FI94752B - Förfarande för framställning av terapeutiskt användbara propenonoximetrar - Google Patents

Förfarande för framställning av terapeutiskt användbara propenonoximetrar Download PDF

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FI94752B
FI94752B FI895757A FI895757A FI94752B FI 94752 B FI94752 B FI 94752B FI 895757 A FI895757 A FI 895757A FI 895757 A FI895757 A FI 895757A FI 94752 B FI94752 B FI 94752B
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group
formula
carbon atoms
trans
mixture
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FI895757A
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English (en)
Finnish (fi)
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FI94752C (sv
FI895757A0 (sv
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Bernard Labeeuw
Patrick Gueule
Christian Congy
Murielle Rinaldi
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Sanofi Sa
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/58—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Diabetes (AREA)
  • Psychiatry (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Hydrogenated Pyridines (AREA)

Claims (8)

1. Förfarande för framställning av terapeutiskt användbara propenonoximetrar, vilkas struktur i etylendub-5 belbindningen är trans och vilka har formeln: H Ar' -C-C-C-Ar Il I N M ^ (I) 10 0 - (CH2)n - R2 väri Ar och Ar* oberäende av varandra är: 15 a) en fenylgrupp, vilken är osubstituerad eller vilken är mono- eller polysubstituerad med nägon av föl-jande: en halogenatom, (lägre alkyl)-grupp (1-4 kolato-mer), nitrogrupp, hydroxylgrupp, alkoxigrupp (1-4 kol-atomer), acyloxigrupp (1-4 kolatomer), dimetylamino-20 grupp, karboxialkoxigrupp, väri alkylen innehäller 1-4 kolatomer; eller en naftyl- eller 9-antrylgrupp, eller b) en heteroaromatisk grupp som väljs ur pyri-dyl-, tienyl- och furylgrupperna; Rx och R2 oberäende av varandra är en vä tea torn eller • 25 en (lägre alkyl)-grupp (1-4 kolatomer) eller Rx och R2 « tillsammans med den kväveatomen vid vilken de är bundna bildar en 1-pyrrolidinyl-, piperidino-, morfolino- eller 1-piperazinylgruppering; M är en väteatom, klor- eller bromatom eller rak- 30 kedjad eller förgrenad (lägre alkyl)-grupp med 1-6 kol- *. atomer; n är 2 eller 3; samt för framställning av salter av nämnda före-ningar med mineralsyror eller organiska syror, k ä n n e-35 tecknat därav, att 55 94752 a) ett kalkon med formeln: H Ar' - ^ - C « C - Ar (II)
2. Förfarande enligt patentkrav 1, k ä n n e -t e c k n a t därav, att man framställer en förening med formeln: 25 f /=<?* V H xch3 30 väri Ar’ är pyridyl, tienyl, furyl eller naftyl, är hydroxyl eller metoxi och W2 är väte, eller ett sait därav. li 57 94752
3. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer en förening med formeln: 5 /=r\_ ” '-' N H CH3 V(CH2)2-nCT ch3 10 väri Ar är pyrldyl eller 9-antryl, eller ett salt därav.
4. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer en förening med 15 formeln: v.x=r u \=^w2 20 /R1 (CH2)n-NC r2 vari R1 och R2 oberäende av varandra är en väteatom eller ; 25 en (lägre alkyl)-grupp (1-3 kolatomer) eller R2 och R2 tlllsammans med den kväveatomen vld vllken de är bundna bildar en 1-pyrrolldinyl-, morfolino- eller 1-piperazinyl-gruppering; M är en väteatom, klor- eller bromatom eller rak- 30 kedjad eller förgrenad (lägre alkyl)-grupp med 2 eller 3 *. kolatomer; * n är 2 eller 3; wx är H, OH, 0CH3, N(CH3)2, 0C0CH3 eller OCOC2H5; W2 är H eller 0CH3; 94752 W': är H, halogen, CH3, N02, OH eller OCH3; och W'2 är H eller F; eller ett salt därav.
5. Förfarande enligt patentkrav 1, k ä n n e - 5 tecknat därav, att man framställer ett surt oxalat av trans-[1-(N,N-dimetylaminoetoxiimino)-1,3-di(3-tie-nyl)]-2-propen.
5 X’ - (CH2)n - (V) R2 väri och R2 är som ovan definierats och X' är en avlägsnande grupp, eller - när z är en grupp med formeln 10 -(CH2)n-X, väri X är som ovan definierats, - med ett amin med formeln: ^R1 HN ^ 15 \r2 väri Rj och R2 är som ovan definierats, varefter c) valfritt den i steg a) eller b) sä erhällna fö-reningen överförs tili nägot sait därav med en mineralsyra 20 eller organisk syra.
5. M väri Ar och Ar' är som ovan definierats, behandlas med ett hydroxylamin med formeln:
10 H2NOZ (III) väri Z är: en aminoalkylkedja med formeln:
15 Rl -(σ!2)η - Νχ R2 väri R2 och R2 är som ovan definierats; 20 en väteatom; eller en substituerad alkylgrupp med formeln: -<α.2>ηχ 25 väri n är som ovan definierats och X är en avlägs- ψ nande grupp; varefter b) den sd erhälinä föreningen med formeln: H
30 Ar' -C-C-C-Ar (Ia) Il I NM O - Z väri Ar och Ar' är som ovan definierats och Z är 35 väte eller en grupp -(CH2)n-X, behandlas - när Z är väte - 56 94752 i närvaro av ett basiskt kondensationsmedel med ett amin med formeln: Z*1
6. Förfarande enligt patentkrav 4, känne-tecknat därav, att man framställer syn-{trans-[Ι- ΙΟ (N, N-dimetylaminoetoxiimino)-1-(2-fluorfenyl)-3-(4-hyd- roxifenyl)]}-2-propen eller dess hemifumarat.
7. Förfarande enligt patentkrav 4, känne-tecknat därav, att man framställer ett oxalat av syn-{trans-[1-(N,N-dimetylaminoetoxiimino)-1-(2-metoxife- 15 nyl)-3-(4-hydroxifenyl)]}-2-propen.
8. Förfarande enligt patentkrav 4, känne-tecknat därav, att man framställer syn-{trans-[1-(N, N-dimetylaminoetoxiimino )-1-( 2-klorf enyl) -3- (4-hydroxi-fenyl)]}-2-propen eller dess oxalat. 8 1
FI895757A 1988-12-02 1989-12-01 Förfarande för framställning av terapeutiskt användbara propenonoximetrar FI94752C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8815860 1988-12-02
FR8815860A FR2639942B1 (fr) 1988-12-02 1988-12-02 Ethers oximes de propenone, procede pour leur preparation et compositions pharmaceutiques les contenant

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FI895757A0 FI895757A0 (sv) 1989-12-01
FI94752B true FI94752B (sv) 1995-07-14
FI94752C FI94752C (sv) 1995-10-25

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US (2) US5166416A (sv)
EP (1) EP0373998B1 (sv)
JP (1) JP2562503B2 (sv)
KR (1) KR0156910B1 (sv)
AR (1) AR245704A1 (sv)
AU (2) AU623706B2 (sv)
CA (1) CA2004350C (sv)
CZ (1) CZ419091A3 (sv)
DE (1) DE68908374T2 (sv)
DK (1) DK174434B1 (sv)
ES (1) ES2059804T3 (sv)
FI (1) FI94752C (sv)
FR (1) FR2639942B1 (sv)
HK (1) HK1001557A1 (sv)
HU (1) HU211463A9 (sv)
IE (1) IE63400B1 (sv)
IL (1) IL92519A (sv)
NO (1) NO171269C (sv)
NZ (2) NZ240166A (sv)
PT (1) PT92446B (sv)
ZA (1) ZA899201B (sv)

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EP2266554A1 (en) 2009-05-26 2010-12-29 Sanofi-Aventis Method of treating sleep disorders using eplivanserin
EP2365805A1 (en) * 2008-11-13 2011-09-21 Sanofi Method of treating sleep disorders using eplivanserin
EP2186511A1 (en) 2008-11-13 2010-05-19 Sanofi-Aventis Method of treating sleep disorders using eplivanserin
FR2938534B1 (fr) 2008-11-14 2012-10-26 Sanofi Aventis Procede de preparation de l'hemifumarate d'eplivanserine
KR20110102496A (ko) * 2009-02-10 2011-09-16 닛뽕소다 가부시키가이샤 함질소 화합물 및 유해 생물 방제제
EP2255807A1 (en) 2009-05-26 2010-12-01 Sanofi-Aventis Method of treating sleep disorders using the combination of eplivanserin and zolpidem
EP2255726A1 (en) 2009-05-26 2010-12-01 Sanofi-Aventis Spectral profile of SWS enhancing drugs
EP2269600A1 (en) 2009-07-02 2011-01-05 Sanofi-Aventis Treatment of sleep disorders using eplivanserin in COPD patients
CN101941919B (zh) * 2009-07-07 2014-07-02 天津药物研究院 一种制备顺式肟及肟醚衍生物的方法
CN106883141B (zh) * 2017-03-15 2018-08-10 何黎琴 一种丹皮酚肟醚类化合物、其制备方法及医药用途

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FR2639942B1 (fr) * 1988-12-02 1991-03-29 Sanofi Sa Ethers oximes de propenone, procede pour leur preparation et compositions pharmaceutiques les contenant

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AU623706B2 (en) 1992-05-21
AR245704A1 (es) 1994-02-28
US5166416A (en) 1992-11-24
NO171269C (no) 1993-02-17
FR2639942A1 (fr) 1990-06-08
NZ231606A (en) 1992-02-25
HK1001557A1 (en) 1998-06-26
DE68908374D1 (de) 1993-09-16
ES2059804T3 (es) 1994-11-16
CZ419091A3 (en) 1993-05-12
NZ240166A (en) 1992-02-25
CA2004350A1 (en) 1990-06-02
CA2004350C (en) 1997-06-03
US5290951A (en) 1994-03-01
JP2562503B2 (ja) 1996-12-11
DE68908374T2 (de) 1994-01-05
EP0373998B1 (fr) 1993-08-11
HU211463A9 (en) 1995-11-28
NO171269B (no) 1992-11-09
AU1218392A (en) 1992-05-28
EP0373998A1 (fr) 1990-06-20
NO894786L (no) 1990-06-05
AU640310B2 (en) 1993-08-19
IL92519A (en) 1994-05-30
DK605989D0 (da) 1989-11-30
DK174434B1 (da) 2003-03-03
FR2639942B1 (fr) 1991-03-29
FI94752C (sv) 1995-10-25
ZA899201B (en) 1990-09-26
NO894786D0 (no) 1989-11-30
IE893848L (en) 1990-06-02
PT92446B (pt) 1995-07-18
JPH02262552A (ja) 1990-10-25
DK605989A (da) 1990-06-03
IE63400B1 (en) 1995-04-19
FI895757A0 (sv) 1989-12-01
AU4568889A (en) 1990-06-07
PT92446A (pt) 1990-06-29
KR900009572A (ko) 1990-07-04
KR0156910B1 (ko) 1998-12-01

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