PL442982A1 - N-podstawione pochodne 1-(1-fenylo-3-arylo)-1H-pirazol-4-ylo)metanaminy, sposób ich wytwarzania i ich zastosowanie - Google Patents

N-podstawione pochodne 1-(1-fenylo-3-arylo)-1H-pirazol-4-ylo)metanaminy, sposób ich wytwarzania i ich zastosowanie

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Publication number
PL442982A1
PL442982A1 PL442982A PL44298222A PL442982A1 PL 442982 A1 PL442982 A1 PL 442982A1 PL 442982 A PL442982 A PL 442982A PL 44298222 A PL44298222 A PL 44298222A PL 442982 A1 PL442982 A1 PL 442982A1
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PL
Poland
Prior art keywords
sub
hydrogen
methanamine
pyrazol
aryl
Prior art date
Application number
PL442982A
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English (en)
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PL247051B1 (pl
Inventor
Damian BARTUZI
Tomasz M. Wróbel
Wojciech TUPIK
Sylwia Woźniak
Agnieszka Anna Kaczor
Dariusz Matosiuk
Original Assignee
Uniwersytet Medyczny W Lublinie
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Publication date
Application filed by Uniwersytet Medyczny W Lublinie filed Critical Uniwersytet Medyczny W Lublinie
Priority to PL442982A priority Critical patent/PL247051B1/pl
Priority to US19/133,866 priority patent/US20260008754A1/en
Priority to EP23858450.2A priority patent/EP4652156A1/en
Priority to PCT/PL2023/000055 priority patent/WO2024117922A1/en
Publication of PL442982A1 publication Critical patent/PL442982A1/pl
Publication of PL247051B1 publication Critical patent/PL247051B1/pl

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Przedmiotem zgłoszenia są N-podstawione pochodne 1-(1-fenylo-3-arylo)-1H-pirazol-4-ylo)metanaminy o wzorze ogólnym 1, gdzie Y oznacza CH lub N, R<sub>1</sub> oznacza wodór, R<sub>2</sub> oznacza brak podstawnika, R<sub>3</sub> oznacza wodór, natomiast R<sub>4</sub> oznacza odpowiednio podstawiony N-propylobenzamid, benzo[b]furan, dihydrobenzo[b]furan, metylenodioksobenzen, benzoesanu etylu lub benzoesanu propylu, ich sposób wytwarzania i zastosowanie oraz sposób otrzymywania i zastosowanie N-podstawionych pochodnych 1-(1-fenylo-3-arylo)-1H-pirazol-4-ylo)metanaminy o wzorze ogólnym 1 , gdzie Y oznacza C, CH lub N, R<sub>1</sub> oznacza wodór lub grupę metylową, R<sub>2</sub> oznacza grupę metylową lub brak podstawnika, R<sub>3</sub> oznacza wodór lub grupę metylową, natomiast R<sub>4</sub> oznacza odpowiednio podstawiony dimetylopirazol, metylopirazol, dimetyloimidazo[1,2-a]pirymidynę lub izopropoksybenzen. Związki będące przedmiotem zgłoszenia otrzymuje się na drodze aminowania redukcyjnego używając pochodnych borowodorku jako reduktora, korzystnie triacetoksyborowodorku sodu, w ilości 1,4 — 2 0 eq, aminy w ilości 1,0 — 1,1 eq, korzystnie w lekkim nadmiarze, zasady, korzystnie trietyloaminy w ilości 1,0 - 1,1 eq (w przypadku użycia aminy w postaci chlorowodorku) oraz wyjściowego aldehydu. Reakcja prowadzi się w środowisku niepolarnego rozpuszczalnika, korzystnie dichloroetanu w stężeniu ok. 0,1 M. Surowy produkt oczyszcza się metodą chromatografii kolumnowej na żelu krzemionkowym stosując jako eluent mieszaninę metanolu w dichlorometanie w zakresie stężeń 2% do 5%. W celu uzyskania formy stałej i poprawy parametrów fizykochemicznych wolne zasady przeprowadza się w postać chlorowodorku, a następnie krystalizuje z polarnego rozpuszczalnika, korzystnie etanolu lub propanolu.
PL442982A 2022-11-29 2022-11-29 N-podstawione pochodne 1-(1-fenylo-3-arylo)-1H-pirazol-4-ylo) metanaminy, sposób ich wytwarzania i ich zastosowanie PL247051B1 (pl)

Priority Applications (4)

Application Number Priority Date Filing Date Title
PL442982A PL247051B1 (pl) 2022-11-29 2022-11-29 N-podstawione pochodne 1-(1-fenylo-3-arylo)-1H-pirazol-4-ylo) metanaminy, sposób ich wytwarzania i ich zastosowanie
US19/133,866 US20260008754A1 (en) 2022-11-29 2023-11-28 N-substituted derivatives of l-(l-phenyl-3-aryl)-lff-pyrazol-4-yl)methanainine, method for their production and their applications
EP23858450.2A EP4652156A1 (en) 2022-11-29 2023-11-28 N-substituted derivatives of l-(l-phenyl-3-aryl)-lff-pyrazol-4-yl)methanainine, method for their production and their applications
PCT/PL2023/000055 WO2024117922A1 (en) 2022-11-29 2023-11-28 N-substituted derivatives of l-(l-phenyl-3-aryl)-lff-pyrazol-4-yl)methanainine, method for their production and their applications

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL442982A PL247051B1 (pl) 2022-11-29 2022-11-29 N-podstawione pochodne 1-(1-fenylo-3-arylo)-1H-pirazol-4-ylo) metanaminy, sposób ich wytwarzania i ich zastosowanie

Publications (2)

Publication Number Publication Date
PL442982A1 true PL442982A1 (pl) 2024-06-03
PL247051B1 PL247051B1 (pl) 2025-05-05

Family

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Application Number Title Priority Date Filing Date
PL442982A PL247051B1 (pl) 2022-11-29 2022-11-29 N-podstawione pochodne 1-(1-fenylo-3-arylo)-1H-pirazol-4-ylo) metanaminy, sposób ich wytwarzania i ich zastosowanie

Country Status (4)

Country Link
US (1) US20260008754A1 (pl)
EP (1) EP4652156A1 (pl)
PL (1) PL247051B1 (pl)
WO (1) WO2024117922A1 (pl)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6028072A (en) * 1994-07-21 2000-02-22 G. D. Searle & Co. 3,4-substituted pyrazoles for the treatment of inflammation
US6511997B1 (en) * 1998-12-25 2003-01-28 Teikoku Hormone Mfg. Co., Ltd. Aminopyrazole derivatives
WO2004030637A2 (en) * 2002-10-01 2004-04-15 Merck & Co., Inc. Treatment of obesity and other disorders associated with excessive food intake
US20100022611A1 (en) * 2007-02-14 2010-01-28 The University Court Of The University Of Aberdeen 1,5-Diaryl-Pyrazoles As Cannabinoid Receptor Neutral Antagonists Useful As Therapeutic Agents

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014521616A (ja) * 2011-07-26 2014-08-28 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング バニロイド受容体リガンドとしての置換ヘテロ芳香族ピラゾール含有カルボキサミドおよび尿素誘導体
EP3478665A1 (en) * 2016-06-29 2019-05-08 Esteve Pharmaceuticals, S.A. Pyrazole derivatives having activity against pain

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6028072A (en) * 1994-07-21 2000-02-22 G. D. Searle & Co. 3,4-substituted pyrazoles for the treatment of inflammation
US6511997B1 (en) * 1998-12-25 2003-01-28 Teikoku Hormone Mfg. Co., Ltd. Aminopyrazole derivatives
WO2004030637A2 (en) * 2002-10-01 2004-04-15 Merck & Co., Inc. Treatment of obesity and other disorders associated with excessive food intake
US20100022611A1 (en) * 2007-02-14 2010-01-28 The University Court Of The University Of Aberdeen 1,5-Diaryl-Pyrazoles As Cannabinoid Receptor Neutral Antagonists Useful As Therapeutic Agents

Also Published As

Publication number Publication date
WO2024117922A1 (en) 2024-06-06
US20260008754A1 (en) 2026-01-08
PL247051B1 (pl) 2025-05-05
EP4652156A1 (en) 2025-11-26

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