CN104382912B - 闭花木酮的o-(咪唑基)乙基衍生物在制备抗缺氧药物中的应用 - Google Patents
闭花木酮的o-(咪唑基)乙基衍生物在制备抗缺氧药物中的应用 Download PDFInfo
- Publication number
- CN104382912B CN104382912B CN201410757757.5A CN201410757757A CN104382912B CN 104382912 B CN104382912 B CN 104382912B CN 201410757757 A CN201410757757 A CN 201410757757A CN 104382912 B CN104382912 B CN 104382912B
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- Prior art keywords
- cleistanone
- imidazole radicals
- ethyl derivative
- medicine
- preparing anti
- 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.)
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- XURLTFUKDPZAPN-QFIPXVFZSA-N Cleistanone Natural products O(C)[C@H]1OC(=O)c2c(-c3cc4OCOc4cc3)c3c(c(O)c12)cc(OC)c(OC)c3 XURLTFUKDPZAPN-QFIPXVFZSA-N 0.000 title claims abstract description 64
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title claims abstract description 31
- 239000003814 drug Substances 0.000 title claims abstract description 15
- 230000000496 anti-anoxic effect Effects 0.000 title claims abstract description 8
- GEIFQLXIDUDMNZ-PCJVTFPHSA-N (4aR,4bR,6aR,8S,10aR,10bR,12R,12aR)-12-hydroxy-1,1,1',1',4a,10a,10b-heptamethyl-3'-methylidenespiro[3,4,4b,5,6,6a,7,9,10,11,12,12a-dodecahydrochrysene-8,2'-cyclopentane]-2-one Chemical compound CC1(C)CCC(=C)[C@@]11C[C@@H](CC[C@H]2[C@]3(C[C@@H](O)[C@H]4C(C)(C)C(=O)CC[C@@]42C)C)[C@@]3(C)CC1 GEIFQLXIDUDMNZ-PCJVTFPHSA-N 0.000 claims abstract description 58
- 206010021143 Hypoxia Diseases 0.000 claims abstract description 25
- 230000007954 hypoxia Effects 0.000 claims description 12
- 206010002660 Anoxia Diseases 0.000 claims description 11
- 241000976983 Anoxia Species 0.000 claims description 11
- 230000007953 anoxia Effects 0.000 claims description 11
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 9
- 229940039009 isoproterenol Drugs 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 206010003497 Asphyxia Diseases 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 abstract description 8
- 238000002474 experimental method Methods 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 241001597008 Nomeidae Species 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 208000035126 Facies Diseases 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000036284 oxygen consumption Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- 241000785597 Cleistanthus Species 0.000 description 3
- 238000012449 Kunming mouse Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 210000002216 heart Anatomy 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- NWCHELUCVWSRRS-SECBINFHSA-N (2r)-2-hydroxy-2-phenylpropanoic acid Chemical class OC(=O)[C@@](O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-SECBINFHSA-N 0.000 description 2
- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 210000000133 brain stem Anatomy 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000002107 myocardial effect Effects 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 241001411320 Eriogonum inflatum Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- SISAYUDTHCIGLM-UHFFFAOYSA-N bromine dioxide Inorganic materials O=Br=O SISAYUDTHCIGLM-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Abstract
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CN201410757757.5A CN104382912B (zh) | 2014-12-10 | 2014-12-10 | 闭花木酮的o-(咪唑基)乙基衍生物在制备抗缺氧药物中的应用 |
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CN201410757757.5A CN104382912B (zh) | 2014-12-10 | 2014-12-10 | 闭花木酮的o-(咪唑基)乙基衍生物在制备抗缺氧药物中的应用 |
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CN104382912A CN104382912A (zh) | 2015-03-04 |
CN104382912B true CN104382912B (zh) | 2016-11-23 |
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CN104840469A (zh) * | 2015-04-15 | 2015-08-19 | 南京广康协生物医药技术有限公司 | 闭花木酮的o-(1h-四氮唑基)乙基衍生物在制备抗缺氧药物中的应用 |
CN104800212A (zh) * | 2015-05-12 | 2015-07-29 | 南京大学 | Daphmalenine A衍生物在制备抗病毒药物中的应用 |
CN104784177A (zh) * | 2015-05-12 | 2015-07-22 | 南京大学 | Daphmalenine A衍生物在制备抗缺氧药物中的应用 |
CN104906089A (zh) * | 2015-05-27 | 2015-09-16 | 南京广康协生物医药技术有限公司 | Daphmalenine A的O-(二乙胺基)乙基衍生物在制备抗缺氧药物中的应用 |
CN105434440A (zh) * | 2015-12-29 | 2016-03-30 | 南京大学 | 一种组合物及其在抗缺氧药物中的应用 |
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CN102198142A (zh) * | 2004-09-07 | 2011-09-28 | 太平洋艾瑞有限公司 | 带有当归酰基的抗肿瘤化合物 |
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Address after: No. 47, Pailou Lane, Gulou District, Nanjing City, Jiangsu Province, 210000 Patentee after: Gu Yukui Address before: 225300 Tianyucun 46, Yonganzhou Town, Gaogang District, Taizhou City, Jiangsu Province Patentee before: Gu Yukui |
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Denomination of invention: Application of O - (imidazolyl) ethyl derivatives of caryophyllone in the preparation of anti hypoxia drugs Effective date of registration: 20210531 Granted publication date: 20161123 Pledgee: Weitang sub branch of Zhejiang Jiashan Rural Commercial Bank Co.,Ltd. Pledgor: Jiashan Weitang Asset Management Co.,Ltd. Registration number: Y2021980004130 |
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Denomination of invention: Application of O - (imidazolyl) ethyl derivatives of cloisonne in the preparation of anti hypoxia drugs Effective date of registration: 20231127 Granted publication date: 20161123 Pledgee: Weitang sub branch of Zhejiang Jiashan Rural Commercial Bank Co.,Ltd. Pledgor: Jiashan Weitang Asset Management Co.,Ltd. Registration number: Y2023330002807 |