JPH10513468A - ファルネシル転移酵素阻害剤、これらの調製、及びこれらを含む製薬学的組成 - Google Patents

ファルネシル転移酵素阻害剤、これらの調製、及びこれらを含む製薬学的組成

Info

Publication number: JPH10513468A
Authority: JP; Japan
Prior art keywords: group; hydrogen atom; carbon atoms; substituted; atom
Prior art date: 1995-02-09
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.): Pending

Application number

JP8524038A

Other languages

English (en)

Japanese (ja)

Inventor

クレルク，フランソワ

Original Assignee

ローン−プーラン・ロレ・ソシエテ・アノニム

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

1998-12-22

1996-02-07 Application filed by ローン−プーラン・ロレ・ソシエテ・アノニム filed Critical ローン−プーラン・ロレ・ソシエテ・アノニム

1998-12-22 Publication of JPH10513468A publication Critical patent/JPH10513468A/ja

Status Pending legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
-1 their preparation Substances 0.000 title claims description 25
238000002360 preparation method Methods 0.000 title abstract description 6
239000003528 protein farnesyltransferase inhibitor Substances 0.000 title abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 64
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 50
125000000217 alkyl group Chemical group 0.000 claims abstract description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 5
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
125000000539 amino acid group Chemical group 0.000 claims abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 4
125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 3
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 3
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
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 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
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
229910052717 sulfur Chemical group 0.000 claims abstract description 3
125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
125000005313 fatty acid group Chemical group 0.000 claims abstract 3
229910052799 carbon Inorganic materials 0.000 claims description 17
108090000765 processed proteins & peptides Proteins 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 5
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
238000000034 method Methods 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
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 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
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000004149 thio group Chemical group *S* 0.000 claims description 2
239000012752 auxiliary agent Substances 0.000 claims 2
125000004663 dialkyl amino 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
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract description 3
239000001257 hydrogen Substances 0.000 abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
230000001093 anti-cancer Effects 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 17
239000000203 mixture Substances 0.000 description 16
239000000047 product Substances 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
150000001413 amino acids Chemical class 0.000 description 8
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 7
102000007317 Farnesyltranstransferase Human genes 0.000 description 7
108010007508 Farnesyltranstransferase Proteins 0.000 description 7
239000011347 resin Substances 0.000 description 7
238000005406 washing Methods 0.000 description 7
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
102000016914 ras Proteins Human genes 0.000 description 6
108010014186 ras Proteins Proteins 0.000 description 6
229920005989 resin Polymers 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
210000004027 cell Anatomy 0.000 description 5
238000010511 deprotection reaction Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000004665 fatty acids Chemical group 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
101150040459 RAS gene Proteins 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
PYPZMFDMCCWNST-NAKRPEOUSA-N Val-Ile-Cys Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CS)C(=O)O)NC(=O)[C@H](C(C)C)N PYPZMFDMCCWNST-NAKRPEOUSA-N 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
210000004899 c-terminal region Anatomy 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000006126 farnesylation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000004700 high-density polyethylene Substances 0.000 description 2
239000003701 inert diluent 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
238000002414 normal-phase solid-phase extraction Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
108700042226 ras Genes Proteins 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-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
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
239000005711 Benzoic acid Substances 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
101001074035 Homo sapiens Zinc finger protein GLI2 Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
239000003875 Wang resin Substances 0.000 description 1
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
125000003158 alcohol group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000000721 bacterilogical effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
150000004662 dithiols Chemical class 0.000 description 1
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 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
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
235000003599 food sweetener Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229920001903 high density polyethylene Polymers 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000003906 humectant Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000011534 incubation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
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
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000002934 lysing effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000008505 β-D-glucopyranosides Chemical class 0.000 description 1

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)

JP8524038A 1995-02-09 1996-02-07 ファルネシル転移酵素阻害剤、これらの調製、及びこれらを含む製薬学的組成 Pending JPH10513468A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR95/01490		1995-02-09
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
JPH10513468A true JPH10513468A (ja)	1998-12-22

Family

ID=9475981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8524038A Pending JPH10513468A (ja)	1995-02-09	1996-02-07	ファルネシル転移酵素阻害剤、これらの調製、及びこれらを含む製薬学的組成

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)

Families Citing this family (63)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2730491B1 (fr) *	1995-02-09	1997-03-14	Rhone Poulenc Rorer Sa	Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent
US5972966A (en) *	1996-12-05	1999-10-26	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
US5932590A (en) *	1996-12-05	1999-08-03	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
US5977134A (en) *	1996-12-05	1999-11-02	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
US6015817A (en) *	1996-12-05	2000-01-18	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
FR2796943A1 (fr) *	1999-07-30	2001-02-02	Aventis Pharma Sa	Derives de benzoxazinnes, leur procede de preparation et leur utilisation en therapeutique
FR2796946A1 (fr) *	1999-07-30	2001-02-02	Aventis Pharma Sa	Nouveaux derives 8-carbonyl chromanes, leur preparation et leur utilisation en therapeutique
ES2382814T3 (es)	2005-05-17	2012-06-13	Merck Sharp & Dohme Ltd.	Ácido cis-4-[(4-clorofenil)sulfonil]-4-(2,5-difluorofenil)ciclohexanopropanoico para el tratamiento del cáncer
TWI387592B (zh)	2005-08-30	2013-03-01	Novartis Ag	經取代之苯并咪唑及其作為與腫瘤形成相關激酶之抑制劑之方法
GB0603041D0 (en)	2006-02-15	2006-03-29	Angeletti P Ist Richerche Bio	Therapeutic compounds
CA2649288C (en)	2006-04-19	2015-11-24	Novartis Ag	6-o-substituted benzoxazole and benzothiazole compounds and methods of inhibiting csf-1r signaling
US8173629B2 (en)	2006-09-22	2012-05-08	Merck Sharp & Dohme Corp.	Method of treatment using fatty acid synthesis inhibitors
US20110218176A1 (en)	2006-11-01	2011-09-08	Barbara Brooke Jennings-Spring	Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development
JP4611444B2 (ja)	2007-01-10	2011-01-12	イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー	ポリ（ａｄｐ−リボース）ポリメラーゼ（ｐａｒｐ）阻害剤としてのアミド置換インダゾール
CA2679659C (en)	2007-03-01	2016-01-19	Novartis Ag	Pim kinase inhibitors and methods of their use
AU2008254425A1 (en)	2007-05-21	2008-11-27	Novartis Ag	CSF-1R inhibitors, compositions, and methods of use
AU2008269154B2 (en)	2007-06-27	2014-06-12	Merck Sharp & Dohme Llc	4-carboxybenzylamino derivatives as histone deacetylase inhibitors
WO2010114780A1 (en)	2009-04-01	2010-10-07	Merck Sharp & Dohme Corp.	Inhibitors of akt activity
US8765747B2 (en)	2009-06-12	2014-07-01	Dana-Farber Cancer Institute, Inc.	Fused 2-aminothiazole compounds
PE20121172A1 (es)	2009-10-14	2012-09-05	Merck Sharp & Dohme	Piperidinas sustituidas con actividad en la hdm2
US8987275B2 (en)	2010-03-16	2015-03-24	Dana-Farber Cancer Institute, Inc.	Indazole compounds and their uses
WO2011163330A1 (en)	2010-06-24	2011-12-29	Merck Sharp & Dohme Corp.	Novel heterocyclic compounds as erk inhibitors
EP3330377A1 (de)	2010-08-02	2018-06-06	Sirna Therapeutics, Inc.	Durch rna-interferenz vermittelte hemmung der catenin (cadherin-assoziiertes protein)-beta-1 (ctnnb1)- genexpression mittels kurzer interferierender nukleinsäuren (sina)
US9029341B2 (en)	2010-08-17	2015-05-12	Sirna Therapeutics, Inc.	RNA interference mediated inhibition of hepatitis B virus (HBV) gene expression using short interfering nucleic acid (siNA)
US8883801B2 (en)	2010-08-23	2014-11-11	Merck Sharp & Dohme Corp.	Substituted pyrazolo[1,5-a]pyrimidines as mTOR inhibitors
EP2613782B1 (de)	2010-09-01	2016-11-02	Merck Sharp & Dohme Corp.	Indazolderivate als erk-hemmer
US9242981B2 (en)	2010-09-16	2016-01-26	Merck Sharp & Dohme Corp.	Fused pyrazole derivatives as novel ERK inhibitors
WO2012058210A1 (en)	2010-10-29	2012-05-03	Merck Sharp & Dohme Corp.	RNA INTERFERENCE MEDIATED INHIBITION OF GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACIDS (siNA)
WO2012087772A1 (en)	2010-12-21	2012-06-28	Schering Corporation	Indazole derivatives useful as erk inhibitors
AU2012245971A1 (en)	2011-04-21	2013-10-17	Piramal Enterprises Limited	A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation
EP2770987B1 (de)	2011-10-27	2018-04-04	Merck Sharp & Dohme Corp.	Neue verbindungen als erk-hemmer
US9382239B2 (en)	2011-11-17	2016-07-05	Dana-Farber Cancer Institute, Inc.	Inhibitors of c-Jun-N-terminal kinase (JNK)
US20150299696A1 (en)	2012-05-02	2015-10-22	Sirna Therapeutics, Inc.	SHORT INTERFERING NUCLEIC ACID (siNA) COMPOSITIONS
RU2660429C2 (ru)	2012-09-28	2018-07-06	Мерк Шарп И Доум Корп.	Новые соединения, которые являются ингибиторами erk
EP2909194A1 (de)	2012-10-18	2015-08-26	Dana-Farber Cancer Institute, Inc.	Hemmer der cyclinabhängigen kinase 7 (cdk7)
USRE48175E1 (en)	2012-10-19	2020-08-25	Dana-Farber Cancer Institute, Inc.	Hydrophobically tagged small molecules as inducers of protein degradation
RS56680B1 (sr)	2012-11-28	2018-03-30	Merck Sharp & Dohme	Kompozicije i postupci za lečenje kancera
KR102196882B1 (ko)	2012-12-20	2020-12-30	머크 샤프 앤드 돔 코포레이션	Hdm2 억제제로서의 치환된 이미다조피리딘
WO2014120748A1 (en)	2013-01-30	2014-08-07	Merck Sharp & Dohme Corp.	2,6,7,8 substituted purines as hdm2 inhibitors
WO2015034925A1 (en)	2013-09-03	2015-03-12	Moderna Therapeutics, Inc.	Circular polynucleotides
WO2015058126A1 (en)	2013-10-18	2015-04-23	Syros Pharmaceuticals, Inc.	Heteroaromatic compounds useful for the treatment of prolferative diseases
EP3057956B1 (de)	2013-10-18	2021-05-05	Dana-Farber Cancer Institute, Inc.	Polycyclische inhibitoren der cyclin-dependent-kinase 7 (cdk7)
US9862688B2 (en)	2014-04-23	2018-01-09	Dana-Farber Cancer Institute, Inc.	Hydrophobically tagged janus kinase inhibitors and uses thereof
WO2015164614A1 (en)	2014-04-23	2015-10-29	Dana-Farber Cancer Institute, Inc.	Janus kinase inhibitors and uses thereof
JO3589B1 (ar)	2014-08-06	2020-07-05	Novartis Ag	مثبطات كيناز البروتين c وطرق استخداماتها
JP6854762B2 (ja)	2014-12-23	2021-04-07	ダナ−ファーバーキャンサーインスティテュート，インコーポレイテッド	サイクリン依存性キナーゼ７（ｃｄｋ７）の阻害剤
USRE50776E1 (en)	2015-03-27	2026-02-03	Dana-Farber Cancer Institute, Inc.	Inhibitors of cyclin-dependent kinases
WO2016201370A1 (en)	2015-06-12	2016-12-15	Dana-Farber Cancer Institute, Inc.	Combination therapy of transcription inhibitors and kinase inhibitors
AU2016319125B2 (en)	2015-09-09	2021-04-08	Dana-Farber Cancer Institute, Inc.	Inhibitors of cyclin-dependent kinases
JOP20190055A1 (ar)	2016-09-26	2019-03-24	Merck Sharp & Dohme	أجسام مضادة ضد cd27
EP3525785B1 (de)	2016-10-12	2025-08-27	Merck Sharp & Dohme LLC	Kdm5-inhibitoren
KR102702926B1 (ko)	2017-04-13	2024-09-06	사이로파 비.브이.	항-sirp 알파 항체
US10947234B2 (en)	2017-11-08	2021-03-16	Merck Sharp & Dohme Corp.	PRMT5 inhibitors
EP3706747B1 (de)	2017-11-08	2025-09-03	Merck Sharp & Dohme LLC	Prmt5-inhibitoren
WO2019148412A1 (en)	2018-02-01	2019-08-08	Merck Sharp & Dohme Corp.	Anti-pd-1/lag3 bispecific antibodies
US11981701B2 (en)	2018-08-07	2024-05-14	Merck Sharp & Dohme Llc	PRMT5 inhibitors
US12552826B2 (en)	2018-08-07	2026-02-17	Merck Sharp & Dohme Llc	PRMT5 inhibitors
US12173026B2 (en)	2018-08-07	2024-12-24	Merck Sharp & Dohme Llc	PRMT5 inhibitors
EP3833668B1 (de)	2018-08-07	2025-03-19	Merck Sharp & Dohme LLC	Prmt5-inhibitoren
US12441730B2 (en)	2019-12-17	2025-10-14	Merck Sharp & Dohme Llc	PRMT5 inhibitors
BR112022012015A2 (pt)	2019-12-17	2022-08-30	Merck Sharp & Dohme Llc	Inibidores de prmt5
EP4673747A1 (de)	2023-03-02	2026-01-07	CARCIMUN BIOTECH GmbH	Mittel und verfahren zur diagnose von krebs und/oder einer akuten entzündungskrankheit
WO2026027944A1 (en)	2024-07-30	2026-02-05	Sairopa B.V.	Anti-sirp alpha antibody formulations and uses thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
CZ249997A3 (en)	1997-11-12
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
JPH10513468A (ja)	1998-12-22	ファルネシル転移酵素阻害剤、これらの調製、及びこれらを含む製薬学的組成
JPH10513467A (ja)	1998-12-22	ファルネシル転移酵素阻害剤、これらの調製、及びこれらを含む製薬学的組成物
US10806798B2 (en)	2020-10-20	Compound with effects of thrombolysis, free radical scavenging and thrombus-targeting
AU675946B2 (en)	1997-02-27	Cyclic adhesion inhibitors
JPH10512560A (ja)	1998-12-02	新規なファルネシルトランスフェラーゼ阻害剤、その製造及びそれを含有する製薬学的組成物
JPH11508911A (ja)	1999-08-03	新規ファルネシルトランスフェラーゼ阻害剤、それらの製造および該阻害剤を含む医薬組成物
TW487708B (en)	2002-05-21	Acylguanidine derivatives and their use as serine protease inhibitors
EP0675112A1 (de)	1995-10-04	Imidazol-enthaltende Farnesyl-Protein-Transferase-Inhibitoren
EP0696593A2 (de)	1996-02-14	Inhibitoren der farnesyl protein Transferase
CN101180071A (zh)	2008-05-14	抑制蛋白酶体的组合物
IE873383L (en)	1988-06-15	Phosphinic acid derivatives
AU2021434797B2 (en)	2025-03-13	Amino acid derivative, preparation method therefor, and pharmaceutical composition for treating hepatitis, comprising same
IE63996B1 (en)	1995-06-28	Pharmaceutical formulations
JP2014088402A (ja)	2014-05-15	Ｃ末端におけるポリペプチドの結合
CZ108496A3 (en)	1996-12-11	Anti-thrombotic azacycloalkylalkanoyl peptides and pseudopeptides
WO2020072860A1 (en)	2020-04-09	Niraparib solid state form
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
JPS58116471A (ja)	1983-07-11	４−ヒドロキシメチル−１−フタラゾンエステル誘導体およびその塩
JP4601118B2 (ja)	2010-12-22	炎症性疾患治療剤
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
WO2026052678A1 (en)	2026-03-12	Anticancer compounds
GB1568195A (en)	1980-05-29	Synthetc peptides