FI88793B - Foerfarande foer framstaellning av farmakologiskt aktiva fenylnaftalenderivat - Google Patents

Foerfarande foer framstaellning av farmakologiskt aktiva fenylnaftalenderivat Download PDF

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FI88793B
FI88793B FI914266A FI914266A FI88793B FI 88793 B FI88793 B FI 88793B FI 914266 A FI914266 A FI 914266A FI 914266 A FI914266 A FI 914266A FI 88793 B FI88793 B FI 88793B
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radical
formula
compound
naphthoic acid
adamantyl
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FI914266A
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FI914266A0 (fi
FI88793C (sv
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Braham Shroot
Jean-Michel Bernardon
Jacques Eustache
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Cird
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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    • A61K8/42—Amides
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    • C07C235/66—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and singly-bound oxygen atoms, bound to the same carbon skeleton
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    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07C65/11—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic with carboxyl groups on a condensed ring system containing two rings
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    • C07C65/17—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
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    • C07C65/26—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic containing rings other than six-membered aromatic rings
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Claims (9)

1. Förfarande för framställning av ett fenylnaftalenderi-vat med den allmänna formeln:
10 R1 ][ Ί (i)
15 R3'^5;i5^/^ R5 där: - Rx betecknar: i) -C-R6 eller ii) -CH2OH 20 || 0 r · / - R6 betecknar en radikal -N eller en radikal -0R7, varvid 25 \ r' ' R7 betecknar en väteatom eller en lägre alkylradikal, r' och r" betecknar en väteatom, en lägre alkylradikal eller en aminosockerrest eller de bildar tillsammans en heterocykel,
30. R2 betecknar en väteatom, en grenad eller icke grenad al kylradikal med 1-15 kolatomer, en alkoxiradikal med 1-4 kol-atomer eller en cykloalifatisk radikal, - R3 betecknar en väteatom, en hydroxylradikal, en grenad eller icke grenad alkylradikal med 1-4 kolatomer, en alkoxi- 35 radikal med 1-10 kolatomer, en tiocykloalifatisk radikal eller en radikal med formeln -Ο-Si (CH3) 2-R8, där R8 betecknar en lägre alkylradikal, som är linjär eller grenad, - R4 och R5, identiska eller olika, betecknar en väteatom, en lägre alkylradikal, en hydroxiradikal eller en lägre acyl- 40 oxiradikal, eller ett sait av föreningen med formel I, 37 88793 kännetecknat av att ett magnesium-, litium- eller zinkderi-vat av en förening med fontein Xf 10 omsättes i ett vattenfritt lösningsmedelsmedium i närvaro av en katalysator som utgöres av en övergängsmetal eller ett komplex därav med en halogenförening av naftalen med formeln
15 R4 IIV)
20 R5 i vilka formler Rx-R5 har samma betydelser som ovan och X och Y är Cl, Br, F eller I; och, om sä önskas, utföres en eller flera av följande reaktioner: 25 i) en förening med formeln I, där Rx är -COOR7, där R7 är en alkylradikal, deesterifieras för bildande av motsvarande förening med formeln I, där Rx är -COOH, ... 30 ii) en förening med formeln I, där R3 är en radikal med formeln -Ο-Si (CH3) 2-R8, där R8 har samma betydelse som ovan, desilyleras för bildande av motsvarande förening med formeln I, där R3 är en hydroxiradikal, 35 iii) en förening med formeln I, där R3 är en hydroxiradikal, företras för bildande av motsvarande förening med formeln I, där R3 är en alkoxiradikal, 38 (S 793 iv) en förening med formeln I, där R4 och/eller R5 är en acyloxigrupp, deacyleras for bildande av motsvarande förening med formeln I, där R4 och/eller Rs är en hydroxigrupp, 5 v) en förening med formeln I, där Rx är -COOH, förestras för bildande av motsvarande förening med formeln I, där Rx är -C00R7, där R7 är en alkylradikal, vi) en förening med formeln I, där R4 och/eller R5 är en 10 hydroxiradikal, dehydroxyleras för bildande av motsvarande förening med formeln I, där R4 och/eller R5 är en väteatom, vii) en förening med formeln I, där Rx är -COOR7, där R7 är en alkylradikal, reduceras för bildande av motsvarande för- 15 ening med formeln I, där Rx är -CH2OH; viii) en förening med formeln I, där Rj^ är -COOH, amineras för bildande av motsvarande förening med formeln I, där r' 20 / Rx är -CON r", där r' och r" har samma betydelser som ovan. 25
2. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I, där alkylradika-len är metyl, etyl, isopropyl, butyl eller tert.-butyl. 30
3. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I, där alkoxiradika-len är metoxi, etoxi, isopropoxi, hexyloxi eller dekyloxi.
4. Förfarande enligt patentkravet 1, kännetecknat av att 35 man framställer en förening med formeln I, där den lägre acyloxiradikalen är acetyloxi eller propionyloxi.
5. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I, där den cykloali- 40 fatiska radikalen är 1-metylcyklohexyl eller 1-adamantyl. 39 ¢8 793
6. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I, där den tiocyklo-alofatiska radikalen är 1-adamantyltio. 5
7. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med formeln I, där den av radi-kalerna r' och r" tillsammans bildade heterocykeln är pipe-ridino, piperazino, morfolino eller pyrrolidino. 10
8. Förfarande enligt patentkravet 1, kännetecknat av att man framställer en förening med den allmänna formeln: - R'g 15 0 (II) där: *' betecknar en radikal Λ eller en radikal ·οκ'’· r" 25 r' och r", identiska eller olika, betecknar en väteatom, en lägre alkylradikal eller tillsammans bildar en morfolinora-dikal, R'7 betecknar en väteatom eller en lägre alkylradikal, R'2 betecknar en väteatom, en alkylradikal, en alkoxiradikal 30 eller en 1-adamantylradikal, och R'3 betecknar en väteatom, en hydroxylradikal, en alkylradikal, en alkoxiradikal eller en 1-adamantyltioradikal,
9. Förfarande enligt patentkravet 1, kännetecknat av att 35 man framställer: - 6-(3-metylfenyl)-2-naftoesyra eller dess metylester, - 6-(4-tert.-butylfenyl)-2-naftoesyra eller dess metylester, - 6-(3-tert.-butylfenyl)-2-naftoesyra eller dess metylester, - 6-(3,4-dimetoxifenyl)-2-naftoesyra eller dess metylester, 40 - 6-[p-(1-adamantyltio)-fenyl]-2-naftoesyra eller dess mety lester, 40 'G 793 - 6-[3 - (1-adamantyl)-4-metoxifenyl]-2-naftoesyra eller dess metylester, - metylestern av 6-[3-(1-adamanty1)-4-tert.-butyldimetylsi-lyloxifenyl]-2-naftoesyra, 5. metylestern av 6-[3-(1-adamantyl)-4-hydroxifenyl]-2-naf- toesyra, - 6-[3-(1-adamantyl)-4-hydroxifenyl]-2-naftoesyra, - metylestern av 6-[3-(1-adamantyl)-4-brom-l-dekyloxifenyl]-2-naftoesyra, 10 - 6-[3-(1-adamantyl)-4-dekyloxifenyl]-2-naftoesyra, - metylestern av 6-[3-(1-adamantyl)-4-hexyloxifenyl]-2-naf-toesyra, - 6-[3-(1-adamantyl)-4-hexyloxifenyl]-2-naftoesyra, - metylestern av 6-[3-(1-adamantyl)-4-metoxifenyl]-4-acet- 15 oxi-l-metyl-2-naftoesyra, - 6-[3-(1-adamantyl)-4-metoxifenyl]- 4-hydroxi-l-metyl-2-naf-toesyra, - metylestern av 6-[3-(1-adamantyl)-4-metoxifenyl]-4-hydr-oxi-l-metyl-2-naftoesyra, 20. metylestern av 6-[3-(l-adamantyl)-4-metoxifenyl]-l-metyl- 2-naftoesyra, - 6-[3-(1-adamantyl)-4-metoxifenyl]-l-metyl-2-naftoesyra, - 6-[3-(1-adamantyl)-4-metoxifenyl]-2-naftalen-metanol, - 6-[3-(l-adamantyl)-4-metoxifenyl]-2-naftoesyra-etylamid, 25 - 6-[3-(l-adamantyl)-4-metoxifenyl]-2-naftoesyra-morfolid, - metylestern av 6-(3-tert.-butyl-4-metoxifenyl)-2-naftoe-syra, - 6-(3-tert.-butyl-4-metoxifenyl)-2-naftoesyra, - metylestern av 6-[3-(1,1-dimetyldekyl)-4-metoxifenyl]-2-30 naftoesyra, - 6-[3-(1,1-dimetyldekyl)-4-metoxifenyl]-2-naftoesyra.
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FR2555571B1 (fr) * 1983-11-28 1986-11-28 Interna Rech Dermatolo Centre Derives du naphtalene, leur procede de preparation et leur application dans le domaine therapeutique
LU85849A1 (fr) * 1985-04-11 1986-11-05 Cird Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques
JPH01254659A (ja) * 1988-04-05 1989-10-11 Ss Pharmaceut Co Ltd ピロール誘導体

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US5183889A (en) 1993-02-02
US4717720A (en) 1988-01-05
JPH0830015B2 (ja) 1996-03-27
PT82361A (fr) 1986-05-01
DK162286D0 (da) 1986-04-10
EP0199636B1 (fr) 1989-02-08
ZA862733B (en) 1986-12-30
GR860948B (en) 1986-08-06
USRE34805E (en) 1994-12-06
NL300209I2 (nl) 2006-03-01
NO861413L (no) 1986-10-13
DE10199023I2 (de) 2003-01-09
NZ215779A (en) 1989-05-29
AU4796190A (en) 1990-05-10
NL300209I1 (nl) 2006-02-01
IE58882B1 (en) 1993-12-01
USRE34440E (en) 1993-11-09
PT82361B (pt) 1988-03-03
FI861510A0 (fi) 1986-04-09
AU5591286A (en) 1986-10-16
NO170627B (no) 1992-08-03
AU638223B2 (en) 1993-06-24
DE199636T1 (de) 1987-04-09
JPS61251632A (ja) 1986-11-08
EP0199636A1 (fr) 1986-10-29
IL78463A0 (en) 1986-08-31
US5212303A (en) 1993-05-18
IL78463A (en) 1990-04-29
ES554186A0 (es) 1987-06-01
FI914266A0 (fi) 1991-09-10
DE10199023I1 (de) 2001-06-21
FI88793C (sv) 1993-07-12
US5098895A (en) 1992-03-24
FI87762C (sv) 1993-02-25
ES8705845A1 (es) 1987-06-01
FI861510A (fi) 1986-10-12
FI87762B (fi) 1992-11-13
DE3662038D1 (en) 1989-03-16
DK172070B1 (da) 1997-10-13
NO170627C (no) 1992-11-11
LU85849A1 (fr) 1986-11-05
CA1266646A (fr) 1990-03-13
IE860931L (en) 1986-10-11
ATE40675T1 (de) 1989-02-15
DK162286A (da) 1986-10-12
AU595192B2 (en) 1990-03-29
US4940696A (en) 1990-07-10

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