JP2013517322A5 - - Google Patents
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- JP2013517322A5 JP2013517322A5 JP2012549443A JP2012549443A JP2013517322A5 JP 2013517322 A5 JP2013517322 A5 JP 2013517322A5 JP 2012549443 A JP2012549443 A JP 2012549443A JP 2012549443 A JP2012549443 A JP 2012549443A JP 2013517322 A5 JP2013517322 A5 JP 2013517322A5
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- JP
- Japan
- Prior art keywords
- group
- formula
- ethyl
- alkyl
- compound according
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 27
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- -1 2-((4Z, 7Z, 10Z, 13Z, 16Z, 19Z) -Docosa-4,7,10,13,16,19-hexaen-1-ylthio) -2-ethylbutanamide Chemical compound 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 239000005711 Benzoic acid Substances 0.000 claims 4
- 235000010233 benzoic acid Nutrition 0.000 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229960004889 salicylic acid Drugs 0.000 claims 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 2
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 229960000581 salicylamide Drugs 0.000 claims 2
- YNFAGIJVXPHDIC-YNUSHXQLSA-N 2-[2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoxy]butanoyloxy]benzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCOC(CC)C(=O)OC1=CC=CC=C1C(O)=O YNFAGIJVXPHDIC-YNUSHXQLSA-N 0.000 claims 1
- SMMLHZQODOYOJJ-AAQCHOMXSA-N 2-[2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoxy]butanoylamino]ethyl 2-hydroxybenzoate Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CC)C(=O)NCCOC(=O)C1=CC=CC=C1O SMMLHZQODOYOJJ-AAQCHOMXSA-N 0.000 claims 1
- AWZXNEUJVXHPQZ-AAQCHOMXSA-N 2-[2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoxy]butanoyloxy]benzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CC)C(=O)OC1=CC=CC=C1C(O)=O AWZXNEUJVXHPQZ-AAQCHOMXSA-N 0.000 claims 1
- PKLZTCJBMHHIHQ-NEUKSRIFSA-N 2-[2-[2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoxy]butanoylamino]-4-methylpentanoyl]oxybenzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CC)C(=O)NC(CC(C)C)C(=O)OC1=CC=CC=C1C(O)=O PKLZTCJBMHHIHQ-NEUKSRIFSA-N 0.000 claims 1
- ZJASESHDXNRIHC-QXPCSDSJSA-N 2-[2-[[2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanylbutanoyl]amino]-4-methylpentanoyl]oxybenzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC(CC)(CC)C(=O)NC(CC(C)C)C(=O)OC1=CC=CC=C1C(O)=O ZJASESHDXNRIHC-QXPCSDSJSA-N 0.000 claims 1
- AZIJCDVFPMIUDL-NEUKSRIFSA-N 2-[2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanylbutanoyl]oxybenzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC(CC)(CC)C(=O)OC1=CC=CC=C1C(O)=O AZIJCDVFPMIUDL-NEUKSRIFSA-N 0.000 claims 1
- HPTWCHJHXWFGJM-AAQCHOMXSA-N 2-hydroxy-5-[2-[2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoxy]butanoylamino]ethoxycarbonylamino]benzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CC)C(=O)NCCOC(=O)NC1=CC=C(O)C(C(O)=O)=C1 HPTWCHJHXWFGJM-AAQCHOMXSA-N 0.000 claims 1
- SWCXGYJGUMVZAB-AAQCHOMXSA-N 2-hydroxy-5-[2-[2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenoxy]butanoylamino]ethylcarbamoylamino]benzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCOC(CC)C(=O)NCCNC(=O)NC1=CC=C(O)C(C(O)=O)=C1 SWCXGYJGUMVZAB-AAQCHOMXSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- ACMPWZQOUILVFB-UHFFFAOYSA-N 4-methylpentanamide Chemical compound CC(C)CCC(N)=O ACMPWZQOUILVFB-UHFFFAOYSA-N 0.000 claims 1
- RBQUMWQGAPYHHW-YNUSHXQLSA-N 5-[2-[2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoxy]butanoylamino]ethoxycarbonylamino]-2-hydroxybenzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCOC(CC)C(=O)NCCOC(=O)NC1=CC=C(O)C(C(O)=O)=C1 RBQUMWQGAPYHHW-YNUSHXQLSA-N 0.000 claims 1
- TYSRLDPLSKEEGT-YNUSHXQLSA-N 5-[2-[2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoxy]butanoylamino]ethylcarbamoylamino]-2-hydroxybenzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCOC(CC)C(=O)NCCNC(=O)NC1=CC=C(O)C(C(O)=O)=C1 TYSRLDPLSKEEGT-YNUSHXQLSA-N 0.000 claims 1
- XKKFGWTXBRKUOG-NEUKSRIFSA-N 5-[2-[[2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanylbutanoyl]amino]ethoxycarbonylamino]-2-hydroxybenzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC(CC)(CC)C(=O)NCCOC(=O)NC1=CC=C(O)C(C(O)=O)=C1 XKKFGWTXBRKUOG-NEUKSRIFSA-N 0.000 claims 1
- XRGIZYPIHKDGHV-NEUKSRIFSA-N 5-[2-[[2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanylbutanoyl]amino]ethylcarbamoylamino]-2-hydroxybenzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC(CC)(CC)C(=O)NCCNC(=O)NC1=CC=C(O)C(C(O)=O)=C1 XRGIZYPIHKDGHV-NEUKSRIFSA-N 0.000 claims 1
- YVXZWWIBLVQUAK-QXPCSDSJSA-N 5-[[2-[[2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanylbutanoyl]amino]-4-methylpentanoyl]amino]-2-hydroxybenzoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC(CC)(CC)C(=O)NC(CC(C)C)C(=O)NC1=CC=C(O)C(C(O)=O)=C1 YVXZWWIBLVQUAK-QXPCSDSJSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 102000004877 Insulin Human genes 0.000 claims 1
- 108090001061 Insulin Proteins 0.000 claims 1
- 108010028554 LDL Cholesterol Proteins 0.000 claims 1
- 238000008214 LDL Cholesterol Methods 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 1
- 108010069201 VLDL Cholesterol Proteins 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 229940125396 insulin Drugs 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- YKDXLWCOFFVPPR-YNUSHXQLSA-N n-[2-[2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoxy]butanoylamino]ethyl]-2-hydroxybenzamide Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCOC(CC)C(=O)NCCNC(=O)C1=CC=CC=C1O YKDXLWCOFFVPPR-YNUSHXQLSA-N 0.000 claims 1
- PAZIPSUIDOXUCQ-NEUKSRIFSA-N n-[2-[[2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanylbutanoyl]amino]ethyl]-2-hydroxybenzamide Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC(CC)(CC)C(=O)NCCNC(=O)C1=CC=CC=C1O PAZIPSUIDOXUCQ-NEUKSRIFSA-N 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 0 CC(c1ccccc1*)=I Chemical compound CC(c1ccccc1*)=I 0.000 description 9
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29671710P | 2010-01-20 | 2010-01-20 | |
| US61/296,717 | 2010-01-20 | ||
| PCT/IB2011/000250 WO2011089529A1 (en) | 2010-01-20 | 2011-01-20 | Salicylate fatty acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013517322A JP2013517322A (ja) | 2013-05-16 |
| JP2013517322A5 true JP2013517322A5 (enExample) | 2014-02-13 |
Family
ID=44306439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012549443A Withdrawn JP2013517322A (ja) | 2010-01-20 | 2011-01-20 | サリチレート脂肪酸誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20130046013A1 (enExample) |
| EP (1) | EP2526084A1 (enExample) |
| JP (1) | JP2013517322A (enExample) |
| CN (1) | CN102822141A (enExample) |
| AR (1) | AR079957A1 (enExample) |
| TW (1) | TW201138832A (enExample) |
| WO (1) | WO2011089529A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009061208A1 (en) | 2007-11-09 | 2009-05-14 | Pronova Biopharma Norge As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
| KR101708065B1 (ko) | 2008-07-08 | 2017-02-17 | 카타베이시스 파마슈티칼즈, 인코포레이티드 | 지방산 아세틸화 살리실레이트 및 그 용도 |
| US9085527B2 (en) | 2008-07-08 | 2015-07-21 | Catabasis Pharmaceuticals, Inc. | Fatty acid acylated salicylates and their uses |
| EP2147910A1 (en) * | 2008-07-15 | 2010-01-27 | Pronova BioPharma Norge AS | Novel lipid compounds |
| NZ596386A (en) | 2009-05-08 | 2014-01-31 | Pronova Biopharma Norge As | Polyunsaturated fatty acids for the treatment of diseases related to cardiovascular, metabolic and inflammatory disease areas |
| UA111475C2 (uk) * | 2010-11-05 | 2016-05-10 | Пронова Байофарма Нордж Ас | Способи лікування із застосуванням ліпідних сполук |
| WO2014132134A1 (en) * | 2013-02-28 | 2014-09-04 | Pronova Biopharma Norge As | A composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same |
| EP2889286B1 (en) * | 2013-12-30 | 2016-05-18 | Pax Forschung GmbH | Pharmaceutically active compound for use as anti-inflammatory agent |
| KR20240033300A (ko) | 2015-04-28 | 2024-03-12 | 바스프 에이에스 | 비알코올성 지방간염의 예방 및/또는 치료를 위한 구조적으로 강화된 함황 지방산의 용도 |
| EP3720431B1 (en) | 2017-12-06 | 2024-10-30 | Basf As | Fatty acid derivatives for treating non-alcoholic steatohepatitis |
| KR20210015883A (ko) | 2018-05-23 | 2021-02-10 | 노스씨 테라퓨틱스 비.브이. | 당뇨 제어 및 염증성장질환 치료의 향상을 위한 구조적으로 변형된 지방산 |
| AU2021405273A1 (en) | 2020-12-22 | 2023-08-10 | Northsea Therapeutics B.V. | Combination therapies comprising oxygen-containing structurally enhanced fatty acids for treatment of non-alcoholic steatohepatitis |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036951A (en) * | 1973-03-12 | 1977-07-19 | Synergistics, Inc. | Ultra-violet filtration with certain aminosalicylic acid esters |
| US4264517A (en) * | 1978-12-11 | 1981-04-28 | G.D. Searle & Co. | Alkylphenyl 5Z,8Z,11Z,14Z,17Z-eicosapentaenoates |
| GB9403857D0 (en) * | 1994-03-01 | 1994-04-20 | Scotia Holdings Plc | Fatty acid derivatives |
| ES2400375T3 (es) * | 2006-04-07 | 2013-04-09 | Novartis Ag | Combinación que comprende A) un compuesto de pirimidilaminobenzamida y B)un inhibidor de cinasa THR315LLE |
| ES2391305T3 (es) * | 2006-04-12 | 2012-11-23 | Unilever N.V. | Composición oral que comprende un ácido graso poliinsaturado y ácido salicílico para obtener un efecto antiinflamatorio en la piel |
| KR101708065B1 (ko) * | 2008-07-08 | 2017-02-17 | 카타베이시스 파마슈티칼즈, 인코포레이티드 | 지방산 아세틸화 살리실레이트 및 그 용도 |
-
2011
- 2011-01-20 JP JP2012549443A patent/JP2013517322A/ja not_active Withdrawn
- 2011-01-20 CN CN2011800145715A patent/CN102822141A/zh active Pending
- 2011-01-20 US US13/574,132 patent/US20130046013A1/en not_active Abandoned
- 2011-01-20 EP EP11734428A patent/EP2526084A1/en not_active Withdrawn
- 2011-01-20 AR ARP110100202A patent/AR079957A1/es unknown
- 2011-01-20 TW TW100102111A patent/TW201138832A/zh unknown
- 2011-01-20 WO PCT/IB2011/000250 patent/WO2011089529A1/en not_active Ceased
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