JPH01501710A - 酸素含有複素環式生成物の合成方法およびその生成物 - Google Patents
酸素含有複素環式生成物の合成方法およびその生成物Info
- Publication number
- JPH01501710A JPH01501710A JP63501747A JP50174788A JPH01501710A JP H01501710 A JPH01501710 A JP H01501710A JP 63501747 A JP63501747 A JP 63501747A JP 50174788 A JP50174788 A JP 50174788A JP H01501710 A JPH01501710 A JP H01501710A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- group
- alkyl
- substituted
- tables
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 53
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 17
- 229910052760 oxygen Inorganic materials 0.000 title claims description 17
- 239000001301 oxygen Substances 0.000 title claims description 16
- 230000002194 synthesizing effect Effects 0.000 title description 6
- 125000000623 heterocyclic group Chemical group 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 77
- 239000000203 mixture Substances 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 38
- 239000000126 substance Substances 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical class C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 28
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 claims description 28
- -1 vinylsilane compound Chemical class 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 26
- 238000005949 ozonolysis reaction Methods 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 22
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 21
- 244000180577 Sambucus australis Species 0.000 claims description 20
- 235000018734 Sambucus australis Nutrition 0.000 claims description 20
- 150000002576 ketones Chemical class 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229960004191 artemisinin Drugs 0.000 claims description 17
- 229930101531 artemisinin Natural products 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
- 239000003430 antimalarial agent Substances 0.000 claims description 13
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- 150000001408 amides Chemical class 0.000 claims description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 150000005215 alkyl ethers Chemical group 0.000 claims description 9
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
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- 230000000078 anti-malarial effect Effects 0.000 claims description 5
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- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
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- 229910000077 silane Inorganic materials 0.000 claims description 2
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- 150000003672 ureas Chemical class 0.000 claims 6
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- 210000001217 buttock Anatomy 0.000 claims 3
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- 239000003937 drug carrier Substances 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- BRMWMNQYUAKPOG-UHFFFAOYSA-N OOO[SiH3] Chemical compound OOO[SiH3] BRMWMNQYUAKPOG-UHFFFAOYSA-N 0.000 claims 2
- 230000001681 protective effect Effects 0.000 claims 2
- 125000004811 3-methylpropylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 241000208422 Rhododendron Species 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- BLUAFEHZUWYNDE-XRNKLDBLSA-N chembl77 Chemical class C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4C31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-XRNKLDBLSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000007711 solidification Methods 0.000 claims 1
- 230000008023 solidification Effects 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 83
- 239000000243 solution Substances 0.000 description 65
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
- 239000000463 material Substances 0.000 description 46
- 239000000047 product Substances 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 150000002431 hydrogen Chemical class 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 13
- 238000010586 diagram Methods 0.000 description 13
- 235000011054 acetic acid Nutrition 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 235000019270 ammonium chloride Nutrition 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- 239000013058 crude material Substances 0.000 description 10
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 244000045947 parasite Species 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 230000029936 alkylation Effects 0.000 description 9
- 238000005804 alkylation reaction Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 201000004792 malaria Diseases 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical compound C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
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- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 229960004673 sulfadoxine Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 208000001644 thecoma Diseases 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- GYIODRUWWNNGPI-UHFFFAOYSA-N trimethyl(trimethylsilylmethyl)silane Chemical compound C[Si](C)(C)C[Si](C)(C)C GYIODRUWWNNGPI-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical class O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94355586A | 1986-12-18 | 1986-12-18 | |
| US943,555 | 1986-12-18 | ||
| US10813887A | 1987-10-13 | 1987-10-13 | |
| US10814587A | 1987-10-13 | 1987-10-13 | |
| US108,145 | 1987-10-13 | ||
| US108,138 | 1987-10-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01501710A true JPH01501710A (ja) | 1989-06-15 |
Family
ID=27380423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63501747A Pending JPH01501710A (ja) | 1986-12-18 | 1987-12-15 | 酸素含有複素環式生成物の合成方法およびその生成物 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0346356A1 (enrdf_load_stackoverflow) |
| JP (1) | JPH01501710A (enrdf_load_stackoverflow) |
| CH (1) | CH679486A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3790698T1 (enrdf_load_stackoverflow) |
| GB (1) | GB2218088B (enrdf_load_stackoverflow) |
| SE (2) | SE8802906D0 (enrdf_load_stackoverflow) |
| WO (1) | WO1988004660A2 (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8807523D0 (en) * | 1988-03-30 | 1988-05-05 | Jefford C W | 1,2,4-trioxanes related to arteannuin |
| US5216175A (en) * | 1990-03-23 | 1993-06-01 | Sri International | Antimalarial analogs of artemisinin |
| TW198722B (enrdf_load_stackoverflow) * | 1990-05-07 | 1993-01-21 | Hoechst Ag | |
| WO1993008195A1 (en) * | 1991-10-14 | 1993-04-29 | The University Of Sydney | Cyclic peroxyacetal compounds |
| US6160004A (en) * | 1997-12-30 | 2000-12-12 | Hauser, Inc. | C-10 carbon-substituted artemisinin-like trioxane compounds having antimalarial, antiproliferative and antitumor activities |
| EP0974593A1 (en) * | 1998-07-14 | 2000-01-26 | The Hong Kong University of Science & Technology | Artemisinin derivatives as antiparasitic agents |
-
1987
- 1987-12-15 JP JP63501747A patent/JPH01501710A/ja active Pending
- 1987-12-15 WO PCT/US1987/003330 patent/WO1988004660A2/en not_active Application Discontinuation
- 1987-12-15 CH CH2986/88A patent/CH679486A5/de not_active IP Right Cessation
- 1987-12-15 DE DE19873790698 patent/DE3790698T1/de not_active Withdrawn
- 1987-12-15 GB GB8818816A patent/GB2218088B/en not_active Expired - Lifetime
- 1987-12-15 EP EP88901513A patent/EP0346356A1/en not_active Withdrawn
-
1988
- 1988-08-16 SE SE8802906A patent/SE8802906D0/xx not_active Application Discontinuation
-
1990
- 1990-02-02 SE SE9000377A patent/SE9000377L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SE9000377L (sv) | 1991-08-03 |
| SE9000377D0 (sv) | 1990-02-02 |
| GB2218088B (en) | 1991-07-10 |
| WO1988004660A2 (en) | 1988-06-30 |
| SE8802906L (sv) | 1988-08-16 |
| GB2218088A (en) | 1989-11-08 |
| EP0346356A1 (en) | 1989-12-20 |
| SE8802906D0 (sv) | 1988-08-16 |
| DE3790698T1 (enrdf_load_stackoverflow) | 1988-12-08 |
| GB8818816D0 (en) | 1988-10-05 |
| CH679486A5 (enrdf_load_stackoverflow) | 1992-02-28 |
| WO1988004660A3 (en) | 1988-08-11 |
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