FI109691B - Förfarande för framställning av piperidinderivat och en regioisomer till användning i förfarandet - Google Patents

Förfarande för framställning av piperidinderivat och en regioisomer till användning i förfarandet Download PDF

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FI109691B
FI109691B FI956270A FI956270A FI109691B FI 109691 B FI109691 B FI 109691B FI 956270 A FI956270 A FI 956270A FI 956270 A FI956270 A FI 956270A FI 109691 B FI109691 B FI 109691B
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formula
substantially pure
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FI956270A0 (sv
FI956270A (sv
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Ambra Thomas E D
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Albany Molecular Res Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—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
    • C07D211/08—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
    • C07D211/18—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
    • C07D211/20—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/14—Decongestants or antiallergics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/86—Unsaturated compounds containing keto groups containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—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
    • C07D211/08—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
    • C07D211/18—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
    • C07D211/20—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—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
    • C07D211/08—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
    • C07D211/18—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
    • C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pulmonology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Immunology (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (20)

1 I /^λΙ (CHj )3-C-^___-C-COOH ch3
20. Förening som har formeln: Wh-·. <J CH3 kännetecknad av att
1. Förfarande för framställning av piperidinderivatför-eningar enligt formeln: B fr ,u^r, ch3 5 där Rl är väte eller hydroxi; R2 är väte; eller Rx och R2 tillsammans bildar en andra bindning mellan de kolatomer vid vilka Rx och R2 är bundna; '···* R3 är -COOH eller -C00R4; ‘••10 R4 har 1-6 kolatomer; /·· A är väte, B och D är substituenter i sinä respektive rin- gar, vilka substituenter var och en kan vara lika eller olika och de är väte, en halogen, alkyl, hydroxi eller alkoxi, kännetecknat av att nämnda förfarande innefattar 15 att: : man tillhandahäller en väsentligen ren regioisomer med formeln: <1 cH» . och omvandlar denna väsentligen rena regioisomer tili ett pipe-20 ridinderivat med en piperidinförening som har formeln: S4 109691 & H
2. Förfarande enligt patentkrav 1, kännetecknat av att nämnda tillhandahällande innefattar att man: acylerar en utgängsförening med formeln: A CH3 C-COR, CH, 5 3 där R5 är -ORg, -N(R6)2 och -SR6, och R6 är en alkyl med 1-6 kolatomer, med en förening som har formeln Cl cox " 10 ^ där :: X är en halogen, : under betingelser vid vilka man ästadkommer en forsta blandning av regioisomerer med formeln: :./ a ch3 '·*: C0Rs
15. CHl ; :··· hydrolyserar den första blandningen av regioisomerer under betingelser vid vilka man ästadkommer en andra blandning av regioisomerer med formeln: 55 109691 0 ch3 ; och utvinner ur den andra blandningen av regioisomerer en subs-tantiellt ren regioisomer med formeln: O * fH3 —j5—cooh ^ CHj 5
3. Förfarande enligt patentkrav 2, kännetecknat av att nämnda utvinning innefattar att: man ur den andra blandningen av regioisomerer kristalli-serar ett substantiellt rent regioisomersalt med formeln: o : ?H» —j5-00®·χ’ ^ CH, 10 : : där X+ är Lewis' syra; . : isolerar det substantiellt rena regioisomersaltet; och omvandlar det substantiellt rena regioisomersaltet till en ” 15 substantiellt ren regioisomer med formeln: l ..: < ch3
4. Förfarande enligt patentkrav 3, kännetecknat av att X+ är ett alkalimetallsalt eller ett ammoniumsalt av formen „ 109691 NR7R8R9 där R7, Rg och R9 var för sig är väte eller en alkyl med 1 tili 6 kolatomer och rak eller förgrenad kedja, eller en alkyl som i vilken som heist position är substituerad med en fenylring eller en substituerad fenylring. 5 5. Förfarande enligt patentkrav 4, kannetecknat av att X+ är kinkonidin.
6. Förfarande enligt patentkrav 2, kännetecknat av att nämnda acylering utförs med en Friedel-Crafts-reaktion med användning av A1C13 som katalysator. 10 7. Förfarande enligt patentkrav 1, kännetecknat av att nämnda tillhandahällande innefattar att man: acylerar en utgängsförening med formeln: CH3 med en f örening som har formeln: ci—c=o „ λ där X]_ är en halogen, trialkyltenn, trialkylborat, triflat eller ·,· ndgon substituent som är användbar vid kopplingsreaktioner • » som baserar sig pä användning av organometalliska •( 20 föreningar, under betingelser, vid vilka man ästadkommer en ·' substantiellt ren regioisomer med formeln: a y&h <J CH3 109691
8. Förfarande enligt patentkrav 1, kännetecknat av att nämnda tillhandahällande innefattar att man: acylerar en utgängsförening med formeln: CH3 5 där R5 är -ORg, -N(Rg)2 och -SRg, och Rg är en alkyl med 1 - 6 kolatomer, med en förening med formeln Cl—c=o λ 10 under betingelser vid vilka man ästadkommer en första blandning av regioisomerer med formeln: *··. A CH3 i: “hs I ^ hydrolyserar den första blandningen av regioisomerer under betingelser vid vilka man ästadkommer en andra blandning av 15 regioisomerer med formeln: : „ A CH, ^ ch> ; OCh utvinner ur den andra blandningen av regioisomerer en sub-stantiellt ren regioisomer med formeln: 109691 VÖ-P' <1 CH>
9. Förfarande enligt patentkrav 8, kännetecknat av att nämnda tillhandahällande innefattar att man kristalliserar ett substantiellt rent regioisomersalt med formeln: O i -c—coo- X- ^ CH, 5 3 ur den andra blandningen av regioisomerer; isolerar det substantiellt rena regioisomersaltet; och omvandlar det substantiellt rena regioisomersaltet tili en substantiellt ren regioisomer med formeln: _ a CH- \\ I y0—“U )/-C-COOH 4 ’•..10 CH3 •| 10. Förfarande enligt patentkrav 9, kännetecknat av att X+ är ett alkalimetallsalt eller ett ammoniumsalt av formen NR7R8R9 där R7, R8 och R9 är väte eller en alkyl med 1 tili » · 6 kolatomer och rak eller förgrenad kedja, eller en alkyl 15 som i vilken som heist position är substituerad med en : fenylring eller en substituerad fenylring. t »
11. Förfarande enligt patentkrav 10, kännetecknat av att X+ är kinkonidin. I i ··’ 12. Förfarande enligt patentkrav 8, kännetecknat av att 20 nämnda acylering utförs med en katalysator som innehäller ··* palladium, nickel eller en blandning av dessa.
13. Förfarande för framställning av ett hydroxylerat piperi-dinderivat enligt formeln: 59 1 0 9 6 91 B 6" Γ nL Γ3 (CH2)3-CH—-j>-R3 ch3 där Rl är väte eller hydroxi; R2 är väte; eller Rl och R2 tillsaminans bildar en andra 5 bindning mellan de kolatomer vid vilka Rl och R2 är bundna; R3 är -COOH eller -COOR4; R4 har 1-6 kolatomer; A är väte, B och D är substituenter i sinä respektive ringar, vilka 10 substituenter var och en kan vara lika eller olika och de är väte, en halogen, alkyl, hydroxi eller alkoxi, kännetecknat ...· av att nämnda förfarande innefattar att: man tillhandahäller en väsentligen ren regioisomer med formeln: 'i WM-- :: <| ch3 15 och omvandlar denna väsentligen rena regioisomer med en * , ’i piperidinförening som har formeln: 3 09 :·. JL; a O' N H 20 tili ett piperidinderivat med formeln: B 60 109691 6" I li rl Γ* CHg där substituenterna är som definierats ovan, och reducerar detta under betingelser vid vilka nämnda 5 hydroxylerade piperidinderivat bildas.
14. Förfarande enligt patentkrav 13, kännetecknat av att det hydroxylerade piperidinderivatet har formeln: pp ... OH \ / oh ch, Ϊ ,L.,.-|_0_p ·*: h ch3 , . 10 15. Förfarande enligt patentkrav 13, kännetecknat av att det * · hydroxylerade piperidinderivatet har formeln: • t • · · > · • · » · 6i 109691 ch3 ch3 Qd> ^c—OH Ö ?h ?«» 1 i (CHj ) 3 C C COOH CH3
16. Förfarande enligt patentkrav 1, kännetecknat av att nämnda omvandling innefattar att: man halogenerar den substantiellt rena regioisomeren son 5 har formeln: )44- <\ ch3 It· I · · \ under betingelser vid vilka det bildas en första mellanpro- >. ; duktsförening med formeln: • · I · f ?h3 i; o CH;* » I · *· [ 10 där ·': X är en halogen och » later den första mellanproduktsföreningen reagera med en I · piperidinförening med formeln: • » » » » > 62 109691 έιβ' & N H under betingelser vid vilka det bildas ett piperidinderivat med formeln: B -Ap ' ch3 5 17. Förfarande enligt patentkrav 1, kännetecknat av att * nämnda omvandling innefattar att man: läter en substantiellt ren regioisomer som har formeln: ··; <1 CH> reagera med en piperidinförening med formeln: B 109691 & N H under betingelser vid vilka det bildas ett piperidinderivat med formeln: B 6" CH3 • · .5 18. Förfarande enligt patentkrav 1, kännetecknat av att ’piperidinderivatet har formeln: :¾ QP -OH I jj (cw2)3 -cooh ch3
19. Förfarande enligt patentkrav 1, kännetecknat av att piperidinderivatet har formeln: 109691 ch3 ch3 op ^c—OH Ö ?« ?h»
5 R3 är -COOH eller -COOR4; •"S R4 är en alkyl med 1-6 kolatomer; : A är väte. #
FI956270A 1993-06-24 1995-12-27 Förfarande för framställning av piperidinderivat och en regioisomer till användning i förfarandet FI109691B (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US8310293A 1993-06-24 1993-06-24
US8310293 1993-06-24
US9406873 1994-06-21
PCT/US1994/006873 WO1995000482A1 (en) 1993-06-24 1994-06-21 Piperidine derivatives and process for their production

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FI956270A0 FI956270A0 (sv) 1995-12-27
FI956270A FI956270A (sv) 1995-12-27
FI109691B true FI109691B (sv) 2002-09-30

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US (9) US5750703A (sv)
EP (4) EP1369409B1 (sv)
JP (4) JP3034047B2 (sv)
KR (2) KR100387347B1 (sv)
AT (3) ATE174589T1 (sv)
AU (1) AU670004B2 (sv)
CA (1) CA2147126C (sv)
DE (3) DE69434696T2 (sv)
DK (3) DK1369409T3 (sv)
ES (3) ES2211444T3 (sv)
FI (1) FI109691B (sv)
HU (1) HU226559B1 (sv)
NO (2) NO308599B1 (sv)
NZ (1) NZ268513A (sv)
PT (2) PT1369409E (sv)
WO (1) WO1995000482A1 (sv)

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