AR036596A1 - Derivados de 4,5-dihidro-1h-pirazol que tienen actividad antagonista de cb1 - Google Patents
Derivados de 4,5-dihidro-1h-pirazol que tienen actividad antagonista de cb1Info
- Publication number
- AR036596A1 AR036596A1 ARP020103506A ARP020103506A AR036596A1 AR 036596 A1 AR036596 A1 AR 036596A1 AR P020103506 A ARP020103506 A AR P020103506A AR P020103506 A ARP020103506 A AR P020103506A AR 036596 A1 AR036596 A1 AR 036596A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- alkyl
- whose
- substituted
- amino
- Prior art date
Links
- 229940124802 CB1 antagonist Drugs 0.000 title 1
- -1 trifluoromethoxy, nitro, amino Chemical group 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 229910052757 nitrogen Inorganic materials 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000001544 thienyl group Chemical group 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 125000000468 ketone group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000004076 pyridyl group Chemical group 0.000 abstract 4
- 229910052717 sulfur Inorganic materials 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 102000018208 Cannabinoid Receptor Human genes 0.000 abstract 2
- 108050007331 Cannabinoid receptor Proteins 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 125000004404 heteroalkyl group Chemical group 0.000 abstract 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract 2
- 125000006413 ring segment Chemical group 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 abstract 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical class C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 abstract 1
- 125000006548 C4-10 heterocycloalkyl group Chemical group 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 239000005557 antagonist Substances 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000002393 azetidinyl group Chemical group 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 1
- 229930003827 cannabinoid Natural products 0.000 abstract 1
- 239000003557 cannabinoid Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 abstract 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 abstract 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 abstract 1
Classifications
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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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
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- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
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- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Oncology (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Virology (AREA)
- Toxicology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Derivados de 4,5-dihidro-1H-pirazol que son potentes antagonistas de receptores (CB1) de cannabinoide con utilidad para el tratamiento de enfermedades conectadas con desórdenes del sistema cannabinoide. Los compuestos tienen la fórmula general (1), en donde: R y R1 representan independientemente fenilo, tienilo o piridilo cuyos grupos pueden estar sustituidos con 1, 2, 3 ó 4 sustituyentes Y, los cuales pueden ser iguales o diferentes, del grupo alquilo o alcoxi C1-3, hidroxi, halógeno, trifluorometilo, trifluorometiltio, trifluorometoxi, nitro, amino, mono- o dialquil C1-2-amino, mono o dialquil C1-2-amido, alquil C1-3-sulfonilo, dimetilsulfamido, alcoxi C1-3-carbonilo, carboxilo, trifluorometilsulfonilo, ciano, carbamoílo, sulfamoílo y acetilo, o R y/o R1 representa naftilo; R2 representa hidrógeno, hidroxi, alcoxi C1-3, acetiloxi o propioniloxi; R3 representa un átomo de hidrógeno o un grupo alquilo C1-8 ramificado o no ramificado o un grupo cicloalquilo C3-7 donde el grupo alquilo o cicloalquilo puede estar sustituido con un grupo hidroxi; R4 representa un grupo heteroalquilo C2-10 ramificado o no ramificado, un grupo heterocicloalquilo C3-8 no aromático o un grupo heterocicloalquilo-alquilo C4-10 no aromático cuyos grupos contienen uno o más heteroátomos del grupo (O, N, S) o un grupo -SO2-, cuyo grupo heteroalquilo C2-10 ramificado o no ramificado, grupo heterocicloalquilo C3-8 no aromático o grupo heterocicloalquilo-alquilo C4-10 no aromático pueden estar sustituidos con un grupo ceto, grupo trifluorometilo, grupo alquilo C1-3, hidroxi, amino, monoalquilamino, o dialquilamino o un átomo de flúor, o R4 representa un grupo amino, hidroxi, fenoxi o benciloxi, o R4 representa un grupo alcoxi C1-8, alquenilo C3-8, cicloalquenilo C5-8 o cicloalquenilalquilo C6-9 cuyos grupos pueden contener un átomo de azufre, nitrógeno u oxígeno, un grupo ceto o un grupo -SO2-, cuyos grupos alcoxi, alquenilo y cicloalquenilo pueden estar sustituidos con un grupo hidroxi, un grupo trifluorometilo, un grupo amino, un grupo monoalquilamino o un grupo dialquilamino o un átomo de flúor, o R4 representa un grupo alquilo C2-5 cuyo grupo alquilo contiene un átomo de flúor, o R4 representa un grupo imidazolilalquilo, bencilo, piridilmetilo, fenetilo o tienilo, o R4 representa un grupo fenilo, bencilo, piridilo, tienilo, piridilmetilo o fenetilo sustituido en donde los anillo aromáticos están sustituidos con 1, 2 ó 3 de los sustituyentes Y, en donde Y tiene los significados como se indicó anteriormente, o cuando R3 es H o metilo, R4 puede representar un grupo NR6R7 en donde R6 y R7 son iguales o diferentes y representan alquilo C2-4, trifluoroalquilo C2-4 o R6 representa un grupo metilo con la condición que R7 represente un grupo alquilo C2-4, o R6 y R7 junto con el átomo de nitrógeno al cual ellos están unidos formen un grupo molecular heterocíclico saturado o insaturado que tiene 4 a 8 átomos de anillo cuyo grupo heterocíclico puede contener un átomo de oxígeno, o de azufre o un grupo ceto o un grupo -SO2- o un átomo de nitrógeno adicional, cuyo grupo molecular heterocíclico saturado o insaturado puede estar sustituido con un grupo alquilo C1-4, o, R3 y R4 junto con el átomo de nitrógeno al cual ellos están unidos forman un grupo molecular heterocíclico monocíclico o bicíclico, saturado o insaturado que tiene 4 a 10 átomos de anillo, cuyo grupo heterocíclico puede contener uno o más átomos del grupo (O, N, S) o un grupo ceto o un grupo -SO2-, cuyos grupos moleculares pueden estar sustituidos con un grupo alquilo C1-4, hidroxialquilo, fenilo, tienilo, piridilo, amino, monoalquilaminoalquilo, dialquilaminoalquilo, monoalquilamino, dialquilamino, aminoalquilo, azetidinilo, pirrolidinilo, piperidinilo o hexahidro-1H-azepinilo; R5 representa bencilo, fenilo, tienilo o piridilo los cuales pueden estar sustituidos con 1, 2, 3 ó 4 sustituyentes Y, en donde Y tiene el significado como se indicó anteriormente, los cuales pueden ser iguales o diferentes, o R5 representa alquilo C1-8 ramificado o no ramificado, alquenilo C3-8, cicloalquilo C3-10, bicicloalquilo C3-10, tricicloalquilo C3-10 o cicloalquenilo C5-8 o R5 representa naftilo; y tautómeros, prodrogas, estereoisómeros y sales de los mismos. Se describen métodos para la preparación de estos compuestos, y composiciones farmacéuticas que contienen uno o más de estos compuestos como un componente activo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203850 | 2001-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR036596A1 true AR036596A1 (es) | 2004-09-22 |
Family
ID=8181043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020103506A AR036596A1 (es) | 2001-09-21 | 2002-09-18 | Derivados de 4,5-dihidro-1h-pirazol que tienen actividad antagonista de cb1 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7528162B2 (es) |
| EP (1) | EP1429761B1 (es) |
| JP (1) | JP4313671B2 (es) |
| KR (1) | KR100903760B1 (es) |
| CN (2) | CN101659639A (es) |
| AR (1) | AR036596A1 (es) |
| AT (1) | ATE344663T1 (es) |
| AU (1) | AU2002333852B2 (es) |
| BR (1) | BR0212044A (es) |
| CA (1) | CA2456606C (es) |
| DE (1) | DE60215960T2 (es) |
| DK (1) | DK1429761T3 (es) |
| ES (1) | ES2272809T3 (es) |
| HR (1) | HRP20040085A2 (es) |
| HU (1) | HUP0401567A3 (es) |
| IL (2) | IL160081A0 (es) |
| MX (1) | MXPA04002583A (es) |
| NO (1) | NO20041176L (es) |
| PL (1) | PL368441A1 (es) |
| PT (1) | PT1429761E (es) |
| RU (1) | RU2299199C2 (es) |
| SI (1) | SI1429761T1 (es) |
| UA (1) | UA78523C2 (es) |
| WO (1) | WO2003026647A1 (es) |
| ZA (1) | ZA200402099B (es) |
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| NL158178B (nl) * | 1974-07-12 | 1978-10-16 | Philips Nv | Werkwijze ter bereiding van insekticide preparaten die een pyrazolinederivaat bevatten, aldus verkregen gevormde preparaten, en werkwijze ter bereiding van pyrazolinederivaten met insekticide werking. |
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| UA74367C2 (uk) * | 2000-03-23 | 2005-12-15 | Сольве Фармас'Ютікалз Б.В. | ПОХІДНІ 4,5-ДИГІДРО-1Н-ПІРАЗОЛУ, ЩО ВИЯВЛЯЮТЬ АНТАГОНІСТИЧНУ АКТИВНІСТЬ ЩОДО СВ<sub>1</sub>, СПОСІБ ЇХ ОДЕРЖАННЯ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ТА СПОСІБ ЇЇ ВИГОТОВЛЕННЯ, СПОСІБ ЛІКУВАННЯ ЗАХВОРЮВАНЬ (ВАРІАНТИ) |
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