UA73572C2 - 1,2-annelated quinoline enantiomer inhibiting farnesyl transferase - Google Patents

1,2-annelated quinoline enantiomer inhibiting farnesyl transferase Download PDF

Info

Publication number: UA73572C2
Authority: UA; Ukraine
Prior art keywords: compound; mixture; chlorophenyl; cancer; farnesyl transferase
Prior art date: 2000-06-22

Application number

UA20021210152A

Other languages

English (en)

Ukrainian (uk)

Inventor

Patrick Rene Angibaud

David William End

Original Assignee

Janssen Pharmaceutica Nv

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.)

2000-06-22

Filing date

2001-06-13

Publication date

2005-08-15

2001-06-13 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2005-08-15 Publication of UA73572C2 publication Critical patent/UA73572C2/uk

Links

230000002401 inhibitory effect Effects 0.000 title description 9
102000007317 Farnesyltranstransferase Human genes 0.000 title 1
108010007508 Farnesyltranstransferase Proteins 0.000 title 1
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract description 28
206010028980 Neoplasm Diseases 0.000 abstract description 13
201000011510 cancer Diseases 0.000 abstract description 4
239000003814 drug Substances 0.000 abstract description 4
239000002253 acid Substances 0.000 abstract description 3
150000003839 salts Chemical class 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
239000002552 dosage form Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000007789 gas Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
201000010099 disease Diseases 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
108700020796 Oncogene Proteins 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
230000000259 anti-tumor effect Effects 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
230000002062 proliferating effect Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
230000004614 tumor growth Effects 0.000 description 4
102000043276 Oncogene Human genes 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
102000004357 Transferases Human genes 0.000 description 3
108090000992 Transferases Proteins 0.000 description 3
230000002159 abnormal effect Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
230000010261 cell growth Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
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 3
-1 for example Chemical compound 0.000 description 3
230000035772 mutation Effects 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000006187 pill Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
210000004881 tumor cell Anatomy 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
208000003456 Juvenile Arthritis Diseases 0.000 description 2
201000003793 Myelodysplastic syndrome Diseases 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000033115 angiogenesis Effects 0.000 description 2
238000003556 assay Methods 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
208000029742 colonic neoplasm Diseases 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 2
239000008103 glucose Substances 0.000 description 2
230000012010 growth Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000003211 malignant effect Effects 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
231100000590 oncogenic Toxicity 0.000 description 2
230000002246 oncogenic effect Effects 0.000 description 2
208000008443 pancreatic carcinoma Diseases 0.000 description 2
230000008447 perception Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 2
208000011581 secondary neoplasm Diseases 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
201000000596 systemic lupus erythematosus Diseases 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 1
JIVOQELLDZQRDZ-UHFFFAOYSA-N 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1h-quinazolin-2-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(NC(=O)N=C2C=3C=C(Cl)C=CC=3)C2=C1 JIVOQELLDZQRDZ-UHFFFAOYSA-N 0.000 description 1
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
208000002874 Acne Vulgaris Diseases 0.000 description 1
208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
208000031261 Acute myeloid leukaemia Diseases 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
206010003694 Atrophy Diseases 0.000 description 1
208000003950 B-cell lymphoma Diseases 0.000 description 1
208000009137 Behcet syndrome Diseases 0.000 description 1
206010005003 Bladder cancer Diseases 0.000 description 1
206010006458 Bronchitis chronic Diseases 0.000 description 1
208000011691 Burkitt lymphomas Diseases 0.000 description 1
GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 1
GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 1
DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
206010048832 Colon adenoma Diseases 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
208000001333 Colorectal Neoplasms Diseases 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
201000003883 Cystic fibrosis Diseases 0.000 description 1
102000004127 Cytokines Human genes 0.000 description 1
108090000695 Cytokines Proteins 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
206010012434 Dermatitis allergic Diseases 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
206010013908 Dysfunctional uterine bleeding Diseases 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
201000009273 Endometriosis Diseases 0.000 description 1
229940102550 Estrogen receptor antagonist Drugs 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
208000010201 Exanthema Diseases 0.000 description 1
201000008808 Fibrosarcoma Diseases 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
206010018338 Glioma Diseases 0.000 description 1
208000009329 Graft vs Host Disease Diseases 0.000 description 1
208000031886 HIV Infections Diseases 0.000 description 1
XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
206010023347 Keratoacanthoma Diseases 0.000 description 1
208000008839 Kidney Neoplasms Diseases 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
101710158865 Large delta antigen Proteins 0.000 description 1
GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
206010027514 Metrorrhagia Diseases 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
206010029260 Neuroblastoma Diseases 0.000 description 1
208000009905 Neurofibromatoses Diseases 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
206010033128 Ovarian cancer Diseases 0.000 description 1
206010061535 Ovarian neoplasm Diseases 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
206010061902 Pancreatic neoplasm Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
208000020410 Psoriasis-related juvenile idiopathic arthritis Diseases 0.000 description 1
206010038389 Renal cancer Diseases 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
206010039085 Rhinitis allergic Diseases 0.000 description 1
206010039710 Scleroderma Diseases 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229940100389 Sulfonylurea Drugs 0.000 description 1
206010052779 Transplant rejections Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
206010046798 Uterine leiomyoma Diseases 0.000 description 1
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
241000863480 Vinca Species 0.000 description 1
108010067390 Viral Proteins Proteins 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
241000700605 Viruses Species 0.000 description 1
230000001594 aberrant effect Effects 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
206010000496 acne Diseases 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
208000009956 adenocarcinoma Diseases 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
201000010105 allergic rhinitis Diseases 0.000 description 1
208000004631 alopecia areata Diseases 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229960002932 anastrozole Drugs 0.000 description 1
YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
230000019552 anatomical structure morphogenesis Effects 0.000 description 1
229940045799 anthracyclines and related substance Drugs 0.000 description 1
229940045696 antineoplastic drug podophyllotoxin derivative Drugs 0.000 description 1
239000003886 aromatase inhibitor Substances 0.000 description 1
229940046844 aromatase inhibitors Drugs 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
201000008937 atopic dermatitis Diseases 0.000 description 1
230000037444 atrophy Effects 0.000 description 1
230000003305 autocrine Effects 0.000 description 1
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
206010004398 benign neoplasm of skin Diseases 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000008827 biological function Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
201000008275 breast carcinoma Diseases 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
229960004117 capecitabine Drugs 0.000 description 1
229960004562 carboplatin Drugs 0.000 description 1
229960005243 carmustine Drugs 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
229960004630 chlorambucil Drugs 0.000 description 1
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
208000007451 chronic bronchitis Diseases 0.000 description 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
201000010897 colon adenocarcinoma Diseases 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
230000030944 contact inhibition Effects 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 1
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
229940075894 denatured ethanol Drugs 0.000 description 1
201000001981 dermatomyositis Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
229960003668 docetaxel Drugs 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
229950004203 droloxifene Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000013020 embryo development Effects 0.000 description 1
201000006828 endometrial hyperplasia Diseases 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
229960005420 etoposide Drugs 0.000 description 1
201000005884 exanthem Diseases 0.000 description 1
229960000255 exemestane Drugs 0.000 description 1
201000007249 familial juvenile hyperuricemic nephropathy Diseases 0.000 description 1
229940087861 faslodex Drugs 0.000 description 1
229960002949 fluorouracil Drugs 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
229960005277 gemcitabine Drugs 0.000 description 1
230000030279 gene silencing Effects 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
208000024908 graft versus host disease Diseases 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
201000005787 hematologic cancer Diseases 0.000 description 1
208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
239000008172 hydrogenated vegetable oil Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229960000908 idarubicin Drugs 0.000 description 1
230000036737 immune function Effects 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229960004768 irinotecan Drugs 0.000 description 1
GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 1
201000004990 juvenile ankylosing spondylitis Diseases 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
201000010982 kidney cancer Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
201000010260 leiomyoma Diseases 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229960002247 lomustine Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
201000005202 lung cancer Diseases 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
229960004961 mechlorethamine Drugs 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
208000025113 myeloid leukemia Diseases 0.000 description 1
230000006654 negative regulation of apoptotic process Effects 0.000 description 1
230000006715 negative regulation of smooth muscle cell proliferation Effects 0.000 description 1
230000004770 neurodegeneration Effects 0.000 description 1
201000004931 neurofibromatosis Diseases 0.000 description 1
OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 1
208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
229940127084 other anti-cancer agent Drugs 0.000 description 1
230000002018 overexpression Effects 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
230000003076 paracrine Effects 0.000 description 1
230000007170 pathology Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical class COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
239000003600 podophyllotoxin derivative Substances 0.000 description 1
208000019764 polyarticular juvenile idiopathic arthritis Diseases 0.000 description 1
208000030761 polycystic kidney disease Diseases 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000013823 prenylation Effects 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
229960004622 raloxifene Drugs 0.000 description 1
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
206010037844 rash Diseases 0.000 description 1
230000008844 regulatory mechanism Effects 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
230000002207 retinal effect Effects 0.000 description 1
201000009410 rhabdomyosarcoma Diseases 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
229940095743 selective estrogen receptor modulator Drugs 0.000 description 1
239000000333 selective estrogen receptor modulator Substances 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
229960001603 tamoxifen Drugs 0.000 description 1
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
229960001278 teniposide Drugs 0.000 description 1
208000001608 teratocarcinoma Diseases 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
229960005026 toremifene Drugs 0.000 description 1
XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
229960000575 trastuzumab Drugs 0.000 description 1
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
201000005112 urinary bladder cancer Diseases 0.000 description 1
230000002792 vascular Effects 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
229960002066 vinorelbine Drugs 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
229960001771 vorozole Drugs 0.000 description 1
XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Dermatology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Ophthalmology & Optometry (AREA)
Surgery (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

UA20021210152A 2000-06-22 2001-06-13 1,2-annelated quinoline enantiomer inhibiting farnesyl transferase UA73572C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00202181		2000-06-22
PCT/EP2001/006747 WO2001098302A1 (en)	2000-06-22	2001-06-13	Farnesyl transferase inhibiting 1,2-annelated quinoline enantiomer

Publications (1)

Publication Number	Publication Date
UA73572C2 true UA73572C2 (en)	2005-08-15

Family

ID=8171675

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20021210152A UA73572C2 (en)	2000-06-22	2001-06-13	1,2-annelated quinoline enantiomer inhibiting farnesyl transferase

Country Status (34)

Country	Link
US (3)	US20030114471A1 (xx)
EP (1)	EP1296984B1 (xx)
JP (1)	JP4919575B2 (xx)
KR (2)	KR100846370B1 (xx)
CN (1)	CN1207296C (xx)
AR (1)	AR030704A1 (xx)
AT (1)	ATE294804T1 (xx)
AU (3)	AU2001263962B2 (xx)
BG (1)	BG65894B1 (xx)
BR (1)	BRPI0111743B8 (xx)
CA (1)	CA2410232C (xx)
CZ (1)	CZ295278B6 (xx)
DE (1)	DE60110592T2 (xx)
EA (1)	EA005065B1 (xx)
EE (1)	EE04966B1 (xx)
EG (1)	EG24180A (xx)
ES (1)	ES2241830T3 (xx)
HK (1)	HK1058363A1 (xx)
HR (1)	HRP20020989B1 (xx)
HU (1)	HU229095B1 (xx)
IL (2)	IL153560A0 (xx)
IS (1)	IS2596B (xx)
JO (1)	JO2361B1 (xx)
MX (1)	MXPA02012845A (xx)
MY (1)	MY127734A (xx)
NO (1)	NO324494B1 (xx)
NZ (1)	NZ522481A (xx)
PA (1)	PA8519501A1 (xx)
PL (1)	PL209521B1 (xx)
SA (1)	SA01220349B1 (xx)
SK (1)	SK285699B6 (xx)
UA (1)	UA73572C2 (xx)
WO (1)	WO2001098302A1 (xx)
ZA (1)	ZA200210305B (xx)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003018135A1 (en)	2001-08-24	2003-03-06	Wyeth Holdings Corporation	Method of using 5-(arylsulfonyl)-,5-(arylsulfinyl), and 5-(arylsulfanyl)-thiazolidine-2,4-diones for inhibition of farnesyl-protein transferase
ATE336496T1 (de)	2002-04-15	2006-09-15	Janssen Pharmaceutica Nv	Farnesyl transferase hemmende tricyclische quinazolinederivate substitutiert mit kohlenstoff-gebundenen imidazolen oder triazolen
US20050003422A1 (en)	2003-07-01	2005-01-06	Mitch Reponi	Methods for assessing and treating cancer
US11311519B2 (en)	2014-05-01	2022-04-26	Eiger Biopharmaceuticals, Inc.	Treatment of hepatitis delta virus infection
US10076512B2 (en)	2014-05-01	2018-09-18	Eiger Biopharmaceuticals, Inc.	Treatment of hepatitis delta virus infection
WO2016090107A2 (en) *	2014-12-04	2016-06-09	Eiger Biopharmaceuticals, Inc.	Treatment of hepatitis delta virus infection
JP2018517673A (ja)	2015-04-21	2018-07-05	アイガー・バイオファーマシューティカルズ・インコーポレイテッドＥｉｇｅｒＢｉｏｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ．	ロナファルニブおよびリトナビルを含む医薬組成物
LT3277842T (lt)	2015-08-17	2019-10-25	Kura Oncology Inc	Vėžio pacientų gydymo būdai farneziltransferazės inhibitoriais
AR110031A1 (es)	2016-11-03	2019-02-13	Kura Oncology Inc	Métodos de tratamiento de pacientes con cáncer con inhibidores de farnesiltransferasa

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1519765A (en) *	1974-09-05	1978-08-02	Ici Ltd	Pesticidal dihydrotetrazolo(1,5a) quinazolines compositions and processes
US4141979A (en) *	1976-12-23	1979-02-27	Pfizer Inc.	Tetrazolo[a]quinazol-5-ones antiallergy and antiulcer agents
GB9513577D0 (en) *	1995-07-04	1995-09-06	Brotherwood Rodney J	Improvements in passenger carrying vehicles
TW349948B (en) *	1995-10-31	1999-01-11	Janssen Pharmaceutica Nv	Farnesyl transferase inhibiting 2-quinolone derivatives
DK0865440T3 (da) *	1995-12-08	2002-07-22	Janssen Pharmaceutica Nv	Farnesylproteinfransferaseinhiberende (imidazol-5-yl)-2-quinolinonderivater
AU715658B2 (en)	1996-04-03	2000-02-10	Merck & Co., Inc.	Inhibitors of farnesyl-protein transferase
TW591030B (en) *	1997-03-10	2004-06-11	Janssen Pharmaceutica Nv	Farnesyl transferase inhibiting 1,8-annelated quinolinone derivatives substituted with N- or C-linked imidazoles
ES2289783T3 (es) *	1997-04-25	2008-02-01	Janssen Pharmaceutica N.V.	Quinazolinonas que inhiben la farnesiltransferasa.
WO1998055124A1 (en)	1997-06-02	1998-12-10	Janssen Pharmaceutica N.V.	(imidazol-5-yl)methyl-2-quinolinone derivatives as inhibitors of smooth muscle cell proliferation
CA2336624C (en) *	1998-07-06	2008-10-21	Janssen Pharmaceutica N.V.	Farnesyl protein transferase inhibitors with in vivo radiosensitizing properties
HU229358B1 (en)	1998-07-06	2013-11-28	Janssen Pharmaceutica Nv	Farnesyl protein transferase inhibitors for treating arthropathies
CA2341739C (en) *	1998-08-27	2005-07-12	Pfizer Products Inc.	Quinolin-2-one derivatives useful as anticancer agents
ES2259237T3 (es) *	1998-08-27	2006-09-16	Pfizer Products Inc.	Derivados de quinolin-2-ona alquinilsustituidos utiles como agentes anticancerosos.
TR200101961T2 (tr) *	1998-12-23	2001-12-21	Janssen Pharmaceutica N.V.	1,2-halkalı kinolin türevleri
US6462201B1 (en) *	1998-12-29	2002-10-08	Isp Investments Inc.	Process for the production of N-vinyl-2-pyrrolidone by vinylation
OA11833A (en) *	1999-02-11	2005-08-23	Pfizer Prod Inc	Heteroaryl-substituted quinolin-2-one derivatives useful as anticancer agents.
HN2000000266A (es)	2000-01-21	2001-05-21	Pfizer Prod Inc	Compuesto anticanceroso y metodo de separacion de enantiomeros util para sintetizar dicho compuesto.
EP1267848B1 (en)	2000-02-24	2007-10-17	Janssen Pharmaceutica N.V.	Dosing regimen comprising a farnesyl protein transferase inhibitor for the treatment of cancer
EP1322644A1 (en)	2000-09-25	2003-07-02	Janssen Pharmaceutica N.V.	Farnesyl transferase inhibiting 6-heterocyclylmethyl quinolinone derivatives
WO2002024686A2 (en)	2000-09-25	2002-03-28	Janssen Pharmaceutica N.V.	Farnesyl transferase inhibiting 6-heterocyclylmethyl quinoline and quinazoline derivatives

2001
- 2001-05-29 JO JO200183A patent/JO2361B1/en active
- 2001-06-13 NZ NZ522481A patent/NZ522481A/en not_active IP Right Cessation
- 2001-06-13 EA EA200300048A patent/EA005065B1/ru not_active IP Right Cessation
- 2001-06-13 CA CA002410232A patent/CA2410232C/en not_active Expired - Lifetime
- 2001-06-13 KR KR1020077026608A patent/KR100846370B1/ko active IP Right Grant
- 2001-06-13 PL PL358918A patent/PL209521B1/pl unknown
- 2001-06-13 JP JP2002504258A patent/JP4919575B2/ja not_active Expired - Lifetime
- 2001-06-13 AU AU2001263962A patent/AU2001263962B2/en not_active Expired
- 2001-06-13 CZ CZ2003114A patent/CZ295278B6/cs not_active IP Right Cessation
- 2001-06-13 ES ES01938263T patent/ES2241830T3/es not_active Expired - Lifetime
- 2001-06-13 MX MXPA02012845A patent/MXPA02012845A/es active IP Right Grant
- 2001-06-13 HU HU0300872A patent/HU229095B1/hu unknown
- 2001-06-13 AT AT01938263T patent/ATE294804T1/de active
- 2001-06-13 SK SK50-2003A patent/SK285699B6/sk not_active IP Right Cessation
- 2001-06-13 KR KR1020027014678A patent/KR100831940B1/ko active IP Right Grant
- 2001-06-13 US US10/312,301 patent/US20030114471A1/en not_active Abandoned
- 2001-06-13 EE EEP200200695A patent/EE04966B1/xx unknown
- 2001-06-13 UA UA20021210152A patent/UA73572C2/uk unknown
- 2001-06-13 WO PCT/EP2001/006747 patent/WO2001098302A1/en active IP Right Grant
- 2001-06-13 DE DE60110592T patent/DE60110592T2/de not_active Expired - Lifetime
- 2001-06-13 EP EP01938263A patent/EP1296984B1/en not_active Expired - Lifetime
- 2001-06-13 IL IL15356001A patent/IL153560A0/xx unknown
- 2001-06-13 CN CNB018113788A patent/CN1207296C/zh not_active Expired - Lifetime
- 2001-06-13 BR BRPI0111743-2 patent/BRPI0111743B8/pt not_active IP Right Cessation
- 2001-06-13 AU AU6396201A patent/AU6396201A/xx active Pending
- 2001-06-14 PA PA20018519501A patent/PA8519501A1/es unknown
- 2001-06-20 EG EG20010660A patent/EG24180A/xx active
- 2001-06-20 MY MYPI20012896A patent/MY127734A/en unknown
- 2001-06-21 AR ARP010102954A patent/AR030704A1/es not_active Application Discontinuation
- 2001-09-10 SA SA01220349A patent/SA01220349B1/ar unknown
2002
- 2002-10-25 IS IS6590A patent/IS2596B/is unknown
- 2002-11-25 BG BG107310A patent/BG65894B1/bg unknown
- 2002-12-12 HR HR20020989A patent/HRP20020989B1/xx not_active IP Right Cessation
- 2002-12-16 NO NO20026032A patent/NO324494B1/no not_active IP Right Cessation
- 2002-12-19 ZA ZA200210305A patent/ZA200210305B/en unknown
- 2002-12-19 IL IL153560A patent/IL153560A/en not_active IP Right Cessation
2004
- 2004-02-18 HK HK04101163A patent/HK1058363A1/xx not_active IP Right Cessation
2006
- 2006-09-20 AU AU2006220405A patent/AU2006220405B2/en not_active Expired
2007
- 2007-01-31 US US11/669,587 patent/US8329714B2/en active Active
- 2007-10-29 US US11/926,741 patent/US8318753B2/en active Active

Also Published As

Publication number	Publication date
AU2006220405B2 (en)	2009-05-21
CZ295278B6 (cs)	2005-06-15
US20030114471A1 (en)	2003-06-19
WO2001098302A1 (en)	2001-12-27
ATE294804T1 (de)	2005-05-15
DE60110592D1 (de)	2005-06-09
PA8519501A1 (es)	2002-08-29
AR030704A1 (es)	2003-09-03
PL358918A1 (en)	2004-08-23
AU6396201A (en)	2002-01-02
BG65894B1 (bg)	2010-04-30
US20080114009A1 (en)	2008-05-15
ZA200210305B (en)	2004-03-19
EE200200695A (et)	2004-06-15
JP4919575B2 (ja)	2012-04-18
IL153560A0 (en)	2003-07-06
ES2241830T3 (es)	2005-11-01
EG24180A (en)	2008-09-28
BR0111743A (pt)	2003-07-08
SA01220349B1 (ar)	2007-01-23
KR20070121847A (ko)	2007-12-27
CA2410232C (en)	2008-10-07
NO20026032L (no)	2002-12-16
JP2004501153A (ja)	2004-01-15
KR20030009463A (ko)	2003-01-29
EP1296984B1 (en)	2005-05-04
EA005065B1 (ru)	2004-10-28
KR100846370B1 (ko)	2008-07-15
NO324494B1 (no)	2007-10-29
HUP0300872A3 (en)	2004-11-29
KR100831940B1 (ko)	2008-05-23
BRPI0111743B1 (pt)	2019-03-26
AU2006220405A1 (en)	2006-10-12
CN1437601A (zh)	2003-08-20
HK1058363A1 (en)	2004-05-14
SK502003A3 (en)	2003-05-02
NZ522481A (en)	2004-09-24
PL209521B1 (pl)	2011-09-30
DE60110592T2 (de)	2006-01-19
IS2596B (is)	2010-03-15
SK285699B6 (sk)	2007-06-07
BG107310A (bg)	2003-07-31
CA2410232A1 (en)	2001-12-27
EA200300048A1 (ru)	2003-04-24
HUP0300872A2 (hu)	2003-07-28
NO20026032D0 (no)	2002-12-16
US8329714B2 (en)	2012-12-11
HRP20020989A2 (en)	2005-02-28
BRPI0111743B8 (pt)	2021-05-25
IL153560A (en)	2011-06-30
EP1296984A1 (en)	2003-04-02
EE04966B1 (et)	2008-02-15
AU2001263962B2 (en)	2006-07-20
CN1207296C (zh)	2005-06-22
IS6590A (is)	2002-10-25
HRP20020989B1 (en)	2011-05-31
JO2361B1 (en)	2006-12-12
MXPA02012845A (es)	2003-05-15
US8318753B2 (en)	2012-11-27
HU229095B1 (en)	2013-07-29
US20070259902A1 (en)	2007-11-08
CZ2003114A3 (cs)	2003-05-14
MY127734A (en)	2006-12-29

Publication	Publication Date	Title
ES2313991T3 (es)	2009-03-16	Derivados de 6-heterociclilmetil-quinolina y quinazolina que inhiben la farnesil transferasa.
JP4911866B2 (ja)	2012-04-04	ファルネシルトランスフェラーゼ阻害剤としてのファルネシルトランスフェラーゼを阻害するキノリンおよびキナゾリン誘導体
US8318753B2 (en)	2012-11-27	Farnesyl transferase inhibiting 1,2-annelated quinoline enantiomer
JP2020502065A (ja)	2020-01-23	８，９−ジヒドロイミダゾール［１，２−ａ］ピリミド［５，４−ｅ］ピリミジン−５（６Ｈ）−ケトン類化合物
AU2001263962A1 (en)	2002-03-21	Farnesyl transferase inhibiting 1,2-annelated quinoline enantiomer
CN113350347B (zh)	2023-07-04	吲唑类化合物的用途
JP4537710B2 (ja)	2010-09-08	ファルネシルトランスフェラーゼ阻害剤としての炭素連結トリアゾールで置換されている１，８−アネル化キノリン誘導体
WO2002042296A1 (en)	2002-05-30	Farnesyl transferase inhibiting benzoheterocyclic derivatives
JP4384505B2 (ja)	2009-12-16	ファルネシルトランスフェラーゼを阻害する炭素連結イミダゾールもしくはトリアゾール置換三環状キナゾリン誘導体