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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- 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 |
|---|---|---|---|---|
| EP2217224B1 (en) | 2007-11-09 | 2019-05-08 | Basf As | Lipid compounds for use in cosmetic products, as food supplement or as a medicament |
| DK2315740T3 (en) | 2008-07-08 | 2018-01-08 | Catabasis Pharmaceuticals Inc | Fatty Acid Acetylated Salicylates and Their Uses |
| 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 |
| HRP20190732T1 (hr) | 2009-05-08 | 2019-06-14 | Basf As | Polinezasićene masne kiseline za liječenje bolesti povezanih s kardiovaskularnim, metaboličkim i upalnim područjima bolesti |
| SG10201509127YA (en) * | 2010-11-05 | 2015-12-30 | Pronova Biopharma Norge As | Methods of treatment using lipid compounds |
| KR102213143B1 (ko) * | 2013-02-28 | 2021-02-08 | 바스프 에이에스 | 지방질 화합물, 트리글리세리드 및 계면활성제를 포함하는 조성물 및 이를 이용하는 방법 |
| EP2889286B1 (en) * | 2013-12-30 | 2016-05-18 | Pax Forschung GmbH | Pharmaceutically active compound for use as anti-inflammatory agent |
| CN107530306A (zh) | 2015-04-28 | 2018-01-02 | 普罗诺瓦生物医药挪威公司 | 结构增强的含硫脂肪酸在预防和/或治疗非酒精性脂肪性肝炎中的用途 |
| ES2996688T3 (en) | 2017-12-06 | 2025-02-13 | Basf As | Fatty acid derivatives for treating non-alcoholic steatohepatitis |
| AU2019274203B2 (en) | 2018-05-23 | 2025-01-02 | Basf As | Structurally modified fatty acids for improving glycemic control and treating inflammatory bowel disease |
| CN116829139A (zh) | 2020-12-22 | 2023-09-29 | 北海医疗私人有限公司 | 用于治疗非酒精性脂肪性肝炎的包含含氧的结构增强的脂肪酸的联合治疗剂 |
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 |
| EP2574340A3 (en) * | 2006-04-07 | 2013-04-17 | Novartis AG | Combination comprising a pyrimidylaminobenzamide compound and a THR315LLEe kinase inhibitor |
| EP2004169B1 (en) * | 2006-04-12 | 2012-08-08 | Unilever PLC | Oral composition comprising a polyunsaturated fatty acid and salicylic acid for obtaining an antiinflammatory effect in skin |
| DK2315740T3 (en) * | 2008-07-08 | 2018-01-08 | Catabasis Pharmaceuticals Inc | Fatty Acid Acetylated Salicylates and Their Uses |
-
2011
- 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 AR ARP110100202A patent/AR079957A1/es unknown
- 2011-01-20 WO PCT/IB2011/000250 patent/WO2011089529A1/en not_active Ceased
- 2011-01-20 EP EP11734428A patent/EP2526084A1/en not_active Withdrawn
- 2011-01-20 TW TW100102111A patent/TW201138832A/zh unknown
- 2011-01-20 JP JP2012549443A patent/JP2013517322A/ja not_active Withdrawn
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