HU186974B - Process for the preparation of 3a,7a-trans-4-bracket-7,7-ethylendioxy-3-oxo-octyl-bracket closed-7abeta-methyl-perhydro-indan-1,5-dione - Google Patents
Process for the preparation of 3a,7a-trans-4-bracket-7,7-ethylendioxy-3-oxo-octyl-bracket closed-7abeta-methyl-perhydro-indan-1,5-dione Download PDFInfo
- Publication number
- HU186974B HU186974B HU823085A HU308579A HU186974B HU 186974 B HU186974 B HU 186974B HU 823085 A HU823085 A HU 823085A HU 308579 A HU308579 A HU 308579A HU 186974 B HU186974 B HU 186974B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- dione
- methyl
- bracket
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 26
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 17
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 16
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims abstract description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 18
- -1 anhydride steroid Chemical class 0.000 abstract description 10
- 239000000543 intermediate Substances 0.000 abstract description 6
- 150000003431 steroids Chemical class 0.000 abstract description 5
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- JRIZOGLBRPZBLQ-QXUSFIETSA-N 19-Norandrostenedione Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JRIZOGLBRPZBLQ-QXUSFIETSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000003747 Grignard reaction Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- MYNXCIIVUSXMDZ-UHFFFAOYSA-N 5-chloropentan-2-one;ethene Chemical group C=C.CC(=O)CCCCl MYNXCIIVUSXMDZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- JSCNFEFJALUGBY-UHFFFAOYSA-N 2,3-dioxopropanoic acid Chemical group OC(=O)C(=O)C=O JSCNFEFJALUGBY-UHFFFAOYSA-N 0.000 description 1
- FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 description 1
- VMAKIQSICJHVNP-UHFFFAOYSA-N 2-(3-bromopropyl)-2-methyl-1,3-dioxolane Chemical compound BrCCCC1(C)OCCO1 VMAKIQSICJHVNP-UHFFFAOYSA-N 0.000 description 1
- OFERIRWCHSOJJT-UHFFFAOYSA-N 2-(3-chloropropyl)-2-methyl-1,3-dioxolane Chemical compound ClCCCC1(C)OCCO1 OFERIRWCHSOJJT-UHFFFAOYSA-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/916,443 US4158012A (en) | 1978-06-19 | 1978-06-19 | Steroid synthesis process using mixed anhydride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186974B true HU186974B (en) | 1985-10-28 |
Family
ID=25437272
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU823085A HU186974B (en) | 1978-06-19 | 1979-06-18 | Process for the preparation of 3a,7a-trans-4-bracket-7,7-ethylendioxy-3-oxo-octyl-bracket closed-7abeta-methyl-perhydro-indan-1,5-dione |
| HU79SI1701A HU181503B (en) | 1978-06-19 | 1979-06-18 | Process for producing 3,3-ethylenedioxy-4,5-seco-19-nor-androst-9-ene-5,17-dione |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79SI1701A HU181503B (en) | 1978-06-19 | 1979-06-18 | Process for producing 3,3-ethylenedioxy-4,5-seco-19-nor-androst-9-ene-5,17-dione |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4158012A (en, 2012) |
| EP (1) | EP0006355B1 (en, 2012) |
| JP (3) | JPS552675A (en, 2012) |
| AT (1) | ATE7600T1 (en, 2012) |
| CS (2) | CS212220B2 (en, 2012) |
| DD (1) | DD144269A5 (en, 2012) |
| DE (1) | DE2967004D1 (en, 2012) |
| DK (2) | DK246479A (en, 2012) |
| ES (1) | ES481650A1 (en, 2012) |
| HK (1) | HK96787A (en, 2012) |
| HU (2) | HU186974B (en, 2012) |
| MY (1) | MY8700665A (en, 2012) |
| PL (2) | PL118827B1 (en, 2012) |
| SG (1) | SG38287G (en, 2012) |
| SU (1) | SU999977A3 (en, 2012) |
| YU (1) | YU41160B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4400524A (en) * | 1981-07-28 | 1983-08-23 | The Upjohn Company | Grignard reagents prepared from 5-halopentan-2-one propylene ketals |
| JPS58134577A (ja) * | 1982-02-05 | 1983-08-10 | Nippon Kogaku Kk <Nikon> | 電気光学的光制御素子 |
| NL8602767A (nl) * | 1986-10-31 | 1988-05-16 | Gantax Nv | Organisch zuuranhydride, alsmede farmaceutisch preparaat op basis van een prodrug. |
| CA2243402A1 (en) * | 1997-07-22 | 1999-01-22 | Hideo Suwa | Process for producing maleic anhydride |
| JP4822548B2 (ja) * | 2007-04-23 | 2011-11-24 | レーザーテック株式会社 | 欠陥検査装置 |
| CN109293723A (zh) * | 2018-09-21 | 2019-02-01 | 山东斯瑞生物医药有限公司 | 雌甾-4,9-二烯-3,17-二酮的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1255101A (fr) * | 1960-01-22 | 1961-03-03 | Chimiotherapie Lab Franc | Procédé d'alcoylation d'intermédiaires de la synthèse de 10-alcoyl 19-nor stéroïdes |
| US3117979A (en) * | 1960-01-22 | 1964-01-14 | Roussel Uclaf | Esters of 10beta-substituted 4, 5-seco-delta9(11)-19-nor-androstene-17beta-ol-3, 5-dines, intermediates and process |
| NL126395C (en, 2012) * | 1962-03-06 | |||
| NL130550C (en, 2012) * | 1966-05-26 | |||
| US3984473A (en) * | 1968-10-04 | 1976-10-05 | Hoffmann-La Roche Inc. | Stereospecific total steroidal synthesis via substituted C/D-trans indanones |
| US3686215A (en) * | 1969-03-27 | 1972-08-22 | Syntex Corp | Production of 5,6,7,7a-tetrahydroindan-5-ones |
| SE367181B (en, 2012) * | 1969-05-14 | 1974-05-20 | Takeda Chemical Industries Ltd | |
| US3813417A (en) * | 1970-08-26 | 1974-05-28 | Hoffmann La Roche | Cycloalkyl(f)(l)benzopyrans |
| DE2228474A1 (de) * | 1972-06-08 | 1973-12-20 | Schering Ag | Neue bicycloalkan-derivate |
-
1978
- 1978-06-19 US US05/916,443 patent/US4158012A/en not_active Expired - Lifetime
-
1979
- 1979-06-13 DK DK246479A patent/DK246479A/da not_active Application Discontinuation
- 1979-06-14 DD DD79213624A patent/DD144269A5/de not_active IP Right Cessation
- 1979-06-14 CS CS794117A patent/CS212220B2/cs unknown
- 1979-06-14 CS CS794430A patent/CS212221B2/cs unknown
- 1979-06-15 EP EP79301154A patent/EP0006355B1/en not_active Expired
- 1979-06-15 AT AT79301154T patent/ATE7600T1/de not_active IP Right Cessation
- 1979-06-15 DE DE7979301154T patent/DE2967004D1/de not_active Expired
- 1979-06-18 PL PL1979216413A patent/PL118827B1/pl unknown
- 1979-06-18 HU HU823085A patent/HU186974B/hu not_active IP Right Cessation
- 1979-06-18 ES ES481650A patent/ES481650A1/es not_active Expired
- 1979-06-18 PL PL1979227203A patent/PL123780B1/pl unknown
- 1979-06-18 JP JP7573279A patent/JPS552675A/ja active Granted
- 1979-06-18 YU YU1427/79A patent/YU41160B/xx unknown
- 1979-06-18 HU HU79SI1701A patent/HU181503B/hu not_active IP Right Cessation
- 1979-06-18 SU SU792776318A patent/SU999977A3/ru active
-
1987
- 1987-05-22 SG SG382/87A patent/SG38287G/en unknown
- 1987-12-17 HK HK967/87A patent/HK96787A/xx unknown
- 1987-12-30 MY MY665/87A patent/MY8700665A/xx unknown
-
1988
- 1988-06-15 JP JP63145943A patent/JPS6425747A/ja active Granted
- 1988-06-15 JP JP63145942A patent/JPS6425772A/ja active Granted
-
1991
- 1991-07-02 DK DK129491A patent/DK129491A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SU999977A3 (ru) | 1983-02-23 |
| HU181503B (en) | 1983-10-28 |
| PL123780B1 (en) | 1982-11-30 |
| PL216413A1 (en, 2012) | 1980-03-24 |
| EP0006355B1 (en) | 1984-05-23 |
| MY8700665A (en) | 1987-12-31 |
| CS212220B2 (en) | 1982-03-26 |
| DK129491D0 (da) | 1991-07-02 |
| DK246479A (da) | 1979-12-20 |
| HK96787A (en) | 1987-12-24 |
| DK129491A (da) | 1991-07-02 |
| ES481650A1 (es) | 1980-04-16 |
| DD144269A5 (de) | 1980-10-08 |
| US4158012A (en) | 1979-06-12 |
| EP0006355A1 (en) | 1980-01-09 |
| JPH0316333B2 (en, 2012) | 1991-03-05 |
| DE2967004D1 (en) | 1984-06-28 |
| YU41160B (en) | 1986-12-31 |
| JPS6425747A (en) | 1989-01-27 |
| CS212221B2 (en) | 1982-03-26 |
| SG38287G (en) | 1987-07-24 |
| YU142779A (en) | 1983-02-28 |
| JPS645034B2 (en, 2012) | 1989-01-27 |
| ATE7600T1 (de) | 1984-06-15 |
| JPH0129792B2 (en, 2012) | 1989-06-14 |
| JPS6425772A (en) | 1989-01-27 |
| JPS552675A (en) | 1980-01-10 |
| PL118827B1 (en) | 1981-10-31 |
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