CS200538B2 - Method of producing derivatives of oleandomycin - Google Patents
Method of producing derivatives of oleandomycin Download PDFInfo
- Publication number
- CS200538B2 CS200538B2 CS787694A CS769478A CS200538B2 CS 200538 B2 CS200538 B2 CS 200538B2 CS 787694 A CS787694 A CS 787694A CS 769478 A CS769478 A CS 769478A CS 200538 B2 CS200538 B2 CS 200538B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- deoxy
- singlet
- oxooleandomycin
- added
- acetyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical class O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 39
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 30
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 239000004104 Oleandomycin Substances 0.000 abstract description 5
- 229960002351 oleandomycin Drugs 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- 239000000047 product Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 150000002923 oximes Chemical class 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RXELPOGHCHDCFH-HTPNXTHCSA-N [(3R,5S,6S,7R,8S,9R,12R,13S,14S,15R)-6-[(2S,3R,4S,6R)-3-acetyloxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-8-[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-5,7,9,12,13,15-hexamethyl-10,16-dioxo-1,11-dioxaspiro[2.13]hexadecan-14-yl] acetate Chemical compound CO[C@H]1C[C@H](O[C@H]2[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3OC(C)=O)N(C)C)[C@@H](C)C[C@@]3(CO3)C(=O)[C@H](C)[C@@H](OC(C)=O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]2C)O[C@@H](C)[C@@H]1O RXELPOGHCHDCFH-HTPNXTHCSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- 101150091111 ACAN gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- -1 ketone oximes Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/765,486 US4125705A (en) | 1977-02-04 | 1977-02-04 | Semi-synthetic 4-amino-oleandomycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200538B2 true CS200538B2 (en) | 1980-09-15 |
Family
ID=25073683
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS787694A CS200538B2 (en) | 1977-02-04 | 1978-01-16 | Method of producing derivatives of oleandomycin |
| CS78291A CS200536B2 (en) | 1977-02-04 | 1978-01-16 | Method of producing epimeric 4-amino oleandomycin derivatives |
| CS787693A CS200537B2 (en) | 1977-02-04 | 1978-01-16 | Method of producing epimeric 4-amino oleandomycin derivatives |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS78291A CS200536B2 (en) | 1977-02-04 | 1978-01-16 | Method of producing epimeric 4-amino oleandomycin derivatives |
| CS787693A CS200537B2 (en) | 1977-02-04 | 1978-01-16 | Method of producing epimeric 4-amino oleandomycin derivatives |
Country Status (34)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4124755A (en) * | 1978-01-03 | 1978-11-07 | Pfizer Inc. | 11-Alkanoyl-4"-deoxy-4"-isonitrilo-oleandomycin derivatives |
| US4133950A (en) * | 1978-01-03 | 1979-01-09 | Pfizer Inc. | 4"-Deoxy-4"-carbamate and dithiocarbamate derivatives of oleandomycin and its esters |
| US4413119A (en) * | 1982-03-01 | 1983-11-01 | Pfizer Inc. | Semi-synthetic macrolides |
| US4363803A (en) * | 1982-03-01 | 1982-12-14 | Pfizer Inc. | 3",4"-Oxyallylene erythromycin and oleandomycin, composition and method of use |
| US4429116A (en) | 1982-12-27 | 1984-01-31 | Pfizer Inc. | Alkylated oleandomycin containing compounds |
| JPH0240447U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1988-09-14 | 1990-03-19 | ||
| US5141926A (en) * | 1990-04-18 | 1992-08-25 | Abbott Laboratories | Erythromycin derivatives |
| JPH05155896A (ja) * | 1991-01-18 | 1993-06-22 | Yamanouchi Pharmaceut Co Ltd | 新規マクロライド化合物及びその製造法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3022219A (en) * | 1958-03-07 | 1962-02-20 | Pfizer & Co C | Acyl esters of oleandomycin |
| US3179652A (en) * | 1961-09-05 | 1965-04-20 | Pfizer & Co C | Antibiotic recovery process and salts produced thereby |
| US3836519A (en) * | 1973-05-04 | 1974-09-17 | Abbott Lab | Sulfonyl derivatives of erythromycin |
| US3842069A (en) * | 1973-06-21 | 1974-10-15 | Abbott Lab | 4"-deoxy-4"-oxoerythromycin b derivatives |
| US4036853A (en) * | 1976-08-06 | 1977-07-19 | Pfizer Inc. | Semi-synthetic oleandomycin derivatives-C8 modifications |
-
1977
- 1977-02-04 US US05/765,486 patent/US4125705A/en not_active Expired - Lifetime
- 1977-12-19 YU YU3003/77A patent/YU39504B/xx unknown
- 1977-12-22 ES ES465322A patent/ES465322A1/es not_active Expired
- 1977-12-22 AR AR270472A patent/AR215666A1/es active
-
1978
- 1978-01-05 PH PH20615A patent/PH14836A/en unknown
- 1978-01-10 SE SE7800269A patent/SE445222B/sv not_active IP Right Cessation
- 1978-01-16 BG BG038401A patent/BG32116A3/xx unknown
- 1978-01-16 CS CS787694A patent/CS200538B2/cs unknown
- 1978-01-16 RO RO78100690A patent/RO79264A/ro unknown
- 1978-01-16 RO RO7892910A patent/RO75387A/ro unknown
- 1978-01-16 CS CS78291A patent/CS200536B2/cs unknown
- 1978-01-16 CS CS787693A patent/CS200537B2/cs unknown
- 1978-01-16 BG BG040058A patent/BG32117A4/xx unknown
- 1978-01-16 RO RO78100689A patent/RO79258A/ro unknown
- 1978-01-17 HU HU78PI609A patent/HU179744B/hu unknown
- 1978-01-17 PL PL1978204041A patent/PL111160B1/pl unknown
- 1978-01-17 HU HU813776A patent/HU181395B/hu not_active IP Right Cessation
- 1978-01-17 PL PL1978216290A patent/PL110793B1/pl unknown
- 1978-01-17 SU SU782573251A patent/SU805949A3/ru active
- 1978-01-17 PL PL1978216289A patent/PL113163B1/pl unknown
- 1978-01-23 PT PT67569A patent/PT67569B/pt unknown
- 1978-01-25 DD DD78203409A patent/DD134523A5/xx unknown
- 1978-01-31 CH CH106078A patent/CH629821A5/fr not_active IP Right Cessation
- 1978-02-02 IL IL53959A patent/IL53959A0/xx not_active IP Right Cessation
- 1978-02-02 GB GB4162/78A patent/GB1583921A/en not_active Expired
- 1978-02-02 AT AT72078A patent/AT358169B/de not_active IP Right Cessation
- 1978-02-02 CA CA296,039A patent/CA1106366A/en not_active Expired
- 1978-02-02 GR GR55331A patent/GR68692B/el unknown
- 1978-02-02 DE DE2804509A patent/DE2804509C2/de not_active Expired
- 1978-02-02 ZA ZA00780646A patent/ZA78646B/xx unknown
- 1978-02-03 NL NLAANVRAGE7801259,A patent/NL175997C/xx not_active IP Right Cessation
- 1978-02-03 DK DK51778A patent/DK149628C/da not_active IP Right Cessation
- 1978-02-03 FI FI780355A patent/FI65262C/fi not_active IP Right Cessation
- 1978-02-03 NZ NZ186384A patent/NZ186384A/xx unknown
- 1978-02-03 IE IE240/78A patent/IE46395B1/en not_active IP Right Cessation
- 1978-02-03 LU LU79007A patent/LU79007A1/xx unknown
- 1978-02-03 BE BE184870A patent/BE863618A/xx not_active IP Right Cessation
- 1978-02-03 NO NO780390A patent/NO145955C/no unknown
- 1978-02-03 IT IT20006/78A patent/IT1094211B/it active
- 1978-02-03 AU AU32989/78A patent/AU502293B1/en not_active Expired
- 1978-02-03 JP JP1134978A patent/JPS5398981A/ja active Granted
- 1978-02-03 FR FR7803065A patent/FR2383964A1/fr active Granted
- 1978-07-07 FR FR7820335A patent/FR2396022A1/fr active Granted
- 1978-07-10 SU SU782633653A patent/SU1020004A3/ru active
-
1979
- 1979-03-15 SU SU792739695A patent/SU888824A3/ru active
-
1980
- 1980-12-01 IL IL61606A patent/IL61606A0/xx unknown
-
1981
- 1981-01-30 PH PH25157A patent/PH16491A/en unknown
- 1981-02-04 JP JP56015569A patent/JPS5827799B2/ja not_active Expired
- 1981-06-05 NO NO811914A patent/NO150439C/no unknown
-
1982
- 1982-07-12 YU YU1517/82A patent/YU39517B/xx unknown
- 1982-07-12 YU YU1518/82A patent/YU39518B/xx unknown
-
1983
- 1983-02-16 SE SE8300869A patent/SE457085B/sv not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6069238A (en) | Spirocyclic C-glycosides | |
| AU2001253427B2 (en) | A process for the preparation of 7.alpha.-hydroxy 3-aminosubstituted sterols using intermediates with an unprotected 7.alpha.-hydroxy group | |
| IE861821L (en) | Androsta-1,4-diene-3,17-diones | |
| EP0312867B1 (en) | Billiary acid derivatives, processes for the preparation thereof and phamaceutical compositions containing them | |
| AU2001253427A1 (en) | A process for the preparation of 7.alpha.-hydroxy 3-aminosubstituted sterols using intermediates with an unprotected 7.alpha.-hydroxy group | |
| KR860001469B1 (ko) | 17-(이소시아노-술포닐메틸렌)-스 테로이드류 및 17-(포름아미도-술포닐메틸렌)-스테로이드류의 제조방법 | |
| EP0260975B1 (en) | 4-substituted 6- alkylidenandrostene-3,17-dione derivatives and process for their preparation | |
| CS200538B2 (en) | Method of producing derivatives of oleandomycin | |
| AU775831B2 (en) | Process for preparing 17alpha-acetoxy-11beta-(4-N,N-(dimethylamino)phenyl)-21- methoxy-19-norpregna-4,9-diene-3,20-dione, intermediates useful in the process, and processes for preparing such intermediates | |
| US4501701A (en) | 20-Isocyano-Δ17(20) -steroids | |
| EP0112758B1 (en) | 16-ketoandrostene-17-dithioketals | |
| Kohout et al. | Brassino steroids with androstane and pregnane skeleton | |
| EP0192288B1 (fr) | Nouveaux dérivés stéroides portant en 17 un radical nitrométhylène, Leur application à la préparation de produits biologiquement actifs | |
| FR2479235A1 (fr) | 17-(thio substitue)androst-4-ene(16,17-b)-(1,4)benzodioxin-3-ones a action anti-inflammatoire | |
| US4376733A (en) | Preparation of oxacycloalkenones | |
| EP0084199A1 (en) | Method of preparing delta 5,7-steroids | |
| EP0520879A2 (fr) | Nouveaux stéroides 16-méthyl substitués dérivés de la pregna 1,4-diène 3,20-dione, leur préparation, leur application à la préparation de steroides 16-méthylène et nouveaux intermédiaires | |
| JPS63101397A (ja) | １，２β−メチレン−４−置換アンドロステン−３，１７−ジオン誘導体およびその製造方法 | |
| US4145357A (en) | Steroid derivatives and process for preparing the same | |
| JP3715673B2 (ja) | ビタミンｄ合成中間体の製造方法 | |
| EP1688409B1 (en) | Vitamin d-derived monohalogenovinyl compounds | |
| JP4690039B2 (ja) | １４位で官能化されたタキサン誘導体及びその製造方法 | |
| US4419287A (en) | Stereocontrolled synthesis of steroidal side chains | |
| WO1993021204A1 (en) | Method for preparing cholesta-5,7-diene-3-beta,25-diol and analogs thereof | |
| CS271479B2 (en) | Method of alpha-hydroxy-bicyclo/3,3,0/octane's derivatives production |