FI111639B - Förfarande för framställning av nya, terapeutiskt användbara piperazin- och piperidinderivat - Google Patents

Förfarande för framställning av nya, terapeutiskt användbara piperazin- och piperidinderivat Download PDF

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FI111639B
FI111639B FI932104A FI932104A FI111639B FI 111639 B FI111639 B FI 111639B FI 932104 A FI932104 A FI 932104A FI 932104 A FI932104 A FI 932104A FI 111639 B FI111639 B FI 111639B
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FI932104A
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FI932104A0 (fi
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Allen B Reitz
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Mcneilab Inc
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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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Claims (22)

1. Förfarande för framställning av nya, tera-peutiskt användbara piperazin- och piperidinderivat med 5 formeln I Rw f ΓΪ1 /rv JL\[J -R8
2. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer en förening med formeln I, väri Ar är bensofuran eller en grupp med for- 10 mein h.
3. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer en förening med formeln I, väri Ar är en med en Ci_8-alkoxylgrupp substituerad fenylgrupp, A är N, n är 0 och R1, R2, R3 och
15 R4 är H-atomer.
4. Förfarande enligt patentkrav 3, känne-t e c k n a t därav, att Ci-8-alkoxylgruppen är isopro-poxylgruppen.
5. Förfarande enligt patentkrav 1, känne- 20 tecknat därav, att man framställer en förening med formeln I, väri R8 och R9 bildar tillsammans en grupp som är -(CH2)q-, väri g är 3 - 7, - (CH2) 2-0- (CH2) 2~ eller -(CH2)2-N- (CH2) 2- .
6. Förfarande enligt patentkrav 1, känne- ’ 25 tecknat därav, att man framställer en förening med formeln I, väri R8 och R9 bildar tillsammans gruppen med formeln c.
7. Förfarande enligt patentkrav 1, känne- tecknat därav, att man framställer en förening med . 30 formeln I, väri Ar är substituerad med en eller flera • · > - Ci-8-alkyl-, Ci-8-alkoxyl- eller halogengrupper.
8. Förfarande enligt patentkrav 1, känne-tecknat därav, att man framställer en förening med formeln Ia 35 111639 ί R12 # vari R8 och R9 betecknar samma som i patentkrav 1 och R12 och R13 är H, Ci-8-alkyl, Ci-8-alkoxyl, cyan 10 eller halogen, eller ett farmaceutiskt godtagbart syraad-ditionssalt därav.
9. Förfarande enligt patentkrav 8, kanne-t e c k n a t därav, att R12 är en Ci-8-alkoxylgrupp.
10. Förfarande enligt patentkrav 8, kanne-15 tecknat därav, att R8 och R9 bildar tillsammans en grupp som definierats i patentkarav 1.
10. I / (I) M/ R3R4 li H R7 väri
15 A är N eller CH; W är C eller SO; R1 och R2 är H-atomer eller Ci_4-alkylgrupper; n är 0 - 4; R3 och R4 är antingen boda H-atomer eller den ena 2 0 av dem är H och den andra är en Ci-4-alkyl- eller hydroxyl-grupp eller tillsammans de är syre, varvid bildas en kar-bonylgrupp, under förutsättning att när n är 0, dä kan R3 och R4 inte tillsammans vara syre; R5 är H, Ci-e-alkoxyl, nitro, amino eller Ci-8- » 25 alkylamido; R7 är 0 eller S, när W är C, eller R7 är O, när W är SO; R8 och R9 är oberoende av varandra H, Ci-8-alkyl, eventuellt aminoskyddad amino-Ci-e-alkyl, med halogen 30 substituerad fenyl, fenyl-Ci-8-alkyl, Ci-8-alkylkarbonyl, . ’* C3-i0-cykloalkyl eller N-Ci-8-alkylpyrrolidinyl-Ci.8-alkyl ; eller R8 och R9 bildar tillsammans gruppen -(CH2)q-, väri q är 3 - 7 och vilken är eventuellt substituerad med 35 en eller flera grupper som valts ur gruppen Ci-8-alkyl, -COOH, -C02 (Ci.8-alkyl) , -C02 (Ci-e-alkyl) fenyl, - (Ci-8- 111639 alkyl)-OH, =0 och -OH eller gruppen - (CH2) 2-0- (CH2) 2- eller gruppen - (CH2) 2-N-(CH2) 2-, vars N-atom är substituerad med en grupp som valts ur gruppen som bestär av eventuellt med Ci-e-alkoxi eller trifluormetyl substituerad fenyl, fenyl-5 Ci-e-alkyl och -C02 (Ci_8-alkyl) , eller gruppen med formeln ^ <0 . o0 . <D · Φ (a) (b) (c) (d) (e) 10 eller ^ , väri R är Ci-8-alkyl, och Ar är fenyl, fenyl som är substituerad med en eller flera Ci-8-alkyl-, hydroxi-Ci-8-alkoxyl- , Ci_8-alkoxyl. , 15 trifluormetyl-, cyan-, halogen- eller nitrogrupper, pyri-midinyl, pyridinyl, naftyl, bensofuranyl, bensodioxanyl eller en grupp med formeln <V (g) eller <O]0f (h) 20 {_} ° under förutsättning att när A är kväve, R1, R2 och R5 är väten, R3 och R4 är boda H-atomer eller den ena av dem är H och den andra är en hydroxylgrupp eller tillsammans de är syre, R8 och R9 är oberoende av varandra väte eller 25 Ci-4-alkyl, n är 0 - 3, W är SO och R7 är O, dä är Ar annan än pyridinyl, samt farmaceutiskt godtagbara salter därav, kännetecknat därav, att a) en förening med formeln VI 30 " RY. ir*] (VI X(CH2)/A^\w.x
35 R7 111639 väri X är halogen, m är n+1 och n, R5, R7 och W betecknar samma som ovan, omsätts med ett amin med formeln R8R9NH 5 väri R8 och R9 betecknar samma som ovan, i närvaro av en bas och därefter med ett piperazin- eller piperidinderivat med formeln VII R1 10 rL AtVnH <VII> \~y R2 15 väri A, Ar, R1 och R2 betecknar samma som ovan, i närvaro av en bas; b) en förening med formeln 20 R5 Ji g pe X-(CH2)^W-n: q r7 R9 25 väri X är halogen, m är n+1 och n, R5, R7, R8 och R9 betecknar samma som ovan, omsätts med ett piperazin- eller piperidinderivat med formeln VII, väri A, Ar, R1 och R2 betecknar samma som ovan, i närvaro av en bas/ 30 c) en förening med formeln IX • * < /—^ Ar- H {6H^mf^Br)Ph (IX) 35 väri A, Ar och m betecknar samma som ovan, utsätts tili koppiing med kolmonoxid och ett amin med formeln 111639 r8r9nh väri R8 och R9 betecknar samma sora ovan, vilken koppling 5 sker med hjälp av palladium, för att erhälla en förening med formeln X Ar-^N-(CH ÄtQ-SiT (X) 10 ™ väri A, Ar, m, R8 och R9 betecknar samma som ovan; d) en förening med formeln XXIII
15 O /-\ i! Ar-AN«{CH2)fp^x^ (XXIII) 2. väri X är halogen och A, Ar och n betecknar samma som i formeln I, utsätts till koppling med kolmonoxid och ett amin med formeln R8R9NH 25 väri R8 och R9 betecknar samma som ovan, vilken koppling sker med hjälp av palladium, för att erhälla en förening med formeln XXIV 30 /-V II ·; Ar-A^tCH^-CX^ p (elv) Rs/ 35 väri A, Ar, n, R8 och R9 betecknar samma som ovan; e) en förening med formeln XXIX 111659 /Ι”Λ (XXIX) Ar-A/ N-CH^^ \-| J R3 R2 ' 5 väri A, Ar, R1, R2 och R3 betecknar sarana som i formeln I, omsätts med ett amin med formeln R8R9NH 10 väri R8 och R9 betecknar samma som ovan, för att erhälla en förening med formeln XXX R1 ^ /RS /~l~\ J -fj— C-N is Ar-A7 N-CH-V U R9 . <xxx> \_|y rS ° R2 väri A, Ar, R1, R2, R3, R8 och R9 betecknar samma som ovan; och 2. i) eventuellt en amid med formeln XXIV, vari A, Ar, n, R8 och R9 betecknar samma som ovan, reduceras till en motsvarande alkohol med formeln XXV OH
25 Ar-A/_^(CH2)rtCH 0 (χχν> v-v T h-c: N-R8 Rs/ ii) ) eventuellt en alcohol med formeln XXV, vari 30 A, Ar, n, R8 och R9 betecknar samma som ovan, hydrogeneras *· katalytiskt för att erhälla en motsvarande förening med formeln XXVI Α,-Α^Ν-ίΟΗ^ηί^».^8 OTVI)
35 Nf H9 111639 iii) eventuellt en förening med forraeln I, väri A, Ar, R1, R2, R3, R4, R5, R7, n och W betecknar samma som ovan i samband med formeln I och R8 och R9 bildar tillsammans gruppen -(CH2)q-, väri q är 3 - 7 och vilken är substi-5 tuerad med en grupp som är -C02 (Ci-8-alkyl) , hydrolyseras till en motsvarande syra med formeln I, väri A, Ar, R1, R2, R3, R4, R5, R7, n och W betecknar samma som ovan och R8 och R9 bildar tillsammans gruppen -(CH2)q-, väri q är 3 - 7 och vilken är substituerad med en grupp som är -COOH; 10 iv) eventuellt avläggsnas skyddsgruppen(skydds- grupperna) ur en förening med formeln I, väri A, Ar, R1, R2, R3, R4, R5, R7, n och W betecknar samma som ovan i samband med formeln I och ätminstone den ena av grupperna R8 och R9 är aminoskyddad amino-Ci-8-alkyl, varvid erhälls en 15 motsvarande förening med formeln I, väri A, Ar, R1, R2, R3, R4, R5, R7, n och W betecknar samma som ovan och ätminstone den ena av grupperna R8 och R9 är amino-Ci.8-alkyl ; v) eventuellt en förening med formeln I, vari A, Ar, R1, R2, R3, R4, R5, R7, n och W betecknar samma som ovan 20. samband med formeln I och R8 och R9 bildar tillsammans gruppen med formeln c, omvandlas genom syrasolvolys till en motsvarande förening med formeln I, väri A, Ar, R1, R2, R3, R4, R5, R7, n och W betecknar samma som ovan och R8 och R9 bildar tillsammans gruppen - (CH2) 2-C0- (CH2) 2-; 25 vi) eventuellt en förening med formeln I, vari A, Ar, R1, R2, R3, R4, R7, R8, R9, n och W betecknar samma som ovan i samband med formeln I och R5 är nitro, reduceras till en motsvarande förening med formeln I, vari R5 är amino; 30 vii) eventuellt en förening med formeln I, vari • A, Ar, R1, R2, R3, R4, R7, R8, R9, n och W betecknar samma som ovan i samband med formeln I och R5 är amino, acyleras till en motsvarande förening med formeln I, vari R5 är Ci-8-alkylamido; eller 35 viii) eventuellt en förening med formeln I, vari A, Ar, R1, R2, R3, R4, R5, R8, R9 och n betecknar samma som 111639 ovan i samband med formeln I, W är C och R7 är 0, omvand-las med hjälp av 2,4-bis(4-metoxifenyl)-l,3-ditia-2,4-difosfetan-2,4-disulfid till en motsvarande förening med formeln I, väri R7 är S; och 5 eventuellt föreningen med formeln I tillvaratas i form av ett farmaceutiskt godtagbart salt därav.
11. Förfarande enligt patentkrav 1, kanne-tecknat därav, att man framställer l-{3-{{4-[2-(1-metyletoxi)fenyl]-l-piperazinyl}metyl}bensoyl}piperidin- 20 succinat.
12. Förfarande enligt patentkrav 1, kanne-tecknat därav, att man framställer hexahydro-1-{3-{{4-[2-(1-metyletoxi)fenyl]-l-piperazinyl}metyl}bensoyl}-lH-azepinmonohydroklorid. * 25
13. Förfarande enligt patentkrav 1, kanne- tecknat därav, att man framställer l-{3-{ [4-(1,4-bensodioxan-5-yl)-1-piperazinyl]metyl}bensoyl}piperidin-perklorat (5:7).
14. Förfarande enligt patentkrav 1, k ä n n e - . 30 tecknat därav, att man framställer 1-{2-{{4-[2-(1- metyletoxi)fenyl]-1-piperazinyl]metyl}bensoyl}piperidindi- i hydroklorid.
15. Förfarande enligt patentkrav 1, känne-tecknat därav, att man framställer l-{3-{{4-[2-(1- 35 metyletoxi)fenyl]-1-piperazinyl]metylJbensoyl}-2,6-di-metylpiperidinhydroklorid (3:2).
FI932104A 1991-09-11 1993-05-10 Förfarande för framställning av nya, terapeutiskt användbara piperazin- och piperidinderivat FI111639B (sv)

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HU9301361D0 (en) 1993-09-28
CA2095826A1 (en) 1993-03-12
DK0563345T3 (da) 2002-10-14
ES2179822T3 (es) 2003-02-01
EP0563345A4 (en) 1994-09-28
RU2139867C1 (ru) 1999-10-20
EP0562049A1 (en) 1993-09-29
CA2095847A1 (en) 1993-03-12
JP2941945B2 (ja) 1999-08-30
AU1363392A (en) 1993-04-05
FI932104A0 (fi) 1993-05-10
FI932104A (fi) 1993-05-10
EP0562049A4 (en) 1994-09-28
AU657799B2 (en) 1995-03-23
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EP0563345A1 (en) 1993-10-06
HU9301362D0 (en) 1993-09-28
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ATE219938T1 (de) 2002-07-15
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DE69232665D1 (de) 2002-08-08
NO931694D0 (no) 1993-05-10
NO931695D0 (no) 1993-05-10
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EP0563345B1 (en) 2002-07-03
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PT99700A (pt) 1993-03-31
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