FI86169B - Foerfarande foer framstaellning av terapeutiskt aktiva fenyl-, pyridyl-, kinolyn- eller tienylsubstituerade alken-, alkyn- eller cykloalkylenderivat. - Google Patents

Foerfarande foer framstaellning av terapeutiskt aktiva fenyl-, pyridyl-, kinolyn- eller tienylsubstituerade alken-, alkyn- eller cykloalkylenderivat. Download PDF

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FI86169B
FI86169B FI850888A FI850888A FI86169B FI 86169 B FI86169 B FI 86169B FI 850888 A FI850888 A FI 850888A FI 850888 A FI850888 A FI 850888A FI 86169 B FI86169 B FI 86169B
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formula
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alkyl
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FI850888A
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FI86169C (sv
FI850888L (fi
FI850888A0 (fi
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Leslie Richard Hughes
Howard Tucker
John Oldfield
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Ici Plc
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    • C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
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Claims (5)

1. Förfarande för framställning av en terapeutiskt aktiv förening med formeln (I) 5 y~\ R4-f— A —)-X-CR7R8-OH I yy R3 R2 10 väri X har formeln CH2 -CR5=CR6-, -ChC- eller -CR5-^CR6- ring A är fenyl, pyridyl, kinolyl eller tienyl;
15 R2, R3 och R4, som kan vara samma eller oi ikä, är vardera en elektronattraherande substituent som valts av gruppen halogen, nitro, cyan och trifluormetyl och alkyltio, alkyl-sulfinyl och alkylsulfonyl, var med högst 6 kolatomer, eller vardera är väte eller alkyl, alkoxi eller dialkylami-20 no, vilka innehäller högst 6 kolatomer, förutsatt, att dä ring A är fenyl, är minst en av radikalerna R2, R3 och R4 en elektronattraherande substituent; R5 och R6, som kan vara samma eller oiikä, betecknar väte eller alkyl med högst 6 kolatomer;
25 R7 är halogenalkyl med högst 6 kolatomer; och Rfl är karbamoyl, alkyl, cykloalkyl, alkenyl, alkynyl, halogenalkyl, halogenalkenyl, halogenalkynyl eller alkanoyl, var med högst 6 kolatomer, eller alkylkarbamoyl eller di-alkylkarbamoyl, i vilka varje alkyl innehäller högst 6 . . 30 kolatomer, eller R8 är alkyl eller alkenyl, vilka vardera innehäller högst 6 kolatomer och vilka har en eller flera substituenter som valts av gruppen cyan, karbamoyl, amino och hydroxi, alkanoyl, alkoxi, alkyltio, alkenyltio, al-. kylsulfinyl, alkenylsulfinyl, alkylsulfonyl, alkenylsul- 35 fonyl, alkanoylamino, alkoxikarbonylamino och alkylsul- 53 8 6169 fonamido, vilka alla innehäller högst 6 kolatomer, och dialkylsulfamoyl med högst 6 kolatomer i bäda alkylgrup-per, aryl, aryltio, arylsulflnyl och arylsulfonyl, i vilka arylgruppen är fenyl, tolyl, fluorfenyl, klorfenyl, nitro-5 fenyl, metyltiofenyl, metylsulfonylfenyl, karbamoylfenyl, acetamidofenyl eller dimetylaminofenyl, och heterocyklyl-tio, heterocyklylsulfinyl och heterocyklylsulfonyl; var-vid den heterocykliska radikalen i R® är en 5- eller 6-le-dad heterocykel innehällande 1, 2 eller 3 heteroatomer, 10 varav var och en är kväve eller svavel, och vilken heterocykel är en enskild ring eller fusionerad med en eller tvä fenylringar eller med en annan heterocyklisk ring som ovan definierats och vilken heterocykel är osubstituerad eller substituerad med ovan definierade radikaler R2, R3 15 och R4 eller den kan ocksä ha en eller flera hydroxi-, merkapto- eller aminosubstituenter, eller R® har formeln R2 R3 väri ring B är fenyl och väri radikalerna R2, R3 och R4 har vilken som heist av de ovan angivna betydelserna, eller B är pyridyl eller tiazolyl, som är osubstituerad eller 25 substituerad med en halogen- eller trifluormetylsubstitu-ent, eller 1,3-ditian-2-yl, kännetecknat därav, att a) för framställning av en alken, väri X är -CR5=CR6-, omsätts en förening med formeln (II) r4Xa4-CR5=CR6-COR7 H R R 54 86169 väri A, R2, R3, R4, R5, R6 och R7 betecknar samma som ovan, med en organometallförening med formeln R8-M, väri R8 be-tecknar samma som ovan och M är en metallisk grupp; eller b) för framställning av en alken, väri X är 5 -CR5=CR6- och R8 har formeln -CH2R9, omsätts en epoxid med formeln (lii) R4—(— A -4— CR5=CR6-CR7—III VV
10 R3 R2 väri A, R2, R3, R4, R5, R6 och R7 betecknar samma som ovan, med en förening med formeln R9-H, väri R9 är sädan, att man för -CH2R9 fär en betydelse som ovan anfördes för R8, eller 15 c) för framställning av en alken, väri R5 är väte och X är -CH=CR6-, dehydratiseras en förening med formeln (IV) RtL a -)-CHOH CHR6CR7R8-OH IV 20 R3 R2 väri A, R2, RJ, R4, R5, R6, R7 och R8 betecknar samma som ovan; eller 25 d) för framställning av en alken, väri X är -CRb=CR''-, omsätts en förening med formeln (V) r4.-(— A—H—COR5 MV, R3 R 30 väri A, R2, R3, R4 och R5 betecknar samma som ovan, med en förening med formeln -M R7C0R8 35 väri R7 och R8 betecknar samma som ovan; eller 55 8 6 Ί 69 e) för framställning av ett cykloalkylenderivat, väri X är ^CH2 -CR omsätts en förening med formeln (VI) 5 /""S ca, R4—(- A —i—CR5-CR6-M VI R3 XR2 10 väri A, R2, R3, R4, R5, R6 och M betecknar samma som ovan, med en förening med formeln R7C0R8 15 väri r' och RH betecknar samma som ovan; eller f) för framställning av en alkyn, väri X är -C=C-, omsätts en förening med formeln (VII) R4—f—A—ή— Z VII 20 R3 R2 väri A, R2, R3 och R4 betecknar samma som ovan och Z är en grupp som kan ersättas, med en förening med formeln /: 25 HChC-CR7R8OH väri R7 och R8 betecknar samma som ovan; eller g) för framställning av en alken, väri X är -CR5=CR6- och R8 är karbamoyl, omsätts en förening med for- 30 mein (II) CR5=CR6-C0R7 II .·’ : 35 56 8 6 169 väri A, R2, R3, R4, R5, R6 och R7 betecknar samma som ovan, med en trialkylsilylcyanid, vilken i varje alkyl har högst 6 kolatomer, och hydrolyseras den sä erhällna cyaniden pä konventionellt sätt; 5 varefter en förening, väri X är -C=C-, kan reduce- ras tili motsvarande förening, väri X är -CH=CH-; och varefter i) en förening, väri R8 har en amino-substituent, kan acyleras för erhällande motsvarande förening, väri R8 10 har en alkanoylamino-, alkoxikarbonylamino- eller alkyl-sulfonamidosubstituent; ii) en förening, väri R8 är alkyl innehällande en alkyltio- och alkylsulfinylsubstituent pä samma kolatom, kan omvandlas tili motsvarande förening, väri denna kol- 15 atom är en karbonylgrupp; iii) en förening, väri R8 är alkanoyl eller är alkyl, som är substituerad med alkanoyl, kan reduceras tili motsvarande förening, väri R8 är hydroxialkyl; eller iv) en förening, väri R8 är alkynyl, kan omvandlas 20 tili motsvarande förening, väri R8 är alkanoyl, genom hyd- ratisering pä konventionellt sätt, eller v) en förening, väri en eller flera av radikalerna R2, R3, R4 och en substituent i R8 är alkylsulfinyl eller alkylsulfonyl eller en substituent i R8 är alkenylsulfin- 75 yl, arylsulfinyl, alkenylsulfonyl, arylsulfonyl, hetero-. - cyklylsulfinyl eller heterocyklylsulfonyl, kan framställas genom oxidation av den motsvarande föreningen, väri en eller flera av radikalerna R2, R3, R4 och en substituent i R8 respektive är alkyltio, alkenyltio, aryltio eller he-;V 30 terocyklyltio, eller • vi) en förening, väri R8 är karbamoyl, kan hydro lyseras tili motsvarande förening, väri R8 är karboxi, vil-ken förening kan omvandlas genom en konventionell amida-: tion tili en förening, väri R8 är alkylkarbamoyl eller di- .·. : 35 alkylkarbamoyl, vilka i varje alkyl innehäller högst 6 57 86"i 69 kolatomer.
2. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att X är -CR5=CR6-, ring A är fenyl, 1 eller 2 (samma eller olika) av radikalerna R2, R3 och R4 5 är fluor, klor, cyan, trifluormetyl eller nitro, varvid de andra radikalerna R2, R3 och R4 är väte, R5 och R6 är var-dera väte, R7 är trifluormetyl, pentafluoretyl, heptafluor-propyl, klormetyl eller di-klormetyl, R8 är metyl, etyl, n-propyl, isopropyl, n-butyl, cyklopropyl, cyklopentyl, 10 trifluormetyl, klormetyl, diklormetyl, etynyl, kloretynyl, acetyl eller propionyl eller är metylen (-CH2)-, som sub-stituerats med cyan, hydroxi, karbamoyl, formyl, acetyl, alkyltio, alkenyltio, alkylsulfonyl eller alkenylsulfenyl, vilka vardera innehäller högst 6 kolatomer, med fenyltio 15 eller fenylsulfonyl, som själv är osubstituerad eller har en fluor-, klor-, nitro-, karbamoyl-, acetamido-, metyl-tio- eller metylsulfonylsubstituent eller den har formeln -CH2SR9, väri R9 är pyridyl, kinolyl, pyrimidinyl, purinyl, pyrazolpyrimidinyl, tiazolyl, imidazolyl eller triazolyl, 20 av vilka var och en är osubstituerad eller hydroxi-, mer-kapto-, amino-, klor-, trifluormetyl- eller metylsubsti-tuerad och -CR5=CR6-gruppen är i trans-konfiguration.
3. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att X är trans-CH=CH-, ring A är 25 3,4-diklorfenyl, 3-klor-4-cyanfenyl, 3-klor-4-fluorfenyl, 4-klor-4-cyanfenyl, 3-klor-4-fluorfenyl, 4-klor-3-tri-fluormetylfenyl, 4-cyanfenyl, 4-cyan-3-fluorfenyl, 4-cyan- 3-trifluormetylfenyl eller 4-fluor-3-trifluormetylfenyl, R7 är trifluormetyl och R8 är etyl, etynyl, cyanmetyl, 1-cyan-30 etyl, acetyl, metylsulfonylmetyl, p-metylsulfonylfenyl- sulfonylmetyl eller pyrid-2-ylsulfonylmetyl eller har formeln -CH2SR9, väri R9 är m-metyltiofenyl, pyrid-4-yl, pyri-mid-2-yl, 4,6-dimetylpyrimid-2-yl, purin-6-yl, lH-pyraz-ol[3,4-d]pyrimidin-4-yl, imidazol-2-yl, 1-metyl-imidazol-: 35 2-yl, 7-klorkinolin-4-yl eller 7-trifluormetylkinolin-4- 58 8 6 1 69 yi.
4. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer en förening som valts av gruppen: 5 5-( 3,4-diklorfenyl )-3-hydroxi-3-trif luormetylpent-trans- 4- en-2-on; 5- (3,4-diklorfenyl)- och 5-(4-cyan-3-trifluormetylfenyl)- 3- trifluormetylpent-trans-4-en-l-yn-3-ol; 5-(4-cyanfenyl)- och 5-(4-cyan-3-trifluormetylfenyl)-3-10 hydroxi-3-trifluormetyl-pent-trans-4-ennitril; 4- (3-klor-4-fluorfenyl-, 4-cyanfenyl-, 4-cyan-3-trifluor-metylfenyl-, 4-klor-3-trifluormetylfenyl- och 4-fluor-3-trifluormetylfenyl)-l-metylsulfonyl-2-trifluormetylbut-trans-3-en-2-ol; 15 5-(3,4-diklorfenyl )-3-hydroxi-2-metyl-3-trifluormetylpent- trans-4-ennitril; 4 - ( 3,4-diklorfenyl)-1-(pyrid-4-yltio)-2-trifluormetylbut-trans-3-en-2-ol; 4 - ( 3,4-diklorfenyl )-1-(pyrimidin-2-yltio ) -2-trifluormetyl-20 but-trans-3-en-2-ol; och 4-(3,4-diklorfenyl)-l-(pyrid-2-ylsulfonyl) -2-trifluor-metylbut-trans-3-en-2-ol.
5. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer en förening som 25 valts av gruppen: 4- (4-cyan-3-trifluormetylfenyl)-1-(7-klorkinolin-4-yl-tio)-, l-(7-trifluormetylkinolin-4-yltio)-, l-(pyrimidin- 2-yltio)-, l-(4,6-dimetylpyrimidin-2-yltio)-, l-(purin-6-yltio)-, 1-(lH-pyrazol[3,4-d]pyrimidin-4-yltio)-1-(imid- 30 azol-2-yltio)- och l-(l-metyl-imidazol-2-yltio)-2-tri- fluormetylbut-trans-4-en-2-ol; 5- (3,4-diklorfenyl)- och 5-(4-cyan-3-trifluormetylfenyl)-'3-trifluormetylpent-trans-3-en-2-ol; : : : 4-(3-klor-4-cyanfenyl)-l-(m-metyltiofenyl)tio-2-trifluor- _·’ : 35 metylbut-trans-3-en-2-ol; och 59 8 6169 4- (3-klor-4-cyanfenyl )-1-( p-metylsulfonylfenylsulfonyl) - 2-trifluormetylbut-trans-3-en-2-ol.
FI850888A 1984-03-07 1985-03-05 Förfarande för framställning av terapeutiskt aktiva fenyl-, pyridyl-, kinolyn- eller tienylsubstituerade alken-, alkyn- eller cykloalkylende rivat FI86169C (sv)

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GR850499B (sv) 1985-04-23
NZ211304A (en) 1988-02-12
PT80075A (en) 1985-04-01
DK104885D0 (da) 1985-03-07
EP0154528A2 (en) 1985-09-11
FI86169C (sv) 1992-07-27
ES541044A0 (es) 1986-11-16
EP0154528B1 (en) 1991-12-11
ES8706596A1 (es) 1987-07-01
HU195755B (en) 1988-07-28
GB8406000D0 (en) 1984-04-11
IE850398L (en) 1985-09-07
ZA851268B (en) 1985-12-24
HUT38087A (en) 1986-04-28
NO164294C (no) 1990-09-19
DE3584842D1 (de) 1992-01-23
IE58336B1 (en) 1993-09-08
EP0154528A3 (en) 1989-01-04
JPS60237033A (ja) 1985-11-25
CA1269104A (en) 1990-05-15
JPH0761965B2 (ja) 1995-07-05
IL74486A (en) 1991-03-10
US5032592A (en) 1991-07-16
FI850888L (fi) 1985-09-08
IL74486A0 (en) 1985-06-30
PT80075B (pt) 1987-09-30
NO164294B (no) 1990-06-11
US4873329A (en) 1989-10-10
IE57973B1 (en) 1993-06-02
ATE70256T1 (de) 1991-12-15
FI850888A0 (fi) 1985-03-05
ES555614A0 (es) 1987-07-01
AU3944685A (en) 1985-10-10
DK104885A (da) 1985-09-08
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ES8701139A1 (es) 1986-11-16
NO850887L (no) 1985-09-09

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