JPS5857434B2 - シンキダイカンジヨウラクトンカゴウブツノ セイゾウホウ - Google Patents
シンキダイカンジヨウラクトンカゴウブツノ セイゾウホウInfo
- Publication number
- JPS5857434B2 JPS5857434B2 JP48104958A JP10495873A JPS5857434B2 JP S5857434 B2 JPS5857434 B2 JP S5857434B2 JP 48104958 A JP48104958 A JP 48104958A JP 10495873 A JP10495873 A JP 10495873A JP S5857434 B2 JPS5857434 B2 JP S5857434B2
- Authority
- JP
- Japan
- Prior art keywords
- chloroform
- group
- compound
- dissolved
- added
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 35
- -1 lactone compound Chemical class 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 11
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 26
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000000862 absorption spectrum Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IEMDOFXTVAPVLX-YWQHLDGFSA-N Leucomycin A1 Chemical compound CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 IEMDOFXTVAPVLX-YWQHLDGFSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FQVHOULQCKDUCY-OGHXVOSASA-N [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(1s,3r,7r,8s,9s,10r,12r,14e,16s)-7-acetyloxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimeth Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@H]1[C@@H](CC=O)C[C@@H](C)C(=O)/C=C/[C@@H]2O[C@H]2C[C@@H](C)OC(=O)C[C@H]([C@@H]1OC)OC(C)=O)[C@H]1C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O1 FQVHOULQCKDUCY-OGHXVOSASA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000012156 elution solvent Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 101000649938 Mus musculus Vacuolar protein sorting-associated protein 28 homolog Proteins 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMPKXDLYZIGGMM-MXYURFFASA-N [(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-4-yl] ac Chemical compound CO[C@H]1[C@H](OC(C)=O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1 VMPKXDLYZIGGMM-MXYURFFASA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229960004144 josamycin Drugs 0.000 description 2
- 239000003120 macrolide antibiotic agent Substances 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MEFKFJOEVLUFAY-UHFFFAOYSA-N (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC(=O)C(Cl)(Cl)Cl MEFKFJOEVLUFAY-UHFFFAOYSA-N 0.000 description 1
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- IEMDOFXTVAPVLX-UHFFFAOYSA-N 15-oxo-cleroda-3,13E-dien-18-oic acid Natural products COC1C(O)CC(=O)OC(C)CC=CC=CC(O)C(C)CC(CC=O)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(OC(=O)CC(C)C)C(C)(O)C2)C(C)O1 IEMDOFXTVAPVLX-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- IEMDOFXTVAPVLX-ADNGMUMBSA-N Leucomycin-A1 Natural products CO[C@H]1[C@H](O)CC(=O)O[C@H](C)CC=CC=C[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]1O[C@H](C)[C@@H](O[C@H]2C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O2)[C@@H]([C@H]1O)N(C)C IEMDOFXTVAPVLX-ADNGMUMBSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 101100489867 Mus musculus Got2 gene Proteins 0.000 description 1
- FWXMGTAGQIUBJN-UHFFFAOYSA-J S(=O)([O-])[O-].[Th+4].S(=O)([O-])[O-] Chemical compound S(=O)([O-])[O-].[Th+4].S(=O)([O-])[O-] FWXMGTAGQIUBJN-UHFFFAOYSA-J 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229950007634 kitasamycin Drugs 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48104958A JPS5857434B2 (ja) | 1973-09-19 | 1973-09-19 | シンキダイカンジヨウラクトンカゴウブツノ セイゾウホウ |
| DE19742444381 DE2444381A1 (de) | 1973-09-19 | 1974-09-17 | Neue makrocyclische lactone und verfahren zu ihrer herstellung |
| HUTO983A HU168326B (enrdf_load_stackoverflow) | 1973-09-19 | 1974-09-18 | |
| DK491574A DK491574A (enrdf_load_stackoverflow) | 1973-09-19 | 1974-09-18 | |
| SE7411756A SE7411756L (enrdf_load_stackoverflow) | 1973-09-19 | 1974-09-18 | |
| GB4064974A GB1478175A (en) | 1973-09-19 | 1974-09-18 | Macrocyclic lactone and its production |
| FR7431650A FR2243948B3 (enrdf_load_stackoverflow) | 1973-09-19 | 1974-09-19 | |
| BE148684A BE820096A (fr) | 1973-09-19 | 1974-09-19 | Nouvelles lactones macrocycliques et leur production |
| CA209,555A CA1026351A (en) | 1973-09-19 | 1974-09-19 | Macrocyclic lactone and its production |
| NL7412412A NL7412412A (nl) | 1973-09-19 | 1974-09-19 | Werkwijze ter bereiding van macrocyclische lactonen. |
| AT755174A AT331405B (de) | 1973-09-19 | 1974-09-19 | Verfahren zur herstellung eines neuen makrocyclischen lactons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48104958A JPS5857434B2 (ja) | 1973-09-19 | 1973-09-19 | シンキダイカンジヨウラクトンカゴウブツノ セイゾウホウ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5058085A JPS5058085A (enrdf_load_stackoverflow) | 1975-05-20 |
| JPS5857434B2 true JPS5857434B2 (ja) | 1983-12-20 |
Family
ID=14394592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48104958A Expired JPS5857434B2 (ja) | 1973-09-19 | 1973-09-19 | シンキダイカンジヨウラクトンカゴウブツノ セイゾウホウ |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2400022A1 (fr) * | 1977-03-09 | 1979-03-09 | Microbial Chem Res Found | Nouveaux derives de macrolactone et leur procede de fabrication |
| DE2858223C2 (enrdf_load_stackoverflow) * | 1977-03-09 | 1989-04-06 | Microbial Chem Res Found |
-
1973
- 1973-09-19 JP JP48104958A patent/JPS5857434B2/ja not_active Expired
-
1974
- 1974-09-17 DE DE19742444381 patent/DE2444381A1/de not_active Withdrawn
- 1974-09-18 DK DK491574A patent/DK491574A/da not_active Application Discontinuation
- 1974-09-18 HU HUTO983A patent/HU168326B/hu unknown
- 1974-09-18 GB GB4064974A patent/GB1478175A/en not_active Expired
- 1974-09-18 SE SE7411756A patent/SE7411756L/xx unknown
- 1974-09-19 BE BE148684A patent/BE820096A/xx unknown
- 1974-09-19 NL NL7412412A patent/NL7412412A/xx not_active Application Discontinuation
- 1974-09-19 AT AT755174A patent/AT331405B/de not_active IP Right Cessation
- 1974-09-19 CA CA209,555A patent/CA1026351A/en not_active Expired
- 1974-09-19 FR FR7431650A patent/FR2243948B3/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HU168326B (enrdf_load_stackoverflow) | 1976-03-28 |
| FR2243948A1 (enrdf_load_stackoverflow) | 1975-04-11 |
| BE820096A (fr) | 1975-01-16 |
| DK491574A (enrdf_load_stackoverflow) | 1975-05-20 |
| NL7412412A (nl) | 1975-03-21 |
| SE7411756L (enrdf_load_stackoverflow) | 1975-03-20 |
| ATA755174A (de) | 1975-11-15 |
| AT331405B (de) | 1976-08-25 |
| GB1478175A (en) | 1977-06-29 |
| CA1026351A (en) | 1978-02-14 |
| FR2243948B3 (enrdf_load_stackoverflow) | 1976-12-10 |
| JPS5058085A (enrdf_load_stackoverflow) | 1975-05-20 |
| DE2444381A1 (de) | 1975-03-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH03223258A (ja) | ２―ニトロイミダゾール誘導体、その製造法及びこれを有効成分とする放射線増感剤 | |
| CN112076200B (zh) | 常春藤皂苷元聚乙二醇衍生物的应用 | |
| WO2013181913A1 (zh) | 一种由青蒿酸制备青蒿素的方法 | |
| US3705179A (en) | Antiandrogenic steroids | |
| WO2023245821A1 (zh) | 一种n-乙酰基-d-半乳糖胺三聚体前体的制备方法 | |
| CN112175037B (zh) | 常春藤皂苷元聚乙二醇衍生物及其制备方法 | |
| Witkop et al. | Aspidospermine. II | |
| CN103494806B (zh) | 苯骈α-吡喃酮类化合物的应用及其制备方法 | |
| JPS5857434B2 (ja) | シンキダイカンジヨウラクトンカゴウブツノ セイゾウホウ | |
| CN105884733B (zh) | 一种稳定同位素标记的莨菪亭及其合成方法 | |
| JP2000169452A (ja) | 新規なアコニチン系化合物および鎮痛・抗炎症剤 | |
| SATO et al. | Chemistry of the Spiroaminoketal Side Chain of Solasodine and Tomatidine. VI. 1 The Beckmann Rearrangement of the Oximino Derivatives | |
| CN101624392B (zh) | F-三唑环-聚乙二醇-2-硝基咪唑化合物及其制备方法 | |
| JPS5936919B2 (ja) | インド−ル誘導体 | |
| CN112300118B (zh) | 一种苯并噻喃二酮化合物及其制备方法和应用 | |
| CN112094278B (zh) | Aurovertin B衍生物及其制备方法与应用 | |
| Singh et al. | Diterpene alkaloids. Isolation and study of two new alkaloids | |
| Kohli et al. | Separation and characterization of the alkaloids of Sarcococca pruniformis | |
| Tomita et al. | Studies on the Alkaloids of Menispermaceous Plants. CXI.: On the Structure of Biscoclaurine Alkaloids.(14).: Synthesis of Trilobine-Type Alkaloid from Isotetrandrine.(1). | |
| CN116143758B (zh) | 一类氮杂黄酮类靶向蛋白嵌合体及其在制备抗肿瘤药物中的应用 | |
| Kametani et al. | Studies on the syntheses of heterocyclic compounds. Part CCCLXXXIX. An alternative synthesis of de-ethyldasycarpidone | |
| JPS58110562A (ja) | 新規な７−チアプロスタグランジンｅ↓１誘導体類、それらの製造方法及びそれらを活性成分とする薬剤 | |
| JPH10503509A (ja) | ８−フルオロ−アントラサイクリン類、それらの調整法及びそれらを含む薬学的組成品 | |
| US4895852A (en) | Antitumor alkaloids | |
| Kupchan et al. | Veratrum alkaloids XLVI. Structure‐activity relationships in a series of analogs of the protoveratrines |