PL129642B1 - Process for preparing novel derivatives of 1-/4-arylcyclohexyl/piperidine - Google Patents

Process for preparing novel derivatives of 1-/4-arylcyclohexyl/piperidine

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Publication number
PL129642B1
PL129642B1 PL1981236046A PL23604681A PL129642B1 PL 129642 B1 PL129642 B1 PL 129642B1 PL 1981236046 A PL1981236046 A PL 1981236046A PL 23604681 A PL23604681 A PL 23604681A PL 129642 B1 PL129642 B1 PL 129642B1
Authority
PL
Poland
Prior art keywords
radical
group
formula
aryl
atom
Prior art date
Application number
PL1981236046A
Other languages
Polish (pl)
Other versions
PL236046A1 (en
Original Assignee
Janssen Pharmaceutica Nv
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US06/222,091 external-priority patent/US4329353A/en
Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv
Publication of PL236046A1 publication Critical patent/PL236046A1/xx
Publication of PL129642B1 publication Critical patent/PL129642B1/en

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  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (1)

1. Zastrzezenie patentowe Sposób wytwarzania nowych pochodnych i-/4-arylocyklohekeylo/piperydyny o wzorze 1 1 1, w którym Ar oznacza rodnik arylowy lub benzodioksolilowy-1,3, R oznacza atom wo¬ doru, grupe cyjanows, grupe karboksylowe, nizsze grupe alkoksykarbonylowe, nizsze gru¬ pe aryloalkoksykerbonylowe, grupe karbemylowe, nizsze grupe jedno- lub dwualkiloamlno- karbonylowa, nizsze grupe jedno- lub /aryloelkilo/aminokarbonylowa,, nizsze grupe /ary- loelkilo/elkiloaminokarbonylowe, grupe hydroksylowej nizsze grupe alkoksylowe, nizsze grupe alkilokerbonyloksy, grupe forraylowe, nizsze grupe elkilokarbonylowe., grupe ary- lokarbonylowe, nizsze grupe eryloalkllokarbonylowe, nizszy rodnik alkilowy, nizszy ro¬ dnik alkenylowy, nizszy rodnik alkinylowy lub rodnik cykloheksylowy, zas A oznacza dwu- wartosclowy rodnik o wzorze 2, w którym Ar oznacza rodnik arylowy, a R oznacza nizszy rodnik alkilowy, nizszy rodnik aryloalkilowy, nizszy rodnik cyjanoalkllowy, ni¬ zszy rodnik aminoalkilowy, nizszy rodnik jedno- lub dwualklloamlnoalkllowy, nizszy ro¬ dnik jedno- lub dwu/aryloelkilo/aminoalkilowy, nizszy rodnik f/aryloalkilo/alkiloaminoj alkilowy, nizszy rodnik hydroksyalkilowy, nizszy rodnik merkaptoelkilowy, nizszy rod¬ nik aloksyalkilowy, nizszy rodnik alkllotioelkilowy, nizszy rodnik aryloalkilowy, ni¬ zszy rodnik arylotioalkllowy, nizszy rodnik aryloalkoksyalkilowy, nizszy rodnik arylo- alkilotioalkilowy lub rodnik o wzorze -C H2 -Q -C/-X/-Y R f w którym n oznacza liczbe calkowite od 1 do 6, Q oznacza atom tlenu, atom siarki lub grupe o wzorze HR , w któ¬ rym R oznacza atom wodoru, nizszy rodnik alkilowy, rodnik arylowy lub nizszy rodnik aryloalkilowy, p oznacza 0 lub 1, X oznacza atom tlenu lub atom siarki, R oznacza atom wodoru, nizszy rodnik alkilowy, rodnik arylowy lub nizszy rodnik aryloalkilowy, m oznacza 0 lub 1, a Y oznacza atom tlenu, atom siarki lub grupe o wzorze NR , w któ¬ rym R ma wyzej podane znaczenia, przy czym jezeli Y oznacza atom tlenu, a m i p sa równe 1, wówczas R ma znaczenie inne niz etom wodoru, a jesli p jest równe 1, wówczas n ma wartosc rózne od zera, z tym ze rodnik arylowy oznacza rodnik tienylowy, pirydy- nylowy, naftalenylowy, ewentualnie podstawiony rodnik fenylowy z 1-3 podstawnikami, takimi jak atom chlorowca, nizszy rodnik alkilowy, nizsza grupa alkoksylowa, grupa fe- nylonizsza alkiloksylowa, rodnik trójfluorometylowy, grupa nitrowa, grupa aminowa lub grupa hydroksylowa, ich stereoizomerów, oraz ich soli addycyjnych z kwasami, dopusz¬ czalnych w lecznictwie, znamienny tym, ze zwiezek o wzorze 4, w którym 11 2 R , Ar i Ar maje wyzej podane znaczenie, poddaje sie reakcji ze zwiezkiem o wzorze 4-a-l 4-a-i R -W, w którym R ma wyzej podane znaczenie; a W oznacza odpowiednio reaktywne grupe odszczepialne, take jak atom chlorowca lub grupa sulfonyloksylowa, taka jak grupa metylosulfonyloksylowa lub 4-metylofenylosulfonyloksylowa, w obojetnym rozpu¬ szczalniku organicznym, w obecnosci zasady w podwyzszonej temperaturze*129 G42 R' Ar1 NA Wzór 1 tf Ar1 Wzór 4 4^ Ar* h'zórz Ar2 -I- R^W 4-a-l Wzór 3 Schemat NC N-R! h/zórSxL^i QH±. / % N F hzot 6 wzór 7 Pracownia Poligraficzna UP PRL. Naklad 100 egz. Cena 100 zl PL PLClaim 1. A method for the preparation of the new i- (4-arylcyclohekeyl) piperidine derivatives of the formula 11, in which Ar is an aryl or 1,3-benzodioxolyl radical, R represents a hydrogen atom, a cyano group, a carboxyl group, the lower group alkoxycarbonyl, lower arylalkoxycerbonyl, carbemyl, lower mono- or dialkylamino-carbonyl, lower mono- or (arylelkyl) aminocarbonyl, lower (arylelkyl) elkyl, lower alkybonyl, nshebonyl, nshebonyl group a forrayl group, a lower elkylcarbonyl group, an arylcarbonyl group, a lower arylalkylcarbonyl group, a lower alkyl radical, a lower alkenyl radical, a lower alkynyl radical or a cyclohexyl radical, where A is a di-radical of the formula 2 aryl, and R is lower alkyl, lower arylalkyl, lower cyanoalkyl, lower aminoalkyl, n and mono- or dialkylaminoalkyl lower radical, mono- or di (arylelkyl) aminoalkyl lower radical, f (aralkyl) alkylaminoalkyl lower radical, hydroxyalkyl lower, mercaptoelkyl lower, alkylthisalkyl lower alkyl, alkylthisalkyl lower radical , lower arylthioalkyl radical, lower arylalkoxyalkyl radical, lower arylalkylthioalkyl radical or a radical of the formula -C H2 -Q -C / -X / -YR f where n is an integer from 1 to 6, Q is an oxygen atom, sulfur or a group of the formula HR, in which R is a hydrogen atom, a lower alkyl radical, an aryl radical or a lower arylalkyl radical, p is 0 or 1, X is an oxygen atom or a sulfur atom, R is a hydrogen atom, a lower alkyl radical, an aryl radical or the lower arylalkyl radical, m is 0 or 1 and Y is an oxygen atom, a sulfur atom or a group of the formula NR, in which R is as defined above, ne 1, then R is not hydrogen, and if p is equal to 1, then n is not zero, except that aryl is thienyl, pyridinyl, naphthalenyl, optionally substituted phenyl from 1-3 substituents such as halogen atom, lower alkyl radical, lower alkoxy group, phenylethyloxy group, trifluoromethyl radical, nitro group, amino group or hydroxyl group, their stereoisomers, and their acid addition salts which are acceptable in therapy, in that a compound of formula 4, wherein R 2, R 2, Ar, and Ar is as defined above, is reacted with a compound of formula 4-a1 4-a and R -W, wherein R is as defined above; and W is suitably a reactive leaving group, such as a halogen atom or a sulfonyloxy group such as a methylsulfonyloxy or 4-methylphenylsulfonyloxy group, in an inert organic solvent in the presence of a base at elevated temperature. 4 4 ^ Ar * h'zórz Ar2 -I- R ^ W 4-al Formula 3 Scheme NC NR! h / zórSxL ^ and QH ±. /% N F hzot 6 pattern 7 Printing workshop of the Polish People's Republic. Mintage 100 copies Price PLN 100 PL PL
PL1981236046A 1981-01-09 1981-03-10 Process for preparing novel derivatives of 1-/4-arylcyclohexyl/piperidine PL129642B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/222,091 US4329353A (en) 1980-10-22 1981-01-09 1-(4-Aryl-cyclohexyl)piperidine derivatives, method of use thereof and pharmaceutical compositions thereof

Publications (2)

Publication Number Publication Date
PL236046A1 PL236046A1 (en) 1982-12-06
PL129642B1 true PL129642B1 (en) 1984-05-31

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Application Number Title Priority Date Filing Date
PL1981236046A PL129642B1 (en) 1981-01-09 1981-03-10 Process for preparing novel derivatives of 1-/4-arylcyclohexyl/piperidine

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PL236046A1 (en) 1982-12-06

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