SE443565B - Tetrahydropyranylderivat av antracyklinglykosider - Google Patents
Tetrahydropyranylderivat av antracyklinglykosiderInfo
- Publication number
- SE443565B SE443565B SE7808304A SE7808304A SE443565B SE 443565 B SE443565 B SE 443565B SE 7808304 A SE7808304 A SE 7808304A SE 7808304 A SE7808304 A SE 7808304A SE 443565 B SE443565 B SE 443565B
- Authority
- SE
- Sweden
- Prior art keywords
- tetrahydropyranyl
- acid
- adriamycin
- group
- compounds
- Prior art date
Links
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 33
- 229940009456 adriamycin Drugs 0.000 claims description 30
- 231100000252 nontoxic Toxicity 0.000 claims description 20
- 230000003000 nontoxic effect Effects 0.000 claims description 20
- -1 tetrahydropyran-2-yl-oxy group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229930182470 glycoside Natural products 0.000 claims description 12
- 150000002338 glycosides Chemical class 0.000 claims description 11
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 17
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- 239000000243 solution Substances 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
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- 238000002360 preparation method Methods 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
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- 230000002401 inhibitory effect Effects 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
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- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 3
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
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- 238000003113 dilution method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229940035637 spectrum-4 Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9434877A JPS5430146A (en) | 1977-08-05 | 1977-08-05 | Novel anthracycline derivatives and their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7808304L SE7808304L (sv) | 1979-02-06 |
| SE443565B true SE443565B (sv) | 1986-03-03 |
Family
ID=14107771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7808304A SE443565B (sv) | 1977-08-05 | 1978-08-01 | Tetrahydropyranylderivat av antracyklinglykosider |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5430146A (da) |
| AT (1) | AT361622B (da) |
| AU (1) | AU510946B2 (da) |
| BE (1) | BE869395A (da) |
| CA (1) | CA1120925A (da) |
| DE (1) | DE2831579C3 (da) |
| DK (1) | DK152677C (da) |
| ES (1) | ES472306A1 (da) |
| FI (1) | FI63420C (da) |
| FR (1) | FR2399439A1 (da) |
| GB (1) | GB2002754B (da) |
| GR (1) | GR63951B (da) |
| HK (1) | HK18683A (da) |
| IE (1) | IE47252B1 (da) |
| IT (1) | IT1160574B (da) |
| NL (1) | NL174147C (da) |
| SE (1) | SE443565B (da) |
| SG (1) | SG5383G (da) |
| ZA (1) | ZA784033B (da) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK160616C (da) * | 1979-02-03 | 1991-09-02 | Zaidan Hojin Biseibutsu | Fremgangsmaade til fremstilling af anthracyclinderivater eller syreadditionssalte deraf |
| JPS56156300A (en) * | 1980-04-26 | 1981-12-02 | Microbial Chem Res Found | Novel preparative method of anthracyclin derivative |
| JPS6016998A (ja) * | 1983-07-07 | 1985-01-28 | Microbial Chem Res Found | アントラサイクリン誘導体の製造方法 |
| JPS6083171U (ja) * | 1983-11-15 | 1985-06-08 | タキゲン製造株式会社 | 蝶番 |
| JPS63227599A (ja) * | 1987-03-14 | 1988-09-21 | Kirin Brewery Co Ltd | アンスラサイクリン化合物およびその用途 |
| DE19544532C2 (de) * | 1995-11-29 | 1997-12-11 | Pharma Dynamics Gmbh | Verfahren zum Herstellen eines Doxorubicin-Lyophilisats |
| KR19990084528A (ko) * | 1998-05-07 | 1999-12-06 | 박상철 | 신규 안트라사이클린 유도체 및 제조방법 |
| GB2530001B (en) | 2014-06-17 | 2019-01-16 | Gw Pharma Ltd | Use of cannabidiol in the reduction of convulsive seizure frequency in treatment-resistant epilepsy |
| GB2531282A (en) | 2014-10-14 | 2016-04-20 | Gw Pharma Ltd | Use of cannabinoids in the treatment of epilepsy |
| GB2539472A (en) | 2015-06-17 | 2016-12-21 | Gw Res Ltd | Use of cannabinoids in the treatment of epilepsy |
| GB2568929A (en) | 2017-12-01 | 2019-06-05 | Gw Res Ltd | Use of cannabinoids in the treatment of epilepsy |
| GB201806953D0 (en) | 2018-04-27 | 2018-06-13 | Gw Res Ltd | Cannabidiol Preparations |
-
1977
- 1977-08-05 JP JP9434877A patent/JPS5430146A/ja active Granted
-
1978
- 1978-07-14 ZA ZA00784033A patent/ZA784033B/xx unknown
- 1978-07-15 GR GR56794A patent/GR63951B/el unknown
- 1978-07-18 DE DE2831579A patent/DE2831579C3/de not_active Expired
- 1978-07-26 NL NLAANVRAGE7807906,A patent/NL174147C/xx not_active IP Right Cessation
- 1978-07-27 GB GB7831324A patent/GB2002754B/en not_active Expired
- 1978-07-28 AU AU38446/78A patent/AU510946B2/en not_active Expired
- 1978-07-31 BE BE189604A patent/BE869395A/xx not_active IP Right Cessation
- 1978-08-01 CA CA000308532A patent/CA1120925A/en not_active Expired
- 1978-08-01 SE SE7808304A patent/SE443565B/sv not_active IP Right Cessation
- 1978-08-01 IE IE1566/78A patent/IE47252B1/en not_active IP Right Cessation
- 1978-08-02 FI FI782388A patent/FI63420C/fi not_active IP Right Cessation
- 1978-08-02 FR FR7822859A patent/FR2399439A1/fr active Granted
- 1978-08-02 AT AT561278A patent/AT361622B/de not_active IP Right Cessation
- 1978-08-02 ES ES472306A patent/ES472306A1/es not_active Expired
- 1978-08-02 DK DK343878A patent/DK152677C/da active
- 1978-08-03 IT IT68847/78A patent/IT1160574B/it active
-
1983
- 1983-02-05 SG SG53/83A patent/SG5383G/en unknown
- 1983-06-02 HK HK186/83A patent/HK18683A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT361622B (de) | 1981-03-25 |
| NL7807906A (nl) | 1979-02-07 |
| IT7868847A0 (it) | 1978-08-03 |
| FR2399439B1 (da) | 1981-07-17 |
| ATA561278A (de) | 1980-08-15 |
| IE781566L (en) | 1979-02-05 |
| DE2831579A1 (de) | 1979-02-15 |
| HK18683A (en) | 1983-06-10 |
| JPS5430146A (en) | 1979-03-06 |
| GR63951B (en) | 1980-01-16 |
| SE7808304L (sv) | 1979-02-06 |
| DK152677C (da) | 1988-10-24 |
| FI782388A7 (fi) | 1979-02-06 |
| JPS5647194B2 (da) | 1981-11-07 |
| NL174147C (nl) | 1984-05-01 |
| ZA784033B (en) | 1979-07-25 |
| NL174147B (nl) | 1983-12-01 |
| GB2002754A (en) | 1979-02-28 |
| DK152677B (da) | 1988-04-11 |
| IE47252B1 (en) | 1984-02-08 |
| IT1160574B (it) | 1987-03-11 |
| DE2831579B2 (de) | 1980-01-24 |
| FI63420C (fi) | 1983-06-10 |
| SG5383G (en) | 1983-09-09 |
| AU510946B2 (en) | 1980-07-24 |
| AU3844678A (en) | 1980-01-31 |
| ES472306A1 (es) | 1979-10-01 |
| GB2002754B (en) | 1982-02-10 |
| CA1120925A (en) | 1982-03-30 |
| DE2831579C3 (de) | 1980-09-18 |
| FI63420B (fi) | 1983-02-28 |
| BE869395A (fr) | 1978-11-16 |
| DK343878A (da) | 1979-02-06 |
| FR2399439A1 (fr) | 1979-03-02 |
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