SU423294A3 - Способ получения производных холестана - Google Patents
Способ получения производных холестанаInfo
- Publication number
- SU423294A3 SU423294A3 SU1675380A SU1675380A SU423294A3 SU 423294 A3 SU423294 A3 SU 423294A3 SU 1675380 A SU1675380 A SU 1675380A SU 1675380 A SU1675380 A SU 1675380A SU 423294 A3 SU423294 A3 SU 423294A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- cholestane
- aza
- methyl
- solution
- cholestan
- Prior art date
Links
- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 33
- 239000000243 solution Substances 0.000 claims 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 12
- 239000000047 product Substances 0.000 claims 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 11
- -1 lithium aluminum hydride Chemical compound 0.000 claims 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 11
- 238000000034 method Methods 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 239000002244 precipitate Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 150000003951 lactams Chemical class 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- 238000001953 recrystallisation Methods 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 150000004702 methyl esters Chemical class 0.000 claims 5
- 230000007935 neutral effect Effects 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 claims 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 3
- GNGAHLNFFKCAAX-WCEAHCBLSA-N O=C1NC[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(C1)C)C)[C@H](C)CCCC(C)C Chemical compound O=C1NC[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(C1)C)C)[C@H](C)CCCC(C)C GNGAHLNFFKCAAX-WCEAHCBLSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 150000001837 cholestane derivatives Chemical class 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 3
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229910052700 potassium Inorganic materials 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- 239000011734 sodium Substances 0.000 claims 3
- 229910052708 sodium Inorganic materials 0.000 claims 3
- 229940126062 Compound A Drugs 0.000 claims 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims 2
- 229910052987 metal hydride Inorganic materials 0.000 claims 2
- 150000004681 metal hydrides Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- QKMJQIPPRJUFJI-MEJHGOECSA-N (1R,3aS,3bS,9aR,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1,2,3,3a,3b,4,7,8,9,9b,10,11-dodecahydroindeno[5,4-f]isoquinolin-6-one Chemical compound CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C(=O)NCC[C@]4(C)[C@H]3CC[C@]12C QKMJQIPPRJUFJI-MEJHGOECSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- KCMZYCFSSYXEQR-UHFFFAOYSA-N CCCC[K] Chemical compound CCCC[K] KCMZYCFSSYXEQR-UHFFFAOYSA-N 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000012298 atmosphere Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000012153 distilled water Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910000462 iron(III) oxide hydroxide Inorganic materials 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 230000001766 physiological effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 238000001665 trituration Methods 0.000 claims 1
- 150000003673 urethanes Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/005—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by nitrogen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI000395 | 1970-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU423294A3 true SU423294A3 (ru) | 1974-04-05 |
Family
ID=11000841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1675380A SU423294A3 (ru) | 1970-06-18 | 1971-06-17 | Способ получения производных холестана |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3733329A (enExample) |
| AT (1) | AT308982B (enExample) |
| BG (2) | BG18607A3 (enExample) |
| CA (1) | CA930727A (enExample) |
| DE (1) | DE2130280A1 (enExample) |
| ES (1) | ES392357A1 (enExample) |
| FR (1) | FR2100780B1 (enExample) |
| IL (1) | IL37040A0 (enExample) |
| SU (1) | SU423294A3 (enExample) |
| ZA (1) | ZA713787B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101600429A (zh) * | 2006-12-08 | 2009-12-09 | 哈多技术有限公司 | 治疗和预防传染性疾病的胆固醇胺 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB990656A (en) * | 1962-04-23 | 1965-04-28 | Searle & Co | Compounds of the androstane series |
| US3280133A (en) * | 1964-10-12 | 1966-10-18 | Searle & Co | (optionally alkylated)-2-aza-5alpha-androstan-17beta-ols and acyl derivatives thereof |
-
1971
- 1971-06-09 AT AT502071A patent/AT308982B/de active
- 1971-06-11 ZA ZA713787A patent/ZA713787B/xx unknown
- 1971-06-13 IL IL37040A patent/IL37040A0/xx unknown
- 1971-06-14 BG BG017802A patent/BG18607A3/xx unknown
- 1971-06-14 CA CA115552A patent/CA930727A/en not_active Expired
- 1971-06-14 US US00152973A patent/US3733329A/en not_active Expired - Lifetime
- 1971-06-14 BG BG019356A patent/BG19142A3/xx unknown
- 1971-06-17 ES ES392357A patent/ES392357A1/es not_active Expired
- 1971-06-17 SU SU1675380A patent/SU423294A3/ru active
- 1971-06-17 FR FR7122085A patent/FR2100780B1/fr not_active Expired
- 1971-06-18 DE DE19712130280 patent/DE2130280A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL37040A0 (en) | 1971-08-25 |
| FR2100780A1 (enExample) | 1972-03-24 |
| US3733329A (en) | 1973-05-15 |
| BG18607A3 (bg) | 1975-02-25 |
| CA930727A (en) | 1973-07-24 |
| DE2130280A1 (de) | 1971-12-23 |
| BG19142A3 (bg) | 1975-04-30 |
| ZA713787B (en) | 1972-01-26 |
| FR2100780B1 (enExample) | 1975-03-14 |
| ES392357A1 (es) | 1973-10-01 |
| AT308982B (de) | 1973-07-25 |
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