SU489316A3 - Способ получени производных фузидовой кислоты - Google Patents
Способ получени производных фузидовой кислотыInfo
- Publication number
- SU489316A3 SU489316A3 SU1960938A SU1960938A SU489316A3 SU 489316 A3 SU489316 A3 SU 489316A3 SU 1960938 A SU1960938 A SU 1960938A SU 1960938 A SU1960938 A SU 1960938A SU 489316 A3 SU489316 A3 SU 489316A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- added
- methanol
- mixture
- washed
- Prior art date
Links
- IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical class O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-N 0.000 title description 6
- 238000000034 method Methods 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 150000008064 anhydrides Chemical class 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 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 8
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 5
- IECPWNUMDGFDKC-UHFFFAOYSA-N Fusicsaeure Natural products C12C(O)CC3C(=C(CCC=C(C)C)C(O)=O)C(OC(C)=O)CC3(C)C1(C)CCC1C2(C)CCC(O)C1C IECPWNUMDGFDKC-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960004675 fusidic acid Drugs 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002021 butanolic extract Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- RDDQYPXUIDIYTL-AREPUUQJSA-N 2-[[(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylheptanoyl]amino]acetic acid Chemical compound C1C[C@@H](O)[C@@H](C)[C@@H]2CC[C@]3(C)[C@@]4(C)C[C@H](OC(C)=O)/C(=C(C(=O)NCC(O)=O)/CCCC(C)C)[C@@H]4C[C@@H](O)[C@H]3[C@]21C RDDQYPXUIDIYTL-AREPUUQJSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- IWQPOPSAISBUAH-VOVMJQHHSA-M sodium;2-[[(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyl-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylheptanoyl]amino]ethanesulfonate Chemical compound [Na+].C1C[C@@H](O)[C@@H](C)[C@@H]2CC[C@]3(C)[C@@]4(C)C[C@H](C(C)=O)/C(=C(C(=O)NCCS([O-])(=O)=O)/CCCC(C)C)[C@@H]4C[C@@H](O)[C@H]3[C@]21C IWQPOPSAISBUAH-VOVMJQHHSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
- C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4635172 | 1972-10-06 | ||
| GB4098173A GB1447489A (en) | 1972-10-06 | 1973-08-30 | Fusidic acid conjugates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU489316A3 true SU489316A3 (ru) | 1975-10-25 |
Family
ID=26264559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1960938A SU489316A3 (ru) | 1972-10-06 | 1973-10-05 | Способ получени производных фузидовой кислоты |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3867413A (OSRAM) |
| JP (1) | JPS49132064A (OSRAM) |
| AR (1) | AR199490A1 (OSRAM) |
| AT (1) | AT327384B (OSRAM) |
| AU (1) | AU470769B2 (OSRAM) |
| CA (1) | CA1017324A (OSRAM) |
| CH (1) | CH584238A5 (OSRAM) |
| DD (1) | DD106641A5 (OSRAM) |
| DE (1) | DE2349922A1 (OSRAM) |
| DK (1) | DK131348B (OSRAM) |
| ES (1) | ES419226A1 (OSRAM) |
| FI (1) | FI52098C (OSRAM) |
| FR (1) | FR2201892B1 (OSRAM) |
| GB (1) | GB1447489A (OSRAM) |
| HU (1) | HU166734B (OSRAM) |
| IE (1) | IE38258B1 (OSRAM) |
| IL (1) | IL43287A (OSRAM) |
| LU (1) | LU68566A1 (OSRAM) |
| NL (1) | NL7313732A (OSRAM) |
| PH (1) | PH10337A (OSRAM) |
| SE (1) | SE395705B (OSRAM) |
| SU (1) | SU489316A3 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1490852A (en) * | 1974-09-12 | 1977-11-02 | Leo Pharm Prod Ltd | Fusidic acid derivatives |
| IE44263B1 (en) * | 1975-12-03 | 1981-09-23 | Leo Pharm Prod Ltd | New fusidic acid derivatives |
| US4959358A (en) * | 1983-06-06 | 1990-09-25 | Beth Israel Hospital Assn. | Drug administration |
| US4548922A (en) * | 1983-06-06 | 1985-10-22 | Beth Israel Hospital | Drug administration |
| US4746508A (en) * | 1983-06-06 | 1988-05-24 | Beth Israel Hospital Assn. | Drug administration |
| US4994439A (en) * | 1989-01-19 | 1991-02-19 | California Biotechnology Inc. | Transmembrane formulations for drug administration |
| KR100280367B1 (ko) * | 1999-02-05 | 2001-01-15 | 조생현 | 푸시딘산의 정제방법 |
| US20100239655A1 (en) * | 2004-12-09 | 2010-09-23 | Georgia Levis | Taurine-based compositions and therapeutic methods |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1167643A (fr) * | 1955-04-13 | 1958-11-27 | Chimiotherapie Lab Franc | Nouveaux amides cholaniques et leur procédé d'obtention |
| GB963499A (en) * | 1961-11-15 | 1964-07-08 | Loevens Kemiske Fab | Dihydrofusidic acid and process for preparation thereof |
| US3622669A (en) * | 1967-10-23 | 1971-11-23 | Merck & Co Inc | 5{62 -taurocholenic acids and 5{62 -taurocholadienic acids in compositions for reducing the concentration of cholesterol and liads in blood serum |
| US3708510A (en) * | 1970-09-03 | 1973-01-02 | Merck & Co Inc | Amides of cholanic acid,cholenic acid,and choladienic acid |
-
1973
- 1973-08-30 GB GB4098173A patent/GB1447489A/en not_active Expired
- 1973-09-18 IE IE1662/73A patent/IE38258B1/xx unknown
- 1973-09-21 IL IL43287A patent/IL43287A/en unknown
- 1973-09-24 US US400348A patent/US3867413A/en not_active Expired - Lifetime
- 1973-09-26 CA CA181,959A patent/CA1017324A/en not_active Expired
- 1973-09-27 PH PH15058A patent/PH10337A/en unknown
- 1973-09-27 AT AT830173A patent/AT327384B/de not_active IP Right Cessation
- 1973-10-02 ES ES419226A patent/ES419226A1/es not_active Expired
- 1973-10-03 FI FI733080A patent/FI52098C/fi active
- 1973-10-04 DE DE19732349922 patent/DE2349922A1/de active Pending
- 1973-10-04 DD DD173875A patent/DD106641A5/xx unknown
- 1973-10-04 DK DK538673AA patent/DK131348B/da unknown
- 1973-10-04 JP JP48111079A patent/JPS49132064A/ja active Pending
- 1973-10-04 CH CH1417373A patent/CH584238A5/xx not_active IP Right Cessation
- 1973-10-05 SE SE7313612A patent/SE395705B/xx unknown
- 1973-10-05 NL NL7313732A patent/NL7313732A/xx unknown
- 1973-10-05 SU SU1960938A patent/SU489316A3/ru active
- 1973-10-05 HU HULE723A patent/HU166734B/hu unknown
- 1973-10-05 FR FR7335730A patent/FR2201892B1/fr not_active Expired
- 1973-10-05 AR AR250388A patent/AR199490A1/es active
- 1973-10-05 LU LU68566A patent/LU68566A1/xx unknown
- 1973-10-05 AU AU61070/73A patent/AU470769B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI52098B (OSRAM) | 1977-02-28 |
| CA1017324A (en) | 1977-09-13 |
| AT327384B (de) | 1976-01-26 |
| DD106641A5 (OSRAM) | 1974-06-20 |
| SE395705B (sv) | 1977-08-22 |
| PH10337A (en) | 1976-12-09 |
| DK131348C (OSRAM) | 1975-11-24 |
| FR2201892B1 (OSRAM) | 1977-01-28 |
| DK131348B (da) | 1975-06-30 |
| CH584238A5 (OSRAM) | 1977-01-31 |
| FR2201892A1 (OSRAM) | 1974-05-03 |
| HU166734B (OSRAM) | 1975-05-28 |
| ES419226A1 (es) | 1976-06-16 |
| AU470769B2 (en) | 1976-03-25 |
| AR199490A1 (es) | 1974-09-09 |
| GB1447489A (en) | 1976-08-25 |
| JPS49132064A (OSRAM) | 1974-12-18 |
| IL43287A (en) | 1977-04-29 |
| DE2349922A1 (de) | 1974-04-11 |
| IE38258L (en) | 1974-04-06 |
| IE38258B1 (en) | 1978-02-01 |
| FI52098C (fi) | 1977-06-10 |
| NL7313732A (OSRAM) | 1974-04-09 |
| US3867413A (en) | 1975-02-18 |
| AU6107073A (en) | 1975-04-10 |
| LU68566A1 (OSRAM) | 1973-12-14 |
| ATA830173A (de) | 1975-04-15 |
| IL43287A0 (en) | 1973-11-28 |
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