CN101054344A - 脂氧素a4类似物 - Google Patents
脂氧素a4类似物 Download PDFInfo
- Publication number
- CN101054344A CN101054344A CNA2007101081453A CN200710108145A CN101054344A CN 101054344 A CN101054344 A CN 101054344A CN A2007101081453 A CNA2007101081453 A CN A2007101081453A CN 200710108145 A CN200710108145 A CN 200710108145A CN 101054344 A CN101054344 A CN 101054344A
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- CN
- China
- Prior art keywords
- compound
- alkyl
- formula
- hydrogen
- straight
- 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
- 150000002635 lipoxin A4 derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 468
- 239000000203 mixture Substances 0.000 claims abstract description 120
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 97
- 125000003118 aryl group Chemical group 0.000 claims abstract description 64
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 56
- 239000001257 hydrogen Substances 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 34
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 37
- 125000001118 alkylidene group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
- 239000011541 reaction mixture Substances 0.000 description 109
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 105
- 238000000034 method Methods 0.000 description 82
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- 238000006243 chemical reaction Methods 0.000 description 69
- 239000000243 solution Substances 0.000 description 64
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 63
- 150000003839 salts Chemical class 0.000 description 58
- 235000002639 sodium chloride Nutrition 0.000 description 58
- 238000002360 preparation method Methods 0.000 description 56
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 54
- -1 1,1-dimethyl ethyl (tertiary butyl) Chemical group 0.000 description 49
- 229920000858 Cyclodextrin Polymers 0.000 description 42
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 41
- 235000019439 ethyl acetate Nutrition 0.000 description 40
- 229910052799 carbon Inorganic materials 0.000 description 39
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 38
- 239000002253 acid Substances 0.000 description 36
- 239000012141 concentrate Substances 0.000 description 36
- 238000005160 1H NMR spectroscopy Methods 0.000 description 35
- 239000003921 oil Substances 0.000 description 34
- 235000019198 oils Nutrition 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 238000002955 isolation Methods 0.000 description 30
- 150000004702 methyl esters Chemical class 0.000 description 30
- 206010061218 Inflammation Diseases 0.000 description 28
- 230000004054 inflammatory process Effects 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- 238000012360 testing method Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- 238000005406 washing Methods 0.000 description 25
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- 229960001866 silicon dioxide Drugs 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 21
- 210000000224 granular leucocyte Anatomy 0.000 description 21
- 239000010410 layer Substances 0.000 description 21
- 210000004072 lung Anatomy 0.000 description 21
- 230000002757 inflammatory effect Effects 0.000 description 20
- 238000012545 processing Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 16
- IXAQOQZEOGMIQS-ORRYEOPJSA-N Lipoxin A Natural products CCCCCC(O)C=CC=C/C=C/C=C/C(O)C(O)CCCC(=O)O IXAQOQZEOGMIQS-ORRYEOPJSA-N 0.000 description 15
- 241000124008 Mammalia Species 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000003814 drug Substances 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- IXAQOQZEOGMIQS-SSQFXEBMSA-N lipoxin A4 Chemical compound CCCCC[C@H](O)\C=C\C=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O IXAQOQZEOGMIQS-SSQFXEBMSA-N 0.000 description 15
- 210000000440 neutrophil Anatomy 0.000 description 15
- 239000000651 prodrug Substances 0.000 description 15
- 229940002612 prodrug Drugs 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- 239000003513 alkali Substances 0.000 description 14
- 239000000010 aprotic solvent Substances 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- 230000005012 migration Effects 0.000 description 14
- 238000013508 migration Methods 0.000 description 14
- 239000002002 slurry Substances 0.000 description 14
- 208000023275 Autoimmune disease Diseases 0.000 description 13
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 13
- 235000011089 carbon dioxide Nutrition 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 210000000222 eosinocyte Anatomy 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical class [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 241001674044 Blattodea Species 0.000 description 10
- 241000282414 Homo sapiens Species 0.000 description 10
- 229930184725 Lipoxin Natural products 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 238000000605 extraction Methods 0.000 description 10
- 238000001727 in vivo Methods 0.000 description 10
- 150000002639 lipoxins Chemical class 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000013566 allergen Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- 208000027866 inflammatory disease Diseases 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 230000000241 respiratory effect Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000010792 warming Methods 0.000 description 9
- 239000012981 Hank's balanced salt solution Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
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- 239000000463 material Substances 0.000 description 7
- 239000002953 phosphate buffered saline Substances 0.000 description 7
- 238000011160 research Methods 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
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Abstract
Description
Claims (23)
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CN114890978A (zh) * | 2022-04-19 | 2022-08-12 | 宿迁医美科技有限公司 | 酚类化合物及其制备方法和应用 |
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US20060154981A1 (en) * | 2005-01-12 | 2006-07-13 | Alcon, Inc. | Method of reducing intraocular pressure and treating glaucoma |
WO2007024589A2 (en) * | 2005-08-24 | 2007-03-01 | The Trustees Of Columbia University In The City Of New York | Phagocyte enhancement therapy for atherosclerosis |
US7687539B1 (en) | 2005-11-07 | 2010-03-30 | Alcon Research, Ltd. | Method of treating ocular allergy |
TW200816991A (en) * | 2006-08-23 | 2008-04-16 | Bayer Schering Pharma Ag | Treatment and prevention of intestinal fibrosis |
BRPI0719509A2 (pt) * | 2006-09-28 | 2013-12-31 | Follica Inc | Métodos, kits e composições para geração de novos folículos pilosos e crescimento de cabelos |
JP2010509240A (ja) * | 2006-11-07 | 2010-03-25 | アルコン リサーチ, リミテッド | 喘息、アレルギー性鼻炎および皮膚障害の治療方法 |
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UY30755A1 (es) * | 2006-12-04 | 2008-07-31 | Bayer Schering Pharma Ag | Sal de potasio cristalina de analogos de lipoxina a4 |
PE20081571A1 (es) * | 2006-12-04 | 2009-01-04 | Bayer Schering Pharma Ag | Acido cristalino de analogos de lipoxina a4 y metodos de prepararlo |
AU2008254925A1 (en) * | 2007-05-15 | 2008-11-27 | Puretech Ventures | Methods and compositions for treating skin conditions |
AU2008301895A1 (en) * | 2007-09-14 | 2009-03-26 | Resolvyx Pharmaceuticals, Inc. | Oxylipin compounds for treating autoimmune diseases |
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WO2009058958A2 (en) * | 2007-10-30 | 2009-05-07 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Lipoxin a4 protection for cornea endothelial cells |
KR20110010755A (ko) * | 2008-05-22 | 2011-02-07 | 바이엘 쉐링 파마 악티엔게젤샤프트 | 결정질 2-((2s,3r,4e,6e,10e,12s)-13-(4-플루오로페녹시)-2,3,12-(트리히드록시트리데카-4,6,10-트리엔-8-이닐)옥시)아세트산의 무수물 및 수화물 형태 |
TW201039815A (en) * | 2009-04-13 | 2010-11-16 | Resolvyx Pharmaceuticals Inc | Compositions and methods for the treatment of inflammation |
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JP2014500275A (ja) | 2010-12-06 | 2014-01-09 | フォリカ,インコーポレイテッド | 禿頭症を治療するため、および毛髪の成長を促進するための方法 |
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KR102086298B1 (ko) * | 2019-10-15 | 2020-03-06 | 건국대학교 산학협력단 | 리폭시게나아제 조합반응에 의한 리폭신 유사체의 제조방법 및 이로부터 제조된 리폭신 유사체 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN114890978A (zh) * | 2022-04-19 | 2022-08-12 | 宿迁医美科技有限公司 | 酚类化合物及其制备方法和应用 |
CN114890978B (zh) * | 2022-04-19 | 2023-07-25 | 宿迁医美科技有限公司 | 酚类化合物及其制备方法和应用 |
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