IL138590A - Antitumor factors - Google Patents

Antitumor factors

Info

Publication number: IL138590A
Authority: IL; Israel
Prior art keywords: alkyl; alkoxy; methyl; hydrogen; amino
Prior art date: 1998-03-20

Application number

IL13859099A

Other languages

English (en)

Hebrew (he)

Other versions

IL138590A0 (en

Original Assignee

Astrazeneca Ab

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.)

1998-03-20

Filing date

1999-03-16

Publication date

2004-08-31

1999-03-16 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2001-10-31 Publication of IL138590A0 publication Critical patent/IL138590A0/xx

2004-08-31 Publication of IL138590A publication Critical patent/IL138590A/en

Links

230000000259 anti-tumor effect Effects 0.000 title claims abstract description 49
125000000217 alkyl group Chemical group 0.000 claims abstract description 183
-1 benzensulphonyloxy Chemical group 0.000 claims abstract description 154
125000003545 alkoxy group Chemical group 0.000 claims abstract description 104
239000001257 hydrogen Substances 0.000 claims abstract description 73
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
239000003795 chemical substances by application Substances 0.000 claims abstract description 42
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 41
150000002431 hydrogen Chemical group 0.000 claims abstract description 36
150000003839 salts Chemical class 0.000 claims abstract description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
125000005843 halogen group Chemical group 0.000 claims abstract description 15
125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
125000005277 alkyl imino group Chemical group 0.000 claims abstract description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 5
125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 4
125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
125000005236 alkanoylamino group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 75
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 38
238000000034 method Methods 0.000 claims description 27
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 20
230000009467 reduction Effects 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
239000007858 starting material Substances 0.000 claims description 18
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
241001465754 Metazoa Species 0.000 claims description 13
125000001153 fluoro group Chemical group F* 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
125000004154 1,4-benzoquinonyl group Chemical group C1(C(=CC(C=C1)=O)*)=O 0.000 claims description 5
230000001028 anti-proliverative effect Effects 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000002346 iodo group Chemical group I* 0.000 claims description 3
GFWZPTGIVKRQNM-UHFFFAOYSA-N n,3-dimethylbutanamide Chemical compound CNC(=O)CC(C)C GFWZPTGIVKRQNM-UHFFFAOYSA-N 0.000 claims description 3
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
OLLZXQIFCRIRMH-UHFFFAOYSA-N n-methylbutanamide Chemical compound CCCC(=O)NC OLLZXQIFCRIRMH-UHFFFAOYSA-N 0.000 claims 1
125000003302 alkenyloxy group Chemical group 0.000 abstract description 3
125000004414 alkyl thio group Chemical group 0.000 abstract description 2
229910052757 nitrogen Inorganic materials 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 88
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 35
101150041968 CDC13 gene Proteins 0.000 description 32
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
238000012360 testing method Methods 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
206010028980 Neoplasm Diseases 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
210000004027 cell Anatomy 0.000 description 22
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
238000004440 column chromatography Methods 0.000 description 20
239000003480 eluent Substances 0.000 description 20
239000000377 silicon dioxide Substances 0.000 description 20
238000011282 treatment Methods 0.000 description 20
239000012074 organic phase Substances 0.000 description 18
239000000463 material Substances 0.000 description 16
229940127089 cytotoxic agent Drugs 0.000 description 15
239000002254 cytotoxic agent Substances 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
206010021143 Hypoxia Diseases 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 12
230000001146 hypoxic effect Effects 0.000 description 12
229940002612 prodrug Drugs 0.000 description 12
239000000651 prodrug Substances 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 12
239000001963 growth medium Substances 0.000 description 11
239000011369 resultant mixture Substances 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
239000003208 petroleum Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
231100000599 cytotoxic agent Toxicity 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
241001529936 Murinae Species 0.000 description 7
230000001472 cytotoxic effect Effects 0.000 description 7
125000004356 hydroxy functional group Chemical group O* 0.000 description 7
238000001819 mass spectrum Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
108020004414 DNA Proteins 0.000 description 6
102000053602 DNA Human genes 0.000 description 6
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
238000013459 approach Methods 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
210000000481 breast Anatomy 0.000 description 6
231100000433 cytotoxic Toxicity 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
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BVYCLBMEDGNBRV-UHFFFAOYSA-N 4-n,4-n-bis(2-chloroethyl)-1-n-methylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.CNC1=CC=C(N(CCCl)CCCl)C=C1 BVYCLBMEDGNBRV-UHFFFAOYSA-N 0.000 description 5
239000000443 aerosol Substances 0.000 description 5
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
239000000499 gel Substances 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
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210000001519 tissue Anatomy 0.000 description 5
239000004338 Dichlorodifluoromethane Substances 0.000 description 4
241000282414 Homo sapiens Species 0.000 description 4
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 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000004147 Sorbitan trioleate Substances 0.000 description 4
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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150000008044 alkali metal hydroxides Chemical class 0.000 description 3
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239000008346 aqueous phase Substances 0.000 description 3
125000003435 aroyl group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
229960003433 thalidomide Drugs 0.000 description 1
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229940044693 topoisomerase inhibitor Drugs 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
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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
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125000001425 triazolyl group Chemical group 0.000 description 1
VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Saccharide Compounds (AREA)
Hydrogenated Pyridines (AREA)

IL13859099A 1998-03-20 1999-03-16 Antitumor factors IL138590A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9805868.8A GB9805868D0 (en)	1998-03-20	1998-03-20	Anti-tumour agents
PCT/GB1999/000786 WO1999048860A1 (fr)	1998-03-20	1999-03-16	Agents antitumoraux

Publications (2)

Publication Number	Publication Date
IL138590A0 IL138590A0 (en)	2001-10-31
IL138590A true IL138590A (en)	2004-08-31

Family

ID=10828860

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13859099A IL138590A (en)	1998-03-20	1999-03-16	Antitumor factors

Country Status (19)

Country	Link
US (1)	US6472435B1 (fr)
EP (1)	EP1064257B1 (fr)
JP (1)	JP2002507592A (fr)
KR (1)	KR20010042056A (fr)
CN (1)	CN1178900C (fr)
AT (1)	ATE231836T1 (fr)
AU (1)	AU746715B2 (fr)
BR (1)	BR9908934A (fr)
CA (1)	CA2319335A1 (fr)
DE (1)	DE69905143T2 (fr)
DK (1)	DK1064257T3 (fr)
ES (1)	ES2192036T3 (fr)
GB (1)	GB9805868D0 (fr)
IL (1)	IL138590A (fr)
NO (1)	NO20004663L (fr)
NZ (1)	NZ506011A (fr)
PT (1)	PT1064257E (fr)
WO (1)	WO1999048860A1 (fr)
ZA (1)	ZA200004386B (fr)

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GB9805866D0 (en)	1998-03-20	1998-05-13	Zeneca Ltd	Anti-tumour agents
US6413533B1 (en) *	1998-05-07	2002-07-02	The University Of Tennessee Research Corporation	Method for chemoprevention of prostate cancer
US20060099712A1 (en) *	2004-11-08	2006-05-11	Eastman Kodak Company	Correlation of anti-cancer activity of dyes with redox potentials
AU2006222941C1 (en) *	2005-03-11	2011-06-16	Medical Instill Technologies, Inc.	Sterile de-molding apparatus and method
US20110039943A1 (en) *	2005-03-14	2011-02-17	Robert Alonso	Methods for treating skin disorders with topical nitrogen mustard compositions
US8501818B2 (en) *	2005-03-14	2013-08-06	Ceptaris Therapeutics, Inc.	Stabilized compositions of alkylating agents and methods of using same
US7872050B2 (en) *	2005-03-14	2011-01-18	Yaupon Therapeutics Inc.	Stabilized compositions of volatile alkylating agents and methods of using thereof
US20110104250A1 (en) *	2007-09-07	2011-05-05	Mccarley Robin L	Redox-gated Liposomes
HUE043767T2 (hu)	2008-03-27	2019-09-30	Helsinn Healthcare Sa	Alkilezõszerek stabilizált készítményei és alkalmazási eljárásaik
KR101006166B1 (ko) *	2008-12-10	2011-01-07	건국대학교 산학협력단	지하철 역 선로에 설치되는 자기성 분진 수거 장치 및 그 방법
EP2718255B1 (fr)	2011-05-26	2019-02-13	Indiana University Research and Technology Corporation	Composés quinones pour traitement de maladies à médiation par ape1
US20140128398A1 (en)	2011-06-03	2014-05-08	Indiana University Research And Technology Corporation	Compounds, compositions and methods for treating oxidative dna damage disorders
US10730903B2 (en)	2016-09-19	2020-08-04	Memorial Sloan-Kettering Cancer Center	Adenosine analogs as methyltransferase inhibitors for treating cancer

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Publication number	Priority date	Publication date	Assignee	Title
DE2862107D1 (en)	1977-12-02	1982-11-18	Takeda Chemical Industries Ltd	Glucosamine-peptide derivatives and their pharmaceutical compositions
JPS58177934A (ja)	1982-04-13	1983-10-18	Takeda Chem Ind Ltd	ベンゾキノン誘導体
NZ240785A (en)	1991-11-28	1995-08-28	Cancer Res Campaign Tech	Substituted nitro aniline derivatives and medicaments
GB9805866D0 (en)	1998-03-20	1998-05-13	Zeneca Ltd	Anti-tumour agents

1998
- 1998-03-20 GB GBGB9805868.8A patent/GB9805868D0/en not_active Ceased
1999
- 1999-03-16 JP JP2000537845A patent/JP2002507592A/ja active Pending
- 1999-03-16 US US09/646,464 patent/US6472435B1/en not_active Expired - Fee Related
- 1999-03-16 CA CA002319335A patent/CA2319335A1/fr not_active Abandoned
- 1999-03-16 EP EP99909098A patent/EP1064257B1/fr not_active Expired - Lifetime
- 1999-03-16 NZ NZ506011A patent/NZ506011A/xx unknown
- 1999-03-16 CN CNB998040908A patent/CN1178900C/zh not_active Expired - Fee Related
- 1999-03-16 PT PT99909098T patent/PT1064257E/pt unknown
- 1999-03-16 KR KR1020007010400A patent/KR20010042056A/ko not_active Ceased
- 1999-03-16 WO PCT/GB1999/000786 patent/WO1999048860A1/fr not_active Ceased
- 1999-03-16 DE DE69905143T patent/DE69905143T2/de not_active Expired - Fee Related
- 1999-03-16 DK DK99909098T patent/DK1064257T3/da active
- 1999-03-16 BR BR9908934-3A patent/BR9908934A/pt not_active IP Right Cessation
- 1999-03-16 ES ES99909098T patent/ES2192036T3/es not_active Expired - Lifetime
- 1999-03-16 IL IL13859099A patent/IL138590A/en not_active IP Right Cessation
- 1999-03-16 AT AT99909098T patent/ATE231836T1/de not_active IP Right Cessation
- 1999-03-16 AU AU28467/99A patent/AU746715B2/en not_active Ceased
2000
- 2000-08-24 ZA ZA200004386A patent/ZA200004386B/en unknown
- 2000-09-19 NO NO20004663A patent/NO20004663L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE69905143T2 (de)	2003-11-20
EP1064257A1 (fr)	2001-01-03
NO20004663D0 (no)	2000-09-19
AU2846799A (en)	1999-10-18
ES2192036T3 (es)	2003-09-16
DK1064257T3 (da)	2003-05-26
JP2002507592A (ja)	2002-03-12
US6472435B1 (en)	2002-10-29
WO1999048860A1 (fr)	1999-09-30
NO20004663L (no)	2000-11-13
CA2319335A1 (fr)	1999-09-30
ATE231836T1 (de)	2003-02-15
PT1064257E (pt)	2003-06-30
NZ506011A (en)	2002-10-25
CN1293656A (zh)	2001-05-02
DE69905143D1 (de)	2003-03-06
IL138590A0 (en)	2001-10-31
ZA200004386B (en)	2002-01-30
EP1064257B1 (fr)	2003-01-29
BR9908934A (pt)	2005-10-25
AU746715B2 (en)	2002-05-02
CN1178900C (zh)	2004-12-08
KR20010042056A (ko)	2001-05-25
GB9805868D0 (en)	1998-05-13

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Legal Events

Date	Code	Title
2005-01-24	FF	Patent granted
2005-02-20	KB	Patent renewed
2005-05-17	KB	Patent renewed
2010-05-17	MM9K	Patent not in force due to non-payment of renewal fees