CS204595B1 - Process for preparirng analogs of prostaglandin f2alpha - Google Patents

Process for preparirng analogs of prostaglandin f2alpha Download PDF

Info

Publication number: CS204595B1
Authority: CS; Czechoslovakia
Prior art keywords: carbon atoms; group; formula; hydrogen; hydroxyl
Prior art date: 1979-03-16

Application number

CS177879A

Other languages

Czech (cs)

English (en)

Inventor

Karel Capek

Vladislav Kubelka

Jaroslav Palecek

Jan Stanek

Ivan Stibor

Ivan Vesely

Vaclav Dudek

Zdenek Havel

Miroslav Janda

Vaclav Dedek

Jiri Jary

Jiri Mostecky

Original Assignee

Karel Capek

Vladislav Kubelka

Jaroslav Palecek

Jan Stanek

Ivan Stibor

Ivan Vesely

Vaclav Dudek

Zdenek Havel

Miroslav Janda

Vaclav Dedek

Jiri Jary

Jiri Mostecky

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.)

1979-03-16

Filing date

1979-03-16

Publication date

1981-04-30

1979-03-16 Application filed by Karel Capek, Vladislav Kubelka, Jaroslav Palecek, Jan Stanek, Ivan Stibor, Ivan Vesely, Vaclav Dudek, Zdenek Havel, Miroslav Janda, Vaclav Dedek, Jiri Jary, Jiri Mostecky filed Critical Karel Capek

1979-03-16 Priority to CS177879A priority Critical patent/CS204595B1/cs

1979-07-12 Priority to HUVI001260 priority patent/HU186728B/hu

1979-08-07 Priority to SU797770731A priority patent/SU1104134A1/ru

1979-08-21 Priority to DD21521079A priority patent/DD156120A3/de

1981-04-30 Publication of CS204595B1 publication Critical patent/CS204595B1/cs

Links

238000000034 method Methods 0.000 title claims description 19
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 title description 2
PXGPLTODNUVGFL-UHFFFAOYSA-N prostaglandin F2alpha Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CC=CCCCC(O)=O PXGPLTODNUVGFL-UHFFFAOYSA-N 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims description 37
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
-1 nitro- Chemical class 0.000 claims description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
150000002596 lactones Chemical group 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
150000003180 prostaglandins Chemical class 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
150000004678 hydrides Chemical class 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 3
150000002170 ethers Chemical class 0.000 claims description 3
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 3
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims description 2
150000001241 acetals Chemical class 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 claims description 2
OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 claims description 2
125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
150000001242 acetic acid derivatives Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
238000002425 crystallisation Methods 0.000 claims 1
230000008025 crystallization Effects 0.000 claims 1
KBLZFQBDODEHJH-UHFFFAOYSA-N dibutylalumane Chemical compound C(CCC)[AlH]CCCC KBLZFQBDODEHJH-UHFFFAOYSA-N 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
150000002924 oxiranes Chemical class 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
125000003396 thiol group Chemical group [H]S* 0.000 claims 1
239000000243 solution Substances 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
239000000047 product Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
238000001228 spectrum Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000001035 drying Methods 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
150000002009 diols Chemical class 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
150000004714 phosphonium salts Chemical class 0.000 description 5
235000002639 sodium chloride Nutrition 0.000 description 5
239000007787 solid Substances 0.000 description 5
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
POKRQUNDSGAZIA-OALUTQOASA-N 7-[(1r,2s)-2-octylcyclopentyl]hepta-2,4-dienoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCC=CC=CC(O)=O POKRQUNDSGAZIA-OALUTQOASA-N 0.000 description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000005642 Oleic acid Substances 0.000 description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-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
238000007171 acid catalysis Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
ZGKIYLYSHXFWES-UHFFFAOYSA-N pentanoic acid;hydrobromide Chemical compound Br.CCCCC(O)=O ZGKIYLYSHXFWES-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-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
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
150000003527 tetrahydropyrans Chemical class 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
MXQNHNJSQKBNDC-UHFFFAOYSA-N 2-methoxy-2h-pyran Chemical compound COC1OC=CC=C1 MXQNHNJSQKBNDC-UHFFFAOYSA-N 0.000 description 1
YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
QFHZPMOJWIBZCS-UHFFFAOYSA-N 3-propan-2-ylpyrrolidine Chemical compound CC(C)C1CCNC1 QFHZPMOJWIBZCS-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
101100042788 Caenorhabditis elegans him-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
239000008896 Opium Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
UQDAEORWFCPQCU-UHFFFAOYSA-N acetic acid;oxolane;hydrate Chemical compound O.CC(O)=O.C1CCOC1 UQDAEORWFCPQCU-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001602 bicycloalkyls Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000002592 echocardiography Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
HZZOEADXZLYIHG-UHFFFAOYSA-N magnesiomagnesium Chemical compound [Mg][Mg] HZZOEADXZLYIHG-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
IKXILDNPCZPPRV-RFMGOVQKSA-N metholone Chemical compound C1C[C@@H]2[C@@]3(C)C[C@@H](C)C(=O)C[C@@H]3CC[C@H]2[C@@H]2CC[C@H](O)[C@]21C IKXILDNPCZPPRV-RFMGOVQKSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
UPQNPBHYPACBSK-UHFFFAOYSA-N methylsulfinylmethane;sodium Chemical compound [Na].CS(C)=O UPQNPBHYPACBSK-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
229960001027 opium Drugs 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000001766 physiological effect Effects 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
238000000746 purification Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

CS177879A 1979-03-16 1979-03-16 Process for preparirng analogs of prostaglandin f2alpha CS204595B1 (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CS177879A CS204595B1 (en)	1979-03-16	1979-03-16	Process for preparirng analogs of prostaglandin f2alpha
HUVI001260 HU186728B (en)	1979-03-16	1979-07-12	Process for preparing prostaglandim f down 2 d analogues
SU797770731A SU1104134A1 (ru)	1979-03-16	1979-08-07	Способ получени аналогов простагландинов @
DD21521079A DD156120A3 (de)	1979-03-16	1979-08-21	Verfahren zur gewinnung von prostaglandin-analoga f tief 2 alpha

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS177879A CS204595B1 (en)	1979-03-16	1979-03-16	Process for preparirng analogs of prostaglandin f2alpha

Publications (1)

Publication Number	Publication Date
CS204595B1 true CS204595B1 (en)	1981-04-30

Family

ID=5353047

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS177879A CS204595B1 (en)	1979-03-16	1979-03-16	Process for preparirng analogs of prostaglandin f2alpha

Country Status (4)

Country	Link
CS (1)	CS204595B1 (de)
DD (1)	DD156120A3 (de)
HU (1)	HU186728B (de)
SU (1)	SU1104134A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011055377A1 (en) *	2009-11-05	2011-05-12	Biocon Limited	A novel process for the preparation of prostaglandins and intermediates thereof
CZ305221B6 (cs) *	2013-12-10	2015-06-17	Univerzita Pardubice	Způsob přípravy (3aR,4S,5R,6aS)-4-[(3S)-5-cyklohexyl-3-hydroxypent-1-yn-1-yl]-5-(ethoxymethoxy)-hexahydro-2H-cyklopenta[b]furan-2-onu

1979
- 1979-03-16 CS CS177879A patent/CS204595B1/cs unknown
- 1979-07-12 HU HUVI001260 patent/HU186728B/hu unknown
- 1979-08-07 SU SU797770731A patent/SU1104134A1/ru active
- 1979-08-21 DD DD21521079A patent/DD156120A3/de not_active IP Right Cessation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011055377A1 (en) *	2009-11-05	2011-05-12	Biocon Limited	A novel process for the preparation of prostaglandins and intermediates thereof
US20120209011A1 (en) *	2009-11-05	2012-08-16	Chandrashekar Aswathanarayanappa	novel process for the preparation of prostaglandins and intermediates thereof
CZ305221B6 (cs) *	2013-12-10	2015-06-17	Univerzita Pardubice	Způsob přípravy (3aR,4S,5R,6aS)-4-[(3S)-5-cyklohexyl-3-hydroxypent-1-yn-1-yl]-5-(ethoxymethoxy)-hexahydro-2H-cyklopenta[b]furan-2-onu

Also Published As

Publication number	Publication date
HU186728B (en)	1985-09-30
DD156120A3 (de)	1982-08-04
SU1104134A1 (ru)	1984-07-23

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