IL127575A - Compounds with inhibitory activity of perennial transferases and preparations containing them - Google Patents

Compounds with inhibitory activity of perennial transferases and preparations containing them

Info

Publication number: IL127575A
Authority: IL; Israel
Prior art keywords: compound; lower alkyl; pharmaceutically acceptable; acceptable salt; aryl
Prior art date: 1996-06-28

Application number

IL12757597A

Other languages

English (en)

Hebrew (he)

Other versions

IL127575A0 (en

Inventor

Sun H Kim

Original Assignee

Biomeasure Inc

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.)

1996-06-28

Filing date

1997-05-29

Publication date

2002-12-01

1997-05-29 Application filed by Biomeasure Inc filed Critical Biomeasure Inc

1999-10-28 Publication of IL127575A0 publication Critical patent/IL127575A0/xx

2002-12-01 Publication of IL127575A publication Critical patent/IL127575A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 62
230000002401 inhibitory effect Effects 0.000 title abstract description 3
239000000203 mixture Substances 0.000 title description 13
102000005454 Dimethylallyltranstransferase Human genes 0.000 title description 4
108010006731 Dimethylallyltranstransferase Proteins 0.000 title description 4
230000000694 effects Effects 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 25
125000004149 thio group Chemical group *S* 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 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 5
206010028980 Neoplasm Diseases 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
QJPWUUJVYOJNMH-VKHMYHEASA-N L-homoserine lactone Chemical compound N[C@H]1CCOC1=O QJPWUUJVYOJNMH-VKHMYHEASA-N 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 4
125000005418 aryl aryl group Chemical group 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
208000037803 restenosis Diseases 0.000 claims 1
102000019337 Prenyltransferases Human genes 0.000 abstract description 4
108050006837 Prenyltransferases Proteins 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
-1 aliphatic amino acid Chemical class 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
125000004122 cyclic group Chemical group 0.000 description 7
229940093499 ethyl acetate Drugs 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
LTRPJRSRZAQDQI-LURJTMIESA-N methyl (2s)-2-isocyanato-4-methylsulfanylbutanoate Chemical compound COC(=O)[C@@H](N=C=O)CCSC LTRPJRSRZAQDQI-LURJTMIESA-N 0.000 description 4
239000006187 pill Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
JGELLTGLGPWSRM-RFHHWMCGSA-N methyl (2S)-2-amino-4-methylsulfanyl-5-oxo-5-[(3S)-1,2,3,4-tetrahydroisoquinolin-3-yl]pentanoate Chemical compound COC([C@@H](N)CC(SC)C(=O)[C@H]1NCC2=CC=CC=C2C1)=O JGELLTGLGPWSRM-RFHHWMCGSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000019491 signal transduction Effects 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
VJQYDEIDLSTCEA-YFKPBYRVSA-N (2s)-2-isocyanato-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)N=C=O VJQYDEIDLSTCEA-YFKPBYRVSA-N 0.000 description 2
LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 2
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 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
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 2
150000001413 amino acids Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000004899 c-terminal region Anatomy 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
210000000170 cell membrane Anatomy 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000010549 co-Evaporation Methods 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
235000018417 cysteine Nutrition 0.000 description 2
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
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 2
239000006260 foam Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
210000004211 gastric acid Anatomy 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000000968 intestinal effect Effects 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
239000001095 magnesium carbonate Substances 0.000 description 2
229910000021 magnesium carbonate Inorganic materials 0.000 description 2
239000000693 micelle Substances 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
229960001639 penicillamine Drugs 0.000 description 2
150000003904 phospholipids Chemical class 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
235000018102 proteins Nutrition 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
210000000813 small intestine Anatomy 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
BVIZOEBRLRZHGI-XMMPIXPASA-N tert-butyl n-[(2r)-1-oxo-3-tritylsulfanylpropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](NC(=O)OC(C)(C)C)C=O)C1=CC=CC=C1 BVIZOEBRLRZHGI-XMMPIXPASA-N 0.000 description 2
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 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
239000003558 transferase inhibitor Substances 0.000 description 2
ATVFTGTXIUDKIZ-YFKPBYRVSA-N (2r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-sulfanylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](CS)C(O)=O ATVFTGTXIUDKIZ-YFKPBYRVSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
BWKMGYQJPOAASG-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CNC(C(=O)O)CC2=C1 BWKMGYQJPOAASG-UHFFFAOYSA-N 0.000 description 1
XXMFJKNOJSDQBM-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrate Chemical compound [OH3+].[O-]C(=O)C(F)(F)F XXMFJKNOJSDQBM-UHFFFAOYSA-N 0.000 description 1
VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
OINNEUNVOZHBOX-QIRCYJPOSA-K 2-trans,6-trans,10-trans-geranylgeranyl diphosphate(3-) Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP([O-])(=O)OP([O-])([O-])=O OINNEUNVOZHBOX-QIRCYJPOSA-K 0.000 description 1
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
125000001433 C-terminal amino-acid group Chemical group 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
OINNEUNVOZHBOX-XBQSVVNOSA-N Geranylgeranyl diphosphate Natural products [P@](=O)(OP(=O)(O)O)(OC/C=C(\CC/C=C(\CC/C=C(\CC/C=C(\C)/C)/C)/C)/C)O OINNEUNVOZHBOX-XBQSVVNOSA-N 0.000 description 1
229910004373 HOAc Inorganic materials 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
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000699660 Mus musculus Species 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
206010061902 Pancreatic neoplasm Diseases 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
229940121659 Prenyltransferase inhibitor Drugs 0.000 description 1
102000004357 Transferases Human genes 0.000 description 1
108090000992 Transferases Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
239000002585 base Substances 0.000 description 1
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000004305 biphenyl Chemical group 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
230000037396 body weight Effects 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
201000011510 cancer Diseases 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940125833 compound 23 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
210000000172 cytosol Anatomy 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
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239000000839 emulsion Substances 0.000 description 1
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000002686 geranylgeranyl 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])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000012010 growth Effects 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000004807 localization Effects 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
230000001404 mediated effect Effects 0.000 description 1
125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 1
KXWULRSLTPLVDC-ZDUSSCGKSA-N methyl (2s)-2-(isoquinoline-1-carbonylamino)-4-methylsulfanylbutanoate Chemical compound C1=CC=C2C(C(=O)N[C@@H](CCSC)C(=O)OC)=NC=CC2=C1 KXWULRSLTPLVDC-ZDUSSCGKSA-N 0.000 description 1
MEVUPUNLVKELNV-JEDNCBNOSA-N methyl (2s)-2-amino-4-methylsulfanylbutanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CCSC MEVUPUNLVKELNV-JEDNCBNOSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000011580 nude mouse model Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
231100000590 oncogenic Toxicity 0.000 description 1
230000002246 oncogenic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
230000004481 post-translational protein modification Effects 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
238000005070 sampling Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
GZDULWNQNLIERR-AREMUKBSSA-N tert-butyl n-[(2r)-1-oxo-4,4,4-triphenyl-2-sulfanylbutan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C[C@](S)(NC(=O)OC(C)(C)C)C=O)C1=CC=CC=C1 GZDULWNQNLIERR-AREMUKBSSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/36—Seven-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/38—Eight-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
- 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
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
- 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
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/081—Tripeptides 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Biophysics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

IL12757597A 1996-06-28 1997-05-29 Compounds with inhibitory activity of perennial transferases and preparations containing them IL127575A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/675,439 US5767274A (en)	1996-06-28	1996-06-28	Prenyl transferase inhibitors
PCT/US1997/009413 WO1998000411A1 (en)	1996-06-28	1997-05-29	Prenyl transferase inhibitors

Publications (2)

Publication Number	Publication Date
IL127575A0 IL127575A0 (en)	1999-10-28
IL127575A true IL127575A (en)	2002-12-01

Family

ID=24710505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12757597A IL127575A (en)	1996-06-28	1997-05-29	Compounds with inhibitory activity of perennial transferases and preparations containing them

Country Status (18)

Country	Link
US (1)	US5767274A (de)
EP (2)	EP1676855A3 (de)
JP (1)	JP4073491B2 (de)
KR (1)	KR20000022305A (de)
CN (1)	CN1091766C (de)
AT (1)	ATE359290T1 (de)
CA (1)	CA2255893A1 (de)
CZ (1)	CZ296248B6 (de)
DE (1)	DE69737609T2 (de)
ES (1)	ES2283017T3 (de)
IL (1)	IL127575A (de)
NZ (1)	NZ332560A (de)
PL (1)	PL190852B1 (de)
PT (1)	PT1015439E (de)
RU (1)	RU2201925C2 (de)
TW (1)	TW503240B (de)
WO (1)	WO1998000411A1 (de)
ZA (1)	ZA975728B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5299915A (en) *	1992-07-15	1994-04-05	General Electric Corporation	Bucket for the last stage of a steam turbine
US6180619B1 (en) *	1996-06-28	2001-01-30	Biomeasure, Incorporated	Prenyl transferase inhibitors
US7932036B1 (en)	2008-03-12	2011-04-26	Veridex, Llc	Methods of determining acute myeloid leukemia response to treatment with farnesyltransferase
WO2009148709A1 (en) *	2008-04-16	2009-12-10	University Of Utah Research Foundation	Pharmacological targeting of vascular malformations
CA2806112C (en)	2010-07-28	2023-03-21	Veridex, Llc	Methods of determining acute myeloid leukemia response to treatment with farnesyltransferase inhibitors
EA201890512A1 (ru)	2015-08-17	2018-09-28	Кура Онколоджи, Инк.	Способы лечения пациентов со злокачественными опухолями с использованием ингибиторов фарнезилтрансферазы
RS61745B1 (sr)	2016-11-03	2021-05-31	Kura Oncology Inc	Inhibitori farneziltransferaze za upotrebu u tretiranju kancera
WO2019113269A1 (en)	2017-12-08	2019-06-13	Kura Oncology, Inc.	Methods of treating cancer patients with farnesyltransferase inhibitors
US20220143006A1 (en)	2019-03-15	2022-05-12	Kura Oncology, Inc.	Methods of treating cancer with farnesyltransferase inhibitors

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5043345A (en) *	1989-02-22	1991-08-27	Novo Nordisk A/S	Piperidine compounds and their preparation and use
US5141851A (en) *	1990-04-18	1992-08-25	Board Of Regents, The University Of Texas System	Isolated farnesyl protein transferase enzyme
US5536737A (en) *	1992-11-20	1996-07-16	Japan Tobacco Inc.	Compound having prolyl endopeptidase inhibitory activity and pharmaceutical use thereof
CA2118985A1 (en) *	1993-04-02	1994-10-03	Dinesh V. Patel	Heterocyclic inhibitors of farnesyl protein transferase
EP0648205B1 (de) *	1993-04-27	1999-07-14	Celltech Therapeutics Limited	Peptidylderivate als inhibitoren von metalloproteinase
WO1995000497A1 (en) *	1993-06-18	1995-01-05	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
US5486623A (en) *	1993-12-08	1996-01-23	Prototek, Inc.	Cysteine protease inhibitors containing heterocyclic leaving groups
US5439918A (en) *	1994-03-14	1995-08-08	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
CA2155448A1 (en) *	1994-08-11	1996-02-12	Katerina Leftheris	Inhibitors of farnesyl protein transferase
US5491164A (en) *	1994-09-29	1996-02-13	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
IL117798A (en) *	1995-04-07	2001-11-25	Schering Plough Corp	Tricyclic compounds useful for inhibiting the function of protein - G and for the treatment of malignant diseases, and pharmaceutical preparations containing them

1996
- 1996-06-28 US US08/675,439 patent/US5767274A/en not_active Expired - Fee Related
1997
- 1997-05-29 WO PCT/US1997/009413 patent/WO1998000411A1/en not_active Ceased
- 1997-05-29 EP EP06005859A patent/EP1676855A3/de not_active Withdrawn
- 1997-05-29 KR KR1019980710727A patent/KR20000022305A/ko not_active Ceased
- 1997-05-29 IL IL12757597A patent/IL127575A/en not_active IP Right Cessation
- 1997-05-29 PT PT97926849T patent/PT1015439E/pt unknown
- 1997-05-29 JP JP50412598A patent/JP4073491B2/ja not_active Expired - Fee Related
- 1997-05-29 EP EP97926849A patent/EP1015439B1/de not_active Expired - Lifetime
- 1997-05-29 NZ NZ332560A patent/NZ332560A/en unknown
- 1997-05-29 DE DE69737609T patent/DE69737609T2/de not_active Expired - Fee Related
- 1997-05-29 CA CA002255893A patent/CA2255893A1/en not_active Abandoned
- 1997-05-29 AT AT97926849T patent/ATE359290T1/de not_active IP Right Cessation
- 1997-05-29 PL PL330786A patent/PL190852B1/pl unknown
- 1997-05-29 CN CN97195839A patent/CN1091766C/zh not_active Expired - Fee Related
- 1997-05-29 CZ CZ0417898A patent/CZ296248B6/cs not_active IP Right Cessation
- 1997-05-29 ES ES97926849T patent/ES2283017T3/es not_active Expired - Lifetime
- 1997-05-29 RU RU99101793/04A patent/RU2201925C2/ru not_active IP Right Cessation
- 1997-06-27 ZA ZA9705728A patent/ZA975728B/xx unknown
- 1997-06-28 TW TW086109108A patent/TW503240B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA975728B (en)	1998-01-26
WO1998000411A1 (en)	1998-01-08
IL127575A0 (en)	1999-10-28
ATE359290T1 (de)	2007-05-15
PT1015439E (pt)	2007-05-31
KR20000022305A (ko)	2000-04-25
JP2001500844A (ja)	2001-01-23
PL330786A1 (en)	1999-06-07
EP1015439A1 (de)	2000-07-05
US5767274A (en)	1998-06-16
CZ417898A3 (cs)	1999-05-12
CN1223643A (zh)	1999-07-21
NZ332560A (en)	2000-02-28
EP1015439B1 (de)	2007-04-11
EP1676855A3 (de)	2006-07-26
CN1091766C (zh)	2002-10-02
EP1676855A2 (de)	2006-07-05
AU715475B2 (en)	2000-02-03
EP1015439A4 (de)	2001-10-17
TW503240B (en)	2002-09-21
CA2255893A1 (en)	1998-01-08
JP4073491B2 (ja)	2008-04-09
AU3151697A (en)	1998-01-21
DE69737609T2 (de)	2007-12-20
CZ296248B6 (cs)	2006-02-15
ES2283017T3 (es)	2007-10-16
RU2201925C2 (ru)	2003-04-10
PL190852B1 (pl)	2006-02-28
DE69737609D1 (de)	2007-05-24

Legal Events

Date	Code	Title
2003-05-29	FF	Patent granted
2003-06-24	FF	Patent granted
2003-07-06	KB	Patent renewed
2008-01-22	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US5773455A (en)	1998-06-30	Inhibitors of prenyl transferases
EP1015439B1 (de)	2007-04-11	Prenyl transferase inhibitoren
US6180619B1 (en)	2001-01-30	Prenyl transferase inhibitors
AU715475C (en)	2000-10-19	Prenyl transferase inhibitors
KR100491433B1 (ko)	2005-11-21	프레닐전이효소의저해제
KR20050019003A (ko)	2005-02-28	프레닐 전이효소 저해제
KR20050019004A (ko)	2005-02-28	프레닐 전이효소 저해제
HK1032002B (en)	2006-06-02	Prenyl transferase inhibitors
HUP9903611A2 (hu)	2000-02-28	Prenil-transzferáz-inhibitorok
MXPA98010693A (en)	1999-09-20	Inhibitors of the prenyl-transfer