JP2013521301A5 - - Google Patents
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- Publication number
- JP2013521301A5 JP2013521301A5 JP2012556199A JP2012556199A JP2013521301A5 JP 2013521301 A5 JP2013521301 A5 JP 2013521301A5 JP 2012556199 A JP2012556199 A JP 2012556199A JP 2012556199 A JP2012556199 A JP 2012556199A JP 2013521301 A5 JP2013521301 A5 JP 2013521301A5
- Authority
- JP
- Japan
- Prior art keywords
- salt
- trifluoromethyl
- isopropoxy
- pyrrolo
- dihydro
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 48
- -1 4-isopropoxy-3- (trifluoromethyl) benzyloxy Chemical group 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 230000007062 hydrolysis Effects 0.000 claims description 15
- 238000006460 hydrolysis reaction Methods 0.000 claims description 15
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 14
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 238000013213 extrapolation Methods 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000008545 L-lysines Chemical class 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 12
- 238000001757 thermogravimetry curve Methods 0.000 claims description 12
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 7
- RLGFHVZCVPTTLP-OAHLLOKOSA-N 2-[(3r)-4-chloro-6-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C([C@@H](CC(O)=O)CC2)=C2Cl)C2=C1 RLGFHVZCVPTTLP-OAHLLOKOSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 230000004580 weight loss Effects 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- FMRZLMJTOCTKPU-UHFFFAOYSA-N 4-propan-2-yloxy-3-(trifluoromethyl)benzoic acid Chemical compound CC(C)OC1=CC=C(C(O)=O)C=C1C(F)(F)F FMRZLMJTOCTKPU-UHFFFAOYSA-N 0.000 claims description 4
- RNCVVXUSWKAGEL-UHFFFAOYSA-N 4-propan-2-yloxy-3-(trifluoromethyl)benzonitrile Chemical compound CC(C)OC1=CC=C(C#N)C=C1C(F)(F)F RNCVVXUSWKAGEL-UHFFFAOYSA-N 0.000 claims description 4
- 235000019766 L-Lysine Nutrition 0.000 claims description 4
- 239000004472 Lysine Substances 0.000 claims description 4
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- BOYONATXSZSGEJ-UHFFFAOYSA-N [4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methanol Chemical compound CC(C)OC1=CC=C(CO)C=C1C(F)(F)F BOYONATXSZSGEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 238000002411 thermogravimetry Methods 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- NGMORLNIWOFWIA-WZNJZOFCSA-N 2-[(3r)-4-chloro-6-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound NCCCC[C@H](N)C(O)=O.C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C([C@@H](CC(O)=O)CC2)=C2Cl)C2=C1 NGMORLNIWOFWIA-WZNJZOFCSA-N 0.000 claims description 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 3
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 3
- 206010004659 Biliary cirrhosis Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 208000007882 Gastritis Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 206010047642 Vitiligo Diseases 0.000 claims description 3
- 206010000496 acne Diseases 0.000 claims description 3
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 3
- 208000006454 hepatitis Diseases 0.000 claims description 3
- 231100000283 hepatitis Toxicity 0.000 claims description 3
- 208000031225 myocardial ischemia Diseases 0.000 claims description 3
- 208000005987 polymyositis Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
- 206010043778 thyroiditis Diseases 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- JTLOHHFDFSRMRS-UHFFFAOYSA-N 1-(chloromethyl)-3-propan-2-yloxy-2-(trifluoromethyl)benzene Chemical compound CC(C)OC1=CC=CC(CCl)=C1C(F)(F)F JTLOHHFDFSRMRS-UHFFFAOYSA-N 0.000 claims description 2
- FMYJSEMKYVIQCF-QCUBGVIVSA-N 2-[(3R)-4-chloro-6-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1H-pyrrolo[1,2-a]indol-3-yl]acetic acid ethane-1,2-diamine hydrate Chemical compound O.NCCN.C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C([C@@H](CC(O)=O)CC2)=C2Cl)C2=C1 FMYJSEMKYVIQCF-QCUBGVIVSA-N 0.000 claims description 2
- PNIZRKMCXPNJFR-FRRIPSOJSA-N 2-[(3r)-4-chloro-6-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C([C@@H](CC(O)=O)CC2)=C2Cl)C2=C1 PNIZRKMCXPNJFR-FRRIPSOJSA-N 0.000 claims description 2
- XLLSQMOGHKEOOC-XFULWGLBSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;2-[(3r)-4-chloro-6-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetic acid Chemical compound OCC(N)(CO)CO.C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C([C@@H](CC(O)=O)CC2)=C2Cl)C2=C1 XLLSQMOGHKEOOC-XFULWGLBSA-N 0.000 claims description 2
- SKOIWBPVBTURJZ-UHFFFAOYSA-N 4-(chloromethyl)-1-propan-2-yloxy-2-(trifluoromethyl)benzene Chemical compound CC(C)OC1=CC=C(CCl)C=C1C(F)(F)F SKOIWBPVBTURJZ-UHFFFAOYSA-N 0.000 claims description 2
- CQZQCORFYSSCFY-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=C(C#N)C=C1C(F)(F)F CQZQCORFYSSCFY-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- GAAPGHJWCBEJEH-HGPPLOODSA-N C(C)(=O)O.ClC1=C2N(C=3C=CC(=CC13)OCC1=CC(=C(C=C1)OC(C)C)C(F)(F)F)CCC2[C@](N)(CCCNC(N)=N)C(=O)O Chemical compound C(C)(=O)O.ClC1=C2N(C=3C=CC(=CC13)OCC1=CC(=C(C=C1)OC(C)C)C(F)(F)F)CCC2[C@](N)(CCCNC(N)=N)C(=O)O GAAPGHJWCBEJEH-HGPPLOODSA-N 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- RRNJROHIFSLGRA-JEDNCBNOSA-N acetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound CC(O)=O.NCCCC[C@H](N)C(O)=O RRNJROHIFSLGRA-JEDNCBNOSA-N 0.000 claims description 2
- 208000033017 acquired idiopathic inflammatory myopathy Diseases 0.000 claims description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 2
- 239000001639 calcium acetate Substances 0.000 claims description 2
- 235000011092 calcium acetate Nutrition 0.000 claims description 2
- 229960005147 calcium acetate Drugs 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 206010055171 Hypertensive nephropathy Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 claims 1
- 239000011654 magnesium acetate Substances 0.000 claims 1
- 229940069446 magnesium acetate Drugs 0.000 claims 1
- 235000011285 magnesium acetate Nutrition 0.000 claims 1
- 230000010412 perfusion Effects 0.000 claims 1
- MJTTXFOUOIHRKO-XFULWGLBSA-M potassium;2-[(3r)-4-chloro-6-[[4-propan-2-yloxy-3-(trifluoromethyl)phenyl]methoxy]-2,3-dihydro-1h-pyrrolo[1,2-a]indol-3-yl]acetate Chemical compound [K+].C1=C(C(F)(F)F)C(OC(C)C)=CC=C1COC1=CC=C(N2C([C@@H](CC([O-])=O)CC2)=C2Cl)C2=C1 MJTTXFOUOIHRKO-XFULWGLBSA-M 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229960003646 lysine Drugs 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33936210P | 2010-03-03 | 2010-03-03 | |
| US61/339,362 | 2010-03-03 | ||
| PCT/US2011/026806 WO2011109471A1 (en) | 2010-03-03 | 2011-03-02 | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015142650A Division JP2015180706A (ja) | 2010-03-03 | 2015-07-17 | Ｓ１ｐ１受容体修飾物質およびその結晶形の調製のためのプロセス |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013521301A JP2013521301A (ja) | 2013-06-10 |
| JP2013521301A5 true JP2013521301A5 (cg-RX-API-DMAC7.html) | 2014-04-17 |
Family
ID=43838192
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012556199A Abandoned JP2013521301A (ja) | 2010-03-03 | 2011-03-02 | Ｓ１ｐ１受容体修飾物質およびその結晶形の調製のためのプロセス |
| JP2015142650A Abandoned JP2015180706A (ja) | 2010-03-03 | 2015-07-17 | Ｓ１ｐ１受容体修飾物質およびその結晶形の調製のためのプロセス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015142650A Abandoned JP2015180706A (ja) | 2010-03-03 | 2015-07-17 | Ｓ１ｐ１受容体修飾物質およびその結晶形の調製のためのプロセス |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US9085581B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2542554B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP2013521301A (cg-RX-API-DMAC7.html) |
| CN (2) | CN105503882B (cg-RX-API-DMAC7.html) |
| CA (1) | CA2789480A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2558087T3 (cg-RX-API-DMAC7.html) |
| SG (2) | SG183416A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2011109471A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010011316A1 (en) | 2008-07-23 | 2010-01-28 | Arena Pharmaceuticals, Inc. | SUBSTITUTED 1,2,3,4- TETRAHYDROCYCLOPENTA[b]INDOL-3-YL) ACETIC ACID DERIVATIVES USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS |
| KR101800595B1 (ko) | 2008-08-27 | 2017-11-22 | 아레나 파마슈티칼스, 인크. | 자가면역 및 염증성 장애의 치료에 유용한, ｓ1ｐ1 수용체 효능제로서의 치환된 트리시클릭 산 유도체 |
| WO2011094008A1 (en) | 2010-01-27 | 2011-08-04 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| CA2789480A1 (en) * | 2010-03-03 | 2011-09-09 | Arena Pharmaceuticals, Inc. | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
| CN107108535B (zh) * | 2014-10-27 | 2020-04-28 | 塞尔利克斯生物私人有限公司 | 用于治疗多发性硬化的富马酸单甲酯与哌嗪或乙二胺的三组分盐 |
| EP3242666B9 (en) | 2015-01-06 | 2024-12-25 | Arena Pharmaceuticals, Inc. | Compound for use in treating conditions related to the s1p1 receptor |
| IL285890B (en) | 2015-06-22 | 2022-07-01 | Arena Pharm Inc | Slate-free crystal of the arginine salt of (Ar)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-4,3,2,1-tetrahydro-cyclopent[b]indole-3-yl ) acetic acid |
| MX2019009841A (es) | 2017-02-16 | 2020-01-30 | Arena Pharm Inc | Compuestos y metodos para el tratamiento de la colangitis biliar primaria. |
| MA47503A (fr) | 2017-02-16 | 2021-04-21 | Arena Pharm Inc | Composés et méthodes pour le traitement de maladies inflammatoires chroniques de l'intestin avec manifestations extra-intestinales |
| KR102859841B1 (ko) | 2018-06-06 | 2025-09-12 | 아레나 파마슈티칼스, 인크. | S1p1 수용체와 관련된 병태의 치료 방법 |
| WO2020051378A1 (en) | 2018-09-06 | 2020-03-12 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
| EP3870181B1 (en) * | 2018-10-26 | 2024-08-14 | Keros Therapeutics, Inc. | Crystal forms of an alk2 inhibitor |
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| NL293572A (cg-RX-API-DMAC7.html) * | 1962-06-07 | |||
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| US4810699A (en) | 1987-02-20 | 1989-03-07 | American Home Products Corporation | Substituted 1,3,4,9-tetrahydropyrano[3,4,-b]indole-1-acetic acids, pharmaceutical compositions containing them, and methods for treating inflammatory conditions and for analgesic purposes using them |
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| PT95692A (pt) | 1989-10-27 | 1991-09-13 | American Home Prod | Processo para a preparacao de derivados de acidos indole-,indeno-,piranoindole- e tetra-hidrocarbazole-alcanoicos, ou quais sao uteis como inibidores de pla2 e da lipoxigenase |
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-
2011
- 2011-03-02 CA CA2789480A patent/CA2789480A1/en not_active Withdrawn
- 2011-03-02 SG SG2012061685A patent/SG183416A1/en unknown
- 2011-03-02 JP JP2012556199A patent/JP2013521301A/ja not_active Abandoned
- 2011-03-02 SG SG10201501575VA patent/SG10201501575VA/en unknown
- 2011-03-02 ES ES11707330.4T patent/ES2558087T3/es active Active
- 2011-03-02 CN CN201510932844.4A patent/CN105503882B/zh active Active
- 2011-03-02 US US13/581,846 patent/US9085581B2/en active Active
- 2011-03-02 CN CN201180022490.XA patent/CN102884064B/zh active Active
- 2011-03-02 WO PCT/US2011/026806 patent/WO2011109471A1/en not_active Ceased
- 2011-03-02 EP EP11707330.4A patent/EP2542554B1/en active Active
-
2015
- 2015-06-15 US US14/739,341 patent/US20150284399A1/en not_active Abandoned
- 2015-07-17 JP JP2015142650A patent/JP2015180706A/ja not_active Abandoned
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