ZA200104233B - Tricyclic farnesyl protein transferase inhibitors. - Google Patents
Tricyclic farnesyl protein transferase inhibitors. Download PDFInfo
- Publication number
- ZA200104233B ZA200104233B ZA200104233A ZA200104233A ZA200104233B ZA 200104233 B ZA200104233 B ZA 200104233B ZA 200104233 A ZA200104233 A ZA 200104233A ZA 200104233 A ZA200104233 A ZA 200104233A ZA 200104233 B ZA200104233 B ZA 200104233B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- substituted
- aryl
- cycloalkyl
- arylalkyl
- Prior art date
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- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 132
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 75
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 30
- 210000004881 tumor cell Anatomy 0.000 claims description 30
- -1 dihalo Chemical group 0.000 claims description 28
- 150000001721 carbon Chemical group 0.000 claims description 25
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
- 102000004357 Transferases Human genes 0.000 claims description 17
- 108090000992 Transferases Proteins 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 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 claims description 16
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 102000016914 ras Proteins Human genes 0.000 claims description 15
- 108010014186 ras Proteins Proteins 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000001408 amides Chemical group 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 210000004027 cell Anatomy 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 5
- 230000035772 mutation Effects 0.000 claims description 5
- 206010005003 Bladder cancer Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 201000009030 Carcinoma Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
- 201000001531 bladder carcinoma Diseases 0.000 claims description 4
- 230000003325 follicular Effects 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 208000025113 myeloid leukemia Diseases 0.000 claims description 4
- 231100000590 oncogenic Toxicity 0.000 claims description 4
- 230000002246 oncogenic effect Effects 0.000 claims description 4
- 108700042226 ras Genes Proteins 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 210000001685 thyroid gland Anatomy 0.000 claims description 4
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 101150040459 RAS gene Proteins 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 14
- 239000000126 substance Substances 0.000 claims 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 claims 3
- 210000000066 myeloid cell Anatomy 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 201000002528 pancreatic cancer Diseases 0.000 claims 3
- 208000023958 prostate neoplasm Diseases 0.000 claims 3
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 2
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 claims 2
- 101150075558 CHGA gene Proteins 0.000 claims 1
- 101100205892 Caenorhabditis elegans taf-2 gene Proteins 0.000 claims 1
- 102100035591 POU domain, class 2, transcription factor 2 Human genes 0.000 claims 1
- 101710084411 POU domain, class 2, transcription factor 2 Proteins 0.000 claims 1
- 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 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002837 carbocyclic group Chemical group 0.000 description 6
- 230000002159 abnormal effect Effects 0.000 description 5
- 230000010261 cell growth Effects 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000002062 proliferating effect Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 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 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 230000001131 transforming effect Effects 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108091006027 G proteins Proteins 0.000 description 2
- 102000030782 GTP binding Human genes 0.000 description 2
- 108091000058 GTP-Binding Proteins 0.000 description 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 2
- 108700020796 Oncogene Proteins 0.000 description 2
- 102000043276 Oncogene Human genes 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 2
- 230000003211 malignant effect Effects 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
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
- 206010048832 Colon adenoma Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000009905 Neurofibromatoses Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 238000000170 chemical ionisation mass spectrum Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 201000010897 colon adenocarcinoma Diseases 0.000 description 1
- 230000030944 contact inhibition Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 230000006126 farnesylation Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000006122 isoprenylation Effects 0.000 description 1
- 201000005249 lung adenocarcinoma Diseases 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 201000004931 neurofibromatosis Diseases 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 230000008844 regulatory mechanism Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Electroluminescent Light Sources (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21639898A | 1998-12-18 | 1998-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200104233B true ZA200104233B (en) | 2002-08-22 |
Family
ID=22806914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200104233A ZA200104233B (en) | 1998-12-18 | 2001-05-23 | Tricyclic farnesyl protein transferase inhibitors. |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1140902A1 (OSRAM) |
| JP (1) | JP2002533336A (OSRAM) |
| KR (1) | KR20010081116A (OSRAM) |
| CN (1) | CN1326850C (OSRAM) |
| AR (1) | AR021718A1 (OSRAM) |
| AU (1) | AU776558B2 (OSRAM) |
| BR (1) | BR9916314A (OSRAM) |
| CA (1) | CA2354779A1 (OSRAM) |
| CO (1) | CO5160350A1 (OSRAM) |
| CZ (1) | CZ20011950A3 (OSRAM) |
| HU (1) | HUP0202152A2 (OSRAM) |
| IL (1) | IL143408A0 (OSRAM) |
| NO (1) | NO20012961L (OSRAM) |
| NZ (1) | NZ511878A (OSRAM) |
| PE (1) | PE20001342A1 (OSRAM) |
| PL (1) | PL348293A1 (OSRAM) |
| SK (1) | SK7592001A3 (OSRAM) |
| TR (1) | TR200101755T2 (OSRAM) |
| WO (1) | WO2000037459A1 (OSRAM) |
| ZA (1) | ZA200104233B (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR021718A1 (es) | 1998-12-18 | 2002-07-31 | Schering Corp | Inhibidores de transferasa de proteina farnesilo. |
| US7342016B2 (en) | 2000-08-30 | 2008-03-11 | Schering Corporation | Farnesyl protein transferase inhibitors as antitumor agents |
| AU2002236813A1 (en) * | 2001-01-22 | 2002-07-30 | Schering Corporation | Treatment of malaria with farnesyl protein transferase inhibitors |
| AU2002257114A1 (en) * | 2001-04-06 | 2002-10-21 | Schering Corporation | Treatment of malaria with farsenyl protein transferase inhibitors |
| US7585864B2 (en) | 2004-12-13 | 2009-09-08 | Schering Corporation | Farnesyl protein transferase inhibitors and their use to treat cancer |
| EP1833481A1 (en) | 2004-12-14 | 2007-09-19 | Schering Corporation | Farnesyl protein transferase inhibitors and methods for treating proliferative diseases |
| CA2637572A1 (en) * | 2006-01-19 | 2007-07-26 | Schering Corporation | Piperazine derivatives as farnesyl protein transferase inhibitors |
| JP6613391B2 (ja) * | 2014-03-19 | 2019-12-04 | ブイピーエス‐３，インコーポレイテッド | ２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−１−（５−置換ピリジン−２−イル）−３−（１ｈ−テトラゾール−１−イル）プロパン−２−オールおよびその調製工程 |
| CN109678791B (zh) | 2014-03-19 | 2022-07-01 | 美国陶氏益农公司 | 1-(2,4-二氟苯)-2,2-二氟-2-(5-取代吡啶-2-基)乙酮及制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL111235A (en) * | 1993-10-15 | 2001-03-19 | Schering Plough Corp | Medicinal preparations for inhibiting protein G activity and for the treatment of malignant diseases, containing tricyclic compounds, some such new compounds and a process for the preparation of some of them |
| US5712280A (en) | 1995-04-07 | 1998-01-27 | Schering Corporation | Tricyclic compounds useful for inhibition of G-protein function and for treatment of proliferative diseases |
| 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 |
| US5801175A (en) * | 1995-04-07 | 1998-09-01 | Schering Corporation | Tricyclic compounds useful for inhibition of G-protein function and for treatment of proliferative diseases |
| PE92098A1 (es) * | 1996-07-31 | 1998-12-31 | Schering Corp | N-cianoiminas triciclicas utiles como inhibidores de transferasa de proteina farnesilo |
| KR100640672B1 (ko) | 1997-06-17 | 2006-11-02 | 파마코페이아 드럭 디스커버리, 인크. | 파르네실 단백질 트랜스퍼라제의 억제에 유용한 벤즈피리도 사이클로헵탄 화합물 및 이를 포함하는 약제학적 조성물 |
| AR021718A1 (es) | 1998-12-18 | 2002-07-31 | Schering Corp | Inhibidores de transferasa de proteina farnesilo. |
-
1999
- 1999-12-16 AR ARP990106461A patent/AR021718A1/es unknown
- 1999-12-16 SK SK759-2001A patent/SK7592001A3/sk unknown
- 1999-12-16 CN CNB99816206XA patent/CN1326850C/zh not_active Expired - Fee Related
- 1999-12-16 CZ CZ20011950A patent/CZ20011950A3/cs unknown
- 1999-12-16 BR BR9916314-4A patent/BR9916314A/pt not_active IP Right Cessation
- 1999-12-16 EP EP99963980A patent/EP1140902A1/en not_active Withdrawn
- 1999-12-16 WO PCT/US1999/027939 patent/WO2000037459A1/en not_active Ceased
- 1999-12-16 PL PL99348293A patent/PL348293A1/xx not_active Application Discontinuation
- 1999-12-16 TR TR2001/01755T patent/TR200101755T2/xx unknown
- 1999-12-16 JP JP2000589531A patent/JP2002533336A/ja active Pending
- 1999-12-16 CA CA002354779A patent/CA2354779A1/en not_active Abandoned
- 1999-12-16 HU HU0202152A patent/HUP0202152A2/hu unknown
- 1999-12-16 IL IL14340899A patent/IL143408A0/xx unknown
- 1999-12-16 AU AU20307/00A patent/AU776558B2/en not_active Ceased
- 1999-12-16 CO CO99078843A patent/CO5160350A1/es unknown
- 1999-12-16 NZ NZ511878A patent/NZ511878A/en unknown
- 1999-12-16 KR KR1020017007632A patent/KR20010081116A/ko not_active Abandoned
- 1999-12-17 PE PE1999001295A patent/PE20001342A1/es not_active Application Discontinuation
-
2001
- 2001-05-23 ZA ZA200104233A patent/ZA200104233B/en unknown
- 2001-06-15 NO NO20012961A patent/NO20012961L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CO5160350A1 (es) | 2002-05-30 |
| CA2354779A1 (en) | 2000-06-29 |
| TR200101755T2 (tr) | 2001-09-21 |
| BR9916314A (pt) | 2001-10-02 |
| HUP0202152A2 (en) | 2002-10-28 |
| NO20012961D0 (no) | 2001-06-15 |
| PE20001342A1 (es) | 2000-12-09 |
| CN1326850C (zh) | 2007-07-18 |
| AU2030700A (en) | 2000-07-12 |
| EP1140902A1 (en) | 2001-10-10 |
| JP2002533336A (ja) | 2002-10-08 |
| AU776558B2 (en) | 2004-09-16 |
| CZ20011950A3 (cs) | 2001-12-12 |
| IL143408A0 (en) | 2002-04-21 |
| NO20012961L (no) | 2001-08-16 |
| PL348293A1 (en) | 2002-05-20 |
| WO2000037459A1 (en) | 2000-06-29 |
| NZ511878A (en) | 2003-10-31 |
| KR20010081116A (ko) | 2001-08-27 |
| SK7592001A3 (en) | 2002-03-05 |
| AR021718A1 (es) | 2002-07-31 |
| CN1334811A (zh) | 2002-02-06 |
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