DK2721012T3 - Biclo (3.1.0) hexane-2,6-dicarboxylic acid derivatives as MGLU2 receptor agonist - Google Patents
Biclo (3.1.0) hexane-2,6-dicarboxylic acid derivatives as MGLU2 receptor agonist Download PDFInfo
- Publication number
- DK2721012T3 DK2721012T3 DK12729769.5T DK12729769T DK2721012T3 DK 2721012 T3 DK2721012 T3 DK 2721012T3 DK 12729769 T DK12729769 T DK 12729769T DK 2721012 T3 DK2721012 T3 DK 2721012T3
- Authority
- DK
- Denmark
- Prior art keywords
- hydrogen
- optionally substituted
- pharmaceutically acceptable
- fluorine atoms
- hexane
- Prior art date
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 238000011813 knockout mouse model Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000003938 response to stress Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- JLEXUIVKURIPFI-UHFFFAOYSA-N tris phosphate Chemical compound OP(O)(O)=O.OCC(N)(CO)CO JLEXUIVKURIPFI-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- 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
- A61K31/4196—1,2,4-Triazoles
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11382208 | 2011-06-17 | ||
| US201161522791P | 2011-08-12 | 2011-08-12 | |
| PCT/US2012/041229 WO2012173850A1 (en) | 2011-06-17 | 2012-06-07 | Bicyclo (3.1.0) hexane- 2, 6 -dicarboxylic acid derivatives as mglu2 receptor agonist |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2721012T3 true DK2721012T3 (en) | 2016-08-15 |
Family
ID=47357416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK12729769.5T DK2721012T3 (en) | 2011-06-17 | 2012-06-07 | Biclo (3.1.0) hexane-2,6-dicarboxylic acid derivatives as MGLU2 receptor agonist |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US9296710B2 (OSRAM) |
| EP (1) | EP2721012B1 (OSRAM) |
| JP (1) | JP5945592B2 (OSRAM) |
| KR (1) | KR101598679B1 (OSRAM) |
| CN (1) | CN103596933B (OSRAM) |
| AU (1) | AU2012271024B2 (OSRAM) |
| BR (1) | BR112013031928B1 (OSRAM) |
| CA (1) | CA2836485C (OSRAM) |
| CY (1) | CY1117682T1 (OSRAM) |
| DK (1) | DK2721012T3 (OSRAM) |
| EA (1) | EA023553B1 (OSRAM) |
| ES (1) | ES2587204T3 (OSRAM) |
| HR (1) | HRP20160676T1 (OSRAM) |
| HU (1) | HUE030171T2 (OSRAM) |
| MX (1) | MX2013014802A (OSRAM) |
| PL (1) | PL2721012T3 (OSRAM) |
| PT (1) | PT2721012T (OSRAM) |
| RS (1) | RS54888B1 (OSRAM) |
| SI (1) | SI2721012T1 (OSRAM) |
| WO (1) | WO2012173850A1 (OSRAM) |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993006127A1 (en) | 1991-09-17 | 1993-04-01 | Warner-Lambert Company | Novel amino acid prodrug renin inhibitors |
| US5576323A (en) | 1993-12-03 | 1996-11-19 | Eli Lilly And Company | Excitatory amino acid receptor antagonists |
| US5849525A (en) | 1994-03-09 | 1998-12-15 | Brigham And Women's Hospital, Inc. | Compositions corresponding to a proton-coupled peptide transporter and methods of making and using same |
| US5688826A (en) | 1995-11-16 | 1997-11-18 | Eli Lilly And Company | Excitatory amino acid derivatives |
| GB9605429D0 (en) | 1995-11-16 | 1996-05-15 | Lilly Co Eli | Excitatory amino acid receptor antagonists |
| IL124487A (en) | 1995-11-16 | 2001-01-11 | Lilly Co Eli | Excitatory amino acid derivatives, their preparation and pharmaceutical compositions containing them |
| US5952294A (en) | 1996-07-31 | 1999-09-14 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Peptidyl prodrugs and methods of making and using the same |
| ZA983930B (en) | 1997-05-14 | 1999-11-08 | Lilly Co Eli | Excitatory amino acid receptor modulators. |
| CA2318800C (en) | 1998-01-28 | 2005-12-20 | Taisho Pharmaceutical Co., Ltd. | Fluorine-containing amino acid derivatives |
| PT1110943E (pt) | 1998-08-31 | 2004-08-31 | Taisho Pharmaceutical Co Ltd | Derivados 6-fluorobiciclo¬3.1.0|hexano |
| US6716452B1 (en) | 2000-08-22 | 2004-04-06 | New River Pharmaceuticals Inc. | Active agent delivery systems and methods for protecting and administering active agents |
| CN1216038C (zh) | 2000-06-28 | 2005-08-24 | 大正制药株式会社 | 新型二羧酸衍生物 |
| US7038077B2 (en) | 2001-01-11 | 2006-05-02 | Eli Lilly And Company | Prodrugs of excitatory amino acids |
| US7256217B2 (en) | 2001-01-11 | 2007-08-14 | Eli Lilly And Company | Prodrugs of excitatory amino acids |
| EP1370519A1 (en) * | 2001-02-22 | 2003-12-17 | Eli Lilly And Company | Synthetic excitatory amino acids |
| CA2450167A1 (en) | 2001-06-12 | 2002-12-19 | Elan Pharmaceuticals, Inc. | Macrocycles useful in the treatment of alzheimer's disease |
| MXPA04006322A (es) | 2001-12-27 | 2004-10-04 | Taisho Pharmaceutical Co Ltd | Derivados de 6-fluorobiciclo[3.1.0]hexano. |
| US20050192273A1 (en) | 2002-04-03 | 2005-09-01 | Johnson Bryan G. | Therapy for psychoses combining an atypical antipsychotic and an mglu2/3 receptor agonist |
| CA2478227A1 (en) | 2002-04-03 | 2003-10-16 | Eli Lilly And Company | Therapy for psychoses combining an atypical antipsychotic and an mglu2/3 receptor agonist |
| ATE421526T1 (de) | 2002-06-11 | 2009-02-15 | Lilly Co Eli | Prodrugs von exzitatorischen aminosäuren |
| CN100482680C (zh) * | 2002-06-11 | 2009-04-29 | 伊莱利利公司 | 兴奋性氨基酸前药 |
| CN100582087C (zh) * | 2003-06-26 | 2010-01-20 | 大正制药株式会社 | 2-氨基-双环[3.1.0]己烷-2,6-二甲酸酯衍生物 |
| US7381746B2 (en) * | 2003-06-26 | 2008-06-03 | Taisho Pharmaceutical Co., Ltd. | 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivative |
| EA020506B1 (ru) * | 2009-11-18 | 2014-11-28 | Сувен Лайф Сайенсиз Лимитед | БИЦИКЛИЧЕСКИЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ЛИГАНДОВ αβНИКОТИНОВОГО АЦЕТИЛХОЛИНОВОГО РЕЦЕПТОРА |
| AR079343A1 (es) * | 2009-12-21 | 2012-01-18 | Lilly Co Eli | Compuesto de acido 2-amino-4-(4h-1,2,4-triazol-3-ilsulfanil)biciclo[3.1.0]hexano-2,6-dicarboxilico, composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para tratar un trastorno psiquiatrico |
-
2012
- 2012-06-07 CA CA2836485A patent/CA2836485C/en active Active
- 2012-06-07 CN CN201280029080.2A patent/CN103596933B/zh active Active
- 2012-06-07 BR BR112013031928-3A patent/BR112013031928B1/pt active IP Right Grant
- 2012-06-07 MX MX2013014802A patent/MX2013014802A/es active IP Right Grant
- 2012-06-07 PL PL12729769T patent/PL2721012T3/pl unknown
- 2012-06-07 KR KR1020137033028A patent/KR101598679B1/ko active Active
- 2012-06-07 EP EP12729769.5A patent/EP2721012B1/en active Active
- 2012-06-07 HU HUE12729769A patent/HUE030171T2/en unknown
- 2012-06-07 JP JP2014515878A patent/JP5945592B2/ja active Active
- 2012-06-07 EA EA201391700A patent/EA023553B1/ru not_active IP Right Cessation
- 2012-06-07 HR HRP20160676TT patent/HRP20160676T1/hr unknown
- 2012-06-07 AU AU2012271024A patent/AU2012271024B2/en active Active
- 2012-06-07 DK DK12729769.5T patent/DK2721012T3/en active
- 2012-06-07 RS RS20160491A patent/RS54888B1/sr unknown
- 2012-06-07 PT PT127297695T patent/PT2721012T/pt unknown
- 2012-06-07 WO PCT/US2012/041229 patent/WO2012173850A1/en not_active Ceased
- 2012-06-07 US US14/123,768 patent/US9296710B2/en active Active
- 2012-06-07 ES ES12729769.5T patent/ES2587204T3/es active Active
- 2012-06-07 SI SI201230569A patent/SI2721012T1/sl unknown
-
2016
- 2016-06-24 CY CY20161100570T patent/CY1117682T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2012271024B2 (en) | 2015-07-09 |
| CA2836485A1 (en) | 2012-12-20 |
| US20140113944A1 (en) | 2014-04-24 |
| SI2721012T1 (sl) | 2016-08-31 |
| PL2721012T3 (pl) | 2017-05-31 |
| PT2721012T (pt) | 2016-07-27 |
| HRP20160676T1 (hr) | 2016-07-15 |
| WO2012173850A1 (en) | 2012-12-20 |
| CN103596933A (zh) | 2014-02-19 |
| US9296710B2 (en) | 2016-03-29 |
| BR112013031928B1 (pt) | 2022-05-24 |
| MX2013014802A (es) | 2014-01-24 |
| CA2836485C (en) | 2016-12-13 |
| CY1117682T1 (el) | 2017-05-17 |
| JP5945592B2 (ja) | 2016-07-05 |
| HUE030171T2 (en) | 2017-05-29 |
| CN103596933B (zh) | 2016-03-23 |
| ES2587204T3 (es) | 2016-10-21 |
| AU2012271024A1 (en) | 2013-11-21 |
| RS54888B1 (sr) | 2016-10-31 |
| EP2721012B1 (en) | 2016-05-25 |
| BR112013031928A2 (pt) | 2016-12-13 |
| JP2014517035A (ja) | 2014-07-17 |
| EP2721012A1 (en) | 2014-04-23 |
| EA201391700A1 (ru) | 2014-04-30 |
| KR101598679B1 (ko) | 2016-02-29 |
| KR20140009568A (ko) | 2014-01-22 |
| EA023553B1 (ru) | 2016-06-30 |
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