CA1041488A - Process for the preparation of analogues of daunomycin - Google Patents
Process for the preparation of analogues of daunomycinInfo
- Publication number
- CA1041488A CA1041488A CA229,023A CA229023A CA1041488A CA 1041488 A CA1041488 A CA 1041488A CA 229023 A CA229023 A CA 229023A CA 1041488 A CA1041488 A CA 1041488A
- Authority
- CA
- Canada
- Prior art keywords
- configuration
- alpha
- beta
- daunosaminyl
- anomers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical class 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 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract 3
- YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical class C1[C@@](O)(C(C)=O)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-MQJDWESPSA-N 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 6
- 229940101209 mercuric oxide Drugs 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 claims description 2
- 229930182470 glycoside Natural products 0.000 claims 2
- 150000002338 glycosides Chemical class 0.000 claims 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229960001701 chloroform Drugs 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000460 chlorine Chemical group 0.000 abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 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 description 18
- ZUFQFGSMHXKORU-UHFFFAOYSA-N 9-acetyl-6,7,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1C(O)CC(C(=O)C)(O)CC1=C2O ZUFQFGSMHXKORU-UHFFFAOYSA-N 0.000 description 13
- 229940009456 adriamycin Drugs 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000713862 Moloney murine sarcoma virus Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000002513 implantation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZUFQFGSMHXKORU-YUNKPMOVSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](C(=O)C)(O)CC1=C2O ZUFQFGSMHXKORU-YUNKPMOVSA-N 0.000 description 2
- 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 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000003833 cell viability Effects 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000003147 glycosyl group Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BBMKQGIZNKEDOX-UHFFFAOYSA-N D-Acosamin Natural products CC1OC(O)CC(N)C1O BBMKQGIZNKEDOX-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- 241000630329 Scomberesox saurus saurus Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23B—TURNING; BORING
- B23B3/00—General-purpose turning-machines or devices, e.g. centre lathes with feed rod and lead screw; Sets of turning-machines
- B23B3/16—Turret lathes for turning individually-chucked workpieces
- B23B3/167—Turret lathes for turning individually-chucked workpieces lathe with two or more toolslides carrying turrets
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Turning (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2608474A GB1444301A (en) | 1974-06-12 | 1974-06-12 | Turning machines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1041488A true CA1041488A (en) | 1978-10-31 |
Family
ID=10238100
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA229,023A Expired CA1041488A (en) | 1974-06-12 | 1975-06-10 | Process for the preparation of analogues of daunomycin |
| CA229,122A Expired CA1020736A (en) | 1974-06-12 | 1975-06-11 | Machine tools |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA229,122A Expired CA1020736A (en) | 1974-06-12 | 1975-06-11 | Machine tools |
Country Status (13)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6087340A (en) * | 1985-08-02 | 2000-07-11 | Pharmacia & Upjohn, Inc. | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| US6107285A (en) * | 1985-08-02 | 2000-08-22 | Pharmacia & Upjohn Company | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2340790A1 (fr) * | 1976-02-16 | 1977-09-09 | Churchill Charles Ltd | Machine-outil perfectionnee |
| JPS5333484A (en) * | 1976-09-10 | 1978-03-29 | Okuma Mach Works Ltd | Interference preventive system of machine tool having plurality of movable members |
| AT360814B (de) * | 1977-04-26 | 1981-02-10 | Monforts Fa A | Drehmaschine |
| FR2403140A2 (fr) * | 1977-09-19 | 1979-04-13 | Cri Dan | Tour pour l'usinage de pieces creuses |
| JPS555241A (en) * | 1978-06-26 | 1980-01-16 | Tsugami Corp | Subsidary tool post of automatic turret lathe |
| WO1980000933A1 (en) * | 1978-11-02 | 1980-05-15 | Kyodo Shaft Co Ltd | Machine tool for cutting opposite ends of workpieces |
| FR2467034A1 (fr) * | 1979-10-15 | 1981-04-17 | Cit Alcatel | Centre d'usinage a commande numerique et a tourelles interchangeables |
| CH636543A5 (fr) * | 1980-07-16 | 1983-06-15 | Tarex Sa | Machine-outil comprenant deux broches coaxiales opposees. |
| JPS5759015U (enrdf_load_stackoverflow) * | 1980-09-22 | 1982-04-07 | ||
| DE3136017C1 (de) * | 1981-09-11 | 1983-03-10 | Edouard Dubied & Cie. S.A., 2108 Couvet, Neuchâtel | Drehmaschine |
| DE3239314C2 (de) * | 1982-10-23 | 1993-12-02 | Index Werke Kg Hahn & Tessky | 4-Achsen-Drehmaschine |
| US4506569A (en) * | 1982-11-02 | 1985-03-26 | Hardinge Brothers, Inc. | Multiple axis slant bed machine |
| DE3304372A1 (de) * | 1983-02-09 | 1984-08-09 | Heyligenstaedt & Co, Werkzeugmaschinenfabrik Gmbh, 6300 Giessen | Nc-schraegbettdrehmaschine |
| DE3320655A1 (de) * | 1983-06-08 | 1984-12-13 | Heyligenstaedt & Co, Werkzeugmaschinenfabrik Gmbh, 6300 Giessen | Frontdrehmaschine |
| JPS60167603U (ja) * | 1984-04-13 | 1985-11-07 | 株式会社 森精機製作所 | 旋盤 |
| JPS61103704A (ja) * | 1984-10-26 | 1986-05-22 | Citizen Watch Co Ltd | 自動旋盤 |
| GB2166678A (en) * | 1984-11-09 | 1986-05-14 | Gardner R F | Multi turret lathe |
| PL147217B1 (en) * | 1985-02-08 | 1989-05-31 | Ct Badawczo Konst Obrabiarek | Machine tool |
| DE3532924A1 (de) * | 1985-09-14 | 1987-03-26 | Gildemeister Ag | Werkzeugwechselvorrichtung |
| DE3802492A1 (de) * | 1988-01-28 | 1989-08-03 | Monforts Gmbh & Co A | Drehmaschine |
| DE102008009559B3 (de) * | 2008-02-16 | 2009-05-07 | Gildemeister Drehmaschinen Gmbh | Werkzeugrevolvereinheit |
| CN103659404A (zh) * | 2013-11-26 | 2014-03-26 | 山西浩业通用设备有限公司 | 卧式车床增加回转直径装置 |
| CN107598189A (zh) * | 2017-10-20 | 2018-01-19 | 浙江柏思达齿轮有限公司 | 一种车内外圆一体机床及其加工方法 |
| CN111889708B (zh) * | 2020-07-28 | 2021-09-17 | 于都海瑞密封防腐科技有限公司 | 一种o形密封圈加工装置及方法 |
| CN115415556B (zh) * | 2022-08-30 | 2025-07-15 | 浙江大学 | 一种聚四氟乙烯管件的车削加工装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1477170A1 (de) * | 1965-02-18 | 1969-05-08 | Krupp Gmbh | Numerisch gesteuerte Drehmaschine |
| DE2128642C3 (de) * | 1971-06-09 | 1979-05-03 | Gildemeister Ag, 4800 Bielefeld | Werkzeugrevolveranordnung an Revolverdrehmaschinen |
-
1974
- 1974-06-12 GB GB2608474A patent/GB1444301A/en not_active Expired
-
1975
- 1975-05-23 JP JP6113375A patent/JPS5192A/ja active Pending
- 1975-05-28 DE DE19752523751 patent/DE2523751C2/de not_active Expired
- 1975-05-30 CH CH702575A patent/CH595168A5/xx not_active IP Right Cessation
- 1975-05-30 SE SE7506207A patent/SE412714B/xx unknown
- 1975-06-05 IT IT4992675A patent/IT1035948B/it active
- 1975-06-09 NL NL7506833A patent/NL7506833A/xx unknown
- 1975-06-10 CA CA229,023A patent/CA1041488A/en not_active Expired
- 1975-06-10 ES ES1975213045U patent/ES213045Y/es not_active Expired
- 1975-06-10 DD DD18655575A patent/DD121042A5/xx unknown
- 1975-06-11 FR FR7518204A patent/FR2274385A1/fr not_active Withdrawn
- 1975-06-11 CA CA229,122A patent/CA1020736A/en not_active Expired
- 1975-06-11 SU SU752143590A patent/SU661997A3/ru active
- 1975-06-12 AT AT450975A patent/AT341856B/de not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6087340A (en) * | 1985-08-02 | 2000-07-11 | Pharmacia & Upjohn, Inc. | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| US6107285A (en) * | 1985-08-02 | 2000-08-22 | Pharmacia & Upjohn Company | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| US6284738B1 (en) | 1985-08-02 | 2001-09-04 | Pharmacia & Upjohn Company | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| US7005421B2 (en) | 1985-08-02 | 2006-02-28 | Pharmacia & Upjohn Company | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1035948B (it) | 1979-10-20 |
| SE7506207L (sv) | 1975-12-15 |
| ATA450975A (de) | 1977-06-15 |
| CH595168A5 (enrdf_load_stackoverflow) | 1978-01-31 |
| FR2274385A1 (fr) | 1976-01-09 |
| ES213045Y (es) | 1976-11-01 |
| SE412714B (sv) | 1980-03-17 |
| DD121042A5 (enrdf_load_stackoverflow) | 1976-07-12 |
| GB1444301A (en) | 1976-07-28 |
| JPS5192A (ja) | 1976-01-05 |
| SU661997A3 (ru) | 1979-05-05 |
| AT341856B (de) | 1978-03-10 |
| DE2523751C2 (de) | 1983-12-15 |
| CA1020736A (en) | 1977-11-15 |
| DE2523751A1 (de) | 1976-01-02 |
| NL7506833A (nl) | 1975-12-16 |
| ES213045U (es) | 1976-06-16 |
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