JP2017008079A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017008079A5 JP2017008079A5 JP2016158397A JP2016158397A JP2017008079A5 JP 2017008079 A5 JP2017008079 A5 JP 2017008079A5 JP 2016158397 A JP2016158397 A JP 2016158397A JP 2016158397 A JP2016158397 A JP 2016158397A JP 2017008079 A5 JP2017008079 A5 JP 2017008079A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- ester
- pharmaceutically acceptable
- acceptable salt
- methyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 27
- 150000002148 esters Chemical class 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 25
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000001424 substituent group Chemical group 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 4
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- 239000008280 blood Substances 0.000 claims 4
- 210000004369 blood Anatomy 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229940116269 uric acid Drugs 0.000 claims 4
- 201000005569 Gout Diseases 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- FBLDZCRGMITXAP-UHFFFAOYSA-N 1-[(2,6-dimethylphenyl)methyl]-3-methylindole-6-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2C(C)=CN1CC1=C(C)C=CC=C1C FBLDZCRGMITXAP-UHFFFAOYSA-N 0.000 claims 2
- RNHPNYFZQWSPEA-UHFFFAOYSA-N 2-[1-[(2,6-dichlorophenyl)methyl]-3-ethylindazol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(CC)=NN1CC1=C(Cl)C=CC=C1Cl RNHPNYFZQWSPEA-UHFFFAOYSA-N 0.000 claims 2
- POZMFUCEDVKJET-UHFFFAOYSA-N 2-[1-[(2,6-dichlorophenyl)methyl]-3-methylindazol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(C)=NN1CC1=C(Cl)C=CC=C1Cl POZMFUCEDVKJET-UHFFFAOYSA-N 0.000 claims 2
- RNKRTUZHQIFNHZ-UHFFFAOYSA-N 2-[1-[(2,6-dichlorophenyl)methyl]-3-methylindol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(C)=CN1CC1=C(Cl)C=CC=C1Cl RNKRTUZHQIFNHZ-UHFFFAOYSA-N 0.000 claims 2
- LWMWFNZVGKSTIH-UHFFFAOYSA-N 2-[1-[(2,6-dimethylphenyl)methyl]-2,3-dihydroindol-6-yl]acetic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(CC(O)=O)=CC=C2CC1 LWMWFNZVGKSTIH-UHFFFAOYSA-N 0.000 claims 2
- ZAGLHAIDTVHBTF-UHFFFAOYSA-N 2-[1-[(2,6-dimethylphenyl)methyl]-3,3-dimethyl-2h-indol-6-yl]acetic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(CC(O)=O)=CC=C2C(C)(C)C1 ZAGLHAIDTVHBTF-UHFFFAOYSA-N 0.000 claims 2
- VPCKVRLDBHIBOT-UHFFFAOYSA-N 2-[1-[(2,6-dimethylphenyl)methyl]-3-methylindazol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(C)=NN1CC1=C(C)C=CC=C1C VPCKVRLDBHIBOT-UHFFFAOYSA-N 0.000 claims 2
- PPYQJSQNYMYOQT-UHFFFAOYSA-N 2-[1-[(2,6-dimethylphenyl)methyl]-3-methylindol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(C)=CN1CC1=C(C)C=CC=C1C PPYQJSQNYMYOQT-UHFFFAOYSA-N 0.000 claims 2
- UWKOVYZHOSMSSW-UHFFFAOYSA-N 2-[1-[(2-chloro-6-methylphenyl)methyl]-3-methylindazol-6-yl]acetic acid Chemical compound C12=CC(CC(O)=O)=CC=C2C(C)=NN1CC1=C(C)C=CC=C1Cl UWKOVYZHOSMSSW-UHFFFAOYSA-N 0.000 claims 2
- QWDNUOGNNWLMEO-UHFFFAOYSA-N 2-[3-chloro-1-[(2,6-dimethylphenyl)methyl]indol-6-yl]acetic acid Chemical compound CC1=CC=CC(C)=C1CN1C2=CC(CC(O)=O)=CC=C2C(Cl)=C1 QWDNUOGNNWLMEO-UHFFFAOYSA-N 0.000 claims 2
- BULHKEFXUJOWAE-UHFFFAOYSA-N 3-[1-[(2,6-dichlorophenyl)methyl]-3-methylindazol-6-yl]propanoic acid Chemical compound C12=CC(CCC(O)=O)=CC=C2C(C)=NN1CC1=C(Cl)C=CC=C1Cl BULHKEFXUJOWAE-UHFFFAOYSA-N 0.000 claims 2
- QUODMFUSKPAJBO-UHFFFAOYSA-N 3-chloro-1-[(2,6-dichlorophenyl)methyl]pyrazolo[4,3-b]pyridine-6-carboxylic acid Chemical compound C12=CC(C(=O)O)=CN=C2C(Cl)=NN1CC1=C(Cl)C=CC=C1Cl QUODMFUSKPAJBO-UHFFFAOYSA-N 0.000 claims 2
- APUYTWRFCHYMMA-UHFFFAOYSA-N 3-chloro-1-[(2-chloro-6-methylphenyl)methyl]pyrazolo[4,3-b]pyridine-6-carboxylic acid Chemical compound CC1=CC=CC(Cl)=C1CN1C2=CC(C(O)=O)=CN=C2C(Cl)=N1 APUYTWRFCHYMMA-UHFFFAOYSA-N 0.000 claims 2
- 201000001431 Hyperuricemia Diseases 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- -1 carbamoyloxy Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- ASUMVAPLXCRBMA-UHFFFAOYSA-N (3,5-dichloro-4-hydroxyphenyl)-(2,3-dihydro-1,4-benzoxazin-4-yl)methanone Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1C(=O)N1C2=CC=CC=C2OCC1 ASUMVAPLXCRBMA-UHFFFAOYSA-N 0.000 claims 1
- ABUBIFLUOATHFV-UHFFFAOYSA-N 2-[1-[(2,6-dichlorophenyl)methyl]-3-methylindazol-6-yl]-2,2-difluoroacetic acid Chemical compound C12=CC(C(F)(F)C(O)=O)=CC=C2C(C)=NN1CC1=C(Cl)C=CC=C1Cl ABUBIFLUOATHFV-UHFFFAOYSA-N 0.000 claims 1
- 206010007027 Calculus urinary Diseases 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- 229940083914 URAT1 inhibitor Drugs 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 125000005633 phthalidyl group Chemical group 0.000 claims 1
- 230000008085 renal dysfunction Effects 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000008281 urolithiasis Diseases 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011016950 | 2011-01-28 | ||
| JP2011016950 | 2011-01-28 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012554878A Division JP5990106B2 (ja) | 2011-01-28 | 2012-01-30 | 縮環化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017008079A JP2017008079A (ja) | 2017-01-12 |
| JP2017008079A5 true JP2017008079A5 (cg-RX-API-DMAC7.html) | 2017-03-16 |
| JP6223514B2 JP6223514B2 (ja) | 2017-11-01 |
Family
ID=46580968
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012554878A Expired - Fee Related JP5990106B2 (ja) | 2011-01-28 | 2012-01-30 | 縮環化合物 |
| JP2016158397A Expired - Fee Related JP6223514B2 (ja) | 2011-01-28 | 2016-08-12 | 縮環化合物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012554878A Expired - Fee Related JP5990106B2 (ja) | 2011-01-28 | 2012-01-30 | 縮環化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8987473B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2669270B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5990106B2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK2669270T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2012102405A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2860382C (en) | 2011-12-21 | 2017-09-12 | Allergan, Inc. | Compounds acting at multiple prostaglandin receptors giving a general anti-inflammatory response |
| DK3444238T3 (da) | 2012-07-27 | 2022-01-03 | Sato Pharma | Fremgangsmåde til fremstilling af difluormethylenforbindelser |
| CN102875590A (zh) * | 2012-10-22 | 2013-01-16 | 北京林业大学 | 芳香族三丁基锡衍生物的制备方法 |
| CN108516958B (zh) | 2015-03-24 | 2020-07-17 | 上海璎黎药业有限公司 | 稠环衍生物、其制备方法、中间体、药物组合物及应用 |
| AU2016356694B2 (en) | 2015-11-20 | 2021-07-29 | Forma Therapeutics, Inc. | Purinones as ubiquitin-specific protease 1 inhibitors |
| CN106045898B (zh) * | 2016-06-28 | 2019-05-24 | 广东东阳光药业有限公司 | 一种吲哚类化合物及其制备方法和用途 |
| CN106146533B (zh) * | 2016-07-14 | 2018-04-03 | 华润赛科药业有限责任公司 | 含硫杂环羧酸类衍生物、其制备方法和应用 |
| US11453858B2 (en) | 2016-11-11 | 2022-09-27 | Whitehead Institute For Biomedical Research | Human plasma-like medium |
| US11447503B2 (en) | 2019-06-14 | 2022-09-20 | Janssen Pharmaceutica Nv | Pyridine carbamates and their use as GLUN2B receptor modulators |
| TWI774755B (zh) * | 2017-04-28 | 2022-08-21 | 日商佐藤製藥股份有限公司 | 二氟甲烯化合物之製造法 |
| JP2020523309A (ja) | 2017-06-08 | 2020-08-06 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | ピラゾロピリミジンpde9インヒビター |
| US20200172483A1 (en) * | 2017-06-22 | 2020-06-04 | Curadev Pharma Limited | Heterocyclic small molecule modulators of human sting |
| HUE066335T2 (hu) | 2018-10-05 | 2024-07-28 | Annapurna Bio Inc | Vegyületek és készítmények APJ receptor aktivitáshoz kapcsolódó állapotok kezelésére |
| JP2022536424A (ja) | 2019-06-14 | 2022-08-16 | ヤンセン ファーマシューティカ エヌ.ベー. | 置換ヘテロ芳香族ピラゾロピリジン及びglun2b受容体調節因子としてのそれらの使用 |
| CA3142998A1 (en) | 2019-06-14 | 2020-12-17 | Janssen Pharmaceutica Nv | Pyrazine carbamates and their use as glun2b receptor modulators |
| MX2021015500A (es) | 2019-06-14 | 2022-02-10 | Janssen Pharmaceutica Nv | Pirazolo-pirazinas sustituidas y su uso como moduladores del receptor glun2b. |
| TW202112774A (zh) * | 2019-06-14 | 2021-04-01 | 比利時商健生藥品公司 | 經取代之吡唑并-吡啶醯胺及其作為glun2b受體調節劑之用途 |
| GB202013728D0 (en) * | 2020-09-01 | 2020-10-14 | Nrg Therapeutics Ltd | Novel compounds |
| JP7588224B2 (ja) | 2020-10-05 | 2024-11-21 | エンライブン インコーポレイテッド | Bcr-ablチロシンキナーゼの阻害のための5-及び6-アザインドール化合物 |
| TW202334089A (zh) | 2021-11-02 | 2023-09-01 | 美商夫雷爾醫療公司 | Pparg反向激動劑及其用途 |
| EP4516781A1 (en) * | 2022-04-27 | 2025-03-05 | Atom Therapeutics Co., Ltd. | Compound for reducing uric acid |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0470543A1 (de) * | 1990-08-10 | 1992-02-12 | Dr. Karl Thomae GmbH | Heterocyclische Imidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zur ihrer Herstellung |
| GB9121776D0 (en) | 1991-10-14 | 1991-11-27 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives and process for preparation thereof |
| WO1996003377A1 (en) * | 1994-07-27 | 1996-02-08 | Sankyo Company, Limited | Heterocyclic compounds, useful as allosteric effectors at muscarinic receptors |
| ATE219765T1 (de) * | 1995-04-10 | 2002-07-15 | Fujisawa Pharmaceutical Co | Indolderivate als cgmp-pde inhibitoren |
| US6045398A (en) | 1995-07-10 | 2000-04-04 | International Business Machines Corporation | Battery accepting unit and battery pack |
| IL124969A (en) | 1995-12-28 | 2002-09-12 | Fujisawa Pharmaceutical Co | History of benzimidazole, processes for their preparation and pharmaceutical preparations containing them |
| AUPO118896A0 (en) * | 1996-07-23 | 1996-08-15 | Fujisawa Pharmaceutical Co., Ltd. | New use |
| AU3899097A (en) * | 1996-08-05 | 1998-02-25 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted aromatic compounds |
| AU4400597A (en) * | 1996-10-08 | 1998-05-05 | Fujisawa Pharmaceutical Co., Ltd. | Indole derivatives |
| JPH10114654A (ja) * | 1996-10-09 | 1998-05-06 | Fujisawa Pharmaceut Co Ltd | 新規用途 |
| TW453999B (en) | 1997-06-27 | 2001-09-11 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| EP0995742A4 (en) | 1997-06-27 | 2004-08-25 | Fujisawa Pharmaceutical Co | SULPHONAMIDE COMPOUNDS AND THEIR MEDICAL USE |
| US6410584B1 (en) * | 1998-01-14 | 2002-06-25 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells with indole derivatives |
| US6358992B1 (en) * | 1998-11-25 | 2002-03-19 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with indole derivatives |
| EP1142880A4 (en) | 1998-12-24 | 2002-02-27 | Fujisawa Pharmaceutical Co | BENZIMIDAZOLE DERIVATIVES |
| AU1028601A (en) | 1999-11-05 | 2001-05-14 | Smithkline Beecham Plc | Isoquinoline and quinazoline derivatives having a combined 5ht1a, 5ht1b and 5ht1d receptor activity |
| AU2002349477A1 (en) * | 2001-11-26 | 2003-06-10 | Takeda Chemical Industries, Ltd. | Bicyclic derivative, process for producing the same, and use |
| AU2003902860A0 (en) * | 2003-06-06 | 2003-06-26 | Daicel Chemical Industries, Ltd | Benzimidazole compounds |
| AR051780A1 (es) * | 2004-11-29 | 2007-02-07 | Japan Tobacco Inc | Compuestos en anillo fusionados que contienen nitrogeno y utilizacion de los mismos |
| EP1985297A1 (en) | 2006-01-27 | 2008-10-29 | Japan Tobacco, Inc. | Carboxylic acid compound and use thereof |
| US20070197512A1 (en) | 2006-01-27 | 2007-08-23 | Japan Tobacco Inc. | Carboxylic Acid Compounds and Use Thereof |
| AU2007218781A1 (en) | 2006-02-20 | 2007-08-30 | Astellas Pharma Inc. | Amide derivative or salt thereof |
| CA2644809A1 (en) | 2006-03-02 | 2007-09-07 | Astellas Pharma Inc. | 17 .beta. hsd type 5 inhibitor |
| US8338416B2 (en) | 2006-03-16 | 2012-12-25 | Pharmacylics, Inc. | Indole derivatives as inhibitors of histone deacetylase |
| MX337906B (es) * | 2006-10-19 | 2016-03-28 | Signal Pharm Llc | Compuestos de heteroarilo, composiciones de los mismos, y su uso como inhibidores de proteina cinasas. |
| US8501747B2 (en) * | 2007-02-13 | 2013-08-06 | Merck Sharp & Dohme Corp. | Functionally selective alpha2C adrenoreceptor agonists |
| DK2133332T3 (da) | 2007-04-11 | 2013-09-30 | Kissei Pharmaceutical | (aza)indolderivat og anvendelse deraf til medicinske formål |
| US9149463B2 (en) | 2007-09-18 | 2015-10-06 | The Board Of Trustees Of The Leland Standford Junior University | Methods and compositions of treating a Flaviviridae family viral infection |
| US8829058B2 (en) | 2008-03-13 | 2014-09-09 | Wellstat Therapeutics Corporation | Compounds and method for reducing uric acid |
| CA2721218C (en) | 2008-04-15 | 2015-03-24 | Pharmacyclics, Inc. | Selective inhibitors of histone deacetylase |
| KR101048448B1 (ko) * | 2008-11-21 | 2011-07-11 | 한국화학연구원 | 신규 피라졸로[4,3-b]피리딘 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약학적 조성물 |
| JP2012520884A (ja) * | 2009-03-18 | 2012-09-10 | ザ ボード オブ トラスティーズ オブ ザ リランド スタンフォード ジュニア ユニバーシティー | フラビウイルス科ウイルス感染症を治療する方法および組成物 |
| JP2011246389A (ja) * | 2010-05-26 | 2011-12-08 | Oncotherapy Science Ltd | Ttk阻害作用を有する縮環ピラゾール誘導体 |
-
2012
- 2012-01-30 US US13/982,200 patent/US8987473B2/en not_active Expired - Fee Related
- 2012-01-30 WO PCT/JP2012/052009 patent/WO2012102405A1/ja not_active Ceased
- 2012-01-30 DK DK12739424.5T patent/DK2669270T3/en active
- 2012-01-30 EP EP12739424.5A patent/EP2669270B1/en not_active Not-in-force
- 2012-01-30 JP JP2012554878A patent/JP5990106B2/ja not_active Expired - Fee Related
-
2015
- 2015-02-11 US US14/619,980 patent/US9359350B2/en not_active Expired - Fee Related
-
2016
- 2016-08-12 JP JP2016158397A patent/JP6223514B2/ja not_active Expired - Fee Related