatography analysis Methods 0.000 description 18
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000004809 thin layer chromatography Methods 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
235000011054 acetic acid Nutrition 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
238000001914 filtration Methods 0.000 description 12
239000012362 glacial acetic acid Substances 0.000 description 12
150000003180 prostaglandins Chemical class 0.000 description 12
230000000694 effects Effects 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
239000003921 oil Substances 0.000 description 11
239000007858 starting material Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
229940094443 oxytocics prostaglandins Drugs 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
230000003647 oxidation Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
229910052786 argon Inorganic materials 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000012267 brine Substances 0.000 description 7
239000012280 lithium aluminium hydride Substances 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
239000003810 Jones reagent Substances 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
ODPLDJPHIGPUBT-JWDFLIAJSA-N 2-[7-[(1R,2S)-2-octylcyclopentyl]hepta-1,3-dienoxy]oxane Chemical compound O1C(CCCC1)OC=CC=CCCC[C@H]1CCC[C@@H]1CCCCCCCC ODPLDJPHIGPUBT-JWDFLIAJSA-N 0.000 description 5
UXGJTLJRETWOMF-REQUTJCGSA-N 7-[(1R,2S)-2-octylcyclopentyl]-1-(oxan-2-yloxy)hepta-1,3-dien-1-ol Chemical compound O1C(CCCC1)OC(=CC=CCCC[C@H]1CCC[C@@H]1CCCCCCCC)O UXGJTLJRETWOMF-REQUTJCGSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 4
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
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 4
229910001958 silver carbonate Inorganic materials 0.000 description 4
239000012027 Collins reagent Substances 0.000 description 3
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
206010000210 abortion Diseases 0.000 description 3
231100000176 abortion Toxicity 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
150000001261 hydroxy acids Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
UKVVPDHLUHAJNZ-PMACEKPBSA-N prostane Chemical group CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC UKVVPDHLUHAJNZ-PMACEKPBSA-N 0.000 description 3
NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
210000004291 uterus Anatomy 0.000 description 3
RBFAFTFBJJWLCF-VQTJNVASSA-N (2R,3S)-2-octa-4,6-dienyl-3-octylcyclopentan-1-one Chemical compound CC=CC=CCCC[C@H]1C(CC[C@@H]1CCCCCCCC)=O RBFAFTFBJJWLCF-VQTJNVASSA-N 0.000 description 2
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 2
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
LXNAVEXFUKBNMK-UHFFFAOYSA-N acetic acid;palladium Chemical compound [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
238000010494 dissociation reaction Methods 0.000 description 2
230000005593 dissociations Effects 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical class OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000004043 oxo group Chemical group O=* 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000006884 silylation reaction Methods 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
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125000005208 trialkylammonium group Chemical group 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH640376A 1975-05-26 1976-05-21 CH623036A5 (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19752523676 DE2523676A1 (de)	1975-05-26	1975-05-26	Neue prostanderivate und verfahren zu ihrer herstellung
DE19762616304 DE2616304A1 (de)	1976-04-12	1976-04-12	Neue prostansaeurederivate und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CH623036A5 true CH623036A5 (nl)	1981-05-15

Family

ID=25768952

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH640376A CH623036A5 (nl)	1975-05-26	1976-05-21

Country Status (14)

Country	Link
US (2)	US4105792A (nl)
JP (1)	JPS51143643A (nl)
AT (1)	AT359657B (nl)
AU (1)	AU510695B2 (nl)
CA (1)	CA1091226A (nl)
CH (1)	CH623036A5 (nl)
DK (1)	DK229476A (nl)
FR (1)	FR2312240A1 (nl)
GB (1)	GB1553710A (nl)
HU (1)	HU177906B (nl)
IE (1)	IE44255B1 (nl)
LU (1)	LU75011A1 (nl)
NL (1)	NL7605381A (nl)
SE (1)	SE7605925L (nl)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4058564A (en) *	1976-07-26	1977-11-15	The Upjohn Company	Aliphatic 2-decarboxy-2-hydroxymethyl-13,14-didehydro-PG compounds
US4149006A (en) *	1977-01-24	1979-04-10	G. D. Searle & Co.	Prostaglandin derivatives having alkynyl, hydroxy and aryloxy junctions in the 2β side chain
US4171331A (en) *	1978-06-05	1979-10-16	Miles Laboratories, Inc.	1 And 2-substituted analogues of certain prostaglandins
DE3405181A1 (de) *	1984-02-10	1985-08-22	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue carbacycline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US5238961A (en) *	1990-06-14	1993-08-24	Allergan, Inc.	Pgf 1-alcohols and their use as ocular hypotensives
US5139491A (en) *	1990-12-06	1992-08-18	Allergan, Inc.	2-decarboxyl-2-alkoxyalkyl prostaglandins as ocular hypotensives
US5767154A (en) *	1991-02-07	1998-06-16	Allergan	5-trans-prostaglandins of the F series and their use as ocular hypotensives
WO1992013836A1 (en) *	1991-02-07	1992-08-20	Allergan, Inc.	2-decarboxyl-2-hydroxyalkyl-5-trans prostaglandin f derivatives
US5312832A (en) *	1991-05-17	1994-05-17	Allergan, Inc.	Ocular hypotensive 2-decarboxyl-2-acylthioalkyl prostaglandin derivatives
US5352708A (en) *	1992-09-21	1994-10-04	Allergan, Inc.	Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents
US5688819A (en) *	1992-09-21	1997-11-18	Allergan	Cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents
US5972991A (en)	1992-09-21	1999-10-26	Allergan	Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
US5834498A (en) *	1992-09-21	1998-11-10	Allergan	Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
US5385945A (en) *	1992-10-21	1995-01-31	Allergan, Inc.	7-(5-substituted cyclopentyl) and (5-substituted cyclopentenyl) heptyl alcohols, heptylamines and heptanoic acid amides, and method of lowering intraocular pressure in the eye of a mammal by administration of these novel compounds
US5510383A (en) *	1993-08-03	1996-04-23	Alcon Laboratories, Inc.	Use of cloprostenol, fluprostenol and their salts and esters to treat glaucoma and ocular hypertension
US6184250B1 (en)	1993-08-03	2001-02-06	Alcon Laboratories, Inc.	Use of cloprostenol and fluprostenol analogues to treat glaucoma and ocular hypertension
US5721273A (en)	1993-12-15	1998-02-24	Alcon Laboratories, Inc.	Use of certain 9-halo-13,14-dihydroprostaglandins to treat glaucoma and ocular hypertension
US5545665A (en) *	1993-12-28	1996-08-13	Allergan	Cyclopentane(ene) heptenoic or heptanoic acids and derivatives thereof useful as therapeutic agents
US7851504B2 (en)	2005-03-16	2010-12-14	Allergan, Inc.	Enhanced bimatoprost ophthalmic solution
US9241918B2 (en)	2005-03-16	2016-01-26	Allergan, Inc.	Enhanced bimatoprost ophthalmic solution
US9522153B2 (en)	2009-12-22	2016-12-20	Allergan, Inc.	Compositions and methods for lowering intraocular pressure

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3069322A (en) *	1958-05-28	1962-12-18	Bergstrom Sune	Pge and pgf
US3723528A (en) *	1967-10-09	1973-03-27	Upjohn Co	Prostaglandin oximes and oxime ethers
US3922293A (en) *	1971-12-30	1975-11-25	Upjohn Co	Prostaglandin F-type 9-monoacylates
GB1451798A (en) *	1973-08-02	1976-10-06	Ici Ltd	Prostanoic acid derivatives
GB1468830A (en) *	1974-01-26	1977-03-30	May & Baker Ltd	Cyclopentane derivatives
US3970685A (en) *	1974-06-05	1976-07-20	Syntex (U.S.A.) Inc.	(DL)-13-Substituted sulfinyl-prostaglandin-like compounds
US4117119A (en) *	1975-03-11	1978-09-26	Ono Pharmaceutical Company	15-cyclobutyl-prostaglandins

1976
- 1976-05-20 NL NL7605381A patent/NL7605381A/nl not_active Application Discontinuation
- 1976-05-21 AT AT373376A patent/AT359657B/de not_active IP Right Cessation
- 1976-05-21 CH CH640376A patent/CH623036A5/de not_active IP Right Cessation
- 1976-05-24 IE IE1084/76A patent/IE44255B1/en unknown
- 1976-05-24 LU LU75011A patent/LU75011A1/xx unknown
- 1976-05-24 AU AU14225/76A patent/AU510695B2/en not_active Expired
- 1976-05-25 GB GB21622/76A patent/GB1553710A/en not_active Expired
- 1976-05-25 SE SE7605925A patent/SE7605925L/xx unknown
- 1976-05-25 HU HU76SCHE566A patent/HU177906B/hu unknown
- 1976-05-25 US US05/689,849 patent/US4105792A/en not_active Expired - Lifetime
- 1976-05-25 DK DK229476A patent/DK229476A/da unknown
- 1976-05-26 CA CA253,389A patent/CA1091226A/en not_active Expired
- 1976-05-26 JP JP51061035A patent/JPS51143643A/ja active Pending
- 1976-05-26 FR FR7615918A patent/FR2312240A1/fr active Granted
1978
- 1978-03-02 US US05/882,687 patent/US4256745A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FR2312240A1 (fr)	1976-12-24
DK229476A (da)	1976-11-27
LU75011A1 (nl)	1977-01-20
CA1091226A (en)	1980-12-09
IE44255L (en)	1976-11-26
IE44255B1 (en)	1981-09-23
FR2312240B1 (nl)	1979-09-21
SE7605925L (sv)	1976-11-27
AU1422576A (en)	1977-12-01
HU177906B (en)	1982-01-28
US4105792A (en)	1978-08-08
AT359657B (de)	1980-11-25
NL7605381A (nl)	1976-11-30
US4256745A (en)	1981-03-17
JPS51143643A (en)	1976-12-10
AU510695B2 (en)	1980-07-10
ATA373376A (de)	1980-04-15
GB1553710A (en)	1979-09-26

Legal Events

Date	Code	Title	Description
1985-01-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0299914B1 (de)	1993-04-07	9-Halogen-(Z)-prostaglandinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
CH623036A5 (nl)	1981-05-15
EP0030377B1 (de)	1984-02-22	9-Chlor-prostaglandinderivate, Verfahren zur Herstellung und Verwendung als Arzneimittel
EP0069696B1 (de)	1986-01-15	9-Fluor-prostaglandinderivate, Verfahren zur Herstellung und Verwendung als Arzneimittel
CH637376A5 (de)	1983-07-29	Verfahren zur herstellung neuer prostansaeurederivate.
DE3048906A1 (de)	1982-07-15	Neue carbacycline, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0198829B1 (de)	1990-04-18	9-halogen-prostaglandinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
CH626876A5 (nl)	1981-12-15
DE2734791A1 (de)	1979-02-15	Neue prostaglandin-i tief 2 -derivate und verfahren zu ihrer herstellung
DE2753244A1 (de)	1979-06-07	Neue prostacyclinderivate und verfahren zu ihrer herstellung
CH638773A5 (en)	1983-10-14	Prostane derivatives and process for their preparation
WO1985000367A1 (en)	1985-01-31	11-halogene-prostane derivatives, process for obtaining them and utilization thereof as drugs
CH636082A5 (de)	1983-05-13	Prostanderivate, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel.
EP0069049B1 (de)	1986-05-21	Delta 8,9-Prostaglandinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
CH632492A5 (en)	1982-10-15	Process for preparing novel prostanoic acid derivatives
DE2523676A1 (de)	1976-12-16	Neue prostanderivate und verfahren zu ihrer herstellung
EP0153274B1 (de)	1990-05-16	Neue Carbacycline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE3116386A1 (de)	1982-07-01	Trans-(delta)(pfeil hoch)2(pfeil hoch)-pge-alkylsulfonylamide
US4159343A (en)	1979-06-26	Prostane derivatives
DE2640692C3 (de)	1979-09-13	Optisch aktive 5- (2-Carboxythiophen5-yl)-16phenoxy- a -tetranor- w tetranor-prostaglandine
EP0213129B1 (de)	1992-11-11	Neue 9-halogen-prostaglandine
DE2616304A1 (de)	1977-11-03	Neue prostansaeurederivate und verfahren zu ihrer herstellung
EP0081455B1 (de)	1986-04-09	9-Brom-prostaglandinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2508826A1 (de)	1976-09-09	Neue 1,3-benzodioxan-prostansaeurederivate und verfahren zu ihrer herstellung
CH641447A5 (en)	1984-02-29	Process for preparing prostanoic acid derivatives