CZ249997A3 - Novel inhibitors of farnesyl transferase, process of their preparation and pharmaceutical compositions containing such inhibitors - Google Patents

Novel inhibitors of farnesyl transferase, process of their preparation and pharmaceutical compositions containing such inhibitors Download PDF

Info

Publication number: CZ249997A3
Authority: CZ; Czechia
Prior art keywords: group; hydrogen atom; alkyl; optionally substituted; carbon atoms
Prior art date: 1995-02-09

Application number

CZ972499A

Other languages

Czech (cs)

English (en)

Inventor

Francois-Frederic Clerc

Original Assignee

Rhone Poulenc Rorer Sa

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.)

1995-02-09

Filing date

1996-02-07

Publication date

1997-11-12

1996-02-07 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1997-11-12 Publication of CZ249997A3 publication Critical patent/CZ249997A3/cs

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title abstract description 6
102000007317 Farnesyltranstransferase Human genes 0.000 title description 6
108010007508 Farnesyltranstransferase Proteins 0.000 title description 6
239000003112 inhibitor Substances 0.000 title description 4
238000000034 method Methods 0.000 title description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 48
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
-1 alkoxycarbonyl radical Chemical class 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
229910052799 carbon Inorganic materials 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 11
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
150000002596 lactones Chemical class 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
125000003282 alkyl amino group Chemical group 0.000 claims abstract 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
125000005236 alkanoylamino group Chemical group 0.000 claims abstract 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
108090000765 processed proteins & peptides Proteins 0.000 claims description 14
102000004196 processed proteins & peptides Human genes 0.000 claims description 10
150000001413 amino acids Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
239000005977 Ethylene Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
150000004665 fatty acids Chemical group 0.000 claims description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
239000011593 sulfur Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
239000003528 protein farnesyltransferase inhibitor Substances 0.000 abstract description 3
125000000539 amino acid group Chemical group 0.000 abstract description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
150000003254 radicals Chemical class 0.000 abstract 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 abstract 1
125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
230000001093 anti-cancer Effects 0.000 abstract 1
125000005313 fatty acid group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
239000000203 mixture Substances 0.000 description 12
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
150000001721 carbon Chemical group 0.000 description 7
239000000047 product Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 5
102000016914 ras Proteins Human genes 0.000 description 5
108010014186 ras Proteins Proteins 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VWFJDQUYCIWHTN-UHFFFAOYSA-N Farnesyl pyrophosphate Natural products CC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)OP(O)(O)=O VWFJDQUYCIWHTN-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000006126 farnesylation Effects 0.000 description 3
239000000945 filler Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
101100312806 Homo sapiens TMEM106C gene Proteins 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
ZJPGOXWRFNKIQL-JYJNAYRXSA-N Phe-Pro-Pro Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CC=CC=C1 ZJPGOXWRFNKIQL-JYJNAYRXSA-N 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
102100034851 Transmembrane protein 106C Human genes 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229920001903 high density polyethylene Polymers 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000004700 high-density polyethylene Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000012528 membrane Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
239000008223 sterile water Substances 0.000 description 2
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239000000725 suspension Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
238000009736 wetting Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
RMTDKXQYAKLQKF-INIZCTEOSA-N (2r)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-sulfanylpropanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CS)C(=O)O)C3=CC=CC=C3C2=C1 RMTDKXQYAKLQKF-INIZCTEOSA-N 0.000 description 1
OXFGRWIKQDSSLY-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-2-ium-1-carboxylate Chemical compound C1=CC=C2C(C(=O)O)NCCC2=C1 OXFGRWIKQDSSLY-UHFFFAOYSA-N 0.000 description 1
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
VHJLVAABSRFDPM-UHFFFAOYSA-N 1,4-dithiothreitol Chemical compound SCC(O)C(O)CS VHJLVAABSRFDPM-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
VWFJDQUYCIWHTN-YFVJMOTDSA-N 2-trans,6-trans-farnesyl diphosphate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CO[P@](O)(=O)OP(O)(O)=O VWFJDQUYCIWHTN-YFVJMOTDSA-N 0.000 description 1
AXOUQPYEFRIVBI-UHFFFAOYSA-N 4-benzyl-1-hydroxytriazole Chemical compound N1=NN(O)C=C1CC1=CC=CC=C1 AXOUQPYEFRIVBI-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
206010018910 Haemolysis Diseases 0.000 description 1
101001074035 Homo sapiens Zinc finger protein GLI2 Proteins 0.000 description 1
TUYOFUHICRWDGA-CIUDSAMLSA-N Ile-Met Chemical compound CC[C@H](C)[C@H](N)C(=O)N[C@H](C(O)=O)CCSC TUYOFUHICRWDGA-CIUDSAMLSA-N 0.000 description 1
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101150040459 RAS gene Proteins 0.000 description 1
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229930006000 Sucrose Natural products 0.000 description 1
ODUHAIXFXFACDY-SRVKXCTJSA-N Val-Val-Met Chemical compound CSCC[C@@H](C(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](N)C(C)C ODUHAIXFXFACDY-SRVKXCTJSA-N 0.000 description 1
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102100035558 Zinc finger protein GLI2 Human genes 0.000 description 1
NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000004899 c-terminal region Anatomy 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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229940093471 ethyl oleate Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
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239000011152 fibreglass Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
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125000000623 heterocyclic group Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
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XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1013—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/07—Tetrapeptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Gastroenterology & Hepatology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Epidemiology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CZ972499A 1995-02-09 1996-02-07 Novel inhibitors of farnesyl transferase, process of their preparation and pharmaceutical compositions containing such inhibitors CZ249997A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9501490A FR2730492B1 (fr)	1995-02-09	1995-02-09	Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent
PCT/FR1996/000199 WO1996024612A1 (fr)	1995-02-09	1996-02-07	Inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent

Publications (1)

Publication Number	Publication Date
CZ249997A3 true CZ249997A3 (en)	1997-11-12

Family

ID=9475981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ972499A CZ249997A3 (en)	1995-02-09	1996-02-07	Novel inhibitors of farnesyl transferase, process of their preparation and pharmaceutical compositions containing such inhibitors

Country Status (16)

Country	Link
EP (1)	EP0808329A1 (de)
JP (1)	JPH10513468A (de)
KR (1)	KR19980702049A (de)
CN (1)	CN1173873A (de)
AU (1)	AU4722896A (de)
BR (1)	BR9607318A (de)
CA (1)	CA2210953A1 (de)
CZ (1)	CZ249997A3 (de)
FI (1)	FI973279A0 (de)
FR (1)	FR2730492B1 (de)
NO (1)	NO973607D0 (de)
PL (1)	PL321710A1 (de)
SK (1)	SK108897A3 (de)
TR (1)	TR199700726T1 (de)
WO (1)	WO1996024612A1 (de)
ZA (1)	ZA961073B (de)

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US5141851A (en) *	1990-04-18	1992-08-25	Board Of Regents, The University Of Texas System	Isolated farnesyl protein transferase enzyme
CA2072033A1 (en) *	1991-06-28	1992-12-29	Jackson B. Gibbs	Non-substrate inhibitors of farnesyl protein transferase
CA2118985A1 (en) *	1993-04-02	1994-10-03	Dinesh V. Patel	Heterocyclic inhibitors of farnesyl protein transferase
AU6909194A (en) *	1993-05-14	1994-12-12	Board Of Regents, The University Of Texas System	Preparation of n-cyanodithioimino-carbonates and 3-mercapto-5-amino-1h-1,2,4-triazole
US5439918A (en) *	1994-03-14	1995-08-08	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase

1995
- 1995-02-09 FR FR9501490A patent/FR2730492B1/fr not_active Expired - Fee Related
1996
- 1996-02-07 EP EP96903062A patent/EP0808329A1/de not_active Withdrawn
- 1996-02-07 CZ CZ972499A patent/CZ249997A3/cs unknown
- 1996-02-07 CN CN96191866A patent/CN1173873A/zh active Pending
- 1996-02-07 JP JP8524038A patent/JPH10513468A/ja active Pending
- 1996-02-07 PL PL96321710A patent/PL321710A1/xx unknown
- 1996-02-07 KR KR1019970705444A patent/KR19980702049A/ko not_active Withdrawn
- 1996-02-07 TR TR97/00726T patent/TR199700726T1/xx unknown
- 1996-02-07 WO PCT/FR1996/000199 patent/WO1996024612A1/fr not_active Ceased
- 1996-02-07 CA CA002210953A patent/CA2210953A1/fr not_active Abandoned
- 1996-02-07 SK SK1088-97A patent/SK108897A3/sk unknown
- 1996-02-07 BR BR9607318A patent/BR9607318A/pt not_active Application Discontinuation
- 1996-02-07 AU AU47228/96A patent/AU4722896A/en not_active Abandoned
- 1996-02-09 ZA ZA961073A patent/ZA961073B/xx unknown
1997
- 1997-08-05 NO NO973607A patent/NO973607D0/no unknown
- 1997-08-08 FI FI973279A patent/FI973279A0/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
ZA961073B (en)	1996-08-20
FI973279A7 (fi)	1997-08-08
JPH10513468A (ja)	1998-12-22
CN1173873A (zh)	1998-02-18
EP0808329A1 (de)	1997-11-26
WO1996024612A1 (fr)	1996-08-15
AU4722896A (en)	1996-08-27
NO973607L (no)	1997-08-05
BR9607318A (pt)	1997-12-30
FI973279A0 (fi)	1997-08-08
TR199700726T1 (xx)	1998-01-21
MX9705969A (es)	1997-11-29
FR2730492A1 (fr)	1996-08-14
PL321710A1 (en)	1997-12-22
SK108897A3 (en)	1997-12-10
KR19980702049A (ko)	1998-07-15
NO973607D0 (no)	1997-08-05
FR2730492B1 (fr)	1997-03-14
CA2210953A1 (fr)	1996-08-15

Publication	Publication Date	Title
CZ249997A3 (en)	1997-11-12	Novel inhibitors of farnesyl transferase, process of their preparation and pharmaceutical compositions containing such inhibitors
CZ249897A3 (en)	1997-11-12	Novel inhibitors of farnesyl transferase, process of their preparation and pharmaceutical compositions containing such inhibitors
EP0578083B1 (de)	1999-04-07	Zyklische Adhäsionsinhibitoren
IL84766A (en)	1994-02-27	Phosphinic acid derivatives, their manufacture and pharmaceutical compositions containing them
KR19980701469A (ko)	1998-05-15	신규한 파르네실 전이 효소 억제제, 이의 제조방법 및 이를 함유하는 약학 조성물(novel farnesyl transferase inhibitors, preparation thereof and pharmaceutical compositions containing same)
CZ82195A3 (en)	1996-09-11	Inhibitors of farnesyl-protein transferase containing imidazole nucleus
WO1996040752A1 (en)	1996-12-19	Novel dolastatin derivatives, their preparation and use
GB2045771A (en)	1980-11-05	Mercaptoacyldipeptides
DK173511B1 (da)	2001-01-15	Dipeptidylnaphthyridinderivater samt antibakterielle midler, som omfatter disse
CZ20002681A3 (cs)	2002-03-13	Cyklické tyrosinové dipeptidy
RU2259997C2 (ru)	2005-09-10	Ингибиторы фарнезилтрансферазы
IE42249B1 (en)	1980-07-02	Octapeptide derivatives having an oxygen or sulfur containing moiety in the c-terminal position
HUT66469A (en)	1994-11-28	Linear peptides
EP0850950A1 (de)	1998-07-01	Peptidderivate
MXPA97006015A (en)	1998-07-03	Novedous inhibitors of farnesil transferase, supreparation and pharmaceutical compositions chelos contie
MXPA97005969A (en)	1998-07-03	New farnesil inhibitors transfer your preparation and the pharmaceutical compositions that contain them
EP3946607A1 (de)	2022-02-09	Bivalente antagonisten von inhibitoren von apoptoseproteinen
EP4347618B1 (de)	2025-01-29	Zyklische peptidantibiotika
CA3070992A1 (en)	2019-01-31	Dimeric peptide inhibitors of apoptosis proteins
CA2201348A1 (en)	1996-04-04	Thiol-free inhibitors of farnesyl-protein transferase
HUP9903611A2 (hu)	2000-02-28	Prenil-transzferáz-inhibitorok
HK1112899A (en)	2008-09-19	Tetrapeptide analogs