CA2751481C - Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique - Google Patents
Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique Download PDFInfo
- Publication number
- CA2751481C CA2751481C CA2751481A CA2751481A CA2751481C CA 2751481 C CA2751481 C CA 2751481C CA 2751481 A CA2751481 A CA 2751481A CA 2751481 A CA2751481 A CA 2751481A CA 2751481 C CA2751481 C CA 2751481C
- Authority
- CA
- Canada
- Prior art keywords
- spiro
- aza
- ylmethyl
- group
- isoxazol
- 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.)
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- 238000002360 preparation method Methods 0.000 title claims description 11
- 230000001225 therapeutic effect Effects 0.000 title abstract description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 239000002253 acid Substances 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 18
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011737 fluorine Chemical group 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- -1 -CH2CN Chemical group 0.000 claims description 109
- 238000000034 method Methods 0.000 claims description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 230000007170 pathology Effects 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
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- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 4
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 238000006254 arylation reaction Methods 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 3
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- HEAHLTGDUHXTTO-UHFFFAOYSA-N 1,3-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCNC1 HEAHLTGDUHXTTO-UHFFFAOYSA-N 0.000 claims description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 2
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 claims description 2
- 208000019693 Lung disease Diseases 0.000 claims description 2
- 206010028813 Nausea Diseases 0.000 claims description 2
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- 206010063897 Renal ischaemia Diseases 0.000 claims description 2
- 206010046543 Urinary incontinence Diseases 0.000 claims description 2
- 208000012886 Vertigo Diseases 0.000 claims description 2
- 206010047700 Vomiting Diseases 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
- ZETANZUWYPHWDA-UHFFFAOYSA-N azetidine;pyrrolidine Chemical compound C1CNC1.C1CCNC1 ZETANZUWYPHWDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 2
- 210000000987 immune system Anatomy 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
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- TVQOEGVBMRCMFR-UHFFFAOYSA-N thiadiazinane Chemical compound C1CNNSC1 TVQOEGVBMRCMFR-UHFFFAOYSA-N 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
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- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- UVHOGDOUCQFVSB-UHFFFAOYSA-N [7-[4-(trifluoromethyl)pyridin-2-yl]-7-azaspiro[3.5]nonan-2-yl]carbamic acid Chemical compound C1C(NC(=O)O)CC21CCN(C=1N=CC=C(C=1)C(F)(F)F)CC2 UVHOGDOUCQFVSB-UHFFFAOYSA-N 0.000 claims 1
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0900493A FR2941696B1 (fr) | 2009-02-05 | 2009-02-05 | Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique |
| FR0900493 | 2009-02-05 | ||
| PCT/FR2010/050183 WO2010089510A2 (fr) | 2009-02-05 | 2010-02-04 | Dérivés d'azaspiranyl-alkylcarbamates d'hétérocycles à 5 chaînons, leur préparation et leur application en thérapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2751481A1 CA2751481A1 (fr) | 2010-08-12 |
| CA2751481C true CA2751481C (fr) | 2017-05-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2751481A Expired - Fee Related CA2751481C (fr) | 2009-02-05 | 2010-02-04 | Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique |
Country Status (20)
| Country | Link |
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| US (1) | US8889702B2 (https=) |
| EP (1) | EP2393809B1 (https=) |
| JP (1) | JP5586632B2 (https=) |
| KR (1) | KR20110117215A (https=) |
| CN (1) | CN102369200B (https=) |
| AR (1) | AR075247A1 (https=) |
| AU (1) | AU2010212235B2 (https=) |
| BR (1) | BRPI1007456A2 (https=) |
| CA (1) | CA2751481C (https=) |
| CO (1) | CO6362007A2 (https=) |
| EA (1) | EA201171000A1 (https=) |
| FR (1) | FR2941696B1 (https=) |
| IL (1) | IL214390A0 (https=) |
| MA (1) | MA33104B1 (https=) |
| MX (1) | MX2011008308A (https=) |
| SG (1) | SG173557A1 (https=) |
| TN (1) | TN2011000331A1 (https=) |
| TW (1) | TW201039823A (https=) |
| UY (1) | UY32423A (https=) |
| WO (1) | WO2010089510A2 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2011085216A2 (en) | 2010-01-08 | 2011-07-14 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors for treating parkinson's disease and restless legs syndrome |
| US20130224151A1 (en) | 2010-03-31 | 2013-08-29 | United States Of America | Use of FAAH Inhibitors for Treating Abdominal, Visceral and Pelvic Pain |
| US9822129B2 (en) | 2012-03-02 | 2017-11-21 | Genentech, Inc. | Amido spirocyclic amide and sulfonamide derivatives |
| JP6099753B2 (ja) * | 2012-10-03 | 2017-03-22 | アドビナス セラピューティクス リミテッド | スピロ環化合物、その組成物及びその医薬応用 |
| JO3517B1 (ar) | 2014-01-17 | 2020-07-05 | Novartis Ag | ان-ازاسبيرو الكان حلقي كبديل مركبات اريل-ان مغايرة وتركيبات لتثبيط نشاط shp2 |
| WO2015107494A1 (en) | 2014-01-17 | 2015-07-23 | Novartis Ag | 1 -(triazin-3-yi_/pyridazin-3-yl)-piper(-azine)idine derivatives and compositions thereof for inhibiting the activity of shp2 |
| ES2699351T3 (es) | 2014-01-17 | 2019-02-08 | Novartis Ag | Derivados de 1-piridazin/triazin-3-il-piper(-azina)/idina/pirolidina y composiciones de las mismas para inhibir la actividad de SHP2 |
| EP3310779B1 (en) | 2015-06-19 | 2019-05-08 | Novartis AG | Compounds and compositions for inhibiting the activity of shp2 |
| WO2016203405A1 (en) | 2015-06-19 | 2016-12-22 | Novartis Ag | Compounds and compositions for inhibiting the activity of shp2 |
| US10287266B2 (en) | 2015-06-19 | 2019-05-14 | Novartis Ag | Compounds and compositions for inhibiting the activity of SHP2 |
| WO2017160925A1 (en) * | 2016-03-16 | 2017-09-21 | Kalyra Pharmaceuticals, Inc. | Analgesic compounds |
| WO2017216706A1 (en) | 2016-06-14 | 2017-12-21 | Novartis Ag | Compounds and compositions for inhibiting the activity of shp2 |
| JOP20190107A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| CA3048340A1 (en) | 2017-01-10 | 2018-07-19 | Novartis Ag | Pharmaceutical combination comprising an alk inhibitor and a shp2 inhibitor |
| EP4335848A3 (en) | 2017-03-13 | 2024-06-19 | Lundbeck La Jolla Research Center, Inc. | Dual magl and faah inhibitors |
| JP7257387B2 (ja) | 2017-08-29 | 2023-04-13 | ハー・ルンドベック・アクチエゼルスカベット | スピロ環化合物並びにその作製及び使用方法 |
| CN116574105B (zh) * | 2018-09-27 | 2025-10-10 | 深圳微芯生物科技股份有限公司 | 具有吲哚胺-2,3-双加氧酶抑制活性的喹啉衍生物 |
| KR20250005229A (ko) | 2022-05-04 | 2025-01-09 | 하. 룬드벡 아크티에셀스카브 | 모노아실글리세롤 리파제 억제제로서 1,1,1,3,3,3-헥사플루오로프로판-2-일 (s)-1-(피리다진-3-일카르바모일)-6 아자스피로[2.5]옥탄-6-카르복실레이트의 결정질 형태 |
Family Cites Families (16)
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| JPH0678335B2 (ja) | 1991-06-19 | 1994-10-05 | ファイザー・インコーポレーテッド | アザスピロキノロン化合物、その製法および抗菌組成物 |
| US6518423B1 (en) | 1996-08-09 | 2003-02-11 | Eisai Co., Ltd. | Benzopiperidine derivatives |
| AU755361B2 (en) | 1998-02-19 | 2002-12-12 | Eisai R&D Management Co., Ltd. | Phthalazine derivatives and remedies for erectile dysfunction |
| FR2816938B1 (fr) | 2000-11-22 | 2003-01-03 | Sanofi Synthelabo | Derives de 3-aroylindole, leur procede de preparation et les compositions pharmaceutiques en contenant |
| JP2003246780A (ja) | 2001-12-17 | 2003-09-02 | Eisai Co Ltd | 含窒素芳香環化合物の製造方法 |
| US6995144B2 (en) | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
| FR2843964B1 (fr) * | 2002-08-29 | 2004-10-01 | Sanofi Synthelabo | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
| EA010267B1 (ru) * | 2002-10-07 | 2008-06-30 | Те Риджентс Оф Те Юниверсити Оф Калифорния | Модуляция тревоги через блокаду гидролиза анандамида |
| FR2854633B1 (fr) * | 2003-05-07 | 2005-06-24 | Sanofi Synthelabo | Derives de piperidinyl-et piperazinyl-alkylcarbamates, leur preparation et leur application en therapeutique |
| FR2866885B1 (fr) * | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives de piperidinylalkylcarbamates, leur prepation et leur application en therapeutique |
| FR2885364B1 (fr) * | 2005-05-03 | 2007-06-29 | Sanofi Aventis Sa | Derives d'alkyl-, alkenyl-et alkynylcarbamates, leur preparation et leur application en therapeutique |
| WO2008013834A1 (en) | 2006-07-24 | 2008-01-31 | Gilead Sciences, Inc., | Bisfuranyl protease inhibitors |
| TW200831080A (en) * | 2006-12-15 | 2008-08-01 | Irm Llc | Compounds and compositions as inhibitors of cannabinoid receptor 1 activity |
| WO2008124085A2 (en) | 2007-04-03 | 2008-10-16 | Exelixis, Inc. | Methods of using combinations of mek and jak-2 inhibitors |
| FR2934265B1 (fr) * | 2008-07-23 | 2010-07-30 | Sanofi Aventis | Derives de carbamates d'alkylthiazoles, leur preparation et leur application en therapeutique |
| US20100113465A1 (en) * | 2008-10-30 | 2010-05-06 | Pfizer Inc. | 7-azaspiro[3.5]nonane-7-carboxamide compounds |
-
2009
- 2009-02-05 FR FR0900493A patent/FR2941696B1/fr not_active Expired - Fee Related
-
2010
- 2010-02-04 US US13/145,926 patent/US8889702B2/en not_active Expired - Fee Related
- 2010-02-04 CN CN201080014506.8A patent/CN102369200B/zh not_active Expired - Fee Related
- 2010-02-04 MA MA34149A patent/MA33104B1/fr unknown
- 2010-02-04 EA EA201171000A patent/EA201171000A1/ru unknown
- 2010-02-04 KR KR1020117020496A patent/KR20110117215A/ko not_active Withdrawn
- 2010-02-04 JP JP2011548754A patent/JP5586632B2/ja not_active Expired - Fee Related
- 2010-02-04 MX MX2011008308A patent/MX2011008308A/es unknown
- 2010-02-04 SG SG2011056462A patent/SG173557A1/en unknown
- 2010-02-04 AU AU2010212235A patent/AU2010212235B2/en not_active Ceased
- 2010-02-04 EP EP10708283.6A patent/EP2393809B1/fr active Active
- 2010-02-04 BR BRPI1007456-2A patent/BRPI1007456A2/pt not_active IP Right Cessation
- 2010-02-04 WO PCT/FR2010/050183 patent/WO2010089510A2/fr not_active Ceased
- 2010-02-04 CA CA2751481A patent/CA2751481C/fr not_active Expired - Fee Related
- 2010-02-05 TW TW099103578A patent/TW201039823A/zh unknown
- 2010-02-05 UY UY0001032423A patent/UY32423A/es not_active Application Discontinuation
- 2010-02-05 AR ARP100100315A patent/AR075247A1/es not_active Application Discontinuation
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2011
- 2011-07-05 TN TN2011000331A patent/TN2011000331A1/fr unknown
- 2011-08-01 IL IL214390A patent/IL214390A0/en unknown
- 2011-08-05 CO CO11099134A patent/CO6362007A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110117215A (ko) | 2011-10-26 |
| US8889702B2 (en) | 2014-11-18 |
| AU2010212235B2 (en) | 2016-06-09 |
| SG173557A1 (en) | 2011-09-29 |
| CA2751481A1 (fr) | 2010-08-12 |
| JP2012516881A (ja) | 2012-07-26 |
| WO2010089510A2 (fr) | 2010-08-12 |
| CN102369200A (zh) | 2012-03-07 |
| EP2393809A2 (fr) | 2011-12-14 |
| FR2941696B1 (fr) | 2011-04-15 |
| UY32423A (es) | 2010-09-30 |
| CN102369200B (zh) | 2015-05-20 |
| TN2011000331A1 (fr) | 2013-03-27 |
| CO6362007A2 (es) | 2012-01-20 |
| BRPI1007456A2 (pt) | 2019-04-16 |
| US20110319381A1 (en) | 2011-12-29 |
| WO2010089510A3 (fr) | 2010-09-30 |
| JP5586632B2 (ja) | 2014-09-10 |
| EP2393809B1 (fr) | 2014-04-30 |
| AU2010212235A1 (en) | 2011-08-25 |
| IL214390A0 (en) | 2011-09-27 |
| MX2011008308A (es) | 2011-11-02 |
| AR075247A1 (es) | 2011-03-16 |
| EA201171000A1 (ru) | 2012-02-28 |
| FR2941696A1 (fr) | 2010-08-06 |
| TW201039823A (en) | 2010-11-16 |
| MA33104B1 (fr) | 2012-03-01 |
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| MKLA | Lapsed |
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