EP1718609A1 - Substituted azetidine compounds, their preparation and use as medicaments - Google Patents
Substituted azetidine compounds, their preparation and use as medicamentsInfo
- Publication number
- EP1718609A1 EP1718609A1 EP05715383A EP05715383A EP1718609A1 EP 1718609 A1 EP1718609 A1 EP 1718609A1 EP 05715383 A EP05715383 A EP 05715383A EP 05715383 A EP05715383 A EP 05715383A EP 1718609 A1 EP1718609 A1 EP 1718609A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- optionally
- substituted
- mono
- linear
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000003814 drug Substances 0.000 title claims abstract description 49
- 150000001539 azetidines Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 238000000034 method Methods 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 24
- -1 mono-substituted phenyl group Chemical group 0.000 claims description 241
- 125000001424 substituent group Chemical group 0.000 claims description 156
- 229910052801 chlorine Inorganic materials 0.000 claims description 154
- 229910052731 fluorine Inorganic materials 0.000 claims description 137
- 125000000217 alkyl group Chemical group 0.000 claims description 135
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 129
- 229910052794 bromium Inorganic materials 0.000 claims description 124
- 125000002950 monocyclic group Chemical class 0.000 claims description 124
- 229920006395 saturated elastomer Polymers 0.000 claims description 118
- 239000000460 chlorine Substances 0.000 claims description 115
- 125000001072 heteroaryl group Chemical group 0.000 claims description 114
- 125000003118 aryl group Chemical group 0.000 claims description 95
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 86
- 125000002947 alkylene group Chemical group 0.000 claims description 79
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 76
- 125000005842 heteroatom Chemical group 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 75
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 71
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 62
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 57
- 208000035475 disorder Diseases 0.000 claims description 57
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 53
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 51
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 47
- 125000001544 thienyl group Chemical class 0.000 claims description 44
- 125000002541 furyl group Chemical group 0.000 claims description 43
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000001153 fluoro group Chemical group F* 0.000 claims description 36
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 35
- 150000001204 N-oxides Chemical class 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 239000012453 solvate Substances 0.000 claims description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
- 239000012429 reaction media Substances 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000001931 aliphatic group Chemical class 0.000 claims description 24
- 238000002156 mixing Methods 0.000 claims description 24
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- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 23
- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
- UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical compound C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- 239000005864 Sulphur Chemical group 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 239000001301 oxygen Chemical group 0.000 claims description 20
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
- 238000011321 prophylaxis Methods 0.000 claims description 18
- 102000018208 Cannabinoid Receptor Human genes 0.000 claims description 16
- 108050007331 Cannabinoid receptor Proteins 0.000 claims description 16
- 229930003827 cannabinoid Natural products 0.000 claims description 15
- 239000003557 cannabinoid Substances 0.000 claims description 15
- 208000011117 substance-related disease Diseases 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 12
- 102000005962 receptors Human genes 0.000 claims description 12
- 108020003175 receptors Proteins 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- BNBGRXOGPFOPLL-QRQCRPRQSA-N n-[(2r,3s)-1-[bis(4-chlorophenyl)methyl]-2-methylazetidin-3-yl]-4-fluorobenzenesulfonamide Chemical compound C([C@@H]([C@H]1C)NS(=O)(=O)C=2C=CC(F)=CC=2)N1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 BNBGRXOGPFOPLL-QRQCRPRQSA-N 0.000 claims description 3
- BNBGRXOGPFOPLL-OYHNWAKOSA-N n-[(2s,3r)-1-[bis(4-chlorophenyl)methyl]-2-methylazetidin-3-yl]-4-fluorobenzenesulfonamide Chemical compound C([C@H]([C@@H]1C)NS(=O)(=O)C=2C=CC(F)=CC=2)N1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 BNBGRXOGPFOPLL-OYHNWAKOSA-N 0.000 claims description 3
- NMZREQPYUSVIIX-MEDUHNTESA-N (2s,3r)-1-[bis(4-chlorophenyl)methyl]-2-methylazetidin-3-amine Chemical compound C[C@H]1[C@H](N)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 NMZREQPYUSVIIX-MEDUHNTESA-N 0.000 claims description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 2
- XODIKZYDMAHSPS-UPCLLVRISA-N 4-acetyl-n-[(2s,3r)-1-[bis(4-chlorophenyl)methyl]-2-methylazetidin-3-yl]benzenesulfonamide Chemical compound C([C@H]([C@@H]1C)NS(=O)(=O)C=2C=CC(=CC=2)C(C)=O)N1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 XODIKZYDMAHSPS-UPCLLVRISA-N 0.000 claims description 2
- LFLSATHZMYYIAQ-UHFFFAOYSA-N 4-flourobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(F)C=C1 LFLSATHZMYYIAQ-UHFFFAOYSA-N 0.000 claims description 2
- WVSYONICNIDYBE-UHFFFAOYSA-N 4-fluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(F)C=C1 WVSYONICNIDYBE-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D409/02—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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
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- 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
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- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200400379A ES2244314B1 (es) | 2004-02-17 | 2004-02-17 | Compuestos azetidinicos sustituidos, su preparacion y su aplicacion como medicamentos. |
| US10/804,558 US20050187208A1 (en) | 2004-02-17 | 2004-03-19 | Substituted Azetidine compounds, their preparation and use as medicaments |
| PCT/EP2005/001658 WO2005077897A1 (en) | 2004-02-17 | 2005-02-16 | Substituted azetidine compounds, their preparation and use as medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1718609A1 true EP1718609A1 (en) | 2006-11-08 |
Family
ID=34863169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05715383A Withdrawn EP1718609A1 (en) | 2004-02-17 | 2005-02-16 | Substituted azetidine compounds, their preparation and use as medicaments |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1718609A1 (pt) |
| JP (1) | JP2007522255A (pt) |
| KR (1) | KR20060124756A (pt) |
| AU (1) | AU2005212835A1 (pt) |
| BR (1) | BRPI0507801A (pt) |
| CA (1) | CA2556565A1 (pt) |
| NO (1) | NO20064078L (pt) |
| RU (1) | RU2006133258A (pt) |
| WO (1) | WO2005077897A1 (pt) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060019587A (ko) | 2003-06-11 | 2006-03-03 | 머크 앤드 캄파니 인코포레이티드 | 치환된 3-알킬 및 3-알케닐 아제티딘 유도체 |
| JP4943826B2 (ja) * | 2005-11-25 | 2012-05-30 | 田辺三菱製薬株式会社 | 医薬組成物 |
| US7906652B2 (en) | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
| AU2007283113A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| FR2928149B1 (fr) * | 2008-02-29 | 2011-01-14 | Sanofi Aventis | Composes derives d'azetidines, leur preparation et leur application en therapeutique |
| UY31968A (es) | 2008-07-09 | 2010-01-29 | Sanofi Aventis | Nuevos derivados heterocíclicos, sus procesos para su preparación, y sus usos terapéuticos |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| FR2946650B1 (fr) * | 2009-06-16 | 2011-08-19 | Sanofi Aventis | Esters derives d'azetidines, leur preparation et leur application en therapeutique. |
| CA2771278A1 (en) | 2009-08-26 | 2011-03-03 | Sanofi | Novel crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US9440948B2 (en) | 2010-09-03 | 2016-09-13 | University Of Florida Research Foundation, Inc. | Nicotine compounds and analogs thereof, synthetic methods of making compounds, and methods of use |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120057A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8809324B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| PL395470A1 (pl) * | 2011-06-29 | 2013-01-07 | Adamed Spólka Z Ograniczona Odpowiedzialnoscia | Sulfonamidowe pochodne amin alicyklicznych do leczenia chorób osrodkowego ukladu nerwowego |
| KR101273566B1 (ko) * | 2011-09-05 | 2013-06-11 | 한국과학기술연구원 | 신규한 아제티딘 유도체 및 이를 함유하는 항우울제 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2649100B1 (fr) * | 1989-06-29 | 1994-03-04 | Laboratorios Dr Esteve Sa | Nouvelles azetidines, leur preparation et leur application comme intermediaires pour la preparation de composes avec activite antimicrobienne |
| FR2805810B1 (fr) * | 2000-03-03 | 2002-04-26 | Aventis Pharma Sa | Compositions pharmaceutiques contenant des derives de 3- amino-azetidine, les nouveaux derives et leur preparation |
| FR2829028B1 (fr) * | 2001-08-29 | 2004-12-17 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et d'un produit qui active la neurotransmission dopaminergique dans le cerveau, les compositions pharmaceutiques les contenant et leur utilisation pour le traitement de la maladie de |
| FR2833842B1 (fr) | 2001-12-21 | 2004-02-13 | Aventis Pharma Sa | Compositions pharmaceutiques a base de derives d'azetidine |
-
2005
- 2005-02-16 RU RU2006133258/04A patent/RU2006133258A/ru unknown
- 2005-02-16 KR KR1020067018702A patent/KR20060124756A/ko not_active Application Discontinuation
- 2005-02-16 EP EP05715383A patent/EP1718609A1/en not_active Withdrawn
- 2005-02-16 CA CA002556565A patent/CA2556565A1/en not_active Abandoned
- 2005-02-16 JP JP2006553539A patent/JP2007522255A/ja not_active Withdrawn
- 2005-02-16 AU AU2005212835A patent/AU2005212835A1/en not_active Abandoned
- 2005-02-16 WO PCT/EP2005/001658 patent/WO2005077897A1/en active Application Filing
- 2005-02-16 BR BRPI0507801-6A patent/BRPI0507801A/pt not_active Application Discontinuation
-
2006
- 2006-09-11 NO NO20064078A patent/NO20064078L/no not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2005077897A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007522255A (ja) | 2007-08-09 |
| CA2556565A1 (en) | 2005-08-25 |
| KR20060124756A (ko) | 2006-12-05 |
| BRPI0507801A (pt) | 2007-07-10 |
| WO2005077897A1 (en) | 2005-08-25 |
| RU2006133258A (ru) | 2008-04-10 |
| AU2005212835A1 (en) | 2005-08-25 |
| NO20064078L (no) | 2006-09-11 |
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