NO119416B - - Google Patents
Download PDFInfo
- Publication number
- NO119416B NO119416B NO165461A NO16546166A NO119416B NO 119416 B NO119416 B NO 119416B NO 165461 A NO165461 A NO 165461A NO 16546166 A NO16546166 A NO 16546166A NO 119416 B NO119416 B NO 119416B
- Authority
- NO
- Norway
- Prior art keywords
- demethyl
- epipodophyllotoxin
- podophyllotoxin
- chloroform
- compound
- Prior art date
Links
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229960001237 podophyllotoxin Drugs 0.000 claims description 4
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 210000003855 cell nucleus Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006345 epimerization reaction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FOVRGQUEGRCWPD-UHFFFAOYSA-N (5aR)-9t-beta-D-Glucopyranosyloxy-5t-(4-hydroxy-3,5-dimethoxy-phenyl)-(5ar,8at)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-on Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(OC3C(C(O)C(O)C(CO)O3)O)C3C2C(OC3)=O)=C1 FOVRGQUEGRCWPD-UHFFFAOYSA-N 0.000 description 1
- NXVJTGLCCSFGAT-QNDDJFOYSA-N (5r,5ar,8ar,9r)-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NXVJTGLCCSFGAT-QNDDJFOYSA-N 0.000 description 1
- YVCVYCSAAZQOJI-JHQYFNNDSA-N 4'-demethylepipodophyllotoxin Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YVCVYCSAAZQOJI-JHQYFNNDSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 229940045696 antineoplastic drug podophyllotoxin derivative Drugs 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 201000006512 mast cell neoplasm Diseases 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical class COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
- 239000003600 podophyllotoxin derivative Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1050964A CH454169A (de) | 1964-08-12 | 1964-08-12 | Verfahren zur Herstellung von neuen Podophyllotoxin-Derivaten |
| CH788865 | 1965-06-04 | ||
| CH819965 | 1965-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119416B true NO119416B (da) | 1970-05-19 |
Family
ID=27175878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO165461A NO119416B (da) | 1964-08-12 | 1966-11-04 |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT268540B (da) |
| BE (1) | BE668122A (da) |
| BR (1) | BR6572038D0 (da) |
| CH (1) | CH454169A (da) |
| DE (1) | DE1518324A1 (da) |
| DK (3) | DK111362B (da) |
| ES (3) | ES316314A1 (da) |
| FI (1) | FI44410B (da) |
| FR (2) | FR1468767A (da) |
| GB (1) | GB1114123A (da) |
| IL (1) | IL24135A (da) |
| NL (1) | NL6510414A (da) |
| NO (1) | NO119416B (da) |
| OA (1) | OA01792A (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4024148B2 (ja) * | 2000-11-20 | 2007-12-19 | ソンベ キム | 新規な４’−デメチル−４’−ｏ−置換−１−デオキシポドフィロトキシン誘導体及びその幾何異性体、その製造方法及びそれを含んでなる抗癌剤組成物 |
| US7342114B2 (en) * | 2003-07-01 | 2008-03-11 | California Pacific Medical Center | Podophyllotoxin derivatives |
| JP6550538B2 (ja) | 2015-10-27 | 2019-07-24 | カリフォルニア パシフィック メディカル センター | ポドフィロトキシン誘導体およびそれらの使用 |
| US10087194B2 (en) | 2015-10-27 | 2018-10-02 | California Pacific Medical Center | Podophyllotoxin derivatives and their use |
-
1964
- 1964-08-12 CH CH1050964A patent/CH454169A/de unknown
-
1965
- 1965-07-30 GB GB32730/65A patent/GB1114123A/en not_active Expired
- 1965-08-06 DE DE19651518324 patent/DE1518324A1/de active Pending
- 1965-08-10 FR FR27816A patent/FR1468767A/fr not_active Expired
- 1965-08-10 NL NL6510414A patent/NL6510414A/xx unknown
- 1965-08-10 ES ES0316314A patent/ES316314A1/es not_active Expired
- 1965-08-10 BE BE668122D patent/BE668122A/xx unknown
- 1965-08-11 IL IL24135A patent/IL24135A/xx unknown
- 1965-08-11 OA OA52144A patent/OA01792A/xx unknown
- 1965-08-11 FI FI1939/65A patent/FI44410B/fi active
- 1965-08-11 AT AT823567A patent/AT268540B/de active
- 1965-08-11 BR BR172038/65A patent/BR6572038D0/pt unknown
- 1965-10-14 ES ES0318461A patent/ES318461A1/es not_active Expired
- 1965-10-14 ES ES0318460A patent/ES318460A1/es not_active Expired
- 1965-11-09 FR FR37802A patent/FR4867M/fr not_active Expired
-
1966
- 1966-09-21 DK DK490666AA patent/DK111362B/da unknown
- 1966-09-21 DK DK490566AA patent/DK113368B/da unknown
- 1966-11-04 NO NO165461A patent/NO119416B/no unknown
-
1968
- 1968-03-14 DK DK108468AA patent/DK116294B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH454169A (de) | 1968-04-15 |
| ES316314A1 (es) | 1966-04-16 |
| GB1114123A (en) | 1968-05-15 |
| AT268540B (de) | 1969-02-10 |
| BR6572038D0 (pt) | 1973-08-16 |
| OA01792A (fr) | 1970-01-14 |
| DK116294B (da) | 1969-12-29 |
| DK113368B (da) | 1969-03-17 |
| ES318460A1 (es) | 1966-04-01 |
| NL6510414A (da) | 1966-02-14 |
| FR1468767A (fr) | 1967-02-10 |
| FR4867M (da) | 1967-02-27 |
| BE668122A (da) | 1966-02-10 |
| FI44410B (da) | 1971-08-02 |
| DE1518324A1 (de) | 1969-08-21 |
| DK111362B (da) | 1968-08-05 |
| ES318461A1 (es) | 1966-06-01 |
| IL24135A (en) | 1969-02-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO160261B (no) | Analogifremgangsmaate for fremstilling av den terapeutisk aktive forbindelse n-metyl-11-aza-10-deokso-10-dihydroerytromycin a. | |
| CA1103262A (en) | Process for preparing 1,4:3,6-dianhydro-d-glucitol 2- nitrate | |
| US2857385A (en) | Preparation op pentacyclic lactones | |
| NO165461B (no) | Forankringsvekt for undervanns roerledninger. | |
| CA2243592C (en) | Method of production of lovastatin | |
| NO119416B (da) | ||
| NO162023B (no) | Fremgangsmaate til fremstilling av antracyklinderivater. | |
| NO801627L (no) | Hydroxyamino-eburnan-derivater og fremgangsmaate ved deres fremstilling | |
| US2390395A (en) | Sorbitan and process for making the same | |
| NO126320B (da) | ||
| NO164794B (no) | Tilholderlaas. | |
| US3426017A (en) | Sulfonylurea compounds | |
| US3583992A (en) | 1-methyl-d-lysergic acid-dihydroxy-alkyl-amides | |
| NO127920B (da) | ||
| SU1207396A3 (ru) | Способ выделени винкристина | |
| US2265207A (en) | D-lysergic acid - d - l-bjtdroxybutyl | |
| US2912436A (en) | Brominated alkaloids | |
| US2728763A (en) | Preparation of benzimidazole glycosides | |
| DE3224213A1 (de) | Substituierte pyrrolo-(2,1-b)-chinazoline und pyrido-(2,1-b)-chinazoline, verfahren zur herstellung derselben sowie pharmazeutische praeparate, die diese verbindungen enthalten | |
| US2802006A (en) | Esters of the yohimbe alkaloids | |
| US2040145A (en) | Beta-methylcholine derivatives and salts and processes for their production | |
| NO118262B (da) | ||
| Frush et al. | Amides of glucuronic, galacturonic, and mannuronic acids | |
| US3551432A (en) | 1-loweralkanoyl-nipecotonitriles | |
| CN110105361B (zh) | 一种Evodiakine及其衍生物的制备方法 |