LV11817B - Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties - Google Patents

Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties Download PDF

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LV11817B
LV11817B LVP-97-40A LV970040A LV11817B LV 11817 B LV11817 B LV 11817B LV 970040 A LV970040 A LV 970040A LV 11817 B LV11817 B LV 11817B
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phenyl
propylamine
amino
acetamide
methylethyl
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LVP-97-40A
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LV11817A (lv
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James J Napier
Ronald C Griffith
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Astra Ab
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    • 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
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    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
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    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
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    • C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/52—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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    • 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
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    • 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
    • C07C237/08—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 atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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    • 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
    • C07C237/10—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 atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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Claims (10)

  1. LV 11817 IZGUDROJUMA FORMULA Savienojuma ar formulu I A r A r i c H 2 ' R, .N, •R I, kurā Ar, un Ar2 neatkarīgi apzīmē fenilgrupu, kas aizvietota ar vienu vai vairākām aminogrupām, nitrogrupām, hlora atomiem, broma atomiem, hidroksigrupām, C,.6alkoksigrupām, C,.6alkilgrupām vai ciāngrupām; pie tam viens no Ar, vai Ar2 var apzīmēt fenilgrupu; R, apzīmē ūdeņradi vai C,.6alkilgrupu; R2 apzīmē ūdeņradi vai COCH2NH2; R3 apzīmē ūdeņradi vai C,.6alkilgrupu; pie tam, ja Ra apzīmē ūdeņradi, tad Ar, un Ar2 abi var apzīmēt fenilgrupu, Ar, un Ar2 viens vai abi var apzīmēt fluorfenilgrupu vai 2-, 3- vai 4-pi-ridinilgrupu un R, var apzīmēt C,.6alkoksikarbonilgrupu vai trifluor-metilgrupu; ar nosacījumu, ka: (a) ja R, un R2 katrs apzīmē H un Ar, un Ar2 katrs apzīmē fenilgrupu, tad R3 ir citāds kā C,.6alkilgrupa; (b) ja Ar2 apzīmē 2-, 3- vai 4-piridinilgrupu, tad R, apzīmē C,.6alkilgrupu; un (c) ja R, un R2 katrs apzīmē H, tad Ar, neapzīmē fenilgrupu, kas aizvietota ar aminogrupu; vai tā farmaceitiski saderīga sāļa izmantošana par aktīvo sastāvdaļu neiroprotektīvu vai pretkrampju medikamentu ražošanā. Izmantošana saskaņā ar 1. punktu, kur savienojums ar formulu I ir: 1.2- difeniletilamīns; 1.2- difenil-2-propilamīns; 2 1.2- bis(4-fluorfenil)-2-propiiamīns; 1.2- difenil-2-butilamīns; (-)-1,2-difenil-2-propilamīns; (+)-1,2-difenil-2-propilamīns; 2.3- difenil-2-aminopropānskābes metilesteris; N-metil-1,2-difenil-2-propilamins; 1-(3-nitrofenil)-2-fenil-2-propilamīns; 1-(3-hlorfenil)-2-fenil-2-propilamīns; 1-(3-bromfenil)-2-fenil-2-propilamins; 1- (3-ciānfenil)-2-fenil-2-propilamins; 2- (2-metilfenil)-1-fenil-2-propilamīns; 1-(4-hlorfenil)-2-fenil-2-propilamins; 1 -fenil -2-(3,4-dihlorfenil)-2-propilamīns; 1 -fenil -2-(3-metoksifenil)-2-propilamīns; 1-(4-hidroksifenil)-2-fenil-2-propilamīns; 1-(4-hidroksifenil)-2-feniletilamins; 1-fenil-2-(4-hidroksifenil)etilamins; 1.2- bis(4-hidroksifenil)etilamīns; 1-fenil-2-(4-hidroksifenil)-2-propilamīns; 1.2- bis(4-hidroksifenil)-2-propilamīns; 1-fenil-2-(2-piridinil)etilamīns; 1 -fenil-2-(3-piridinil)etilamīns; 1 -fenil-2-(4-piridinil)etilamīns; 3.3.3- trifluor-1,2-difenil-2-propilamīns; N-metil-3I3,3-trifluor-1,2-difenil-2-propilamins; vai tā farmaceitiski saderīgs sālis. 1-Fenil-2-(2-piridinil)etilamīns vai tā farmaceitiski saderīgs sālis izmantošanai par farmaceitisku preparātu. Farmaceitiska kompozīcija, kas satur 1-fenil-2-(2-piridinil)etilamīnu vai tā farmaceitiski saderīgu sāli maisījumā ar farmaceitiski saderīgu palīglīdzekli, atšķaidītāju vai nesēju. 3 LV 11817
  2. 5. Savienojums ar formulu IA A r 2 a A r j a- C H 2 R , a
    I λ kurā A^a un Ar2a neatkarīgi apzīmē fenilgrupu, kas aizvietota ar vienu vai vairākām aminogrupām, nitrogrupām, hlora atomiem, broma atomiem, hidroksigrupām, C^alkoksigrupām, C^alkilgrupām vai ciāngrupām; pie tam viens no A^a vai Ar2a var apzīmēt fenilgrupu; R^ apzīmē ūdeņradi vai C^alkilgrupu; R2a apzīmē ūdeņradi vai COCH2NH2; R3a apzīmē ūdeņradi vai C^alkilgrupu; ar nosacījumu, ka, ja R2a apzīmē ūdeņradi, tad R,a apzīmē C^alkilgrupu; vai tā farmaceitiski saderīgs sālīs.
  3. 6. Savienojums saskaņā ar 5. punktu, kurā Ar,a un Ar2a viens vai abi apzīmē 4-hidroksifenilgrupu.
  4. 7. Savienojums saskaņā ar 5. punktu, kurā Ar,a un Ar2a ir mono- vai diaizvietoti.
  5. 8. Savienojums saskaņā ar 5. punktu, kurā Rļa apzīmē metilgrupu.
  6. 9. Savienojums saskaņā ar 5. punktu, kurā R3a apzīmē ūdeņradi.
  7. 10. Savienojums saskaņā ar 5. punktu, kurš ir 1-(4-hidroksifenil)-2-fenil-2-propilamīns; 1-fenil-2-(4-hidroksifenil)-2-propilamīns; 1,2-bis(4-hidroksifenil)-2-propilamīns; 1-(3-nitrofenil)-2-fenil-2-propilamīns; 1-(3-hlorfenil)-2-fenil-2-propilamīns; 4 1-(3-bromfenil)-2-fenil-2-propilamīns; 1- (3-ciānfenil)-2-fenil-2-propilamīns; 2- (2-metilfenil)-1-fenil-2-propilamīns; 1-(4-hlorfenil)-2-fenil-2-propilamīns; 1-fenil-2-(3,4-dihlorfenil)-2-propilamīns; 1- fenil-2-(3-metoksifenil)-2-propilamīns; 2- (3-hlorfenil)-1 -fenil-2-propilamīns; 1 -(2-hlorfenil)-2-fenil-2-propilamīns; 2-(2-hlorfenil)-1-fenil-2-propilamīns; 2-(3-nitrofenil)-1 -fenil-2-propilamīns; 2-(4-hlorfenil)-1-fenil-2-propilamīns; 2-(3,4-dimetoksifenil)-1-fenil-2-propilamīns; 2-(4-metilfenil)-1-fenii-2-propilamīns; 2-(4-metoksifenil)-1-fenil-2-propilamīns; 1-(3,4-dihlorfenil)-2-fenil-2-propilamīns; 1- (4-metoksifenil)-2-fenil-2-propilamīns; 2- amino-N-[1 -(3-hlorfenil)-2-fenil-1 -metiletil]acetamīds; 2-amino-N-[2-(2-hlorfenil)-1 -fenil-1 -metiletiljacetamīds; 2-amino-N-[2-(4-hlorfenil)-1 -fenil-1 -metiletil]acetamids; 2-amino-N-[1 -(2-metilfenil)-2-fenil-1 -metiietil]acetamīds; 2-amino-N-[1-(2-hlorfenil)-2-fenil-1-metiletiljacetamīds; 2-amino-N-[2-(3-hlorfenil)-1 -fenil-1 -metiletil]acetamīds; 2-amino-N-[2-(3-aminofenil)-1 -fenil-1 -metiletiljacetamīds; 2-amino-N-[2-(3-bromfenil)-1 -fenil-1 -metiletiljacetamīds; 2-amino-N-[2-(3-nitrofeni!)-1 -fenil-1 -metiletiljacetamīds; 2-amino-N-[1 -(3-nitrofenil)-2-fenil-1 -metiletiljacetamīds; 2-amino-N-[1 -(3-aminofenil)-2-fenil-1 -metiletiljacetamīds; 2-amino-N-[1 -(4-hlorfenil)-2-fenil-1 -metiletiljacetamīds; 2-amino-N-[1-(3,4-dihlorfenil)-2-fenil-1-metiletiljacetamīds; 2-amino-N-[1-(3,4-dimetoksifenil)-2-fenil-1-metiletiljacetamīds; 2-amino-N-[2-(3-ciānfenil)-1 -fenil-1 -metiletiljacetamīds; 2-amino-N-[1 -(4-metilfenil)-2-fenil-1 -metiletiljacetamīds; 2-amino-N-[1 -(4-hidroksifenil)-2-fenil-1 -metiletiljacetamīds; 2-amino-N-[1-(4-hidroksifenil)-2-feniletil]acetamīds; 2-amino-N-[2-(4-hidroksifenil)-1 -fenil-1 -metiletiljacetamīds; 5 LV 11817 2-amino-N-[2-(4-hidroksifenil)-1-feniletil]acetamīds; 2-amino-N-[1,2-bis(4-hidroksifenil)-1 -metiletil]acetamīds; 2-amino-N-[1,2-bis(4-hidroksifenil)etil]acetamids; 2-amino-N-[1 -(3-metoksifenil)-2-fenil-1 -metiletiljacetamīds; 2-amino-N-[1 -(4-metoksifenil)-2-fenil-1 -metiletil]acetamīds; 2-amino-N-[2-(3,4-dihlorfenil)-1 -fenil-1 -metiletil]acetamīds; 2-amino-N-[2-(4-metoksifenil)-1 -fenil-1 -metiletil]acetamīds; vai tā farmaceitiski saderīgs sālis.
  8. 11. Savienojums ar formulu IA saskaņā ar 5. punktu vai tā farmaceitiski sadengs sālis izmantošanai par farmaceitisku preparātu.
  9. 12. Farmaceitiska kompozīcija, kas satur savienojumu ar formulu IA saskaņā ar 5. punktu vai tā farmaceitiski saderīgu sāli maisījumā ar farmaceitiski saderīgu palīglīdzekli, atšķaidītāju vai nesēju.
  10. 13. Metode savienojuma ar formulu IA saskaņā ar 5. punktu vai tā farmaceitiski saderīga sāļa iegūšanai, kas ietver: a) iegūstot savienojumus, kuros R2a apzīmē ūdeņradi un R3a apzīmē C^alkilgrupu, atbilstoša savienojuma ar formulu IA, kurā R3a apzīmē ūdeņradi, alkilēšanu; b) iegūstot savienojumus, kuros R2a un R3a abi apzīmē ūdeņradi, atbilstoša savienojuma ar formulu IIA Ά r 2 a NH A r j a-C H 2- IIA, CHO kurā A^a, Ar2a un R,a ir kā noteikts 5. punktā, amīdgrupas hidrolīzi; c) iegūstot savienojumus, kuros R2a un R3a abi apzīmē ūdeņradi, savienojuma ar formulu IIIA 6 R j a A r , a- CH2- NH -A r 2 a I I I A, c(o)or< kurā A^a, Ar2a un F^a ir, kā noteikts 5. punktā un R4 apzīmē alkilgrupu vai arilgrupu, reducējošu karbamāta sašķelšanu; d) iegūstot savienojumus, kuros R2a apzīmē COCH2NH2, aminoaizsarggrupas atšķelšanu savienojumam ar formulu IVA A r CK2 R a A r 2 a N R 3 a IVA, C(0)ch2np{?2 kurā P1 un P2 kopā veido piemērotu aizsarggrupu un A^a, Ar2a, R,a un R3a ir, kā noteikts 5. punktā; vai e) iegūstot savienojumus, kuros R2a apzīmē COCH2NH2, savienojuma ar formulu VA R j a •A r 2 a A r ļ a- C H 2" VA, NR3 a C(0)CH2C l kurā Ar,a, Ar2a, R,a un R3a ir, ka noteikts 5. punkta, aminēšanu.
LVP-97-40A 1988-08-12 1997-03-13 Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties LV11817B (en)

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AU654802B2 (en) 1994-11-24
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