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 PDFInfo
- Publication number
- 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
- Authority
- PL
- Poland
- Prior art keywords
- formula
- radical
- group
- aryl
- ethyl
- Prior art date
Links
Classifications
-
- 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
Landscapes
- 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
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
Publications (1)
Publication Number | Publication Date |
---|---|
PL102474B1 true PL102474B1 (pl) | 1979-03-31 |
Family
ID=27071767
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL1976187910A PL102474B1 (pl) | 1975-03-14 | 1976-03-12 | A method of producing new derivatives of n-/4-piperidinylo/-amines |
Country Status (28)
Country | Link |
---|---|
US (1) | US3998834A (pl) |
JP (1) | JPS5946217B2 (pl) |
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) |
LU (1) | LU74511A1 (pl) |
NL (1) | NL185279C (pl) |
NO (1) | NO146162C (pl) |
NZ (1) | NZ180096A (pl) |
PH (1) | PH12746A (pl) |
PL (1) | PL102474B1 (pl) |
PT (1) | PT64898B (pl) |
SE (1) | SE426486B (pl) |
SU (1) | SU1227109A3 (pl) |
YU (1) | YU39960B (pl) |
Families Citing this family (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4179569A (en) * | 1975-03-14 | 1979-12-18 | Janssen Pharmaceutica N.V. | N-(4-piperidinyl)-N-phenylamides |
US4225606A (en) * | 1975-09-23 | 1980-09-30 | Janssen Pharmaceutica N.V. | N-Aryl-N-(1-L-4-piperidinyl)arylacetamides |
US4208418A (en) * | 1975-09-23 | 1980-06-17 | Janssen Pharmaceutica N.V. | N-Aryl-N-(1-alkyl-4-piperidinyl)arylacetamides |
FR2389622B1 (pl) * | 1977-05-05 | 1982-05-21 | Janssen Pharmaceutica Nv | |
US4167574A (en) * | 1978-03-13 | 1979-09-11 | Janssen Pharmaceutica, N.V. | N-phenyl-N-(4-piperidinyl)amides |
US4584303A (en) * | 1984-04-09 | 1986-04-22 | The Boc Group, Inc. | N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds |
FR2608602A1 (fr) * | 1986-12-23 | 1988-06-24 | Cerm Cent Europ Rech Mauvernay | Nouvelles 3-piperidineamines ou 3-azepineamines substituees, leur preparation et leurs applications en therapeutique |
US4849521A (en) * | 1987-11-02 | 1989-07-18 | Boc, Inc. | Stereoselective preparation of 3-substituted-4-piperidine compounds and derivatives |
US4791121A (en) * | 1987-11-02 | 1988-12-13 | The Boc Group, Inc. | 4-phenyl-4-(N-(phenyl)amido) piperidine derivatives and pharmaceutical compositions and method employing such compounds |
USRE33495E (en) * | 1987-11-02 | 1990-12-18 | Boc, Inc. | Stereoselective preparation of 3-substituted-4-anilino-piperidine compounds and derivatives |
US4921864A (en) * | 1987-11-02 | 1990-05-01 | Boc, Inc. | 4-Phenyl-4-(N-(phenyl)amido) piperidine derivatives and pharmaceutical compositions and method employing such compounds |
US4957929A (en) * | 1987-11-02 | 1990-09-18 | Boc, Inc. | 4-phenyl-4-[N-(phenyl)amido]piperidine compounds and pharmaceutical compositions employing such compounds |
US5013742A (en) * | 1987-11-02 | 1991-05-07 | Boc, Inc. | 4-phenyl-4-N-(phenyl) amido piperidine derivatives and pharmaceutical compositions and method employing such compounds |
US4791120A (en) * | 1987-12-31 | 1988-12-13 | The Boc Group, Inc. | 4-heteropentacyclic-4-[N-(phenyl)amino] piperidine derivatives and pharmaceutical compositions and method employing such compounds |
US4801615A (en) * | 1987-12-31 | 1989-01-31 | The Boc Group, Inc. | 4-heterohexacyclic-4-(N-(phenyl)amido) piperidine derivatives and pharmaceutical compositions and method employing such compounds |
US5019583A (en) * | 1989-02-15 | 1991-05-28 | Glaxo Inc. | N-phenyl-N-(4-piperidinyl)amides useful as analgesics |
US5145967A (en) * | 1989-04-20 | 1992-09-08 | Anaquest, Inc. | Method for preparing 4-alkoxyalkyl-4-phenylaminopiperdines and derivatives thereof |
USRE34201E (en) * | 1989-04-20 | 1993-03-23 | Anaquest, Inc. | N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds |
US5053411A (en) * | 1989-04-20 | 1991-10-01 | Anaquest, Inc. | N-aryl-N-[4-(1-heterocyclicalkyl)piperidinyl]amides and pharmaceutical compositions and methods employing such compounds |
US4994471A (en) * | 1989-05-12 | 1991-02-19 | Boc, Inc. | N-aryl-N-(1-substituted-3-alkoxy-4-piperidinyl)amides and pharmaceutical compositions and methods employing such compounds |
US4939161A (en) * | 1989-05-12 | 1990-07-03 | Boc, Inc. | Analgesic N-aryl-N-[1-substituted-3,5-dimethyl-4-piperidinyl]amides |
US5100903A (en) * | 1989-05-12 | 1992-03-31 | Anaquest, Inc. | N-aryl-n-(1-substituted-3-alkoxy-4-piperidinyl)amides and pharmaceutical compositions and methods employing such compounds |
US5126455A (en) * | 1989-12-13 | 1992-06-30 | Glaxo Inc. | Preparation of substituted alkali metal piperidine-4-carboxylates |
US5039804A (en) * | 1989-12-13 | 1991-08-13 | Glaxo Inc. | Preparation of substituted alkali metal piperidine-4-carboxylates |
US5130321A (en) * | 1990-12-18 | 1992-07-14 | Glaxo Inc. | Analgesic n-phenyl-n-(3-or 1-3-me-4-piperidinyl)amides |
US5214148A (en) * | 1990-12-18 | 1993-05-25 | Glaxo Inc. | Analgesic N-phenyl-N-(3-OR1 -3-ME-4-piperidinyl)amides |
FR2676054B1 (fr) * | 1991-05-03 | 1993-09-03 | Sanofi Elf | Nouveaux composes n-alkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
GB9316863D0 (en) * | 1993-08-13 | 1993-09-29 | Glaxo Group Ltd | Chemical process |
US5489689A (en) * | 1993-09-30 | 1996-02-06 | Mallinckrodt Chemical, Inc. | Preparation of piperidine derivatives |
US6835194B2 (en) * | 1999-03-18 | 2004-12-28 | Durect Corporation | Implantable devices and methods for treatment of pain by delivery of fentanyl and fentanyl congeners |
US6541021B1 (en) | 1999-03-18 | 2003-04-01 | Durect Corporation | Devices and methods for pain management |
EP1182192A4 (en) * | 1999-04-09 | 2002-06-05 | Mochida Pharm Co Ltd | 4-HYDROXYPIPERIDINE DERIVATIVES WITH ANTI-ARRHYTHMIC EFFECT |
US6635661B2 (en) | 2000-05-25 | 2003-10-21 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US7361666B2 (en) * | 1999-05-25 | 2008-04-22 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US6677332B1 (en) | 1999-05-25 | 2004-01-13 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
ATE340159T1 (de) * | 1999-12-06 | 2006-10-15 | Mallinckrodt Inc | Verfahren zur herstellung von alfentanil, sufentanil und remifentanil |
US7074803B2 (en) * | 2001-03-02 | 2006-07-11 | Durect Corporation | Opioid formulations |
US20040102476A1 (en) * | 2002-11-25 | 2004-05-27 | Chan Tai Wah | High concentration formulations of opioids and opioid derivatives |
US20090030041A1 (en) * | 2004-09-14 | 2009-01-29 | Toshihiro Takahashi | N-substituted N-(4-piperidinyl) Amide Derivative |
JP2008088057A (ja) * | 2005-03-23 | 2008-04-17 | Nippon Chemiphar Co Ltd | N−置換−n−(4−ピペリジニル)アミド誘導体 |
EP1966140A1 (en) * | 2005-11-17 | 2008-09-10 | Mallinckrodt, Inc. | Process for synthesizing remifentanil |
US20080312448A1 (en) * | 2006-01-24 | 2008-12-18 | Cheng Brian K | Process for Synthesizing Remifentanil |
EP1867635A1 (en) * | 2006-06-15 | 2007-12-19 | Kern Pharma, S.L. | Process for preparing remifentanil, intermediates thereof, use of said intermediates and processes for their preparation |
US20080009782A1 (en) * | 2006-06-28 | 2008-01-10 | Alza Corporation | Methods and Devices for Transdermal Electrotransport Delivery of Lofentanil and Carfentanil |
WO2008005423A1 (en) * | 2006-07-03 | 2008-01-10 | Cambrex Charles City, Inc. | Improved method of making sufentanil |
WO2008066708A2 (en) * | 2006-11-29 | 2008-06-05 | Mallinckrodt Inc. | New process for remifentanil synthesis |
WO2010027770A1 (en) * | 2008-09-04 | 2010-03-11 | Mallinckrodt Inc. | Crystalline forms of sufentanil citrate |
WO2010053944A1 (en) * | 2008-11-04 | 2010-05-14 | Cambrex Charles City, Inc. | Improved method of making piperidine derivatives |
US8946433B2 (en) | 2010-09-17 | 2015-02-03 | Mallinckrodt Llc | Process for the preparation of sufentanil base and related compounds |
EP2455377B1 (de) | 2010-11-11 | 2014-07-09 | hameln rds gmbh | Synthese von Fentanyl Analoga |
AU2011336467A1 (en) | 2010-12-01 | 2013-07-04 | Spinal Modulation, Inc. | Agent delivery systems for selective neuromodulation |
SG11201508431VA (en) * | 2013-03-13 | 2015-11-27 | Harvard College | Stapled and stitched polypeptides and uses thereof |
US10633336B2 (en) | 2014-12-19 | 2020-04-28 | The Broad Institute, Inc. | Dopamine D2 receptor ligands |
US10752588B2 (en) | 2014-12-19 | 2020-08-25 | The Broad Institute, Inc. | Dopamine D2 receptor ligands |
EP3302473B1 (en) | 2015-05-27 | 2020-07-08 | SpecGx LLC | Preparation of sufentanil citrate and sufentanil base |
CN106854203B (zh) * | 2015-12-08 | 2020-12-01 | 江苏恩华药业股份有限公司 | 枸橼酸舒芬太尼的新晶型及其制备方法 |
ES2699636T3 (es) | 2016-01-29 | 2019-02-12 | Bioka S R O | Nuevo procedimiento para la preparación de derivados de N-fenil-N-(4-piperidinil) amida, como remifentanilo y carfentanilo |
CN108503579B (zh) * | 2018-03-28 | 2021-03-26 | 南京医科大学 | 芬太尼类似物及其应用 |
CN113214139B (zh) * | 2020-02-03 | 2022-03-04 | 江苏谛奇医药科技有限公司 | 哌啶酰胺类衍生物及其制备方法、其药物组合物、其单晶培养方法及其应用 |
IL299091A (en) | 2020-08-14 | 2023-02-01 | Novartis Ag | Heteroaryl substituted spiropiperidinyl derivatives and their medicinal uses |
CN114262320A (zh) * | 2021-12-28 | 2022-04-01 | 宜昌人福药业有限责任公司 | 一种利用连续流微通道反应器制备苯胺基哌啶类药物的合成方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL135583C (pl) * | 1961-10-10 | |||
US3171838A (en) * | 1961-10-10 | 1965-03-02 | Res Lab Dr C Janssen N V | Aroylalkyl and hydroxyaralkyl derivatives of 4-(n-arylalkanamido)-piperidines and related compounds |
-
1976
- 1976-01-13 US US05/648,685 patent/US3998834A/en not_active Expired - Lifetime
- 1976-02-23 NO NO760591A patent/NO146162C/no unknown
- 1976-02-24 NZ NZ180096A patent/NZ180096A/xx unknown
- 1976-02-27 SE SE7602740A patent/SE426486B/xx active Protection Beyond IP Right Term
- 1976-02-27 CA CA246,697A patent/CA1080232A/en not_active Expired
- 1976-03-09 LU LU74511A patent/LU74511A1/xx unknown
- 1976-03-10 FR FR7606870A patent/FR2303546A1/fr active Granted
- 1976-03-10 GB GB9593/76A patent/GB1538938A/en not_active Expired
- 1976-03-11 HU HU76JA00000751A patent/HU172963B/hu unknown
- 1976-03-11 DE DE19762610228 patent/DE2610228A1/de active Granted
- 1976-03-12 DK DK110376A patent/DK148960C/da not_active IP Right Cessation
- 1976-03-12 FI FI760646A patent/FI61481C/fi not_active IP Right Cessation
- 1976-03-12 CH CH310476A patent/CH629486A5/de not_active IP Right Cessation
- 1976-03-12 CZ CS761632A patent/CZ278060B6/cs unknown
- 1976-03-12 JP JP51026226A patent/JPS5946217B2/ja not_active Expired
- 1976-03-12 PH PH18204A patent/PH12746A/en unknown
- 1976-03-12 IT IT48556/76A patent/IT1057988B/it active
- 1976-03-12 YU YU652/76A patent/YU39960B/xx unknown
- 1976-03-12 NL NLAANVRAGE7602612,A patent/NL185279C/xx not_active IP Right Cessation
- 1976-03-12 IE IE527/76A patent/IE42512B1/en not_active IP Right Cessation
- 1976-03-12 PL PL1976187910A patent/PL102474B1/pl unknown
- 1976-03-12 SU SU762332950A patent/SU1227109A3/ru active
- 1976-03-12 PT PT64898A patent/PT64898B/pt unknown
- 1976-03-12 AT AT184676A patent/AT359493B/de not_active IP Right Cessation
- 1976-03-12 ES ES446034A patent/ES446034A1/es not_active Expired
- 1976-03-12 BG BG032601A patent/BG28259A3/xx unknown
- 1976-03-12 IL IL49204A patent/IL49204A/xx unknown
- 1976-03-15 AU AU12006/76A patent/AU503632B2/en not_active Expired
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
PL102474B1 (pl) | A method of producing new derivatives of n-/4-piperidinylo/-amines | |
US3381009A (en) | Triazole-(4,3-a)-pyridines | |
US20080096922A1 (en) | Novel Sulfonamide derivative | |
KR100244626B1 (ko) | 5-ht1a 길항제로서의 피페라진 유도체, 이의 제조방법 및 이를 함유하는 약제학적 조성물 | |
ZA200306037B (en) | Derivatives of N-(arylsulfonyl)beta-aminoacids comprising a substituted aminomethyl group, the preparation method thereof and the pharmaceutical compositions containing same. | |
NZ235985A (en) | N-(substituted piperidinyl- and piperazinyl-alkyl) carbamic acids, esters, amides and (thio) urea derivatives | |
NZ601794A (en) | Di - substituted pyridine derivatives as anticancers | |
PL164136B1 (pl) | Sposób wytwarzania nowych pochodnych pirolidyny PL PL PL PL PL PL PL PL PL | |
JP2009539938A5 (pl) | ||
CA2674548A1 (en) | Novel n-(2-aminophenyl) benzamide derivative having urea structure | |
AU747815B2 (en) | Cyclic amide compounds | |
CA2369005A1 (en) | Inhibitors of lfa-1 binding to icams and uses thereof | |
CA2632941A1 (en) | New phenanthridine derivatives as bradykinin antagonists | |
CA1266657A (en) | Imidazolyl alkyl guanidine derivatives, processes for their preparation and pharmaceutical preparations containing these compounds | |
US20040010147A1 (en) | Cyclic amine compounds and pharmaceutical composition containing the same | |
JPH02139026A (ja) | フルオロケミカル界面活性剤およびその製造方法 | |
CA1247101A (en) | 5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-one compounds, intermediates and methods for their preparation, and pharmaceutical compositions containing them | |
JPWO2002022588A1 (ja) | 新規ピリミジン誘導体及び新規ピリジン誘導体 | |
US6498169B1 (en) | Cyclic amine compounds and pharmaceutical composition containing the same | |
PT99465A (pt) | Processo para preparacao de inibidores da oxisulfonil ureia acil-coa:colesterol acil-transferase (acat) | |
Rasmussen et al. | A versatile synthesis of novel N, N, N ″-trisubstituted guanidines | |
NO176097B (no) | Analogifremgangsmåte for fremstilling av terapeutisk aktive substituerte cykloheksener | |
Stark et al. | Development of FUB 181, a Selective Histamine H3‐Receptor Antagonist of High Oral in Vivo Potency with 4‐(? gv‐(Arylalkyloxy) alkyl)‐1H‐imidazole Structure | |
EP0145459A3 (en) | Process for the production of chemical compounds | |
WO1994021611A1 (en) | Amide derivatives as 5-ht1a ligands |