JPS5967287A - 新規プルセオライド誘導体及びその製造法 - Google Patents
新規プルセオライド誘導体及びその製造法Info
- Publication number
- JPS5967287A JPS5967287A JP57178210A JP17821082A JPS5967287A JP S5967287 A JPS5967287 A JP S5967287A JP 57178210 A JP57178210 A JP 57178210A JP 17821082 A JP17821082 A JP 17821082A JP S5967287 A JPS5967287 A JP S5967287A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- formula
- carboxylic acid
- acid
- 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
- YLWQKYSDNGHLAO-PWRINDRCSA-N bruceolide Chemical class CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](O)C(=O)O[C@@H]4C[C@H]21 YLWQKYSDNGHLAO-PWRINDRCSA-N 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- -1 methoxyethoxymethyl Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 150000007934 α,β-unsaturated carboxylic acids Chemical group 0.000 claims abstract description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 abstract 2
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YLWQKYSDNGHLAO-UHFFFAOYSA-N Bruceolide Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(O)C(=O)OC4CC21 YLWQKYSDNGHLAO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZZZYHIMVKOHVIH-VILODJCFSA-N Brusatol Chemical compound CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](OC(=O)C=C(C)C)C(=O)O[C@@H]4C[C@H]21 ZZZYHIMVKOHVIH-VILODJCFSA-N 0.000 description 3
- ZZZYHIMVKOHVIH-UHFFFAOYSA-N Brusatol Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(=O)C=C(C)C)C(=O)OC4CC21 ZZZYHIMVKOHVIH-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- BIAAQBNMRITRDV-UHFFFAOYSA-N 1-(chloromethoxy)-2-methoxyethane Chemical compound COCCOCCl BIAAQBNMRITRDV-UHFFFAOYSA-N 0.000 description 2
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
- 125000005586 carbonic acid group Chemical group 0.000 description 2
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- YURNCBVQZBJDAJ-AATRIKPKSA-N (E)-hept-2-enoic acid Chemical compound CCCC\C=C\C(O)=O YURNCBVQZBJDAJ-AATRIKPKSA-N 0.000 description 1
- ADLXTJMPCFOTOO-BQYQJAHWSA-N (E)-non-2-enoic acid Chemical compound CCCCCC\C=C\C(O)=O ADLXTJMPCFOTOO-BQYQJAHWSA-N 0.000 description 1
- OTTYFDRFBJPGRW-ONEGZZNKSA-N (e)-pent-2-enoyl chloride Chemical compound CC\C=C\C(Cl)=O OTTYFDRFBJPGRW-ONEGZZNKSA-N 0.000 description 1
- YDWODLQEUPYKGJ-MUVFDYEFSA-N 15-O-acetylbruceolide Chemical compound CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@]3(C(=O)OC)[C@@H]5[C@@H](OC(C)=O)C(=O)O[C@@H]4C[C@H]21 YDWODLQEUPYKGJ-MUVFDYEFSA-N 0.000 description 1
- ADLXTJMPCFOTOO-FPLPWBNLSA-N 2-nonenoic acid Chemical compound CCCCCC\C=C/C(O)=O ADLXTJMPCFOTOO-FPLPWBNLSA-N 0.000 description 1
- NIONDZDPPYHYKY-PLNGDYQASA-N 2Z-Hexenoic acid Chemical compound CCC\C=C/C(O)=O NIONDZDPPYHYKY-PLNGDYQASA-N 0.000 description 1
- CHOGNBXWAZDZBM-UHFFFAOYSA-N 4-(aminomethyl)benzenecarboximidamide Chemical compound NCC1=CC=C(C(N)=N)C=C1 CHOGNBXWAZDZBM-UHFFFAOYSA-N 0.000 description 1
- ZBXITHPYBBXZRG-QYUWQHSUSA-N Brucein E Natural products O[C@H]1[C@H](O)[C@@H]2[C@@]3(C)[C@H](O)[C@@H](O)C=C(C)[C@@H]3C[C@@H]3[C@]22CO[C@@]1(C)[C@]2(O)[C@@H](O)C(=O)O3 ZBXITHPYBBXZRG-QYUWQHSUSA-N 0.000 description 1
- ZBXITHPYBBXZRG-UHFFFAOYSA-N Bruceine E Natural products OC1C(O)C2C3(C)C(O)C(O)C=C(C)C3CC3C22COC1(C)C2(O)C(O)C(=O)O3 ZBXITHPYBBXZRG-UHFFFAOYSA-N 0.000 description 1
- AKSGLPBROCFVSE-TUHDNREHSA-N Bruceoside A Chemical compound O=C([C@@H](C)[C@@H]1C[C@H]2OC(=O)[C@H](OC(=O)C=C(C)C)[C@@H]3[C@]22CO[C@@]3([C@H]([C@H](O)[C@@H]2[C@@]1(C)C=1)O)C(=O)OC)C=1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O AKSGLPBROCFVSE-TUHDNREHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 208000008342 Leukemia P388 Diseases 0.000 description 1
- 241000600169 Maro Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- YDWODLQEUPYKGJ-UHFFFAOYSA-N brucein B Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(C)=O)C(=O)OC4CC21 YDWODLQEUPYKGJ-UHFFFAOYSA-N 0.000 description 1
- ZBXITHPYBBXZRG-ZOKABGNJSA-N bruceine e Chemical compound O[C@H]1[C@H](O)[C@@H]2[C@@]3(C)[C@H](O)[C@@H](O)C=C(C)[C@@H]3C[C@@H]3[C@]22CO[C@]1(C)[C@]2(O)[C@@H](O)C(=O)O3 ZBXITHPYBBXZRG-ZOKABGNJSA-N 0.000 description 1
- ASHBUMOFZXVPPC-IATOJABCSA-N bruceoside A Natural products COC(=O)[C@@]12OC[C@@]34[C@@H](C[C@H]5[C@H](C)C(=O)C(=C[C@]5(C)[C@H]3[C@@H](O)[C@@H]1O)O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)OC(=O)[C@H](OC(=O)C=C(C)C(C)C)[C@@H]24 ASHBUMOFZXVPPC-IATOJABCSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- PAWGRNGPMLVJQH-KHPPLWFESA-N cis-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C/C(O)=O PAWGRNGPMLVJQH-KHPPLWFESA-N 0.000 description 1
- YURNCBVQZBJDAJ-WAYWQWQTSA-N cis-2-heptenoic acid Chemical compound CCCC\C=C/C(O)=O YURNCBVQZBJDAJ-WAYWQWQTSA-N 0.000 description 1
- CWMPPVPFLSZGCY-SREVYHEPSA-N cis-alpha-octenoic acid Chemical compound CCCCC\C=C/C(O)=O CWMPPVPFLSZGCY-SREVYHEPSA-N 0.000 description 1
- YIYBQIKDCADOSF-ARJAWSKDSA-N cis-pent-2-enoic acid Chemical compound CC\C=C/C(O)=O YIYBQIKDCADOSF-ARJAWSKDSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- OIVIDVADCZVCFF-UHFFFAOYSA-N dec-2-enoyl chloride Chemical compound CCCCCCCC=CC(Cl)=O OIVIDVADCZVCFF-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- NVXGQRPGUGAMNJ-UHFFFAOYSA-N hex-2-enoyl chloride Chemical compound CCCC=CC(Cl)=O NVXGQRPGUGAMNJ-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- IXQYZUOOHQWOQL-UHFFFAOYSA-N potassium;methanol;methanolate Chemical compound [K+].OC.[O-]C IXQYZUOOHQWOQL-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 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
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57178210A JPS5967287A (ja) | 1982-10-09 | 1982-10-09 | 新規プルセオライド誘導体及びその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57178210A JPS5967287A (ja) | 1982-10-09 | 1982-10-09 | 新規プルセオライド誘導体及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5967287A true JPS5967287A (ja) | 1984-04-16 |
| JPH0369912B2 JPH0369912B2 (ko) | 1991-11-05 |
Family
ID=16044501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57178210A Granted JPS5967287A (ja) | 1982-10-09 | 1982-10-09 | 新規プルセオライド誘導体及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5967287A (ko) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002062334A3 (en) * | 2001-02-05 | 2003-02-27 | John M Pezzuto | Cancer chemopreventative compounds and compositions and methods of treating cancers |
| CN109776565A (zh) * | 2019-01-28 | 2019-05-21 | 浙江省中医药研究院 | 一种苦味素类化合物及其制备方法与应用 |
| CN113024551A (zh) * | 2021-05-20 | 2021-06-25 | 江西中医药大学 | 一种从鸦胆子中提取分离的新化合物及其制备方法和应用 |
-
1982
- 1982-10-09 JP JP57178210A patent/JPS5967287A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002062334A3 (en) * | 2001-02-05 | 2003-02-27 | John M Pezzuto | Cancer chemopreventative compounds and compositions and methods of treating cancers |
| CN109776565A (zh) * | 2019-01-28 | 2019-05-21 | 浙江省中医药研究院 | 一种苦味素类化合物及其制备方法与应用 |
| CN113024551A (zh) * | 2021-05-20 | 2021-06-25 | 江西中医药大学 | 一种从鸦胆子中提取分离的新化合物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0369912B2 (ko) | 1991-11-05 |
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