FI113645B - Förfarande för framställning av en terapeutiskt användbar 1-(4-hydroxifenyl)-1-hydroxi-2-(substituerad amino)alkanförening och en mellanprodukt som används i förfarandet - Google Patents

Förfarande för framställning av en terapeutiskt användbar 1-(4-hydroxifenyl)-1-hydroxi-2-(substituerad amino)alkanförening och en mellanprodukt som används i förfarandet Download PDF

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FI113645B
FI113645B FI915403A FI915403A FI113645B FI 113645 B FI113645 B FI 113645B FI 915403 A FI915403 A FI 915403A FI 915403 A FI915403 A FI 915403A FI 113645 B FI113645 B FI 113645B
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hydroxy
mmol
product
hydroxyphenyl
ethyl acetate
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FI915403A
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FI915403A0 (fi
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Bertrand L Chenard
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Pfizer
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C07D211/36—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 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
    • 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
    • C07D211/36—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 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
    • 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
    • C07D211/36—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 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
    • C07D211/54—Sulfur 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
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  • General Health & Medical Sciences (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)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Claims (5)

1. Förfarande för framställning av en terapeutiskt anvandbar 1-(4-hydroxifenyl)-l-hydroxi-2-(substituerad 5 amino)alkanförening med formeln fH där R är H, Ci-6-alkyl, C2-6_alkenyl eller C2-6~alkynyl; och
10 E är Cl· cA ‘ där Y3 är -<CH2>m-jj^j , : 15 X1 är väte, Ci-3-alkyl, halogen, OR1, OCOR1, CO2R1, ·': SR1, NHR1, NHCOR1, C0NH2 eller CN; R1 är väte eller Ci-3-alkyl; och m är 0, 1, 2, 3 eller 4; eller h. för framställning av dess farmaceutiskt godtagbara syra- 20 additionssalt, kännetecknat av att man utför en hyd-* ridreduktion av en förening med formeln f jc*0 47 11364E varvid R2 är en konventionell skyddsgrupp av hydroxi el-ler merkaptan; R betecknar detsamma som ovan;
5 E är 0« OH eller } där Y3 är -<CHg>m-(l·^) 10 där X1' är väte, Ci-3-alkyl, halogen, OR1, OR2, OCOR1, COOR1, SR1, SR2, NHR1, NR1R3, NHCOR1, CONH2 eller CN; där R1 är väte eller Ci_3-alkyl, R2 är sasom ovan definie-rats och R3 är en konventionell aminoskyddsgrupp; m är 0, 1, 2, 3 eller 4; och 15 skyddsgruppen/-grupperna avlägsnas pä ett konven- .* tionellt sätt.
> · ,,· 2. Förfarande enligt patentkrav 1, känneteck- :* nat av att R är metyl med IS*, 2S*-relativ stereokemi; OH i 'V CH3 2 0
3. Förfarande enligt patentkrav 1, känneteck- ! n at av att man framställer ( + ) -(IS,2S)-1-(4-hydroxife- nyl) -2- (4-hydroxi-4-fenylpiperidin) -1-propanol.
4. Förfarande enligt patentkrav 1, känneteck-n a t av att man framställer (-) - (1R, 2R)-1-(4-hydroxife-25 nyl)-2-(4-hydroxi-4-fenylpiperidin)-1-propanol. * · 113645 48
5. Förening med formeln . jCrV° ..... R2 O där R är H, Ci-6-alkyl, C2-6-alkenyl eller C2-6-alkynyl; 5 och E är OH OH y3 eller > där Y3 är -<0Ηε>Λ-jf^j 10 X1" är väte, Ci-3-alkyl, halogen, OR1, OR2 , OCOR1, COOR1, SR1, SR2', NHR1, NR1R3' , NHCOR1, CONH2 eller CN; ί .·’ R1 är väte eller C1-3-alkyl; (· m är 0, 1, 2, 3 eller 4; :1 15 R2' är tri (C1-4) alkylsilyl eller bensyl; och ; R3' är bensyloxikarbonyl. » · ! » ·
FI915403A 1989-05-17 1991-11-15 Förfarande för framställning av en terapeutiskt användbar 1-(4-hydroxifenyl)-1-hydroxi-2-(substituerad amino)alkanförening och en mellanprodukt som används i förfarandet FI113645B (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US8902176 1989-05-17
PCT/US1989/002176 WO1990014087A1 (en) 1989-05-17 1989-05-17 2-piperidino-1-alkanol derivatives as antiischemic agents
PCT/US1990/000292 WO1990014088A1 (en) 1989-05-17 1990-01-16 2-piperidino-1-alkanol derivatives as antiischemic agents
US9000292 1990-01-16

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FI915403A0 FI915403A0 (fi) 1991-11-15
FI113645B true FI113645B (sv) 2004-05-31

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JP (1) JPH0735368B2 (sv)
KR (1) KR920004138B1 (sv)
CN (1) CN1032209C (sv)
AT (1) ATE150021T1 (sv)
BR (1) BR1101053A (sv)
CZ (1) CZ284342B6 (sv)
DE (1) DE69030134T2 (sv)
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FI (1) FI113645B (sv)
HK (1) HK1000468A1 (sv)
IL (2) IL94357A (sv)
NO (1) NO180268C (sv)
PH (1) PH31464A (sv)
PL (1) PL163580B1 (sv)
RU (1) RU2029769C1 (sv)
SK (1) SK279476B6 (sv)
WO (2) WO1990014087A1 (sv)
ZA (1) ZA903741B (sv)

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US5594007A (en) * 1991-04-18 1997-01-14 Pfizer Inc. Method for treating spinal cord trauma with phenolic 2-piperidino-1-alkanols
US5710168A (en) * 1991-10-23 1998-01-20 Pfizer Inc. 2-piperidino-1-alkanol derivatives as neuroprotective agents
US6255322B1 (en) * 1992-06-19 2001-07-03 Pfizer Inc. 2-(4-hydroxypiperidino)-1-alkanol derivatives as antiischemic agents
US5436255A (en) * 1992-07-23 1995-07-25 Pfizer Inc. Method of treating diseases susceptable to treatment by blocking NMDA-receptors
US5498610A (en) * 1992-11-06 1996-03-12 Pfizer Inc. Neuroprotective indolone and related derivatives
AU684568B2 (en) * 1994-01-31 1997-12-18 Pfizer Inc. Neuroprotective chroman compounds
NZ284852A (en) * 1994-08-18 1998-06-26 Pfizer 3-(piperidin-1-yl)-chroman-4,7-diol and 1-(4-hydrophenyl)-2-(piperidin-1-yl) alkanol derivatives; medicaments; used as a neuroprotective agent
US5731317A (en) * 1995-03-10 1998-03-24 Merck & Co., Inc. Bridged piperidines promote release of growth hormone
ES2170857T3 (es) * 1995-08-11 2002-08-16 Pfizer Metanosulfonato de (1s,2s)-1-(4-hidroxifenil)-2-(4-hidroxi-4-fenilpiperidin-1-il)-1-propanol trihidrato.
TW450807B (en) * 1995-09-15 2001-08-21 Pfizer Pharmaceutical compositions for treating tinnitus comprising neuroprotective agents
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EP1409477B1 (en) 2001-07-24 2008-09-17 Richter Gedeon NYRT Piperidine derivatives as nmda receptor antagonists
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ES2347152T3 (es) * 2003-11-26 2010-10-26 Pfizer Products Inc. Derivados de aminopirazol como inhibidores de gsk-3.
JP2008526923A (ja) * 2005-01-13 2008-07-24 ノイロサーチ アクティーゼルスカブ 新規８−置換８−アザ−ビシクロ［３．２．１］オクタン誘導体及びモノアミン神経伝達物質再取り込み阻害剤としてのそれらの使用
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WO1990014087A1 (en) 1990-11-29
CZ284342B6 (cs) 1998-10-14
CN1032209C (zh) 1996-07-03
IL94357A (en) 1996-08-04
NO914485L (no) 1991-11-15
DE69030134D1 (de) 1997-04-17
SK232890A3 (en) 1998-11-04
RU2029769C1 (ru) 1995-02-27
DK0398578T3 (da) 1997-10-13
BR1101053A (pt) 2000-03-28
US5338754A (en) 1994-08-16
IL114174A0 (en) 1995-10-31
JPH035478A (ja) 1991-01-11
WO1990014088A1 (en) 1990-11-29
NO180268C (no) 1997-03-19
ZA903741B (en) 1991-12-24
NO180268B (no) 1996-12-09
DE69030134T2 (de) 1997-06-19
JPH0735368B2 (ja) 1995-04-19
KR920004138B1 (ko) 1992-05-25
PH31464A (en) 1998-11-03
KR900018085A (ko) 1990-12-20
PL285190A1 (en) 1991-03-25
FI915403A0 (fi) 1991-11-15
US5185343A (en) 1993-02-09
IL114174A (en) 1996-06-18
NO914485D0 (no) 1991-11-15
SK279476B6 (sk) 1998-11-04
PL163580B1 (pl) 1994-04-29
HK1000468A1 (en) 1998-03-27
CN1047291A (zh) 1990-11-28
CZ232890A3 (cs) 1998-07-15
US5391742A (en) 1995-02-21
ATE150021T1 (de) 1997-03-15

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