PT2205558E - Amidas de n-fenil-pirrolidinilmetilpirrolidina substituídas e sua utilização terapêutica como moduladores do receptor h3 da histamina - Google Patents
Amidas de n-fenil-pirrolidinilmetilpirrolidina substituídas e sua utilização terapêutica como moduladores do receptor h3 da histamina Download PDFInfo
- Publication number
- PT2205558E PT2205558E PT08839706T PT08839706T PT2205558E PT 2205558 E PT2205558 E PT 2205558E PT 08839706 T PT08839706 T PT 08839706T PT 08839706 T PT08839706 T PT 08839706T PT 2205558 E PT2205558 E PT 2205558E
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- Prior art keywords
- methyl
- pyrrolidin
- ylmethyl
- phenyl
- quot
- Prior art date
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- 102000004384 Histamine H3 receptors Human genes 0.000 title description 24
- 108090000981 Histamine H3 receptors Proteins 0.000 title description 24
- 150000001408 amides Chemical class 0.000 title description 3
- 230000001225 therapeutic effect Effects 0.000 title description 3
- -1 benzoimidazolyl Chemical group 0.000 claims description 133
- 150000001875 compounds Chemical class 0.000 claims description 131
- 150000003839 salts Chemical class 0.000 claims description 43
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- 238000002360 preparation method Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
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- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
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- JFCIRXKCYXZKKC-UHFFFAOYSA-N n-[2-methyl-4-[3-[(2-methylpyrrolidin-1-yl)methyl]pyrrolidin-1-yl]phenyl]-6-(phenylmethoxymethyl)pyridine-3-carboxamide Chemical compound CC1CCCN1CC1CN(C=2C=C(C)C(NC(=O)C=3C=NC(COCC=4C=CC=CC=4)=CC=3)=CC=2)CC1 JFCIRXKCYXZKKC-UHFFFAOYSA-N 0.000 claims description 4
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- GTJIDFLZYALYBZ-VQTJNVASSA-N 5-fluoro-2-methyl-n-[2-methyl-4-[(3r)-3-[[(2s)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]phenyl]benzamide Chemical compound C[C@H]1CCCN1C[C@@H]1CN(C=2C=C(C)C(NC(=O)C=3C(=CC=C(F)C=3)C)=CC=2)CC1 GTJIDFLZYALYBZ-VQTJNVASSA-N 0.000 claims description 3
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- PGMSQXCSQIDOIK-ZWKOTPCHSA-N n-[2-methyl-4-[(3r)-3-[[(2s)-2-methylpyrrolidin-1-yl]methyl]pyrrolidin-1-yl]phenyl]furan-3-carboxamide Chemical compound C[C@H]1CCCN1C[C@@H]1CN(C=2C=C(C)C(NC(=O)C3=COC=C3)=CC=2)CC1 PGMSQXCSQIDOIK-ZWKOTPCHSA-N 0.000 claims description 2
- QGSSYCAXPLSKOO-UHFFFAOYSA-N n-[2-methyl-4-[3-[(2-methylpyrrolidin-1-yl)methyl]pyrrolidin-1-yl]phenyl]-2,3-dihydro-1-benzofuran-5-carboxamide Chemical compound CC1CCCN1CC1CN(C=2C=C(C)C(NC(=O)C=3C=C4CCOC4=CC=3)=CC=2)CC1 QGSSYCAXPLSKOO-UHFFFAOYSA-N 0.000 claims description 2
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- 239000008247 solid mixture Substances 0.000 description 1
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- NDRHPVMQJMPSAP-RYUDHWBXSA-N tert-butyl (3s)-3-[(2s)-2-methylpyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate Chemical compound C[C@H]1CCCN1C(=O)[C@@H]1CN(C(=O)OC(C)(C)C)CC1 NDRHPVMQJMPSAP-RYUDHWBXSA-N 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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Classifications
-
- 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
- C07D401/12—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
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
- C07D405/02—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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
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| RU (1) | RU2477721C2 (enExample) |
| WO (1) | WO2009052063A1 (enExample) |
| ZA (1) | ZA201002113B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS52235B (sr) | 2007-10-17 | 2012-10-31 | Sanofi | Supstituisani n-fenil-bipirolidin karboksamidi i njihova terapeutska upotreba |
| HRP20110953T1 (hr) | 2007-10-17 | 2012-01-31 | Sanofi | Supstituirani n-fenilbipirolidinkarboksamidi i njihova upotreba u terapiji |
| ES2378011T3 (es) | 2007-10-17 | 2012-04-04 | Sanofi | N-fenil-bipirrolidin ureas sustituidas y uso terapéutico de las mismas |
| AR074467A1 (es) | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Tetrahidropiran espiro pirrolidinonas y piperidinonas sustituidas, composiciones farmaceuticas que las contienen y uso de las mismas en el tratamiento y/o prevencion de enfermedades del snc ,tales como alzheimer y parkinson, entre otras. |
| AR074466A1 (es) * | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Piperidina espiro pirrolidinona y piperidinona sustituidas y su uso terapeutico en enfermedades mediadas por la modulacion de los receptores h3. |
| AR083718A1 (es) | 2010-05-11 | 2013-03-20 | Sanofi Aventis | Fenil cicloalquil pirrolidina (piperidina) espirolactamas y amidas sustituidas, preparacion y uso terapeutico de las mismas |
| TW201206444A (en) | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted N-heteroaryl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof |
| AR081382A1 (es) * | 2010-05-11 | 2012-08-29 | Sanofi Aventis | Derivados de n-heterocicloalquil bipirrolidinilfenil amida sustituidos, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades del sistema nervioso central. |
| JP5833105B2 (ja) | 2010-05-11 | 2015-12-16 | サノフイ | 置換ｎ−ヘテロアリールスピロラクタムビピロリジン類、その製造及び治療的使用 |
| TW201206901A (en) | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted N-heteroaryl bipyrrolidine carboxamides, preparation and therapeutic use thereof |
| JP5766278B2 (ja) | 2010-05-11 | 2015-08-19 | サノフイ | 置換されたｎ−アルキルおよびｎ−アシルテトラヒドロ−イソキノリン誘導体、それらの製造および治療上の使用 |
| RU2562461C1 (ru) * | 2014-04-30 | 2015-09-10 | Федеральное государственное бюджетное учреждение науки Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) | Спин-меченое производное кинуренина и способ его получения |
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| PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| EP1556046A1 (en) * | 2002-10-23 | 2005-07-27 | Janssen Pharmaceutica N.V. | Phenylpiperidines and phenylpyrrolidines as histamine h3 receptor modulators |
| US7223788B2 (en) * | 2003-02-14 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Substituted N-aryl heterocycles, process for their preparation and their use as medicaments |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US7951826B2 (en) * | 2005-03-17 | 2011-05-31 | Eli Lilly And Company | Pyrrolidine derivatives as histamine H3 receptor antagonists |
| AU2006232871B9 (en) * | 2005-04-01 | 2011-11-24 | Eli Lilly And Company | Histamine H3 receptor agents, preparation and therapeutic uses |
| JP5193033B2 (ja) * | 2005-07-01 | 2013-05-08 | イーライ リリー アンド カンパニー | ヒスタミンｈ３受容体薬剤、製剤及び治療的使用 |
| WO2007048595A1 (en) * | 2005-10-27 | 2007-05-03 | Ucb Pharma, S.A. | Compounds comprising a lactam or a lactam derivative moiety, processes for making them, and their uses |
| BRPI0707872A2 (pt) * | 2006-02-15 | 2011-05-10 | Sanofi Aventis | arildiidroisoquinolinonas substituÍdas por azaciclila, processo para sua preparaÇço e seu uso como medicamentos |
| RS52235B (sr) | 2007-10-17 | 2012-10-31 | Sanofi | Supstituisani n-fenil-bipirolidin karboksamidi i njihova terapeutska upotreba |
| HRP20110953T1 (hr) | 2007-10-17 | 2012-01-31 | Sanofi | Supstituirani n-fenilbipirolidinkarboksamidi i njihova upotreba u terapiji |
| ES2378011T3 (es) * | 2007-10-17 | 2012-04-04 | Sanofi | N-fenil-bipirrolidin ureas sustituidas y uso terapéutico de las mismas |
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Also Published As
| Publication number | Publication date |
|---|---|
| NZ584691A (en) | 2011-09-30 |
| MX2010004003A (es) | 2010-04-30 |
| DK2205558T3 (da) | 2012-11-05 |
| US8227504B2 (en) | 2012-07-24 |
| MA31857B1 (fr) | 2010-11-01 |
| RU2010119530A (ru) | 2011-11-27 |
| ZA201002113B (en) | 2010-12-29 |
| HK1146055A1 (en) | 2011-05-13 |
| EP2205558B1 (en) | 2012-07-25 |
| WO2009052063A1 (en) | 2009-04-23 |
| BRPI0818766A2 (pt) | 2015-04-14 |
| JP2011500694A (ja) | 2011-01-06 |
| CA2702834C (en) | 2013-01-15 |
| AU2008312636A1 (en) | 2009-04-23 |
| MY150210A (en) | 2013-12-13 |
| ES2392122T3 (es) | 2012-12-04 |
| US20100173898A1 (en) | 2010-07-08 |
| CA2702834A1 (en) | 2009-04-23 |
| JP5377504B2 (ja) | 2013-12-25 |
| EP2205558A1 (en) | 2010-07-14 |
| IL205000A0 (en) | 2010-11-30 |
| KR20100092443A (ko) | 2010-08-20 |
| AU2008312636B2 (en) | 2013-03-14 |
| CN101903342A (zh) | 2010-12-01 |
| CN101903342B (zh) | 2012-11-21 |
| RU2477721C2 (ru) | 2013-03-20 |
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