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PT97510A - Processo de preparacao de novos derivados da 2-metoxifenilpiperazina - Google Patents

Processo de preparacao de novos derivados da 2-metoxifenilpiperazina Download PDF

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Publication number
PT97510A
PT97510A PT97510A PT9751091A PT97510A PT 97510 A PT97510 A PT 97510A PT 97510 A PT97510 A PT 97510A PT 9751091 A PT9751091 A PT 9751091A PT 97510 A PT97510 A PT 97510A
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Prior art keywords
methoxyphenyl
piperazin
butyl
piperazine
ethyl
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PT97510A
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English (en)
Inventor
Aurelio Orjales-Venero
Luisa Alonso-Cires
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Espanola Prod Quim Farm
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Publication of PT97510A publication Critical patent/PT97510A/pt

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
    • 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
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D213/82—Amides; Imides in position 3
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    • 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
    • C07D295/12—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 or doubly bound nitrogen atoms
    • C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • 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
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • 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
    • C07D333/28—Halogen atoms
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    • 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

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Description

s to
PATENTE DE INVENÇÃO DE "PROCESSO DE PREPARAÇAO DE NOVOS DERIVADOS DA 2-METOXIFENILPIPERAZINA"
REQUERENTE FABRICA ESPANOLA DE PRODUCTOS QUlMICOS Y FARMACÊUTICOS, S.A. (FAES)
INVENTORES
AURÉLIO ORJALES-VENERO LUISA ALONSO-CIRÉS •k-Jeifkitieitirkirkifkifkifkifk-kifkitick-k-k-k-k-kirkie^krk-k-kirk-kicicicitirk-k-kickiciçifirkirkifkisifkickifkieiíirkirkirk-k-k-k-kidck 0 presente invento refere-se a uma série de novos derivados da 2-metoxifenilpiperazina, de formula I e seus sais de adição com ácidos farma-ciuticamente aceitáveis.
Na formula I, A i um grupo -C0-, um grupo -(CH2)nHNC0-, com valores de n compreendidos entre dois e quatro ou um grupo -(CH2)nHNCH2-, com valores de n compreendidos entre dois e quatro, e B e um grupo arilo, heteroarilo, aril-alquilo, heteroarilalquilo ou cicloalquílo, que pode estar substituído ou não por um halogéneo, de preferência cloro, e/ou por um grupo metoxi, metilo ou ami-no. Entre os ácidos farmacêuticamente aceitáveis para a preparação de sais de adição, encontram-se os ácidos clorídrico, fumãrico, oxãlico e semelhantes. 0 processo de preparação a que se refere esta patente consiste na reacção de uma amina de formula. = 2 =η.
(II) em que X pode ser hidrogénio ou um grupo alquilenamino, no qual a cadeia car-bonada contem dois, tres ou quatro átomos de carbono, com um cloreto de ben-zoTlo substituído numa ou várias posições por um halogéneo, um grupo amino ou um grupo metoxi; ou com o cloreto de um acido heteroaromatico, no qual o hete- roátomo pode ser um oxigénio, um enxofre ou um nitrogénio, que faz parte de um ciclo de cinco ou seis anéis de cadeia e que pode estar substituído por um ou mais grupos meti lo, um halogéneo que pode ser cloro, ou um anel aromático; ou com o cloreto de um ácido ciclo - ou bicicloalcanoico ou - alquenoico. A reac- ção faz-se na presença de um dissolvente orgânico apropriado como diclorometano, tetraidrofurano ou éter, a temperatura ambiente, em meio básico por adição de trietilamina, pi ridina, bicarbonato de sodio ou outras bases orgânicas ou inorgânicas.
Os compostos em que A é um grupo alquilaminometileno obtem-se por redução dos correspondentes derivados alquilaminocarbonilo, com um agente redutor apropriado, como o hidreto de li tio e aluminio, sódio e borohidreto sõdi-co.
Num estudo inicial determinou-se a afinidade dos compostos descritos no presente invento com os receptores 5-HT^, mediante a técnica descrita inicialmente por Gozkan e col. (Nature, 305, 140-2. 1983) de união e deslocação de radioligando realizada em tecido obtido de córtex frontal de rata e empregando [3H]-8-0H-DPAT como ligando. Os compostos estudados mostram um grau de afinidade com os ditos receptores semelhante ao da molécula de buspirona.
Os seguintes exemplos dão mais detalhes sobre o invento, sem que este fique limitado de modo algum aos mesmos.
Exemplo 1
Preparação de N-[2-[4-(2-metoxifeni 1)pi perazina-l-i1]eti1]adamantancarboxamida.

Claims (1)

  1. = 3 Η Dissolvem-se l.Og de l-(2-aminoetil)-4-(2-metoxifenil)piperazina em 20 ml de tetraidrofurano, adicionando-se 2.1 ml de trietilamina. Sobre a dissolução deita-se em gotas a 09C, l.Og de cloreto de adamantancarbonilo, dissolvidos em 20 ml de tetraidrofurano. Finalizada a adição, deixa-se agitando a temperatura ambiente, durante uma hora, ao fim da qual se juntam 40 ml de agua e se extrai com 20 ml de diclorometano, tres vezes. Separa-se a camada orgânica e seca-se com sulfato de sodio amidro. Depois de destilar o dissolvente no vácuo, obtem-se 1.6g de um solido branco, que se purifica por cromatografia de coluna, empregando diclorometano/metanol (9/1) como eluente P.F.: 112-4QC. Exemplo 2 Preparação de N-[4-[4-(2-metoxifenil)piperazina-l-il]butil]-2-pirrolcarboxamida Dissolve-se lg de l-(4-aminobutil)-4-(2-metoxifenil)piperazina em 20 ml de diclorometano, adicionando 1.5g de pi ridina. Deitam-se em gotas a 0QC, l.Og de cloreto de pirrolcarbonilo, dissolvidos em 20 ml de diclorometano. Mantem-se a agitação uma hora, a 20QC, ao fim da qual se juntam 40 ml de agua e se extrai, juntando 20 ml de diclorometano uma vez mais. A camada orgânica seca-se com sulfato de sodio anidro e o dissolvente elimina-se por destilação no vácuo. Obtêm-se 1.4g de um sólido que se purifica por cromatografia de coluna, utilizando diclorometano/metanol (9/1) como eluente. P. F.: 173-4QC. R EIVINDICAÇPES ia. Processo de preparação de compostos de formula geral
    em que A e um grupo -C0-. um grupo -(CH2)nHNC0- com valores de n compreendidos entre dois e quatro, ou um grupo -(CHr^nHNCl·^-, com valores de n compreendidos entre dois e quatro, e B e um grupo arilo, heteroarilo, arflalquilo, heteroari-lalquilo, cicloalquilo ou bicicloalquilo, substituídos ou não por um halogeneo de preferencia, cloro, e/ou por um grupo metoxi, meti lo e amino, e dos seus = 4 =
    sais de adição com ácidosfarmaceuticamente aceitáveis, que se caracteriza por se fazer reagir uma piperazina N-substituida com um cloreto de acido, num dissolvente apropriado, como diclorometano, tetrahidroforfurano ou eter, em presença de uma base como trietilamina, pi ridina ou bicarbonato sõdico, durante uma hora, a temperatura ambiente. 2ã. Processo de acordo com a reivindicação anterior caracteriza-do por a piperazina N-substituida ter por formula
    em que X pode ser hidrogénio ou um grupo -(C^^Nl·^, com valores de n compreendidos entre dois e quatro. 3ã. Processo de acordo com as reivindicações anteriores carac-terizado por o cloreto de acido ser um cloreto de um ácido benzõico substituído numa ou várias posições por um halogeneo, de preferencia cloro, um grupo ami-no ou um grupo metoxi, ou de um ácido heteroaromãtico, em que o heteroãtomo possa ser oxigénio, enxofre ou nitrogénio, fazendo parte de ciclos com cinco ou seis aneis de cadeia, substituídas ou não por um ou mais grupos metilo, halÕge-no ou fenilo, ou de um ácido alcanoico ou alquenoico, substituído por um ciclo heteroaromático ou um grupo fenilo, ou de um ácido ciclo- ou biciclocarboxilico. 4§. Processo de acordo com as reivindicações anteriores caracte-rizado por os compostos,emqie A na formula geral I e um grupo -(Cl^^HNCl·^-, se obterem por redução, com um agente redutor apropriado, como 0 hidreto de li tio e alumínio, dos compostos nas quais A na formula geral I é um grupo -(Ch^^HNCO-. 5§. Processo com as reivindicações anteriores caracterizado por os novos derivados de 2-metoxifenilpiperazina serem: . N-[2-[4-(2-metoxifenilpiperazin-l-il]etil]-4-amino 5-cloro-2-metoxibenzamida . l-(2-metoxifenil)-4-(2-tiofencarbonil)piperazina. . N-[2-[4-(2-metoxifeni1)piperazin-l-i 1 ]eti 1 ]-3-tiofencarboxamida. . N-[2-[4-(2-metoxifeni 1)piperazin-l-il]etil]fenilacetamida. . N-[2-[4-(2-metoxifenil)piperazin-l-il]etil]-2,4-diclorobenzamida. s. = 5 = t
    n- l-(2-metoxi feni1)-4-(3-ti ofencarboni1)pi perazi na 1-(5-meti1-2-ti ofencarboni1)-4-(2-metoxi feni1)pi perazi na. N-[2-[4-(2-metoxi feni1)pi perazi n-l-i1]eti1]-5-meti1“2-tiofencarboxamida. 1-(3-cloro-2-ti ofencarboni1)-4-(2-metoxi feni1)pi perazi na. 1-(3-meti1-2-ti ofencarboni1)-4-(2-metoxi feni1)pi perazi na. 1-benzoi1-4-(2-metoxi feni1)pi perazi na. 1-(2,4-dicl orobenzoi 1)-4-(2-metoxi feni1)pi perazi na. N-[2-[4-(2-metoxifeni1)pi perazi n-l-i1]eti1]-3-meti1-2-ti ofencarboxami da. N-[2-[4-(2-metoxifeni1)piperazin-l-il]etil]-2-pirro1carboxamida. N-[2-[4-(2-metoxifeni1)piperazin-l-i1]eti1]-3-indolcarboxamida. N-[2-[4-(2-metoxi feni1)pi perazi n-l-i 1 ]eti 1 ]-3-ti ofenacetami da. N-[3-[4-(2-metoxi feni 1)pi perazi n-l-i 1Ipropri1]-3-indolcarboxami da. N-[4-[4-(2-metoxifeni1)piperazin-l-il]butil]-3-piridincarboxamida. N-[3-[4-(2-metoxi feni1)pi perazi n-l-i1]propi1]-2-pi rrolcarboxami da. N-[4-[4-(2-metoxifeni1)piperazin-l-i 1]butil]-2-pirrol carboxamida. N-[3-[4-(2-metoxi feni1)pi perazi n-l-i1]propri 1 ]-3-pi ri dincarboxami da. l-(3-indo1carbonil)-4-(2-metoxifenil)piperazina. N-[4-[4-(2-metoxifeni1)piperazin-l-il]buti1]-3-indolcarboxamida. N-[4-[4-(2-metoxifeni1)piperazin-l-il]butil]-2,4-diclorobenzamida. 1-(3-i ndolmeti1)-4-(2-metoxifenil)piperazina. N-[4-[4-(2-metoxi feni1)pi perazi n-l-i1]buti1]-2-ti ofencarboxami da. N-[4-[4-(2-metoxi fenil)pi perazi n-l-i 1 ]buti 1 ]-3-meti 1 -2-ti ofencarboxami da. N-[4-[4-(2-metoxi feni 1)pi perazi n-l-i 1 ]buti 1 ]-3-c1oro-2-ti ofencarboxami da. N-[4-[4-(2-metoxifenil)piperazin-l-il]butil]-3-metoxi-2-tiofencarboxamida. N-[4-[4-(2-metoxi feni1)pi perazi n-l-i1]buti1 ]fenilacetamida. N-[4-[4-(2-metoxifeni1)piperazi n-l-i1]buti l]-2-furancarboxami da. N-[4_[4_(2-metoxi fenil)pi perazi n-l-i 1 ]buti "Π-3-tiofenacetami da. N-[4-[4-(2-metoxi feni1)pi perazi n-l-i 1 ]buti 1 ]-5-meti1-2-tiofencarboxami da. N-[4-[4-(2-metoxi feni1)pi perazi n-l-i1]buti1]-3-tiofencarboxami da. N-[2-[4-(2-metoxifeni1)piperazin-l-i1]eti1]-5-benzimidazolcarboxamida. 1-(2-metoxi feni1)-4-[2-(2-pi rrolmeti 1ami no)eti1]piperazi na. 1-(2-metoxi feni1)4-[2-(3-meti1-2-ti ofenmeti1ami no)eti1]pi perazi na. N-[2-[4-(2-metoxi feni1)pi perazi n-l-i1]eti1]-l-meti1-2-pirrocarboxamida. N-[2-[4-(2-metoxi feni1)pi perazi n-l-i 1 ]eti 1 ]-ci sbi ci cl o (3,3,0) octan-2-carboxami da N-[4-[4-(2-metoxifenil) pi perazi n-l-il]butil]-2-i ndol carboxamida. N-[4-[4-(2-metoxi feni1)pi perazi n-l-i1]buti1]-2-norbornancarboxami da. N-[4-[4-(2-metoxi feni1)pi perazi n-l-i1]buti l}-5-norbornen-2-carboxami da.
PT97510A 1991-01-24 1991-04-29 Processo de preparacao de novos derivados da 2-metoxifenilpiperazina PT97510A (pt)

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