LU80016A1 - Procede de preparation de nouvelles 4-pyrones substituees en positions 2,3 et 6 et medicament les contenant - Google Patents

Procede de preparation de nouvelles 4-pyrones substituees en positions 2,3 et 6 et medicament les contenant Download PDF

Info

Publication number: LU80016A1
Authority: LU; Luxembourg
Prior art keywords: group; methyl; chosen; formula; hydrogen atom
Prior art date: 1977-07-22

Application number

LU80016A

Other languages

English (en)

French (fr)

Inventor

J Plattner

D Kuhla

Original Assignee

Pfizer

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.)

1977-07-22

Filing date

1978-07-21

Publication date

1980-02-14

1978-07-21 Application filed by Pfizer filed Critical Pfizer

1980-02-14 Publication of LU80016A1 publication Critical patent/LU80016A1/fr

Links

238000002360 preparation method Methods 0.000 title claims description 28
238000000034 method Methods 0.000 title claims description 14
239000003814 drug Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 59
-1 lithium triethylborohydride Chemical group 0.000 claims description 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
230000002829 reductive effect Effects 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical group O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
239000002585 base Substances 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
125000000468 ketone group Chemical group 0.000 claims description 3
239000012312 sodium hydride Substances 0.000 claims description 3
229910000104 sodium hydride Inorganic materials 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
229910052725 zinc Inorganic materials 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
239000012279 sodium borohydride Substances 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims 4
229910052801 chlorine Inorganic materials 0.000 claims 2
229910052731 fluorine Inorganic materials 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
230000001476 alcoholic effect Effects 0.000 claims 1
150000004703 alkoxides Chemical class 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
230000001131 transforming effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 49
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
239000003921 oil Substances 0.000 description 21
235000019198 oils Nutrition 0.000 description 21
239000000203 mixture Substances 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
238000005481 NMR spectroscopy Methods 0.000 description 14
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical group O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
150000003180 prostaglandins Chemical class 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
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 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000012266 salt solution Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
239000011734 sodium Substances 0.000 description 9
229940094443 oxytocics prostaglandins Drugs 0.000 description 8
238000012360 testing method Methods 0.000 description 8
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 7
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
229940095074 cyclic amp Drugs 0.000 description 7
125000004122 cyclic group Chemical group 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000009471 action Effects 0.000 description 6
238000010828 elution Methods 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
239000002089 prostaglandin antagonist Substances 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
239000000725 suspension Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
MOHHRUXIPJXZBS-UHFFFAOYSA-N 3-hydroxy-2-(hydroxymethyl)pyran-4-one Chemical compound OCC=1OC=CC(=O)C=1O MOHHRUXIPJXZBS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
238000010586 diagram Methods 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000008241 heterogeneous mixture Substances 0.000 description 4
238000011534 incubation Methods 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 3
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000011097 chromatography purification Methods 0.000 description 3
YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 3
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 3
229960002986 dinoprostone Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010012735 Diarrhoea Diseases 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
208000010412 Glaucoma Diseases 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
230000002159 abnormal effect Effects 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000002552 dosage form Substances 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
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
JRUMBOAUJARDPP-UHFFFAOYSA-N ethyl 6-(2-formyl-4-oxopyran-3-yl)oxyhexanoate Chemical compound CCOC(=O)CCCCCOC1=C(C=O)OC=CC1=O JRUMBOAUJARDPP-UHFFFAOYSA-N 0.000 description 2
XXNMHBUHXVUOEL-OUKQBFOZSA-N ethyl 6-[2-[(e)-3-hydroxyoct-1-enyl]-4-oxopyran-3-yl]oxyhexanoate Chemical compound CCCCCC(O)\C=C\C=1OC=CC(=O)C=1OCCCCCC(=O)OCC XXNMHBUHXVUOEL-OUKQBFOZSA-N 0.000 description 2
ATYNTQMEUHOGJS-UHFFFAOYSA-N ethyl 6-[6-(2,2-dimethylpropanoyloxymethyl)-2-formyl-4-oxopyran-3-yl]oxyhexanoate Chemical compound CCOC(=O)CCCCCOC1=C(C=O)OC(COC(=O)C(C)(C)C)=CC1=O ATYNTQMEUHOGJS-UHFFFAOYSA-N 0.000 description 2
LTWOHZNXCOUWKH-UHFFFAOYSA-N ethyl 6-iodohexanoate Chemical compound CCOC(=O)CCCCCI LTWOHZNXCOUWKH-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000006698 induction Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
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229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
208000007056 sickle cell anemia Diseases 0.000 description 2
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
ONYIBVIIOCEBIV-UHFFFAOYSA-N 1-dimethoxyphosphoryl-4-phenylbutan-2-one Chemical compound COP(=O)(OC)CC(=O)CCC1=CC=CC=C1 ONYIBVIIOCEBIV-UHFFFAOYSA-N 0.000 description 1
MUXPPYATEKVUBJ-UHFFFAOYSA-N 2,2-diethylbutanoyl chloride Chemical compound CCC(CC)(CC)C(Cl)=O MUXPPYATEKVUBJ-UHFFFAOYSA-N 0.000 description 1
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NQOJWZRPLXJDPX-UHFFFAOYSA-N 2-methylpyran-4-one Chemical compound CC1=CC(=O)C=CO1 NQOJWZRPLXJDPX-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
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NVRVNSHHLPQGCU-UHFFFAOYSA-M 6-bromohexanoate Chemical compound [O-]C(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-M 0.000 description 1
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208000006386 Bone Resorption Diseases 0.000 description 1
OOKCZXGEYPSNIM-UHFFFAOYSA-N CC1=CC(=O)C=C(O)O1 Chemical compound CC1=CC(=O)C=C(O)O1 OOKCZXGEYPSNIM-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
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GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
241000212342 Sium Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
UYTJTEXIQKJGOJ-UHFFFAOYSA-N [5-hydroxy-6-(hydroxymethyl)-4-oxopyran-2-yl]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC1=CC(=O)C(O)=C(CO)O1 UYTJTEXIQKJGOJ-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
102000030621 adenylate cyclase Human genes 0.000 description 1
108060000200 adenylate cyclase Proteins 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004808 allyl alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
RVSGRNKUJJUAPV-UHFFFAOYSA-N benzo[d][1,2]benzoxazepine Chemical class O1N=CC2=CC=CC=C2C2=CC=CC=C12 RVSGRNKUJJUAPV-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
230000024279 bone resorption Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000002361 compost Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
MAQMEXSLUSZDQM-UHFFFAOYSA-N diethoxymethylbenzene Chemical compound CCOC(OCC)C1=CC=CC=C1 MAQMEXSLUSZDQM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
QFPWTGRKZQVEDN-UHFFFAOYSA-N ethyl 6-(4-oxopyran-2-yl)oxyhexanoate Chemical compound C(=O)(OCC)CCCCCOC=1OC=CC(C=1)=O QFPWTGRKZQVEDN-UHFFFAOYSA-N 0.000 description 1
OYNJGYDBRYDYDZ-UHFFFAOYSA-N ethyl 6-(4-oxopyran-3-yl)oxyhexanoate Chemical compound C(=O)(OCC)CCCCCOC1=COC=CC1=O OYNJGYDBRYDYDZ-UHFFFAOYSA-N 0.000 description 1
RQERSBOLCJWTNC-UHFFFAOYSA-N ethyl 6-[2-(hydroxymethyl)-4-oxopyran-3-yl]oxyhexanoate Chemical compound CCOC(=O)CCCCCOC1=C(CO)OC=CC1=O RQERSBOLCJWTNC-UHFFFAOYSA-N 0.000 description 1
KCZHOCVYGSFIJA-FOCLMDBBSA-N ethyl 6-[6-(2,2-dimethylpropanoyloxymethyl)-4-oxo-2-[(e)-3-oxooct-1-enyl]pyran-3-yl]oxyhexanoate Chemical compound CCCCCC(=O)\C=C\C=1OC(COC(=O)C(C)(C)C)=CC(=O)C=1OCCCCCC(=O)OCC KCZHOCVYGSFIJA-FOCLMDBBSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 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
208000037805 labour Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
229940100688 oral solution Drugs 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
239000002304 perfume Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
150000003112 potassium compounds Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

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

LU80016A 1977-07-22 1978-07-21 Procede de preparation de nouvelles 4-pyrones substituees en positions 2,3 et 6 et medicament les contenant LU80016A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81804377		1977-07-22
US05/818,043 US4132847A (en)	1977-07-22	1977-07-22	4-Pyrone prostaglandin antagonists

Publications (1)

Publication Number	Publication Date
LU80016A1 true LU80016A1 (fr)	1980-02-14

Family

ID=25224503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU80016A LU80016A1 (fr)	1977-07-22	1978-07-21	Procede de preparation de nouvelles 4-pyrones substituees en positions 2,3 et 6 et medicament les contenant

Country Status (11)

Country	Link
US (1)	US4132847A (da)
JP (3)	JPS5814435B2 (da)
BE (1)	BE869166A (da)
DE (1)	DE2831761C2 (da)
DK (1)	DK148538C (da)
FR (2)	FR2398067A1 (da)
GB (2)	GB2001639B (da)
IE (1)	IE47035B1 (da)
IT (1)	IT1099579B (da)
LU (1)	LU80016A1 (da)
NL (1)	NL173750C (da)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0138523Y2 (da) *	1981-01-31	1989-11-17
JPS5834046U (ja) *	1981-08-31	1983-03-05	株式会社明電舎	溶存酸素計
US4442089A (en) *	1982-07-06	1984-04-10	E. R. Squibb & Sons, Inc.	Method for treating glaucoma with topical or systemic ACE inhibitor compositions
CA2113787A1 (en) *	1993-01-29	1994-07-30	Nobuyuki Hamanaka	Carbocyclic sulfonamides
HN1996000101A (es)	1996-02-28	1997-06-26	Inc Pfizer	Terapia combinada para la osteoporosis
WO1998050024A1 (en) *	1997-05-09	1998-11-12	The Mount Sinai School Of Medicine Of The City University Of New York	8-iso-prostaglandins for glaucoma therapy
US20020161026A1 (en) *	2000-11-07	2002-10-31	Paralkar Vishwas M.	Combination therapies for the stimulation of bone growth
US20030220377A1 (en) *	2002-05-08	2003-11-27	Richard Chesworth	Indole compounds and their use as estrogen agonists/antagonists
US20040002524A1 (en) *	2002-06-24	2004-01-01	Richard Chesworth	Benzimidazole compounds and their use as estrogen agonists/antagonists
US20050119262A1 (en) *	2003-08-21	2005-06-02	Pharmacia Corporation	Method for preventing or treating an optic neuropathy with a cox-2 inhibitor and an intraocular pressure reducing agent
BRPI0807942A2 (pt)	2007-02-16	2014-07-01	Ono Pharmaceutical Co	Agente terapêutico para distúrbio de excreção urinária
US12589097B2 (en)	2018-02-21	2026-03-31	OrphAl Therapeutics Inc.	Apilimod compositions and methods of use
TW202000205A (zh)	2018-02-21	2020-01-01	美商Ａｉ治療公司	使用阿吡莫德與麩胺酸性劑的組合治療

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3468916A (en) *	1966-11-01	1969-09-23	Pfizer & Co C	2-vinylpyromeconic acid

1977
- 1977-07-22 US US05/818,043 patent/US4132847A/en not_active Expired - Lifetime
1978
- 1978-07-17 GB GB787830084A patent/GB2001639B/en not_active Expired
- 1978-07-17 GB GB8030734A patent/GB2055375B/en not_active Expired
- 1978-07-19 DE DE2831761A patent/DE2831761C2/de not_active Expired
- 1978-07-20 BE BE189412A patent/BE869166A/xx not_active IP Right Cessation
- 1978-07-21 IT IT25999/78A patent/IT1099579B/it active
- 1978-07-21 JP JP53089284A patent/JPS5814435B2/ja not_active Expired
- 1978-07-21 DK DK326378A patent/DK148538C/da not_active IP Right Cessation
- 1978-07-21 FR FR7821682A patent/FR2398067A1/fr active Granted
- 1978-07-21 LU LU80016A patent/LU80016A1/fr unknown
- 1978-07-21 IE IE1471/78A patent/IE47035B1/en not_active IP Right Cessation
- 1978-07-21 NL NLAANVRAGE7807803,A patent/NL173750C/xx not_active IP Right Cessation
- 1978-08-31 JP JP10692878A patent/JPS54160382A/ja active Granted
- 1978-08-31 JP JP10692978A patent/JPS54160383A/ja active Granted
- 1978-12-04 FR FR7834071A patent/FR2401147A1/fr active Granted

Also Published As

Publication number	Publication date
FR2398067A1 (fr)	1979-02-16
FR2398067B1 (da)	1980-06-06
FR2401147A1 (fr)	1979-03-23
GB2055375B (en)	1982-08-11
JPS5814435B2 (ja)	1983-03-18
NL7807803A (nl)	1979-01-24
GB2001639A (en)	1979-02-07
US4132847A (en)	1979-01-02
JPS5424876A (en)	1979-02-24
JPS54160382A (en)	1979-12-19
IE47035B1 (en)	1983-11-30
DK326378A (da)	1979-01-23
BE869166A (fr)	1979-01-22
NL173750B (nl)	1983-10-03
DK148538C (da)	1986-01-13
NL173750C (nl)	1984-03-01
GB2001639B (en)	1982-03-17
IE781471L (en)	1979-01-22
FR2401147B1 (da)	1981-08-28
DK148538B (da)	1985-07-29
JPS54160383A (en)	1979-12-19
GB2055375A (en)	1981-03-04
JPS5730109B2 (da)	1982-06-26
IT7825999A0 (it)	1978-07-21
DE2831761A1 (de)	1979-01-25
IT1099579B (it)	1985-09-18
DE2831761C2 (de)	1984-12-13
JPS5730110B2 (da)	1982-06-26

Publication	Publication Date	Title
LU80016A1 (fr)	1980-02-14	Procede de preparation de nouvelles 4-pyrones substituees en positions 2,3 et 6 et medicament les contenant
EP0061386B1 (fr)	1984-06-20	Acides ((2-oxo-3-tétrahydrothiénylcarbamoyl)-alkylthio) acétiques, leurs sels et leurs esters, leur procédé de préparation et les compositions pharmaceutiques en contenant
EP0013960B1 (de)	1982-11-03	Substituierte Acetophenone, diese enthaltende Präparate und Verfahren zu deren Herstellung
EP0051917B1 (en)	1986-02-19	Benzofuran ethanolamine derivatives, processes for their preparation, and their use in medicine
US4341793A (en)	1982-07-27	Secondary amines and their use in pharmaceutical compositions
US4829081A (en)	1989-05-09	Analogs of mevalonolactone and derivatives thereof
EP0202759A2 (en)	1986-11-26	Leukotriene antagonists
US4219483A (en)	1980-08-26	4-Pyrone prostaglandin antagonists
CH619691A5 (da)	1980-10-15
EP0256936A1 (fr)	1988-02-24	Nouveaux dérivés de la benzyl-4 pipérazine, leur préparation et les compositions pharmaceutiques qui les contiennent
FR2492378A1 (fr)	1982-04-23	Derives de type 6h-dibenzo(b,d) pyranne 6-substitues utiles notamment comme medicaments antiulcereux, immunomodulateurs et antiviraux et procedes de leur preparation
FR2568248A1 (fr)	1986-01-31	Nouveaux composes naphtaleniques, leur preparation et leur application comme medicaments
HU211554A9 (en)	1995-12-28	Circulation-active dibenzo/1,5/dioxocin-5-ones
CH624934A5 (da)	1981-08-31
US4772625A (en)	1988-09-20	1,3-dioxan-5-yl-hexenoic acids
EP0723969A1 (de)	1996-07-31	Phosphonocarbonsäure-Derivate und deren Verwendung zur Behandlung von degenerativen Gelenkserkrankungen
EP0071175B1 (de)	1986-03-12	Phenylalkyloxirancarbonsäuren, Verfahren zu ihrer Herstellung, ihre Anwendung und sie enthaltende Arzneimittel
FR2515642A1 (fr)	1983-05-06	Nouvelles (11r)-11-deoxy-11-alkyl-6-oxo-prostaglandines et compositions pharmaceutiques les contenant
DE2737807A1 (de)	1978-03-09	C tief 1 -p-biphenylester von omega-pentanorprostaglandinen
DE2709347A1 (de)	1977-09-15	Erythro-15,16-dioxyprostensaeuren und -ester sowie verfahren zu ihrer herstellung
FR2488604A1 (fr)	1982-02-19	Derives d'heteroprostaglandines ainsi que leurs procedes de preparation
HU199412B (en)	1990-02-28	Process for producing fluorinated arachidonic acid derivatives and pharmaceutical compositions containing them as active components
LU79801A1 (fr)	1980-01-22	Procede de preparation de nouveaux derives substitues en position 15 d'w-pentanorprostaglandine
EP0049144B1 (en)	1984-08-29	5-fluoro uracil derivatives
FR2510567A1 (fr)	1983-02-04	Isomere optique du 11a, 15-dihydroxy 16-methoxy-16-methyl-prosta 13 (e)-ene-1-oate de methyle, utile notamment comme agent gastroprotecteur et son procede de preparation