IE912654A1

IE912654A1 - Cyclopentane derivatives, process for their production and their pharmaceutical use

Info

Publication number: IE912654A1
Application number: IE265491A
Authority: IE
Inventors: Dr Ulrich Klar; Dr Hartmut Rehwinkel; Dr Karl-Heinz Thierauch; Dr Peter Verhallen; Prof Helmut Vorbruggen
Original assignee: Schering Ag
Priority date: 1990-07-27
Filing date: 1991-07-29
Publication date: 1992-01-29
Also published as: DE4024347A1; IL98970A0; PT98464B; DE4191848D2; ZA915905B; ES2074721T3; DE59105400D1; ATE122036T1; EP0541594A1; CA2088161A1; JPH06502390A; AU8221291A; PT98464A; WO1992002495A1; DK0541594T3; EP0541594B1; IE67507B1

Abstract

The invention relates to cyclopentane derivatives of formula (I) and their salts with physiologically tolerables bases and the $g(a), $g(b) or $g(g)-cyclodextrin clathrates and the liposome-encapsulated compounds of formula (I), a process for producing them and their pharmaceutical use.

Description

Cyclopentane Derivatives, Process for their Production and their Pharmaceutical Use Description: The invention relates to cyclopentane derivatives, process for their production as well as their use as auxiliary agents for pharmacological studies and as pharmaceutical agents.

Cyclopentane derivatives have been dealt with intensively in recent years, since prostaglandins derived from the cyclopentane system, such as, e.g., PGA2, PGB2, PGE2, 6-oxo-PGE|, PGD2, PGF2aipha/ PGJ2and their analogs, have the most varied biological actions, e.g., on the cardiovascular system, the central nervous system or immune system.

It has been found, surprisingly, that by the introduction of a fluorine atom or a hydroxy group in 9-position (prostaglandin numbering system) of the prostaglandin skeleton in combination with the most varied structural features in the lower chain as well as in 11-position, chemically and metabolically stable prostaglandin analogs are obtained which are able to antagonize the pharmacological properties of unstable thromboxane A2 (TXA2) or PGH2 as well as its stable analogs, such as, e.g., U46619 or U44069 on the receptor.

The compounds of this invention therefore constitute valuable auxiliary agents for selective treatment of diseases, which are attributable to an excess of TXA2 or PGH2.

The invention relates to cyclopentane derivatives of formula I, in which R1 can be 0-y / o-\ N’ N 1« .N* COOR , and R5 can mean hydrogen or Cj-Cjq alkyl, Cj-Cjq cycloalkyl, C7-CJ6 aralkyl, optionally substituted by halogen, phenyl, C1-C4 alkoxy or di-(Ci-C4)-alkylamino, phenacyl or Cg-C^ aryl substituted by Y or a 5- or 6-membered heterocyclic radical with at least one N, 0 7 7 or S atom, or -CONHR with R meaning hydrogen, Cj-Cjo alkyl, CgCj2 arylsulfonyl, Cj-Cjo alkanoyl or Cj-Cjq alkanesulfonyl, X means -(CH2)p-, -CH2-O- or -CH2-S-, Z,A, independent of one another, mean a direct bond, (Z)-CH=CH-, (E)-CH=CH- or -C=C-, p means 0 to 5, R means fluorine, OH, n,r, independent of one another, mean 0 to 2, R3 means OR6 or R6, W means a direct bond, a -((CH2) n-V]q group, a -(CH2)n-V(CH2)q-V group, a free or functionally modified hydroxyraethylene group or a free or functionally modified the group, and hydroxy group can be respectively in alpha- or beta-position, q means 1 or 2, D means a direct bond, a straight-chain saturated alkylene group with 1-5 C atoms, a branched saturated alkylene group or a straight-chain or branched unsaturated alkylene group with 2-5 C atoms, which can be optionally substituted by fluorine atoms, -(CH2)n-NH-SO2-, Ar0· -(CH2)n.

.(CH2) X ,so2n N N • · Η H •(CH2) X η N N‘ Η H Η H rN. riN >· » -.. z NJ SO, / \ -(CH^-NH-NH-SOj-, CHY V means an 0 or S atom, g E means a direct bond, -C=C- or -CH=CR -, and R means hydrogen, Cj-Cs alkyl, halogen or trifluoromethyl, AWDE together mean a direct bond, AW together mean a direct bond, DE together can be a direct bond, C3-C10 cycloalkyi or Cj-Cjq alkyl optionally substituted by Y, m means 1 or 2, Yj and Y2 are the same or different and mean Y, Y means hydrogen, halogen, N3, CF3, OR^, N02, NH2, CN, COOR& or Cj-Cjq alkyl, R6 can be hydrogen, Cj-Cjq alkyl, Cg-Cj2 aryl or C7-C,g aralkyl optionally substituted by halogen and, if R5 means hydrogen, their salts with physiologically compatible bases, as well as the alpha-, beta- or gamma-cyclodextrin clathrates, as well as the compounds of formula I encapsulated with liposomes.

The definition of 5- or 6-membered heterocyclic radical relates to heterocycles, which contain at least one heteroatom, preferably nitrogen, oxygen or sulfur, and are monocyclic or bicyclic. For example, there can be mentioned 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, quinolyl, isoquinolyl. 6 As alkyl groups R , R , R , E and Y, straight-chain or branched-chain alkyl groups with 1-10 C atoms, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, pentyl, isopentyl, neopentyl, heptyl, hexyl, decyl, are suitable.

Alkyl groups R4, r\ r\ e and Y can be substituted by halogen atoms, hydroxy groups, C1-C4 alkoxy groups, C^-C^ aryl groups, which can be substituted by halogen, di-fCj-C^)alkylamines and tri-(Cj-C4)-alkylammonium. Those alkyl groups which are singly substituted are preferred.

As substituents, for example, there can be mentioned fluorine, chlorine or bromine atoms, phenyl, dimethylamino, diethylamino, methoxy, ethoxy.

As preferred alkyl groups R4, R$, R^, E and Y, those with 1-5 C atoms, such as, e.g., methyl, ethyl, propyl, isobutyl, butyl, neopentyl, tert-butyl, chloroethyl, 1- and 2-chloropropyl, hydroxyethyl and 1- and 2-hydroxypropyl can be mentioned.

As aryl groups and r\ for example, phenyl, diphenyl, 1naphthyl and 2-naphthyl, which can be substituted by 1-3 halogen atoms, a phenyl group, 1-3 alkyl groups each with 1-4 C atoms, a chloromethyl group, fluoromethyl group, carboxyl group, C1-C4 alkoxy or hydroxy group, are suitable. The substitution in 3and 4-position on the phenyl ring is preferred, for example, by fluorine, chlorine, C1-C4 alkoxy or trifluoromethyl or in 4position by hydroxy.

Cycloalkyl groups R$ can contain 3-10, preferably 3-6 carbon atoms, in the ring. The rings can be substituted by alkyl groups with 1-4 carbon atoms. For example, there can be mentioned cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl.

The Cj-C|q alkyl groups mentioned under the definitions should be straight-chain or branched alkyl groups, as they were already mentioned for the alkyl groups above. . 2 3 The hydroxy groups in R , R , Y and W can be functionally modified, for example, by etherification or esterification, and 2 the free or modified hydroxy group rn R and W can be m alphaor beta-position, and free hydroxy groups are preferred.

As ether and acyl radicals, the radicals known to one skilled in the art are suitable. Easily cleavable ether radicals, such as, for example, the tetrahydropyranyl, tetrahydrofuranyl, tert-butyldimethylsilyl, tertbutyldiphenylsilyl, tribenzylsilyl radical, are preferred.

As acyl radicals, e.g., acetyl, propionyl, butyryl, benzoyl, are suitable.

Halogen in the definitions for R^, R^, E and Y means fluorine, chlorine, bromine and iodine.

Radicals Cj-Cjq alkanoyl or Cj-Ciq alkanesulfonyl for R7 correspond to the already mentioned alkyl groups of the same length with the difference that they are bound on a carboxyl Ί group or sulfonyl group. CJ-C4 alkanoyl or C1-C4 alkanesulfonyl are preferred.

Inorganic and organic bases are suitable for salt formation with the free acids (R5 = H), as they are known to one skilled in the art for forming physiologically compatible salts. For example, there can be mentioned: alkali hydroxides, such as sodium hydroxide or potassium hydroxide, alkaline-earth hydroxides, such as calcium hydroxide, ammonia, amines, such as ethanolamine, diethanolamine, triethanolamine, n-methylglucamine, morpholine, tris-(hydroxymethyl)methylamine, etc.

The compounds of formula I in which R1 means the group COOR5 or CONHR7, R3 means hydrogen, hydroxyl, C1-C4 alkyl, C5-C12 aryl or C7C|6 aralkyl optionally substituted by halogen, R5 means hydrogen or C7-Cj6 aralkyl, C5-C6 cycloalkyl or CjCjQ alkyl optionally substituted by halogen, R7 means C[-C7 alkanoyl, Cg-Cj2 arylsulfonyl or Cj-C7 alkanesulfonyl, p means 0 to 4, n,r, independent of one another, mean 0 or 1, are preferred.

The compounds of formula I, in which R1 means the group COOR5, R3 means hydrogen, hydroxyl, phenyl or phenylethyl, R5 means hydrogen or methyl, R means methanesulfonyl, a p means 0 to 4, n,r, independent of one another, mean 0 or 1, are especially preferred.

The compounds of formula I according to the application can be produced as described in more detail below: A. with R1, R2, R3, R4, X, Z in the above-indicated meanings, Hal as bromine or chlorine, A,DE as a direct bond, rI meaning a -COOR3 ester. Β. with R2, R3, R4, A, Ε, X, Z in the above-indicated meanings, D as alkylene optionally substituted by alkyl, or r1 meaning a -COOR^ ester, q R as hydrogen or bromine, W as -CH(OH)-.

Hal-SO2-R4 (IX) with R2, R3, R4, X, Z, Hal in the above-indicated meanings, AW,E as a direct bond, O -(¾) II D meaning 0 *N Ν' > -(CH^-NH-SO^, Η H R1 meaning a -COOR5 ester.

D.

H2N-O—R4 (X) or H2N-NH-SO2-R4 (XIII) IV or H,N.

‘N I H N‘ I H (XI) h) with R2, R3, R4, X, Z in the above-indicated meanings, AW,E as a direct bond, R1 meaning a -COOR5 ester, D meaning — SO, -(CH2)n-NH-NH-SO2 Ε.

Hal-SO2-R4 (IX) AW,E as a direct bond, -(°¾) 1 D meaning 1 . {CHJj-NH-SO,-, H .H R1 meaning a -COOR5 ester.

The compounds of formula I can be produced according to claim 3 corresponding to the above-described process alternatives. The initial compounds of formula II are produced corresponding to the instructions indicated in examples lg-ln, 24a-24g and 34a-34b.

The reaction conditions of the following process stages are: a) II=^>I (Process A) In the presence of aqueous alkali or alkaline-earth solutions, and with use of phase transfer catalysts (such as, e.g., tetrabutylammonium hydrogen phosphate or sulfate), compounds of formula II are reacted at 20 to 100°C within 1 to 16 hours with reactands III as the organic phase or a solution of III in an inert, water-immiscible, organic solvent, a fluorine . . 2 atom, as described in example 1, is optionally introduced for R , or a hydroxyl group, as described in examples 74 and 74a, is removed. b) II => IV (Process B) The oxidation of the compounds of formula II takes place according to known processes, such as, e.g., according to that of Swern, Collins as well as with use of pyridinium dichromate or chlorochromate in solvents such as dichloromethane, diethyl ether, tetrahydrofuran, benzene or toluene at -80°C to -50°C (Swern) or to +30°C (in the usual oxidations) within 10 minutes to 8 hours. c) IV VI (Process B) , d) VI ==> I (Process B) The reaction of compounds IV with phosphonates V as well as the subsequent reduction or HBr elimination took place analogously to the conditions mentioned in DE-OS 2845770. e) II# VII (Process C) The oxidation of the compounds of formula II is performed preferably with Jones reagent or pyridinium chlorochromate according to the reaction conditions known to one skilled in the art. Then, it is converted under usual conditions with thionyl chloride to acid chloride, brought to reaction under phase transfer catalysis with aqueous sodium azide solution, and rearranged in compounds of formula VIII as described in example lc, optionally, a C-C multiple bond is hydrogenated in Z or a fluorine atom is introduced, as described in example 1. f) VII rf VIII (Process C) The conversion of the compounds of formula VII to compounds of formula VIII takes place as described in example lc. g) VIII (Process C) The reaction of the compounds of formula VIII with the compounds of formula IX or XII takes place as in examples lb and 78 mentioned in this respect. h) IV =^> I (Process D) The reaction takes place analogously to the process described in WO 90/02740 (Process C, p. 16). i) II XIV (Process E) The conversion of the compounds of formula II to the compounds of formula XIV takes place as described in examples 78a to 78c. k) XIV =rfl (Process E) The reaction of the compounds of formula XIV with the compounds of formula IX or XII takes place as described in examples lb and 78. . . . 2 3 The release of functionally modified hydroxy groups R , R , R4 and W takes place according to the methods known to one skilled in the art. For example, the cleavage of ether protecting groups is performed in an aqueous solution of an organic acid, such as, e.g., acetic acid, propionic acid, citric acid, i.a, or in an aqueous solution of an inorganic acid, such as, e.g., hydrochloric acid, or in the case of tetrahydropyranyl ethers with use of pyridinium-p-toluenesulfonate, preferably in alcohols as solvent or with use of anhydrous magnesium bromide, preferably in diethyl ether as solvent.

To improve the solubility, a water-miscible inert solvent is suitably added with use of aqueous-acid reaction conditions. Proven as suitable, there are, e.g., alcohols, such as methanol and ethanol, ethers, such as dimethoxyethane, dioxane and tetrahydrofuran, and tetrahydrofuran is preferably used.

The cleavage of silylether protecting groups takes place, for example, with tetrabutylammonium fluoride according to the methods known to one skilled in the art. As solvent, for example, tetrahydrofuran, diethyl ether, dioxane, methylene chloride, etc., are suitable. The cleavage is performed preferably at temperatures between 20°C and 80°C.

The saponification of the acyl groups and ester in COOR^ of the cyclopentane derivatives is performed according to the methods known to one skilled in the art, such as, for example, with basic catalysts, such as, e.g., with alkali or alkalineearth carbonates or hydroxides in an alcohol or the aqueous solution of an alcohol. As alcohols, aliphatic alcohols, such as, e.g., methanol, ethanol, butanol, etc. are suitable, but preferably methanol. As alkali carbonates and hydroxides, there can be mentioned lithium, sodium and potassium salts. The lithium and potassium salts are preferred. As alkaline-earth carbonates and hydroxides, for example, calcium carbonate, calcium hydroxide and barium carbonate are suitable. The reaction generally takes place at -10°C to +70°C, but preferably at +25°C.

The introduction of ester group CO2r5 for R1 or CO2r6 for Y, in which R5 or R^ represents an alkyl group with 1-10 C atoms, takes place according to the methods known to one skilled in the art. The carboxy compounds (R5 = H or R6 = H) are reacted, for example, with diazohydrocarbons in a way known in the art. The esterification with diazohydrocarbons takes place, e.g., in that a solution of the diazohydrocarbon in an inert solvent, preferably in diethyl ether, is mixed with the carboxy compound, dissolved in the same or in another likewise inert solvent, such as, e.g., methylene chloride. After completion of the reaction within 1 to 60 minutes, the solvent is removed and the ester is purified in the usual way. Diazoalkanes are either known or can be produced according to known methods [Org. Reactions, Vol. 8, pages 389-394 (1954)].

The introduction of ester group CO2R5 for R1 or CO2R^ for Y, in which R5 or R^ represents a substituted or unsubstituted aryl group, takes place according to the methods known to one skilled in the art. For example, the 1-carboxy compounds are reacted with the corresponding arylhydroxy compounds with dicyclohexylcarbodiimide in the presence of a suitable base, such as, e.g., pyridine, DMAP, triethylamine, in an inert solvent, such as, e.g., methylene chloride, ethylene chloride, chloroform, ethyl acetate, tetrahydrofuran, but preferably with chloroform.

The reaction is performed at temperatures between -30°C and +50°C, preferably at +10°C.

The cyclopentane derivatives of formula I with R5 or meaning a hydrogen atom can be converted to salts with suitable amounts of the corresponding inorganic bases with neutralization. For example, by dissolving the corresponding acids in water, which contains stoichiometric amounts of the base, the solid inorganic salt is obtained after evaporation of the water or after addition of a water-miscible solvent, e.g., alcohol or acetone.

The production of the amine salts takes place in the usual way. For this purpose, the acid is dissolved in a suitable solvent, such as, e.g., ethanol, acetone, diethyl ether or benzene and 1 to 5 equivalents of the respective amine is added to this solution. In this case, the salt usually accumulates in solid form or is isolated in the usual way after evaporation of the solvent.

The functional modification of the free hydroxy groups takes place according to the methods known to one skilled in the art. For the introduction of the ether protecting groups, it is reacted, for example, with dihydropyran or methyl vinyl ether in methylene chloride or chloroform with use of catalytic amounts of an acid condensing agent, such as, e.g., p-toluenesulfonic acid. The respective enol ether is added in excess, preferably in 1.2 to 10 times the amount of the theoretical requirement. The reaction normally takes place at -10°C to +30°C and is conpleted after 2 to 45 minutes.

For the introduction of silylether protecting groups, it is reacted, for example, with t-butyl-diphenylchlorosilane or tbutyl-dimethylchlorosilane in dimethylformamide with use of a base, such as, e.g., imidazole. The respective silyl chloride is added in excess, preferably in 1.05 to 4 times the amount of the theoretical requirement. The reaction normally takes place at 0°C to 30°C and is completed after 1 to 24 hours.

The introduction of the acyl protecting groups takes place by a compound of formula I being reacted in a way known in the art with a carboxylic acid derivative, such as, e.g., acid chloride, acid anhydride, etc.

Cyclodextrin clathrates are obtained analogously to the instructions in WO 87/05294.

Liposomes are produced according to the production process described in Pharmazie in unserer Zeit [Pharmaceutics in Our Time] 11, 98 (1982).

All stereoisomeric forms also relate to the object of the invention.

IS Biological Action and Area of Use of the New TXA2 Antagonists: The compounds of this invention are suitable for treatment of diseases of the cardiovascular system, the stomach, the pancreas, the liver and the kidneys. They work in an antihypertensive and bronchodilatory manner. They are excellently suited for inhibition of the activation of platelets. Consequently, the new TXA2 antagonists of formula I represent valuable pharmaceutical active ingredients. Moreover, the compounds are distinguished by higher selectivity, a substantially longer effectiveness and a greater stability as compared to similar TXA2 antagonists.

The new TXA2 antagonists have the properties typical for this family of compounds, such as, e.g., reduction of the peripheral arterial, the coronary and pulmonary vascular resistance, reduction of the pulmonary blood pressure, reduction of the systemic blood pressure without reducing the cardiac output and coronary blood circulation at the same time, promotion of the kidney blood circulation and the blood circulation of other peripheral organs, increase of the cerebral blood circulation, inhibition of the platelet activation and dissolution of blood clots, inhibition of bronchoconstriction, inhibition of gastric acid secretion, cytoprotection of the heart, the stomach and intestinal mucous membrane, the liver, cytoprotection in the pancreas and in the kidneys as well as antiallergic properties. Therefore, the new TXA2 antagonists are suitable on principle for treatment of stroke, prophylaxis and treatment of coronary heart diseases, for example, coronary thrombosis, for treatment of myocardial infarction, peripheral arteriopathies, for prophylaxis and treatment of other thromboembolic diseases and in arteriosclerosis, in ischemic attacks of the central nervous system and other disturbances of the blood circulation of the brain, such as, e.g., migraine, for treatment of hypertonia and for treatment of diseases which accompany an increase of the pulmonary vascular resistance, such as, e.g., the pulmonary hypertonia and for treatment of shock, asthma and allergic rhinitis. They can further be used to inhibit labor pains and for treatment of toxicoses in pregnancies.

Further, the new TXA2 antagonists can be used to improve the organ function after transplantation, for example, in kidney transplantation, to prevent rejection reactions, instead of heparin or as adjuvant in the case of dialysis or hemofiltration and in the case of storing dried blood plasma, for example, dried blood platelets.

The new TXA2 antagonists have an antimetastatic action and antiproliferative properties. They are suitable on principle for treatment of neoplasias.

The new TXA2 antagonists can be used in combination with, for example, carbacyclins, prostacyclin and its analogs, 7oxoprostacyclins, prostaglandins and their derivatives and 6-oxoPGEj- and 6-oxo-9-fluoroprostaglandin derivatives, with TXA2synthetase inhibitors, with phosphodiesterase inhibitors, with ? ! antagonists and receptor antagonists of various platelet stimulators (e.g., ADP, thrombin, collagen, PAF, adrenaline, serotonin, fibrinogen), with calcium antagonists, with fibrinolytic agents and thrombolytic agents, e.g., t-PA, streptokinase, with heparin and other anticoagulants, with cyclooxygenase inhibitors, e.g., acetylsalicylic acid, with inhibitors of lipoxygenases as well as antagonists of lipoxygenase products, with vasodilators, such as, e.g., nitro compounds, with antihypertensive agents, such as, e.g., betablockers or with diuretics.

The dose of the compounds is 0.1-1000 mg/day, preferably 0.1-500 mg/day, also in several partial doses, if they are administered to human patients. The unit dose for the pharmaceutically acceptable vehicle is 0.1-100 mg. For parenteral administration, sterile, injectable aqueous or oily solutions are used. For oral administration, for example, tablets, coated tablets, or capsules are suitable.

Thus, the invention also relates to pharmaceutical agents based on the compounds of general formula I and usual auxiliary agents and vehicles.

The active ingredients according to the invention are to be used in connection with the auxiliary agents known and usual in galenicals, e.g., for the production of antihypertensive agents.

The unit dose range for the ampoule is 0.1-100 mg, for the tablet 0.1-100 mg.

Example 1: 7-[(IR,2S,5R)-2-(4-Toluenesulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (139 micromol) of the alcohol produced according to example la is dissolved in 2.5 ml of anhydrous toluene, mixed with 56 microliters of anhydrous pyridine, cooled under an atmosphere of dry argon to -60°C and mixed with 42 microliters of diethylaminosulfur trifluoride. It is allowed to heat over 3.5 hours to 0°C, quenched by adding 1 ml of a saturated sodium bicarbonate solution, diluted with water and extracted several times with dichloromethane. The combined organic extracts are dried on magnesium sulfate and the residue obtained after removal of the solvent is purified by chromatography on 4 analytic thinlayer slabs. A mixture of n-hexane and acetone is used as mobile solvent, diethyl ether is used as eluant. 20 mg (53 micromol, 38%) of 7-[5(S)-(4-toluenesulfonylamino)-cyclopent-l-enyl]-5(Z)heptenoic acid methyl ester as well as 16 mg (40 micromol, 29%) of the title compound are each isolated as colorless oil.

IR (KBr): 3430, 3310, 3050, 3020, 2940, 2860, 1735, 1600, 1450, 1320, 1240, 1160, 1095, 920, 815, 670, 580 and 550 cm1.

Example la: 7-[(IR,2S,5S)-2-(4-Toluenesulfonylamino) -5-hydroxycyclopentyl]-5(Z)-heptenoic acid methyl ester: The solution of 140 mg (280 micromol) of the compound, produced according to example lb, in 1.5 ml of methanol is mixed 3 with 20 mg of finely pulverized potassium carbonate and heated for 1 hour to 70°C. After the cooling, it is acidified with saturated citric acid, diluted with water and extracted several times with dichloromethane. The combined organic extracts are dried on magnesium sulfate and the residue obtained after removal of the solvent is purified by chromatography on 2 analytic thinlayer slabs. A mixture of n-hexane and ethyl acetate is used as mobile solvent, diethyl ether is used as eluant. 96 mg (243 micromol, 87%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3270, 2940, 2870, 1735, 1600, 1450, 1330, 1270, 1160, 1110, 1090, 1025, 815 and 665 cm'1.

Example lb: 7-[(IR,2S,5S)-2-(4-Toluenesulfonylamino)-5-benzoyloxycyclopentyl]-5(Z)-heptenoic acid methyl ester: The solution of 340 mg (984 micromol) of the amine, produced according to example lc, in 30 ml of anhydrous dichloromethane is mixed with 1.52 ml of triethylamine, 483 mg of p-toluenesulfonic acid chloride and stirred for 1.5 hours at 23°C under an atmosphere of dry argon. It is poured on a semiconcentrated sodium chloride solution and extracted several times with dichloromethane. The combined organic extracts are dried on magnesium sulfate and the residue obtained after removal of the solvent is purified by chromatography on about 70 ml of fine silica gel with a gradient system of n-hexane and ethyl acetate. 330 mg (660 microraol, 67%) of the title compound is isolated as colorless oil.

IR (Film): 3270, 2940, 2870, 1730, 1710, 1600, 1450, 1330, 1270, 1160, 1110, 1090, 1025, 905, 815, 710 and 665 cm1.

Example lc: 7-[ (IR, 2S,5S)-2-Amino-5-benzoyloxy-cyclopentyl]-5(Z)heptenoic acid methyl ester (A) and 7-[(1R,2S,5S)-2trifluoroacetamido-5-benzoyloxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester (B): The solution obtained according to example Id is mixed with 1.47 ml of trifluoroacetic acid and refluxed for 6 hours. It is allowed to stand for 14 hours at 23°C, is concentrated by evaporation and the residue is purified by chromatography on about 250 ml of fine silica gel with a gradient system of dichloromethane and methanol. 2.0 g (5.79 mmol, 43% relative to the feedstock in example le) of title compound A as well as 1.53 g (3.47 mmol, 26% relative to the feedstock in example le) of title compound B are isolated.

IR (CHC13) of A: 3500-2600, 2950, 2870, 1710, 1670, 1450, 1275, 1190, 1140 and 835 cm1.

IR (Film) of B: 3320, 2950, 2870, 1740-1690, 1600, 1550, 1450, 1435, 1270, 1210, 1180, 1110, 1070, 1025 and 710 cm1.

Example Id: 7-((IR,2S,5S)-2-Azidocarbonyl-5-benzoyloxy-cyclopentyl]5(Z)-heptenoic acid methyl ester: The residue obtained according to example le is dissolved in 20 ml of dichloromethane, cooled to 3°C, mixed with 10 mg of tetrabutylammonium hydrogen sulfate and the solution of 1.04 g of sodium azide in 3.5 ml of water. It is stirred for 2.5 hours, diluted with dichloromethane, the organic phase is separated and dried on freshly roasted magnesium sulfate. The solution obtained after filtration is immediately further reacted.

Example le: 7-((IR,2S,5S)-2-Chlorocarbonyl-5-benzoyloxy-cyclopentyl]5(Z)-heptenoic acid methyl ester: The solution of 5.0 g (13.4 mmol) of the compound, produced according to example If, in 133 ml of anhydrous dichloromethane is mixed under ice cooling with 2.13 ml of freshly distilled thionyl chloride and allowed to stir for 20 hours at 23°C under an atmosphere of dry argon. It is concentrated by evaporation and the resulting residue is further reacted without purification.

Example If: 7-((IR,2S,5S)-2-Hydroxycarbonyl-5-benzoyloxy-cyclopentyl]5(Z)-heptenoic acid methyl ester: The solution of 30.2 g (83.9 mmol) of the alcohol, produced according to example lg, in 725 ml of acetone is cooled to -15°C, mixed with 44 ml of a standardized chromosulfuric acid solution (Jones reagent), stirred for 3 hours at -10°C and excess oxidizing agent is decomposed by adding 13 ml of isopropanol. It is diluted with water, extracted several times with diethyl ether, the combined organic extracts are washed with water and saturated sodium chloride solution and dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on about 1 1 of coarse silica gel with a gradient system of n-hexane and ethyl acetate. 29.3 g (78.3 mmol, 93%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2500, 3060, 2950, 2860, 1740-1690, 1600, 1580, 1450, 1435, 1360, 1310, 1270, 1170, 1110, 1070, 1025 and 710 cm1.

Example lg: 7-((IR,2S,5S)-2-Hydroxymethyl-5-benzoyloxy-cyclopentyl]5(Z)-heptenoic acid methyl ester: The solution of 57.9 g (96.7 mmol) of the compound, produced according to example lh, in 124 ml of anhydrous tetrahydrofuran is mixed with 155 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran and stirred for 17 hours at 23°C under an atmosphere of dry argon. It is mixed with water, extracted several times with diethyl ether, the combined organic extracts are washed with water and saturated sodium chloride solution and it is dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on about 2 1 of coarse silica gel with a gradient system of n-hexane and ethyl acetate. 30.2 g (83.8 mmol, 87%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3060, 2940, 2860, 1735, 1710, 1600, 1580, 1360, 1310, 1275, 1170, 1110, 1070, 1025 and 715 cm1.

Example lh: 7-[(IR,2S,5S)-2-(tert-Butyldiphenylsilyloxymethyl)-5benzoyloxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: The solution of 47.9 g (96.7 mmol) of the compound, produced according to example li, in 212 ml of anhydrous pyridine is cooled under an atmosphere of dry argon to 5°C, mixed over 30 minutes with 29 ml of benzoyl chloride and stirred for 1.5 hours at 23°C. It is poured on 600 ml of ice water, extracted several times with diethyl ether, the combined organic extracts are washed with 2 n hydrochloric acid, water and saturated sodium chloride solution and it is dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on about 2 1 of fine silica gel with a gradient system of n-hexane and ethyl acetate. 57.9 g (96.7 mmol, 100%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3040, 3000, 2950, 2930, 2850, 1735, 1710, 1600, 1450, 1425, 1360, 1310, 1270, 1110, 820, 740 and 705 cm1.

Example li: 7-((IR,2S,5S)-2-(tert-Butyldiphenylsilyloxymethyl)-5hydroxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: The solution of 154 g of the crude product, produced according to example lj, in 150 ml of acetone is mixed with 33.4 g of potassium carbonate, 41.2 g of methyl iodide and heated for 6 hours to 80°C. It is concentrated by evaporation, taken up in 400 ml of dichloromethane, washed with water and saturated sodium chloride solution and dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on about 2 1 of coarse silica gel with a gradient system of n-hexane and ethyl acetate. 47.9 g (96.8 mmol, 88% relative to the feedstock in example 1j) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 3040, 3000, 2940, 2920, 2850, 1735, 1585, 1460, 1425, 1240, 1165, 1110, 1005, 820, 740 and 700 Example li: 7-((IR,2S,5S)—2—(tert—Butyldiphenylsilyloxymethyl)-5hydroxy-cyclopentyl]-5(Z)-heptenoic acid: A total of 50 g of finely pulverized potassium-tertbutanolate is added over one hour in portions to the emulsion of 99.7 g of carboxybutyltriphenylphosphonium bromide in 256 ml of anhydrous tetrahydrofuran and 600 ml of anhydrous dimethyl sulfoxide. It is stirred until a clear red solution results, the solution of 43.8 g (110 mmol) of the compound, produced according to example lk, is instilled continuously in 130 ml of anhydrous tetrahydrofuran and is allowed to react for 2 hours at 23°C under an atmosphere of dry argon. It is poured in ice water, adjusted to a pH of 4-5 by adding a saturated citric acid solution and extracted several times with dichloromethane. It is washed with water and saturated sodium chloride solution, dried on magnesium sulfate, filtered and concentrated by evaporation. The resulting residue is further reacted without purification.

Example lk: (IS,3RS,5R,6S)-3-Hydroxy-6-(tertbutyldiphenylsilyloxymethyl)-2-oxabicyclo[3.3.0]-octane: The solution of 45.8 g (116 mmol) of the compound, produced according to example 11, in 1.4 1 of anhydrous toluene is cooled under an atmosphere of dry argon to -70°C, 202 ml of a 1.2 M diisobutylaluminum hydride solution is instilled in toluene within one hour and stirred for 1 hour. Excess reducing agent is decomposed by adding 13 ml of isopropanol. It is allowed to heat to 0°C, 100 ml of water is instilled and stirred at 23°C until a fine granular precipitate has formed. It is suctioned off, rewashed with dichloromethane and, after removal of the solvent, 43.8 g (110 mmol, 95%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 3050, 2940, 2850, 1590, 1465, 1425, 1390, 1360, 1260, 1110, 1010, 940, 820, 740 and 700 cm1.

Example 11: (IS,5R, 6S)-3-OXO-6-(tert-butyldiphenylsilyloxymethyl)-2oxabicyclo[3.3.0]octane: The solution of 67 g (119 mmol) of the tosylate, produced according to example lm, in 1.3 1 of dimethoxyethane is mixed with 136 g of sodium iodide, 118 g of zinc dust, 79 ml of water and refluxed for 16 hours. After the cooling, it is filtered off from undissolved residues, the filtrate is concentrated by evaporation to about 200 ml, it is mixed with water and extracted several times with diethyl ether. The combined organic extracts are washed with 10% sodium bisulfate solution, water, saturated sodium chloride solution and dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on about 2 1 of coarse silica gel with a gradient system of n-hexane and ethyl acetate. 45.8 g (116 mmol, 98%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3050, 2950, 2930, 2850, 1775, 1590, 1470, 1425, 1165, 1110, 1005, 820, 740 and 705 cm-1.

Example lm: (IS,5R,6S,7R)-3-Oxo-6-(tert-butyldiphenylsilyloxymethyl)-7toluenesulfonyloxy-2-oxabicyclo[3.3.OJoctane: The solution of 67.3 g (164 mmol) of the alcohol, produced according to example In, in 260 ml of anhydrous pyridine is mixed with 62.8 g of p-toluenesulfonic acid chloride and stirred for 27 hours under an atmosphere of dry argon at 50°C. It is concentrated by evaporation, mixed with water and extracted several times with dichloromethane. It is washed with water and saturated sodium chloride solution and dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on about 2 1 of coarse silica gel with a gradient system of n-hexane and ethyl acetate. 67 g (119 mmol, 72%) of the title compound is isolated as colorless oil.

IR (CHC13) : 3070, 3030, 2960, 2930, 2860, 1770, 1600, 1470, 1425, 1365, 1190, 1175, 1110, 1040, 980, 960, 895, 875, 820 and 700 cm-1.

Example In: (IS,5R,6S,7R)—3-Oxo—6—(tert-butyldiphenylsilyloxymethyl)-7hydroxy-2-oxabicyclo[3.3.0]octane: The solution of 129 g (251 mmol) of (IS,5R,6S,7R)-3-oxo-6(tert-butyldiphenylsilyloxymethyl)-7-benzoyloxy-2oxabicyclo[3.3.0]octane in 1 1 of methanol is mixed with 14.9 g of potassium carbonate and stirred for 3 hours at 23°C under an atmosphere of dry argon. It is mixed with water, neutralized by carefully adding 2 n hydrochloric acid, concentrated by evaporation and extracted several times with dichloromethane. It is washed with water, saturated sodium chloride solution and dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on about 2 1 of fine silica gel with a gradient system of n-hexane and ethyl acetate. 97 g (236 mmol, 94%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 3050, 2940, 2960, 1770, 1590, 1430, 1240, 1170, 1115, 1075, 825, 745, 705, 615 and 510 cm-1.

Example 2: 7-[(IR,2S,5R)-2-(4-Toluenesulfonylamino)-5-fluorocyclopentyl ]-5(Z)-heptenoic acid: The solution of 16 mg (44 micromol) of the compound, produced according to example 1, in 1 ml of methanol is mixed with 0.5 ml of a 5% lithium hydroxide solution and stirred for 1.5 hours at 23°C. It is acidified by adding saturated citric acid, diluted with water and extracted several times with dichloromethane. It is washed with water, saturated sodium chloride solution and dried on magnesium sulfate- The residue obtained after filtration and removal of the solvent is purified by chromatography on an analytic thin-layer slab. A mixture of dichloromethane and methanol is used as mobile solvent, a mixture of chloroform and isopropanol is used as eluant. 15.7 mg (41 micromol, 93%) of the title compound is isolated as colorless solid.

IR (KBr): 3600-2400, 3430, 3310, 3050, 3020, 2950, 2930, 2860, 1715, 1600, 1450, 1320, 1240, 1160, 1095, 920, 815, 670, 580 and 550 cm-1.

Example 3: 7-[(IR,2S,5R)—2—(Benzenesulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (210 micromol) of the compound produced according to example 3a is reacted analogously to example 1 and, after working up and purification, 23 mg (63 micromol, 30%) of 7-[5(S)(benzenesulfonylamino)-cyclopent-l-enyl]-5(Z)-heptenoic acid methyl ester as well as 26 mg (68 micromol, 32%) of the title compound are isolated as colorless oil.

IR (Film): 3430, 3310, 3040, 3020, 2950, 2860, 1730, 1600, 1450, 1320, 1240, 1160, 1095, 930, 755, 720 and 690 cm1.

Example 3a: 7-[(IR,2S,5S)-2-Benzenesulfonylamino-5-hydroxy-cyclopentyl]5(Z)-heptenoic acid methyl ester: 270 mg (556 micromol) of the compound produced according to example 3b is reacted analogously to example la and, after working up and purification, 212 mg (556 micromol, 100%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3260, 3060, 2930, 2850, 1725, 1445, 1320, 1265, 1160, 1090, 1020 and 735 cm1.

Example 3b: 7-[(IR,2S,5S)-2-Benzenesulfonylamino-5-benzoyloxycyclopentyl]-5(Z)-heptenoic acid methyl ester: 250 mg (724 micromol) of the compound produced according to example lc is reacted analogously to example lb with benzenesulfonic acid chloride and, after working up and purification, 270 mg (556 micromol, 77%) of the title compound is isolated as colorless oil.

IR (Film): 3270, 3060, 3000, 2950, 2860, 1730, 1715, 1600, 1585, 1450, 1330, 1315, 1270, 1160, 1110, 990, 1025, 910, 755, 715 and 690 cm’1.

Example 4: 7-((IR,2S,5R)-2-(Benzenesulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid: mg (68 micromol) of the compound produced according to example 3 is reacted analogously to example 2 and, after working up and purification, 23.6 mg (64 micromol, 94%) of the title compound is isolated as colorless oil.

^-NMR (CDClj) : cT = 1.5-2.2(m, 11H) , 2.34(t, 2H) , 3.33.45(m, 1H), 4.7(m, 1H), 5.1(s, NH), 5.2-5.5(m, 2H), 7.45-7.65(m, 3H), 7.9(m, 2H).

Example 5: 7-((IR,2S,5R)-2-(4-Fluorobenzenesulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (210 micromol) of the compound produced according to example 5a is reacted analogously to example 1 and, after working up and purification, 25 mg (66 micromol, 31%) of 7-[5(S)-(4fluorobenzylsulfonylamino)-cyclopent-l-enyl]-5(Z)-heptenoic acid methyl ester as well as 26 mg (65 micromol, 31%) of the title compound are isolated as colorless oil.

IR (Film): 3300, 3060, 3020, 2940, 2860, 1735, 1605, 1595, 1490, 1440, 1325, 1250, 1160, 835, 790, 735 and 700 cm1.

Example 5a; 7-[(IR,2S,5S)-2-(4-Fluorobenzenesulfonylamino)-5-hydroxycyclopentyl]-5(Z)-heptenoic acid methyl ester: 240 mg (477 micromol) of the compound produced according to example 5b is reacted analogously to example lb and, after working up and purification, 175 mg (438 micromol, 92%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3310, 3060, 3020, 2940, 2860, 1730, 1610, 1595, 1490, 1440, 1325, 1250, 1160, 835, 790, 740 and 700 Example 5b: 7-[(IR,2S,5S)-2-(4-Fluorobenzenesulfonylamino)-5-benzoyloxycyclopentyl]-5(Z)-heptenoic acid methyl ester: 250 mg (724 micromol) of the compound produced according to example lc is reacted analogously to example lb with 4fluorobenzenesulfonic acid chloride and, after working up and purification, 243 mg (483 micromol, 67%) of the title compound is isolated as colorless oil.

IR (Film): 3270, 3060, 3000, 2950, 2870, 1730, 1710, 1590, 1570, 1490, 1450, 1335, 1270, 1165, 1150, 1090, 1025, 910, 715 and 670 cm’1.

Example 6: 7-[(IR,2S,5R)-2-(4-Fluorobenzenesulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid: mg (65 micromol) of the compound produced according to example 5 is reacted analogously to example 2 and, after working up and purification, 22.5 mg (58 micromol, 89%) of the title compound is isolated as colorless oil.

^-NMR (CDC13) : S = 1.5-2.2(m, 11H) , 2.35(t, 2H) , 3.33.45(m, 1H), 4.7(m, 1H), 5.15(s, NH), 5.25-5.5(m, 2H), 7.1-7.3(m, 2H), 7.9(m, 2H).

Example 7: 7-[(IR,2S,5R)-2-(Quinon-8-ylsulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (171 micromol) of the compound produced according to example 7a is reacted analogously to example 1 and, after working up and purification, 29 mg (70 micromol, 41%) of 7-[5(S)-(quinon8-ylsulfonylamino)-cyclopent-l-enyl]-5(Z)-heptenoic acid methyl ester as well as 19 mg (44 micromol, 25%) of the title compound are isolated as colorless oil.

IR (Film): 3270, 3060, 2950, 2860, 1730, 1610, 1595, 1365, 1490, 1435, 1330, 1265, 1160, 1145, 835, 790, 735 and 700 cm'1.

Example 7a: 7-[(IR,2S,5S)-2-(Quinon-8-ylsulfonylamino)-5-hydroxycyclopentyl]-5(Z)-heptenoic acid methyl ester: 339 mg (632 micromol) of the compound produced according to example 7b is reacted analogously to example la and, after working up and purification, 259 mg (596 micromol, 94%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3280, 3060, 3000, 2940, 2860, 1730, 1665, 1610, 1595, 1565, 1490, 1435, 1325, 1215, 1165, 1145, 1090, 835 and 790 cm'.

Example 7b: 7-((IR,2S,5S)-2-(Quinon-8-ylsulfonylamino)-5-benzoyloxycyclopentyl]-5(Z)-heptenoic acid methyl ester: 250 mg (724 micromol) of the compound produced according to example lc is reacted analogously to example lb with guinon-8ylsulfonic acid chloride and, after working up and purification, 339 mg (632 micromol, 87%) of the title compound is isolated as colorless oil.

IR (Film): 3270, 3060, 2950, 2860, 1730, 1710, 1675, 1600, 1565, 1490, 1450, 1435, 1330, 1270, 1245, 1165, 1145, 1110, 1070, 1045, 1025, 900, 835, 790 and 715 cm1.

Example 8; 7-((1R,2S,5R)-2-(Quinon-8-ylsulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid: mg (44 micromol) of the compound produced according to example 7 is reacted analogously to example 2 and, after working up and purification, 14 mg (33 micromol, 77%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3290, 3060, 2950, 2860, 1710, 1610, 1590, 1360, 1490, 1435, 1330, 1265, 1160, 1145, 835, 790, 735 and 700 cm-1.

Example 9: 7-[(IR,2S,5R)-2-(Benzenesulfonylamino)-5-fluorocyclopentyl]-heptanoic acid methyl ester: 109 mg (284 micromol) of the compound produced according to example 18 is reacted analogously to example 1 and, after working up and purification, 42 mg (115 micromol, 40%) of 7-[5(S)(benzenesulfonylamino)-cyclopent-l-enyl]-heptanoic acid methyl ester as well as 34 mg (88 micromol, 31%) of the title compound are isolated as colorless oil.

IR (Film): 3370, 3060, 2930, 2860, 1725, 1440, 1325, 1160, 1090, 1070, 930, 755, 720 and 690 cm'1.

Example 10: 7-[ (IR, 2S, 5R) -2-(Benzenesulfonylami.no) -5-fluorocyclopentyl]-heptanoic acid: mg (88 micromol) of the compound produced according to example 9 is reacted analogously to example 2 and, after working up and purification, 29 mg (78 micromol, 89%) of the title compound is isolated as colorless oil. ’h-NMR (CDC13): J' = 1.0-1.35(m, 7H), 1.5-2.05(m, 8H), 2.35(t, 2H), 3.3-3.45(m, 1H), 4.7(m, 1H), 4.93(d, NH), 7.457.65(m, 3H), 7.88(m, 2H).

Example 11: 7-[(IR,2S,5R)-2-(4-Fluorobenzenesulfonylamino)-5-fluorocyclopentyl]-heptanoic acid methyl ester: 120 mg (299 micromol) of the compound produced according to example 19 is reacted analogously to example 1 and, after working up and purification, 44 mg (115 micromol, 38%) of 7-[5(S)-(4fluorobenzylsulfonylamino)-cyclopent-l-enyl]-heptanoic acid methyl ester as well as 33 mg (82 micromol, 27%) of the title compound are isolated as colorless oil.

IR (Film): 3370, 3070, 2930, 2860, 1730, 1665, 1595, 1490, 1450, 1435, 1330, 1290, 1230, 1160, 1090, 1115, 950, 925, 840 and 820 cm1 .

Example 12: 7-[(IR,2S,5R)-2-(4-Fluorobenzenesulfonylamino)-5-fluorocyclopentyl]-heptanoic acid: mg (82 micromol) of the compound produced according to example 11 is reacted analogously to example 2 and, after working up and purification, 31 mg (80 micromol, 97%) of the title compound is isolated as colorless oil. lH-NMR (CDC13) : 7.9(m, 2H).

Example 13: 7-[(IR,2S,5R)—2—(Quinon—8—ylsulfonylamino)-5-fluorocyclopentyl]-heptanoic acid methyl ester: mg (179 micromol) of the compound produced according to example 20 is reacted analogously to example 1 and, after working up and purification, 24 mg (57 micromol, 32%) of 7-[5(S)-(quinon8-ylsulfonylamino)-cyclopent-l-enyl]-heptanoic acid methyl ester as well as 19 mg (43 micromol, 24%) of the title compound are isolated as colorless oil.

IR (Film): 3270, 3060, 2940, 2850, 1730, 1610, 1595, 1565, 1490, 1435, 1330, 1160, 1140, 835, 795, 735 and 680 cm'1.

Example 14: 7-[(IR,2S, 5R)-2-(Quinon-8-ylsulfonylamino)-5-fluorocyclopentylj-heptanoic acid: mg (73 micromol) of the compound produced according to example 13 is reacted analogously to example 2 and, after working up and purification, 26 mg (62 micromol, 84%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2500, 3400, 3280, 2920, 2850, 1705, 1600, 1510, 1460, 1290, 1085, 1055, 1030 and 735 cm-1.

Example 15: 7-[(1R,2S,5R)-2-(4-Toluenesulfonylamino)-5-hydroxycyclopentyl]-5(Z)-heptenoic acid methyl ester: The solution of 241 mg (612 micromol) of the compound produced according to example 15a is dissolved in 8 ml of anhydrous methanol, cooled under an atmosphere of dry argon to —30°C and mixed in portions with a total of 69 mg of sodium borohydride. It is allowed to react for another 30 minutes, excess reducing agent is decomposed by adding 120 microliters of acetic acid, it is mixed with water and extracted several times with dichloromethane. It is washed with water, saturated sodium chloride solution and dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on 12 analytic thin-layer slabs. A mixture of n-hexane and ethyl acetate is used as mobile solvent, diethyl ether is used as eluant. 108 mg (273 micromol, 45%) of the title compound is isolated as a more polar component, and 48 mg (121 micromol, 20%) of the title compound of example la is isolated as a more nonpolar component.

IR (Film): 3600-3200, 2950, 2920, 2850, 1730, 1600, 1450, 1325, 1155, 1090, 895, 815, 735 and 670 cm'1.

Example 15a: 7-((IR,2S)—2—(4-Toluenesulfonylamino)-5-oxo-cyclopentyl]5(Z)-heptenoic acid methyl ester: 245 mg (619 micromol) of the compound produced according to example la is oxidized analogously to example If and, after working up, 241 mg (612 micromol, 99%) of the title compound is isolated as pale yellow oil.

IR (Film): 3360, 2950, 2920, 2850, 1735, 1600, 1450, 1325, 1155, 1090, 900, 815, 735 and 665 cm'1.

Example 16: 7-((IR,2S,5S)-2-(4-Toluenesulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid methyl ester: 108 mg (273 micromol) of the compound produced according to example 15 is reacted analogously to example 1 and, after working up and purification, 9 mg (24 micromol, 9%) of 7-(5(S)-(4toluenesulfonylamino)-cyclopent-l-enylJ-5(Z)-heptenoic acid methyl ester as well as 23 mg (60 micromol, 22%) of the title compound are each isolated as colorless oil.

IR (Film): 3250, 3010, 2960, 2930, 2870, 1730, 1600, 1450, 1380, 1325, 1305, 1290, 1240, 1160, 1095, 925, 910, 815 and 665 Example 17: 7-((1R,2S,5s)-2-(4-Toluenesulfonylamino)-5-fluorocyclopentyl]-5(Z)-heptenoic acid: mg (76 micromol) of the compound produced according to example 16 is saponified analogously to example 2 and, after working up and purification, 14 mg (37 micromol, 48%) of the title compound is isolated as colorless oil.

IR (Film): 3700-2400, 3260, 3010, 2960, 2930, 2870, 1710, 1600, 1450, 1405, 1380, 1325, 1305, 1290, 1240, 1160, 1095, 925, 910, 815, 665, 620 and 550 cm1.

Example 18: 7-((IR,2S,5S)-2-(Benzenesulfonylamino)-5-hydroxycyclopentyl]-heptanoic acid methyl ester: 132 mg (346 micromol) of the compound produced according to example 3a is dissolved in 5 ml of ethyl acetate, mixed with 50 mg of Pd/C (5%) and hydrogenated at 1 atm, until the theoretically calculated amount of hydrogen is taken up. It is filtered, rewashed, and concentrated by evaporation. 109 mg (284 micromol, 82%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3260, 2930, 2850, 1725, 1445, 1320, 1265, 1160, 1095, 1020 and 735 cm-1.

Example 19: 7-[(IR,2S,5S)-2-(4-Fluorobenzenesulfonylamino)-5-hydroxycyclopentyl]-heptenoic acid methyl ester: 141 mg (355 micromol) of the compound produced according to example 5a is hydrogenated analogously to example 18 and, after working up, 120 mg (300 micromol, 84%) of the title compound is isolated as colorless oil.

IR (Film): 3270, 2930, 2850, 1730, 1660, 1600, 1445, 1320, 1260, 1160, 1095, 1020, 925, 840 and 820 cm-1.

Example 20: 7-((IR,2S,5S)-2-(Quinon-8-ylsulfonylamino)-5-hydroxycyclopentyl]-heptanoic acid methyl ester: 149 mg (344 micromol) of the compound produced according to example 7a is hydrogenated analogously to example 18 and, after working up, 142 mg (327 micromol, 95%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3520, 3410, 3280, 2940, 2850, 1725, 1665, 1595, 1490, 1455, 1430, 1320, 1160, 1140, 1020, 890, 840, 790, 735 and 675 cm1 .

Example 21: 7-((IR,2S,5S)-2-(Quinon-8-ylsulfonylamino)-5-hydroxycyclopentyl]-heptanoic acid: mg (69 micromol) of the compound produced according to example 20 is saponified analogously to example 2 and, after working up and purification, 25 mg (59 micromol, 86%) of the title compound is isolated as colorless oil. ’h-NMR (CDC13) : = 1.0-1.9(m, 16H), 2.32(t, 2H), 3.4(m, 1H), 4.12(m, 1H), 6.27(d, NH), 7.57(dt, 1H), 7.66(t, 1H), 8.06(dd, 1H), 8.3(dd, 1H), 8.43(dd, 1H), 9.03(dd, 1H).

Example 22: 7-((1R,2S,5S)-2-(4-Toluenesulfonylamino)-5-hydroxycyclopentyl]-5(Z)-heptenoic acid: mg (119 micromol) of the compound produced according to example lb is saponified analogously to example 2 and, after working up and purification, 41 mg (107 micromol, 90%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3470, 3260, 3000, 2940, 2870, 1710, 1600, 1445, 1320, 1160, 1095, 910, 810, 670, 570 and 550 cm'1.

Example 23: 7-((IR,2S,5S)—2—(Quinon-8-ylsulfonylamino)-5-hydroxycyclopentyl]-5(Z)-heptenoic acid: mg (44 micromol) of the compound produced according to example 7b is saponified analogously to example 2 and, after working up and purification, 16 mg (38 micromol, 85%) of the title compound is isolated as waxy solid. ’h-NMR (CDC13) : cP = 1.0-2.35(m, 14H), 3.43(m, 1H), 4.1(m, 1H) , 5.15-5.35(m, 2H), 6.47(d, NH), 7.52(dd, 1H) , 7.66(t, 1H), 8.04(dd, 1H), 8.27(dd, 1H), 8.43(dd, 1H), 9.03(dd, 1H).

Example 24: 7-((IR,2S,3RS,5R)-2-Benzyloxymethyl-3-phenyl-5-fluorocyclopentyl]-5(E/Z)-heptenoic acid: mg (99 micromol) of the compound produced according to example 24a is mixed with 0.4 ml of a 50% KOH solution, 257 microliters of benzyl chloride, 4 mg of tetrabutylammonium hydrogen sulfate and it is stirred intensively for 18 hours at 23°C. It is poured in ice water, extracted several times with dichloromethane, the organic phase is dried on magnesium sulfate and excess benzyl chloride is removed by chromatography on 4 analytic thin-layer slabs. A mixture of n-hexane and ethyl acetate is used as mobile solvent, chloroform is used as eluant. The resulting residue is saponified analogously to example 2 and, after working up and purification, 17 mg (41 micromol, 42%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2930, 2850, 1710, 1600, 1495, 1455, 1360, 1240, 1210, 1100, 970, 755, 735 and 700 cm'1. 4S Example 24a: 7-((IR,2S,3RS,5R)-2-Hydroxymethyl-3-phenyl-5-fluorocyclopentyl]-5(E/Z)-heptenoic acid methyl ester: 305 mg (532 micromol) of the compound produced according to example 24b is reacted analogously to example lg and, after working up and purification, 176 mg (526 micromol, 99%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3030, 2920, 2850, 1730, 1450, 1435, 1370, 1150, 1045, 755 and 700 cm'1.

Example 24b: 7-((IR,2S,3RS,5R)-2-(tert-Butyldiphenylsilyloxymethyl)-3phenyl-5-fluoro-cyclopentyl]-5(E/Z)-heptenoic acid methyl ester: 742 mg (1.30 mmol) of the compound produced according to example 24c is reacted analogously to example 1 and, after working up and purification, 294 mg (532 micromol, 41%) of 7((4RS,5S)-4-phenyl-5-(tert-butyldiphenylsilyloxymethyl)cyclopent-l-enyl]-5(E/Z)-heptenoic acid methyl ester as well as 337 mg (588 micromol, 45%) of the title compound are isolated as colorless oil.

IR (Film): 3070, 3030, 2960, 2930, 2860, 1735, 1600, 1590, 1425, 1110, 820, 740 and 700 cm'1.

Example 24c: 7—[(IR,2S,3RS,5S)-2-(tert-Butyldiphenylsilyloxymethyl)-3phenyl-5-hydroxy-cyclopentyl3-5(E/Z)-heptenoic acid methyl ester (A) and 7-[(lR,2S,3RS,5R)-2-(tert-butyldiphenylsilyloxymethyl)-3phenyl-5-hydroxy-cyclopentyl]-5(E/Z)-heptenoic acid methyl ester (B) : 1.97 g (3.47 mmol) of the compound produced according to example 24d is reacted analogously to example 15 and, after working up and purification, 742 mg (1.30 mmol, 37%) of title compound A as well as 925 mg (1.62 mmol, 47%) of title compound B are each isolated as colorless oil.

IR (Film) of A: 3600-3200, 3070, 3020, 2950, 2920, 2850, 1735, 1600, 1585, 1450, 1425, 1110, 820, 760, 740 and 700 cm'1.

IR (Film) Of B: 3600-3200, 3060, 3020, 2950, 2920, 2850, 1730, 1600, 1590, 1450, 1425, 1265, 1110, 1060, 820, 740 and 700 -i cm Example 24d: 7-[(IR,2S,3RS)-2-(tert-Butyldiphenylsilyloxymethyl)-3phenyl-5-oxo-cyclopentyl]-5(E/Z)-heptenoic acid methyl ester: The solution of 11.82 g (24.0 mmol) of the compound, produced according to example 24e, in 120 ml of anhydrous tetrahydrofuran is mixed with 500 mg of copper(II) acetate and cooled under an atmosphere of dry argon to -78°C. 3.04 ml of trimethylchlorosilane and then 12.8 ml of a 3 M solution of phenylmagnesium bromide in diethyl ether are added. After 45 minutes, it is poured in saturated ammonium chloride solution and extracted several times with dichloromethane. The combined organic extracts are dried on magnesium sulfate and the residue obtained after removal of the solvent is purified by chromatography on about 200 ml of fine silica gel. A gradient system of n-hexane and ethyl acetate is used as mobile solvent. 9.78 g (17.2 mmol, 72%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3030, 2950, 2930, 2850, 1735, 1600, 1465, 1450, 1425, 1110, 1055, 820, 780, 740 and 700 cm*.

Example 24e: 7-((IR,2S)-2-(tert-Butyldiphenylsilyloxymethyl)-5-oxocyclopent-3-enyl]-5(E/Z)-heptenoic acid methyl ester: The solution of 5.84 g (11.5 mmol) of the compound, produced according to example 24f, in 52 ml of anhydrous pyridine is cooled under an atmosphere of dry argon to 3°C, 2.17 ml of methanesulfonic acid chloride is instilled and it is stirred for another 2 hours at 3°C. It is mixed with ice, diluted with water and extracted several times with dichloromethane. The combined organic extracts are dried on magnesium sulfate and the residue obtained after removal of the solvent is purified by chromatography on about 200 ml of fine silica gel. A gradient system of n-hexane and ethyl acetate is used as mobile solvent. 4.93 g (10.0 mmol, 87%) of the title compound is isolated as colorless oil. ί IR (Film): 3070, 3040, 2950, 2930, 2850, 1735, 1705, 1585, 1425, 1110, 820, 740 and 700 cm1.

Example 24f: 7-[(IR,2S,3R)-2-(tert-Butyldiphenylsilyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-oxo-cyclopentyl]-5(E/Z)-heptenoic acid methyl ester: 11.9 g (20.0 mmol) of the compound produced according to example 24g is reacted analogously to example If and, after working up and purification, 9.39 g (15.8 mmol, 79%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3040, 2940, 2850, 1740, 1590, 1425, 1110, 1075, 1030, 970, 820, 740 and 700 cm1.

Example 24g: 7-[(IR,2S,3R,5S)-2-(tert-Butyldiphenylsilyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(E/Z)-heptenoic acid methyl ester: 22.4 g (47.8 mmol) of (IS,3RS,5R,6S,7R)-7-(tetrahydropyran2-yloxy)-6-(tert-butyldiphenylsilyloxymethyl)-2oxabicyclo[3.3.0]octan-3-ol is reacted analogously to example lj with use of potassium-tert-butanolate containing KOH and, after working up and esterification with an ethereal solution of diazomethane after chromatographic purification on about 1.3 1 of fine silica gel with a gradient system of n-hexane and ethyl acetate, 21.6 g (36.3 mmol, 76%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 3040, 2940, 2850, 1730, 1595, 1425, 1110, 1075, 1025, 970, 820, 740 and 700 cm'1.

Example 25: 7-((IR,2S,3RS,5R)-2-(4-Cyanobenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(E/Z)-heptenoic acid: mg (84 micromol) of the compound produced according to example 24a is reacted analogously to example 24 with use of 4cyanobenzyl bromide and, after working up and purification, 14 mg (32 micromol, 38%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3015, 1930, 2860, 2230, 1705, 1600, 1455, 1435, 1360, 1290, 1240, 1150, 1110, 1090, 970, 795, 755, 700 and 685 cm1.

Example 26: 7-[(IR,2S,3RS,5R)-2-(3-Methylbenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(E/Z)-heptenoic acid: mg (81 micromol) of the compound produced according to example 24a is reacted analogously to example 24 with use of 3methylbenzyl bromide and, after working up and purification, 23 mg (54 micromol, 67%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2930, 2860, 1705, 1600, 1450, 1360, 1245, 1160, 1105, 1090, 970, 780, 755 and 700 cm'1.

Example 27: 7-((lR,2S,3RS,5R)-2-(3,5-bisTrifluoromethylbenzyloxymethyl)-3-phenyl-5-fluoro-cyclopentyl]5(E/Z)-heptenoic acid: mg (87 micromol) of the compound produced according to example 24a is reacted analogously to example 24 with use of 3,5bis(trifluoromethyl)benzyl bromide and, after working up and purification, 28 mg (51 micromol, 59%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2930, 2870, 1710, 1625, 1600, 1455, 1380, 1355, 1280, 1175, 1135, 970, 885, 840, 760, 700 and 680 cm'1.

Example 28: 7-[ (IR, 2S,3RS,5R)-2-(1-Naphthylmethoxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(E/Z)-heptenoic acid: mg (87 micromol) of the compound produced according to example 24a is reacted analogously to example 24 with use of lbromomethylnaphthalene and, after working up and purification, mg (56 micromol, 65%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3010, 2930, 2860, 1705,1600, 1455, 1240, 1165, 1100, 970, 800, 790, 775, 755 and 700 cm"1 .

Example 29: 7-[(IS,2R,3RS,5S)-2-[2-(4-Fluorophenoxy)-ethoxymethyl]-3phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (129 micromol) of the compound produced according to example 29a is reacted analogously to example 24 with use of 1bromo-2-(4-fluorophenoxy)-ethane and, after working up and purification, 12 mg (26 micromol, 20%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3010, 2930, 2870, 1710, 1600, 1505, 1455, 1250, 1210, 1130, 100, 1050, 830, 760, 745 and A 700 cm1.

Example 29a: 7-[(IS,2R,3RS,5S)-2-Hydroxymethyl-3-phenyl-5-fluorocyclopentyl ]-5(Z)-heptenoic acid: 2.36 g (4.12 mmol) of the compound produced according to example 29b is reacted analogously to example lg and, after working up and purification, 1.24 g (3.71 mmol, 90%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3020, 2920, 2850, 1730, 1600, 1450, 1435, 1330, 1150, 1045, 965, 755 and 700 cm1.

Example 29b: 7-( (IS, 2R, 3RS, 5S) -2-(tert-Butyldiphenylsilyloxymethyl) -3phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: Starting from (IR,3RS,5S,6R,7S)-7-(tetrahydropyran-2-yloxy)6- (tert-buty ldipheny lsily loxymethyl) -2-oxabicyclo [3.3.0] octan-3ol, 7-( (4RS, 5R)-4-phenyl-5-(tert-butyldiphenylsilyloxymethyl) cyclopent-l-enyl]-5(Z)heptenoic acid methyl ester as well as the title compound are produced analogously to the described examples 24b to 24g. With use of freshly sublimated potassium-tertbutanolate (cf. example 24g), only the Z isomer is obtained relative to the double bond in 5 in each case.

Example 30: 7-((IS,2R,3RS,5S)-2-Benzyloxymethyl-3-phenyl-5-fluorocyclopenty1]-5(Z)-heptenoic acid: 6 mg (129 micromol) of the compound produced according to example 29a is reacted analogously to example 24 and, after working up and purification, 25 mg (61 micromol, 47%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3010, 2930, 2860, 1710, 1600, 1495, 1455, 1360, 1240, 1210, 1100, 755, 735 and 700 cm1.

Example 31: 7-((IS,2R,3RS,5S)-2-(4-Cyanobenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (129 micromol) of the compound produced according to example 29a is reacted analogously to example 24 with use of 4cyanobenzyl bromide and, after working up and purification, 31 mg (71 micromol, 55%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2940, 2860, 2230, 1710, 1610, 1450, 1235, 1220, 1130, 1100, 820, 760 and 700 cm-1.

Example 32: 7-[(IS,2R,3RS,5S)-2-(3-Methylbenzyloxymethyl)-3-pheny1-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (129 micromol) of the compound produced according to example 29a is reacted analogously to example 24 with use of 3methylbenzyl bromide and, after working up and purification, 26 mg (61 micromol, 47%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3010, 2940, 2860, 1710, 1600, 1495, 1455, 1360, 1250, 1160, 1105, 1090, 780, 760 and 700 Example 33; 7-((IS,2R,3RS,5S)-2-(3-CyanobenzyloxymethyI)-3-phenyl-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (129 micromol) of the compound produced according to example 29a is reacted analogously to example 24 with use of 3cyanobenzyl bromide and, after working up and purification, 36 mg (83 micromol, 64%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3010, 2930, 2860, 2230, 1710, 1600, 1495, 1455, 1435, 1360, 1240, 1150, 1105, 1090, 795, 760, 700 and 685 cm*1.

Example 34: 7-((IR,2S,3RS,5S)-2-[2-(4-Fluorophenoxy)-ethoxymethyl]-3phenyl-5-fluoro-cyclopentyl]-5(E/Z)-heptenoic acid: mg (99 micromol) of the compound produced according to example 34b is reacted analogously to example 24 with use of 1bromo-2-(4-fluorophenoxy)-ethane and, after working up and purification, 17 mg (37 micromol, 37%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3000, 2930, 2870, 2850, 1710, 1600, 1505, 1455, 1250, 1210, 1140, 995, 1050, 825, 760, 745 and 700 cm1.

*E 912654 Example 34a: 7-((IR,2S,3RS,5S)-2-Hydroxymethyl-3-phenyl-5-fluorocyclopentyl]-5(E/Z)-heptenoic acid methyl ester: 586 mg (1.02 mmol) of the compound produced according to example 34b is reacted analogously to example lg and, after working up and purification, 335 mg (1.00 mmol, 98%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3060, 3030, 3000, 2940, 2870, 1735, 1600, 1490, 1450, 1435, 1245, 1175, 1065, 1045, 1030, 945, 865, 760 and 700 cm-1.

Example 34b: 7-((IR,2S,3RS,5S)-2-(tert-Butyldiphenylsilyloxymethyl)-3phenyl-5-fluoro-cyclopentyl]-5(E/Z)-heptenoic acid methyl ester: 925 mg (1.62 mmol) of more polar compound B produced according to example 24c is reacted analogously to example 1 and, after working up and purification, 98 mg (165 micromol, 10%) of 7-[(4RS,5S)-4-phenyl-5-(tert-butyldiphenylsilyloxymethyl)cyclopent-l-enyl]-5(E/Z)-heptenoic acid methyl ester as well as 586 mg (1.04 mmol, 64%) of the title compound are isolated as colorless oil.

IR (Film): 3070, 3020, 3000, 2950, 2930, 2850, 1735, 1600, 1585, 1490, 1465, 1450, 1425, 1360, 1110, 1005, 965, 870, 820, 760, 740 and 700 cm'1.

Example 35: 7-((IR, 2S,3RS,5S)-2-Benzyloxymethyl-3-phenyl-5-fluorocyclopentyl ]-5(E/Z)-heptenoic acid: mg (93 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of benzyl chloride, and, after working up and purification, 14 mg (34 micromol, 37%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3020, 2930, 2850, 1705, 1600, 1490, 1465, 1100, 1070, 1030, 950, 760, 735 and 700 cm'1.

Example 36: 7-((lR,2S,3RS,5S)-2-(3,5-bisTrifluoromethylbenzyloxymethyl)-3-phenyl-5-fluoro-cyclopentyl]5(E/Z)-heptenoic acid: mg (75 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of 3,5bis-(trifluoromethyl)-benzyl bromide and, after working up and purification, 27 mg (49 micromol, 66%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3070, 3030, 2940, 2860, 1710, 1610, 1600, 1360, 1280, 1180, 1140, 700 and 680 cm'1.

Example 37: 7-((IR,2S,3RS,5S)-2-(1-Naphthylmethoxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(E/Z)-heptenoic acid: mg (69 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of 1bromomethylnaphthalene and, after working up and purification, 13 mg (28 micromol, 41%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3020, 3000, 2930, 2850, 1710, 1600, 1505, 1455, 1250, 1220, 1100, 950, 800, 790, 780, 760 and 700 cm1.

Example 38: 7-[ (IR,2S,3RS,5S)-2-(4-Cyanobenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(E/Z)-heptenoic acid: mg (60 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of 4cyanobenzyl bromide and, after working up and purification, 10 mg (24 micromol, 44%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2930, 2850, 2220, 1710, 1605, 1505, 1495, 1455, 1415, 1130, 1100, 950, 820, 760 and 700 Example 39; 7—((IR,2S,3RS,5S)-2-(3-Methylbenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(E/Z)-heptenoic acid; mg (60 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of 3methylbenzyl bromide and, after working up and purification, mg (38 micromol, 63%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2930, 2850, 1710, 1600, 1495, 1455, 1435, 1240, 1155, 1100, 1090, 950, 760 and 700 cm'1.

Example 40: 7-((IR, 2S,3RS,5S)-2-(3-Cyanobenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(E/Z)-heptenoic acid: mg (60 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of 3cyanobenzyl bromide and, after working up and purification, 17 mg (39 micromol, 65%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2930, 2860, 2230, 1710, 1600, 1585, 1455, 1435, 1355, 1285, 1200, 1150, 1105, 1085, 795, 760, 700 and 685 cm'1. 2 Example 41: 7-[(IS,2R,3RS,5R)-2-[2-(4-Fluorophenoxy)-ethoxymethyl] -3 phenyl-5-fluoro-cyclopenty1]-5(Z)-heptenoic acid: mg (128 micromol) of the compound produced according to example 41a is reacted analogously to example 24 with use of 4fluorophenoxyethyl bromide and, after working up and purification, 12 mg (26 micromol, 20%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3070, 3030, 2930, 2870, 1710, 1600, 1505, 1455, 1250, 1210, 1140, 1100, 1055, 830, 760, 750 and 700 Example 41a: 7-((IS,2R,3RS,5R)-2-Hydroxymethyl-3-phenyl-5-fluorocyclopentyl] -5(Z)-heptenoic acid: 3.63 g (6.34 mmol) of the compound produced according to example 41b is reacted analogously to example lg and, after working up and purification, 2.05 g (2.04 mmol, 95%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3060, 3030, 3000, 2940, 2870, 1735, 1600, 1490, 1450, 1435, 1245, 1220, 1170, 1150, 1070, 1045, 945, 870, 760 and 700 cm'1.

Example 41£>1 - [(IS,2R,3RS,5R)-2-(tert-Butyldiphenylsilyloxymethyl)-3phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: 6.15 g (10.8 mmol) Of 7-[(IS,2R,3RS,5S)-2-(tertbutyldiphenylsilyloxymethyl)-3-phenyl-5-hydroxy-cyclopentyl ] 5(Z)-heptenoic acid methyl ester, which is obtained in the course of the synthesis described under example 29b analogously to example 24c, is reacted analogously to example 1, and, after working up and purification, 610 mg (1.1 mmol, 10%) of 7[(4RS,5R)-4-phenyl-5-(tert-butyldiphenylsilyloxymethyl)cyclopent-l-enyl]-5(Z)-heptenoic acid methyl ester as well as 3.63 g (6.34 mmol, 59%) of the title compound are isolated as colorless oil.

IR (Film): 3070, 3020, 2950, 2930, 2850, 1735, 1600, 1585, 1425, 1110, 820, 760, 740 and 700 cm'1.

Example 42: 7-[(IS,2R,3RS,5R)-2-Benzyloxymethyl-3-phenyl-5-fluorocyclopentyl]-5(Z)-heptenoic acid: mg (129 micromol) of the compound produced according to example 41a is reacted analogously to example 24 with use of benzyl chloride and, after working up and purification, 23 mg (56 micromol, 43%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2940, 2860, 1710, 1600, 1495, 1450, 1100, 760, 740 and 700 cm'1.

Example 43-?. 7-((IS,2R,3RS,5R)-2-(4-Cyanobenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (129 micromol) of the compound produced according to example 41a is reacted analogously to example 24 with use of 4cyanobenzyl bromide and, after working up and purification, 21 mg (48 micromol, 37%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2940, 2860, 2230, 1710, 1610, 1455, 1275, 1130, 1100, 820, 780 and 700 cm1.

Example 44: 7-( (IS,2R,3RS,5R)-2-(3-Methylbenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (129 micromol) of the compound produced according to example 41a is reacted analogously to example 24 with use of 3methylbenzyl bromide and, after working up and purification, 21 mg (49 micromol, 38%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2930, 2850, 1710, 1600, 1455, 1240, 1160, 1100, 950, 780, 760 and 700 cm1.

Example 45: 7-((IS,2R,3RS,5R)-2-(3-Cyanobenzyloxymethyl)-3-phenyl-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (129 micromol) of the compound produced according to example 41a is reacted analogously to example 24 with use of 3cyanobenzyl bromide and, after working up and purification, 41 mg (94 micromol, 73%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2940, 2860, 2230, 1710, 1600, 1580, 1450, 1430, 1360, 1240, 1150, 1110, 1090, 950, 795, 760, 700 and 690 cm-1.

Example 46: 7-[(lR,2S,3RS,5S)-2-(2,4-bisTrifluoromethylbenzyloxymethyl)-3-phenyl-5-fluoro-cyclopentyl]5(E/Z)-heptenoic acid: mg (60 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of 2,4bis-(trifluoromethyl)-benzyl bromide and, after working up and purification, 20 mg (37 micromol, 61%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3030, 3000, 2920, 2850, 1710, 1630, 1600, 1455, 1345, 1275, 1170, 1130, 1055, 910, 860, 840, 760 and 700 cm’1 .

Example 47: 7-((IR,2S,3RS,5S)-2-(4-Methylbenzyloxymethyl)-3-phenyl-5fluoro-cyclopenty1]-5(E/Z)-heptenoic acid: mg (60 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of 4methylbenzyl bromide and, after working up and purification, mg (35 micromol, 59%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3020, 3000, 2920, 2850, 1705, 1600, 1455, 1100, 1085, 1070, 950, 800, 760 and 700 cm’1.

Example 48: 7-((IR,2S,3RS,5S)-2-(2-Naphthylmethoxymethyl)-3-pheny1-5fluoro-cyclopentyl]-5(Z)-heptenoic acid (A) and 7((IR,2S,3RS,5S)-2-(2-naphthylmethoxymethyl)-3-phenyl-5-fluorocyclopentyl ]-5(E)-heptenoic acid (B): mg (60 micromol) of the compound produced according to example 34a is reacted analogously to example 24 with use of 2bromomethylnaphthalene and, after working up and purification, mg (33 micromol, 50%) of title compound A as well as 7 mg (14 micromol, 21%) of title compound B are each isolated as colorless oil.

IR (Film) Of A: 3600-2400, 3060, 3020, 2930, 2850, 1705, 1600, 1490, 1455, 1435, 1410, 1345, 1270, 1240, 1125, 1100, 950, 855, 820, 755 and 700 cm-1.

IR (Film) of B: 3600-2400, 3060, 3030, 2930, 2850, 1705, 1600, 1455, 1435, 1410, 1345, 1125, 1100, 1090, 1070, 970, 950, 855, 815, 755 and 700 cm1.

Example 49: 7-((IR,2S,3RS,5R)-2-[2-(4-Fluorophenoxy)-ethoxymethyl]-3phenyl-5-fluoro-cyclopentyl]-5(E/Z)-heptenoic acid: mg (93 micromol) of the compound produced according to example 24a is reacted analogously to example 24 with use of 1bromo-2-(4-fluorophenoxy)-ethane and, after working up and purification, 15 mg (32 micromol, 35%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2930, 2870, 1710, 1600, 1505, 1455, 1250, 1210, 1130, 825, 760, 740 and 700 cm-1.

Example 50: 7-((1R,2S,3RS,5S)-2-((3RS,4S)-3-Hydroxy-4-methyl-non-l(E)en-6-inyl]-3-phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester (A) and 7-((IR,2S,3RS,5S)-2-((3RS,4S)-3-hydroxy-4methyl-non-1(E)-en-6-inyl]-3-phenyl-5-fluoro-cyclopentyl]-5(E)heptenoic acid methyl ester (B) : mg (91 micromol) of the compound produced according to example 50a is reacted analogously to example 15 and, after working up and purification, 21 mg (46 micromol, 51%) of title compound A as well as 15 mg (33 micromol, 36%) of title compound B are each isolated as colorless oil.

IR (Film): 3600-3200, 3060, 3030, 2970, 2930, 2850, 1735, 1600, 1495, 1450, 1240, 1125, 970, 760 and 700 cm'1.

Example 50a: 7-((IR,2S,3RS,5S)-2-[3-Oxo-4S-methyl-non-l(E)-en-6-inyl]-3phenyl-5-fluoro-cyclopentyl]-5(E/Z)-heptenoic acid methyl ester: The solution of 45 mg of dimethyl-(2-oxo-3S-methyl-oct-5inyl)-phosphonate in 330 microliters of tetrahydrofuran is instilled in the suspension of 8 mg of sodium hydride dispersion (55%) in 410 microliters of anhydrous tetrahydrofuran under an atmosphere of dry argon and it is stirred for 20 minutes at 23°C. It is cooled to -30°C, the solution of 70 mg (164 micromol) of the aldehyde, produced according to example 50b, in 490 microliters of tetrahydrofuran is instilled and stirred for 14 hours at -15°C. It is mixed with acetic acid and extracted several times with diethyl ether. The combined organic extracts are washed with dilute sodium bicarbonate solution, dried on magnesium sulfate and the residue obtained after removal of the solvent is purified by chromatography on 5 analytic thin-layer slabs. A mixture of n-hexane and ethyl acetate is used as mobile solvent, diethyl ether is used as eluant. 41 mg (91 micromol, 55%) of the title compound is isolated as colorless oil.

IR (Film): 3030, 3000, 2970, 2930, 2870, 1735, 1690, 1665, 1625, 1450, 1435, 1170, 1040, 980, 760 and 700 cm'1.

Example 50b: 7—[(IR,2S,3RS,5S)-2-Formyl-3-phenyl-5-fluoro-cyclopentyl]5(E/Z)-heptenoic acid methyl ester: The solution of 63 microliters of dimethyl sulfoxide in 280 microliters of dichloromethane is instilled in the solution, introduced under an atmosphere of dry argon at -60°C, of 34 microliters of freshly distilled oxalyl chloride in 690 microliters of anhydrous dichloromethane, it is allowed to react for 15 minutes and then mixed with the solution of 114 mg (341 micromol) of the alcohol, produced according to example 34a, in 690 microliters of dichloromethane. It is allowed to react for 4 hours, mixed with 107 microliters of triethylamine, poured in ice water and extracted several times with dichloromethane. The combined organic extracts are dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is further reacted without purification.

Example 51: 7-[(1R,2S,3RS,5S)-2-[(3R or 3S,4S)-3-Hydroxy-4-methyl-non1(E)-en-6-inyl]-3-phenyl-5-fluoro-cyclopentyl]-5(E)-heptenoic acid (A) and 7-[(IR,2S,3RS,5S)-2-[(3S or 3R,4S)-3-hydroxy-4methyl-non-1(E)-en-6-inyl]-3-phenyl-5-fluoro-cyclopentyl]-5(E)heptenoic acid methyl ester (B): mg (33 micromol) of compound B produced according to example 50 is reacted analogously to example 2 and, after working up and purification, 5 mg (11 micromol, 33%) of a more nonpolar component, to which the structure of title compound A is assigned, as well as 5.3 mg (12 micromol, 36%) of a more polar component, to which the structure of title compound B is assigned, are each isolated as colorless oil.

IR (Film) of A: 3600-2400, 3060, 3030, 2970, 2930, 2850, 1710, 1600, 1495, 1455, 1435, 1240, 1130, 970, 760 and 700 cm-1.

IR (Film) of B: 3600-2400, 3060, 3030, 2970, 2930, 1710, 1600, 1495, 1455, 1435, 1385, 1240, 1070, 1030, 1015, 970, 760 and 700 cm-1.

Example 52: - [ (IR, 2S, 3RS, 5S) -2 - [ (3 RS, 4 S) - 3-Hydroxy-4-methy1-non-1(E)en-6-inyl]-3-pheny1-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (46 micromol) of compound A produced according to example 50 is reacted analogously to example 2 and, after working up and purification, 17 mg (39 micromol, 84%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3080, 3060, 3030, 3000, 2970, 2930, 2870, 1710, 1600, 1495, 1455, 1435, 1405, 1345, 1320, 1240, 1035, 1010, 970, 760 and 700 cm'1.

Example 53: 7-[(IR,2S,3RS,5S)-2-[3(RS)-Hydroxy-oct-1(E)-enyl]-3-phenyl5-fluoro-cyclo-pentyl]-5(E)-heptenoic acid methyl ester (A) and 7-((IR,2S,3RS,5S)-2-[3(RS)-hydroxy-oct-1(E)-enyl]-3-phenyl-5fluoro-cyclo-pentyl]-5(Z)-heptenoic acid methyl ester (B): mg (142 micromol) of the compound produced according to example 53a is reacted analogously to example 15 and, after working up and purification, 47 mg (109 micromol, 77%) of title compound A as well as 12 mg (28 micromol, 20%) of title compound B are each isolated as colorless oil.

IR (Film): 3600-3200, 3030, 3000, 2950, 2930, 2850, 1735, 1600, 1450, 1435, 1245, 1170, 1070, 1030, 970, 755 and 700 cm1.

Example 53a: 7-((IR,2S,3RS,5S)-2-(3-Oxo-oct-l(E)-enyl]-3-phenyl-5-fluoro cyclopentyl)-5(E/Z)-heptenoic acid methyl ester: mg (168 micromol) of the compound produced according to example 50b is reacted analogously to example 50a with use of dimethyl-(2-oxo-heptyl)-phosphonate and, after working up and purification, 61 mg (142 micromol, 77%) of the title compound is isolated as colorless oil.

IR (Film): 3030, 2950, 2930, 2850, 1730, 1690, 1670, 1625, 1450, 1430, 1165, 1070, 980, 760 and 700 cm1.

Example 54: 7-[(IR,2S,3RS,5S)-2-[(3S or 3R)-3-Hydroxy-oct-l(E)-enyl]-3phenyl-5-fluoro-cyclopentyl]-5(E)-heptenoic acid (A) and 7((lR,2S,3RS,5S)-2-[(3R or 3S)-3-hydroxy-oct-l(E)-enyl]-3-phenyl5-fluoro-cyclopentyl]-5(E)-heptenoic acid (B): mg (27 micromol) of compound A produced according to example 53 is reacted analogously to example 2 and, after working up and purification, 5.3 mg (13 micromol, 47%) of a more nonpolar component, to which the structure of title compound A is assigned, as well as 4.9 mg (12 micromol, 44%) of a more polar component, to which the structure of title compound B is assigned, are each isolated as colorless oil.

IR (Film) of A: 3600-2400, 3080, 3060, 3030, 2950, 2930, 2860, 1690, 1600, 1495, 1455, 1305, 1260, 1035, 965, 755 and 700 cm IR (Film) of B: 3600-2400, 3080, 3060, 3030, 2950, 2930, 2860, 1700, 1600, 1495, 1455, 1340, 1325, 1260, 1135, 1070, 1015, 965, 755 and 700 cm'1.

Example 55: 7-[(IR,2S,3RS,5S)-2-(3(RS)-Hydroxy-oct-1(E)-enyl]-3-phenyl5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (77 micromol) of compound B produced according to example 53 is reacted analogously to example 2 and, after working up and purification, 17 mg (41 micromol, 53%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3080, 3060, 3030, 3000, 2950, 2930, 2860, 1710, 1600, 1495, 1465, 1405, 1345, 1240, 1035, 970, 760 and 700 cm1.

Example 56: 7-[(IS,2R,3RS,5R)-2-[(3RS,4S)-3-Hydroxy-4-methyl-non-l(E)en-6-inyl]-3-phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 183 mg (404 micromol) of the compound produced according to example 56a is reacted analogously to example 15 and, after working up and purification, 184 mg (404 micromol, 100%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3030, 2960, 2920, 2870, 1735, 1450, 1435, 1245, 1170, 1145, 1025, 970, 760 and 700 cm'1.

Example 56a: 7-[(1S,2R,3RS,5R)-2-[3-Oxo-4S-methyl-non-l(E)-en-6-inyl]-3phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 274 mg (561 micromol) of the compound produced according to example 56b is reacted analogously to example 50a and, after working up and purification, 183 mg (404 micromol, 72%) of the title compound is isolated as colorless oil.

IR (Film): 3060, 3030, 3000, 2970, 2930, 2870, 1735, 1690, 1670, 1625, 1450, 1430, 1370, 1170, 1040, 970, 760 and 700 cm'1.

Example 56b: 7-[(IS,2R,3RS,5R)-2-Formyl-3-phenyl-5-fluoro-cyclopentyl]5(Z)-heptenoic acid methyl ester: 500 mg (1.5 mmol) of the compound produced according to example 41a is reacted analogously to example 50b and, after working up, 500 mg (1.5 mmol, 100%) of the title compound is isolated as colorless oil, which is further reacted without purification.

Example 57: 7-C(IS ,2R,3RS,5R)-2-((3RS,4S)-3-Hydroxy-4-methyl-non-l(E)en-6-inyl]-3-phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: 184 mg (404 micromol) of the compound produced according to example 56 is saponified analogously to example 2 and, after working up and purification, 132 mg (300 micromol, 74%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2970, 2950, 1710, 1600, 1455, 1240, 970, 760 and 700 cm1.

Example 58: 7-((IS,2R,3RS,5R)-2-(3(RS)-Hydroxy-oct-1(E)-enyl]-3-phenyl5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 298 mg (695 micromol) of the compound produced according to example 58a is reacted analogously to example 15 and, after working up and purification, 260 mg (603 micromol, 87%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3060, 3030, 3000, 2950, 2930, 2850, 1735, 1600, 1450, 1435, 1245, 1170, 1070, 1030, 970, 760 and 700 Example 58a: 7-[(IS,2R,3RS,5R)-2-[3-Oxo-oct-1(E)-enyl]-3-phenyl-5-fluorocyclopentyl ]-5(Z)-heptenoic acid methyl ester: 270 mg (748 micromol) of the compound produced according to example 56b is reacted analogously to example 56a with use of dimethyl-(2-oxo-heptyl)-phosphonate and, after working up and purification, 298 mg (695 micromol, 93%) of the title compound is isolated as colorless oil.

IR (Film): 3030, 2950, 2920, 2850, 1730, 1690, 1670, 1625, 1450, 1430, 1240, 1165, 980, 760 and 700 cm1.

Example 59: 7-( (IS,2R, 3RS,5R)-2-[3(RS)-Hydroxy-oct-1(E)-enyl]-3-phenyl5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: 260 mg (604 micromol) of the compound produced according to example 58 is saponified analogously to example 2 and, after working up and purification, 235 mg (564 micromol, 93%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 2960, 2920, 2850, 1710, 1600, 1450, 1270, 970, 760 and 700 cm1.

Example 60: 7-((IS,2R,3RS,5R)-2-((3RS,4RS)-3-Hydroxy-4-phenyl-pent-l(E)enyl]-3-phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 172 mg (372 micromol) of the compound produced according to example 60a is reacted analogously to example 15 and, after working up and purification, 170 mg (366 micromol, 98%) of the title compound is Isolated as colorless oil.

IR (Film): 3600-3200, 3060, 3030, 2960, 2940, 1730, 1600, 1495, 1450, 1240, 1020, 970, 760 and 700 cm1.

Example 60a: 7-((IS,2R,3RS,5R)-2-(3-Oxo-4RS-phenyl-pent-l(E)-enyl]-3phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 274 mg (561 micromol) of the compound produced according to example 56b is reacted analogously to example 56a with use of dimethyl-(2-oxo-3-phenyl-butyl)-phosphonate and, after working up and purification, 172 mg (372 micromol, 66%) of the title compound is isolated as colorless oil.

IR (Film): 3060, 3030, 2950, 2930, 2850, 1735, 1690, 1670, 1625, 1490, 1450, 1430, 1370, 1245, 1165, 1070, 1030, 980, 760 and 700 cm1.

Example 61: 7-[(IS,2R,3RS,5R)-2-[(3R or 3S,4RS)-3-Hydroxy-4-phenyl-pent1(E)-enyl]-3-phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid (A) and 7-[(IS,2R,3RS,5R)-2-[(3S or 3R,4RS)-3-hydroxy-4-phenyl-pent1(E)-enyl]-3-phenyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester (B): 170 mg (366 micromol) of the compound produced according to example 60 is saponified analogously to example 2 and, after working up and purification, 24 mg (53 micromol, 15%) of a nonpolar component, to which the structure of title compound A is assigned, as well as 45 mg (100 micromol, 27%) of a polar component, to which the structure of title compound B is assigned, are each isolated as colorless oil.

IR (Film) of A; 3600-2400, 3060, 3030, 2960, 2940, 1710, 1600, 1500, 1450, 1240, 1020, 970, 760 and 700 cm'1.

IR (Film) of B: 3600-2400, 3060, 3030, 2960, 2950, 1710, 1600, 1495, 1455, 1240, 1030, 1010, 980, 760 and 700 cm'1.

Example 62: 7-[(IS ,2R,3R,5R)-2-[(E/Z)-Diphenylmethoxyiminomethyl]-3,5dihydroxy-cyclopentyl]-5(Z)-heptenoic acid: 108 mg (207 micromol) of the compound produced according to example 62a is mixed with 1.2 ml of a mixture of acetic acid, water and tetrahydrofuran (65:35:10) and stirred for 15 hours at 23°C. It is concentrated by evaporation, residual acetic acid is removed by repeated azeotropic distillation with toluene and the residue is purified by chromatography on about ml of fine silica gel. 75 mg (171 micromol, 83%) of the title compound is isolated as colorless oil.

IR (Film): 3700-2400, 3090, 3060, 3030, 3010, 2940, 1710, 1490, 1450, 1245, 1035, 1020, 940, 745 and 700 cm'1.

Example 62a: 7-((IS,2R,3R,5R)-2-[(E/Z)-Diphenylmethoxyiminomethyl]-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid: 1.18 g (1.84 mmol) of the compound produced according to example 62b is saponified analogously to example 2 and, after working up and purification, 943 mg (1.81 mmol, 98%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3090, 3060, 3030, 3010, 2940, 2870, 1740, 1710, 1600, 1495, 1450, 1240, 1130, 1115, 1035, 1020, 935, 920, 870, 815, 745 and 705 cm'1.

Example 62b: 7-((IS,2R,3R,5R)-2-((E/Z)-Diphenylmethoxyiminomethyl]-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)heptenoic acid methyl ester: The colorless solution of 1.0 g (2.18 mmol) of the compound, produced according to example 62c, in 16 ml of anhydrous ethanol is mixed with 0.4 ml of anhydrous pyridine, 588 mg of diphenylmethoxyamine, and heated for 3.5 hours under an atmosphere of dry argon to 50°C. It is concentrated by evaporation, the residue is taken up in dichloromethane, it is washed with water and saturated sodium chloride solution and the residue obtained after drying on magnesium sulfate, filtration and concentration by evaporation is purified by chromatography on about 50 ml of silica gel with an n-hexane/ethyl acetate mixture. 1.18 g (1.84 mmol, 85%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3030, 3010, 2950, 2870, 1740, 1715, 1605, 1585, 1495, 1450, 1360, 1275, 1115, 1025, 940, 920, 870, 815, 745, 715 and 705 cm'1.

Example 62c: 7-((IS,2R,3R,5R)-2-Formyl-3-(tetrahydropyran-2-yloxy)-5benzoyloxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: g (19.5 mmol) of the compound produced according to example 62d is reacted analogously to example 50b and, after working up, 9 g (19.5 mmol, 100%) of the title compound is isolated, which is further reacted without purification.

Example 62d: 7-((IS,2R,3R,5R)-2-Hydroxymethyl-3-(tetrahydropyran-2yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 22.4 g (32 mmol) of the compound produced according to example 62e is reacted analogously to example lg and, after working up and purification, 13.7 g (29.7 mmol, 93%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 2950, 2870, 1740, 1720, 1605, 1585, 1450, 1370, 1315, 1275, 1245, 1115, 1075, 1030, 870, 810 and 715 cm’*.

Example 62e: 7-((IS,2R,3R,5R)-2-(tert-Butyldiphenylsilyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z) heptenoic acid methyl ester: 19.8 g (33.4 mmol) of the compound produced according to example 62f is reacted analogously to example lh and, after working up and purification, 22.4 g (32 mmol, 96%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3050, 3010, 2940, 2860, 1740, 1720, 1605, 1590, 1455, 1430, 1275, 1115, 1070, 1025, 825, 740 and 710 cm-1.

Example 62f: 7-((IS,2R,3R,5R)-2-(tert-Butyldiphenylsilyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: .8 g (44.4 mmol) of the compound produced according to example 62g is reacted analogously to example li and, after working up and purification, 19.9 g (33.4 mmol, 75%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 3050, 3010, 2940, 2860, 1740, 1590, 1430, 1200, 1110, 1075, 1020, 1000, 870, 825, 740 and 705 Example 62q: 7-((IS,2R,3R,5R)-2-(tert-Butyldiphenylsilyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid: 23.8 g (47.9 mmol) of the compound produced according to example 62h is reacted analogously to example lj and, after working up and purification, 25.8 g (44.4 mmol, 93%) of the title compound is isolated as colorless oil.

IR (Film): 3700-2400, 3070, 3050, 2940, 2860, 1710, 1590, 1430, 1390, 1260, 1200, 1110, 1075, 1045, 1020, 995, 880, 825, 740 and 705 cm1.

Example 62h: (IR, 3 RS, 5S, 6R, 7R) -3-Hydroxy-6-(tertbutyldiphenylsilyloxymethyl)-7-(tetrahydropyran-2-yloxy)-2oxabicyclo[3.3.0]octane: 23.8 g (48.1 mmol) of the compound produced according to example 62i is reacted analogously to example lk and, after working up and purification, 23.8 g (47.9 mmol, 99%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 3050, 2940, 2860, 1740, 1590, 1430, 1390, 1375, 1355, 1240, 1110, 1075, 1020, 870, 820, 740 and 705 cm1.

Example 62i: (IR,5S,6R,7R)-3-0ΧΟ-6-(tert-butyldiphenylsilyloxymethyl)-7(tetrahydropyran-2-yloxy)-2-oxabicyclo[3.3.0]octane: The solution of 20.7 g (50.4 mmol) of the compound, produced according to example 62j, in 400 ml of anhydrous dichloromethane is mixed at 0°C with 6.83 ml of dihydropyran, 135 mg of ptoluenesulfonic acid and it is stirred for 1.5 hours under an atmosphere of dry argon. It is diluted with dichloromethane, washed with a saturated sodium bicarbonate solution, a saturated sodium chloride solution, and dried on magnesium sulfate. The residue obtained after filtration and removal of the solvent is purified by chromatography on about 300 ml of fine silica gel. 23.8 g (48.1 mmol, 95%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3050, 2940, 2860, 1780, 1740, 1590, 1470, 1430, 1390, 1375, 1355, 1245, 1170, 1110, 1075, 1035, 870, 825, 745 and 705 cm'1.

Example 62i: (IR, 5S,6R,7R)-3-Oxo-6-(tert-butyldiphenylsilyloxymethyl)-7hydroxy-2-oxabicyclo[3.3.0]octane: The solution of 1.5 g (2.66 mmol) of the compound, produced according to example 62k, in 74 ml of anhydrous dimethylformamide is mixed with 3.32 g of potassium nitrite and heated under an atmosphere of dry argon for 16 hours to 85°C. It is concentrated by evaporation, diluted with water and extracted several times with dichloromethane. The combined organic extracts are washed with saturated sodium chloride solution, dried on magnesium sulfate and the residue obtained after removal of the solvent is purified by chromatography on about 100 ml of fine silica gel. 700 mg (1.70 mmol, 64%) of the title compound is isolated as colorless oil.

Example 62k: (IR,5S,6R,7S)-3-Oxo-6-(tert-butyldiphenylsilyloxymethyl)-7toluenesulfonyloxy-2-oxabicyclo[3.3.0]octane: 2.37 g (5.77 mmol) of (lR,5S,6R,7S)-3-oxo-6-(tertbutyldiphenylsilyloxymethyl)-7-hydroxy-2-oxabicyclo[3.3.OJoctane is reacted analogously to example lm and, after working up and purification, 2.9 g (5.17 mmol, 90%) of the title compound is isolated as colorless oil.

IR (CHC13): 3070, 3050, 3030, 3000, 2960, 2930, 2860, 1770, 1600, 1425, 1365, 1190, 1175, 1110, 1040, 980, 960, 895, 875, 820 and 700 cm1.

Example 63: 7-((IS,2R,3R,5R)-2-((E/Z)-Phenylureidoiminomethyl]-3,5dihydroxy-cyclopentyl]-5(Z)-heptenoic acid: 99.5 mg (210 micromol) of the compound produced according to example 63a is reacted analogously to example 62 and, after working up and purification, 77 mg (198 micromol, 94%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3380, 3260, 3010, 2950, 2860, 1710, 1670, 1600, 1590, 1500, 1450, 1240, 750 and 690 cm'1.

Example 63a: 7-((IS,2R,3R,5R)-2-((E/Z)-Phenylureidoiminomethyl]-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid: 345 mg (583 micromol) of the compound produced according to example 63b is saponified analogously to example 2 and, after working up and purification, 248 mg (418 micromol, 72%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3380, 3220, 3100, 3010, 2940, 2870, 1710, 1690, 1590, 1535, 1450, 1320, 1230, 1115, 1030, 1020, 985, 870, 810, 755 and 690 cm1.

Example 63b: 7-[(IS,2R,3R,5R)-2-[(E/Z)-Phenylureidoiminomethyl)-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)heptenoic acid methyl ester: 600 mg (1.31 mmol) of the compound produced according to example 62c is reacted analogously to example 62b with use of 4phenylsemicarbazide and, after working up and purification, 775 mg (1.31 mmol, 100%) of the title compound is isolated as colorless oil.

IR (Film): 3380, 3200, 3100, 2950, 2870, 1715, 1690, 1595, 1535, 1450, 1275, 1225, 1115, 1035, 1025, 980, 870, 815, 760, 715 and 695 cm'*.

Example 64: 7-[(IS,2R,3R,5R)-2-(2-Fluorobenzyloxymethyl)-3,5-dihydroxycyclopentyl]-5(Z)-heptenoic acid: 50.6 mg (112 micromol) of the compound produced according to example 64a is reacted analogously to example 62 and, after working up and purification, 34.9 mg (95 micromol, 85%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2930, 2870, 1710, 1620, 1595, 1495, 1455, 1230, 1110, 1085, 1020, 995 and 760 cm-1.

Example 64a: 7-[(lS,2R,3R,5R)-2-(2-Fluorobenzyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid: 127 mg (224 micromol) of the compound produced according to example 64b is saponified analogously to example 2 and, after working up and purification, 69 mg (153 micromol, 69%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2930, 2870, 1710, 1620, 1590, 1495, 1455, 1235, 1115, 1085, 1020, 995, 870, 810 and 760 cm1.

Example 64b: 7-[(lS,2R,3R,5R)-2-(2-Fluorobenzyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)heptenoic acid methyl ester: The solution of 500 mg (1.09 mmol) of the compound, produced according to example 62d, in 8.5 ml of toluene is mixed with 3.5 ml of a 25% aqueous sodium hydroxide solution, 50 mg of tetrabutylammonium hydrogen sulfate, 1.03 g of 2-fluorobenzyl bromide and the 2-phase system is stirred for 5 days at 23°C. It is diluted with water, adjusted to a pH of 5 by adding saturated citric acid and extracted several times with diethyl ether. The combined organic extracts are dried on magnesium sulfate and the residue obtained after removal of the solvent is purified by chromatography on about 100 ml of silica gel with a mixture of nIE 912654 hexane and ethyl acetate. 137 mg (241 micromol, 22%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3010, 2950, 2870, 1740, 1720, 1620, 1605, 1590, 1495, 1455, 1365, 1315, 1275, 1115, 1025, 870, 815, 760 and 715 cm'1.

Example 65: 7-((IS,2R,3R,5R)-2-Benzyloxymethyl-3,5-dihydroxycyclopenty1]-5(Z)-heptenoic acid: 57.5 mg (133 micromol) of the compound produced according to example 65a is reacted analogously to example 62 and, after working up and purification, 40 mg (115 micromol, 86%) of the title compound is isolated as colorless oil.

IR (Film): 3700-2400, 3070, 3030, 3010, 2930, 2870, 1710, 1450, 1240, 1100, 1070, 740 and 700 cm-1.

Example 65a: 7-[(IS,2R,3R,5R)-2-Benzyloxymethyl-3-(tetrahydropyran-2yloxy)-5-hydroxycyclopentyl]-5(Z)-heptenoic acid: 126 mg (229 micromol) of the compound produced according to example 65b is saponified analogously to example 2 and, after working up and purification, 77 mg (178 micromol, 78%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3010, 2940, 2870, 1710, 1455, 1365, 1260, 1240, 1200, 1115, 1075, 1020, 995, 870, 810, 740 and 700 cm1.

Example 65b: 7-[(IS,2R,3R,5R)-2-Benzyloxymethyl-3-(tetrahydropyran-2yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 500 mg (1.09 micromol) of the compound produced according to example 62d is reacted analogously to example 64b with use of benzyl bromide and, after working up and purification, 134 mg (243 micromol, 22%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3030, 3010, 2940, 2860, 1735, 1720, 1605, 1585, 1450, 1365, 1275, 1115, 1075, 1025, 870, 815, 740, 715 and 700 cm-1.

Example 66: - [ (IS, 2R, 3R, 5R) -2 - (3-Methylbenzyloxymethyl) -3,5-dihydroxycyclopentyl)-5(Z)-heptenoic acid: 36.3 mg (81 micromol) of the compound produced according to example 66a is reacted analogously to example 62 and, after working up and purification, 23 mg (63 micromol, 78%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2930, 2870, 1710, 1610, 1410, 1245, 1155, 1085, 885, 785, 745 and 700 cm'1.

Example 66a: 7-[(IS,2R,3R,5R)-2-(3-Methylbenzyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid: 68.7 mg (122 micromol) of the compound produced according to example 66b is saponified analogously to example 2 and, after working up and purification, 41.4 mg (93 micromol, 76%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2940, 2870, 1710, 1610, 1455, 1440, 1355, 1200, 1160, 1115, 1075, 1020, 995, 870, 780, 740 and 695 cm"1.

Example 66b: 7-[(IS,2R,3R,5R)-2-(3-Methylbenzyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z) heptenoic acid methyl ester: 1.3 g (2.82 mmol) of the compound produced according to example 62d is reacted analogously to example 64b with use of 3methylbenzyl bromide and, after working up and purification, 424 mg (751 micromol, 27%) of the title compound is isolated as colorless oil.

IR (Film): 3060, 3010, 2940, 2860, 1740, 1720, 1605, 1585, 1450, 1360, 1315, 1275, 1115, 1075, 1025, 780 and 715 cm1.

Example 67: 7-[(IS,2R,3R,5R)-2-(4-Fluorobenzyloxymethyl)-3,5-dihydroxycyclopentyl]-5(Z)-heptenoic acid: 66.8 mg (148 micromol) of the compound produced according to example 67a is reacted analogously to example 62 and, after working up and purification, 39.2 mg (107 micromol, 72%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2940, 2870, 1710, 1605, 1510, 1225, 1090, 855 and 825 cm'1.

Example 67a: 7-[(IS,2R,3R,5R)-2-(4-Fluorobenzyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid: 136 mg (238 micromol) of the compound produced according to example 67b is saponified analogously to example 2 and, after working up and purification, 87.5 mg (194 micromol, 81%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2940, 2870, 1710, 1605, 1510, 1225, 1115, 1075, 1020, 995, 855 and 825 cm1.

Example 67b: 7-[(IS,2R,3R,5R)-2-(4-Fluorobenzyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)heptenoic acid methyl ester: 500 mg (1.09 mmol) of the compound produced according to example 62d is reacted analogously to example 64b with use of 4 fluorobenzyl bromide and, after working up and purification, 144 mg (253 micromol, 23%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3010, 2950, 2870, 1740, 1715, 1605, 1510 1450, 1365, 1315, 1275, 1225, 1115, 1025, 1000, 825 and 715 cm Example 68: 7-[(IS,2R,3S,5S)-2-[(E/Z)-Diphenylmethoxyiminomethyl]-3hydroxy-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (134 micromol) of compound A produced according to example 68 is reacted analogously to example 62 and, after working up and purification, 46 mg (101 micromol, 76%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3060, 3030, 3010, 2940, 2870, 1730, 1600, 1495, 1455, 1240, 1020, 935, 745 and 700 cm'1 .

Example 68a: 7-[(IS,2R,3S,5S)-2-[(E/Z)-Diphenylmethoxyiminomethyl]-3(tetrahydropyran-2-yloxy)-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester (A) and 7-[(5R,4S)-5-[(E/Z)diphenylmethoxyiminomethyl]-4-(tetrahydropyran-2-yloxy)cyclopent-l-enyl]-5(Z)-heptenoic acid methyl ester: 252 mg (471 micromol) of the compound produced according to example 68b is reacted analogously to example 1 and, after working up and purification, 72 mg (134 micromol, 28%) of title compound A as well as 58 mg (112 micromol, 24%) of title compound B are each isolated as colorless oil.

IR (Film): 3600-3200, 3060, 3030, 3010, 2940, 2870, 1730, 1600, 1455, 1245, 1020, 935, 870, 820, 745 and 700 cm1.

Example 68b: 7-[(IS,2R,3S,5R)-2-[(E/Z)-Diphenylmethoxyiminomethyl]-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: The solution of 257 mg (493 micromol) of the compound, produced according to example 68c, in 10 ml of dichloromethane is mixed with the ethereal solution of diazomethane and, after completion of the reaction, it is concentrated by evaporation. 262 mg (489 micromol, 99%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 3030, 3010, 2950, 2870, 1740, 1455, 1440, 1350, 1200, 1130, 1080, 1025, 975, 910, 870, 815, 745 and 705 cm-1.

Example 68c: 7-[(IS,2R,3S,5R)-2-[(E/Z)-Diphenylmethoxyiminomethyl J-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid: 569 mg (889 micromol) of the compound produced according to example 68d is saponified analogously to example 2 and, after working up and purification, 399 mg (765 micromol, 86%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3070, 3030, 3010, 2940, 270, 1730, 1710, 1605, 1495, 1445, 1345, 1245, 1205, 1185, 1130, 1080, 1020, 975, 920, 870, 810, 745 and 705 cm1.

Example 68d: 7-((1S,2R,3S,5R)-2-((E/Z)-Diphenylmethoxyiminomethyl]-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)heptenoic acid methyl ester: 300 mg (654 micromol) of the compound produced according to example 68e is reacted analogously to example 62b and, after working up and purification, 268 mg (453 micromol, 69%) of the title compound is isolated as colorless oil.

IR (Film): 3380, 3210, 3100, 3010, 2950, 2870, 1735, 1715, 1690, 1600, 1535, 1450, 1360, 1320, 1275, 1115, 1070, 1030, 970, 870, 815, 760, 715 and 695 cm-1.

Example 68e: 7-((IS,2R,3S,5R)-2-Formyl-3-(tetrahydropyran-2-yloxy)-5benzoyloxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 1.2 g (2.61 mmol) of the compound produced according to example 68f is reacted analogously to example 50b and, after working up, 1.2 g (2.61 mmol, 100%) of the title compound is isolated, which is further reacted without purification.

Example 68f: 7-[(IS,2R,3S,5R)-2-Hydroxymethyl-3-(tetrahydropyran-2yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 2.16 g (3.09 mmol) of the compound produced according to example 68g is reacted analogously to example lg and, after working up and purification, 1.2 g (2.61 mmol, 85%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3060, 3000, 2940, 2860, 1735, 1710, 1600, 1585, 1450, 1355, 1310, 1270, 1110, 1070, 1025, 865, 810 and 710 cm-1.

Example 68σ: 7-((IS,2R,3S,5R)-2-(tert-Butyldiphenylsilyloxyraethyl)-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z)heptenoic acid methyl ester: 59.4 g (99.9 mmol) of the compound 7-((lS,2R,3S,5R)-2-(tert butyldiphenyIsilyloxymethyl)-3-(tetrahydropyran-2-yloxy) -5hydroxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester produced analogously to example 29b is reacted analogously to example lh and, after working up and purification, 62.5 g (89.4 mmol, 90%) of the title compound is isolated as colorless oil.

IR (Film): 3070, 3050, 3010, 2950, 2860, 1740, 1715, 1600, 1585, 1450, 1425, 1275, 1110, 1025, 970, 870, 825, 790, 710, 690 610 and 500 cm'1.

Example 69: 7-((1S,2R, 3S,5S)-2-((E/Z)-Diphenylmethoxyiminomethyl]-3hydroxy-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (101 micromol) of the compound produced according to example 68 is saponified analogously to example 2 and, after working up and purification, 29 mg (66 micromol, 65%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3010, 2940, 2870, 1710, 1600, 1495, 1455, 1240, 1020, 935, 745 and 700 cm-1.

Example 70: 7-((IS,2R,3S,5R)-2-((E/Z)-Diphenylmethoxyiminomethyl]-3,5dihydroxy-cyclopentyl]-5(Z)-heptenoic acid: 128 mg (244 micromol) of the compound produced according to example 68c is reacted analogously to example 62 and, after working up and purification, 84 mg (192 micromol, 78%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3060, 3030, 3010, 2940, 1710, 1605, 1495, 1450, 1375, 1245, 1045, 1020, 935, 920, 745 and 700 cm-1.

Example 71: 7-((IS,2R,3R,5S)-2-((E/Z)-Phenylureidoiminomethyl]-3,5dihydroxy-cyclopentyl]-5(Z)-heptenoic acid: 137.6 mg (271 micromol) of the compound produced according to example 71a is saponified analogously to example 2 and, after working up and purification, 93.8 mg (241 micromol, 89%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3370, 3010, 2940, 1730-1680, 1600, 1540, 1450, 1375, 1240, 1115, 1045, 760 and 695 cm-1.

Example 71a: 7-[(IS,2R,3R,5S)-2-((E/Z)-Phenylureidoiminomethyl]-3hydroxy-5-benzoyloxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 248 mg (419 micromol) of the compound produced according to example 71b is reacted analogously to example 62 and, after working up and purification, 149 mg (294 micromol, 70%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3380, 3070, 3010, 2950, 2870, 17401680, 1600, 1540, 1450, 1360, 1315, 1275, 1175, 1115, 1070, 1030 940, 760, 715 and 695 cm-1.

Example 71b: 7-[(IS,2R,3R,5S)-2-[(E/Z)-Phenylureidoiminomethy1]-3(tetrahydropyran-2-yloxy)-5-benzoyloxy-cyclopentyl]-5(Z) heptenoic acid methyl ester: 300 mg (654 micromol) of the compound produced according to example 68e is reacted analogously to example 62b and, after working up and purification, 268 mg (453 micromol, 69%) of the title compound is isolated as colorless oil.

IR (Film): 3380, 3210, 3100, 3010, 2950, 2860, 1735, 1715, 1690, 1595, 1530, 1450, 1315, 1275, 1115, 1025, 970, 870, 810, 755, 715 and 695 cm1.

Example 72: 7-[(IS,2R,3S,5S)-2-(3-Methylbenzyloxymethy1)-3-hydroxy-5fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 201 mg (435 micromol) of the compound produced according to example 72a is reacted analogously to example 62 and, after working up and purification, 89 mg (235 micromol, 54%) of the title compound is isolated as colorless oil. se IR (Film): 3600-3200, 3010, 2940, 2860, 1735, 1610, 1440, 1360, 1250, 1220, 1155, 1100, 1090, 780, 745 and 695 cm-1.

Example 72a: 7-[(IS,2R,3S,5S)-2-(3-Methylbenzyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester (A) and 7-[(5R,4S)-5-(3-methylbenzyloxymethyl)4-(tetrahydropyran—2—yloxy)-cyclopent-l-enyl]-5(Z)-heptenoic acid methyl ester (B): 800 mg (1.74 mmol) of the compound produced according to example 72b is reacted analogously to example 1 and, after working up and purification, 201 mg (436 micromol, 25%) of title compound A as well as 212 mg (480 micromol, 28%) of title compound B are each isolated as colorless oil.

IR (Film): 3600-3200, 3010, 2940, 2850, 1730, 1610, 1440, 1360, 1250, 1225, 1155, 1095, 870, 815, 780, 745 and 695 cm1.

Example 72b: 7-((IS,2R,3S,5R)-2-(3-Methylbenzyloxymethyl)-3(tetrahydropyran-2-yloxy)-5-hydroxy-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 1.23 g (2.75 mmol) of the compound produced according to example 68f is reacted analogously to example 64b and, after working up and purification, 1.18 g (2.56 mmol, 93%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3300, 3010, 2940, 2860, 1740, 1610, 1595, 1440, 1355, 1250, 1200, 1155, 1115, 1075, 1020, 975, 905, 870, 815, 780, 745 and 695 cm-1.

Example 73: 7—[(IS,2R,3S,5S)-2-(3-Methylbenzyloxymethyl)-3-hydroxy-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: .7 mg (81 micromol) of the compound produced according to example 72 is saponified analogously to example 2 and, after working up and purification, 19.8 mg (54 micromol, 67%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2930, 2860, 1710, 1610, 1590, 1455, 1440, 1360, 1240, 1155, 1100, 1085, 780, 745 and 695 cm-1.

Example 74: 7-[(1S,2R,5S)-2-(3-Methylbenzyloxymethyl)-5-fluorocyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (148 micromol) of the compound produced according to example 74a is reacted analogously to example 11 and, after working up and purification, 36.4 mg (106 micromol, 72%) of the title compound is isolated as colorless oil.

IR (Film): 3010, 2930, 2850, 1730, 1610, 1590, 1455, 1410, 1355, 1240, 1160, 1100, 1090, 780, 755 and 695 cm1. 100 Example 74a: 7-[(IS,2R,3S,5S>-2-(3-Methylbenzyloxymethyl)-3toluenesulfonyloxy-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (162 micromol) of the compound produced according to example 72 is reacted analogously to example lm and, after working up and purification, 76 mg (148 micromol, 92%) of the title compound is isolated as colorless oil.

IR (Film): 3050, 3010, 2950, 2920, 2860, 1735, 1600, 1435, 1360, 1190, 1175, 1095, 975, 945, 885, 815, 780, 745 and 665 Example 75: 7-[(IS,2R,5S)-2-(3-Methylbenzyloxymethyl)-5-fluorocyclopentyl ]-5(Z)-heptenoic acid: mg (106 micromol) of the compound produced according to example 74 is saponified analogously to example 2 and, after working up and purification, 8.6 mg (26 micromol, 25%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2920, 2850, 1705, 1610, 1590, 1455, 1410, 1355, 1240, 1155, 1105, 1085, 780, 755 and 695 cm-1. 1C1 Example 76: 7-[(IS,2R,3S,5R)-2-(3-Methylbenzyloxymethyl) -3,5-dihydroxycyclopentyl]-5(Z)-heptenoic acid methyl ester: 87.2 mg (189 micromol) of the compound produced according to example 72b is reacted analogously to example 62 and, after working up and purification, 63.4 mg (168 micromol, 89%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3100, 3010, 2950, 2930, 2860, 1735, 1610, 1440, 1360, 1245, 1160, 1100, 780, 745 and 695 cm-1.

Example 77: 7-[(IS,2R,3S,5R)-2-(3-Methylbenzyloxymethyl)-3,5-dihydroxycyclopenty1]-5(Z)-heptenoic acid: mg (141 micromol) of the compound produced according to example 76 is saponified analogously to example 2 and, after working up and purification, 40 mg (110 micromol, 79%) of the title compound is isolated as colorless oil.

IR (Film): 3600-2400, 3010, 2930, 2860, 1710, 1610, 1590, 1455, 1430, 1405, 1355, 1245, 1155, 1100, 780, 745 and 695 cm-1.

Example 78: 6-[(IR,2S,5R)-2-[3-(4-Fluorophenyl)-ureidomethyl]-5-fluorocyclopentyl ] -4 (Z) -hexenoic acid methyl ester: The solution of 80 mg (max. 136 micromol) of the amine, produced according to example 78a, in 1 ml of dichloromethane is mixed with 21 microliters of 4-fluorophenyl isocyanate and 102 stirred for 2.5 hours at 23°C. It is purified by chromatography on three analytic thin-layer slabs. A mixture of n-hexane and ethyl acetate is used as mobile solvent, ethyl acetate is used as eluant. 25 mg (66 micromol, 48%) of the title compound is isolated as colorless oil.

IR (Film): 3250-3450, 3050, 2950, 2850, 1730, 1640, 1595, 1555, 1515, 1490, 1430, 1325, 1235, 835, 735 and 705 cm-1.

Example 78a: 6-[(IR,2S,5R)-2-Aminomethyl-5-fluoro-cyclopentyl]-4(Z) hexenoic acid methyl ester: The solution of 747 mg (2.77 mmol) of the compound, produced according to example 78b, in 24 ml of tetrahydrofuran is mixed with 874 mg of triphenylphosphine and heated for 3.5 hours under an atmosphere of dry argon to 50°C. Then, it is mixed with 3 ml of water and refluxed for 1 hour. It is concentrated by evaporation, taken up with dichloromethane, dried on magnesium sulfate and, after filtration and removal of the solvent, 1.62 g (max. 2.77 mmol) of amine contaminated with triphenylphosphine and triphenylphosphinoxide is isolated, which is further reacted without purification. 103 Example 78b: 6-[(IR,2S,5R)-2-Azidomethyl-5-fluoro-cyclopentyl]-4(Z)hexenoic acid methyl ester: The solution of 934 mg (3.04 mmol) of the bromide, produced according to example 78c, in 67 ml of dimethylformamide is mixed with 839 mg of sodium azide and heated for 4 hours under an atmosphere of dry argon to 60°C. It is poured in ice water, extracted several times with diethyl ether, the organic phase is dried on magnesium sulfate and the residue obtained after filtration and removal of the solvent is purified by chromatography on about 200 ml of fine silica gel with use of a gradient system of n-hexane and ethyl acetate. 747 mg (2.77 mmol, 91%) of the title compound is isolated as colorless oil.

IR (Film): 2950, 2870, 2100, 1735, 1435, 1360, 1245 and 1160 cm'1.

Example 78c: 6-[(IR,2S,5R)-2-Bromomethyl-5-fluoro-cyclopentyl]-4(Z)hexenoic acid methyl ester: The solution of 743 mg (3.04 mmol) of the alcohol, produced according to example 78d, in 22 ml of acetonitrile is mixed with 2.05 ml of collidine, 5.05 g of tetrabromomethane, 4.0 g of triphenylphosphine and it is stirred for 17 hours at 23°C under an atmosphere of dry argon. It is concentrated by evaporation and the resulting residue is purified by chromatography on about 104 200 ml of fine silica gel with use of a gradient system of nhexane and ethyl acetate. 934 mg (3.04 mmol, 100%) of the title compound is isolated as colorless oil.

IR (Film): 2950, 2860, 1735, 1435, 1360, 1245, 1220, 1160 and 950 cm-1.

Example 78d: 6-((IR,2S,5R)-2-Hydroxymethyl-5-fluoro-cyclopentylJ-4(Z)hexenoic acid methyl ester (A) and 6-((5S)-5-hydroxy-cyclopent-l enyl]-4(Z)-hexenoic acid methyl ester (B): 3.69 g of the substance mixture produced according to example 78e is reacted analogously to example lg and, after working up and purification, 943 mg (4.20 mmol, 40%) of title compound B as a nonpolar component, as well as 758 mg (3.10 mmol 30%) of title compound A as a polar component are each isolated as colorless oil.

IR (Film) of A: 3200-3600, 3050, 2950, 2870, 1735, 1435, 1360, 1165, 1040, 945 and 875 cm 1 IR (Film) of B: 3200-3600, 3050, 2940, 2850, 1735, 1435, 1360, 1200, 1160 and 1025 cm l. 105 Example 78e: 6—[(IR,2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-fluorocyclopentyl ]-4(Z)-hexenoic acid methyl ester and 6-[(5S)-5-(tertbutyldiphenylsilyloxymethyl)-cyclopent-l-enyl]-4(Z)-hexenoic acid methyl ester: .0 g (10.4 mmol) of the compound produced according to example 78f is reacted analogously to example 1 and, after working up and purification, 3.81 g of a mixture of both title compounds is isolated as colorless oil.

Example 78f: 6-[(IR,2S,5S)-2-tert-Butyldiphenylsilyloxymethyl-5-hydroxycyclopentyl]-4(Z)-hexenoic acid methyl ester: 62.6 g (max. 58.3 mmol) of the compound produced according to example 78g is reacted analogously to example 68b and, after working up and purification, 26.8 g (55.7 mmol, 96%) of the title compound is isolated as colorless oil.

IR (Film): 3600-3200, 3070, 3040, 2950, 2930, 2850, 1735, 1585, 1460, 1425, 1240, 1160, 1110, 1005, 820, 740 and 700 cm-1.

Example 78q: 6-((IR,2S,5S)-2-tert-Butyldiphenylsilyloxymethyl-5-hydroxycyclopentyl]-4(Z)-hexenoic acid: 23.1 g (58.3 mmol) of the compound produced according to example lk is reacted analogously to example lj with use of carboxypropyltriphenylphosphonium bromide and, after working up, 106 62.6 g of the title compound is isolated as crude product, which is further reacted without purification.

Example 79: 6-[(IR,2S,5R)-2-[3-(4-Fluorophenyl)-ureidomethyl]-5-fluorocyclopentyl ]-4(Z)-hexenoic acid: mg (66 micromol) of the compound produced according to example 78 is saponified analogously to example 2 and, after working up and purification, 21 mg (57 micromol, 87%) of the title compound is isolated as colorless oil.

^-NMR (CD3OD) : S = 1· 4-2.4 (m, 12H) , 3.12-3.35 (m, 2H) , 4.74(m,lH), 5.4-5.55(m,2H), 6.92-7.04(m,2H), 28-7.38(m,2H).

Example 80: 6-[(1R,2S,5R)-2-[3-(4-Phenylphenyl)-ureidomethyl]-5-fluorocyclopentyl]-4(Z)-hexenoic acid methyl ester: mg (max. 136 micromol) of the compound produced according to example 78a is reacted analogously to example 78 with use of 4-phenylphenyl isocyanate and, after working up and purification, 25 mg (57 micromol, 42%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3450, 3030, 2950, 2860, 1735, 1645, 1590, 1550, 1485, 1310, 1265, 1230, 835, 765, 735 and 700 cm’1. 107 Example 81: 6-[(IR,2S,5R)-2-(3-(4-Phenylphenyl)-ureidomethyl]-5-fluorocyclopentyl]-4(Z)-hexenoic acid: mg (57 micromol) of the compound produced according to example 80 is saponified analogously to example 2 and, after working up and purification, 14 mg (33 micromol, 58%) of the title compound is isolated as colorless oil.

^-NMR (CD3OD) : J = 1.5-2.4 (m, 12H) , 3.17-3.35 (m, 2H) , 4.78(m,lH), 5.4-5.55(m,2H), 7.22-7.6(m,9H).

Example 82: 6-[(IR,2S,5R)-2-[3-(4-Methylphenyl)-ureidomethyl]-5-fluorocyclopentyl] -4(Z)-hexenoic acid methyl ester: mg (max. 136 micromol) of the compound produced according to example 78a is reacted analogously to example 78 with use of 4-methylphenyl isocyanate and, after working up and purification, 28 mg (74 micromol, 55%) of the title compound is isolated as colorless oil.

IR (Film): 3250-3450, 3050, 2950, 2860, 1730, 1640, 1600, 1555, 1515, 1260, 815, 735 and 705 cm1.

Example 83: 6-[(IR,2S,5R)-2-(3-(4-Methylphenyl)-ureidomethyl]-5-fluorocyclopentyl] -4(Z)-hexenoic acid: mg (74 micromol) of the compound produced according to example 82 is saponified analogously to example 2 and, after 103 working up and purification, 14 mg (39 micromol, 52%) of the title compound is isolated as colorless oil.

^-NMR (CD3OD) : cT= 1.45-2.4(m, 15H) , 3.12-3.34 (m, 2H) , 4.76(m,lH), 5.4-5.55(m,2H), 7.06(d,2H), 7.21(d,2H).

Example 84: 6—((IR,2S,5R)-2-(3-(3-Chlorophenyl)-ureidomethyl]-5-fluorocyclopentyl] -4 (Z) -hexenoic acid methyl ester: mg (max. 136 micromol) of the compound produced according to example 78a is reacted analogously to example 78 with use of 3-chlorophenyl isocyanate and, after working up and purification, 25 mg (63 micromol, 46%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3450, 3040, 2950, 2860, 1730, 1650, 1590, 1550, 1480, 1435, 1420, 1300, 1265, 1230, 1165, 775, 735, 700 and 680 cm-1.

Example 85: 6-[ (IR, 2S,5R)-2-[3-(3-Chlorophenyl)-ureidomethyl]-5-fluoro cyclopentyl]-4(Z)-hexenoic acid: mg (63 micromol) of the compound produced according to example 84 is saponified analogously to example 2 and, after working up and purification, 10 mg (26 micromol, 41%) of the title compound is isolated as colorless oil. 109 ’h-NMR (CD3OD) : £ = 1.45-2.4(m,12H), 3.15-3.35(m,2H), 4.76(m,lH), 5.4-5.57(m,2H), 6.9-6.98(m,1H), 7.15-7.24(m,2H), 7.57(s,lH).

Example 86; 6-[(IR,2S,5R)-2-[3-Phenyl-ureidomethyl]-5-fluorocyclopentyl]-4(Z)-hexenoic acid methyl ester: mg (max. 136 micromol) of the compound produced according to example 78a is reacted analogously to example 78 with use of phenyl isocyanate and, after working up and purification, 24 mg (66 micromol, 49%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3450, 3050, 2950, 2860, 1730, 1645, 1595, 1550, 1495, 1435, 1310, 1230, 1170, 750, 735 and 695 cm'1.

Example 87: 6—[(IR,2S,5R)-2-[3-Phenyl-ureidomethyl]-5-fluorocyclopentyl]-4(Z)-hexenoic acid: mg (66 micromol) of the compound produced according to example 86 is saponified analogously to example 2 and, after working up and purification, 16 mg (46 micromol, 70%) of the title compound is isolated as colorless oil.

^-NMR (CD3OD) : cf = 1.45-2.4 (m, 12H) , 3.12-3.35 (m, 2H) , 4.75(m,lH), 5.4-5.55(m,2H), 6.96(t,lH), 7.2-7.38(m,4H). 110 Example 88: 6-((IR,2S,5R)-2-(3-(3,4-Dichlorophenyl)-ureidomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid methyl ester: mg (max. 136 micromol) of the compound produced according to example 78a is reacted analogously to example 78 with use of 3,4-dichlorophenyl isocyanate and, after working up and purification, 26 mg (60 micromol, 44%) of the title compound is isolated as colorless oil.

IR (Film): 3500, 3200-3450, 3010, 2950, 2860, 1730, 1650, 1585, 1540, 1470, 1375, 1265, 1230, 1130, 1025, 815, 735 and 700 Example 89: 6-((IR,2S,5R)-2-(3-(3,4-Dichlorophenyl)-ureidomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid: mg (60 micromol) of the compound produced according to example 88 is saponified analogously to example 2 and, after working up and purification, 15 mg (36 micromol, 60%) of the title compound is isolated as colorless oil.

^H-NMR (CDjOD): J= 1.5-2.4(m,12H), 3.16-3.35(m,2H), 4.75(m,lH), 5.4-5.55(m,2H), 7.21(dd,lH), 7.35(d,lH), 7.71(d,lH). 111 Example 90: 6-[(IR,2S,5R)-2-[3-(4-Nitrophenyl)-ureidomethyl]-5-fluorocyclopentyl ]-4(Z)-hexenoic acid methyl ester: 100 mg (max. 170 micromol) of the compound produced according to example 78a is reacted analogously to example 78 with use of 4-nitrophenyl isocyanate and, after working up and purification, 32 mg (79 micromol, 46%) of the title compound is isolated as yellow oil.

IR (Film): 3200-3450, 3010, 2950, 2870, 1730, 1700, 1670, 1610, 1600, 1550, 1500, 1330, 1300, 1230, 1175, 1110, 850, 735 and 700 cm-1.

Example 91: 6-[(IR,2S,5R)-2-[3-(4-Nitrophenyl)-ureidomethyl]-5-fluorocyclopentyl]-4(Z)-hexenoic acid: mg (79 micromol) of the compound produced according to example 90 is saponified analogously to example 2 and, after working up and purification, 31 mg (79 micromol, 100%) of the title compound is isolated as yellow oil.

^-NMR (CD3OD) :J= 1.5-2.4 (m, 12H) , 3.18-3.35 (m, 2H) , 4.76(m,lH), 5.4-5.55(m,2H), 7.58(d,2H), 8.14(d,2H). 112 Example 92: 6-[(IR,2S,5R)-2-[3-(4-Chlorophenyl)-ureidomethyl]-5-fluorocyclopentyl ] -4 (Z) -hexenoic acid methyl ester: 100 mg (max. 170 micromol) of the compound produced according to example 78a is reacted analogously to example 78 with use of 4-chlorophenyl isocyanate and, after working up and purification, 38 mg (101 micromol, 59%) of the title compound is isolated as colorless solid.

IR (KBr): 3200-3450, 3030, 2960, 2850, 1735, 1650, 1590, 1545, 1470, 1420, 1375, 1265, 1230, 1160, 780, 735 and 700 cm'1.

Example 93: 6-[(IR,2S,5R)-2-[3-(4-Chlorophenyl)-ureidomethyl]-5-fluorocyclopentyl]-4(Z)-hexenoic acid: mg (101 micromol) of the compound produced according to example 92 is saponified analogously to example 2 and, after working up and purification, 33 mg (86 micromol, 85%) of the title compound is isolated as colorless oil. ’h-NMR (CD3OD): cP = 1.45-2.4(m,12H), 3.15-3.35(m,2H), 4.76(m,lH), 5.4-5.55(m,2H), 7.21(dd,2H), 7.35(dd,2H).

Example 94: 6-[(IR,2S,5R)-2-[3-(4-Aminophenyl)-ureidomethyl]-5-fluorocyclopentyl] -hexanoic acid: The solution of 15 mg (38 mmol) of the compound, produced according to example 91, in 1 ml of ethyl acetate is mixed with 5 mg of palladium on carbon (10%) and it is hydrogenated at 1 atmosphere of hydrogen. After taking up the theoretical amount of hydrogen, it is filtered, concentrated by evaporation and the residue is purified chromatographically on an analytic thin-layer slab. A mixture of dichloromethane and ethanol is used as mobile solvent, a mixture of trichloromethane and isopropanol is used as eluant. 13 mg (36 micromol, 94%) of the title compound is isolated as waxy solid.

^-NMR (CD3OD) : cT= 1.2-2.0 (m, 14H) , 2.26(t,2H), 3.13.3(m,2H), 4.76(m,lH), 6.71(d,2H), 7.08(d,2H).

Example 95: 6-[(IR,2S,5R)-2-[3-(4-Chlorophenyl)-ureidomethyl]-5-fluorocyclopentyl]-hexanoic acid: mg (44 micromol) of the compound produced according to example 93 is reacted analogously to example 94 and, after working up and purification, 16 mg (42 micromol, 94%) of the title compound is isolated as colorless solid.

^-NMR (Acetone t^) : J'= 1.25-1.9(m,14H), 2.28(t,2H), 2.53.5(s,lH), 3.18(m,lH), 3.32(m,lH), 4.77(m,lH), 5.99(t,lH), 7.21(d,2H), 7.5(d,2H), 8.08(s,lH). 114 Example 96: 6-((IR,2S,5R)-2-((2-Nitrophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid methyl ester: 147 mg (max. 250 micromol) of the compound produced according to example 78a is reacted analogously to example lb with use of 2-nitrobenzenesulfonic acid chloride and, after working up and purification, 54 mg (126 micromol, 50%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3400, 3100, 3010, 2950, 2920, 2860, 1730, 1590, 1540, 1435, 1415, 1360, 1165, 1070, 855, 780, 740 and 655 Example 97: 6-[(1R,2S,5R)-2-((2-Nitrophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid: mg (126 micromol) of the compound produced according to example 96 is saponified analogously to example 2 and, after working up and purification, 48 mg (116 micromol, 92%) of the title compound is isolated as colorless oil. •h-NMR (CD3OD) : cT= 1.4-2.4 (m, 12H) , 2.99(dd,lH), 3.15(dd,lH), 4.7(m,lH), 5.33-5.5(m,2H), 7.38-7.48(m,3H), 8.038.1(m,lH). 115 Example 98: 6-((IR,2S,5R)-2-((4-Methylphenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid methyl ester: 147 mg (max. 250 micromol) of the compound produced according to example 78a is reacted analogously to example lb with use of tosyl chloride and, after working up and purification, 83 mg (209 micromol, 84%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3400, 3010, 2950, 2870, 1730, 1600, 1435, 1330, 1285, 1160, 1090, 1075, 815 and 665 cm1.

Example 99: 6-((IR,2S,5R)-2-((4-Methylphenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid: mg (209 micromol) of the compound produced according to example 98 is saponified analogously to example 2 and, after working up and purification, 69 mg (180 micromol, 86%) of the title compound is isolated as colorless solid.

IR (Film): (CDjOD) : .4-1.55(m,1H), 1.63-2.38(m,11H), 2.42(s,3H), 2.77(m,lH), 3.92(m,lH), 4.7(m,lH), 5.33-5.5(m,2H), 7.38(d,2H), 7.72(d,2H). z 1X6 Example 199;. 6-[(IR,2S,5R)-2-[(3,4-Dichlorophenyl)-sulfonylaminomethyl]5-fluoro-cyclopentyl]-4(Z)-hexenoic acid methyl ester: 147 mg (max. 250 micromol) of the compound produced according to example 78a is reacted analogously to example lb with use of 3,4-dichlorobenzenesulfonic acid chloride and, after working up and purification, 81 mg (179 micromol, 72%) of the title compound is isolated as colorless oil.

IR (Film): 3090, 3010, 2950, 2850, 1730, 1565, 1450, 1380, 1170, 1140, 1095, 1030, 885, 825, 780, 735, 710, 675 and 625 Example 101: 6-[(IR,2S,5R)-2-((3,4-Dichlorophenyl)-sulfonylaminomethyl]5-fluoro-cyclopentyl]-4(Z)-hexenoic acid: mg (179 micromol) of the compound produced according to example 100 is saponified analogously to example 2 and, after working up and purification, 68 mg (155 micromol, 87%) of the title compound is isolated as colorless oil. 'h-NMR (CDjOD): cf = 1.4-2.4(m,12H), 2.83(dd,lH), 2.97(dd,lH), 4.7(m,lH), 5.35-5.5(m,2H), 7.73(m,2H), 7.98(d,lH). 117 Example 102: 6-((IR,2S,5R)-2-((4-Fluorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid methyl ester: 147 mg (max. 250 micromol) of the compound produced according to example 78a is reacted analogously to example lb with use of 4-fluorobenzenesulfonic acid chloride and, after working up and purification, 56 mg (139 micromol, 56%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3400, 3010, 2950, 2860, 1730, 1600, 1490, 1430, 1330, 1235, 1160, 1090, 840 and 670 cm-1.

Example 103: 6-((IR,2S,5R)-2-((4-Fluorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid: mg (139 micromol) of the compound produced according to example 102 is saponified analogously to example 2 and, after working up and purification, 51 mg (132 micromol, 95%) of the title compound is isolated as colorless oil.

^-NMR (CD3OD) : £ = 1.4-2.36(m,12H) , 2.8(dd,lH), 2.95(dd,lH), 4.7(m,lH), 5.33-5.5(m,2H), 7.3(m,2H), 7.9(m,2H).

Example 104: 6-((IR,2S,5R)-2-(Phenylsulfonylaminomethyl]-5-fluorocyclopentyl] -4 (Z) -hexenoic acid methyl ester: 147 mg (max. 250 micromol) of the compound produced according to example 78a is reacted analogously to example lb 1.18 with use of benzenesulfonic acid chloride and, after working up and purification, 51 mg (133 micromol, 53%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3400, 3060, 3010, 2950, 2860, 1730, 1445, 1325, 1160, 1095, 755, 720 and 690 cm'1.

Example 105: 6-[(IR,2S,5R)-2-[Phenylsulfonylaminomethyl]-5-fluorocyclopentyl ] -4 (Z) -hexenoic acid: mg (133 micromol) of the compound produced according to example 104 is saponified analogously to example 2 and, after working up and purification, 43 mg (116 micromol, 88%) of the title compound is isolated as colorless oil.

^-NMR (CD3OD) : J = 1.4-2.4 (m, 12H) , 2.78(dd,lH), 2.93(dd,lH), 4.7(m,lH), 5.33-5.5(m,2H), 7.52-7.65(ro,3H), 7.86(m,2H).

Example 106: 6-[(IR,2S,5R)-2-((4-Chlorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid methyl ester: 147 mg (max. 250 micromol) of the compound produced according to example 78a is reacted analogously to example lb with use of 4-chlorobenzenesulfonic acid chloride and, after working up and purification, 60 mg (143 micromol, 57%) of the title compound is isolated as colorless oil. 119 IR (Film): 3200-3400, 3090, 3010, 2950, 2870, 1730, 1585, 1470, 1435, 1330, 1160, 1090, 1010, 830, 750 and 620 cm1.

Example 1Q7; 6-[(IR,2S,5R)-2-[(4-Chlorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-4(Z)-hexenoic acid: mg (143 micromol) of the compound produced according to example 106 is saponified analogously to example 2 and, after working up and purification, 45 mg (111 micromol, 78%) of the title compound is isolated as colorless oil.

JH-NMR (CD3OD) : cT= 1.4-2.4 (m, 12H) , 2.8(dd,lH), 2.95(dd,lH), 4.7(m,lH), 5.33-5.5(m,2H), 7.58(d,2H), 7.82(d,2H).

Example 108: 6-[(IR,2S,5R)-2-((4-Methylphenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-hexanoic acid: mg (52 micromol) of the compound produced according to example 99 is reacted analogously to example 94 and, after working up and purification, 20 mg (52 micromol, 99%) of the title compound is isolated as colorless oil.

’H-NMR (CD3OD) : cf = 1.2-1.9(m,14H), 2.28(t,2H), 2.42(d,3H), 2.76(dd,lH), 2.92(dd,lH), 4.68(m,lH), 7.48(d,2H), 7.72(d,2H). 120 Example 109: 6-[(IR,2S,5R)-2-[Phenyl-sulfonylaminomethyl]-5-fluorocyclopentyl ]-hexanoic acid: mg (51 micromol) of the compound produced according to example 105 is reacted analogously to example 94 and, after working up and purification, 19 mg (51 micromol, 100%) of the title compound is isolated as colorless oil. ’h-NMR (CD3OD) : J = 1.2—1.9(m,14H), 2.28(t,2H), 2.77(dd,lH), 2.92(dd,lH), 4.7(m,lH), 7.52-7.66(m,3H), 7.85(m,2H).

Example 110: 6-[(IR,2S,5R)-2-((4-Chlorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-hexanoic acid: mg (47 micromol) of the compound produced according to example 107 is reacted analogously to example 94 and, after working up and purification, 17 mg (42 micromol, 89%) of the title compound is isolated as colorless oil.

^-NMR (CD3OD) : cP = 1.2-1.9(m,14H) , 2.29(t,2H), 2.81(dd,lH), 2.95(dd,lH), 4.72(m,lH), 7.58(d,2H), 7.82(d,2H).

Example 111: 6-((IR,2S,5R)-2-((4-Fluorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-hexanoic acid: mg (49 micromol) of the compound produced according to example 103 is reacted analogously to example 94 and, after 121 working up and purification, 19 mg (49 micromol, 100%) of the title compound is isolated as colorless oil. ’h-NMR (CD3OD): cf = 1.2-1.96(m,14H), 2.28(t,2H), 2.78(dd,lH), 2.93(dd,lH), 4.72(m,lH), 7.3(m,2H), 7.9(m,2H).

Example 112: 6- ((IR,2S,5R)-2-[3-(4-Fluorophenyl)-ureidomethyl]-5-fluoro cyclopentyl]-hexanoic acid: mg (27 micromol) of the compound produced according to example 79 is reacted analogously to example 94 and, after working up and purification, 10 mg (27 micromol, 100%) of the title compound is isolated as colorless oil.

’H-NMR (CDjOD) : J = 1.25-2.0(m,14H), 2.26(t,2H), 3.13.32(m,2H), 4.76(m,lH), 6.97(m,2H), 7.31(m,2H).

Example 113: 7- [(1R,2S,5R)-2-((4-Chlorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 129 mg (max. 245 micromol) of the compound produced according to example 113a is reacted analogously to example lb with use of 4-chlorobenzenesulfonic acid chloride and, after working up and purification, 49 mg (113 micromol, 46%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3400, 3010, 2950, 2860, 1730, 1585, 1435, 1330, 1160, 1090, 830, 750, 735, 700 and 620 cm-1. 122 Example 113a: 7-((IR,2S,5R)-2-Aminomethyl-5-fluoro-cyclopentyl]-5(Z)heptenoic acid methyl ester: 416 mg (1.47 mmol) of the compound produced according to example 113b is reacted analogously to example 78a and, after working up and purification, 776 mg (max. 1.47 mmol, about 50%) of the title compound is isolated as colorless oil.

Example 113b: 7-((IR,2S,5R)-2-Azidomethyl-5-fluoro-cyclopentyl]-5(Z)heptenoic acid methyl ester: 502 mg (1.56 mmol) of the compound produced according to example 113c is reacted analogously to example 78b and, after working up and purification, 416 mg (1.47 micromol, 94%) of the title compound is isolated as colorless oil.

IR (Film): 2950, 2870, 2100, 1735, 1435, 1360, 1245 and 1160 cm'1.

Example 113c: — [(IR,2S,5R)-2-Bromomethyl-5-fluoro-cyclopentyl]-5(Z) heptenoic acid methyl ester: 410 mg (1.59 mmol) of the compound produced according to example 113c is reacted analogously to example 78c and, after working up and purification, 502 mg (1.56 mmol, 98%) of the title compound is isolated as colorless oil. 3 IR (Film): 2950, 2870, 1735, 1435, 1360, 1245, 1225, 1170 and 950 cm-1.

Example 113d; 7-((IR,2S,5R)-2-Hydroxymethyl-5-fluoro-cyclopentyl]-5(Z)heptenoic acid methyl ester (A) and 7-((5S)-5-hydroxy-cyclopent 1-enyl]-5(Z)-heptenoic acid methyl ester (B): 3.75 g of the substance mixture produced according to example 113e is reacted analogously to example 78d and, after working up and purification, 941 mg (3.95 mmol, 38%) of title compound B as a nonpolar component as well as 820 mg (3.17 mmol 31%) of title compound A as a polar component are each isolated as colorless oil.

IR (Film) of A: 3200-3600, 3050, 2950, 2870, 1735, 1435, 1360, 1165, 1040, 945 and 875 cm 1 IR (Film) of B: 3200-3600, 3050, 2950, 2860, 1735, 1435, 1360, 1200, 1160 and 1025 cm 1 .

Example 113e: 7-[(IR,2S,5R)-2-tert-Butyldiphenylsilyloxymethyl-5-fluorocyclopentyl ] -5( Z) -heptenoic acid methyl ester and 7-((5S)-5(tert-butyldiphenylsilyloxymethyl)-cyclopent-l-enyl]-5(Z)heptenoic acid methyl ester: .08 g (10.3 mmol) of the compound produced according to example li is reacted analogously to example lg and, after 124 working up and purification, 3.75 g of a mixture of both title compounds is isolated as colorless oil.

Example 114: 7-[ (IR, 2S,5R) -2-( (4-Chlorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (113 micromol) of the compound produced according to example 113 is saponified analogously to example 2 and, after working up and purification, 47 mg (112 micromol, 99%) of the title compound is isolated as colorless oil.

!H-NMR (CDClj) : J = 1.35-2.2(m,12H), 2.38(t,2H), 2.93(t,2H), 4.79(m,lH), 5.35-5.58(m,3H), 7.48(d,2H), 7.79(d,2H).

Example 115: 7-[(IR,2S,5R)—2—[(4-Fluorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 129 mg (max. 245 micromol) of the compound produced according to example 113a is reacted analogously to example lb with use of 4-fluorobenzenesulfonic acid chloride and, after working up and purification, 50 mg (120 micromol, 49%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3400, 3060, 3010, 2940, 2860, 1730, 1590, 1490, 1435, 1330, 1235, 1165, 1150, 1090, 840, 735, 700 and 670 125 Example 116: 7-((1R,2S,5R)-2-((4-Fluorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (120 micromol) of the compound produced according to example 115 is saponified analogously to example 2 and, after working up and purification, 44 mg (110 micromol, 91%) of the title compound is isolated as colorless oil.

*H-NMR (CDC13) : cf = 1.35-2.2(m,12H), 2.38(t,2H), 2.92(t,2H), 4.77(m,lH), 5.35-5.58(m,3H), 7.2(m,2H), 7.79(m,2H).

Example 117: 7-[(IR,2S,5R)-2-[3-(4-Chloropheny1)-ureidomethyl]-5-fluorocyclopentyl]-5(Z)-heptenoic acid methyl ester: 129 mg (max. 245 micromol) of the compound produced according to example 113a is reacted analogously to example 78 with use of 4-chlorophenyl isocyanate and, after working up and purification, 60 mg (146 micromol, 60%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3400, 3040, 2950, 2850, 1730, 1650, 1595, 1545, 1470, 1420, 1375, 1260, 1225, 1160, 785, 735 and 700 cm'1.

Example 118: 7-[(IR,2S,5R)-2-(3-(4-Chlorophenyl)-ureidomethyl]-5-fluorocyclo-pentyl]-5(Z)-heptenoic acid: mg (146 micromol) of the compound produced according to example 117 is saponified analogously to example 2 and, after < working up and purification, 42 ng (106 micromol, 72%) of the title compound is isolated as colorless oil. ’h-NMR (CDC13) : cT= 1.38-2.2(m,12H), 2.36(t,2H), 3.2(t,2H), 4.78(m,lH), 5.35-5.48(m,2H), 5.58(t,lH), 7.15-7.25(m,4H), 7.49(S,1H).

Example 119: 7-((1R,2S,5R)-2-[3-(4-Nitrophenyl)-ureidomethyl]-5-fluorocyclopentyl] -5(Z)-heptenoic acid methyl ester: 129 mg (max. 245 micromol) of the compound produced according to example 113a is reacted analogously to example 78 with use of 4-nitrophenyl isocyanate and, after working up and purification, 53 mg (126 micromol, 51%) of the title compound is isolated as colorless oil.

IR (Film): 3200-3400, 3080, 3010, 2950, 2860, 1730, 1700, 1670, 1610, 1600, 1550, 1500, 1325, 1300, 1230, 1175, 1110, 850, 735 and 700 cm'1.

Example 120: 7-((1R,2S,5R)-2-[3-(4-Nitrophenyl)-ureidomethyl]-5-fluorocyclopentyl ]-5(Z)-heptenoic acid: mg (126 micromol) of the compound produced according to example 119 is saponified analogously to example 2 and, after working up and purification, 44 mg (105 micromol, 83%) of the title compound is isolated as yellow oil. 127 ^H-NMR (CDCI3) : = 1.32-2.15(m,12H), 2.29(t,2H), 3.12(t,2H), 4.72(m,lH), 5.25-5.4(ro,2H), 5.5(t,lH), 7.087.15(m,4H), 7.4(S,1H).

Example 121: 7-((IR,2S,5R)—2—[(E/Z)-3-(3,4—Dichlorophenyl)ureidoiminomethyl]-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (max. 199 micromol) of the compound produced according to example 121a is reacted analogously to example 62b with use of 4-(3,4-dichlorophenyl)semicarbazide hydrochloride and, after working up and purification, 75 mg (164 micromol, 82%) of the title compound is isolated as colorless oil.

IR (Film): 3360, 3200, 3100, 2940, 1730, 1690, 1580, 1520, 1470, 1390, 1290, 1220, 1130, 1025, 950, 875, 815, 740 and 690 Example 121a: 7-((IR,2S,5R)-2-Formyl-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 410 mg (1.59 mmol) of compound A produced according to example 113d is reacted analogously to example 50b and, after working up, 440 mg (max. 1.59 mmol) of the title compound is isolated as colorless oil, which is further reacted without purification. 128 Example 1221 7-((IR,2S,5R)-2-[(E/Z)-3-(3,4-Dichlorophenyl)ureidoiminomethyl]-5-fluoro-cyclopentyl]-5(Z) -heptenoic acid: mg (83 micromol) of the compound produced according to example 121 is saponified analogously to example 2 and, after working up and purification, 28 mg (63 micromol, 76%) of the title compound is isolated as colorless oil.

JH-NMR (CDC13) : 0= 1.62-2.5(m,14H), 2.77-2.88 (m, 0.25H) , 4.78(m,lH), 5.2-5.3(m,0.25H), 5.42-5.58(m,1.75H), 6.52(d,0.25H), 7.21(d,0.75H), 7.23-7.4(m,2H), 7.72(dd,lH), 8.02(s,0.75H), 8.28(s,0.25H), 9.62(s,0.75H), 10.01(s,0.25H).

Example 123: 7-((lR,2S,5R)-2-((E/Z)-3-(4-Chlorophenyl) ureidoiminomethyl]-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 165 mg (max. 596 micromol) of the compound produced according to example 121a is reacted analogously to example 62b with use of 4-(4-chlorophenyl)semicarbazide hydrochloride and, after working up and purification, 198 mg (467 micromol, 78%) of the title compound is isolated as colorless oil.

IR (Film): 3370, 3200, 3100, 2940, 2870, 1730, 1685, 1590, 1525, 1400, 1310, 1225, 1090, 950, 825 and 740 cm1. 129 Example 124: 7-((lR,2S,5R)-2-[(E/Z)-3-(4-Chlorophenyl)ureidoiminomethyl]-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (142 micromol) of the compound produced according to example 123 is saponified analogously to example 2 and, after working up and purification, 50 mg (122 micromol, 86%) of the title compound is isolated as colorless oil.

^-NMR (000^):^ = 1.62-2.5 (m, 14H) , 2.77-2.88 (m, 0.25H) , 4.76(m,lH), 5.2-5.3(m,0.25H), 5.42-5.58(m,1.75H), 6.52(d,0.25H) 7.2(d,0.75H), 7.28(m,2H), 7.43(m,2H), 8.02(s,0.75H), 8.24(s,0.25H), 9.64(s,0.75H), 9.98(s,0.25H).

Example 125: 7-[(IR,2S,5R)-2-[3-(4-Nitrophenyl)-ureidomethyl]-5-fluorocyclopentyl] -heptanoic acid: mg (56 micromol) of the compound produced according to example 120 is reacted analogously to example 94 and, after working up and purification, 18 mg (44 micromol, 79%) of the title compound is isolated as yellow oil. lH-NMR (CD3OD) : = 1.25-2(m,16H), 2.23(t,2H), 3.123.36(m,2H), 4.76(m,lH), 7.58(d,2H), 8.13(d,2H). 130 Example 126: 7-((IR,2S,5R)-2-(3-(4-Chlorophenyl)-ureidomethyl]-5-fluoro cyclopentyl]-heptanoic acid: mg (52 micromol) of the compound produced according to example 118 is reacted analogously to example 94 and, after working up and purification, 20 mg (50 micromol, 96%) of the title compound is isolated as colorless solid.

^-NMR (CD3OD) : cP = 1.25-2 (m, 16H) , 2.23(t,2H), 3.123.32(m,2H), 4.75(m,lH), 7.21(d,2H), 7.35(d,2H).

Example 127: 7-((IR,2S,5R)-2-((4-Fluorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-heptanoic acid: mg (55 micromol) of the compound produced according to example 116 is reacted analogously to example 94 and, after working up and purification, 19 mg (47 micromol, 86%) of the title compound is isolated as colorless solid.

*H-NMR (CDClj): J = 1.1-2(m,16H), 2.36(t,2H), 2.833.08(m,2H), 4.73(m,lH), 5.08(t,lH), 7.2(m,2H), 7.89(m,2H).

Example 128: 7-((IR,2S,5R)-2-((4-Chlorophenyl)-sulfonylaminomethyl]-5fluoro-cyclopentyl]-heptanoic acid: mg (56 micromol) of the compound produced according to example 114 is reacted analogously to example 94 and, after 11 J. JL working up and purification, 20 mg (48 micromol, 85%) of the title compound is isolated as colorless solid. ’h-NMR (CDC13) : cT= 1.1-1.95(m,16H), 2.3(t,2H), 2.763(m,2H), 4.68(m,lH), 5.02(t,lH), 7.42(d,2H), 7.73(d,2H).

Example 129: 7-[(IR,2 S,5R)-2-((E/Z)-2-(4-Fluoropheny1sulfony1) hydrazonomethyl]-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: 165 mg (max. 596 micromol) of the compound produced according to example 121a is reacted analogously to example 62b with use of 4-fluorobenzenesulfonyl hydrazide and, after working up and purification, 225 mg (525 micromol, 88%) of the title compound is isolated as colorless oil.

IR (Film): 3180, 2950, 2860, 1730, 1710, 1590, 1490, 1435, 1365, 1320, 1235, 1170, 1155, 1090, 835 and 670 cm1.

Example 130: 7-((IR,2S,5R)-2-[(E/Z)-2-(4-Fluorophenylsulfonyl)hydrazonomethyl]-5-fluoro-cyclopentyl)-5(Z)-heptenoic acid: mg (140 micromol) of the compound produced according to example 129 is saponified analogously to example 2 and, after working up and purification, 52 mg (125 micromol, 90%) of the title compound is isolated as colorless oil.

JH-NMR (CDCI3) : = 1.54-2.5(m,14H), 4.8(m,lH), 5.225.56(m,lH), 7.1-7.23(m,3H). 132 Example 131: 7-((1R,2S,5R)-2-((E/Z)-2-(4-Methylphenylsulfonyl)hydrazonomethyl]-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid methyl ester: mg (max. 199 micromol) of the compound produced according to example 121a is reacted analogously to example 62b with use of 4-toluenesulfonyl hydrazide and, after working up and purification, 78 mg (192 micromol, 97%) of the title compound is isolated as colorless oil.

IR (Film): 3200, 3000, 2950, 2870, 1730, 1710, 1595, 1435, 1360, 1320, 1160, 1090, 1030, 930, 810, 705 and 670 cm'1.

Example 132: 7-((IR,2S,5R)-2-((E/Z)-2-(4-Methylphenylsulfonyl) hydrazonomethyl]-5-fluoro-cyclopentyl]-5(Z)-heptenoic acid: mg (96 micromol) of the compound produced according to example 131 is saponified analogously to example 2 and, after working up and purification, 33 mg (84 micromol, 88%) of the title compound is isolated as colorless solid. lH-NMR (CDC13) : cT = 1.55-2.2(m,12H) , 2.32(t,2H), 2.42(s,3H), 4.77(m,lH), 5.23-5.55(m,2H), 6.69(d,0.1H), 7.13(d,0.9H), 7.3(d,2H), 7.8(d,2H). 133 Example 133: 7-((IR,2S,5R)-2-((E/Z)-2-(4-Fluorophenylsulfonyl)hydrazonomethyl]-5-fluoro-cyclopentyl]-heptanoic acid: mg (89 micromol) of the compound produced according to example 130 is reacted analogously to example 94 and, after working up and purification, 14 mg (34 micromol, 38%) of the title compound is Isolated as colorless oil.

^-NMR (CD3OD) : cf = 1.0-1.75 (m,15H) , 2.08-2.22 (m, 3H) , 4.62(m,lH), 7.04(d,lH), 7.21(m,2H), 7.82(m,2H).

Example 134: 7-((IR,2S,5R)-2-((E/Z)-2-(4-Methylphenylsulfonyl) hydrazonomethyl]-5-fluoro-cyclopentyl]-heptanoic acid: mg (49 micromol) of the compound produced according to example 132 is reacted analogously to example 94 and, after working up and purification, 9 mg (23 micromol, 47%) of the title compound is isolated as colorless oil. ’h-NMR (CD3OD): S = 1.12-1.94(m,16H), 2.16-2.32(m,3H), 2.92(s,3H), 4.7(m,lH), 7.12(d,lH), 7.37(d,2H), 7.76(d,2H). 134 Example 135: 7-((1R,2S,5R)-2-((E/Z)-3-(4-Chlorophenyl)ureidoiminomethyl]-5-fluoro-cyclopentyl]-heptanoic acid (A) and 7-((IR, 2S,5R)-2-[3-(4-Chlorophenyl)-ureidoaminomethyl]-5-fluorocyclopentyl ]-heptanoic acid (B): mg (49 micromol) of the compound produced according to example 124 is reacted analogously to example 94 with use of PtO2 and, after working up and purification, 11 mg (27 micromol, 54%) of title compound A as a nonpolar component, as well as 8 mg (19 micromol, 39%) of title compound B are each isolated as waxy solid.

^-NMR (CD3OD) of A: J = 1.27-2.12 (m, 15H) , 2.23(t,2H), 2.43(m,lH), 4.78(m,2H), 7.22(d,lH), 7.27(d,2H), 7.5(d,2H). •h-NMR (CD3OD) of B: J = 1.25-2 (m, 16H) , 2.26(t,2H), 2.74(dd,lH), 2.95(dd,lH), 4.76(m,lH), 7.27(d,2H), 7.45(d,2H).

Claims

Claims:

1. Cyclopentane derivatives of formula I, R 5 can mean hydrogen or Cj-Cjq alkyl, Cj-Cjq cycloalkyl, Cj-C^ aralkyl, optionally substituted by halogen, phenyl, CJ-C4 alkoxy or di- (C1-C4) -alkylamino, phenacyl or C6-C|2 aryl substituted by Y or a 5- or 6-membered heterocyclic radical with at least one N, O or S atom or -CONHR 7 with R 7 meaning hydrogen, Cj-Cjq alkyl, C6-Cj2 arylsulfonyl, Cj-Cjq alkanoyl or Cj-Cjq alkanesulfonyl, X means -(CH 2 )p-, -CH2-0- or -CH2-S-, Z,A, independent of one another, mean a direct bond, (Z)-CH=CH-, (E)-CH=CH- or -C=C-, p means 0 to 5, R 2 means fluorine, OH, n,r, independent of one another, mean 0 to 2, R^ means OR^ or r\ 3 36 W means a direct bond, a -((CH 2 ) n -V] q group, a -(CH 2 ) n -V(CH 2 )q-V group, a free or functionally modified hydroxymethylene group or a free or functionally modified the group, and hydroxy group can be respectively in alpha- or beta-position, q means 1 or 2, D means a direct bond, a straight-chain saturated alkylene group with 1-5 C atoms, a branched saturated alkylene group or a straight-chain or branched unsaturated alkylene group with 2-5 C atoms, which can be optionally substituted by fluorine atoms, - (CH 2 ) n -NH-SO 2 -, N'°< “< CH 2)ri\ 0. N I H Η H . N X N .so r -(0¾) II n‘N Ν' Η H H I X* » so 2 ><3 -(CH 2 ) n -NH-NH-SO 2 - or V means an O or S atom, ο 0 E means a direct bond, -C>C- or -CH=CR -, and R means hydrogen, C1-C5 alkyl, halogen or trifluoromethyl, 137 AWDE together mean a direct bond, AW together mean a direct bond, DE together can be a direct bond, 4 R means Cj-Cjq cycloalkyl or Cj-Cj 0 alkyl optionally substituted by Y, m means 1 or 2, Yj and Y 2 are the same or different and mean Y, Y means hydrogen, halogen, Nj, CF3, OR 6 , N0 2 , NH 2 , CN, COOR 6 or Cj-Cjq alkyl, R 6 can be hydrogen, Cj-Cjq alkyl, 0β-0] 2 aryl or Cy-Cjg aralkyl optionally substituted by halogen and, if R 5 means hydrogen, their salts with physiologically compatible bases, as well as the alpha-, beta- or gamma-cyclodextrin clathrates, as well as the compounds of formula I encapsulated with liposomes. 133

2. Pharmaceutical agents consisting of one or more compounds of claim 1 and usual auxiliary agents, vehicles and additives.

3. Process for the production of cyclopentane derivatives of formula I, characterized in that the hydroxy compound of formula II in which R 1 , R 3 , R 3 , R 4 , X and Z have the above-indicated meanings and R 1 represents a -COOR 5 ester group with R 5 in the aboveindicated meaning with the exception of hydrogen, is reacted with a halogen compound of formula Hal-W-R 4 (III), in which Hal, W and 4. . . ... R have the above-mentioned meanings or after oxidation with oxalyl chloride/DMSO with a dimethyl phosphonate of formula V 0 0 (V), in which D, E and R 4 have the above-mentioned meaning, in the presence of sodium hydride or sodium hydride/bromine and then is reduced and optionally hydrobromic acid is cleaved or the oxidation product from II and oxalyl chloride/DMSO is reacted . 4 with an amine of formula H 2 N-O-R (X) , 139 V h 2 n^ JU z r4 H 2 N-NH-SO 2 -R 4 (XIII) or V V (XI) ' in which r4 has the Η H above-indicated meaning, or, after oxidation and reaction with thionyl chloride and sodium azide, the intermediate amine of formula (VIII) . . 4 4 is reacted with a compound of formula Hal-SO 2 -R (IX) or O=C=N-R (XII) , in which Hal and R 4 have the above-mentioned meaning, or, after bromation, formation of azide and reduction, the intermediate amine of formula (XIV) 4 4 is reacted with a compound of formula Hal-SO 2 -R (IX) or O=C=N-R (XII) , in which Hal and R 4 have the above-mentioned meaning, C-C multiple bonds are optionally hydrogenated and the resulting esters are saponified, converted to salt, converted to cyclodextrin clathrates or encapsulated with liposomes 141

4. Use of a compound of formula I as defined in claim 1 for the preparation of a medicament for use in a method of prophylaxis or treatment.

5. A compound substantially as hereinbefore described with reference to the Examples.

6. A composition substantially as hereinbefore described with reference to the Examples.

7. A use substantially as hereinbefore described with reference to the Examples.