FI120399B - Förfarande för framställning av pyran-2-oner och 5,6-dihydropyran-2-oner, som är användbara till behandling av HIV och andra retrovirus - Google Patents
Förfarande för framställning av pyran-2-oner och 5,6-dihydropyran-2-oner, som är användbara till behandling av HIV och andra retrovirus Download PDFInfo
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- FI120399B FI120399B FI952302A FI952302A FI120399B FI 120399 B FI120399 B FI 120399B FI 952302 A FI952302 A FI 952302A FI 952302 A FI952302 A FI 952302A FI 120399 B FI120399 B FI 120399B
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Claims (28)
1. Förfarande för framställning av en farmaceutisk förening enligt den allmänna formeln I 5 01 1 s , Vv1 ' Jio—ηΠ ^ h väri Ri är a) -(CH2)n-CH(R5)-(CH2)m-R4, 10 b) -CH(aryl)-CH[C(0)-0-C,-C6-alkyl]2, c) -C(C3-C5-cykloalkyl)-(CH2)n-R4, d) -CH(aryl)-CH=CH-C]-C6-alkyl, e) -CH(aryl)-CH=CH-(CH2)m-aryl, f) -C(C,-C6-alkyl)=CH-aryl eller 15 g) -(CH2)n-CH=CH-(CH2)n-aryl, . . väri R2 är • · · ’· a) väte, • · · ' *..·* b) halogen, :V c) C,-C6-alkyl-[0-(CH2)2]q-(CH2)n- eller 20 d) CrC6-alkyl, : väri R3 är • · · · :*·*; a) C2-C10-alkyl eventuellt substituerad mednoll (0) tili fem (5) halo, b) R4-(CH2)m-CH(R6)-(CH2)n-, c) R4-(CH2)p-, 25 d) R4-CH=CH-, ‘Τ' e) CH2=CH-(CH2)p-, Mj f) R4(CH2)mX,C(0)(CH2)n-, g) aryl eller h) C i -C6-alkyl-0-C(0)-(CH2)n-, • · . 30 väri R4 är a) aryl, b) het, 253 c) C3-C7-cykloalkyl, d) -CH-aryl OH 5 e) C i -C6-alkyl-[0-(CH2)2]q-(CH2)n-, f) halogen, g) het-O-, h) het-C(O)-, i) aryl-(CH2)n-0-C(0)-s 10 j) trifluormetyl; k) -CH-het, OH väri R5 är 15 a) CrCio-alkyl, b) C2-Cio-alkenyl, c) C3-C7-cykloalkyl eller d) -(CH2)n-aryl, väri Rö är 20 a) CrCio-alkyl, . b) -(CH2)n-C3-C7-cykloalkyl, c) -(CH2)p-aryl, [···* d) -(CH2)p-het, eller : e) hydroxi-, ·.**: 25 vari Xi är-NR7-, ·.· · väri R7 är väte, :T: vari aryl är a) fenyl substituerad med noil (0) till tre (3) Rb, eller b) naftyl substituerad med noil (0) till tre (3) R8, .···. 30 vari het är en 5- eller 6-ledad mättad eller icke mättad ring utvald bland tetra- • · hydrofuranyl, dioxolanyl, morfolinyl, pyridyl, tiazolyl, kinolyl, furanyl, tiofenyl, isoxazolyl, oxadiazolyl, tetrazolyl, piperidinyl, pyrrolidinyl, pyrrolidinonyl, indolyl, tetrahydropyranyl, dihydropyranyl eller dihydrobenzoxinyl, och substituerad med noil (0) till tre (3) R9, ....: 35 vari R8 och R9 oberoende är a) CpCg-alkyl substituerad med noli (0) till tre (3) halo, 254 b) hydroxi, c) hydroxi-CrC5 alkyl; d) -(CH2)n-0-Ci-C5-alkyl substituerad med noli (0) till tre (3) hydroxi, e) halogen, 5 f) C3-C7-cykloalkyl, g) nitro, h) -(CH2)n-NHC(0)-0-(CH2)p-R12, Ϊ) “(CH2)n-Rl2, j) -S02-Ri2, 10 k) -(CH2)n-X2-(CH2)n-R12, l) (CH2)„-X2-(CH2)n-R15, m) -(CH2)n-X2-CH=CH-R|2, n) -(CH2)n-X2-CrCio-alkyl substituerad med noli (0) till tre (3) halo, o) -X2-(CH2)p-NH-C(0)-0-C, -C6-alkyl, 15 p) -NH-AA-P] eller q) -(CH2)p-N3, väri X2 är a) -NH-C(O)-, b) -NH-S02- eller 20 c) -NH-C(0)-NH-, : väri R10 är väte, 1./ väri Rn är //1 a) väte, b) C,-C6-alkyl, [· 25 c) -(CH2)n-aryl eller d) -(CH2)n-C3-C7-cykloalkyl, • · · · eller väri R10 och R!) tagna tillsammans bildar en dubbelbindning, eller vari R3 och R\ \ tagna tillsammans bildar a) C3-C8 cykloalkyl substituerad med noil (0) till tre (3) hydroxyl, =N-OH, =0 .*·*; 30 (oxo), eller en skyddad form därav, eller substituerad vid α-positionen med Rh, • · · ·. eller • · · *;|·* b) en 5- eller 6-ledad mättad ring, vilken innehäller en (1) eller tvä (2) syreatomer, '...· väri R12 är fenyl substituerad med noil (0) till tre (3) R]3, ·:··· variRI3är ....j 35 a) Ci-Cio-alkyl substituerad med noli (0) till tre (3) halo, b) hydroxi-CrC5-alkyl; 255 c) -(CH2)n-0-C, -C5-alkyl, d) halogen, e) -CN eller f) -(CH2)n-fenyl, eventuellt substituerad med 0ΞΝ, 5 van R|4 är -(CH2)n-aryl, van R15 är indolyl eller pyridyl, eventuellt substituerad med amino eller trifluormetyl, väri AA är en aminosyrarest vald bland alanyl, histidinyl och glutamyl, vari Pi är väte eller en kväveskyddande grupp vald bland CrC6-alkoxikarbonyl och 10 tosyl, väri m och n oberoende är noil (0) till fern (5), vari p är ett (1) till fern (5), väri q är ett (1) till fem (5), eller ett farmaceutiskt godtagbart salt därav, 15 forutsatt att när R) är -CHR4R5, R2 är H eller CrC6-alkyl, R4 är fenyl eller naftyl substituerad med OH i position 2 eller 4, eller fenyl som kan vara substituerad med minst en alkyl eller hydroxialkyl, eller med halo i position 2 eller 4, R5 är CrCio-alkyl eller aryl och R10 och Ru tagna tillsammans bildar en dubbelbindning, sä är R3 icke alkyl eller haloalkyl, 20 : kännetecknat av att • · · • · • · · • · • · a) en förening enligt formel V • · · • · • · ί OH • · · I • · I : iw • · · / NX Rio" i \* * ; v Ri'^Jl I 25 « · · • · · • · *··.* vari R2, R3, Ri0 och R] ] har ovan angiven betydelse, omsättes med en förening enligt : formel VI ··· • · · • φ • ·
30 R,-Xi VI • · ’·**· vari R! har ovan angiven betydelse och Xi är en reaktiv grupp, 256 b) en förening enligt formel VII OH ^rI Rio— ! VII Rn——: 5 väri Ru R2, R)0 och R, j har ovan angiven betydelse, omsättes med en förening enligt formel VIII R3a-X2 VIII 10 väri R3a är ai) CpCg-alkyl, eventuellt substituerad med nolla (0) till fern (5) halogen, bl) R4-(CH2)m-CH(R6)-(CH2)n,-cl) R4-(CH2)p.r el) CH2=CH-(CH2)P.,-15 fl) R4-(CH2)mX1 C(0)-(CH2)n., -hl) Ci-C6-alkyyli-0-C(0)-(CH2)n.1 väri R4, R^, X,, m, n och p har ovan angiven betydelse, förutsatt att n icke är noll, och V*: X2 är en reaktiv grupp, ♦ ·· ··« • 20 c) för ffamställning av en förening enligt formel I, väri R3 är R4-(CH2)mXiC(0)-CH2- :*·.· , väri R4, X) och m har ovan angiven betydelse, omsättes en förening enligt formel • :*; VII, väri Rj, R2, R]0 och Rn har ovan angiven betydelse, med en förening enligt ··· · formel IX • · · ..... 25 R4-(CH2)m-NCO IX • · · • · · • · ’·;·* väri R4 och m har ovan angiven betydelse, • · · • · · ··♦ d) för framställning av en förening enligt formel CC-5 ··· 30 • · • · 257 OH S cc'5 (cTpj^o^0 ^ omsättes en förening enligt formel CC-3 O rf'O CC-3 erA* 5 ^ ^ med en förening enligt formel CC-2 ·:·! =:::= • · · • · · • · : 10 i ett kolvätelösningsmedel i närvaro av en triakylamin vid en förhöjd temperatur för • · : att ge en förening enligt formel CC-4 • · · · • · · • · · • · · 5 0 ..... S CC*4 • · 258 nämnda förening enligt formel CC-4 behandlas med en bas i en vatten/alkoholblandning, och sedan behandlas den erhällna blandningen med en syra för att ge en förening enligt formel CC-5, e) för framställning av en förening enligt formel I, väri Rj är en ovan definierad 5 grupp, som har en substituent R8 eller R9, som har en av de ovan angivna betydelsema k) - o), överföres motsvarande förening väri R8 eller R9 är -NH2j tili en önskad substituent R8 eller R9, f) en förening enligt formel I, väri Rj är en ovan definierad grupp, som har en substituent R8 eller R9, som har ovan angivna betydelse d), överföres tili 10 motsvarande förening, väri R8 eller R9 är hydroxyl eller hydroxyl-Ci-C5-alkyl, g) en kol-kol-dubbelbindning i gruppen Ri överföres tili en enkel bindning, h) en förening enligt formel I, väri en hydroxylgrupp i 4-position är skyddad, överföres tili motsvarande förening som icke är skyddad, eller i) en förening enligt formel I överföres tili ett farmaceutiskt acceptabelt sait. 15
2. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en förening enligt formel I väri Ri är -CH(R5)-R4, R2 är väte,
20 R3 är R4-(CH2)P-, : R4 är aryl, • · · l..' aryl är fenyl substituerad med noll (0) tili tre (3) R8, R5ärCrC,o-alkyl, ·. ^ R8 är-X2-R]5,
25 X2 on -NH-S02, • · : R15 är indolyl eller pyridyl, eventuellt substituerad med amino eller trifluormetyl, v : Rio är väte, Ri 1 är CrC6-alkyl, ;;.· p är noll (0) tili fem (5). 30 • ·
3. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en • · · '·!·* förening, utvald frän gruppen som bestär av 3- (a-etylbensyl)-4-hydroxi-6-fenyl-2H-pyran-2-on; 6-bensyl-3-(a -etylbensyl)-4-hydroxi-2H-pyran-2-on; 35 3-( a-etylbensyl)-6-fenetyl-4-hydroxi-2H-pyran-2-on; 4- hydroxi-6-fenetyl-3-(a -propyl-p-brombensyl)-2H-pyran-2-on; 259 6-(p-bromfenetyl)-3-(a -etylbensyl)-4-hydroxi-2H-pyran-2-on; 3-(a-etylbensyl)-6-(o-fluorfenetyl)-4-hydroxi-2H-pyran-2-on; 3-(a-etylbensyl)-4-hydroxi-6-(3-fenylpropyl)-2H-pyran-2-on; 3-(a-etylbensyl)-4-hydroxi-6-propyl-2H-pyran-2-on; 5 3-(a-etylbensyl)-4-hydroxi-6-(3-butenyl)-2H-pyran-2-on; 3- (a-etylbensyl)-4-hydroxi-6-[[(fenylamino)karbonyl]metyl]-2H-pyran-2-on; 4- hydroxi-6-fenetyl-3-(a-vinylbensyl)-2H-pyran-2-on; 3-( a-etylbensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 3-([R]-a-etylbensyl)-4-hydroxi-6-([R]-a-etylfenetyl)-2H-pyran-2-on; 10 3-([R]-a-etylbensyl)-4-hydroxi-6-([S]-a-etylfenetyl)-2H-pyran-2-on; 3-([S]-a-etylbensyl)-4-hydroxi-6-([R]-a-etylfenetyl)-2H-pyran-2-on; 3-([S]-a-etylbensyl)-4-hydroxi-6-([S]-a-etylfenetyl)-2H-pyran-2-on; natrium (3S,6R)-3-(a-etylbensyl)-6-(a-etylfenetyl)-2H-pyran-2-on-4-oxid; 3-(a-etylbensyl)-1 -etylpropyl-4-hydroxi-2H-pyran-2-on; 15 3- a-etylbensyl)-4-hydroxi-6-(p-metoxistyryl)-2H-pyran-2-on; 3-(a etylbensyl)-4-hydroxi-6-(2-naft-2-yletyl)-2H-pyran-2-on; 3-(a-etylbensyl)-4-hydroxi-6-(l-etyl-2-naft-2-yletyl)-2H-pyran-2-on; 3-(a-etylbensyl)-4-hydroxi-6-(2-naft-1 -yletyl)-2H-pyran-2-on; 3-(a-etylbensyl)-4-hydroxi-6-( 1 -etyl-2-naft-1 -yletyl)-2H-pyran-2-on; 20 3-(a-cyklopropylbensyl)-4-hydroxi-6-(3-fenylpropyl)-2H-pyran-2-on; . . : 3 -(a-cyklopropylbensyl)-6-( 1 -etylpropyl)-4-hydroxi-2H-pyran-2-on; • · · 3-(a-cyklopropylbensyl)-6-(a-bensylfenetyl)-4-hydroxi-2H-pyran-2-on; • · .’** 3-(a-cyklopropylbensyl)-4-hydroxi-6-fenetyl-2H-pyran-2-on; och *. \ 3-(a-cyklopropylbensyl)-6-(l-propylbutyl)-4-hydroxi-2H-pyran-2-on; • · · *· *: 25 • · :.: : 4. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en • · · : förening, utvald frän gruppen som bestär av 3- (a-cyklopropylbensyl)-4-hydroxi-6-metyl-2H-pyran-2-on, och 4- hydroxi-6-metyl-3-(3-fenyl-prop-2-enyl)-2H-pyan-2-on. r*: 30 • · · *. 5. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en • · · *·|·* förening, utvald frän gruppen som bestär av *...* dimetyl 3-(4-hydroxi-2-oxo-6-fenyl-2H-l-pyran-3-yl)(4-nitrofenyl)-l,3-propandioat; ·:··· dimetyl 3-(4-hydroxi-2-oxo-6-fenyl-2H-1 -pyran-3-yl)(3-nitrofenyl)-1,3-propandioat; ....: 35 6-etyl-3 -(a-etylbensyl)-6-fenyl-tetrahydropyran-2,4-dion; 260 5.6- dihydro-4-hydroxi-6-cyklohexyl-6-fenyl-3-[l-(3-hydroxifenyl)propyl]-2H-pyran- 2- on; 4-hydroxi-l-oxa-3-(l-fenylpropyl)spiro-[5.5]undek-3-en-2-on, natriumsalt; 6.6- dietyl-3-(3-fenylpropyl)-tetrahydropyran-2,4-dion; 5 dihydro-6-metyl-6-fenyl-3-( 1 -fenyl-2-propenyl)-2H-pyran-2,4-(3H)-dion; dihydro-3-(l-(3-hydroxifenyl)propyl-6-fenyl-6-propyl-2H-pyran-2,4-(3H)-dion; 5.6- dihydro-4-hydroxi-6-fenyl-6-propyl-3-(l-fenylpropyl)-2H-pyran-2-on; 5.6- dihydro-4-hydroxi-6-fenyl-6-propyl-3-[l-(3-hydroxifenyl)propyl]-2H-pyran-2-on; 10 12-hydroxi-l 1-( 1 -fenyl-allyl)-1,4,9-trioxa-dispiro[4.2.5.2]pentadek-11 -en-10-on; 12-hydroxi-l 1-( 1 -fenyl-propyl)-1,4,9-trioxa-dispiro[4.2.5.2]pentadek-11 -en-10-on; 4-hydroxi-3-( 1 -fenylpropyl)-1 -oxa-spiro-[5,5]-undek-3-en-2,9-dion, 6.6- dibensyl-4-hydroxi-3-( 1 -fenyl-propyl)-5,6-dihydro-pyran-2-on; 4-hydroxi-3-( 1 -fenyl-allyl)-1,9-dioxa-spiro-[5,5]-undek-3-en-2-on, 15 4,9-dihydroxi-3-(l -fenyl-propyl)-1 -oxa-spiro-[5,5]-undek-3-en-2-on, 5.6- dihydro-4-hydroxi-6-fenyl-6-(fenylmetyl)-3-(l-fenyl-2-propenyl)-2H-pyran-2-on; 5.6- dihydro-4-hydroxi-6-fenyl-6-(fenylmetyl)-3-( 1 -fenylpropyl)-2H-pyran-2-on; 3- ( 1,3-difenyl-2-propenyl)-5,6-dihydro-4-hydroxi-6-(2-fenyletyl)-6-propyl-, (E)-2H- 20 pyran-2-on; .·. : 3-(l,3-difenyl-2-propyl)-5,6-dihydro-4-hydroxi-6-(2-fenyletyl)-6-propyl-, (E)-2H- • ·· pyran-2-on; ..*** 3-( 1,3-difenyl-2-propenyl)-5,6-dihydro-4-hydroxi-6-fenyl-6-(fenylmetyl-2H-pyran-2- * ·* on; ]· 25 3-(l,2-difenyletenyl)-5,6-dihydro-4-hydroxi-6-(2-fenyletyl)-6-propyl-, (E)-2H-pyran- :.: : 2-on; • · · : 5,6-dihydro-4-hydroxi-6-(2-fenyletyl)-3-(l-fenyl-2-propenyl)-6-propyl-2H-pyran-2- on; 5.6- dihydro-4-hydroxi-6-(2-fenyletyl)-3-(l-fenylpropyl)-6-propyl-2H-pyran-2-on; .***; 30 3-( 1,3-difenyl-2-propenyl)-5,6-dihydro-4-hydroxi-6-(fenylmetyl)-6-propyl-2H- • · · ·. pyran-2-on; • · · *· j·* 3-(1,3-difenylpropyl)-5,6-dihydro-4-hydroxi-6-(fenylmetyl)-6-propyl-2H-pyran-2- • · on; ·;··· 4-hydroxi-3-(l-fenylallyl)-l-oxa-spiro[5.6]-dodek-3-en-2-on, ....: 35 4-hydroxi-3-(l -fenylallyl)-1 -oxa-spiro[5.4]-dek-3-en-2-on, 7-bensyl-4-hydroxi-3-( 1 -fenylallyl)-1 -oxa-spiro[5.5]-undek-3-en-2-on, 261 4-hydroxi-3-( 1 -fenylpropyl)- l-oxa-spiro[5.4]-dek-3-en-2-on, 4-hydroxi-3-( 1 -fenyl-2-propenyl)-1 -oxaspiro[5.7]tridek-3-en-2-on, 4-hydroxi-3-( 1 -fenylpropyl)- l-oxaspiro[5.7]tridek-3-en-2-on, 6-butyl-5,6-dihydro-3-(l,3-difenyl-2-propenyl)-4-hydroxi-6-fenylmetyl-2H-pyran-2-5 on; 6-butyl-5,6-dihydro-3-(l,3-difenylpropyl)-4-hydroxi-6-fenylmetyl-2H-pyran-2-on; 6-butyl-5,6-dihydro-4-hydroxi-6-fenylmetyl-3-(l-fenyl-2-propenyl)-2H-pyran-2-on; 6-butyl-5,6-dihydro-4-hydroxi-6-fenylmetyl-3-(l-fenylpropyl)-2H-pyran-2-on; 3 -(a-cyklopropyl-[5-(metoximetoxi-metyl)-tiofen-2-yl]-metyl)-5,6-dihdydro-4-10 hydroxi-6-(2-metylpropyl)-6-(2-fenyletyl)-2H-pyran-2-on; 5.6- dihydro-4-hydroxi-6-(2-metylpropyl)-6-(2-fenyletyl)-3-(l-fenyl-2-propenyl)-2H-pyran-2-on; 5.6- dihydro-4-hydroxi-6-(2-metylpropyl)-6-(2-fenyletyl)-3-(l-fenylpropyl)-2H-pyran-2-on; 15 5,6-dihydro-3-difenylmetyl-4-hydroxi-6,6-di-(2-fenyletyl)-2H-pyran-2-on; 5.6- dihydro-4-hydroxi-6,6-di-(2-fenyletyl)-3-(l,3-difenyl-2-propenyl)-2H-pyran-2- on; 5.6- dihydro-4-hydroxi-6,6-di-(2-fenyletyl)-3-( 1,3-difenylpropyl)-2H-pyran-2-on; 5.6- dihydro-4-hydroxi-3-(l,3-difenyl-2-propenyl)-6-(3-fenylpropyl)-6-propyl-2H-20 pyran-2-on; ... ; 5,6-dihydro-4-hydroxi-3-(l,3-difenylpropyl)-6-(3-fenyIpropyl)-6-propyI-2H-pyran-2- • · · !..* on; • · ]; · · * 3 -(α-cyklopropyl- [ 5-(metoximetoxi-metyl)-tiofen-2-yl]-metyl)- 5,6-dihydro-4- • · · :' ·* hydroxi-6-(2-fenyletyl)-6-propyl-2H-pyran-2-on; :. : 25 3-(α-cyklopropyl- [ 5-(metoximetoxi-metyl)-tiofen-2-yl] -metyl)-5,6-dihydro-4- • · :.: · hydroxi-6-(3-fenylpropyl)-6-propyl-2H-pyran-2-on; :.: : 5,6-dihydro-3-difenylmetyl-4-hydroxi-6-(3-fenylpropyl)-6-propyl-2H-pyran-2-on; 3-difenylmetyl-5,6-dihydro-4-hydroxi-6-(2-metylpropyl)-6-(2-fenyletyl)-2H-pyran- 2-on; .··*. 30 3-(l,3-difenyl-2-propenyl)-5,6-dihydro-4-hydroxi-6-(2-metylpropyl)-6-(2-fenyletyl)- *·[ 2H-pyran-2-on; och *·:·* 3-( 1,3-difenyl-2-propyl)-5,6-dihydro-4-hydroxi-6-(2-metylpropyl)-6-(2-fenyletyl)- • · · 2H-pyran-2-on. • ♦ ....: 35 • · 262
6. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en förening, utvald frän gruppen som bestär av N-(3-cyklopropyl-[6-(l-etyl-fenetyl)-4-hydroxi-2-oxo-2H-pyran-3-yl]-metyl)-fenyl)- 3-(tert-butyloxikarbonylamino)-propionamid;
5 N-(3- {cyklopropyl-[6-(2-cyklopropyl-1 -cyklopropylmetyl-etyl)-4-hydroxi-2-oxo-2H- pyran-3-yl]-metyl} -fenyl)-3-indol-1 -yl-propionamid; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(l-(tetrahydro-furan-3-ylmetyl)-propyl)- pyran-2-on; 6-(l-(5-klor-tiofen-2-ylmetyl)-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-10 2-on; 3-(cyklopropyl-fenyl-metyl)-6-(l-(3,5-dimetyl-isoxazol-4-ylmetyl)-propyl)-4- hydroxi-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(l-(tetrahydro-furan-2-ylmetyl)-propyl)- pyran-2-on; 15 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(l-(tiofen-(2-ylmetyl)-propyl)-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(l-(tetrahydro-pyran-4-ylmetyl)-propyl)-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-6-(l-furan-2-ylmetyl-propyl)-4-hydroxi-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-6-( 1 -(1,3)dioxolan-2-ylmetyl-propyl)-4-hydroxi-pyran-20 2-on; #e . 3-(cyklopropyl-fenyl-metyl)-6-( 1 -tetrahydro-pyran-3-ylmetyl)-propyl)-pyran-2-on; • · · * 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-[ 1 -(tetrahydro-pyran-2-ylmetyl)-propyl]- ];·;* pyran-2-on; • · · ^ ·* 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-( 1 -pyridin-2-ylmetyl-propyl)-pyran-2-on; :.**i 25 6-(4-klor-l-etyl-butyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; • · ·.· · 6-(3-klor-l-etyl-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; :T: 3-(cyklopropyl-fenyl-metyl)-6-[etyl-3-(tetrahydro-pyran-2-yloxi)-propyl]-4-hydroxi- pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(l-pyridin-3-ylmetyl-propyl)-pyran-2-on; .···. 30 3-(cyklopropyl-fenyl-metyl)-6-l-etyl-(3-tiofen-3-yl-propyl)-4-hydroxi-pyran-2-on; ’·[ 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-[l-(tetrahydro-pyran-3-ylmetyl)-butyl]- *·ί·* pyran-2-on; ··» 5-brom-6-(2-cyklopropyl-cyklopropylmetyl-etyl)-4-hydroxi-3-( 1 -fenyl-propyl)-pyran-2-on; : 35 3-( 1 -bensyl-2-fenyl-etyl)-6-(2-cyklopropyl-1 -cyklopropylmetyl-etyl)-4-hydroxi- • · pyran-2-on; 263 6-(2-cyklopropylmetyl-etyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi- pyran-2-on; 6-(l-allyl-but-3-enyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-6-(l-etyl-3-(2-metoxi-etoxi)-propyl)-4-hydroxi-pyran-2- on; 5 6-( 1 -bensyl-3-(2-metoxi-etoxi)-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi- pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-p-hydroxifenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(P-hydroxi-p-metylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(P-hydrofi-p-fluorfenetyl)-2H-pyran-2-on; 10 3-(a-cyklopropylbensyl)-4-hydroxi-6-(P-hydroxi-p-klorfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(P-hydroxi-m-klorfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(P-hydroxi-o-klorfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(2-(furan-3-yl)-2-hydroxietyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(2-(tiofen-3-yl)-2-hydroxietyl)-2H-pyran-2-on; 15 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-p-fluorfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-p-klorfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-m-klorfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-o-klorfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-p-bromfenetyl)-2H-pyran-2-on; 20 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-m-bromfenetyl)-2H-pyran-2-on; . 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-p-trifluormetylfenetyl)-2H-pyran-2-on; • · · !..* 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-m-trifluormetylfenetyl)-2H-pyran-2-on; ];·;* 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-o-trifluormetylfenetyl)-2H-pyran-2-on; ^ ·* 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-p-metoxifenetyl)-2H-pyran-2-on; 25 3-(a-cyklopropylbensyl)-4-hydroxi-6-(a-etyl-m-metoxifenetyl)-2H-pyran-2-on; • · 3 -(a-cyklopropylbensyl)-4-hydroxi-6-(p-fluorfenetyl)-2H-pyran-2-on; :j: 3-(a-cyklopropylbensyl)-4-hydroxi-6-(p-klorfenetyl)-2H-pyran-2-on; 3-(a-cyklopropylbensyl)-4-hydroxi-6-(p-bromfenetyl)-2H-pyran-2-on; 3-(cyklopropylfenylmetyl)-6-[ 1 -etyl-3(4-morfolinyl)propyl]-4-hydroxi-2H-pyran-2-.···. 30 on; ’·’ 3-(cyklopropylfenylmetyl)-P-etyl-4-hydroxi-2-oxo-, fenylmetylester 2H-pyran-6- • · · *«·* propansyra; 3-(cyklopropylfenylmetyl)-4-hydroxi-6-[2-metyl-1 -(fenylmetyl)propyl]-2H-pyran-2- « ....: on; • · * ....: 35 3-( cyklopropylfenylmetyl)-4-hydroxi-6-[2-metyl-l-[(tetrahydro-2H-pyran-3- • · (yl)]metyl)propyl]-2H-pyran-2-on; 264 4-hydroxi-3-( 1 -fenylpropyl)-6-[ 1 -[(tetrahydro-2H-pyran-3-yl)metyl]propyl-2H-pyran-2-on; 3-(cyklopropylfenylmetyl)-6-(l-etyl-4,4,4-trifluorbutyl)-4-hydroxi-pyran-2-on; 3-[2-[3-(cyklopropylfenylmetyl)-4-hydroxi-2-oxo-2H-pyran-6-yl]butyl]-l-[(4-5 metylfenyl)sulfonyl]-piperidin; 2- [2-[3-(cyklopropylfenylmetyl)-4-hydroxi-2-oxo-2H-pyran-6-yl]butyl]-l-[(4-metylfenyl)sulfonyl]-pyirolidin; 3- (cyklopropylfenylmetyl)-4-hydroxi-6-(3,3,3-trifluorpropyl)-2H-pyran-2-on; 2- [2-[3-(cyklopropylfenylmetyl)-4-hydroxi-2-oxo-2H-pyran-6-yl]butyl]-l-[(4-10 metylfenyl)sulfonyl]-piperidin; 4- [2-[3-(cyklopropylfenylmetyl)-4-hydroxi-2-oxo-2H-pyran-6-yl]butyl]-l-[(4-metylfenyl)sulfonyl]-piperidin; 4-[2-[3-(cyklopropylfenylmetyl)-4- hydroxi-2-oxo-2H-pyran-6-yl]butyl]-1 -(fenylmetyl)-2-pyrrolidinon; 15 6-(cyklopentylmetyl)-3 -(cyklopropylfenylmetyl)-4-hydroxi-2H-pyran-2-on; 3- (cyklopropylfenylmetyl)-4-hydroxi-6-[(tetrahydro-2H-pyran-4-yl)metyl]-2H-pyran-2-on; 3- (cyklopropylfenylmetyl)-6-(3-fluorpropyl)-4-hydroxi-2H-pyran-2-on; 4- hydroxi-3-( 1 -fenylcyklobutyl)-6-[ 1 -(fenylmetyl)propyl]-2H-pyran-2-on; 20 3-(a-etylbensyl)-6-(a-etylbensyl)-4-hydroxi-2H-pyran-2-on; ,, ; 3-(a-cyklopropyl-meta-[(fenylaminokarbonyl)amino]bensyl)-6-(a-etylfenetyl)-4- • · · I..* hydroxi-2H-pyran-2-on; • · .;1* * 3 -(α-cyklopropyl-meta- [(4-metoxifenylaminokarbonyl)amino]bensyl)-6-(a-etyl- • · · \ ·[ fenetyl)-4-hydroxi-2H-pyran-2-on; • · · *· " 25 3-(a-cyklopropyl-meta-[(bensylaminokarbonyl)amino]bensyl)-6-(a-etylfenetyl)-4- :.: : hydroxi-2H-pyran-2-on; • · · :.: : 3 -(α-cyklopropyl-meta- [(4-bromfenylaminokarbonyl)amino]bensyl)-6-(a-etyl- fenetyl)-4-hydroxi-2H-pyran-2-on; :*·*: 3-(a-cyklopropyl-meta-[(fenylsulfonylaminokarbonyl)amino]bensyl)-6-(a- .**·. 30 etylfenetyl)-4-hydroxi-2H-pyran-2-on; • « · ·. 3-(a-cyklopropyl-meta-(N-a-tert-butyloxikarbonyl-N-im-p-toluensulfonyl-L- • · · ’·"* histidylamino)bensyl)-6-(a-etyl-fenetyl)-4-hydroxi-2H-pyran-2-on; :... * 3-(a-cyklopropyl-meta-(tert-butyloxikarbonyl-L-alanylamino)bensyl)-6-(a-etyl- •: · · * fenetyl)-4-hydroxi-2H-pyran-2-on; ....: 35 3 -(a-cyklopropyl-meta-(4-bromfenylbensoylamino)bensyl)-6-(a-etylfenetyl)-4- hydroxi-2H-pyran-2-on; 265 3-(a-cyklopropyl-meta-(N-a-tert-butyloxikarbonyl-L-histidylamino)bensyl)-6-(a- etylfenetyl)-4-hydroxi-2H-pyran-2-on; 3 -(a-cyklopropyl-meta-(N-bensyloxikarbonyl-O-a-bensyl-L-glutamylamino)bensyl)-6-(a -etylfenetyl)-4-hydroxi-2H-pyran-2-on; 5 3-(a-cyklopropyl-meta-(4-cyanofenylbensoylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(L-glutamylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H- pyran-2-on; 3-(a-cyklopropyl-meta-(3-(l-indolyl)propanoylamino)bensyl)-6-(a-etylfenetyl)-4-10 hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(2-pyridylacetylammo)bensyl)-6-(a-etylfenetyl)-4-hydroxi- 2H-pyran-2-on; 3-(a-cyklopropylbensyl)-6-[l-cyklopropylmetyl-2-(tetrahydropyran-3-yl)etyl]-4- hydroxi-2H-pyran-2-on; 15 3-(a-cyklopropyl-meta-(3-pyridylacetylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; och 3-(a-cyklopropyl-meta-(4-pyridylacetylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi- 2H-pyran-2-on. 20 7. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en : forening, utvald frän gruppen som bestär av • ·· 3-(a-cyklopropyl-meta-(fenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H- pyran-2-on; • · · \ 3-(a-cyklopropyl-meta-(propylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi- *· 25 2H-pyran-2-on; :.:: 3 -(a-cyklopropyl-meta-((E)-2-fenyletenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4- *·« V ; hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(4-bromfenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4- hydroxi-2H-pyran-2-on; ·***: 30 3-(a-cyklopropyl-meta-(2,5-diklorfenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4- • · · *, hydroxi-2H-pyran-2-on; • · · *”·* 3-(a-cyklopropyl-meta-(4-tert-butylfenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4- hydroxi-2H-pyran-2-on; ·:··: 3-(a-cyklopropyl-meta-(4-cyanofenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4- ....: 35 hydroxi-2H-pyran-2-on; 266 3-(a-cyklopropyl-meta-(4-metoxifenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4- hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(4-klorfenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4- hydroxi-2H-pyran-2-on; 5 3-(a-cyklopropyl-meta-(8-kinolinsulfonylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(etylsulfonylamino)bensyl)-6-[l-cyklopropylmetyl-2-(tetrahydropyran-3 -yl)etyl] -4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(4-metylfenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4-10 hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(4-metylfenylsulfonylamino)bensyl)-6-[l-cyklopropylmetyl- 2- (tetrahydropyran-3-yl)etyl]-4-hydroxi-2H-pyran-2-on; 3- (a-cyklopropyl-meta-(etylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 15 3-(a-cyklopropyl-meta-(4-fluorfenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(bensotiadiazolyl-sulfonylamino)bensyl)-6-(a-etylfenetyl)-4- hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(benso-oxodiazolyl-sulfonylamino)bensyl)-6-(a-etylfenetyl)-20 4-hydroxi-2H-pyran-2-on; <. > . 3-(a-cyklopropyl-meta-(( 1 -metyl-imidazol-4-yl)-sulfonylamino)bensyl)-6-(a- ·„* etylfenetyl)-4-hydroxi-2H-pyran-2-on; • · 3-(a-cyklopropyl-meta-((pyridin-3-yl)-sulfonylamino)bensyl)-6-(a-etylfenetyl)-4- • · · ! ·* hydroxi-2H-pyran-2-on; 25 3-(a-cyklopropyl-meta-(5-(pyridin-2-yl)-tiofen-2-yl-sulfonylamino)bensyl)-6-(a- • · :.: · etylfenetyl)-4-hydroxi-2H-pyran-2-on; : T: 3 -(a-cyklopropyl-meta-(4-hydroxiaminofenylsulfonylamino)bensyl)-6-(a- etylfenetyl)-4-hydroxi-2H-pyran-2-on; . : . 3 -(a-cyklopropyl-meta-(4-dimetylaminofenylsulfonylamino)bensyl)-6-(a- .···. 30 etylfenetyl)-4-hydroxi-2H-pyran-2-on; *·[ 3-(a-cyklopropyl-meta-(3-aminofenylsulfonylamino)bensyl)-6-(a-etylfenetyl)-4- hydroxi-2H-pyran-2-on; ··· 3-(a-cyklopropyl-meta-(4-aminokarbonylfenylsulfonylamino)bensyl)-6-(a-....: etylfenetyl)-4-hydroxi-2H-pyran-2-on; ....: 35 3 -(a-cyklopropylbensyl)-6-(a-etyl-fenylsulfonylaminometyl)-4-hydroxi-2 H-pyran-2- • · on; 267 3-(a-cyklopropylbensyl)-6-(l-etyl-2-fenylsulfonylammo-etyl)-4-hydroxi-2H-pyran- 2- on; 3- (a-cyklopropyl-meta-(4-fluorfenylsulfonylamino)bensyl)-6-(a-etyl-fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; 5 3-(a-cyklopropyl-meta-(fenylsulfonylamino)bensyl)-6-(a-etyl-fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(2,5-diklorfenylsulfonylamino)bensyl)-6-(a-etyl-fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(4-cyanofenylsulfonylamino)bensyl)-6-(a-etyl-10 fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(kinolin-8-yl-sulfonylamino)bensyl)-6-(a-etyl- fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-((2-fenyletenyl)-sulfonylamino)bensyl)-6-(a-etyl- fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; 15 3-(a-cyklopropyl-meta-(( 1 -metyl-imidazo-4-yl)-sulfonylamino)bensyl)-6-(a-etyl-fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(pyridin-3-yl-sulfonylamino)bensyl)-6-(a-etyl-fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; 3-(a-cyklopropyl-meta-(4-dimetylamino-fenylsulfbnylamino)bensyl)-6-(a-etyl- 20 fenylsulfonylaminometyl)-4-hydroxi-2H-pyran-2-on; •t . 3-(a-cyklopropyl-meta-(4-fluorfenylsulfonylamino)bensyl)-6-( 1 -etyl-2- • · · I.. * fenylsulfonylamino-etyl)-4-hydroxi-2H-pyTan-2-on; 3-(a-cyklopropyl-meta-(fenylsulfonylamino)bensyl)-6-( 1 -etyl-2-fenylsulfonylamino- ♦ ♦ · : ·] etyl)-4-hydroxi-2H-pyran-2-on; *. **: 25 3-(a-cyklopropyl-meta-(2,5-diklorfenylsulfonylamino)bensyl)-6-( 1 -etyl-2- • · :.: · fenylsulfonylamino-etyl)-4-hydroxi-2H-pyran-2-on; • · · v : 3-(a-cyklopropyl-meta-(4-cyanofenylsulfonylamino)bensyl)-6-( 1 -etyl-2- fenylsulfonylamino-etyl)-4-hydroxi-2H-pyran-2-on; :*·*: 3-(a-cyklopropyl-meta-(kinolin-8-yl-sulfonylamino)bensyl)-6-(l-etyl-2- .*··. 30 fenylsulfonylamino-etyl)-4-hydroxi-2H-pyran-2-on; • · · ·. 3-(a-cyklopropyl-meta-((2-fenyletenyl)-sulfonylamino)bensyl)-6-(l-etyl-2- • · · *·|·* fenylsulfonylamino-etyl)-4-hydroxi-2H-pyran-2-on; :...: 3-(a-cyklopropyl-meta-(( 1 -metyl-imidazo-4-yl)-sulfonylamino)bensyl)-6-( 1 -etyl-2- ·;··.’ fenylsulfonylamino-etyl)-4-hydroxi-2H-pyran-2-on; ....: 35 3-(a-cyklopropyl-meta-(pyridin-3-yl-sulfonylamino)bensyl)-6-(l-etyl-2- fenylsulfonylamino-etyl)-4-hydroxi-2H-pyran-2-on; och 268 3- (a-cyklopropyl-meta-(4-dimetylamino-fenylsulfonylamino)bensyl)-6-(l-etyl-2-fenylsulfonylamino-etyl)-4-hydroxi-2H-pyran-2-on.
8. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en 5 förening, utvald frän gruppen som bestär av: N-[5-[a[R]-cyklopropyl-a-[6-(a[R]-etyl-a[S]-tetrahydrofuran-2-ylmetyl)metyl-4- hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-cyklopropyl-a-[6-(a[R]-etyl-a[R]-tetrahydrofuran-2-ylmetyl)metyl-4- hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid;
10 N-[5-[a[R]-cyklopropyl-a-[6-(a[R]-etyl-a[S]-tetrahydrofiiran-2-ylmetyl)metyl-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-fluorfenylsulfonamid; N-[5-[a[R]-cyklopropyl-a-[6-(a[R]-etyl-a[R]-tetrahydrofuran-2-ylmetyl)metyl-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-fluorfenylsulfonamid; N-[5-[a[R]-cyklopropyl-a-[6-(l[S]-etyl-2[R]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-15 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-cyklopropyl-a-[6-(l[S]-etyl-2[R]-hydroxi-2-[R]tetrahydrofliran-2-yl)etyl- 4- hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-cyklopropyl-a-[6-(l[R]-etyl-2[S]-hydroxi-2-[S]tetrahydrofiiran-2-yl)etyl-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid;
20 N-[5-[a[R]-cyklopropyl-a-[6-(l[R]-etyl-2[S]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-., . 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-cyklopropyl-a-[6-( 1 [S]-etyl-2[S]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-];·;* 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; :t ·[ N-[5-[a[R]-cyklopropyl-a-[6-(l [S]-etyl-2[S]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl- *. **: 25 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; :.· · N-[5-[a[R]-cyklopropyl-a-[6-(l [R]-etyl-2[R]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl- : 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-cyklopropyl-a-[6-(l[R]-etyl-2[R]-hydroxi-2-[R]tetrahydrofuran-2- yl)etyl-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; .*··. 30 N-[5-[a[S]-cyklopropyl-a-[6-(l [S]-etyl-2[R]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl- " 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; *·:·* N-[5-[a[S]-cyklopropyl-a-[6-(l[S]-etyl-2[R]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl- 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[S]-cyklopropyl-a-[6-(l[R]-etyl-2[S]-hydroxi-2-[S]tetrahydroiuran-2-yl)etyI-....: 35 4-hydroxi-2-pyran-3 -yl] -metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; 269 N-[5-[a[S]-cyklopropyl-a-[6-(l[R]-etyl-2[S]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl- 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[S]-cyklopropyl-a-[6-(l[S]-etyl-2[S]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl- 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid;
5 N-[5-[a[S]-cyklopropyl-a-[6-(l[S]-etyl-2[S]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4-hydroxi-2-pyTan-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[S]-cyklopropyl-a-[6-(l[R]-etyl-2[R]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[S]-cyklopropyl-a-[6-(l[R]-etyl-2[R]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-10 4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; 3-(a[S]-cyklopropyl(5-(2-hydroxietyl)tiofen-2-ylmetyl)-6-(l[R]-etyl-2[R]tetrahydrofuran-2-yl)etyl-4-hydroxi-2H-pyran-2-on; 3-(a[S]-cyklopropyl(5-(2-hydroxietyl)tiofen-2-ylmetyl)-6-(a[R]-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 15 3-(a[S]-cyklopropyl(5-(2-hydroxietyl)tiofen-2-ylmetyl)-6-(a[R]-etyl-meta-hydroximetylfenetyl)-4-hydroxi-2H-pyran-2-on; 3-(a[S]-cyklopropyl(5-(2-hydroxietyl)tiofen-2-ylmetyl)-6-(a[R]-etyl-orto- hydroximetylfenetyl)-4-hydroxi-2H-pyran-2-on; 3- (a[S]-cyklopropyl(5-(l,2-dihydroxietyl)tiofen-2-ylmetyl)-6-(l[R]-etyl-2[R]- 20 tetrahydrofuran-2-yl)etyl-4-hydroxi-2H-pyran-2-on; . . : 3-(<x[S]-cyklopropyl(5-( 1,2-dihydroxietyl)tiofen-2-ylmetyl)-6-(a[R]-etylfenetyl)-4- • · · hydroxi-2H-pyran-2-on; . Π 3-(a[S]-cyklopropyl(5-( 1,2-dihydroxietyl)tiofen-2-ylmetyl)-6-(a[R]-etyl-meta- \ hydroximetylfenetyl)-4-hydroxi-2H-pyran-2-on; ]· 25 3-(a[S]-cyklopropyl(5-(l,2-dihydroxietyl)tiofen-2-ylmetyl)-6-(a[R]-etyl-orto- :.: : hydroximetylfenetyl)-4-hydroxi-2H-pyran-2-on; « · · : 3-(a[S]-cyklopropyl)-meta-(4-cyanofenylsulfonylamino)bensyl)-6-(a[R]-etylfenetyl- 4- hydroxi-2H-pyran-2-on; : : : 3 -(a[ S]-cyklopropyl)-meta-(4-cyanofenylsulfonylamino)bensyl)-6-(a[S]-etylfenetyl- 30 4-hydroxi-2H-pyran-2-on; ··· *. 3-(a[R]-cyklopropyl)-meta-(4-cyanofenylsulfonylamino)bensyl)-6-(a[S]-etylfenetyl- • · · 4-hydroxi-2H-pyran-2-on; 3-(a[R]-cyklopropyl)-meta-(4-cyanofenylsulfonylamino)bensyl)-6-(a[R]-etylfenetyl-·;·*: 4-hydroxi-2H-pyran-2-on; ....: 35 3-[( [R]-cyklopropylmetyl)(5-N-(p-fluorfenylsulfonyl)metyl)tiofenmerkapto-2-yl]-6- (a[R]-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 270 N-[5-[a[R]-ety]-a-[6-(a[R]-etyl-a[S]-tetrahydrofuran-2-ylmetyl)metyl-4-hydroxi-2- pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-etyl-a-[6-(a[R]-etyl-a[R]-tetrahydrofuran-2-ylmetyl)metyl-4-hydroxi-2- pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid;
5 N-[5-[a[R]-etyl-a-[6-(a[R]-etyl-a[S]-tetrahydrofuran-2-ylmetyl)metyl-4-hydroxi-2- pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-etyl-a-[6-(a[R]-etyl-a[R]-tetrahydrofuran-2-ylmetyl)metyl-4-hydroxi-2- pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-etyl-a-[6-(l[S]-etyl-2[R]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-4- 10 hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-etyl-a-[6-(l[S]-etyl-2[R]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4- hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-etyl-a-[6-(l[R]-etyl-2[S]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-4- hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid;
15 N-[5-[a[R]-etyl-a-[6-(l[R]-etyl-2[S]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4- hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-etyl-a-[6-(l[S]-etyl-2[S]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-4- hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-etyl-a-[6-(l[S]-etyl-2[S]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4- 20 hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; .·. : N-[5-[a[R]-etyl-a-[6-(l [R]-etyl-2[R]-hydroxi-2-[S]tetrahydrofijran-2-yl)etyl-4- • · · hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[R]-etyl-a-[6-(l[R]-etyl-2[R]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4- • · · *. ·’ hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; '· 25 N-[5-[a[S]-etyl-a-[6-(l[S]-etyl-2[R]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-4- :.: : hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; : N-[5-[a[S]-etyl-a-[6-(l[S]-etyl-2[R]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4- hydroxi'2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[a[S]-etyl-a-[6-(l[R]-etyl-2[S]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-4- 30 hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; ·. N-[5-[a[S]-etyl-a-[6-(l[R]-etyl-2[S]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4- • · · *;j·’ hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; *...* N-[5-[a[S]-etyl-a-[6-(l[S]-etyl-2[S]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-4- ·:··· hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; ....: 35 N-[5-[a[S]-etyl-a-[6-(l[S]-etyl-2[S]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4- hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; 271 N-[5-[a[S]-etyl-a-[6-(l[R]-etyl-2[R]-hydroxi-2-[S]tetrahydrofuran-2-yl)etyl-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid och N-[5-[a[S]-etyl-a-[6-(l[R]-etyl-2[R]-hydroxi-2-[R]tetrahydrofuran-2-yl)etyl-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid. 5
9. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en förening, utvald frän gruppen som bestar av: 3- (a-cyklopropyl-meta-(bensyloxikarbonylamino)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 10 3-(a-cyklopropyl-meta-(tert-butyloxikarbonylamino)bensyl)-6-(a-cyklopropylmetyl-cyklopropyletyl)-4-hydroxi-2H-pyran-2-on; 4- hydroxi-3-( 1 -fenyl-propyl)-6-( 1 -propyl-butyl)-pyran-2-on; 3-(5-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-oxo-6H-pyran-2-yl)-propionsyra-tert-butylester; 15 3-(cyklopropyl-fenyl-metyl)-6-(2-(3,5-dimetyl-isoxazol-4-yl)-etyl)-4-hydroxi-pyran- 2- on; 6-(2-(5-tert-butyl-(l,2,4)oxadiazol-3-yl)-etyl)-3-(cyklopropyl-fenyl-metyl)-4- hydroxi-pyran-2-on; 3- (cyklopropyl-fenyl-metyl)-4-hydroxi-6-(2-fenyl-l-pyridin-2-ylmetyl-etyl)-pyran-2- 20 on; .·. : 3-(cyklopropyl-fenyl-metyl)-6-(2-(l,3-dioxolan-2-yl-etyl)-4-hydroxi-pyran-2-on; • · · # *.. \ 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(4-morfolin-4-yl-butyl)-pyran-2-on; • · 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(2-pyridin-2-yl-etyl)-pyran-2-on; *. \ 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(2-(2-metyl-tiazol-4-yl)-etyl)-pyran-2-on; • · · 25 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(2-kinolin-2-yl-etyl)-pyran-2-on; :.: : 6-(3-klor-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; * ♦ · :.Σ : 6-( 1 -(2-(4-klor-fenyl)-tiazol-4-ylmetyl)-propyl)-3-(cyklopropyl-fenyl-metyl)-4- hydroxi-pyran-2-on; :T: 3-(cyklopropyl-fenyl-metyl)-6-(3-( 1,3-dioxan-2-yl-1 -etyl-propyl)-4-hydroxi-pyran-2- :**·: 30 on; ··· *. 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-( 1 -pyridin-4-ylmetyl-propyl)-pyran-2-on; • · · 3- (cyklopropyl-fenyl-metyl)-6-( 1 -etyl-3-morfolin-4-yl-3-oxo-propyl)-4-hydroxi- • ♦ *·♦·* pyran-2-on; •: · ·: 3-(cyklopropyl-fenyl-metyl)-6-( 1 -etyl-4-morfolin-4-yl-butyl)-4-hydroxi-pyran-2-on; 35 3-(cyklopropyl-fenyl-metyl)-6-[ 1 -(2,3-dihydro-benso[ 1,4]dioxin-2-ylmetyl)propyl]- 4- hydroxi-pyran-2-on; 272 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-isobutyl-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-6-[l-(5,6-dihydro-2H-pyran-3-etyl)propyl]-4-hydroxi- pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-5-(2-(2-metoxi-etoxi)etyl)-6-propyl-pyran-2-5 on; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(l-isobutyl-3-metyl-butyl)-pyran-2-on; 3 -dicyklopropylmetyl-4-hydroxi-6-fenetyl-pyran-2-on, 6-( 1 -cyklopropyl-etyl)-3-dicyklopropylmetyl-4-hydroxi-pyran-2-on; 6-(1 -cyklopropyl-1 -cyklopropylmetyl-etyl)-3-dicyklopropylmetyl-4-hydroxi-pyran-10 2-on; 6-(l-cyklohexylmetyl-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; 6-(l-bensyl-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; 6-(2-cyklopropyl-1 -cyklopropylmetyl-etyl)-4-hydroxi-3-( 1 -fenyl-propyl)-pyran-2-on; 15 6-(1 -bensyl-2-cyklopropyl-etyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; 6-(2-cyklopropyl-etyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; 6-(l-cyklopropylmetyl-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(4-fenyl-butyl)-pyran-2-on; 3-(cyklohexyl-cyklopropyl-metyl)-6-(2-cyklopropyl-l-cyklopropylmetyl-etyl)-4-20 hydroxi-pyran-2-on; . . : 3 -(cyklopropyl-fenyl-metyl)-6-( 1 -etyl-4-fenyl-butyl)-4-hydroxi-pyran-2-on; 6-(3-cyklohexyl-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; • · . ΓI 6-(3-cyklohexyl-1 -etyl-propyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; *. \ 6-(2-cyklopropyl-etyl)-4-hydroxi-3-( 1 -fenyl-propyl)-pyran-2-on; • · · / / 25 6-but-3-enyl-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-pyran-2-on; • · · ' 3-(cyklopropyl-fenyl-metyl)-6-( 1 -etyl-3-fenyl-propyl)-4-hydroxi-pyran-2-on; ··· ; : 5-brom-6-(2-cyklopropyl-etyl)-4-hydroxi-3-( 1 -fenyl-propyl)-pyran-2-on; 6-( 1 -bensyl-2- fenyl-etyl)-4-hydroxi-3-( 1 -fenyl-propyl)-pyran-2-on; :T: 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(3-(2-metoxi-etoxi)-propyl)-pyran-2-on; : 30 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-5-(2-(2-metoxi-etoxi)etyl)-6-(3-(2-metoxi- ··· etoxi)-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-propyl-pyran2-on; '···' 5-brom-4-hydroxi-6-fenyletyl-(3-( 1 -fenyl-propyl)-pyran-2-on; ·:·*: 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(3-(2-metoxi-etoxi)-etoxi)-propyl)-pyran-2- ·:♦·: 35 on; 5-brom-4-hydroxi-3-( 1 -fenyl-propyl)-6-propyl-pyran-2-on; 273 3-(cyklopropyl-fenyl-metyl)-6-(l-etyl-propyl)-4-hydroxi-5-(2-(2-metoxi-etoxi)-etyl)- pyran-2-on; 6-( 1 -bensyl-propyl)-5-brom-4-hydroxi-3-( 1 -fenyl-propyl)-pyran-2-on; 6-(2-cyklopropyl-l-cyklopropylmetyl-etyl)-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-5 5-(2-(2-metoxi-etoxi-etoxi)-etyl)-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-6-(2-furan-2-yl-2-hydroxi-etyl)-4-hydroxi-pyran-2-on; 3-(cyklopropyl-fenyl-metyl)-4-hydroxi-6-(4,4,4-trifluor-butyl)-pyran-2-on; 6-[2-(l-cyklohexyl-lH-tetrazol-5-yl)-etyl]-3-(cyklopropyl-fenyl-metyl)-4-hydroxi-2-on; och 10 4-hydroxi-3-( 1 -fenyl-propyl)-1 -oxa-spiro[5.5]undek-3-en-2,9-dion monooxim.
10. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en förening, utvald frän gruppen som bestär av 3-([R]-a-etylbensyl)-4-hydroxi-6-([R]-a-etylfenetyl)-2H-pyran-2-on; 15 3-([R]-a-etylbensyl)-4-hydroxi-6-([S]-a-etylfenetyl)-2H-pyran-2-on; 3-([S]-a-etylbensyl)-4-hydroxi-6-([R]-a-etylfenetyl)-2H-pyran-2-on; 3-([S]-a-etylbensyl)-4-hydroxi-6-([S]-a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-metoximetylhydroximetyleter)ftirfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 20 3-(a-cyklopropyl((5-hydroximetyl)furftir-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H- . pyran-2-on; • · · l..' 3-(a-cyklopropyl((5-metoximetyl)furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H- pyran-2-on; • · · • ·] 3-(a-cyklopropyl((5-azidometyl)flirfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran- 25 2-on; • · :.:: 3-(a-cyklopropyl((5-aminometyl)furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran- ·* 2-on; 3-(a-cyklopropyl((5-[N-acetyl]aminometyl)furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-:*·*: 2H-pyran-2-on; . · · *. 30 3-(a-cyklopropyl(( 5 - [N-fenylsulfonyl]aminometyl)furfur-2-yl))-4-hydroxi-6-(a- • · · ·. etylfenetyl)-2H-pyran-2-on; • · · *”·’ 3-(a-cyklopropyl((5-[N-(o-fluor)fenylsulfonyl]aminometyl)furfur-2-yl))-4-hydroxi-6- :... * (a-etylfenetyl)-2H-pyran-2-on; ·;··: 3-(a-cyklopropyl((5-[N-(p-fluor)fenylsulfonyl]aminometyl)furfur-2-yl))-4-hydroxi-6- ....: 35 (a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-[N-(m-fluor)fenylsulfonyl]aminometyl)flirflir-2-yl))-4-hydroxi- 6-(a-etylfenetyl)-2H-pyran-2-on; 274 3-(a-cyklopropyl((5-[N-(m-fluor)fenylsulfonyl]aminometyl)ftirilir-2-yl))-4-hydroxi- 6-(a-etylfenetyl)-2H-pyran-2-on; 5 3-(a-cyklopropyl((5-[N-(o-cyano)fenylsulfonyl]aminometyl)furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-[N-(p-cyano)fenylsulfonyl]aminometyl)furfur-2-yl))-4-hydroxi- 6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-[N-(m-cyano)fenylsulfonyl]aminometyl)furfur-2-yl))-4-hydroxi-10 6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-[N-(m-cyano)fenylsulfonyl]aminometyl)furiiir-2-yl))-4-hydroxi- 6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-(4-karboetoxi-1,2,3-triazol- l-yl)metyl)furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 15 3-(a-cyklopropyl((5-(4-karboxylsyra-l,2,3-triazol-l-yl)metyl)furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-(N-(l-nitro-2-metyltioeten-2-yl)aminometyl)furfur-2-yl))-4- hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-(N-(l-nitro-2-[N-isopropyl]eten-2-yl)aminometyl)furfur-2-yl))- 20 4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; : 3-(a-cyklopropyl((5-(N-(N-cyano, metyltioimino)aminometyl)furfur-2-yl))-4- . ···] hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; • · .’.’l' 3-(a-cyklopropyl((5-(N-(N-cyano, N,-isopropylguanidin)aminometyl)furfur-2-yl))-4- \ hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; • · · / '· 25 3-(a-cyklopropyl((5-(N-bensylkarbamat)aminometyl)furfiir-2-yl))-4-hydroxi-6-(a- '··'· : etylfenetyl)-2H-pyran-2-on; ··· : 3- (a-cyklopropyl((5-bensylkarbamat)aminometyl)tiofen-2-ylmetyl))-4-hydrroxi-6-( a-etylfenetyl)-2H-pyran-2-on; :T: 3-(a-cyklopropyl((5-aminometyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H- 30 pyran-2-on; ♦ ♦♦ ^ \ 3-(a-cyklopropyl((5-(N-fenylsulfonyl)aminometyl)tiofen-2-ylmetyl))-4-hydroxi-6- (a-etylfenetyl)-2H-pyran-2-on; • * '···* 3-(a-cyklopropylfurfur-2-yl)-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; *:·*: 3-(a-cyklopropyl(5-N-fenylsulfonyl)furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H- *:**: 35 pyran-2-on; 275 3-(a-cyklopropyl((5-metoximetylhydroximetyleter)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on); 3-(a-cyklopropyl((5-hydroximetyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)- 2H-pyran-2-on; 5 3-(a-cyklopropyl((5-metoximetyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-azidometyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H- pyran-2-on; 3-(a-cyklopropyl((5-aminometyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H-10 pyran-2-on; 3-(a-cyklopropyl((5-[N-acetyl]aminometyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a- etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-[N-fenylsulfonyl]aminometyl)tiofen-2-ylmetyl))-4-hydroxi-6- (a-etylfenetyl)-2H-pyran-2-on; 15 3-(a-cyklopropyl((5-(4-karboetoxi-1,2,3-triazol-1 -yl)metyl)tiofen-2-ylmetyl))-4- hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-(4-karboxylsyra-1,2,3-triazol-1 -yl)metyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl((5-(N-(l-nitro-2-metyltioeten-2-ylmetyl)aminometyl)tiofen-2-yl))- 20 4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; ;\j 3-(a-cyklopropyl((5-(N-(l-nitro-2-[N-isopropyl])eten-2-yl)aminometyl)tiofen-2- ,···’ ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; • · 3 -(a-cyklopropyl((5-(N-(N-cyano, metyltioamino)aminometyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on); • · · [· " 25 3-(a-cyklopropyl((5-(N-(N-cyano, N’isopropylguanidin)aminometyl)tiofen-2- :>i : ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on); ··· : 3-(a-cyklopropyltiofen-2-ylmetyl)-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on); 3-(a-cyklopropyl(5-(N-fenylsulfonyl)tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-:T: 2H-pyran-2-on; 30 3-(a[S]-etylbensyl)-4-hydroxi-6-(a[R]-etyl-P[S]-hydroxifenetyl)-2H-pyran-2-on; *. 3-(a[S]-etylbensyl)-4-hydroxi-6-(a[S]-etyl-6[Rl-hydroxifenetyl)-2H-pyran-2-on; ♦ · ♦ *·|·* 3-(a[S]-etylbensyl)-4-hydroxi-6-(a[R]-etyl-p[R]-hydroxifenetyl)-2H-pyran-2-on; *···* 3-(a[S]-etylbensyl)-4-hydroxi-6-(a[S]-etyl-P[S]-hydroxifenetyl)-2H-pyran-2-on; ·:··· 3-(a[R]-etylbensyl)-4-hydroxi-6-(a[R]-etyl-P[S]-hydroxifenetyl)-2H-pyran-2-on; ..: 35 3-(a[R]-etylbensyl)-4-hydroxi-6-(a[S]-etyl-P[R]-hydroxifenetyl)-2H-pyran-2-on; 3-(a[R]-etylbensyl)-4-hydroxi-6-(a[R]-etyl-P[R]-hydroxifenetyl)-2H-pyran-2-on; 276 3-(a[R]-etylbensyl)-4-hydroxi-6-(a[S]-etyl-P[S]-hydroxifenetyl)-2H-pyran-2-on; 3-(a[S]-cyklopropylbensyl)-4-hydroxi-6-(a[R]-etyl-P[S]-hydroxifenetyl)-2H-pyran- 2- on; 3- (a[S]-cyklopropylbensyl)-4-hydroxi-6-(a[S]-etyl-p[R]-hydroxifenetyl)-2H-pyran- 5 2-on; 3-(a[S]-cyklopropylbensyl)-4-hydroxi-6-(a[R]-etyl-P[R]-hydroxifenetyl)-2H-pyran- 2- on; 3- (a[S]-cyklopropylbensyl)-4-hydroxi-6-(a[S]-etyl-p[S]-hydroxifenetyl)-2H-pyran-2-on; 10 3-(a[R]-cyklopropylbensyl)-4-hydroxi-6-(a[R]-etyl-p[S]-hydroxifenetyl)-2H-pyran- 2- on; 3- (a[R]-cyklopropylbensyl)-4-hydroxi-6-(a[S]-etyl-p[R]-hydroxifenetyl)-2H-pyran- 2- on; 3- (a[R]-cyklopropylbensyl)-4-hydroxi-6-(a[R]-etyl-P[R]-hydroxifenetyl)-2H-pyran- 15 2-on; och 3-(a[R]-cyklopropylbensyl)-4-hydroxi-6-(a[S]-etyl-P[S]-hydroxifenetyl)-2H-pyran- 2- on.
11. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en 20 forening, utvald frän gruppen som bestär av :\j 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; . · · · I 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-etyl- [p-fluorfenetyl])-2H-pyran-2-on; .VI ^ 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-klorfenetyl])-2H-pyran-2-on; \ *. 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-bromfenetyl])-2H-pyran-2-on; *· " 25 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-metylfenetyl])-2H-pyran-2-on; *·· : 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-metoxylifenetyl])-2H-pyran-2-on; ·♦· : 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-hydroxifenetyl])-2H-pyran-2-on; 3- (a-etyl(furfur-2-yl))-4-hydiOxi-6-(a-etyl-[p-trifluormetylfenetyl])-2H-pyran-2-on; :T: 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])-2H-pyran-2-on; : * “j 30 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-fluorfenetyl])-2H-pyran- *. 2-on; • · · 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-klorfenetyl])-2H-pyran-*···* 2-on; ·:·*: 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-bromfenetyl])-2H-pyran- 35 2-on; 277 3-(a-etyl(furfiir-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metylfenetyl])-2H-pyran- 2- on; 3- (a-etyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metoxylfenetyl])-2H-pyran-2-on; 5 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-hydroxifenetyl])-2H-pyran-2-on; 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-trifluormetylfenetyl])- 2H-pyran-2-on; 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-trifluormetylfenetyl])-10 2H-pyran-2-on; 3-(a-etyl(fiirfur-2-yl))-4-hydroxi-6-(l-(tetrahydrofuran-2-ylmetyl)propyl)-2H-pyran- 2- on; 3- (a-etyl(furfur-2-yl))-4-hydroxi-6-(l-(tetrahydrofiiran-3-ylmetyl)propyl)-2H-pyran- 2- on; 15 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-( 1 -(tetrahydrofuran-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3- (a-etyl(furfur-2-yl))-4-hydroxi-6-(l-(tetrahydrofuran-3-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3 -(a-etyl(furfur-2-yl))-4-hydroxi-6-( 1 -(tetrahydropyran-2-ylmetyl)propyl)-2H-pyran-20 2-on; .. : 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-( 1 -(tetrahydropyran-3-ylmetyl)propyl)-2H-pyran- • ·· ··*' 2-on; • » 3-(a-etyl(furfUr-2-yl))-4-hydroxi-6-(l-(tetrahydropyran-4-ylmetyl)propyl)-2H-pyran-[./. 2-on; *· " 25 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(l-(tetrahydropyran-2- :.: : ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; • · « : 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(l-(tetrahydropyran-3- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; :T: 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-( 1 -(tetrahydropyran-4- 30 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; • · · e \ 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(l-(furan-2-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-etyl(furfiir-2-yl))-4-hydroxi-6-(l-(furan-3-ylmetyl)piOpyl)-2H-pyran-2-on; *···* 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(l-(tiofen-2-ylmetyl)propyl)-2H-pyran-2-on; *:··: 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-(l-(tiofen-3-ylmetyl)propyl)-2H-pyran-2-on; ....: 35 3-(a-etyl(furfur-2-yl))-4-hydroxi-6-( 1 -(furan-2-ylmetyl)cyklopropylmetyl)-2H-pyran- 2-on; 278 3-(a-etyl(furfur-2-y]))-4-hydroxi-6-(l-(furan-3-ylmetyl)cyklopropylmetyl)-2H-pyran- 2- on; 3- (a-etyl(furfur-2-yl))-4-hydroxi-6-(l-(tiofen-2-ylmetyl)cyklopropylrnetyl)-2H-pyran-2-on; 5 3-(a-etyl(furfiir-2-yl))-4-hydroxi-6-( 1 -(tiofen-3-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-fluorfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-klorfenetyl])-2H-pyran-2-on; 10 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-bromfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-metylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(fiirfur-2-yl))-4-hydroxi-6-(a-etyl-[p-metoxylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-hydroxifenetyl])-2H-pyran-2-15 on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])-2H- pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])-2H- pyran-2-on; 20 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-fluorfenetyl])-... . 2H-pyran-2-on; I.. * 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-klorfenetyl])-2H- pyran-2-on; • · · : ·[ 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-bromfenetyl])- :.**i 25 2H-pyran-2-on; :.: · 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metylfenetyl])- 2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metoxylfenety])- 2H-pyran-2-on; .···. 30 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-hydroxifenetyl])- *·] 2H-pyran-2-on; 3-(a-cyklopropyl(iurfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p- ··« •...: trifluormetylfenetyl])-2H-pyran-2-on; ....: 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(a-cyklopropylmetyl-[p- ....: 35 trifluormetylfenetyl])-2H-pyran-2-on; • · 3-(a-cyklopropyl(furfin-2-yl))-4-hydroxi-6-(l-tetrahydrofuran-2-ylmetyl)propyl)-2H- 279 pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(l-tetrahydrofuran-3-ylmetyl)propyl)-2H- pyran-2-on; 5 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -tetrahydrofuran-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -tetrahydroiuran-3-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(l-tetrahydropyran-2-ylmetyl)propyl)-10 2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(l-tetrahydropyran-3-ylmetyl)propyl)- 2H-pyran-2-on; 3-(a-cykIopropyl(furfur-2-yl))-4-hydroxi-6-(l-tetrahydropyran-4-ylmetyl)propyl)- 2H-pyran-2-on; 15 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -tetrahydropyran-2- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(l-tetrahydropyran-3-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3 -(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -tetrahydropyran-4-20 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; .. : 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -(furan-2-ylmetyl)propyl)-2H-pyran-2- t ·· ··· on, • · .'.'l 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -(furan-3-ylmetyl)propyl)-2H-pyran-2- !·.*: on; / 25 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(l-(tiofen-2-ylmetyl)propyl)-2H-pyran-2- :.: : on; ·»« : 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-(l-(tiofen-3-ylmetyl)propyl)-2H-pyran-2- on; :T: 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -(furan-2-ylmetyl)cyklopropylmetyl)- .***. 30 2H-pyran-2-on; • · « *. 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -(furan-3-ylmetyl)cyklopropylmetyl)- *“·* 2H-pyran-2-on; ' ‘ ·; · * 3 -(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -(tiofen-2-ylmetyl)cyklopropylmetyl)- :··· 2H-pyran-2-on; •: · · j 35 3-(a-cyklopropyl(furfur-2-yl))-4-hydroxi-6-( 1 -(tiofen-3-ylmetyl)cyklopropylmetyl)- 2H-pyran-2-on; 280 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-fluorfenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-klorfenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-bromfenetyl])-2H-pyran-2-5 on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-metylfenetyl])-2H-pyran-2- on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-metoxylfenetyl])-2H-pyran-2- on; 10 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-hydroxifenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])-2H- pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])-2H-15 pyran-2-on; 3-(a-etyl(5-metyl(furfiir-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-fluorfenetyl])- 2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-klorfenetyl])- 2H-pyran-2-on; 20 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-bromfenetyl])-... . 2H-pyran-2-on; 1./ 3-(a-etyl(5-metyl(fiirfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metylfenetyl])- ]··** 2H-pyran-2-on; • · · :. [ 3-(a-etyl(5-metyl(fiirfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- *.*·: 25 metoxylfenetyl])-2H-pyran-2-on; :.: · 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- :.: : hydroxifenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-: : ; trifluormetylfenetyl])-2H-pyran-2-on; .*··. 30 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- *] trifluormetylfenetyl])-2H-pyran-2-on; • · · * ·: · * 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tetrahydrofuran-2-ylmetyl)propyl)- 2H-pyran-2-on; ....: 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tetrahydroiuran-3-ylmetyl)propyl)- ....: 35 2H-pyran-2-on; 281 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tetrahydrofuran-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfiir-2-yl)))-4-hydroxi-6-( 1 -tetrahydrofuran-3-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 5 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tetrahydropyran-2-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tetrahydropyran-3-ylmetyl)propyl)- 2H-pyran-2-on; 3-(a-etyl(5-metyl(furf\ir-2-yl)))-4-hydroxi-6-(l-tetrahydropyran-4-ylmetyl)propyl)-10 2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tetrahydropyran-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tetrahydropyran-3-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 15 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l -tetrahydropyran-4-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-furan-2-ylmetyl)propyl)-2H-pyran-2- on; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-furan-3-ylmetyl)propyl)-2H-pyran-2-20 on; ... ; 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tiofen-2-ylmetyl)propyl)-2H-pyran-2- • M • · , ··· Oil j • · .”·* 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tiofen-3-ylmetyl)propyl)-2H-pyran-2- • · · ; ·* on; • · *: 25 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-fiiran-2-ylmetyl)cyklopropylmetyl)- :.: : 2H-pyran-2-on; : 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -furan-3-ylmetyl)cyklopropylmetyl)- 2H-pyran-2-on; ;*·*: 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tiofen-2-ylmetyl)cyklopropylmetyl)- .···. 30 2H-pyran-2-on; ·] 3-(a-etyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tiofen-3-ylmetyl)cyklopropylmetyl)- 2H-pyran-2-on; • · · 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; ....: 3-(a-cyklopropyl(5-metyl(flirfur-2-yl)))-4-hydroxi-6'(a-etyl-[p-fluorfenetyl])-2H- ....: 35 pyran-2-on; • % 282 3-(a-cyklopropyl(5-metyl(fiirfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-klorfenetyl])-2H- pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-bromfenetyl])-2H- pyran-2-on; 5 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-metylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-metoxylfenetyl])-2H- pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-hydroxifenetyl])-2H-10 pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p- trifluormetylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-etyl-[p-tri fluormetyl fenetyl] )-2 H-pyran-2-on; 15 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-fluorfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- klorfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-20 bromfenetyl])-2H-pyran-2-on; ... . 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- I.. * metylfenetyl] )-2H-pyran-2-on; • · 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- • · « : ·' metoxylfenetyl])-2H-pyran-2-on; :.**i 25 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- • « :.· · hydroxifenetyl])-2H-pyran-2-on; v‘: 3-(a-cyklopropyl(5-metyl(furftir-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- trifluormetylfenetyl])-2H-pyran-2-on; :*·*; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- .···. 30 trifluormetylfenetyl])-2H-pyran-2-on; ’·” 3-(a-cyklopropyl(5-metyl(furfUr-2-yl)))-4-hydroxi-6-(l-tetrahydrofuran-2- ylmetyl)propyl)-2H-pyran-2-on; • · · 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tetrahydrofuran-3-....: ylmetyl)propyl)-2H-pyran-2-on; ....: 35 3-(a-cyklopropyl(5-metyl(i\iriur-2-yl)))-4-hydroxi-6-( 1 -tetrahydrofuran-2- • · ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(fiirfur-2-yl)))-4-hydroxi-6-(l-tetrahydrofuran-3- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 283 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tetrahydrc>pyran-2- ylmetyl)propyl)-2H-pyran-2-on; 5 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tetrahydropyran-3- ylmetyl)propyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tetrahydropyran-4- ylmetyl)propyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfiir-2-yl)))-4-hydroxi-6-(l-tetrahydropyran-2-10 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tetrahydropyran-3- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tetrahydropyran-4- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 15 3-(a-cyklopropyl(5-metyl(furfiir-2-yl)))-4-hydrc)xi-6-( 1 -furan-2-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-furan-3-ylmetyl)propyl)-2H- pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-l-(tiofen-2-ylmetyl)propyl)-2H-20 pyran-2-on; ..φ . 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-1 -(tiofen-3-ylmetyl)propyl)-2H- 1.. ‘ pyran-2-on; • · 3 -(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -furan-2- • · · : ·* ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; ·.*·: 25 3-(a-cyklopropyl(5-metyl(iurfur-2-yl)))-4-hydroxi-6-(l-furan-3- • · :.: · ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; ί.: : 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-( 1 -tiofen-2- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(furfur-2-yl)))-4-hydroxi-6-(l-tiofen-3- t .*··. 30 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; ·[ 3-(a-etyl(tiofen-2-yl-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; • · · *·:·* 3-(a-etyl(tiofen-2-yl-4-hydroxi-6-(a-etyl-[p-fluorfenetyl])-2H-pyran-2-on; • · · :...: 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-klorfenetyl])-2H-pyran-2-on; ....: 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-bromfenetyl])-2H-pyran-2-on; ....: 35 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-metylfenetyl])-2H-pyran-2-on; • · 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-metoxylfenetyl])-2H-pyran-2-on; 284 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-hydroxifenetyl])-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])-2H-pyran- 2- on; 3- (a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])-2H-pyran- 5 2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-fluorfenetyl])-2H- pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-klorfenetyl])-2H- pyran-2-on; 10 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-bromfenetyl])-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metylfenetyl])-2H- pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metoxylfenetyl])-15 2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-hydroxifenetyl])- 2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p- trifluormetylfenetyl])-2H-pyran-2-on; 20 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-.·. : trifluormetylfenetyl])-2H-pyran-2-on; . · · · [ 3 -(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -(tetrahydrofuran-2-ylmetyl)propyl)-2H- • · •VI' pyran-2-on; *. \ 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-(tetrahydrofuran-3-ylmetyl)propyl)-2H- • ♦ · / 25 pyran-2-on; ··: i 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-(tetrahydrofuran-2- ··· : ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -(tetrahydrofliran-3-:T: ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; :***: 30 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l -(tetrahydropyran-2-ylmetyl)propyl)-2H- ··· *. pyran-2-on; • » · **ί;* 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -(tetrahydropyran-3-ylmetyl)propyl)-2H- • · ’···* pyran-2-on; ·:··· 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-(tetrahydropyran-4-ylmetyl)propyl)-2H- 35 pyran-2-on; 285 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-3-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 5 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-4-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-furan-2-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-furan-3-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-tiofen-2-ylmetyl)propyl)-2H-pyran-2-on; 10 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tiofen-3-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-furan-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-furan-3-ylmetyl)cyklopropylmetyl)-2H- pyran-2-on; 15 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tiofen-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-tiofen-3-ylmetyl)cyklopropylmetyl)-2H- pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 20 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-fluorfenetyl])-2H-pyran- : 2-on; • ·· .··/ 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-klorfenetyl])-2H-pyran- 2- on; • · · \ 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-bromfenetyl])-2H-pyran- 25 2-on; • · :.: : 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-metylfenetyl])-2H-pyran- ·♦* ·.· · 2-on; 3- (a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-metoxylfenetyl])-2H- :T: pyran-2-on; :***. 30 3-(a-cykIopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-hydroxifenetyl])-2H- • ·· ·. pyran-2-on; • · · *;j*‘ 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])- • · *»··* 2H-pyran-2-on; ·:··· 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])- ....: 35 2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p- 286 fluorfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p- klorfenetyl])-2H-pyran-2-on; 5 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-bromfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p- metylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-10 metoxylfenety])-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-hy dr o x i fenety 1])-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p- trifluormetylfenetyl])-2H-pyran-2-on; 15 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(a-cyklopropylmetyl-[p-trifluormetylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1-tetrahydrofuran-2-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-tetrahydrofuran-3-20 ylmetyl)propyl)-2H-pyran-2-on; . . 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydrofuran-2- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; • · 3 -(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydrofiiran-3- • · · • ·* ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; : 25 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-2- • · :.· · ylmetyl)propyl)-2H-pyran-2-on; : : 3 -(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-3- ylmetyl)propyl)-2H-pyran-2-on; . . 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-4- • .···. 30 ylmetyl)propyl)-2H-pyran-2-on; *·] 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-2- *.:.: ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; • · · 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-3-....: ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; ....: 35 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -tetrahydropyran-4- • · ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-(furan-2-ylmetyl)propyl)-2H- 287 pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-(furan-3-ylmetyl)propyl)-2H- pyran-2-on; 5 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -(tiofen-2-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-(tiofen-3-ylmetyl)propyl)-2H- pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-(furan-2-ylmetyl)propyl)-2H-10 pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-(l-(furan-3-ylmetyl)propyl)-2H- pyran-2-on; 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -(tiofen-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 15 3-(a-cyklopropyl(tiofen-2-ylmetyl))-4-hydroxi-6-( 1 -(tiofen-3- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-fluorfenetyl])-2H- pyran-2-on; 20 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-klorfenetyl])-2H-pyran-.·. : 2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-bromfenetyl])-2H-[···* pyran-2-on; • ·* 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-metylfenetyl])-2H- :.*·· 25 pyran-2-on; ·,· j 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-metoxylifenetyl])-2H- :T: pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-hydroxifenetyl])-2H- pyran-2-on; .···. 30 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])- *·] 2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-trifluormetylfenetyl])- ··· 2H-pyran-2-on; ....: 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- ....: 35 fluorfenetyl])-2H-pyran-2-on; • · 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- 288 klorfenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- bromfenetyl])-2H-pyran-2-on; 5 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metylfenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- metoxylfenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-10 hydroxifenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- trifluormetylfenetyl])-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- trifluormetylfenetyl])-2H-pyran-2-on; 15 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(tetrahydrofuran-2- ylmetyl)propyl)-2H-pyran-2-on; 3 -(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(tetrahydrofuran-3-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tetrahydrofuran-2-20 ylmetyl)cyklopropylmetyl)'2H-pyran-2-on; . . 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tetrahydrofuran-3- * *. / ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; \y·' 3 -(a-etyl(5 -metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(tetrahydropyran-2- : ylmetyl)propyl)-2H-pyran-2-on; : 25 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(tetrahydropyran-3- ·,· · ylmetyl)propyl)-2H-pyran-2-on; :T: 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(tetrahydropyran-4- ylmetyl)propyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tetrahydropyran-2- .···. 30 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; • · 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tetrahydropyran-3- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; • · · :...: 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(tetrahydropyran-4- ....: ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; ....: 35 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(furan-2-ylmetyl)propyl)-2H- • · pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(furan-3-ylmetyl)propyl)-2H- 289 pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tiofen-2-ylmetyl)propyl)-2H- pyran-2-on; 5 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tiofen-3-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(furan-2-ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(furan-3-10 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tiofen-2- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-etyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tiofen-3- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 15 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etylfenetyl)-2H-pyran- 2- on; 3- (a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-fluorfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-klorfenetyl])-20 2H-pyran-2-on; ... . 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-bromfenetyl])- • · · !..* 2H-pyran-2-on; //1 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p-metylfenetyl])- • · · : 2H-pyran-2-on; *.’·: 25 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p- • · :.: : metoxylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p- hydroxifenetyl])-2H-pyran-2-on; ;*j*; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p- .**·. 30 trifluormetylfenetyl])-2H-pyran-2-on; *·] 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-etyl-[p- *. * trifluormetylfenetyl])-2H-pyran-2-on; ♦ ·· 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-....: fluorfenetyl])-2H-pyran-2-on; ....: 35 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- • · klorfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- 290 bromfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- metylfenetyl])-2H-pyran-2-on; 5 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-metoxylfenety])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- hydroxifenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p-10 trifluormetylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(a-cyklopropylmetyl-[p- trifluormetylfenetyl])-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-tetrahydrofuran-2- ylmetyl)propyl)-2H-pyran-2-on; 15 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -tetrahydrofuran-3-ylmetyl)propyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-tetrahydrofuran-2- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-tetrahydrofuran-3-20 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; . . : 3 -(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -tetrahydropyran-2- ylmetyl)propyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-tetrahydropyran-3- • · · \ ·] ylmetyl)propyl)-2H-pyran-2-on; • · · *· *: 25 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-tetrahydropyran-4- :.: : ylmetyl)propyl)-2H-pyran~2-on; • · · : 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-tetrahydropyran-2- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; :*·*: 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-tetrahydropyran-3- 30 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; • · · ·. 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -tetrahydropyran-4- ♦ · · * · [ · * ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; : 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(fiiran-2- ylmetyl)propyl)-2H-pyran-2-on; ....: 35 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(furan-3- ylmetyl)propyl)-2H-pyran-2-on; 291 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tiofen-2- ylmetyl)propyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tiofen-3- ylmetyl)propyl)-2H-pyran-2-on; 5 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-( 1 -(furan-2- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(furan-3- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tiofen-2-10 ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; 3-(a-cyklopropyl(5-metyl(tiofen-2-ylmetyl)))-4-hydroxi-6-(l-(tiofen-3- ylmetyl)cyklopropylmetyl)-2H-pyran-2-on; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- yl]-fenylsulfonamid;
15 N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-fenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- yl]-p-fluorfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-20 ylmetyl]-p-fluorfenylsulfonamid; ^ . N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- yl]-p-klorfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- • · · : ·* ylmetyl]-p-klorfenylsulfonamid;
25 N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- • · :.· * yl]-3,4-diklorfenylsulfonamid; :T: N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- ylmetyl]-3,4-diklorfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-.*··. 30 yl]-p-cyanofenylsulfonamid; *·] N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- :.: ylmetyl]-p-cyanofenylsulfonamid; ··» N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-....: yl]-p-trifluormetylfenylsulfonamid; ....: 35 N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- • · ylmetyl]-p-trifluormetylfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- 292 yl]-m-fluorfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- ylmetyl]-m-fluorfenylsulfonamid;
5 N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-m-klorfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- ylmetyl]-m-klorfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-10 yl]-m-cyanofenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- ylmetyl]-m-cyanofenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- yl]-m-trifluormetylfenylsulfonamid;
15 N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- ylmetyl]-m-trifluormetylfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- yl]-o-fluorfenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-20 ylmetyl]-o-fluorfenylsulfonamid; ^ . N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- yl]-o-klorfenylsulfonamid; I”·* N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- • · · • ·' ylmetyl]-o-klorfenylsulfonamid;
25 N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2- : yl]-o-cyanofenylsulfonamid; :T: N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- ylmetyl]-o-cyanofenylsulfonamid; N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-.···. 30 yl]-o-trifluormetylfenylsulfonamid; *·* N-[5-[(a-cyklopropyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2- :.:.: ylmetyl]-o-trifluormetylfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furiur-2-yl]-....: fenylsulfonamid; ....: 35 N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- • · fenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-p- 293 r fluorfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi>2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- p-fluorfenylsulfonamid;
5 N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-p-klorfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- p-klorfenylsulfonamid; N- [5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3 -yl] -metyl] furfur-2 -yl]-3,4-10 diklorfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-3,4-diklorfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-p- cyanofenylsulfonamid;
15 N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-p-cyanofenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyI]furfur-2-yl]-p- trifluormetylfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]-20 p-trifluormetylfenylsulfonamid; ; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-m- • · · fluorfenylsulfonamid; //;' N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- • · · : ·' m-fluorfenylsulfonamid;
25 N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-m- • · : klorfenylsulfonamid; : N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- m-klorfenylsulfonamid; :*·*: N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-m- .***. 30 cyanofenylsulfonamid; ” N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- • · · *·:·* m-cyanofenylsulfonamid; • · · N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]iurfur-2-yl]-m-....: trifluormetylfenylsulfonamid; ....: 35 N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- • · m-trifluormetylfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-o- 294 fluorfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- o-fluorfenylsulfonamid;
5 N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-o-klorfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- o-klorfenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]furfur-2-yl]-o-10 cyanofenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- o-cyanofenylsulfonamid; N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]ftirfur-2-yl]-o- trifluormetylfenylsulfonamid;
15 N-[5-[(a-etyl-a-(6-(a-etylfenetyl)-4-hydroxi-2-pyran-3-yl]-metyl]tiofen-2-ylmetyl]- o-trifluormetylfenylsulfonamid; 3-(a[S]-cyklopropyl(m-fluorbensyl))-4-hydroxi-6-(a[R]-etyl-p-tetrahydropyran-4- yl)etyl-2H-pyran-2-on; 3-(a[S]-cyklopropyl(m-fluorbensyl))-4-hydroxi-6-(a[S]-etyl-P-tetrahydropyran-4-20 yl)etyl-2H-pyran-2-on; .·. : 3-(a[S]-cyklopropyl(m-fluorbensyl))-4-hydroxi-6-(a[R]-etyl-P-tetrahydropyran-4- • · · .*./ yl)etyl-2H-pyran-2-on; • · 3-(a[S]-cyklopropyl(m-fluorbensyl))-4-hydroxi-6-(a[S]-etyl-P-tetrahydropyran-4- • · · \ ·[ yl)etyl-2H-pyran-2-on; *· *i 25 3-(a[R]-cyklopropyl(m-fluorbensyl))-4-hydroxi-6-(a[R]-etyl-P-tetrahydropyran-4- :.: : yl)etyl-2H-pyran-2-on; ··· : 3-(a[R]-cyklopropyl(m-fluorbensyl))-4-hydroxi-6-(a[S]-etyl-P-tetrahydropyran-4- yl)etyl-2H-pyran-2-on; 3-(a[R]-cyklopropyl(m-fluorbensyl))-4-hydroxi-6-(a[R]-etyl-P-tetrahydropyran-4-.***. 30 yl)etyl-2H-pyran-2-on; och ·. 3-(a[R]-cyklopropyl(m-fluorbensyl))-4-hydroxi-6-(a[S]-etyl-P-tetrahydropyran-4- *·:·* yl)etyl-2H-pyran-2-on. • · • · • · · •: · · · 12. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en ....: 35 fÖrening, utvald frän gruppen som bestär av (3S,6R)-3-(a-etyl-4-hydroxibensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 295 (3S,6R)-3-(a-etylbensyl)-6-(a-etyl-4-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; (3S,6R)-3-(a-etyl-4-hydroxibensyl)-6-(a-etyl-4-hydroxifenetyl)-4-hydroxi-2H-pyran- 2- on; (3S,6aR,6pR) 3-(a-etylbensyl)-6-(a-etyl-P-hydroxifenetyl)-4-hydroxi-2H-pyran-2-5 on; (3S,6ccR,6pS) 3-(a-etylbensyl)-6-(a-etyl-P-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; (3S,6aR,6pR) 3-(a-etyl-4-hydroxibensyl)-6-(a-etyl-P-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; (3S,6aR,6pS) 3-(a-etyl-4-hydroxibensyl)-6-(a-etyl-P-hydroxifenetyl)-4-hydroxi-2H-10 pyran-2-on; (3S,6aR,6pR) 3-(a-etylbensyl)-6-(a-etyl-P-hydroxi-4-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; (3S,6aR,6pS) 3-(a-etylbensyl)-6-(a-etyl-P-hydroxi-4-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; 15 (3S,6aR,6pR) 3-(a-etyl-4-hydroxibensyl)-6-(a-etyl-P-hydroxi-4-hydroxifenetyl)-4- hydroxi-2H-pyran-2-on; (3S,6aR,6pS) 3-(a-etyl-4-hydroxibensyl)-6-(a-etyI-p-hydroxi-4-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; (3S,6R) 3-(α-( 1 [R]-hydroxietyl)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 20 (3S,6R) 3-(a-(l [R]-hydroxietyl)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; .·. : (3S,6S) 3-(a-etylbensyl)-6-(a-(l[R]-hydroxietyl)fenetyl)-4-hydroxi-2H-pyran-2-on; .1./ (3S,6S) 3-(a-etylbensyl)-6-(a-(l[S]-hydroxietyl)fenetyl)-4-hydroxi-2H-pyran-2-on; (35.65) 3-(a-(l[R]-hydroxietyl)bensyl)-6-(a-(l[R]-hydroxietyl)fenetyl)-4-hydroxi- • · · ·] 2H-pyran-2-on; ’· 1: 25 (3S,6S) 3-(a-(l[R]etyl)bensyl)-6-(a-(l[S]-hydroxietyl)fenetyl)-4-hydroxi-2H-pyran- • · :.: : 2-on; v : (3S,6S) 3-(a-(l[R]-hydroxietyl)bensyl)-6-(a-(l[S]-hydroxietyl)fenetyl)-4-hydroxi- 2H-pyran-2-on; (35.65) 3-(α-( 1 [S]etyl)bensyl)-6-(a-( 1 [R]-hydroxietyl)fenetyl)-4-hydroxi-2H-pyran- .·**. 30 2-on; \ (3S,6R) 3-(a-(2-hydroxietyl)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; *·ί·1 (3S,6R) 3-(a-etylbensyl)-6-(a-(2-hydroxietyl)fenetyl)-4-hydroxi-2H-pyran-2-on; (3S,6R) 3-(a-(2-hydroxietyl)bensyl)-6-(a-(2-hydroxietyl)fenetyl)-4-hydroxi-2H-....: pyran-2-on; ....: 35 3-(a-etyl-4-hydroxibensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 3- (a-etylbensyl)-6-(a-4-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; 3-(α- 4-hydroxibensyl)-6-(a-etyl-4-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; 296 3-(a-4-hydroxibensyl)-6-(a-etyl-P-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; 3-(a-etylbensyl)-6-(a-etyl-P-hydroxi-4-hydroxifenetyl)-4-hydroxi-2H-pyran-2-on; 3-(α- 4-hydroxibensyl)-6-(a-etyl-P-hydroxi-4-hydroxifenetyl)-4-hydroxi-2H-pyran-2-5 on; 3-(a-(l-hydroxietyl)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 3-(a-etylbensyl)-6-(a-(l-hydroxietyl)fenetyl)-4-hydroxi-2H-pyran-2-on; 3-(α-( 1 -hydroxietyl)bensyl)-6-(a-( 1 -hydroxietyl)fenetyl)-4-hydroxi-2H-pyran-2-on; 3-(a-(2-hydroxietyl)bensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; 10 3-(a-etylbensyl)-6-(a-(2-hydroxietyl)fenetyl)-4-hydroxi-2H-pyran-2-on; och 3-(a-(2-hydroxietyl)bensyl)-6-(a-(hydroxietyl)fenetyl)-4-hydroxi-2H-pyran-2-on.
13. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en fbrening, utvald frän gruppen som bestär av: 15 (3S,6R)-3-(a-etylbensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; (3S,6S)-3-(a-etylbensyI)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; natrium-(3S,6R)-3-(a-etylbensyl)-6-(a-etylfenetyl)-2H-pyran-2-on-4-oxid; (3R,6R)-3-(a-etylbensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on; och (3R,6S)-3-(a-etylbensyl)-6-(a-etylfenetyl)-4-hydroxi-2H-pyran-2-on. 20 φ · * · · • · · • · • · · • » • # ··· ·♦ · • · « • · • · • · • · · ♦ · · • « • · • · · • · · ··« · • ·· « · · • · · »«· ♦ · ♦ • · · • · · • · • · • · · • · · • · · • · · • · · • · • · • · · 1 · • ·
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US97534392A | 1992-11-13 | 1992-11-13 | |
US97534392 | 1992-11-13 | ||
US9087693A | 1993-07-13 | 1993-07-13 | |
US9087693 | 1993-07-13 | ||
US13064193A | 1993-10-01 | 1993-10-01 | |
US13064193 | 1993-10-01 | ||
PCT/US1993/010645 WO1994011361A1 (en) | 1992-11-13 | 1993-11-09 | Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating hiv and other retroviruses |
US9310645 | 1993-11-09 |
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NZ275325A (en) * | 1993-11-19 | 1999-08-30 | Parke Davis & Co | 3,4,6-trisubstitutedpyran-2-one derivatives |
IL129871A (en) * | 1994-05-06 | 2003-11-23 | Pharmacia & Upjohn Inc | Process for preparing 4-phenyl-substituted octanoyl-oxazolidin-2-one intermediates that are useful for preparing pyran-2-ones useful for treating retroviral infections |
DK0817786T3 (da) * | 1995-03-20 | 2003-05-26 | Upjohn Co | Substituerede tetronsyrer, der er nyttige til behandling af HIV og andre retrovira |
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EP1281399A3 (en) * | 2001-08-01 | 2004-02-11 | Warner-Lambert Company | Dual inhibitors of wax ester and cholesteryl ester synthesis for inhibiting sebum production |
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