3932-97-6

Basic information

• Product Name: 2,4-Dichloro-5-trifluoromethylpyrimidine
• Synonyms: 2,4-DICHLORO-5-(TRIFLUOROMETHYL)PYRIMIDINE;5-TRIFLUOROMETHYL-2,4-DICHLOROPYRIMIDINE;PyriMidine, 2,4-dichloro-5-(trifluoroMethyl)-;4-(broMoMethyl)-3-chlorobenzaMide;2,4-Dichloro-5-(trifluoromethyl)-1,3-diazine;2,4-Dichloro-5-(trifluoroMethyl)pyriMidine 97%;2,4-Dichloro-5-(trifluoroMethyl);2,4-Dichloro-5-trifluoromethylpyrimidine 5-Trifluoromethyl-2,4-dichloropyrimidine
• CAS NO: 3932-97-6
• Molecular Formula: C₅HCl₂F₃N₂
• Molecular Weight: 216.98
• EINECS: 1592732-453-0
• Product Categories: pharmacetical;Pyrimidine;Building Blocks;Halogenated;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;Fluorine series;Pyrazoles
• Mol File: 3932-97-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 49℃/32mm
• Flash Point: 200 ºF
• Appearance: /
• Density: 1.6087
• Vapor Pressure: 0.101mmHg at 25°C
• Refractive Index: 1.4749
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• PKA: -4.89±0.29(Predicted)
• CAS DataBase Reference: 2,4-Dichloro-5-trifluoromethylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-5-trifluoromethylpyrimidine(3932-97-6)
• EPA Substance Registry System: 2,4-Dichloro-5-trifluoromethylpyrimidine(3932-97-6)

Safety Data

• Hazard Codes: Xi,C,T
• Statements: 36/37/38-36-25
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2810
• WGK Germany: 3
• HazardClass: CORROSIVE
• PackingGroup: Ⅲ
• Hazardous Substances Data: 3932-97-6(Hazardous Substances Data)

Usage

Chemical Properties

White liquid or solid

Uses

2,4-Dichloro-5-trifluoromethylpyrimidine is a reactant in the preparation of pyrimidine derivatives as inhibitors of gene ALK protein Kinase phosphorylating kinase and as cell proliferation inhibitors.

InChI:InChI=1/C5HCl2F3N2/c6-3-2(5(8,9)10)1-11-4(7)12-3/h1H

Synthetic route

5-trifluoromethyluracil (54-20-6) → 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6)

Conditions	Yield
With phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate at 85 - 100℃; for 20h;	95%
With phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate In water at 85 - 100℃; for 20.25h;	95%
With N-ethyl-N,N-diisopropylamine; trichlorophosphate; phosphoric acid at 85 - 100℃; for 20.25h;	95%

trifluoromethyluracil → 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6)

Conditions	Yield
With phosphoric acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate at 85 - 100℃; for 20h;	95%

(trifluoromethyl)trimethylsilane (81290-20-2) + 2,4-dichloro-5-iodopyrimidine (13544-44-0) → 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6)

Conditions	Yield
With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline; Trimethyl borate In dimethyl sulfoxide at 60℃; for 2h; Inert atmosphere;	81%

2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) + 4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine (170911-92-9) → tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate (1393900-79-2)

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.833333h; Stage #2: 4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 18h;	98%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h; Stage #2: 4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 18h;	98%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc dibromide In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h; Stage #2: 4-(4-aminophenyl)-1-t-butyloxycarbonylpiperazine With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 3h;	72.3%

tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate (170011-57-1) + 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (1383682-52-7)

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In cis-1,2-Dichloroethylene; diethyl ether; butan-1-ol at 20℃; for 0.166667h; Stage #2: tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate With triethylamine In cis-1,2-Dichloroethylene; diethyl ether; butan-1-ol at 20℃;	98%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃; for 0.166667h; Stage #2: tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃;	98%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Inert atmosphere; Stage #2: tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 24.5h;	88%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Inert atmosphere; Stage #2: tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 24.5h;	88%

2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) + tert-butyl (4-aminobenzyl)carbamate (94838-55-8) → tert-butyl 4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzylcarbamate (1073160-22-1)

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃; for 0.333333h; Stage #2: tert-butyl (4-aminobenzyl)carbamate With triethylamine at 20℃;	97%

4-[(tert-butyldimethylsilyl)oxy]aniline (111359-74-1) + 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-4-chloro-5-(trifluoromethyl)pyrimidin-2-amine

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc dibromide In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h; Stage #2: 4-[(tert-butyldimethylsilyl)oxy]aniline With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 20h;	97%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc dibromide In 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h; Stage #2: 4-[(tert-butyldimethylsilyl)oxy]aniline With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 20h;	97%

4-nitro-phenol (100-02-7) + 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → 4-chloro-2-(4-nitrophenoxyl)-5-trifluoromethyl pyrimidine (1265228-21-4)

Conditions	Yield
With 4-methyl-morpholine In isopropyl alcohol at -5 - 20℃; for 4h;	96%
With 4-methyl-morpholine In isopropyl alcohol at -5 - 20℃;	90%
In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at -5 - 20℃; for 4h; Product distribution / selectivity;	90%
With N-(2-(4-tert-butyl-piperazin-1-yl)-4-methoxyl-5-(6-(1-methyl-1H-indol-3-yl)-pyrimidin-4-ylamino)-phenyl)-acrylamide In isopropyl alcohol for 1h; Cooling with ice;

2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) + phenol (108-95-2) → 2-chloro-4-phenoxy-5-(trifluoromethyl)pyrimidine

Conditions	Yield
With potassium carbonate In acetone at 0℃; for 1h;	96%

2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) + sodium thiomethoxide (5188-07-8) → 4-chloro-2-methylsulfany l-5-(trifluoromethyl)pyrimidine (919116-36-2)

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether at 0℃; for 2h; Stage #2: sodium thiomethoxide In diethyl ether at 0 - 20℃; for 48h;	95%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether at 0℃; for 2h; Stage #2: sodium thiomethoxide In diethyl ether at 0 - 20℃; for 48h;	95%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether at 0℃; for 2h; Stage #2: sodium thiomethoxide In diethyl ether at 0 - 25℃; for 48h;	95%

4-chloro-aniline (106-47-8) + 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → (4-chlorophenyl)-(4-chloro-5-trifluoromethyl-pyrimidin-2-yl)-amine (514842-83-2) + C11H6Cl2F3N3 (1448795-01-4)

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; Stage #2: 4-chloro-aniline With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃;	A 95% B n/a

2,2,2-trifluoroethanol (75-89-8) + 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → 2,4-bis(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)pyrimidine

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere; Stage #2: 2,4-dichloro-5-trifluoromethylpyrimidine In tetrahydrofuran; hexane at -20 - 40℃; for 24.5h; Inert atmosphere;	91%
Stage #1: 2,2,2-trifluoroethanol With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere; Stage #2: 2,4-dichloro-5-trifluoromethylpyrimidine In tetrahydrofuran; hexane at -20 - 40℃; for 24.5h; Inert atmosphere;	91%
Stage #1: 2,2,2-trifluoroethanol With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere; Stage #2: 2,4-dichloro-5-trifluoromethylpyrimidine In tetrahydrofuran; hexane at 40℃; for 24h;	91%

2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → 5-trifluoromethyluracil (54-20-6)

Conditions	Yield
With acetic acid In water at 110℃; for 5h;	90.6%

2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) + 4-(4-tert-butoxycarbonyl-piperazino-methyl)-aniline (304897-49-2) → tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzyl)piperazine-1-carboxylate (1393901-46-6)

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Stage #2: 4-(4-tert-butoxycarbonyl-piperazino-methyl)-aniline With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 20℃; Cooling with ice;	90%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Inert atmosphere; Stage #2: 4-(4-tert-butoxycarbonyl-piperazino-methyl)-aniline With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃;	90%

3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester (875798-79-1) + 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → tert-butyl 3-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (1393900-90-7)

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h; Stage #2: 3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 60h;	90%
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 0.5h; Stage #2: 3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester With triethylamine In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 60h;	90%

tert-butyl 4-(4-amino-2-methylphenyl)-piperidine-1-carboxylate (955369-50-3) + 2,4-dichloro-5-trifluoromethylpyrimidine (3932-97-6) → tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidine-2-yl)amino)-2-methylphenyl)piperidine-1-carboxylate (1383682-55-0)

Conditions	Yield
Stage #1: 2,4-dichloro-5-trifluoromethylpyrimidine With zinc(II) chloride In diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol at 0℃; for 1h; Inert atmosphere; Stage #2: tert-butyl 4-(4-amino-2-methylphenyl)-piperidine-1-carboxylate With triethylamine In 1,2-dichloro-ethane; tert-butyl alcohol at 0 - 20℃; for 16.5h;	89%

Upstream product

• 24377-95-5 3-chloro-4-methylbenzamide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 13544-44-0 2,4-dichloro-5-iodopyrimidine 
• 54-20-6 5-trifluoromethyluracil 

Downstream Products

• 1030377-63-9 (5R)-1-[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]-5-methyl-4-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]-1,4-diazepane 
• 1393900-79-2 tert-butyl 4-(4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate 
• 919116-36-2 4-chloro-2-methylsulfany l-5-(trifluoromethyl)pyrimidine 
• 1380308-17-7 2-chloro-[4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-5-methoxy-benzyl]-phosphonic acid diethyl ester 
• 1380308-02-0 diethyl 2-chloro-4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)-3-methoxybenzylphosphonate 
• 1380304-69-7 diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-fluorobenzyl)phosphonate 
• 1257996-58-9 diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate 
• 1380305-76-9 diethyl (3-bromo-4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}benzyl)phosphonate 
• 1380305-87-2 diethyl (4-{[4-chloro-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methylbenzyl)phosphonate 
• 1380302-86-2 sodium ethyl (4-{[4-({7-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate 
• 1257996-05-6 diethyl (4-{[4-({7-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl}amino)-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)phosphonate 
• 515824-43-8 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidine-4-amine 
• 1374507-25-1 N-[3-[[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]prop-2-enamide 
• 1374507-23-9 tert-butyl (3-((2-chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)phenyl)aminocarboxylate 

Relevant articles and documents

Method for preparing 5-trifluoromethyl uracil

The invention belongs to the field of organic synthesis, and specifically relates to a method for preparing 5-trifluoromethyl uracil. The method comprises the following steps: firstly, carrying out chlorination reaction on 5-iodouracil and phosphorus oxychloride, thus obtaining 2,4-dichloro-5-iodopyrimidine; secondly, carrying out trifluoromethylation reaction on the 2,4-dichloro-5-iodopyrimidineand a trifluoromethylating reagent, thus obtaining 2,4-dichloro-5-trifluoromethylpyrimidine; finally, enabling the 2,4-dichloro-5-trifluoromethylpyrimidine to react with acetic acid, thus obtaining aproduct. According to the method disclosed by the invention, since chlorination reaction, trifluoromethylation reaction and hydrolysis reaction are adopted, a key intermediate-trifluoromethyl uracil of trifluorothymidine is synthesized in high yield, low cost and low pollution.

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SYNTHESIS OF 2,4-DICHLORO-5-TRIFLUOROMETHYL-PYRIMIDINE

This invention relates to a novel method for the synthesis of 2,4-dichloro-5-trifluoromethyl-pyrimidine useful as intermediate in the manufacture of pharmaceutically active ingredients.

NOVEL PROCESS FOR THE MANUFACTURE OF 2,4-DICHLORO-5-TRIFLUOROMETHYL-PYRIMIDINE

This invention relates to a novel method for the synthesis of 2,4-dichloro-5-trifluoromethyl- pyrimidine useful as intermediate in the manufacture of pharmaceutically active ingredients.

PYRIMIDINE DERIVATIVES FOR THE TREATMENT OF ABNORMAL CELL GROWTH

The present invention relates to salts, solvates and substoichiometric solvates of N-[3-[[[2-[(2,3-dihydro-2-oxo-1H-indo1-5-yl)amino]-5-(trifluoromethyl)-4-pyrimidinyl]amino]methyl]-2-pyridinyl]-N-methylmethanesulfonamide. The invention also provides pharmaceutical compositions comprising such complexes, as well as methods of treating abnormal cell growth by administering the complexes of the invention.

2,4-DIAMINOPYRIMIDINE DERIVATES AS PTK2- INHIBITORS FOR THE TREATMENT OF ABNORMAL CELL GROWTH

The present invention encompasses compounds of general formula (1) wherein R1-R3 and n are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use for preparing a medicament having the above-mentioned properties.

SUBSTITUTED PYRIMIDINES FOR THE TREATMENT OF CANCER

The present invention encompasses compounds of general formula (1) wherein B, R1 to R5, Rx, m and n are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and their use in such treatment.

2, 4 -DIAMINOPYRIMIDINES FOR THE TREATMENT OF DISEASES CHARACTERISED BY EXCESSIVE OR ABNORMAL CELL PROLIFERATION

The present invention encompasses compounds of general formula (1), wherein A, B, R1 to R5, Rx m, n and p are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, pharmaceutical preparations which contain such compounds and the use thereof [as] medicaments.