FI114792B - Förfarande för framställning av terapeutiskt aktiva N-fenylalkyl-substituerade alfa-aminokarboxamid-derivat - Google Patents

Förfarande för framställning av terapeutiskt aktiva N-fenylalkyl-substituerade alfa-aminokarboxamid-derivat Download PDF

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Publication number
FI114792B
FI114792B FI910354A FI910354A FI114792B FI 114792 B FI114792 B FI 114792B FI 910354 A FI910354 A FI 910354A FI 910354 A FI910354 A FI 910354A FI 114792 B FI114792 B FI 114792B
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formula
oxybenzyl
amino
compound
aminopropionamide
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FI910354A
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English (en)
Finnish (fi)
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FI910354A0 (fi
Inventor
Philippe Dostert
Romeo Roncucci
Mario Varasi
Paolo Pevarello
Alberto Bonsignori
Franco Heidempergher
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Newron Pharm Spa
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Priority claimed from GB898912071A external-priority patent/GB8912071D0/en
Priority claimed from GB909007567A external-priority patent/GB9007567D0/en
Application filed by Newron Pharm Spa filed Critical Newron Pharm Spa
Publication of FI910354A0 publication Critical patent/FI910354A0/fi
Application granted granted Critical
Publication of FI114792B publication Critical patent/FI114792B/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • 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
    • A61P25/08—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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/63—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/02—Monothiocarboxylic acids
    • C07C327/04—Monothiocarboxylic acids having carbon atoms of thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C327/06—Monothiocarboxylic acids having carbon atoms of thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/58—One oxygen atom, e.g. butenolide
    • 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
    • C07D333/26—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 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms

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

Claims (2)

1. Förfarande för framställning av en terapeutiskt aktiv N-fenylalkyl-substituerad oi-aminokarboxamid med formeln 5 (Ia) ?·?" ,, . i^Y'CH2-N-?-C0^Rl2 (la> Rt—Z-f- Γ R'io 10 eller dess farmaceutiskt godtagbara sait, i vilken formel R7 är furyl, tienyl eller pyridyl eller fenyl, som är osubstituerad’eller substituerad med halogen, Ci-C4-alkyl, is Ci-C4-alkoxi eller CF3, Z är - (CH2) - eller -(CH2)v-Y-f väri v är ett heltal 1-4, och Y är -0-, -S- eller -NH-, R9 är väte eller en Ci-C4-alkyl, Ri0 är väte eller en Ci-C4-alky-1, som är osubstituerad eller substituerad med hydroxi eller fenyl, R'i0 är väte eller Rio och R'i0 bildar till-20 sammans med en intill belägen kolatom en C3-C6-cykloalkyl-ring, och Rn och Ri2 betecknar oberoende av varandra väte eller en Ci-C4-alkyl, och väri j* a) när Z är en grupp -(CH2)V-Y-, väri symbolerna v och Y ; | betecknar detsamma som ovan, och Rio samtidigt är väte el- 25 ler en Ci-C4-alkyl, R'i0 är väte och symbolerna R7 och R9 -— betecknar detsamma som ovan, ätminstone en av resterna Ru och Ri2 är nägot annat än väte, och väri b) när Z är -CH2- *·. och R9 och R'io samtidigt betecknar väte och resterna R7, * · Ru och Ri2 betecknar detsamma som ovan, är Ri0 nägot annat . 30 än väte eller en osubstituerad Ci-C4-alkyl, eller en ';;j terapeutiskt aktiv N-fenylalkyl-substituerad a- ·;·* aminokarboxamid med formeln (Ib) ' · ?H3 ,H aCH2—NH—GH—CON^ ( !b ) H ... eller dess farmaceutiskt godtagbara sait, i vilken fornjel 36 1U7*2 R'7 är en fenylring, som är osubstituerad eller substi-tuerad med en halogenatom, Z' är -(CH2) - eller en grupp -(CH2)V-Y-, väri v är ett heltal 1-4 och Y är -0-, -S-eller -NH-, kännetecknat därav, att 5 (i) för framställning av en förening med formeln (Ia) a) en förening med formeln (Ha) 1C R7_ZO^ ° (m) väri resterna R7 och Z betecknar detsamma som ovan, om-sättes med en förening med formeln (IVa) 15 ^10 R„ mi-c-ct»' (iva) R· 'R’2 n 10 20 väri resterna R9/ Rio» R'io, Rn och Ri2 betecknar detsamma som ovan och Rn och Ri2 inte bäda betecknar en Ci-C4-alkylgrupp, i närvaro av ett reduktionsmedel varvid man erhäller en förening med formeln (Ia) , väri Rn och Ri2 ; · inte bäda betecknar en Ci-C4-alkyl grupp, eller * : 25 b) en förening med formeln (Va) R9 ·. N~C—COOH . (Va) r7—z-j- R‘10 · 30 *;' eller dess alkylester, väri symbolerna R7/ Z, R9, Rio och R'10 betecknar detsamma som ovan, omsättes med en amin med ;··· formeln (Via) 35 ^R11 HNC^ (Via) 1 Rl2 37 114 792 väri resterna Rn och R12 betecknar detsamma som ovan, eller c) en förening med formeln (Vila) 5 ^9 /\.CH2—NH RT-Z-fjf (Vlla^ io väri symbolerna R7, Z, och R9 betecknar detsamma som ovan, omsättes med en förening med formeln (Villa) is w— ch2—CON^ (Villa) R-12 väri W betecknar en halogenatom och resterna Rn och Ri2 betecknar detsamma som ovan, varvid man erhäller en före-20 ning med formeln (Ia), väri R10 och R'i0 bäda betecknar väte, eller d) en förening med formeln (IXa) 1 * » · • · H Rio ; 25 II ^1-, IN-C—<CONv (IXa) r,-z^T r’.= r’2 . 30 väri symbolerna R7, Z, Rio, R'io, Rii och Ri2 betecknar * * » * "il detsamma som ovan, omsättes med en förening med formeln » » '·;·* (Xa) eller (Xla) * * * » * * t ·:··: R"9-W (Xa) R" 'g-CHO (Xla) 35 i fall av föreningen med formeln (Xla) i närvaro av ett v reduktionsmedel, i vilka formler W är en halogenatom, R"9 är en Ci-C4-alkyl och R"'9 betecknar väte eller en 33 1 1 4792 Ci-C3-alkyl, varvid man erhäller en förening med formeln (Ia), väri R9 är en Cx-C.t-alkyl, och (ii) för framställning av en förening med formeln (Ib) a) en förening med formeln (Hb) 5 10 väri resterna R'7 och Z' betecknar detsamma som ovan, omsättes med en förening med formeln (IVb) ch3 h 15 nh2—OH—CON^ (IVb) H i närvaro av ett reduktionsmedel, eller b) en förening med formeln (Vb) 20 H CH3 :. Il : N-CH-COOH . ( Vb ) K , k » ~11 “· * » » * *·. eller dess alkylester, väri symbolerna R'7 och Z' beteck nar detsamma som ovan, omsättes med en förening med for-30 meln (VIb) *: HN^ (VIb) ',35 i och om sä önskas, omvandlas föreningen med formeln (Ia) eller (Ib) tili nägon annan förening med formeln (Ia) eller respektive (Ib) och/eller om sä önskas, omvandlag 39 1 1 47 92 föreningen med formeln (Ia) eller (Ib) tili ett farmaceutiskt godtagbart sait och/eller, om sä önskas, omvandlas ett salt tili en fri förening och/eller, om sä önskas, skiljes en isomerblandning av föreningar med s formeln (Ia) eller (Ib) i enskilda isomerer.
2. Förfarande enligt patentkrav 1, kännetecknat därav, att man framställer en N-fenylalkyl-substituerad a-aminokarboxamid, som är ίο 2-[4-(3-klorbensyl)oxibensyl]aminopropionamid, 2-(4-bensyloxibensyl)amino-3-hydroxi-N-metylpropionamid, 2- [4-(3-klorbensyl)oxibensyl]amino-3-hydroxi-N-metylpro-pionamid, 2-[4-(2-klorbensyl)oxibensyl]amino-3-hydroxi-N-metylpro-15 pionamid, 2-(4-bensyloxibensyl)aminopropionamid, 2-[4-(2-fluorbensyl)oxibensyl]amino-3-hydroxi-N-metylpro-pionamid, 2-[4-(3-fluorbensyl)oxibensyl]amino-3-hydroxi-N-metylpro-20 pionamid, 2-[4-(2-klorbensyl)oxibensyl]aminopropionamid, 2-(4-bensylbensyl)aminopropionamid, ,2- [4- (3-f luorbensyl) oxibensyl] aminopropionamid, •, j j 2-(4-bensylaminobensyl)aminopropionamid, : 1 : 25 2 -[N-(4-bensylbensyl)-N-metyl]aminopropionamid, — 2 -[4 -(3-fenylpropyl)oxibensyl]aminopropionamid, 2- [4- (2-pyridyl)metyloxibensyl] aminopropionamid, 2-[4-(2-tenyl)oxibensyl]aminopropionamid, 2-[4-(2-furfuryl)oxibensyl]aminopropionamid, 30 2-[4-(3-tenyl)oxibensyl]aminopropionamid, 2- [4-(3-furfuryl)oxibensyl]aminopropionamid, 2-(4-bensyltiobensyl) aminopropionamid, ; 1-[(4-bensyloxibensyl)amino]cyklopropan-l-karboxamid, ,·; 1- [ (4-bensyloxibensyl) amino] cyklopentan-l-karboxamid, 35 1-[(4-bensyloxibensyl)amino]cyklopropan-1-N-metylkarbox- amid, ·'* 1- [ (4-bensyloxibensyl) amino] cyklopentan-l-N-metylkar- boxamid, / 40 1 1 4792 [4-(3-klorbensyl)oxibensyl]amino-N,N-dimetylacetamid, 2- [4- (3-trif luormetylbensyl) oxibensyl] amino-3-hydroxi-lime tylpropionamid, 2-[4-(3-metoxibensyl)oxibensyl]amino-3-hydroxi-N-metyl-5 propionamid, 2-[4-(2-trifluormetylbensyl)oxibensyl]amino-3-hydroxi-N-metylpropionamid, 2-[4-(2-metylbensyl)oxibensyl]amino-3-hydroxi-N-metylpro-pionamid, eller 10 2-[4-(3-metylbensyl)oxibensyl]amino-3-hydroxi-N-metylpro- pionamid, bereonde pä omständigheterna antingen som enskilda (S)-eller (R)-isomerer eller som en racemisk blandning av dessa, is eller ett farmaceutiskt godtagbart salt av dessa. * : I « I i t I » I • < I ’ > k ft· · • · ♦ « t · • · » I I . * » · • t ' I ' • k ' t · ’ ► i
FI910354A 1989-05-25 1991-01-23 Förfarande för framställning av terapeutiskt aktiva N-fenylalkyl-substituerade alfa-aminokarboxamid-derivat FI114792B (sv)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB898912071A GB8912071D0 (en) 1989-05-25 1989-05-25 N-phenylalkyl substituted-alpha-amino carboxamide derivatives and process for their preparation
GB8912071 1989-05-25
GB909007567A GB9007567D0 (en) 1990-04-04 1990-04-04 New n-substituted alpha-amino carboxamide derivatives and process for their preparation
GB9007567 1990-04-04
EP9000841 1990-05-25
PCT/EP1990/000841 WO1990014334A1 (en) 1989-05-25 1990-05-25 N-PHENYLALKYL SUBSTITUTED α-AMINO CARBOXAMIDE DERIVATIVES AND PROCESS FOR THEIR PREPARATION

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FI910354A0 FI910354A0 (fi) 1991-01-23
FI114792B true FI114792B (sv) 2004-12-31

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US (3) US5236957A (sv)
EP (2) EP0400495B1 (sv)
JP (1) JP2771328B2 (sv)
KR (1) KR0179661B1 (sv)
CN (1) CN1027588C (sv)
AT (1) ATE96775T1 (sv)
AU (1) AU645752B2 (sv)
CA (1) CA2033190C (sv)
CZ (1) CZ281420B6 (sv)
DE (1) DE69004337T2 (sv)
DK (1) DK0400495T3 (sv)
ES (1) ES2062174T3 (sv)
FI (1) FI114792B (sv)
HU (2) HUT55348A (sv)
IE (1) IE63934B1 (sv)
IL (1) IL94466A (sv)
MY (1) MY105618A (sv)
NO (1) NO179944C (sv)
NZ (1) NZ233785A (sv)
PT (1) PT94160B (sv)
RU (1) RU2097371C1 (sv)
WO (1) WO1990014334A1 (sv)
YU (1) YU48322B (sv)

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JPH04500215A (ja) 1992-01-16
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