NL8900328A - Trimethylsilylethynylverbindingen, hun bereiding en hun toepassing bij het bereiden van daunomycinonderivaten. - Google Patents

Trimethylsilylethynylverbindingen, hun bereiding en hun toepassing bij het bereiden van daunomycinonderivaten. Download PDF

Info

Publication number: NL8900328A
Authority: NL; Netherlands
Prior art keywords: formula; preparation; solution; compounds; compound
Prior art date: 1989-02-10

Application number

NL8900328A

Other languages

English (en)

Dutch (nl)

Original Assignee

Pharmachemie Bv

Priority date (The priority date 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 date listed.)

1989-02-10

Filing date

1989-02-10

Publication date

1990-09-03

1989-02-10 Application filed by Pharmachemie Bv filed Critical Pharmachemie Bv

1989-02-10 Priority to NL8900328A priority Critical patent/NL8900328A/nl

1990-01-29 Priority to EP90200210A priority patent/EP0387929B1/de

1990-01-29 Priority to AT9090200210T priority patent/ATE104985T1/de

1990-01-29 Priority to DE69008396T priority patent/DE69008396D1/de

1990-02-01 Priority to CA002009095A priority patent/CA2009095A1/en

1990-02-01 Priority to US07/473,537 priority patent/US5079349A/en

1990-02-03 Priority to JP2024986A priority patent/JPH02235889A/ja

1990-09-03 Publication of NL8900328A publication Critical patent/NL8900328A/nl

Links

238000002360 preparation method Methods 0.000 title abstract description 8
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 abstract description 4
-1 TRIMETHYLSILYLETHYNYL COMPOUNDS Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 17
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 13
JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
238000006257 total synthesis reaction Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
238000003786 synthesis reaction Methods 0.000 abstract description 5
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 abstract description 4
YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound 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 abstract description 3
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 abstract description 3
YOFDHOWPGULAQF-UHFFFAOYSA-N Daunomycin-Aglycone Natural products C1C(O)(C(C)=O)CC(O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-UHFFFAOYSA-N 0.000 abstract description 3
230000015572 biosynthetic process Effects 0.000 abstract description 3
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 abstract description 2
229940009456 adriamycin Drugs 0.000 abstract 1
230000000707 stereoselective effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
238000003756 stirring Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
0 C[Si](C)(C)C#CC1(CC(CO)=CC(*)C1)O Chemical compound C[Si](C)(C)C#CC1(CC(CO)=CC(*)C1)O 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000011734 sodium Substances 0.000 description 5
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 4
239000012300 argon atmosphere Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910004664 Cerium(III) chloride Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
230000000118 anti-neoplastic effect Effects 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000007423 decrease Effects 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
238000000926 separation method Methods 0.000 description 2
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
241000222666 Boerhavia diffusa Species 0.000 description 1
OBTHZYUQAFFJPS-UHFFFAOYSA-N CC(CCC(C)c1c(c(C(C=C2)=O)c3C2=O)O)c1c3O Chemical compound CC(CCC(C)c1c(c(C(C=C2)=O)c3C2=O)O)c1c3O OBTHZYUQAFFJPS-UHFFFAOYSA-N 0.000 description 1
BQMVMHUCHZGULD-UHFFFAOYSA-N C[Si](C)(C)C#C.[Li] Chemical group C[Si](C)(C)C#C.[Li] BQMVMHUCHZGULD-UHFFFAOYSA-N 0.000 description 1
RQNVIKXOOKXAJQ-UHFFFAOYSA-N Oc(c(C(C=C1)=O)c2C1=O)ccc2O Chemical compound Oc(c(C(C=C1)=O)c2C1=O)ccc2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 1
238000010908 decantation Methods 0.000 description 1
VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002576 ketones Chemical group 0.000 description 1
ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
230000003137 locomotive effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL8900328A 1989-02-10 1989-02-10 Trimethylsilylethynylverbindingen, hun bereiding en hun toepassing bij het bereiden van daunomycinonderivaten. NL8900328A (nl)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
NL8900328A NL8900328A (nl)	1989-02-10	1989-02-10	Trimethylsilylethynylverbindingen, hun bereiding en hun toepassing bij het bereiden van daunomycinonderivaten.
EP90200210A EP0387929B1 (de)	1989-02-10	1990-01-29	Trimethylsilylacetylenverbindungen, ihre Herstellung und ihre Verwendung zur Herstellung von Daunomycinon-Derivaten
AT9090200210T ATE104985T1 (de)	1989-02-10	1990-01-29	Trimethylsilylacetylenverbindungen, ihre herstellung und ihre verwendung zur herstellung von daunomycinon-derivaten.
DE69008396T DE69008396D1 (de)	1989-02-10	1990-01-29	Trimethylsilylacetylenverbindungen, ihre Herstellung und ihre Verwendung zur Herstellung von Daunomycinon-Derivaten.
CA002009095A CA2009095A1 (en)	1989-02-10	1990-02-01	Trimethylsilyl acetylene compounds, their preparation and their use in the preparation of daunomycinone derivatives
US07/473,537 US5079349A (en)	1989-02-10	1990-02-01	Trimethylsilyl acetylene compounds, their preparation and their use in the preparation of daunomycinone derivatives
JP2024986A JPH02235889A (ja)	1989-02-10	1990-02-03	トリメチルシリルアセチレン化合物、その製造法およびそれらのダウノマイシノン誘導体製造における用途

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8900328A NL8900328A (nl)	1989-02-10	1989-02-10	Trimethylsilylethynylverbindingen, hun bereiding en hun toepassing bij het bereiden van daunomycinonderivaten.
NL8900328		1989-02-10

Publications (1)

Publication Number	Publication Date
NL8900328A true NL8900328A (nl)	1990-09-03

Family

ID=19854109

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8900328A NL8900328A (nl)	1989-02-10	1989-02-10	Trimethylsilylethynylverbindingen, hun bereiding en hun toepassing bij het bereiden van daunomycinonderivaten.

Country Status (7)

Country	Link
US (1)	US5079349A (de)
EP (1)	EP0387929B1 (de)
JP (1)	JPH02235889A (de)
AT (1)	ATE104985T1 (de)
CA (1)	CA2009095A1 (de)
DE (1)	DE69008396D1 (de)
NL (1)	NL8900328A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL9001834A (nl) *	1990-08-16	1992-03-16	Pharmachemie Bv	Nieuwe antracyclineverbindingen met anti-tumorwerkzaamheid, nieuwe tussenverbindingen voor de bereiding van deze antracyclineverbindingen, alsmede preparaten die de aktieve antracyclineverbindingen bevatten.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4415498A (en) *	1979-11-07	1983-11-15	Research Corporation	Synthesis of daunomycinone and the derivatives thereof

1989
- 1989-02-10 NL NL8900328A patent/NL8900328A/nl not_active Application Discontinuation
1990
- 1990-01-29 DE DE69008396T patent/DE69008396D1/de not_active Expired - Lifetime
- 1990-01-29 AT AT9090200210T patent/ATE104985T1/de not_active IP Right Cessation
- 1990-01-29 EP EP90200210A patent/EP0387929B1/de not_active Expired - Lifetime
- 1990-02-01 US US07/473,537 patent/US5079349A/en not_active Expired - Fee Related
- 1990-02-01 CA CA002009095A patent/CA2009095A1/en not_active Abandoned
- 1990-02-03 JP JP2024986A patent/JPH02235889A/ja active Pending

Also Published As

Publication number	Publication date
JPH02235889A (ja)	1990-09-18
DE69008396D1 (de)	1994-06-01
EP0387929A1 (de)	1990-09-19
EP0387929B1 (de)	1994-04-27
CA2009095A1 (en)	1990-08-10
US5079349A (en)	1992-01-07
ATE104985T1 (de)	1994-05-15

Legal Events

Date	Code	Title	Description
1990-09-03	A1B	A search report has been drawn up
1991-10-01	BV	The patent application has lapsed

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