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FI76078B - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1-piperazino-3-fenyl-indanderivat och vid foerfarandet anvaenda mellanprodukter. - Google Patents

Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1-piperazino-3-fenyl-indanderivat och vid foerfarandet anvaenda mellanprodukter. Download PDF

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Publication number
FI76078B
FI76078B FI810604A FI810604A FI76078B FI 76078 B FI76078 B FI 76078B FI 810604 A FI810604 A FI 810604A FI 810604 A FI810604 A FI 810604A FI 76078 B FI76078 B FI 76078B
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formula
group
compound
fluorophenyl
piperazine
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FI810604A
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English (en)
Finnish (fi)
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FI810604L (fi
FI76078C (sv
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Klaus Peter Boegesoe
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Kefalas As
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    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
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Claims (6)

1. Förfarande för framställning av terapeutiskt användbara l-piperazino-3-fenyl-indanderivat med formeln (I), 5 isomerer och farmaceutiskt godtagbara syraadditionssalter därav, -1— * Vr4
10 L Γ ] VV 6r^^>2' R2---f-R3 15 5%^3' 4' i vilken formeln R^ är väte, halogen, C^_^-alkyl, C^_^-alkoxi, C, .-alkylmerkapto, amino, acetamino, trifluormetyl eller •*·-4 2 3
20 C, ,-alkylsulfony, R och R betecknar väte, halogen, alkyl 1“4 * eller trifluormetyl och R är en rakkedjad eller förgrenad alkyl- eller alkenylgrupp, som har 1-6 kolatomer och som kan vara substituerad med en eller tvä hydroxylgrupper, en cyano-grupp, en acetaminogrupp, en C^g-cykloalkylgrupp, en eventu-25 elit med en halogenatom substituerad fenylgrupp eller en hyd- 4 roxi-substituerad cyklohexylgrupp, eller R är en grupp -CH2.CH2.N_y, där U är syre eller NH, eller en grupp -(CH2)n~CO.fenyl, där n är ett heltal 1-4 och fenylgruppen 30 kan vara substituerad med en halogenatom, varvid eventuella hydroxigrupper i föreningarna med formeln (I) kan vara för-estrade med en alifatisk C2_2ij-karboxylsyra, känne-t e c k n a t därav, att a) en förening med formeln 35 57 76078 „i f^\-Γχ —t JL J (II) 5 /X r2—ί 4- r3 12 3 där R , R och R betecknar samma som ovan och X är halogen, 2o företrädesvis klor, eller -OSOjR, där R är CH^ eller CH3~~^ ^— , omsätts med ett piperazinderivat med formeln 15 / \ 4 ^n.r 4 där R betecknar samma som ovan, eller b) en förening med formeln 20 _ f\h (III) r1-^- |l \_/
25 I^S) R2--Jp 12 3 där R , R och R betecknar samma som ovan, omsätts med en 4 4 förening med formeln R .X, där R och X betecknar samma som 30 ovan, eller ·*. 5 5 med en epoxid med formeln CH------ CH-R , där R är lägre alkyl eller hydroxialkyl, eller 6 7 6 med en aldehyd eller ett keton med formeln R -CO-R , där R ^ är väte eller lägre alkyl och R^ är en lägre alkyl eller 58 7 6 0 7 8 alkylengrupp, som kan vara substituerad med fenyl eller subs-tituerad fenyl genom att använda NaCNBH^ som reduktionsmedel, eller c) en förening med formeln 5 ° ·!-0-'! där R , R och R betecknar samma som ovan och R är en rakked-jad eller förgrenad alkylgrupp, som har 1-5 kolatomer och som kan vara substituerad med en eller tvä eventuellt skyddade hydr-oxylgrupper, en C3_6cykloalkylgrupp, en eventuellt med en halo-genatom substituerad fenylgrupp eller en hydroxi-substituerad cyklohexylgrupp, där hydroxylgruppen kan vara skyddad, reduce- 2Q ras, eller d) en förening med formeln -rO'Y 25 ^V^—OH (V) 2 x' II 3 R —k -J- R 12 3 30 där R , R och R betecknar samma som ovan och Y är en rakked-jad eller förgrenad alkylgrupp, som har 1-6 kolatomer och som kan vara substituerad med en C^^cykloalkylgrupp eller en eventuellt med en halogenatom substituerad fenylgrupp, reduce-ras, eller 35 e) en förening med formeln II 59 76078 r1_—Γ(_>4
5 TT (VI) R2---J- R3 12 3 4 10 där R , R , R och R betecknar samma som ovan, reduceras 1 närvaro av en metallkatalysator, eller f) en förening med formeln , OrjO-· (VII) R2---|—R3 20 1 2 3 4 · där R , R och R betecknar samma som ovan och R är en rak- kedjad eller förgrenad alkyl- eller alkenylgrupp innehillande en eller flera ester-, keton- eller aldehydgrupper, reduceras 25 med ett lämpligt redukstionsmedel till en motsvarande förening med formeln (I) innehällande en eller flera hydroxigrupper; och, om sä önskas, förestras eventuella hydroxigrupper i en erhällen förening med formeln (I) med ett reaktivt derivat av en alifatisk C2_24~karboxylsyra och /eller uppdelas en före- 30 ning med formeln (I) i isomerer och/eller omvandlas en förening med formeln (I) till ett farmaceutiskt godtagbart syra-additionssalt. 60 7 6 0 7 8
2. Förfarande enligt patentkravet 1, k ä n n e - t e c k n a t därav, att man framställer en förening med formeln (I), där R* är i 6-ställning och betecknar fluor, trifluormetyl, klor, metyl eller metylmerkapto i 6-ställning, 5 R2 är fluor i 4'-ställning, R^ är väte och R^ är metyl, 2-hydroxietyl, 2,3-dihydroxipropyl, 4-hydroxibutyl, 1,3-di-hydroxi-2-propyl eller β-hydroxipropyl.
3. Förfarande enligt patentkravet 1 eller 2, k ä n -netecknat därav, att man framställer 10 1-(2-hydroxietyl)-4-£3-(4'-fluorfenyl)-6-trifluormetyl- l-indanyl7piperazin, 1-(2-hydroxietyl)4-£3-(4·-fluorfenyl)-6-fluor-l-inda-nyl7piperazin, 1-(4-hydroxibutyl)-4-£3-(4'-fluorfenyl)-6-fluor-l-inda- 15 nyl7piperazin, l-isopropyl-4-£3-(41-fluorfenyl)-6-metyl-l-indanyl7-piperazin, eller 1-(3-hydroxipropyl)-4-£3-(4'-fluorfenyl)-6-klor-l-in- danyl7piperazin, 20 eller en isomer eller ett farmaceutiskt godtagbart syraaddi-tionssalt av dessa.
4. Förfarande enligt patentkravet 1, k ä n netecknat därav, att man framställer en förening med formeln (I), där R* är väte, R2 är 3'-klor, R^ är 4'-klor 25 och R^ är metyl, 2-hydroxietyl, 2,3-dihydroxipropyl eller 4-hydroxibutyl.
5. Förfarande enligt patentkravet 1 eller 4, k ä n -netecknat därav, att man framställer 1-(2-hydroxietyl)-4-£3“(31,4'-diklorfenyl)indanyl7~ 30 piperazin eller l-metyl-4-£3'-(3',4'-diklorfenyl)-l-indanyi7piperazin eller en isomer eller ett farmaceutiskt godtagbart syraaddi-tionssalt av dessa.
FI810604A 1980-02-29 1981-02-26 Förfarande för framställning av nya terapeutiskt användbara 1-piperazi no-3-fenyl-indanderivat och vid förfarandet använda mellanprodukter FI76078C (sv)

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GB8006931 1980-02-29
GB8006931 1980-02-29

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FI810604L FI810604L (fi) 1981-08-30
FI76078B true FI76078B (fi) 1988-05-31
FI76078C FI76078C (sv) 1988-09-09

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FI810604A FI76078C (sv) 1980-02-29 1981-02-26 Förfarande för framställning av nya terapeutiskt användbara 1-piperazi no-3-fenyl-indanderivat och vid förfarandet använda mellanprodukter

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US (1) US4443448A (sv)
EP (1) EP0035363B1 (sv)
JP (1) JPS56167670A (sv)
AT (1) ATE13056T1 (sv)
AU (1) AU538424B2 (sv)
CA (1) CA1181750A (sv)
DE (1) DE3170245D1 (sv)
DK (1) DK162992C (sv)
ES (1) ES499870A0 (sv)
FI (1) FI76078C (sv)
GB (1) GB2071088B (sv)
IE (1) IE50867B1 (sv)
IL (1) IL62152A (sv)
NO (1) NO156690C (sv)
NZ (1) NZ196284A (sv)
ZA (1) ZA811223B (sv)

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IL66831A0 (en) * 1981-10-05 1982-12-31 Kefalas As Indane derivatives
FR2530236B1 (fr) * 1982-07-16 1985-08-02 Delalande Sa Nouveaux derives aminoalkyl naphtaleniques, leurs sels d'addition d'acide et le procede de preparation ainsi que l'application en therapeutique de ces derives et sels
IE55972B1 (en) * 1982-10-07 1991-03-13 Kefalas As Phenylindene derivatives,acid addition salts thereof,and methods of preparation
GB8427125D0 (en) * 1984-10-26 1984-12-05 Lundbeck & Co As H Organic compounds
IE58370B1 (en) * 1985-04-10 1993-09-08 Lundbeck & Co As H Indole derivatives
GB8628644D0 (en) * 1986-12-01 1987-01-07 Lunbeck A S H Intermediates
JPS63239220A (ja) * 1987-03-27 1988-10-05 Taiyo Yakuhin Kogyo Kk 脳循環代謝改善剤
US5643784A (en) * 1990-12-04 1997-07-01 H, Lundbeck A/S Indan derivatives
DK286990D0 (da) * 1990-12-04 1990-12-04 Lundbeck & Co As H Indanderivater
NZ243065A (en) 1991-06-13 1995-07-26 Lundbeck & Co As H Piperidine derivatives and pharmaceutical compositions
CA2091204C (en) * 1992-03-11 1997-04-08 Ronald J. Mattson Antiischemic-piperazinyl and piperidinyl-cyclohexanes
DK55192D0 (da) * 1992-04-28 1992-04-28 Lundbeck & Co As H 1-piperazino-1,2-dihydroindenderivater
DK78692D0 (da) * 1992-06-12 1992-06-12 Lundbeck & Co As H Dimere piperidin- og piperazinderivater
EP1640359A3 (en) * 1997-12-10 2006-04-05 Nps Pharmaceuticals, Inc. Anticonvulsant and central nervous system-active bis(fluorophenyl)alkylamides
DE69832302D1 (de) * 1997-12-10 2005-12-15 Nps Pharma Inc Antikonvulsive und zns-aktive bis-fluoralkylamide
CA2317591A1 (en) 1998-01-09 1999-07-15 Pharm-Eco Laboratories Inc. Synthesis of 3-aryl-1-indanamines
DE69910706T2 (de) * 1998-05-26 2004-07-08 Pfizer Products Inc., Groton Medikament zur Behandlung von Glaukoma und ischämischer Retinopathie
US6525206B1 (en) * 2000-10-17 2003-02-25 President And Fellows Of Harvard College Compounds with high monoamine transporter affinity
RS20060121A (en) * 2003-08-18 2008-09-29 H.Lundbeck A/S., Succinate and malonate salt of trans-4-(1r,3s)-6-chloro-3- phenylindan-1-yl)-1,2,2-trimethylpiperazine and the use as a medicament
EP1658276B1 (en) * 2003-08-18 2012-10-10 H. Lundbeck A/S Trans-1(6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine
CA2597620A1 (en) * 2005-02-16 2006-08-24 H. Lundbeck A/S Tartrate and malate salts of trans-1-((1r,3s)-6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine
TWI453198B (zh) * 2005-02-16 2014-09-21 Lundbeck & Co As H 製造反式-1-((1r,3s)-6-氯基-3-苯基茚滿-1-基) -3 , 3 -二甲基六氫吡與其鹽類之方法及製造4-((1r , 3s）-6 -氯基-3-苯基茚滿-1-基 )-1,2,2-三甲基六氫吡與其鹽類之方法
TWI376373B (en) * 2005-02-16 2012-11-11 Lundbeck & Co As H Crystalline base of a pharmaceutical compound
KR20110021754A (ko) * 2008-05-07 2011-03-04 하. 룬드벡 아크티에셀스카브 인지 결함 치료 방법
EA201170512A1 (ru) * 2008-10-03 2011-08-30 Х. Лундбекк А/С Композиция для перорального введения
KR101879474B1 (ko) 2011-06-20 2018-07-17 하. 룬드벡 아크티에셀스카브 정신 분열증의 치료를 위한 중수소화 1-피페라지노-3-페닐 인단
USD995517S1 (en) * 2021-02-22 2023-08-15 Dell Products L.P. Storage drive enclosure

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DE2021262A1 (de) * 1970-04-30 1971-11-11 Cassella Farbwerke Mainkur Ag Piperazinderivate
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Also Published As

Publication number Publication date
FI810604L (fi) 1981-08-30
ES8205404A1 (es) 1982-06-01
GB2071088B (en) 1983-08-24
DK92781A (da) 1981-08-30
AU538424B2 (en) 1984-08-16
CA1181750A (en) 1985-01-29
ES499870A0 (es) 1982-06-01
EP0035363A1 (en) 1981-09-09
DK162992C (da) 1992-06-01
IE50867B1 (en) 1986-08-06
US4443448A (en) 1984-04-17
NO810684L (no) 1981-08-31
IL62152A0 (en) 1981-03-31
EP0035363B1 (en) 1985-05-02
ZA811223B (en) 1982-04-28
IE810315L (en) 1981-08-29
NZ196284A (en) 1983-12-16
JPH0224819B2 (sv) 1990-05-30
AU6791781A (en) 1982-09-16
DE3170245D1 (en) 1985-06-05
DK162992B (da) 1992-01-06
IL62152A (en) 1985-03-31
NO156690C (no) 1987-11-04
JPS56167670A (en) 1981-12-23
ATE13056T1 (de) 1985-05-15
NO156690B (no) 1987-07-27
GB2071088A (en) 1981-09-16
FI76078C (sv) 1988-09-09

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