JP2014510747A5 - - Google Patents
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- Publication number
- JP2014510747A5 JP2014510747A5 JP2014501751A JP2014501751A JP2014510747A5 JP 2014510747 A5 JP2014510747 A5 JP 2014510747A5 JP 2014501751 A JP2014501751 A JP 2014501751A JP 2014501751 A JP2014501751 A JP 2014501751A JP 2014510747 A5 JP2014510747 A5 JP 2014510747A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- fluoro
- pharmaceutically acceptable
- cyano
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 239000001257 hydrogen Substances 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000001153 fluoro group Chemical group F* 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
- 150000001602 bicycloalkyls Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 4
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 2
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 2
- ZGSNZVRXASCXRP-UHFFFAOYSA-N 5-methoxy-1h-pyrazole Chemical compound COC=1C=CNN=1 ZGSNZVRXASCXRP-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- USQJUMKNJWUXHW-UHFFFAOYSA-N [1]benzofuro[3,2-c]pyridine Chemical compound C1=NC=C2C3=CC=CC=C3OC2=C1 USQJUMKNJWUXHW-UHFFFAOYSA-N 0.000 claims 2
- 125000001118 alkylidene group Chemical group 0.000 claims 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- -1 2- {2- [2- (bicyclo [1.1.1] pent-1-yl) -4-chlorophenoxy ] Ethyl} -7- (4-methyl-1H-imidazol-1-yl) -3,4-dihydro-2H-pyrido [1,2-a] pyrazine-1,6-dione Compound Chemical class 0.000 claims 1
- IVDMVAFKQDDZGH-AWEZNQCLSA-N 2-[(2s)-1-[4-chloro-2-(trifluoromethyl)phenoxy]propan-2-yl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C([C@H](C)N1C(C=2N(C(C(N3C=C(C)N=C3)=CC=2)=O)CC1)=O)OC1=CC=C(Cl)C=C1C(F)(F)F IVDMVAFKQDDZGH-AWEZNQCLSA-N 0.000 claims 1
- CZEVSRPJHTVIAG-AWEZNQCLSA-N 2-[(2s)-1-[4-fluoro-2-(trifluoromethyl)phenoxy]propan-2-yl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C([C@H](C)N1C(C=2N(C(C(N3C=C(C)N=C3)=CC=2)=O)CC1)=O)OC1=CC=C(F)C=C1C(F)(F)F CZEVSRPJHTVIAG-AWEZNQCLSA-N 0.000 claims 1
- WNKIZPPVGKAWKE-UHFFFAOYSA-N 2-[2-[(2,2-difluoro-1,3-benzodioxol-4-yl)oxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C=3OC(F)(F)OC=3C=CC=1)C2=O WNKIZPPVGKAWKE-UHFFFAOYSA-N 0.000 claims 1
- LEHPUPBPVUBARN-UHFFFAOYSA-N 2-[2-[(2,2-difluoro-1,3-dihydroinden-4-yl)oxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C=3CC(F)(F)CC=3C=CC=1)C2=O LEHPUPBPVUBARN-UHFFFAOYSA-N 0.000 claims 1
- HTPYICLKDABRCS-UHFFFAOYSA-N 2-[2-[2-(3,3-difluorocyclobutyl)-4-fluorophenoxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC(F)=CC=1)C1CC(F)(F)C1)C2=O HTPYICLKDABRCS-UHFFFAOYSA-N 0.000 claims 1
- WOARPCISPWAXFG-UHFFFAOYSA-N 2-[2-[2-(3-bicyclo[1.1.1]pentanyl)phenoxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC=CC=1)C13CC(C1)C3)C2=O WOARPCISPWAXFG-UHFFFAOYSA-N 0.000 claims 1
- XNTCGZXHDJPICB-UHFFFAOYSA-N 2-[2-[4-fluoro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenoxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC(F)=CC=1)C(C)(C)C(F)(F)F)C2=O XNTCGZXHDJPICB-UHFFFAOYSA-N 0.000 claims 1
- YQSXKNVPEQLXJQ-UHFFFAOYSA-N 2-[2-[[4-fluoro-2-(trifluoromethyl)-1,3-benzothiazol-7-yl]oxy]ethyl]-7-(4-methylimidazol-1-yl)-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C=3SC(=NC=3C(F)=CC=1)C(F)(F)F)C2=O YQSXKNVPEQLXJQ-UHFFFAOYSA-N 0.000 claims 1
- AHERSACVYXVWEK-UHFFFAOYSA-N 7-(4-methylimidazol-1-yl)-2-[2-[2-[2-(trifluoromethyl)-1,3-thiazol-4-yl]phenoxy]ethyl]-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC=CC=1)C=1N=C(SC=1)C(F)(F)F)C2=O AHERSACVYXVWEK-UHFFFAOYSA-N 0.000 claims 1
- XNBWJMQONCSXNL-UHFFFAOYSA-N 7-(4-methylimidazol-1-yl)-2-[2-[2-[3-(trifluoromethyl)-1,2,4-thiadiazol-5-yl]phenoxy]ethyl]-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC=CC=1)C=1SN=C(N=1)C(F)(F)F)C2=O XNBWJMQONCSXNL-UHFFFAOYSA-N 0.000 claims 1
- WANTWYYPVUJSRC-UHFFFAOYSA-N 7-(4-methylimidazol-1-yl)-2-[2-[2-[3-(trifluoromethyl)-1,2-oxazol-5-yl]phenoxy]ethyl]-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C(=CC=CC=1)C=1ON=C(C=1)C(F)(F)F)C2=O WANTWYYPVUJSRC-UHFFFAOYSA-N 0.000 claims 1
- VVMAQBKWLDOZMB-UHFFFAOYSA-N 7-(4-methylimidazol-1-yl)-2-[2-[[2-(trifluoromethyl)-1,3-benzothiazol-7-yl]oxy]ethyl]-3,4-dihydropyrido[1,2-a]pyrazine-1,6-dione Chemical compound C1=NC(C)=CN1C(C1=O)=CC=C2N1CCN(CCOC=1C=3SC(=NC=3C=CC=1)C(F)(F)F)C2=O VVMAQBKWLDOZMB-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims 1
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003693 atypical antipsychotic agent Substances 0.000 claims 1
- 229940127236 atypical antipsychotics Drugs 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161470076P | 2011-03-31 | 2011-03-31 | |
| US61/470,076 | 2011-03-31 | ||
| US201261599022P | 2012-02-15 | 2012-02-15 | |
| US61/599,022 | 2012-02-15 | ||
| PCT/IB2012/051348 WO2012131539A1 (en) | 2011-03-31 | 2012-03-21 | Novel bicyclic pyridinones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014510747A JP2014510747A (ja) | 2014-05-01 |
| JP2014510747A5 true JP2014510747A5 (cg-RX-API-DMAC7.html) | 2014-06-19 |
| JP5767393B2 JP5767393B2 (ja) | 2015-08-19 |
Family
ID=45937491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014501751A Expired - Fee Related JP5767393B2 (ja) | 2011-03-31 | 2012-03-21 | 新規二環式ピリジノン |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8697673B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2691393B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5767393B2 (cg-RX-API-DMAC7.html) |
| AR (1) | AR085748A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2830027C (cg-RX-API-DMAC7.html) |
| ES (1) | ES2602794T3 (cg-RX-API-DMAC7.html) |
| TW (1) | TW201300384A (cg-RX-API-DMAC7.html) |
| UY (1) | UY33978A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2012131539A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2011008335A (es) | 2009-02-06 | 2011-09-06 | Ortho Mcneil Janssen Pharm | Novedosos compuestos heterociclicos biciclicos sustituidos como moduladores de la gamma secretasa. |
| TWI461425B (zh) | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| KR20120024555A (ko) | 2009-05-07 | 2012-03-14 | 얀센 파마슈티칼즈, 인코포레이티드 | 감마 세크레타제 조절제로서의 신규 치환된 인다졸 및 아자-인다졸 유도체 |
| AU2010272578B2 (en) | 2009-07-15 | 2015-03-05 | Cellzome Limited | Substituted triazole and imidazole derivatives as gamma secretase modulators |
| AU2011206635B2 (en) | 2010-01-15 | 2015-01-22 | Cellzome Limited | Novel substituted triazole derivatives as gamma secretase modulators |
| MX2013010970A (es) | 2011-03-24 | 2013-10-17 | Cellzome Ltd | Novedosos derivados de triazolil piperazina y triazolil piperidina sustituidos como moduladores de gamma-secretasa. |
| ES2555167T3 (es) | 2011-07-15 | 2015-12-29 | Janssen Pharmaceuticals, Inc. | Nuevos derivados de indol sustituidos como moduladores de gamma secretasa |
| MX2014009373A (es) | 2012-02-03 | 2014-08-27 | Teva Pharma | Uso de laquinimod para tratar pacientes con enfermedad de crohn que fallaron en la terapia de anti-tnfa de primera linea. |
| JP6106745B2 (ja) * | 2012-05-16 | 2017-04-05 | ヤンセン ファーマシューティカルズ，インコーポレーテッド | （特に）アルツハイマー病の治療に有用な置換３，４−ジヒドロ−２Ｈ−ピリド［１，２−ａ］ピラジン−１，６−ジオン誘導体 |
| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| US20140107154A1 (en) * | 2012-10-12 | 2014-04-17 | Teva Pharmaceutical Industries, Ltd. | Laquinimod for reducing thalamic damage in multiple sclerosis |
| JP2014101316A (ja) * | 2012-11-20 | 2014-06-05 | Toyobo Co Ltd | ベンゾ［１，２−ｄ；４，５−ｄ’］ビスチアゾール化合物の製造方法 |
| CN104918938B (zh) * | 2012-12-20 | 2017-08-15 | 詹森药业有限公司 | 新颖的作为γ分泌酶调节剂的三环3，4‑二氢‑2H‑吡啶并[1，2‑a]吡嗪‑1，6‑二酮衍生物 |
| US10246454B2 (en) | 2013-01-17 | 2019-04-02 | Janssen Pharmaceutica Nv | Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators |
| JP6425717B2 (ja) * | 2013-10-04 | 2018-11-21 | ファイザー・インク | ガンマセクレターゼモジュレーターとしての新規二環式ピリジノン |
| US10562897B2 (en) | 2014-01-16 | 2020-02-18 | Janssen Pharmaceutica Nv | Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators |
| MD4807C1 (ro) * | 2014-01-16 | 2022-12-31 | Fmc Corporation | Derivaţi de pirimidiniloxi-benzen utilizaţi ca erbicide |
| CN103787839B (zh) * | 2014-01-21 | 2015-12-02 | 苏州昊帆生物科技有限公司 | 合成2,3,4,5,6-五氟苯酚的方法 |
| MX369074B (es) * | 2014-04-01 | 2019-10-28 | Pfizer | Cromeno y 1,1a,2,7b-tetrahidrociclopropa[c]cromeno piridopirazinadionas como moduladores de la gamma secretasa. |
| CN103965093A (zh) * | 2014-04-04 | 2014-08-06 | 华南理工大学 | 2-全氟烷基吲哚类化合物及其制备方法和应用 |
| WO2015168103A1 (en) | 2014-04-29 | 2015-11-05 | Teva Pharmaceutical Industries Ltd. | Laquinimod for the treatment of relapsing-remitting multiple sclerosis (rrms) patients with a high disability status |
| MX368391B (es) | 2015-02-03 | 2019-09-30 | Pfizer | Ciclopropabenzofuranil-piridopirazindionas novedosas. |
| WO2016201168A1 (en) | 2015-06-10 | 2016-12-15 | Forum Pharmceuticals Inc. | Oxadiazine compounds and methods of use thereof |
| US11492325B2 (en) * | 2016-05-31 | 2022-11-08 | Human Biomolecular Research Institute | Compounds as inhibitors of sodium channels |
| WO2018031680A1 (en) * | 2016-08-10 | 2018-02-15 | Fronthera U.S. Pharmaceuticals Llc | Novel compounds, uses and methods for their preparation |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CN110256369A (zh) * | 2019-07-01 | 2019-09-20 | 中国人民大学 | 一种制备多氟烷基取代的异恶唑化合物的方法 |
Family Cites Families (114)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1419789A (en) | 1972-08-02 | 1975-12-31 | Pfizer | 2-trifluoromethyl-4-quinolinols |
| NO179904C (no) | 1992-09-04 | 1997-01-08 | Takeda Chemical Industries Ltd | Kondenserte heterocykliske forbindelser og deres anvendelse |
| US5750349A (en) | 1993-01-25 | 1998-05-12 | Takeda Chemical Industries Ltd. | Antibodies to β-amyloids or their derivatives and use thereof |
| NO309272B1 (no) | 1995-03-24 | 2001-01-08 | Takeda Chemical Industries Ltd | Cykliske forbindelser, preparater inneholdende forbindelsene samt mellomprodukter for fremstilling av forbindelsene |
| DE19709877A1 (de) | 1997-03-11 | 1998-09-17 | Bayer Ag | 1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate |
| NZ337765A (en) | 1997-04-09 | 2001-09-28 | Mindset Biopharmaceuticals Usa | Recombinant antibodies having specificity for beta-amyloid N-terminus and C-terminus and use in treating Alzheimer's Disease |
| US8173127B2 (en) | 1997-04-09 | 2012-05-08 | Intellect Neurosciences, Inc. | Specific antibodies to amyloid beta peptide, pharmaceutical compositions and methods of use thereof |
| GB9722520D0 (en) | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| TWI239847B (en) | 1997-12-02 | 2005-09-21 | Elan Pharm Inc | N-terminal fragment of Abeta peptide and an adjuvant for preventing and treating amyloidogenic disease |
| US6905686B1 (en) | 1997-12-02 | 2005-06-14 | Neuralab Limited | Active immunization for treatment of alzheimer's disease |
| CN1229296C (zh) | 1998-03-03 | 2005-11-30 | Ppg工业俄亥俄公司 | 浸渍玻璃纤维束以及包括它的产品 |
| US20020132817A1 (en) | 1998-03-19 | 2002-09-19 | Hideaki Natsugari | Heterocyclic compounds, their production and use |
| EP1145714A4 (en) | 1998-11-27 | 2004-12-15 | Takeda Chemical Industries Ltd | DRUGS |
| MXPA02008145A (es) | 2000-02-24 | 2004-04-05 | Univ Washington | Anticuerpos humanizados que secuestran al peptido beta amiloide. |
| DE10045112A1 (de) | 2000-09-11 | 2002-03-21 | Merck Patent Gmbh | Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems |
| AU2002239764B2 (en) | 2000-11-03 | 2007-06-21 | Proteotech, Inc. | Methods of isolating amyloid-inhibiting compounds and use of compounds isolated from uncaria tomentosa and related plants |
| EP1432444A4 (en) | 2001-08-17 | 2005-11-02 | Lilly Co Eli | ANTI-BETA ANTIBODIES |
| US20030195205A1 (en) | 2001-11-02 | 2003-10-16 | Pfizer Inc. | PDE9 inhibitors for treating cardiovascular disorders |
| DE10238723A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl-substituierte Pyrazolyprimidine |
| DE10238724A1 (de) | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
| EP1549315A4 (en) * | 2002-09-11 | 2007-05-23 | Merck & Co Inc | DIHYDROXYPYRIDOPYRAZINE-1,6-DION COMPOUNDS AS HIV INTEGRASE INHIBITORS |
| PL377769A1 (pl) | 2002-10-09 | 2006-02-20 | Rinat Neuroscience Corp. | Sposób leczenia choroby Alzheimera z zastosowaniem przeciwciał skierowanych przeciw peptydowi beta amyloidu i ich kompozycje |
| AU2003301439A1 (en) | 2002-10-16 | 2004-05-04 | Gilead Sciences, Inc. | Pre-organized tricyclic integrase inhibitor compounds |
| US20040220186A1 (en) | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
| WO2004110996A1 (en) | 2003-06-19 | 2004-12-23 | Pfizer Products Inc. | Nk1 antagonist |
| CA2538220A1 (en) | 2003-09-09 | 2005-03-24 | Takeda Pharmaceutical Company Limited | Use of antibody |
| US7572799B2 (en) | 2003-11-24 | 2009-08-11 | Pfizer Inc | Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors |
| GB0327319D0 (en) | 2003-11-24 | 2003-12-24 | Pfizer Ltd | Novel pharmaceuticals |
| CN1913778A (zh) | 2004-01-28 | 2007-02-14 | 默克公司 | 趋化因子受体活性的氨基环戊基吡啶并吡嗪酮调节剂 |
| EP1720847A1 (en) | 2004-02-02 | 2006-11-15 | Pfizer Products Incorporated | Histamine-3 receptor modulators |
| JP2007528394A (ja) | 2004-03-09 | 2007-10-11 | メルク エンド カムパニー インコーポレーテッド | Ｈｉｖインテグラーゼ阻害薬 |
| SI1742642T1 (sl) | 2004-04-14 | 2009-04-30 | Gilead Sciences Inc | Fosfonatni analogi inhibitorskih spojin HIV integraze |
| US7456164B2 (en) | 2004-05-07 | 2008-11-25 | Pfizer, Inc | 3- or 4-monosubtituted phenol and thiophenol derivatives useful as H3 ligands |
| EP1595881A1 (en) | 2004-05-12 | 2005-11-16 | Pfizer Limited | Tetrahydronaphthyridine derivates useful as histamine H3 receptor ligands |
| EP2298807A3 (en) | 2004-07-30 | 2011-05-18 | Rinat Neuroscience Corp. | Antibodies directed against amyloid-beta peptide and methods using same |
| FR2877015B1 (fr) | 2004-10-21 | 2007-10-26 | Commissariat Energie Atomique | Revetement nanostructure et procede de revetement. |
| GB0423356D0 (en) | 2004-10-21 | 2004-11-24 | Merck Sharp & Dohme | Therapeutic agents |
| WO2006069081A2 (en) | 2004-12-22 | 2006-06-29 | Washington University In St. Louis | USE OF ANTI-Aβ ANTIBODY TO TREAT TRAUMATIC BRAIN INJURY |
| UY29504A1 (es) | 2005-04-29 | 2006-10-31 | Rinat Neuroscience Corp | Anticuerpos dirigidos contra el péptido amiloide beta y métodos que utilizan los mismos. |
| WO2006121831A2 (en) | 2005-05-10 | 2006-11-16 | Merck & Co., Inc. | Hiv integrase inhibitors |
| AU2006245416B2 (en) | 2005-05-12 | 2012-02-23 | Pfizer Inc. | Anhydrous crystalline forms of N-[1-(2-ethoxyethyl)-5-(N-ethyl-N-methylamino)-7-(4-methylpyridin-2-yl-amino)-1H-pyrazolo[4,3-d]pyrimidine-3-carbonyl]methanesulfonamide |
| CA2603830A1 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Co Llc | PYRIDINE [2,3-B] PYRAZINONES |
| WO2006126082A2 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Company Llc | Pyridine [3,4-b] pyrazinones as pde-5 inhibitors |
| WO2006126083A1 (en) | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Company Llc | Pyridine [3 , 4-b] pyrazinone compounds as pde-5 inhibitors |
| CA2607499C (en) | 2005-06-22 | 2010-11-30 | Pfizer Products Inc. | Histamine-3 receptor antagonists |
| TW200713011A (en) | 2005-09-30 | 2007-04-01 | Hon Hai Prec Ind Co Ltd | System, method and electrical apparatus for data transferring |
| US8158673B2 (en) | 2005-10-27 | 2012-04-17 | Pfizer Inc. | Histamine-3 receptor antagonists |
| US20070197532A1 (en) | 2005-11-18 | 2007-08-23 | Cao Sheldon X | Glucokinase activators |
| JP5221144B2 (ja) | 2005-11-24 | 2013-06-26 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | モルホリンタイプ・シンナミド化合物 |
| US20070117839A1 (en) | 2005-11-24 | 2007-05-24 | Eisai R&D Management Co., Ltd. | Two cyclic cinnamide compound |
| WO2007063385A2 (en) | 2005-12-01 | 2007-06-07 | Pfizer Products Inc. | Spirocyclic amine histamine-3 receptor antagonists |
| WO2007069053A1 (en) | 2005-12-14 | 2007-06-21 | Pfizer Products Inc. | Benzimidazole antagonists of the h-3 receptor |
| PE20071321A1 (es) * | 2006-01-20 | 2007-12-29 | Schering Corp | Bencensulfonil-cromano, tiocromano, tetrahidronaftaleno e inhibidores de gamma secretasa relacionados |
| WO2007088450A2 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Chromane antagonist of the h-3 receptor |
| WO2007088462A1 (en) | 2006-02-01 | 2007-08-09 | Pfizer Products Inc. | Spirochromane antagonists of the h-3 receptor |
| WO2007099423A1 (en) | 2006-03-02 | 2007-09-07 | Pfizer Products Inc. | 1-pyrrolidine indane derivatives as histamine-3 receptor antagonists |
| TWI378091B (en) | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| EP2007749A2 (en) | 2006-03-13 | 2008-12-31 | Pfizer Products Inc. | Tetralines antagonists of the h-3 receptor |
| WO2007122466A1 (en) | 2006-04-21 | 2007-11-01 | Pfizer Products Inc. | Pyridine[3,4-b]pyrazinones |
| US8008287B2 (en) | 2006-05-16 | 2011-08-30 | Gilead Sciences, Inc. | Integrase inhibitors |
| EP2019093A4 (en) | 2006-05-19 | 2011-02-23 | Eisai R&D Man Co Ltd | CINEMA ACID AMID DERIVATIVE FROM THE UREA TYPE |
| WO2007138431A2 (en) | 2006-05-30 | 2007-12-06 | Pfizer Products Inc. | Azabicyclic ether histamine-3 antagonists |
| AU2008208653B2 (en) | 2007-01-22 | 2012-11-22 | Pfizer Products Inc. | Tosylate salt of a therapeutic compound and pharmaceutical compositions thereof |
| CA2676920A1 (en) | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperidine derivatives |
| CA2676715A1 (en) | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperazine derivatives for treatment of ad and related conditions |
| US20080207900A1 (en) | 2007-02-28 | 2008-08-28 | Teiji Kimura | Two cyclic oxomorphorin derivatives |
| WO2008137102A2 (en) | 2007-05-04 | 2008-11-13 | Torreypines Therapeutics, Inc. | Methods of modulating amyloid beta and compounds useful therefor |
| US8357682B2 (en) | 2007-05-07 | 2013-01-22 | Zhaoning Zhu | Gamma secretase modulators |
| EP2155740B1 (en) | 2007-05-11 | 2011-01-26 | F. Hoffmann-La Roche AG | Hetarylanilines as modulators for amyloid beta |
| US8426403B2 (en) | 2007-06-01 | 2013-04-23 | Zhaoning Zhu | Gamma secretase modulators |
| WO2008153792A2 (en) | 2007-06-01 | 2008-12-18 | Schering Corporation | Gamma secretase modulators |
| WO2008156580A1 (en) | 2007-06-13 | 2008-12-24 | Merck & Co., Inc. | Triazole derivatives for treating alzheimer's disease and related conditions |
| WO2009005729A1 (en) | 2007-06-29 | 2009-01-08 | Schering Corporation | Gamma secretase modulators |
| US20110009392A1 (en) | 2007-08-06 | 2011-01-13 | Schering Corporation | Gamma secretase modulators |
| US7935815B2 (en) | 2007-08-31 | 2011-05-03 | Eisai R&D Management Co., Ltd. | Imidazoyl pyridine compounds and salts thereof |
| NZ583515A (en) | 2007-08-31 | 2011-05-27 | Eisai R&D Man Co Ltd | Imidazole-pyridine derivative featuring a 1,2,4-triazole ring fused to a 5-7 membered ring, for treating a disease caused by amyloid-beta such as Alzheimer's, dementia, Down's syndrome, and amyloidosis |
| EP2200990A1 (en) | 2007-09-06 | 2010-06-30 | Schering Corporation | Gamma secretase modulators |
| CN101878202A (zh) | 2007-09-28 | 2010-11-03 | 先灵公司 | γ-分泌酶调节剂 |
| GB0720444D0 (en) | 2007-10-18 | 2007-11-28 | Glaxo Group Ltd | Novel compounds |
| WO2009061699A1 (en) | 2007-11-05 | 2009-05-14 | Schering Corporation | Gamma secretase modulators |
| CA2707722A1 (en) | 2007-12-06 | 2009-06-11 | Schering Corporation | Gamma secretase modulators |
| US8426595B2 (en) | 2007-12-11 | 2013-04-23 | Xianhai Huang | Gamma secretase modulators |
| CA2708151A1 (en) | 2007-12-11 | 2009-06-18 | Schering Corporation | Gamma secretase modulators |
| CN101896461A (zh) | 2007-12-13 | 2010-11-24 | 安姆根有限公司 | γ分泌酶调节剂 |
| CN101910142B (zh) | 2008-01-11 | 2013-07-10 | 弗·哈夫曼-拉罗切有限公司 | β-淀粉状蛋白的调节剂 |
| WO2009103652A1 (en) | 2008-02-22 | 2009-08-27 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| US20110027264A1 (en) | 2008-02-29 | 2011-02-03 | Xianhai Huang | Gamma secretase modulators for the treatment of alzheimer's disease |
| US20100137320A1 (en) | 2008-02-29 | 2010-06-03 | Schering Corporation | Gamma secretase modulators |
| BRPI0912539A2 (pt) | 2008-05-05 | 2015-10-13 | Amgen Inc | composto, composição farmacêutica , método para tratar uma doença, e, uso do composto. |
| TW201006801A (en) | 2008-07-18 | 2010-02-16 | Lilly Co Eli | Imidazole carboxamides |
| WO2010019393A1 (en) | 2008-08-13 | 2010-02-18 | Merck Sharp & Dohme Corp. | Pyrimidine derivatives for treatment of alzheimer's disease |
| US20110251172A1 (en) | 2008-08-13 | 2011-10-13 | Rivkin Alexey A | Purine derivatives for treatment of alzheimer's disease |
| EP2324009A1 (en) | 2008-08-27 | 2011-05-25 | Eisai R&D Management Co., Ltd. | Process for preparing certain cinnamide compounds |
| CN102177151A (zh) | 2008-10-09 | 2011-09-07 | 弗·哈夫曼-拉罗切有限公司 | β-淀粉样蛋白的调节剂 |
| US20110263529A1 (en) | 2008-11-06 | 2011-10-27 | Ruo Xu | Gamma secretase modulators |
| EP2356115A1 (en) | 2008-11-06 | 2011-08-17 | Schering Corporation | Gamma secretase modulators |
| EP2367826A4 (en) | 2008-11-06 | 2012-07-04 | Astrazeneca Ab | MODULATORS OF THE PROTEIN -AMYLOID |
| CA2743196A1 (en) | 2008-11-10 | 2010-05-14 | F.Hoffmann-La Roche Ag | Heterocyclic gamma secretase modulators |
| WO2010077582A1 (en) | 2008-12-16 | 2010-07-08 | Merck Sharp & Dohme Corp. | Triazole derivatives for treatment of alzheimer's disease |
| US8575150B2 (en) | 2008-12-16 | 2013-11-05 | Merck Sharp & Dohme Corp. | Triazole derivatives for treatment of Alzheimer's disease |
| PA8854101A1 (es) | 2008-12-18 | 2010-07-27 | Ortho Mcneil Janssen Pharm | Derivados de imidazol bicíclicos sustituidos como moduladores de gamma secretasa |
| JP2012513399A (ja) | 2008-12-22 | 2012-06-14 | シェーリング コーポレイション | γ−セクレターゼ調節剤 |
| CA2747750A1 (en) | 2008-12-22 | 2010-07-01 | Theodros Asberom | Gamma secretase modulators |
| TW201030002A (en) | 2009-01-16 | 2010-08-16 | Bristol Myers Squibb Co | Bicyclic compounds for the reduction of beta-amyloid production |
| MX2011008335A (es) | 2009-02-06 | 2011-09-06 | Ortho Mcneil Janssen Pharm | Novedosos compuestos heterociclicos biciclicos sustituidos como moduladores de la gamma secretasa. |
| TWI461425B (zh) * | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| JP2012051805A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | テトラヒドロトリアゾロピリジン誘導体の製造方法 |
| JP2012051806A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | イミダゾリルピラジン誘導体 |
| JP2012121809A (ja) | 2009-02-26 | 2012-06-28 | Eisai R & D Management Co Ltd | 多環式化合物の製造法およびその中間体 |
| JP2012051807A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | アリールイミダゾール化合物 |
| AU2010218667A1 (en) | 2009-02-26 | 2011-07-21 | Eisai R&D Management Co., Ltd. | Salt of tetrahydrotriazolopyridine derivative and crystal thereof |
| WO2010100606A1 (en) | 2009-03-03 | 2010-09-10 | Pfizer Inc. | Novel phenyl imidazoles and phenyl triazoles as gamma-secretase modulators |
| JP6106745B2 (ja) | 2012-05-16 | 2017-04-05 | ヤンセン ファーマシューティカルズ，インコーポレーテッド | （特に）アルツハイマー病の治療に有用な置換３，４−ジヒドロ−２Ｈ−ピリド［１，２−ａ］ピラジン−１，６−ジオン誘導体 |
| WO2015140614A1 (en) | 2014-03-21 | 2015-09-24 | Align Technology, Inc. | Segmented orthodontic appliance with elastics |
-
2012
- 2012-03-21 JP JP2014501751A patent/JP5767393B2/ja not_active Expired - Fee Related
- 2012-03-21 WO PCT/IB2012/051348 patent/WO2012131539A1/en not_active Ceased
- 2012-03-21 ES ES12713360.1T patent/ES2602794T3/es active Active
- 2012-03-21 EP EP12713360.1A patent/EP2691393B1/en not_active Not-in-force
- 2012-03-21 CA CA2830027A patent/CA2830027C/en not_active Expired - Fee Related
- 2012-03-28 UY UY0001033978A patent/UY33978A/es not_active Application Discontinuation
- 2012-03-28 TW TW101110869A patent/TW201300384A/zh unknown
- 2012-03-29 US US13/433,452 patent/US8697673B2/en active Active
- 2012-03-29 AR ARP120101073A patent/AR085748A1/es not_active Application Discontinuation
-
2013
- 2013-10-15 US US14/053,924 patent/US9067934B2/en active Active