JP2007523909A5 - - Google Patents
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- Publication number
- JP2007523909A5 JP2007523909A5 JP2006554337A JP2006554337A JP2007523909A5 JP 2007523909 A5 JP2007523909 A5 JP 2007523909A5 JP 2006554337 A JP2006554337 A JP 2006554337A JP 2006554337 A JP2006554337 A JP 2006554337A JP 2007523909 A5 JP2007523909 A5 JP 2007523909A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- halo
- alkoxy
- cyclohexyl
- 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 description 88
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 8
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 8
- 102000036530 EDG receptors Human genes 0.000 claims description 7
- 108091007263 EDG receptors Proteins 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 210000004698 lymphocyte Anatomy 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 241001465754 Metazoa Species 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 230000004075 alteration Effects 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 230000002074 deregulated effect Effects 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000011664 signaling Effects 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- WECBDLFIELAVDJ-UHFFFAOYSA-N 1-[[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-2,3-dihydrochromen-7-yl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C(CCO2)=NOCC=3C=C(C(C4CCCCC4)=CC=3)C(F)(F)F)C2=C1 WECBDLFIELAVDJ-UHFFFAOYSA-N 0.000 claims 1
- UXOSEONDYXAAQY-UHFFFAOYSA-N 1-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-3-methoxy-7,8-dihydro-6h-naphthalen-2-yl]methyl]azetidine-3-carboxylic acid Chemical compound COC1=CC=2C(=NOCC=3C=C(C(C4CCCCC4)=CC=3)C(F)(F)F)CCCC=2C=C1CN1CC(C(O)=O)C1 UXOSEONDYXAAQY-UHFFFAOYSA-N 0.000 claims 1
- GNOYLVBEQDEBEV-UHFFFAOYSA-N 1-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-7,8-dihydro-6h-naphthalen-2-yl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(C(CCC2)=NOCC=3C=C(C(C4CCCCC4)=CC=3)C(F)(F)F)C2=C1 GNOYLVBEQDEBEV-UHFFFAOYSA-N 0.000 claims 1
- QQJPDUFMQSQWLT-UHFFFAOYSA-N 1-[[8-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-6,7-dihydro-5h-naphthalen-2-yl]methyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1CC1=CC=C(CCCC2=NOCC=3C=C(C(C4CCCCC4)=CC=3)C(F)(F)F)C2=C1 QQJPDUFMQSQWLT-UHFFFAOYSA-N 0.000 claims 1
- UFDZQYQZIYVKMA-UHFFFAOYSA-N 3-[[3-chloro-5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-7,8-dihydro-6h-naphthalen-2-yl]methylamino]propanoic acid Chemical compound C1=2C=C(Cl)C(CNCCC(=O)O)=CC=2CCCC1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 UFDZQYQZIYVKMA-UHFFFAOYSA-N 0.000 claims 1
- NBWVHSJZOUXTGG-UHFFFAOYSA-N 3-[[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-2,3-dihydrochromen-6-yl]methylamino]propanoic acid Chemical compound C12=CC(CNCCC(=O)O)=CC=C2OCCC1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 NBWVHSJZOUXTGG-UHFFFAOYSA-N 0.000 claims 1
- WXQRXFBWRZRHQT-UHFFFAOYSA-N 3-[[4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-2,3-dihydrochromen-7-yl]methylamino]propanoic acid Chemical compound C1COC2=CC(CNCCC(=O)O)=CC=C2C1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 WXQRXFBWRZRHQT-UHFFFAOYSA-N 0.000 claims 1
- GUYNHJIYFMAAHR-UHFFFAOYSA-N 3-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-3-ethyl-7,8-dihydro-6h-naphthalen-2-yl]methylamino]propanoic acid Chemical compound C1CCC=2C=C(CNCCC(O)=O)C(CC)=CC=2C1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 GUYNHJIYFMAAHR-UHFFFAOYSA-N 0.000 claims 1
- XQQIHUKEIBQKKB-UHFFFAOYSA-N 3-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-3-methoxy-7,8-dihydro-6h-naphthalen-2-yl]methylamino]propanoic acid Chemical compound C1CCC=2C=C(CNCCC(O)=O)C(OC)=CC=2C1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 XQQIHUKEIBQKKB-UHFFFAOYSA-N 0.000 claims 1
- KXUGYIBWAYBOQD-UHFFFAOYSA-N 3-[[5-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-7,8-dihydro-6h-naphthalen-2-yl]methylamino]propanoic acid Chemical compound C1CCC2=CC(CNCCC(=O)O)=CC=C2C1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 KXUGYIBWAYBOQD-UHFFFAOYSA-N 0.000 claims 1
- HIHLNVLPMUSWPM-UHFFFAOYSA-N 3-[[6-chloro-4-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxyimino]-2,3-dihydrochromen-7-yl]methylamino]propanoic acid Chemical compound C1=2C=C(Cl)C(CNCCC(=O)O)=CC=2OCCC1=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 HIHLNVLPMUSWPM-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 125000000815 N-oxide group Chemical group 0.000 claims 1
- 206010029113 Neovascularisation Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Chemical group 0.000 claims 1
- 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 description 9
- 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000027455 binding Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 101000693269 Homo sapiens Sphingosine 1-phosphate receptor 3 Proteins 0.000 description 1
- 101000653759 Homo sapiens Sphingosine 1-phosphate receptor 5 Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102100025747 Sphingosine 1-phosphate receptor 3 Human genes 0.000 description 1
- 102100029802 Sphingosine 1-phosphate receptor 5 Human genes 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000033077 cellular process Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54771204P | 2004-02-24 | 2004-02-24 | |
| US60/547,712 | 2004-02-24 | ||
| PCT/US2005/006123 WO2005082841A1 (en) | 2004-02-24 | 2005-02-24 | Immunosuppressant compounds and compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007523909A JP2007523909A (ja) | 2007-08-23 |
| JP2007523909A5 true JP2007523909A5 (https=) | 2008-04-10 |
| JP4740884B2 JP4740884B2 (ja) | 2011-08-03 |
Family
ID=34910931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006554337A Expired - Fee Related JP4740884B2 (ja) | 2004-02-24 | 2005-02-24 | 免疫抑制性化合物および組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7718704B2 (https=) |
| EP (1) | EP1718604A4 (https=) |
| JP (1) | JP4740884B2 (https=) |
| CN (1) | CN1922135B (https=) |
| AU (1) | AU2005217641B2 (https=) |
| CA (1) | CA2553572A1 (https=) |
| WO (1) | WO2005082841A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101014329B (zh) | 2004-07-16 | 2010-09-08 | 杏林制药株式会社 | 用于对器官或组织的移植的排异反应或骨髓移植的移植物抗宿主反应预防或治疗的药物组合物 |
| EP1806338B1 (en) | 2004-10-12 | 2016-01-20 | Kyorin Pharmaceutical Co., Ltd. | Process for producing 2-amino-2-[2-[4-(3-benzyloxy-phenylthio)-2-chlorophenyl[ethyl]-1,3-propanediol hydrochloride and hydrates thereof. and intermediates the production thereof |
| SI1932522T1 (sl) * | 2005-10-07 | 2012-08-31 | Kyorin Seiyaku Kk | Terapevtsko sredstvo za jetrno bolezen, ki vsebuje 2-amino-1,3- propandiolni derivat kot aktivno sestavino |
| TWI389683B (zh) * | 2006-02-06 | 2013-03-21 | Kyorin Seiyaku Kk | A therapeutic agent for an inflammatory bowel disease or an inflammatory bowel disease treatment using a 2-amino-1,3-propanediol derivative as an active ingredient |
| MX2009001457A (es) | 2006-08-08 | 2009-02-19 | Kyorin Seiyaku Kk | Derivados de aminoalcohol e inmunosupresores que contienen lo mismo como ingrediente activo. |
| JP5188972B2 (ja) * | 2006-08-08 | 2013-04-24 | 杏林製薬株式会社 | アミノリン酸エステル誘導体及びそれらを有効成分とするｓ１ｐ受容体調節剤 |
| WO2009099174A1 (ja) | 2008-02-07 | 2009-08-13 | Kyorin Pharmaceutical Co., Ltd. | アミノアルコール誘導体を有効成分とする炎症性腸疾患の治療剤又は予防剤 |
| EA019252B1 (ru) | 2008-07-23 | 2014-02-28 | Арена Фармасьютикалз, Инк. | ЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ (1,2,3,4-ТЕТРАГИДРОЦИКЛОПЕНТА[b]ИНДОЛ-3-ИЛ)УКСУСНОЙ КИСЛОТЫ, ПРИМЕНИМЫЕ В ЛЕЧЕНИИ АУТОИММУННЫХ И ВОСПАЛИТЕЛЬНЫХ РАССТРОЙСТВ |
| SI2342205T1 (sl) | 2008-08-27 | 2016-09-30 | Arena Pharmaceuticals, Inc. | Substituirani triciklični kislinski derivati kot agonisti S1P1 receptorja, uporabni v zdravljenju avtoimunskih in vnetnih obolenj |
| SG10201906876PA (en) | 2010-01-27 | 2019-09-27 | Arena Pharm 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 |
| SG183416A1 (en) | 2010-03-03 | 2012-09-27 | Arena Pharm Inc | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
| EP2809645A1 (en) * | 2012-02-03 | 2014-12-10 | Novartis AG | Process for preparing n-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-acetimidic acid ethyl ester |
| EP4056179A1 (en) | 2014-12-11 | 2022-09-14 | Actelion Pharmaceuticals Ltd | Dosing regimen for ponesimod, a selective s1p1 receptor agonist |
| MA41139B1 (fr) | 2014-12-11 | 2026-02-27 | Laboratoires Juvise Pharmaceuticals | Combinaison pharmaceutique comprenant du ponesimod et son utilisation dans le traitement de la sclérose en plaque |
| MX386419B (es) | 2015-01-06 | 2025-03-18 | Arena Pharm Inc | Metodos de condiciones de tratamiento relacionadas con el receptor s1p1. |
| EP3939965A1 (en) | 2015-06-22 | 2022-01-19 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid for use in sipi receptor-associated disorders |
| WO2018151834A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| MA47504A (fr) | 2017-02-16 | 2019-12-25 | Arena Pharm Inc | Composés et méthodes de traitement de l'angiocholite biliaire primitive |
| ES2987794T3 (es) | 2018-06-06 | 2024-11-18 | Arena Pharm Inc | Procedimientos de tratamiento de afecciones relacionadas con el receptor S1P1 |
| CN112955431A (zh) | 2018-09-06 | 2021-06-11 | 艾尼纳制药公司 | 可用于治疗自身免疫性病症和炎性病症的化合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3872113A (en) | 1972-05-30 | 1975-03-18 | Endo Lab | Hydroxy- and acetoxy-phthalaldehydric acid, O-(substituted) oximes |
| US5674879A (en) * | 1993-09-24 | 1997-10-07 | G.D. Searle & Co. | Compositions including and methods of using conformationally restricted angiotensin II antagonist |
| IL139470A0 (en) * | 1998-05-11 | 2001-11-25 | Takeda Chemical Industries Ltd | Oxyiminoalkanoic acid derivatives |
| EP1550461A1 (en) * | 2002-06-26 | 2005-07-06 | Ono Pharmaceutical Co., Ltd. | Remedy for chronic disease |
| MXPA05008531A (es) * | 2003-02-11 | 2005-11-17 | Irm Llc | Compuestos biciclicos novedosos y composiciones. |
| MY150088A (en) * | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| CN1791592B (zh) * | 2003-05-19 | 2012-07-04 | Irm责任有限公司 | 免疫抑制剂化合物和组合物 |
-
2005
- 2005-02-24 JP JP2006554337A patent/JP4740884B2/ja not_active Expired - Fee Related
- 2005-02-24 US US10/590,606 patent/US7718704B2/en not_active Expired - Fee Related
- 2005-02-24 CN CN2005800059907A patent/CN1922135B/zh not_active Expired - Fee Related
- 2005-02-24 WO PCT/US2005/006123 patent/WO2005082841A1/en not_active Ceased
- 2005-02-24 AU AU2005217641A patent/AU2005217641B2/en not_active Ceased
- 2005-02-24 EP EP05723826A patent/EP1718604A4/en not_active Withdrawn
- 2005-02-24 CA CA002553572A patent/CA2553572A1/en not_active Abandoned
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