CS276003B6 - method of production of (+)-isomer of cloprostenol - Google Patents

method of production of (+)-isomer of cloprostenol Download PDF

Info

Publication number: CS276003B6
Authority: CS; Czechoslovakia
Prior art keywords: isomer; formula; optically active; cloprostenol; deprotection
Prior art date: 1988-09-28

Application number

CS641088A

Other languages

Czech (cs)

English (en)

Other versions

CS8806410A1 (en

Inventor

Vladimir Ing Votava

Ivan Ing Csc Vesely

Bohumil Ing Zak

Vladimir Ing Csc Dolansky

Jan Rndr Csc Drahonovsky

Jan Ing Csc Stanek

Marie Rndr Ledvinova

Antonin Ing Capek

Jiri Akademik Mostecky

Vladislav Rndr Csc Kubelka

Jaroslav Doc Ing Csc Palecek

Jiri Ing Csc Svoboda

Original Assignee

Spolana

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.)

1988-09-28

Filing date

1988-09-28

Publication date

1992-03-18

1988-09-28 Application filed by Spolana filed Critical Spolana

1988-09-28 Priority to CS641088A priority Critical patent/CS276003B6/cs

1989-09-26 Priority to CA 613186 priority patent/CA1338188C/en

1989-09-27 Priority to JP24937989A priority patent/JPH02152959A/ja

1989-09-28 Priority to DE1989605562 priority patent/DE68905562T2/de

1989-09-28 Priority to EP19890117908 priority patent/EP0362686B1/de

1991-01-15 Publication of CS8806410A1 publication Critical patent/CS8806410A1/cs

1992-03-18 Publication of CS276003B6 publication Critical patent/CS276003B6/cs

Links

VJGGHXVGBSZVMZ-QIZQQNKQSA-N Cloprostenol Chemical compound C([C@H](O)\C=C\[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC(O)=O)OC1=CC=CC(Cl)=C1 VJGGHXVGBSZVMZ-QIZQQNKQSA-N 0.000 title claims abstract description 15
229960004409 cloprostenol Drugs 0.000 title claims abstract description 14
238000000034 method Methods 0.000 title claims abstract description 14
238000004519 manufacturing process Methods 0.000 title description 2
-1 1-methoxybenzyl Chemical group 0.000 claims abstract description 15
238000006243 chemical reaction Methods 0.000 claims abstract description 11
238000010511 deprotection reaction Methods 0.000 claims abstract description 9
150000002596 lactones Chemical class 0.000 claims abstract description 9
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims abstract description 4
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
239000002904 solvent Substances 0.000 claims description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
150000002500 ions Chemical class 0.000 claims description 5
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 claims description 2
238000000354 decomposition reaction Methods 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
229910000342 sodium bisulfate Inorganic materials 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
CPVNCBJFUQQXSU-UHFFFAOYSA-O 4-carboxybutyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 CPVNCBJFUQQXSU-UHFFFAOYSA-O 0.000 abstract 1
238000002955 isolation Methods 0.000 abstract 1
239000000376 reactant Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 12
239000000047 product Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
238000002211 ultraviolet spectrum Methods 0.000 description 4
MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
230000006698 induction Effects 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
241000894007 species Species 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
MWJHXMSQNWUHGK-UHFFFAOYSA-N C=1C=CC=CC=1C(C(O)=O)(P(=O)=O)C(CC)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C(C(O)=O)(P(=O)=O)C(CC)C1=CC=CC=C1 MWJHXMSQNWUHGK-UHFFFAOYSA-N 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
239000002253 acid Substances 0.000 description 2
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000010792 warming Methods 0.000 description 2
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical class 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
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
ZAHGFYXWSJIGEJ-UHFFFAOYSA-N COCCO[Al](OCC)OCCOC.[Na] Chemical compound COCCO[Al](OCC)OCCOC.[Na] ZAHGFYXWSJIGEJ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
101000950847 Homo sapiens Macrophage migration inhibitory factor Proteins 0.000 description 1
102100037791 Macrophage migration inhibitory factor Human genes 0.000 description 1
101100161696 Myxine glutinosa ache gene Proteins 0.000 description 1
241000201940 Oena Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
239000012445 acidic reagent Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
KTGKEJCMFZWYGD-UHFFFAOYSA-N chloroform;1,4-dioxan-2-ylmethanol Chemical compound ClC(Cl)Cl.OCC1COCCO1 KTGKEJCMFZWYGD-UHFFFAOYSA-N 0.000 description 1
MMFVFNVXXDFELX-UHFFFAOYSA-N chloroform;n,n-diethylethanamine Chemical compound ClC(Cl)Cl.CCN(CC)CC MMFVFNVXXDFELX-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
230000003529 luteolytic effect Effects 0.000 description 1
230000001294 luteotrophic effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000010421 standard material Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010626 work up procedure Methods 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS641088A 1988-09-28 1988-09-28 method of production of (+)-isomer of cloprostenol CS276003B6 (en)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CS641088A CS276003B6 (en)	1988-09-28	1988-09-28	method of production of (+)-isomer of cloprostenol
CA 613186 CA1338188C (en)	1988-09-28	1989-09-26	Method of preparing the (+)-isomer of cloprostenol
JP24937989A JPH02152959A (ja)	1988-09-28	1989-09-27	クロルプロステノールの（＋）ー異性体の調整方法
DE1989605562 DE68905562T2 (de)	1988-09-28	1989-09-28	Verfahren zur Herstellung des (+)-Isomers von Cloprostenol.
EP19890117908 EP0362686B1 (de)	1988-09-28	1989-09-28	Verfahren zur Herstellung des (+)-Isomers von Cloprostenol

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS641088A CS276003B6 (en)	1988-09-28	1988-09-28	method of production of (+)-isomer of cloprostenol

Publications (2)

Publication Number	Publication Date
CS8806410A1 CS8806410A1 (en)	1991-01-15
CS276003B6 true CS276003B6 (en)	1992-03-18

Family

ID=5411072

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS641088A CS276003B6 (en)	1988-09-28	1988-09-28	method of production of (+)-isomer of cloprostenol

Country Status (5)

Country	Link
EP (1)	EP0362686B1 (de)
JP (1)	JPH02152959A (de)
CA (1)	CA1338188C (de)
CS (1)	CS276003B6 (de)
DE (1)	DE68905562T2 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1810967B1 (de)	2006-01-18	2014-07-30	Chirogate International Inc.	Verfahren und Zwischenprodukte zur Herstellung von Prostaglandinen
US7642370B2 (en)	2006-08-07	2010-01-05	Daiichi Fine Chemical Co., Ltd.	Method for preparing prostaglandin derivative
CN104513186B (zh) *	2015-01-13	2016-10-05	宁波第二激素厂	一种光学纯的右旋氯前列醇钠的制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE37602B1 (en) *	1971-05-11	1977-08-31	Ici Ltd	Cyclopentane derivatives

1988
- 1988-09-28 CS CS641088A patent/CS276003B6/cs not_active IP Right Cessation
1989
- 1989-09-26 CA CA 613186 patent/CA1338188C/en not_active Expired - Fee Related
- 1989-09-27 JP JP24937989A patent/JPH02152959A/ja active Pending
- 1989-09-28 DE DE1989605562 patent/DE68905562T2/de not_active Expired - Fee Related
- 1989-09-28 EP EP19890117908 patent/EP0362686B1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0362686A2 (de)	1990-04-11
CS8806410A1 (en)	1991-01-15
DE68905562T2 (de)	1993-10-14
EP0362686B1 (de)	1993-03-24
CA1338188C (en)	1996-03-26
JPH02152959A (ja)	1990-06-12
EP0362686A3 (en)	1990-08-29
DE68905562D1 (de)	1993-04-29

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2008-04-23	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20070928

Publication	Publication Date	Title
CA1237718A (en)	1988-06-07	Ester and amide derivatives of 13,14-didehydro- prostaglandins
US4055602A (en)	1977-10-25	2-Decarboxy-2-hydroxy-methyl-5-oxa-17-phenyl-18,19,20-trinor-PGF-analogs
Yuen et al.	1998	On the absolute structure of optically active neolignans containing a dihydrobenzo [b] furan skeleton
NZ209248A (en)	1988-01-08	Purine derivatives, pharmaceutical compositions and intermediates
US4033989A (en)	1977-07-05	9-Deoxy-PGF2 Analogs
SU1561826A3 (ru)	1990-04-30	Способ получени карбоциклических пуриновых нуклеозидов
CH625797A5 (de)	1981-10-15
DE2641823A1 (de)	1977-04-14	Neue prostaglandin-analoga
US4122282A (en)	1978-10-24	2-Decarboxy-2-carboxyamino-methyl-PGFα compounds
CS276003B6 (en)	1992-03-18	method of production of (+)-isomer of cloprostenol
JP2670521B2 (ja)	1997-10-29	プロスタグランジン誘導体の合成方法
FI70009C (fi)	1986-09-12	Foerfarande foer framstaellning av nya 1,5-disubstituerad-2-pyrrolidonfoereningar vilka har prostaglandinliknande biologiska egenskaper
US4320143A (en)	1982-03-16	Fluoro-prostaglandins and process for their preparation
DE2719901A1 (de)	1977-11-24	Pge- und 11-deoxy-pge-verbindungen mit einer methylengruppe am c-9
US4018804A (en)	1977-04-19	Intermediate for synthesis of Thromboxane B2
US4107427A (en)	1978-08-15	Process and intermediates for preparing Thromboxane B1
FR2515642A1 (fr)	1983-05-06	Nouvelles (11r)-11-deoxy-11-alkyl-6-oxo-prostaglandines et compositions pharmaceutiques les contenant
EP0295576B1 (de)	1993-05-19	Verfahren zur Herstellung von 1,3,2-Oxazaphosphorinan
SU1291587A1 (ru)	1987-02-23	Способ получени простагландина @ 2 @ или его аналогов
SU668598A3 (ru)	1979-06-15	Способ получени оптически активных производных простагландинов,или их оптических антиподов,или их рацематов
FI69460C (fi)	1986-02-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara racemiska och optiskt aktiva semiprostanoidglykosider och -tioglykosider
US4292444A (en)	1981-09-29	Sulfonyl prostaglandin carboxamide derivatives
JP2991774B2 (ja)	1999-12-20	プロパルギルアルコールの新規合成法および該アルコールのプロスタグランジン前駆物質を製造するための使用
EP0022443B1 (de)	1984-09-26	N-Alkansulfonyl-Carboxamide von 16,16-Dimethyl-17-oxaprostaglandin
DE2641091A1 (de)	1977-07-28	Prostaglandin-analoga und verfahren zu deren herstellung