NL8900329A - Cyclische triketonverbindingen en trimethylsilyloxybutadieenverbindingen en hun toepassing bij het bereiden van daunomycinonderivaten. - Google Patents

Cyclische triketonverbindingen en trimethylsilyloxybutadieenverbindingen en hun toepassing bij het bereiden van daunomycinonderivaten. Download PDF

Info

Publication number: NL8900329A
Authority: NL; Netherlands
Prior art keywords: group; compounds; compound; formula; alkyl
Prior art date: 1989-02-10

Application number

NL8900329A

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 NL8900329A priority Critical patent/NL8900329A/nl

1990-01-29 Priority to DK90200212.0T priority patent/DK0383372T3/da

1990-01-29 Priority to ES90200212T priority patent/ES2055296T3/es

1990-01-29 Priority to AT90200212T priority patent/ATE87901T1/de

1990-01-29 Priority to DE9090200212T priority patent/DE69001266T2/de

1990-01-29 Priority to EP90200212A priority patent/EP0383372B1/de

1990-02-01 Priority to CA002009096A priority patent/CA2009096A1/en

1990-02-01 Priority to US07/473,538 priority patent/US5097051A/en

1990-02-03 Priority to JP2024987A priority patent/JPH02235836A/ja

1990-09-03 Publication of NL8900329A publication Critical patent/NL8900329A/nl

1991-12-20 Priority to US07/812,902 priority patent/US5183913A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 25
238000002360 preparation method Methods 0.000 title claims abstract description 6
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 3
UQGOYQLRRBTVFM-UHFFFAOYSA-N buta-1,3-dienoxy(trimethyl)silane Chemical class C[Si](C)(C)OC=CC=C UQGOYQLRRBTVFM-UHFFFAOYSA-N 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
125000004122 cyclic group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 3
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000000034 method Methods 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
238000006257 total synthesis reaction Methods 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 14
150000001993 dienes Chemical class 0.000 abstract description 7
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 6
238000003786 synthesis reaction Methods 0.000 abstract description 5
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 4
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 4
238000005698 Diels-Alder reaction Methods 0.000 abstract description 3
230000015572 biosynthetic process Effects 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 2
229940009456 adriamycin Drugs 0.000 abstract 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 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
RQNVIKXOOKXAJQ-UHFFFAOYSA-N naphthazarin Chemical compound O=C1C=CC(=O)C2=C1C(O)=CC=C2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
-1 1-substituted-1,3-butadiene Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
0 CC(C(C(C1)N)O)OC1OC(CC(C1)(C(C*)=O)O)c(c(O)c2C(c3c4cccc3OC)=O)c1c(O)c2C4=O Chemical compound CC(C(C(C1)N)O)OC1OC(CC(C1)(C(C*)=O)O)c(c(O)c2C(c3c4cccc3OC)=O)c1c(O)c2C4=O 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
WIQMWNKYSYJIQG-UHFFFAOYSA-N Juglon Natural products C1=CC(O)=C2C(=O)C(OC)=C(C)C(=O)C2=C1 WIQMWNKYSYJIQG-UHFFFAOYSA-N 0.000 description 2
230000000118 anti-neoplastic effect Effects 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
230000006698 induction Effects 0.000 description 2
KQPYUDDGWXQXHS-UHFFFAOYSA-N juglone Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2O KQPYUDDGWXQXHS-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
KFCUVLQKCWWEDC-UBKPWBPPSA-N CC(CCC1/C=N/S)c2c1c(O)c(C(C=CC1=O)=O)c1c2O Chemical compound CC(CCC1/C=N/S)c2c1c(O)c(C(C=CC1=O)=O)c1c2O KFCUVLQKCWWEDC-UBKPWBPPSA-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
RQNVIKXOOKXAJQ-UHFFFAOYSA-M [O-]c(cc1)c(C(C=CC2=O)=O)c2c1O Chemical compound [O-]c(cc1)c(C(C=CC2=O)=O)c2c1O RQNVIKXOOKXAJQ-UHFFFAOYSA-M 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 1
238000010586 diagram Methods 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

Landscapes

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

NL8900329A 1989-02-10 1989-02-10 Cyclische triketonverbindingen en trimethylsilyloxybutadieenverbindingen en hun toepassing bij het bereiden van daunomycinonderivaten. NL8900329A (nl)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
NL8900329A NL8900329A (nl)	1989-02-10	1989-02-10	Cyclische triketonverbindingen en trimethylsilyloxybutadieenverbindingen en hun toepassing bij het bereiden van daunomycinonderivaten.
DK90200212.0T DK0383372T3 (da)	1989-02-10	1990-01-29	Cykliske triketonforbindelser og trimethylsilyloxybutadienforbindelser samt deres anvendelse til fremstilling af daunomycinonafledede
ES90200212T ES2055296T3 (es)	1989-02-10	1990-01-29	Compuestos ciclicos de tricetona y compuestos de trimetilsililoxi butadieno y su uso en la preparacion de derivados de la daunomicinona.
AT90200212T ATE87901T1 (de)	1989-02-10	1990-01-29	Cyclische triketonverbindungen und trimethylsilylbutadienverbindungen und ihre verwendung zur herstellung von daunomycinonderivaten.
DE9090200212T DE69001266T2 (de)	1989-02-10	1990-01-29	Cyclische triketonverbindungen und trimethylsilylbutadienverbindungen und ihre verwendung zur herstellung von daunomycinon-derivaten.
EP90200212A EP0383372B1 (de)	1989-02-10	1990-01-29	Cyclische Triketonverbindungen und Trimethylsilylbutadienverbindungen und ihre Verwendung zur Herstellung von Daunomycinon-Derivaten
CA002009096A CA2009096A1 (en)	1989-02-10	1990-02-01	Cyclic triketone compounds and trimethylsilyloxy butadiene ckompounds and their use in the preparation of daunomycinone derivatives
US07/473,538 US5097051A (en)	1989-02-10	1990-02-01	Cyclic triketone compounds and trimethylsilyloxy butadiene compounds and their use in the preparation of daunomycinone derivatives
JP2024987A JPH02235836A (ja)	1989-02-10	1990-02-03	サイクリックトリケトン化合物、トリメチルシリルオキシブタジエン化合物及びそれらのダウノマイシノン誘導体製造への用途
US07/812,902 US5183913A (en)	1989-02-10	1991-12-20	Cyclic triketone compounds and trimethylsilyoxy butadiene compounds and their use in the preparation of daunomycinone derivatives

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8900329		1989-02-10
NL8900329A NL8900329A (nl)	1989-02-10	1989-02-10	Cyclische triketonverbindingen en trimethylsilyloxybutadieenverbindingen en hun toepassing bij het bereiden van daunomycinonderivaten.

Publications (1)

Publication Number	Publication Date
NL8900329A true NL8900329A (nl)	1990-09-03

Family

ID=19854110

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8900329A NL8900329A (nl)	1989-02-10	1989-02-10	Cyclische triketonverbindingen en trimethylsilyloxybutadieenverbindingen en hun toepassing bij het bereiden van daunomycinonderivaten.

Country Status (9)

Country	Link
US (1)	US5097051A (de)
EP (1)	EP0383372B1 (de)
JP (1)	JPH02235836A (de)
AT (1)	ATE87901T1 (de)
CA (1)	CA2009096A1 (de)
DE (1)	DE69001266T2 (de)
DK (1)	DK0383372T3 (de)
ES (1)	ES2055296T3 (de)
NL (1)	NL8900329A (de)

Families Citing this family (4)

* 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.
US5416403A (en) *	1993-02-11	1995-05-16	Hewlett-Packard Corporation	Current stabilizing circuit
FR2740772B1 (fr) *	1995-11-02	1998-01-16	Girex	Procede de preparation d'anthraquinones substituees et application a la preparation de rheines
DE102007031461A1 (de)	2007-07-05	2009-01-08	Sappok, Manfred, Dipl.-Phys. Dr.	Verfahren zum Stabilisieren von Heizöl oder Dieselöl, insbesondere aus der Depolimerisation von kohlenwasserstoffhaltigen Rückständen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4405522A (en) *	1982-01-18	1983-09-20	Adria Laboratories Inc.	Anthracycline synthesis

1989
- 1989-02-10 NL NL8900329A patent/NL8900329A/nl not_active Application Discontinuation
1990
- 1990-01-29 EP EP90200212A patent/EP0383372B1/de not_active Expired - Lifetime
- 1990-01-29 AT AT90200212T patent/ATE87901T1/de not_active IP Right Cessation
- 1990-01-29 ES ES90200212T patent/ES2055296T3/es not_active Expired - Lifetime
- 1990-01-29 DE DE9090200212T patent/DE69001266T2/de not_active Expired - Fee Related
- 1990-01-29 DK DK90200212.0T patent/DK0383372T3/da active
- 1990-02-01 US US07/473,538 patent/US5097051A/en not_active Expired - Fee Related
- 1990-02-01 CA CA002009096A patent/CA2009096A1/en not_active Abandoned
- 1990-02-03 JP JP2024987A patent/JPH02235836A/ja active Pending

Also Published As

Publication number	Publication date
EP0383372B1 (de)	1993-04-07
DE69001266D1 (de)	1993-05-13
EP0383372A1 (de)	1990-08-22
DK0383372T3 (da)	1993-08-02
ATE87901T1 (de)	1993-04-15
JPH02235836A (ja)	1990-09-18
CA2009096A1 (en)	1990-08-10
US5097051A (en)	1992-03-17
DE69001266T2 (de)	1993-09-16
ES2055296T3 (es)	1994-08-16

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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