AU2003226977A1 - Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, the production thereof and their use in medicaments - Google Patents
Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, the production thereof and their use in medicaments Download PDFInfo
- Publication number
- AU2003226977A1 AU2003226977A1 AU2003226977A AU2003226977A AU2003226977A1 AU 2003226977 A1 AU2003226977 A1 AU 2003226977A1 AU 2003226977 A AU2003226977 A AU 2003226977A AU 2003226977 A AU2003226977 A AU 2003226977A AU 2003226977 A1 AU2003226977 A1 AU 2003226977A1
- Authority
- AU
- Australia
- Prior art keywords
- formula
- alkyl
- phenyl
- compound
- oxadiazol
- 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.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- -1 chlorophenoxy Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000002431 hydrogen Chemical class 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 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 3
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- 238000007385 chemical modification Methods 0.000 claims description 2
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- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
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- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
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- 101000598778 Homo sapiens Protein OSCP1 Proteins 0.000 claims 1
- 101001067395 Mus musculus Phospholipid scramblase 1 Proteins 0.000 claims 1
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- DAQCUXYFZBBWOG-UHFFFAOYSA-N 5-dodecoxy-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 DAQCUXYFZBBWOG-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 125000004104 aryloxy group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
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- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- WWQYTEPUEUNBOM-SANMLTNESA-N (2,5-dioxopyrrolidin-1-yl) (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-(1h-indol-3-yl)propanoate Chemical compound O=C([C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)ON1C(=O)CCC1=O WWQYTEPUEUNBOM-SANMLTNESA-N 0.000 description 1
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- JSMHDBKKRKIODL-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-5-dodecoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=C(Cl)C(Cl)=C1 JSMHDBKKRKIODL-UHFFFAOYSA-N 0.000 description 1
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- FCHJQWWCWWMWIO-UHFFFAOYSA-N 5-(2-dodecoxyethoxy)-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCOCCCCCCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 FCHJQWWCWWMWIO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
- A61K31/4245—Oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (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)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10208987A DE10208987A1 (de) | 2002-02-28 | 2002-02-28 | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxidiazol-2-one, ihre Herstellung und Verwendung in Arzneistoffen |
| DE10208987.6 | 2002-02-28 | ||
| PCT/EP2003/001484 WO2003072555A1 (de) | 2002-02-28 | 2003-02-14 | Substituierte 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-one sowie ihre herstellung und verwendung in arzneistoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2003226977A1 true AU2003226977A1 (en) | 2003-09-09 |
Family
ID=27740558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003226977A Abandoned AU2003226977A1 (en) | 2002-02-28 | 2003-02-14 | Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, the production thereof and their use in medicaments |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1480960B1 (enExample) |
| JP (1) | JP4486363B2 (enExample) |
| KR (1) | KR20040095240A (enExample) |
| CN (1) | CN1639137A (enExample) |
| AR (1) | AR038701A1 (enExample) |
| AT (1) | ATE557012T1 (enExample) |
| AU (1) | AU2003226977A1 (enExample) |
| BR (1) | BR0307921A (enExample) |
| CA (1) | CA2477031A1 (enExample) |
| CO (1) | CO5611146A2 (enExample) |
| DE (1) | DE10208987A1 (enExample) |
| HR (1) | HRP20040782A2 (enExample) |
| HU (1) | HUP0402671A3 (enExample) |
| IL (1) | IL163683A0 (enExample) |
| MA (1) | MA27172A1 (enExample) |
| MX (1) | MXPA04007960A (enExample) |
| NO (1) | NO20044090L (enExample) |
| PE (1) | PE20030928A1 (enExample) |
| PL (1) | PL370423A1 (enExample) |
| RU (1) | RU2004128933A (enExample) |
| TW (1) | TW200400951A (enExample) |
| WO (1) | WO2003072555A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7074822B2 (en) | 2004-02-23 | 2006-07-11 | Solvay Pharmaceuticals Gmbh | Alkyl carbamate-substituted β-lactones, process for their preparation, and pharmaceutical compositions containing them |
| CA2585175A1 (en) | 2004-10-25 | 2006-05-04 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising cb1 cannabinoid receptor antagonists and potassium channel openers for the treatment of diabetes mellitus type i, obesity and related conditions |
| CA2710743A1 (en) * | 2007-12-27 | 2009-07-09 | Bial-Portela & Ca., S.A. | 5-o-substituted 3-n-phenyl-1,3,4-oxadiazolones for medical use |
| TW201028406A (en) | 2008-12-23 | 2010-08-01 | Bial Portela & Ca Sa | 5-O-substituted 3-N-aryl-1,3,4-oxadiazolones for medical use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19942354A1 (de) * | 1999-09-04 | 2001-03-08 | Aventis Pharma Gmbh | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one, ihre Herstellung und Verwendung in Arzneimitteln |
| WO2001066531A1 (de) * | 2000-03-07 | 2001-09-13 | Aventis Pharma Deutschland Gmbh | Substituierte 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one (und) ihre verwendung zur hemmung der hormonsensitiven lipase |
-
2002
- 2002-02-28 DE DE10208987A patent/DE10208987A1/de not_active Withdrawn
-
2003
- 2003-02-05 PE PE2003000134A patent/PE20030928A1/es not_active Application Discontinuation
- 2003-02-14 AT AT03742936T patent/ATE557012T1/de active
- 2003-02-14 CN CNA038047837A patent/CN1639137A/zh active Pending
- 2003-02-14 AU AU2003226977A patent/AU2003226977A1/en not_active Abandoned
- 2003-02-14 HU HU0402671A patent/HUP0402671A3/hu unknown
- 2003-02-14 JP JP2003571261A patent/JP4486363B2/ja not_active Expired - Fee Related
- 2003-02-14 MX MXPA04007960A patent/MXPA04007960A/es unknown
- 2003-02-14 KR KR10-2004-7013485A patent/KR20040095240A/ko not_active Withdrawn
- 2003-02-14 EP EP03742936A patent/EP1480960B1/de not_active Expired - Lifetime
- 2003-02-14 PL PL03370423A patent/PL370423A1/xx not_active Application Discontinuation
- 2003-02-14 WO PCT/EP2003/001484 patent/WO2003072555A1/de not_active Ceased
- 2003-02-14 HR HR20040782A patent/HRP20040782A2/hr not_active Application Discontinuation
- 2003-02-14 IL IL16368303A patent/IL163683A0/xx unknown
- 2003-02-14 CA CA002477031A patent/CA2477031A1/en not_active Abandoned
- 2003-02-14 BR BR0307921-0A patent/BR0307921A/pt not_active Application Discontinuation
- 2003-02-14 RU RU2004128933/04A patent/RU2004128933A/ru not_active Application Discontinuation
- 2003-02-26 TW TW092103969A patent/TW200400951A/zh unknown
- 2003-02-26 AR ARP030100624A patent/AR038701A1/es unknown
-
2004
- 2004-07-27 MA MA27803A patent/MA27172A1/fr unknown
- 2004-08-26 CO CO04083779A patent/CO5611146A2/es not_active Application Discontinuation
- 2004-09-27 NO NO20044090A patent/NO20044090L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HRP20040782A2 (en) | 2005-02-28 |
| NO20044090L (no) | 2004-11-04 |
| PE20030928A1 (es) | 2003-12-17 |
| EP1480960B1 (de) | 2012-05-09 |
| EP1480960A1 (de) | 2004-12-01 |
| AR038701A1 (es) | 2005-01-26 |
| JP4486363B2 (ja) | 2010-06-23 |
| CO5611146A2 (es) | 2006-02-28 |
| KR20040095240A (ko) | 2004-11-12 |
| MA27172A1 (fr) | 2005-01-03 |
| CN1639137A (zh) | 2005-07-13 |
| RU2004128933A (ru) | 2005-04-20 |
| BR0307921A (pt) | 2004-12-21 |
| MXPA04007960A (es) | 2004-11-26 |
| ATE557012T1 (de) | 2012-05-15 |
| TW200400951A (en) | 2004-01-16 |
| IL163683A0 (en) | 2005-12-18 |
| HUP0402671A2 (hu) | 2005-04-28 |
| WO2003072555A1 (de) | 2003-09-04 |
| CA2477031A1 (en) | 2003-09-04 |
| DE10208987A1 (de) | 2003-09-11 |
| JP2005519085A (ja) | 2005-06-30 |
| HUP0402671A3 (en) | 2006-07-28 |
| PL370423A1 (en) | 2005-05-30 |
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| Date | Code | Title | Description |
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| PC1 | Assignment before grant (sect. 113) |
Owner name: SANOFI-AVENTIS DEUTSCHLAND GMBH Free format text: FORMER APPLICANT(S): AVENTIS PHARMA DEUTSCHLAND GMBH |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |