CH617676A5 - - Google Patents

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Publication number: CH617676A5
Authority: CH; Switzerland
Prior art keywords: group; formula; carbon atoms; compound; hydrogen
Prior art date: 1974-06-04

Application number

CH707975A

Other languages

German (de)

English (en)

Inventor

Ulrich Dr Lerch

Milos Dr Babej

Wilhelm Dr Bartmann

Rudolf Dr Kunstmann

Original Assignee

Hoechst 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.)

1974-06-04

Filing date

1975-06-02

Publication date

1980-06-13

1975-06-02 Application filed by Hoechst Ag filed Critical Hoechst Ag

1980-06-13 Publication of CH617676A5 publication Critical patent/CH617676A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 46
-1 cycloaliphatic Chemical group 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 29
238000000034 method Methods 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 12
125000001931 aliphatic group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
238000006266 etherification reaction Methods 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229910052720 vanadium Inorganic materials 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 3
238000005917 acylation reaction Methods 0.000 claims description 3
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
241000251730 Chondrichthyes Species 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
125000004430 oxygen atom Chemical group O* 0.000 claims 2
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
125000004494 ethyl ester group Chemical group 0.000 description 12
150000003180 prostaglandins Chemical class 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
UWSJCCUODNDXOT-UHFFFAOYSA-N ethyl cyclopentanecarboxylate Chemical compound CCOC(=O)C1CCCC1 UWSJCCUODNDXOT-UHFFFAOYSA-N 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 9
229940094443 oxytocics prostaglandins Drugs 0.000 description 9
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
239000002904 solvent Substances 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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 class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
239000012298 atmosphere Substances 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
230000008602 contraction Effects 0.000 description 2
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
150000001940 cyclopentanes Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
DOHXWGGZBYKKHA-UHFFFAOYSA-N ethyl 7-iodo-6-methylheptanoate Chemical compound CCOC(=O)CCCCC(C)CI DOHXWGGZBYKKHA-UHFFFAOYSA-N 0.000 description 2
210000003405 ileum Anatomy 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
210000002460 smooth muscle Anatomy 0.000 description 2
230000003033 spasmogenic effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
210000004291 uterus Anatomy 0.000 description 2
NXWYAHLLQFLYDY-ZETCQYMHSA-N (2s)-2-(diethylamino)pentanedioic acid Chemical compound CCN(CC)[C@H](C(O)=O)CCC(O)=O NXWYAHLLQFLYDY-ZETCQYMHSA-N 0.000 description 1
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 1
JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
RELCLXLYMTZGCF-UHFFFAOYSA-N C(C)OC(CC(CI)C)=O.C(C)OC(C(CCCI)CC)=O Chemical compound C(C)OC(CC(CI)C)=O.C(C)OC(C(CCCI)CC)=O RELCLXLYMTZGCF-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 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
229910000019 calcium carbonate Inorganic materials 0.000 description 1
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
HNYBJHSDNWSBDU-UHFFFAOYSA-N carbonic acid;cyclopentane Chemical compound OC(O)=O.C1CCCC1 HNYBJHSDNWSBDU-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
238000007865 diluting Methods 0.000 description 1
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 1
229960002986 dinoprostone Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
FHGRPBSDPBRTLS-ONEGZZNKSA-N ethyl (e)-4-bromobut-2-enoate Chemical compound CCOC(=O)\C=C\CBr FHGRPBSDPBRTLS-ONEGZZNKSA-N 0.000 description 1
NAGCUTXHKKRLEE-XQRVVYSFSA-N ethyl (z)-7-iodohept-5-enoate Chemical compound CCOC(=O)CCC\C=C/CI NAGCUTXHKKRLEE-XQRVVYSFSA-N 0.000 description 1
OUMBMFMVAXFDPS-UHFFFAOYSA-N ethyl 2-(3-iodopropoxy)acetate Chemical compound CCOC(=O)COCCCI OUMBMFMVAXFDPS-UHFFFAOYSA-N 0.000 description 1
TWBZBLRWDYAYSD-UHFFFAOYSA-N ethyl 2-(3-iodopropoxy)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCCI TWBZBLRWDYAYSD-UHFFFAOYSA-N 0.000 description 1
HEARDJLCPYBIHY-UHFFFAOYSA-N ethyl 2-(3-iodopropyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CCCI HEARDJLCPYBIHY-UHFFFAOYSA-N 0.000 description 1
UIJQPBUGDJSVFL-UHFFFAOYSA-N ethyl 2-(4-iodobutoxy)acetate Chemical compound CCOC(=O)COCCCCI UIJQPBUGDJSVFL-UHFFFAOYSA-N 0.000 description 1
QUUFPXKCRKQRQF-UHFFFAOYSA-N ethyl 2-(4-iodobutyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CCCCI QUUFPXKCRKQRQF-UHFFFAOYSA-N 0.000 description 1
ODBGKBWQAKXFIU-UHFFFAOYSA-N ethyl 3-(2-iodoethoxy)benzoate Chemical compound CCOC(=O)C1=CC=CC(OCCI)=C1 ODBGKBWQAKXFIU-UHFFFAOYSA-N 0.000 description 1
XZZDVSAQTDAMLA-UHFFFAOYSA-N ethyl 3-[3-(bromomethyl)phenyl]propanoate Chemical compound CCOC(=O)CCC1=CC=CC(CBr)=C1 XZZDVSAQTDAMLA-UHFFFAOYSA-N 0.000 description 1
RDYHQEDCLHYJBY-UHFFFAOYSA-N ethyl 4-(2-iodoethoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(OCCI)C=C1 RDYHQEDCLHYJBY-UHFFFAOYSA-N 0.000 description 1
GURMVCKYMFVFHA-UHFFFAOYSA-N ethyl 4-(3-iodopropoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(OCCCI)C=C1 GURMVCKYMFVFHA-UHFFFAOYSA-N 0.000 description 1
GXANORVTQGAGCE-UHFFFAOYSA-N ethyl 4-(3-iodopropyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CCCI)C=C1 GXANORVTQGAGCE-UHFFFAOYSA-N 0.000 description 1
TWQLMAJROCNXEA-UHFFFAOYSA-N ethyl 4-(bromomethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CBr)C=C1 TWQLMAJROCNXEA-UHFFFAOYSA-N 0.000 description 1
DMKKSWBNCUUYSP-UHFFFAOYSA-N ethyl 4-[2-(bromomethyl)phenyl]butanoate Chemical compound CCOC(=O)CCCC1=CC=CC=C1CBr DMKKSWBNCUUYSP-UHFFFAOYSA-N 0.000 description 1
DCQBTVAXKZOCPY-UHFFFAOYSA-N ethyl 4-[3-(bromomethyl)phenyl]butanoate Chemical compound CCOC(=O)CCCC1=CC=CC(CBr)=C1 DCQBTVAXKZOCPY-UHFFFAOYSA-N 0.000 description 1
XEHUKUJAKYVNST-UHFFFAOYSA-N ethyl 5-ethyl-7-iodoheptanoate Chemical compound CCOC(=O)CCCC(CC)CCI XEHUKUJAKYVNST-UHFFFAOYSA-N 0.000 description 1
ZMWTYBNGMOFAKH-UHFFFAOYSA-N ethyl 7-iodo-3-methylheptanoate Chemical compound CCOC(=O)CC(C)CCCCI ZMWTYBNGMOFAKH-UHFFFAOYSA-N 0.000 description 1
SRTPSJHUBPEFKO-UHFFFAOYSA-N ethyl 7-iodo-4-methylheptanoate Chemical compound CCOC(=O)CCC(C)CCCI SRTPSJHUBPEFKO-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
150000002366 halogen compounds Chemical class 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
150000004678 hydrides Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 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
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
BBMCPEOFGAIHQK-HWKANZROSA-N methyl (e)-4-bromo-3-methylbut-2-enoate Chemical compound COC(=O)\C=C(/C)CBr BBMCPEOFGAIHQK-HWKANZROSA-N 0.000 description 1
PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
229910001925 ruthenium oxide Inorganic materials 0.000 description 1
WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910000018 strontium carbonate Inorganic materials 0.000 description 1
UBXAKNTVXQMEAG-UHFFFAOYSA-L strontium sulfate Inorganic materials [Sr+2].[O-]S([O-])(=O)=O UBXAKNTVXQMEAG-UHFFFAOYSA-L 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

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

Landscapes

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

CH707975A 1974-06-04 1975-06-02 CH617676A5 (es)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742426853 DE2426853A1 (de)	1974-06-04	1974-06-04	Neue cyclopentanderivate und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CH617676A5 true CH617676A5 (es)	1980-06-13

Family

ID=5917243

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH707975A CH617676A5 (es)	1974-06-04	1975-06-02

Country Status (17)

Country	Link
US (1)	US4078081A (es)
JP (1)	JPS516948A (es)
AT (1)	AT351685B (es)
AU (1)	AU8178975A (es)
BE (1)	BE829865A (es)
CA (1)	CA1064922A (es)
CH (1)	CH617676A5 (es)
DE (1)	DE2426853A1 (es)
DK (1)	DK246375A (es)
ES (2)	ES437058A1 (es)
FR (1)	FR2273528A1 (es)
GB (1)	GB1515315A (es)
IE (1)	IE41834B1 (es)
IL (1)	IL47402A0 (es)
LU (1)	LU72628A1 (es)
NL (1)	NL7506452A (es)
SE (1)	SE7506406L (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4991088U (es) *	1972-11-30	1974-08-07
US4097496A (en) *	1973-06-19	1978-06-27	Hoechst Aktiengesellschaft	Novel cyclopentane derivatives
JPH0632905Y2 (ja) *	1987-06-23	1994-08-31	株式会社四国製作所	可撓性スクリュ−コンベアの着脱支持装置
JPH0632904Y2 (ja) *	1987-06-23	1994-08-31	株式会社四国製作所	穀粒搬送装置の穀粒取出装置
JPS647116U (es) *	1987-06-29	1989-01-17

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2346706A1 (de) *	1973-09-17	1975-04-03	Hoechst Ag	Neue, nicht natuerlich vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung

1974
- 1974-06-04 DE DE19742426853 patent/DE2426853A1/de not_active Withdrawn
1975
- 1975-04-26 ES ES437058A patent/ES437058A1/es not_active Expired
- 1975-05-30 NL NL7506452A patent/NL7506452A/xx not_active Application Discontinuation
- 1975-06-02 US US05/582,927 patent/US4078081A/en not_active Expired - Lifetime
- 1975-06-02 LU LU72628A patent/LU72628A1/xx unknown
- 1975-06-02 CH CH707975A patent/CH617676A5/de not_active IP Right Cessation
- 1975-06-02 IL IL47402A patent/IL47402A0/xx unknown
- 1975-06-02 DK DK246375A patent/DK246375A/da unknown
- 1975-06-03 AT AT420475A patent/AT351685B/de not_active IP Right Cessation
- 1975-06-03 CA CA228,403A patent/CA1064922A/en not_active Expired
- 1975-06-03 IE IE1225/75A patent/IE41834B1/en unknown
- 1975-06-03 AU AU81789/75A patent/AU8178975A/en not_active Expired
- 1975-06-04 SE SE7506406A patent/SE7506406L/xx unknown
- 1975-06-04 BE BE157031A patent/BE829865A/xx unknown
- 1975-06-04 FR FR7517440A patent/FR2273528A1/fr active Granted
- 1975-06-04 JP JP50067408A patent/JPS516948A/ja active Pending
- 1975-06-04 GB GB24170/75A patent/GB1515315A/en not_active Expired
1976
- 1976-12-16 ES ES454307A patent/ES454307A1/es not_active Expired

Also Published As

Publication number	Publication date
GB1515315A (en)	1978-06-21
AU8178975A (en)	1976-12-09
IE41834L (en)	1975-12-04
US4078081A (en)	1978-03-07
BE829865A (fr)	1975-12-04
DE2426853A1 (de)	1976-01-02
CA1064922A (en)	1979-10-23
ATA420475A (de)	1979-01-15
IE41834B1 (en)	1980-04-09
ES437058A1 (es)	1977-05-01
AT351685B (de)	1979-08-10
ES454307A1 (es)	1977-12-01
SE7506406L (sv)	1975-12-05
FR2273528B1 (es)	1979-08-10
NL7506452A (nl)	1975-12-08
DK246375A (da)	1975-12-05
JPS516948A (es)	1976-01-20
IL47402A0 (en)	1975-08-31
LU72628A1 (es)	1977-03-03
FR2273528A1 (fr)	1976-01-02

Legal Events

Date	Code	Title	Description
1982-02-26	PL	Patent ceased

Publication	Publication Date	Title
DE2355731C3 (de)	1981-01-15	Derivate von w -nor-Prostaglandinen- E2IUId -F2 a , Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen Pfizer Ine, New York, N.Y. (YStA.)
DE2723237A1 (de)	1977-12-15	12-azaprostansaeuren
CH623809A5 (en)	1981-06-30	Process for the preparation of pyrrolidones
CH617676A5 (es)	1980-06-13
CH644580A5 (de)	1984-08-15	Cyclohexen-derivate.
DE3006865A1 (de)	1981-09-10	Hetero-imino-prostacycline
DE2422924A1 (de)	1975-11-27	Thiaprostaglandine
CH634831A5 (en)	1983-02-28	Process for the preparation of optically active or racemic prostaglandins.
DE2346706A1 (de)	1975-04-03	Neue, nicht natuerlich vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung
DE2550004C2 (de)	1984-04-26	Thiaprostaglandine sowie Verfahren zu ihrer Herstellung
DE2743283A1 (de)	1979-04-05	Neue prostacyclin-analoga
DE2517773A1 (de)	1976-10-28	Neue 11-oxo-prostaglandin-derivate und verfahren zu ihrer herstellung
CH620893A5 (es)	1980-12-31
DE2618341A1 (de)	1976-11-11	Neue dl-8-aza-9-keto-15-hydroxy- prostan- und -prost-13-trans-ensaeuren, deren 15-methylderivate und pharmazeutisch zulaessige, nicht toxische niederalkylester und salze der carbonsaeurefunktion sowie verfahren zur herstellung solcher verbindungen
CH638480A5 (de)	1983-09-30	Prostaglandinverbindungen.
DE2452536A1 (de)	1976-05-13	Pyrrolidone und verfahren zu ihrer herstellung
DE2307793A1 (de)	1973-08-23	Neue cyclopentanderivate
EP0019069A2 (de)	1980-11-26	6-Keto-PGE1- und PGI1-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2212589C3 (de)	1974-08-29	Verfahren zur Herstellung von 13 beta-R-4,9,11-gonatrienen und 13 beta-R-4,5-seco-9,l 1-gonadiene als Z wise henproduk te
CH615659A5 (en)	1980-02-15	Process for the preparation of novel 11,12-secoprostaglandins
DE2513371C2 (de)	1982-07-15	9,11,15-Trihydroxy-13-thia-5-prostensäure-Derivate und diese enthaltende pharmazeutische Zubereitungen
DE2739770C3 (de)	1982-02-04	19-Methyl-9-keto-15-hydroxy-prost-18-ensäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2507425A1 (de)	1976-09-02	Analoga von prostansaeuren und verfahren zu ihrer herstellung
AT371814B (de)	1983-08-10	Verfahren zur herstellung von neuen lactonderivaten des cyclopentanols
AT272541B (de)	1969-07-10	Verfahren zur Herstellung von Benzindenen