PL102474B1 - A method of producing new derivatives of n-/4-piperidinylo/-amines - Google Patents

A method of producing new derivatives of n-/4-piperidinylo/-amines Download PDF

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PL102474B1
PL102474B1 PL1976187910A PL18791076A PL102474B1 PL 102474 B1 PL102474 B1 PL 102474B1 PL 1976187910 A PL1976187910 A PL 1976187910A PL 18791076 A PL18791076 A PL 18791076A PL 102474 B1 PL102474 B1 PL 102474B1
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aryl
ethyl
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PL1976187910A
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    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
    • 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
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Claims (4)

1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych N- -(4-piperydynylo)amin o ogólnym wzorze 1, w któ¬ rym Z oznacza atom wodoru, atom chlorowca, niz¬ szy rodnik alkilowy, nizsza grupe alkoksylowa lub rodnik trójfluorometylowy, a L oznacza rod¬ nik 2-aryloetylowy, 2-arylo-l-metyloetylowy, Ma¬ rylokarbonylo)etyIowy, 3-arylopropylowy, 2-(arylo- amdno)etylowy, 2-arylo-2-(nizszy alkilokarbomy1o- ksy)etylowy, lub 2-arylo-2-(nizszy alkilokarbonylo- ksy)-l^metyloetylowy, przy czym grupa aryIowa w tych rodnikach oznacza grupe (trójfluoromety- lo)fenylowa, nitrofenylowa, aminofenylowa, nafta¬ lenyIowa, pirydynylowa, furanylowa-2 lub 1-me- tylo-lH-pirolilowa-2, a gdy L oznacza rodnik 2-ary- lo-2-(nizszy alkilokarbonyloksy)etylowy, lub 2nary- lo-2-(nizszy alkilokarbomyloksy)-l-metyloetylowy, grupa arylowa oznacza takze grupe fenyIowa, chlo- jrowcofenyiowa, nizsza grupe alkilofenylówa, niz¬ sza grupe alkoksyfenyIowa lub grupe tienylowa-2, X oznacza atom wodoru lub rodnik metylowy, R oznacza nizszy rodnik alkilowy, rodnik cykloalki- lowy o 3—6 atomach wegla lub nizsza grupe alko¬ ksylowa, przy czym w tym ostatnim przypadku L oprócz podamych poprzednio znaczen moze równiez oznaczac rodnik alkilowy o 3—10 atomach wegla, rodnik cykloalkilometylowy o 3—6 ato¬ mach wegla w czesci cykloalkilowej, rodnik 2-ary¬ loetylowy, 2-arylo-l-metyloetylowy, l-(arylokarbo- nylo)etylowy, 3-arylopropylowy, 2-(aryloaminoety¬ lowy, 4-fenylocykloheksylowy, 2,3-dwuwodoro-lH- -indenylowy-2 lub nizszy rodnik alkenylowy, w których grupa arylowa oznacza grupe fenyIowa, chlorowcofenylowa, nizsza grupe alkilofenylówa, nizsza grupe , alkoksyfenylowa lub grupe tienylo- wa-2, a R1 oznacza grupe estru kwasu karboksy- lówego o wzorze COOR2, w którym R2 oznacza n}zszy' rodnik akilowy lub nizszy rodnik alkenylo¬ wy, grupe alkanoilowa o ogólnym wzorze -C(0)R3, w którym R3 oznacza nizszy rodnik alkilowy, lub 10 15 20 30 35 40 45 50 55 60 R4 oznacza atom wodoru lub nizszy rodnik alkilo¬ wy, oraz ich farmaceutycznie dopuszczalnych soli addycyjnych z kwasami lub stereoizomerów opty¬ cznych, znamienny tym, ze zwiazek o ogólnym wzo¬ rze 2, w którym R1, R, X i Z maja poprzednio podane znaczenie, poddaje sie reakcji ze zwiaz¬ kiem o ogólnym wzorze LY, w którym L ma po¬ przednio podane znaczenie a Y oznacza reaktyw¬ na reszte estrowa, korzystnie atom chlorowca, gru¬ pe metanosulfonylowa lub 4-metylobenzenosulfony- lowa, przy czym reakcje prowadzi sie w obojet¬ nym rozpuszczalniku organicznym, korzystnie w o- becnosci obojetnej zasady.
2. Sposób wytwarzania nowych pochodnych N- -(4-piperydynylo)amin o ogólnym wzorze 1, w któ¬ rym Z oznacza atom wodoru, atom chlorowca, niz¬ szy rodnik alkilowy, nizsza grupe alkoksylowa lub rodnik trójfluorometylowy, L oznacza rodnik al¬ kilowy o 3—10 atomach wegla, rodnik cykloalkilo¬ metylowy o 3—€ atomach wegla w czesci alkilo¬ wej, 2-aryloetylowy, 2-arylo-l-metyloetylowy, l-(a- rylokarbonylo)etylowy, 3-arylopropylowy, 2-(arylo- amino)etylowy, 4-fenylocykloheksylowy, 2,3-dwu- wodoru-lH-indenylowy-2 lub nizszy rodnik alke¬ nylowy, przy czym grupa arylowa w tych rodni¬ kach oznacza grupe fenylowa, chlorowcofenylowa, nizsza grupe alkilofenylowa, nizsza grupe alkoksy- fenylowa lub grupe tienylowa-2, X oznacza atom wodoru lub rodnik metylowy, R oznacza nizszy rodnik alkilowy lub rodnik cykloalkilowy o 3—6 atomach wegla, R1 oznacza grupe estru kwasu karboksylowego o wzorze -COOR2, w którym R2 oznacza nizszy rodnik alkilowy lub nizszy rodnik alkenylowy, grupe alkanoilowa o ogólnym wzorze -C(0)R3, w którym R3 oznacza nizszy rodnik alki¬ lowy, lub grupe o ogólnym wzorze -CH2-O-P4, w którym R4 oznacza atom wodoru lub nizszy rodnik alkilowy oraz ich farmaceutycznie dopuszczalnych soli addycyjnych z kwasami lub stereoizomerów op¬ tycznych, znamienny tym, ze zwiazek o ogólnym wzorze 2, w którym R1, R, X i Z maja poprzed¬ nio podane znaczenie, poddaje sie reakcji ze zwiaz¬ kiem o ogólnym wzorze LY, w którym L ma* po¬ przednio podane znaczenie a Y oznacza reaktywna reszte estrowa, korzystnie atom chlorowca, grupe metanosulfonylowa lub 4-metylobenzenosulfonylo- wa, przy czym reakcje prowadzi sie w obojetnym rozpuszczalniku organicznym, korzystnie w obec¬ nosci odpowiedniej zasady.
3. Sposób wedlug zastrz. 2, znamienny tym, ze N-[4-(metoksymetylo)-4-piperydynylo]-N-fenyloamid kwasu propionowego poddaje sie reakcji z meta- nosulfonianem 2-tiofenoetylu i otrzymuje sie N-4- -(metoksymetylo)-l-[2-(2-tienylo)etylo]-4-piperydy- nylo-N-fenyloamid kwasu propionowego, ewentual¬ nie w postaci farmaceutycznie dopuszczalnych soli addycyjnych z kwasami. 4. Sposób wedlug zastrz. 2, znamienny tym, ze ester metylowy kwasu 4-[N-(l-ketopropylo)fenylo- amino]piperydynokarboksylowego-4 poddaje sie re¬ akcji z (2-bromoetylo)benzenem i otrzymuje sie ester metylowy kwasu 4-[N-(l-ketopropylo)fenylo- amino]-l-(2-fenyloetylo)piperydynokarboksylowego- -4, ewentualnie w postaci farmaceutycznie dopusz- grupe ó ogólnym wzorze -CH2-Q-R4, w którym 6|5 czalnych soli addycyjnych z kwasami.41 102 474 5. Sposób wedlug zastrz. 2, znamienny tym, ze ester metylowy kwasu 4-[(l-ketopropylo)fenyloami- no]piperydynokarboksylowego-4 poddaje sie reakcji z metanosulfonianem 2-tiofenoetylu i otrzymuje sie ester metylowy kwasu 4-[(l-ketopropylo)fenyloami- no]-l^[2-(2-tienylo)etylo]piperydynokarboksylowego- -4, ewentualnie w postaci farmaceutycznie dopusz¬ czalnych soli addycyjnych z kwasami. iz 6. Sposób wedlug zastrz. 2, znamienny tym, ze ester metylowy kwasu 4-[(l-ketopropylo)fenyloami- no]piperydynokarboksylowego-4 poddaje sie reakcji z metanosulfonianem l-metylo-2-fenyloetylu i o- trzymuje sie ester metylowy kwasu l-(metylo-2- -fenyioetylo)-4-i[(l-ketopropylo(fenyloamino]pipery- dynokarboksylowego-4, ewentualnie w postaci far¬ maceutycznie dopuszczalnych soli addycyjnych z kwasami. L Y+HN 0 -_*L-KJ 'Wzót 1 Schemat i M-C-P Wzór i p-N Xm i a1^. P-N X " Schemat li02 474 H2 x , NH Fd/C (^ \ + fctór 5 0 ii /—( n™ r-CHe-0-C-hol fCH2-0-C-ff5 NH Wzór 6 Schemat 3 Wrór 8 P-lJp^CH2-0-CH8-O dcyloHanie
4. 7 Wzór 5 X „ /^CHrf-CH,-0' • n0 Hj^7 Wzór 40 H« X Pd/C HN CH20H -C-R WeJrW Schemat 4 "CH2-0< xNH2 2 Wrór 6; Schemat 5.102 474 bwóg* NaOH X Wc&r M NH Hzór 15 ^CH, HMPT\ Rl0H 'CHHrfim* NH Z Uzór 42 Schemat 5 (c.d.) o w* ' . jA*7 Yizori7 X jag^-o-LoS. — Wz»r 4S 0 R-0-C- ,0 ddcarbo- ..r .0 NH2 -^g HN X XNH2 NH NH MzÓr 20 ^ ih^ Schemat 6 Wzór 24 CH2-y + HrtC^ Yizcr 21 o<*db NH J^ Wzór U Z f)IH ^sor fó Schemat 7102 474 H^-4h /+Rt't THF Rr-0-c-O o x? -z Wzór 27 i5.-_/~Vru- ^ 9 aH/C-r Li^i ^Vch2-o-c-Onh 5 ^ x n ócbernoi;$ Q / V Q^ nizszy Ry-0-C-ffx!:"? H- R-Mg-hal Jtar27 \ ^_ 4q X0 X? 5 hfeór 29 L 4Z Wzdr 39 L J Z Wzór 22 \ w WNH ^Z Wsór3f 5c/?ennqt 9102 414 X Z Wzór12 | ^ y X suchy beae^ // Vru _i^f Y^H?UH MH Wzór33 ^ Schemat -/O z X (yCHf^Hj0H °-Qfaw NH "z Wrór33 X NH ^ ,J4 X Wrór 33 X 3 HHPT N=/ ' WNH N*H ¦ 0-CHr^CH2"0"* Schematu MH M'(nizszy ofef?) Z Wzór 33 X * *™L f\€H2-^MCuHr°"dkil NaOH ^ N-V)|H102 474 y P-N XS3 NH y P-N CCH,-0-R NH Wzór 23 mór 32 ¦CH2 (CH2-CH2 . 35 Wzór 36 ^CH2-CH2- Cl^CH2-CH2 \ttzÓY V Wzo/38 CH2-CH2- Wzók 39 P^CHrCH2- CH3/3-CH-Ch- CH3 Wzór 40 Wzór 41 " I^zók 42 ^NH-CHo-CH,- lAJzór 44 (CH2-CHS CF3 O-CH^-CHr 0CH3 Wzór 48 • Wzo/45 // ^ CHo-CH 2 ^ [2 OCH, Nzór<7 Wzór 49 -cooch/ xn Wzok 50 Wzór 51 Wzór 52 F-^yCH2-CH2- Wzok53 ^CH2-CHa-iÓ2 474 CH?-CHó mór 55 02N^_-CH2-CH2- mw 56 ^VCH2-CH2- Nzór 57 „ Q-C0-C2H5 ^CH-CHr mót 58 H2N^CHrCHr PL PL
PL1976187910A 1975-03-14 1976-03-12 A method of producing new derivatives of n-/4-piperidinylo/-amines PL102474B1 (pl)

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US55851175A 1975-03-14 1975-03-14
US05/648,685 US3998834A (en) 1975-03-14 1976-01-13 N-(4-piperidinyl)-n-phenylamides and -carbamates

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AT (1) AT359493B (pl)
AU (1) AU503632B2 (pl)
BG (1) BG28259A3 (pl)
CA (1) CA1080232A (pl)
CH (1) CH629486A5 (pl)
CZ (1) CZ278060B6 (pl)
DE (1) DE2610228A1 (pl)
DK (1) DK148960C (pl)
ES (1) ES446034A1 (pl)
FI (1) FI61481C (pl)
FR (1) FR2303546A1 (pl)
GB (1) GB1538938A (pl)
HU (1) HU172963B (pl)
IE (1) IE42512B1 (pl)
IL (1) IL49204A (pl)
IT (1) IT1057988B (pl)
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SE (1) SE426486B (pl)
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DE2610228A1 (de) 1976-09-30
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IE42512L (en) 1976-09-14
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IL49204A (en) 1979-11-30
AT359493B (de) 1980-11-10
IT1057988B (it) 1982-03-30
PH12746A (en) 1979-08-09
FI61481C (fi) 1982-08-10
DK148960B (da) 1985-12-02
NL185279C (nl) 1990-03-01
ES446034A1 (es) 1977-10-16
FI760646A (pl) 1976-09-15
NL7602612A (nl) 1976-09-16
CZ278060B6 (en) 1993-08-11
AU1200676A (en) 1977-09-22
YU65276A (en) 1982-08-31
JPS51115478A (en) 1976-10-12
US3998834A (en) 1976-12-21
FR2303546B1 (pl) 1980-11-28
SE7602740L (sv) 1976-09-15
PT64898B (en) 1977-08-18
DE2610228C2 (pl) 1990-04-05
LU74511A1 (pl) 1976-09-01
FR2303546A1 (fr) 1976-10-08
NL185279B (nl) 1989-10-02
JPS5946217B2 (ja) 1984-11-10
DK148960C (da) 1986-06-23
AU503632B2 (en) 1979-09-13
NO146162C (no) 1982-08-11
PT64898A (en) 1976-04-01
SU1227109A3 (ru) 1986-04-23
CZ163276A3 (en) 1993-03-17
DK110376A (da) 1976-09-15
ATA184676A (de) 1980-04-15
BG28259A3 (en) 1980-03-25
FI61481B (fi) 1982-04-30
YU39960B (en) 1985-06-30
SE426486B (sv) 1983-01-24
CA1080232A (en) 1980-06-24
NZ180096A (en) 1978-06-02
GB1538938A (en) 1979-01-24
HU172963B (hu) 1979-01-28
IE42512B1 (en) 1980-08-27
NO760591L (pl) 1976-09-15

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