SU578007A3 - Способ получени производных просцилларидина - Google Patents
Способ получени производных просцилларидинаInfo
- Publication number
- SU578007A3 SU578007A3 SU7502162229A SU2162229A SU578007A3 SU 578007 A3 SU578007 A3 SU 578007A3 SU 7502162229 A SU7502162229 A SU 7502162229A SU 2162229 A SU2162229 A SU 2162229A SU 578007 A3 SU578007 A3 SU 578007A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ether
- derivatives
- mmol
- ethyl acetate
- proscillaridine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- MYEJFUXQJGHEQK-ALRJYLEOSA-N Proscillaridin Chemical class O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C=C2CC[C@H]3[C@@]4(O)CC[C@H](C5=COC(=O)C=C5)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 MYEJFUXQJGHEQK-ALRJYLEOSA-N 0.000 title 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 6
- FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- -1 benzyl ester Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- OKRROXQXGNEUSS-UHFFFAOYSA-N 1h-imidazol-1-ium-1-carboxylate Chemical compound OC(=O)N1C=CN=C1 OKRROXQXGNEUSS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- UAOCPXBBRCJOAV-UHFFFAOYSA-N [S].O=S=O Chemical compound [S].O=S=O UAOCPXBBRCJOAV-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
- C07J19/005—Glycosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2437693A DE2437693A1 (de) | 1974-08-05 | 1974-08-05 | Neue proscillaridinderivate und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU578007A3 true SU578007A3 (ru) | 1977-10-25 |
Family
ID=5922494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502162229A SU578007A3 (ru) | 1974-08-05 | 1975-07-25 | Способ получени производных просцилларидина |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3981992A (enExample) |
| JP (1) | JPS5139670A (enExample) |
| AT (1) | AT347045B (enExample) |
| BE (1) | BE832101A (enExample) |
| CA (1) | CA1057737A (enExample) |
| CS (1) | CS181788B2 (enExample) |
| DD (1) | DD124603A5 (enExample) |
| DE (1) | DE2437693A1 (enExample) |
| DK (1) | DK136219C (enExample) |
| ES (3) | ES440004A1 (enExample) |
| FI (1) | FI752187A7 (enExample) |
| FR (1) | FR2281126A1 (enExample) |
| GB (1) | GB1511172A (enExample) |
| HU (1) | HU170944B (enExample) |
| IL (1) | IL47861A (enExample) |
| LU (1) | LU73140A1 (enExample) |
| NL (1) | NL7509250A (enExample) |
| NO (1) | NO140189C (enExample) |
| NZ (1) | NZ178280A (enExample) |
| PH (1) | PH11776A (enExample) |
| PL (1) | PL100061B1 (enExample) |
| RO (1) | RO75385A (enExample) |
| SE (1) | SE7508790L (enExample) |
| SU (1) | SU578007A3 (enExample) |
| ZA (1) | ZA754998B (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU33975B (en) * | 1969-01-09 | 1978-09-08 | Knol Ag Chemische Fabriken | Process for preparing bufatrienolide-rhamnoside-acylates |
-
1974
- 1974-08-05 DE DE2437693A patent/DE2437693A1/de not_active Withdrawn
-
1975
- 1975-07-11 AT AT535675A patent/AT347045B/de not_active IP Right Cessation
- 1975-07-25 SU SU7502162229A patent/SU578007A3/ru active
- 1975-07-30 PH PH17428A patent/PH11776A/en unknown
- 1975-07-30 US US05/600,433 patent/US3981992A/en not_active Expired - Lifetime
- 1975-07-30 JP JP50092994A patent/JPS5139670A/ja active Pending
- 1975-07-30 RO RO7583018A patent/RO75385A/ro unknown
- 1975-07-31 FI FI752187A patent/FI752187A7/fi not_active Application Discontinuation
- 1975-08-01 CA CA232,734A patent/CA1057737A/en not_active Expired
- 1975-08-04 NZ NZ178280A patent/NZ178280A/xx unknown
- 1975-08-04 ZA ZA754998A patent/ZA754998B/xx unknown
- 1975-08-04 ES ES440004A patent/ES440004A1/es not_active Expired
- 1975-08-04 NL NL7509250A patent/NL7509250A/xx not_active Application Discontinuation
- 1975-08-04 SE SE7508790A patent/SE7508790L/xx unknown
- 1975-08-04 LU LU73140A patent/LU73140A1/xx unknown
- 1975-08-04 CS CS7500005427A patent/CS181788B2/cs unknown
- 1975-08-04 DD DD187670A patent/DD124603A5/xx unknown
- 1975-08-04 PL PL1975182533A patent/PL100061B1/pl unknown
- 1975-08-04 HU HU75BO00001567A patent/HU170944B/hu unknown
- 1975-08-04 BE BE158926A patent/BE832101A/xx unknown
- 1975-08-04 IL IL47861A patent/IL47861A/xx unknown
- 1975-08-04 GB GB32574/75A patent/GB1511172A/en not_active Expired
- 1975-08-04 DK DK353075A patent/DK136219C/da active
- 1975-08-04 NO NO752733A patent/NO140189C/no unknown
- 1975-08-05 FR FR7524401A patent/FR2281126A1/fr active Granted
-
1976
- 1976-09-30 ES ES451976A patent/ES451976A1/es not_active Expired
- 1976-09-30 ES ES451977A patent/ES451977A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES451976A1 (es) | 1977-09-16 |
| PH11776A (en) | 1978-07-05 |
| SE7508790L (sv) | 1976-02-06 |
| NO752733L (enExample) | 1976-02-06 |
| FI752187A7 (enExample) | 1976-02-06 |
| PL100061B1 (pl) | 1978-08-31 |
| NO140189C (no) | 1979-07-18 |
| IL47861A (en) | 1979-05-31 |
| ZA754998B (en) | 1977-04-27 |
| DD124603A5 (enExample) | 1977-03-02 |
| RO75385A (ro) | 1980-11-30 |
| NZ178280A (en) | 1978-03-06 |
| CS181788B2 (en) | 1978-03-31 |
| DK136219C (da) | 1978-02-06 |
| DK136219B (da) | 1977-09-05 |
| DE2437693A1 (de) | 1976-02-26 |
| LU73140A1 (enExample) | 1977-04-13 |
| FR2281126A1 (fr) | 1976-03-05 |
| CA1057737A (en) | 1979-07-03 |
| JPS5139670A (enExample) | 1976-04-02 |
| BE832101A (fr) | 1976-02-04 |
| IL47861A0 (en) | 1975-11-25 |
| AT347045B (de) | 1978-12-11 |
| ES451977A1 (es) | 1977-09-16 |
| GB1511172A (en) | 1978-05-17 |
| US3981992A (en) | 1976-09-21 |
| AU8364475A (en) | 1977-02-10 |
| ATA535675A (de) | 1978-04-15 |
| FR2281126B1 (enExample) | 1978-12-01 |
| NL7509250A (nl) | 1976-02-09 |
| ES440004A1 (es) | 1977-02-16 |
| HU170944B (hu) | 1977-10-28 |
| DK353075A (da) | 1976-02-06 |
| NO140189B (no) | 1979-04-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wenkert et al. | Studies of 2, 2'-bipyridyl N, N'-dioxides | |
| JP4332218B2 (ja) | ５−ｏ−デオサミニル−６−ｏ−メチルエリスロノライドａの新規な誘導体、それらの製造法及びそれらの生物学的活性物質の製造への使用 | |
| SU613724A3 (ru) | Способ получени 8-тиометил-эрголинов или их солей | |
| Taylor et al. | Structure and stereochemistry of some 1, 2-disubstituted mitosenes from solvolysis of mitomycin C and Mitomycin A | |
| RU2198875C2 (ru) | Способы получения тиосемикарбазонов пиридин-2-карбоксальдегидов и промежуточных пиридин-2-карбоксальдегидов | |
| Back et al. | Studies of enamidic. DELTA. 5-4-azasteroidal selenoxides: preparation, Pummerer reactions, configurational stability, and conversion to carbinol amides | |
| JP2562935B2 (ja) | 抗腫瘍性物質ｓｆ２５８２誘導体 | |
| CN114163436A (zh) | 一种含吲哚嗪的二芳基甲烷衍生物及其制备方法和应用 | |
| SU578007A3 (ru) | Способ получени производных просцилларидина | |
| Mukaiyama et al. | Phosphorylation of alcohols and phosphates by oxidation-reduction condensation | |
| CN109734713B (zh) | 一种3-亚胺基咪唑并[1,2-a]吡啶化合物 | |
| SU656526A3 (ru) | Способ получени производных изомеров цефалоспорановой кислоты | |
| CN116265440B (zh) | 一种水杨酮拼接吡啶酮类化合物及其制备方法及应用 | |
| JPS63310864A (ja) | 生理活性を有する新規なアクチノニン誘導体 | |
| SU833971A1 (ru) | Способ получени 3-фенил-2-оксо- - КАРбОлиНОВ | |
| Kakehi et al. | Synthesis using allylidenedihydropyridines. 9. First preparation of thiino [3, 2-a] indolizine derivatives | |
| CN112679430B (zh) | 一种制备异喹啉酮类化合物的方法 | |
| Gataullin | Halolactonization of N-Acyl-N-(2-cyclohex-1-en-1-yl-6-methylphenyl) glycines: Towards Production of 4, 1-Benzoxazoheterocycles | |
| Ballester-Rodes et al. | N, N-Bis (2-Oxo-3-Oxazolidinyl) Phosphordiamidic Chloride (CLSPO): A New Strategy for the Ester Function Preparation | |
| JPH0931092A (ja) | ２’−３’−ジ−ｏ−アシルａｔｐの製造法 | |
| CN118440078B (zh) | 一种生物活性的苯并中氮茚衍生物的制备方法 | |
| JP3964485B2 (ja) | ニトリルの製造方法 | |
| SU1435153A3 (ru) | Способ получени сложного этилового эфира аповинкаминовой кислоты | |
| RU2785692C1 (ru) | Способ получения 1,9-(1',4'-оксатиано-4'-оксид)-1,9-дигидро-(С60-Ih)[5,6]фуллерена | |
| Di Gregorio et al. | Mono-and polyanhydride formation by reaction of 2, 2, 4, 4, 6, 6-hexachlorotriazatriphosphorine with carboxylic acid salts under mild conditions |