AR041877A1 - Procedimiento para la preparacion de compuestos de pirrolidiniletilamina mediante una aminacion de arilo mediada por cobre - Google Patents
Procedimiento para la preparacion de compuestos de pirrolidiniletilamina mediante una aminacion de arilo mediada por cobreInfo
- Publication number
- AR041877A1 AR041877A1 ARP030103976A ARP030103976A AR041877A1 AR 041877 A1 AR041877 A1 AR 041877A1 AR P030103976 A ARP030103976 A AR P030103976A AR P030103976 A ARP030103976 A AR P030103976A AR 041877 A1 AR041877 A1 AR 041877A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkoxy
- alkyl
- optionally substituted
- fluoro
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 238000005576 amination reaction Methods 0.000 title abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000556 agonist Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000005543 phthalimide group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Abstract
Procedimiento para la preparación de compuestos que son útiles como agonistas kappa. Reivindicación 1: Un procedimiento de una etapa o de múltiples etapas para la preparación de un compuesto de fórmula (1), y un estereoisómero del mismo, en la que: A es hidrógeno, hidroxi, alquilo C1-6 (preferiblemente C1-4), fluoroalquilo C1-6 (preferiblemente C1-4) (particularmente -CF3), alcoxi C1-6 (preferiblemente C1-4) u OY, siendo Y un grupo protector de hidroxi o A, tomado conjuntamente con su hidrógeno geminal, es un grupo oxo; Ar1 es fenilo opcionalmente sustituido con uno o más (preferiblemente uno a dos) sustituyentes seleccionados de fluoro, alquilo C1-4, alcoxi C1-4, alcoxi(C1-4)-alcoxi(C1-4), trifluorometilo, carboxialcoxi C1-4 y alcoxi(C1-4)-carbonilalcoxi(C1-4); Ar2 es fenilo, naftilo, piridilo, tienilo, furilo, pirrolilo o pirimidilo, estando opcionalmente sustituido cada uno con uno o más (preferiblemente uno o dos) sustituyentes seleccionados de fluoro, alquilo C1-4, alcoxi C1-4, dialquil(C1-4)amino y fluoroalquilo C1-4; R1 es alquilo C1-6 o bencilo en el que el resto fenilo del citado bencilo está opcionalmente sustituido con alcoxi C1-6 u OY, siendo Y un grupo protector de hidroxi; y R2 y R3 se seleccionan independientemente de hidrógeno, alquilo C1-7 opcionalmente sustituido con uno o más (preferiblemente uno a cinco) grupos hidroxi o halo, cicloalquilo C3-6, alquenilo C2-6, alquinilo C2-6, alcoxi C1-7 (preferiblemente (C1-5), fenilo opcionalmente sustituido con fluoro (preferiblemente sustituido con uno o dos grupos fluoro), fenilalquilo C1-7 (preferiblemente C1-6), estando opcionalmente sustituido el grupo fenilo con fluoro, y -(CH2)nX-R4, siendo n uno o dos, siendo XO o S y siendo R4 alquilo C1-3 o, cuando Ar2 es fenilo, -Ar2-C(=O)-N(R2)- es un grupo ftalimida y R3 es alquilo C1-7; o R2 y R3 junto con el átomo de nitrógeno al que están unidos forman un anillo de pirrolidina, piperidina o morfolina, opcionalmente sustituido con alquilo C1-3 o fluoro; caracterizado porque comprende una etapa en la que el enlace N-Ar2 se construye mediante una aminación de arilo mediada por cobre.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42332802P | 2002-11-01 | 2002-11-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR041877A1 true AR041877A1 (es) | 2005-06-01 |
Family
ID=32230416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP030103976A AR041877A1 (es) | 2002-11-01 | 2003-10-30 | Procedimiento para la preparacion de compuestos de pirrolidiniletilamina mediante una aminacion de arilo mediada por cobre |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20040152896A1 (es) |
| AR (1) | AR041877A1 (es) |
| AU (1) | AU2003269399A1 (es) |
| TW (1) | TW200420537A (es) |
| WO (1) | WO2004039785A1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100450998C (zh) | 2003-11-11 | 2009-01-14 | 卫材R&D管理有限公司 | 脲衍生物的制备方法 |
| SG11201700777VA (en) | 2014-08-04 | 2017-02-27 | Nuevolution As | Optionally fused heterocyclyl-substituted derivatives of pyrimidine useful for the treatment of inflammatory, metabolic, oncologic and autoimmune diseases |
| US11685727B2 (en) | 2019-12-20 | 2023-06-27 | Nuevolution A/S | Compounds active towards nuclear receptors |
| JP2021098692A (ja) | 2019-12-20 | 2021-07-01 | ヌエヴォリューション・アクティーゼルスカブＮｕｅｖｏｌｕｔｉｏｎ Ａ／Ｓ | 核内受容体に対して活性の化合物 |
| JP7713954B2 (ja) | 2020-03-31 | 2025-07-28 | ヌエヴォリューション・アクティーゼルスカブ | 核内受容体に対して活性な化合物 |
| MX2022012260A (es) | 2020-03-31 | 2022-11-30 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| CN116332710B (zh) * | 2023-03-27 | 2024-11-26 | 合肥工业大学 | 一种金属催化的苄基醚的制备方法及制备的苄基醚 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764625A (en) * | 1980-12-12 | 1988-08-16 | Xerox Corporation | Process for preparing arylamines |
| IL117440A0 (en) * | 1995-03-31 | 1996-07-23 | Pfizer | Pyrrolidinyl hydroxamic acid compounds and their production process |
| DE19523502A1 (de) * | 1995-06-28 | 1997-01-02 | Merck Patent Gmbh | Kappa-Opiatagonisten für entzündliche Darmerkrankungen |
| USRE38133E1 (en) * | 1996-03-08 | 2003-06-03 | Adolor Corporation | Kappa agonist compounds and pharmaceutical formulations thereof |
| US5688955A (en) * | 1996-03-08 | 1997-11-18 | Adolor Corporation | Kappa agonist compounds and pharmaceutical formulations thereof |
| TNSN97092A1 (ar) * | 1996-09-18 | 1999-12-31 | Agouron Pharma | مثبطات انزيم بروتيني فلزي وتركيبات صيدلانية تحتوي على تلك المثبتطات واستخدامها الصيدلاني وطرق ومركبات وسيطة مفيدة لتحضير التركيبات المذكورة. |
| EP0982297A3 (en) * | 1998-08-24 | 2001-08-01 | Pfizer Products Inc. | Process for the preparation of hydroxy-pyrrolidinyl hydroxamic acid derivatives being opioid kappa receptor agonists |
| EP1390340B1 (en) * | 2001-04-24 | 2017-03-01 | Massachusetts Institute Of Technology | Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds |
| EP1461317A2 (en) * | 2001-04-30 | 2004-09-29 | Pfizer Products Inc. | Process for preparing hydroxypyrrolidinyl ethylamine compounds useful as kappa agonists |
| CA2477634A1 (en) * | 2002-02-28 | 2003-09-04 | Pfizer Products Inc. | Crystalline anhydrous and monohydrate benzoate salts of (2's,3s)-3-hydroxy-n-{2{n-methyl-n-4-(n-propylamino-carbonyl)phenyl]amino-2-phenyl}-ethylpyrrolidine |
| US7223870B2 (en) * | 2002-11-01 | 2007-05-29 | Pfizer Inc. | Methods for preparing N-arylated oxazolidinones via a copper catalyzed cross coupling reaction |
-
2003
- 2003-10-22 AU AU2003269399A patent/AU2003269399A1/en not_active Abandoned
- 2003-10-22 WO PCT/IB2003/004676 patent/WO2004039785A1/en not_active Ceased
- 2003-10-30 AR ARP030103976A patent/AR041877A1/es unknown
- 2003-10-31 US US10/699,106 patent/US20040152896A1/en not_active Abandoned
- 2003-10-31 TW TW092130478A patent/TW200420537A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20040152896A1 (en) | 2004-08-05 |
| TW200420537A (en) | 2004-10-16 |
| WO2004039785A1 (en) | 2004-05-13 |
| AU2003269399A1 (en) | 2004-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |