KR20060135035A - 유사분열 키네신 억제제 - Google Patents
유사분열 키네신 억제제 Download PDFInfo
- Publication number
- KR20060135035A KR20060135035A KR1020067021822A KR20067021822A KR20060135035A KR 20060135035 A KR20060135035 A KR 20060135035A KR 1020067021822 A KR1020067021822 A KR 1020067021822A KR 20067021822 A KR20067021822 A KR 20067021822A KR 20060135035 A KR20060135035 A KR 20060135035A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- alkyl
- group
- aryl
- heterocyclyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000011278 mitosis Effects 0.000 title description 2
- 229940124179 Kinesin inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
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- 238000000034 method Methods 0.000 claims abstract description 39
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- 201000010099 disease Diseases 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 230000002062 proliferating effect Effects 0.000 claims abstract description 12
- 230000001404 mediated effect Effects 0.000 claims abstract description 10
- -1 nitro, carboxy, hydroxy Chemical group 0.000 claims description 115
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 125000000623 heterocyclic group Chemical group 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229940002612 prodrug Drugs 0.000 claims description 15
- 239000000651 prodrug Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
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- 229910052717 sulfur Inorganic materials 0.000 claims description 8
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- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
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- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound 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 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 6
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 5
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 5
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 5
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 5
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
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- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
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- 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 claims description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 210000000481 breast Anatomy 0.000 claims description 4
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- PNNDGLXCMNOPHN-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound N1=C2CCCCN2C(=O)C(CC=2C=CC=CC=2)=C1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 PNNDGLXCMNOPHN-UHFFFAOYSA-N 0.000 claims description 4
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- 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 claims description 4
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 3
- 206010048832 Colon adenoma Diseases 0.000 claims description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 3
- 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 claims description 3
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- BWZYNWCMTYBERI-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-3-fluoro-4-methylbenzamide Chemical compound N1=C2CCCCN2C(=O)C(CC=2C=CC=CC=2)=C1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C(F)=C1 BWZYNWCMTYBERI-UHFFFAOYSA-N 0.000 claims description 3
- ZBJDITQFBYJTLK-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)propyl]-4-bromobenzamide Chemical compound N1=C2CCCCN2C(=O)C(CC=2C=CC=CC=2)=C1C(CC)N(CCCN)C(=O)C1=CC=C(Br)C=C1 ZBJDITQFBYJTLK-UHFFFAOYSA-N 0.000 claims description 3
- PNJJTYFWKNHNAA-UHFFFAOYSA-N n-[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-2-yl)-2-methylpropyl]-4-methyl-n-[3-(methylamino)propyl]benzamide Chemical compound C=1C=C(C)C=CC=1C(=O)N(CCCNC)C(C(C)C)C=1N=C2CCCCN2C(=O)C=1CC1=CC=CC=C1 PNJJTYFWKNHNAA-UHFFFAOYSA-N 0.000 claims description 3
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 208000029387 trophoblastic neoplasm Diseases 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 230000006444 vascular growth Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000010969 white metal Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56023504P | 2004-04-06 | 2004-04-06 | |
| US60/560,235 | 2004-04-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060135035A true KR20060135035A (ko) | 2006-12-28 |
Family
ID=34964986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067021822A Withdrawn KR20060135035A (ko) | 2004-04-06 | 2005-04-06 | 유사분열 키네신 억제제 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US20080249112A1 (https=) |
| EP (1) | EP1732926B1 (https=) |
| JP (1) | JP4895220B2 (https=) |
| KR (1) | KR20060135035A (https=) |
| CN (1) | CN1984912A (https=) |
| AT (1) | ATE419249T1 (https=) |
| AU (1) | AU2005233576A1 (https=) |
| BR (1) | BRPI0509653A (https=) |
| CA (1) | CA2561904A1 (https=) |
| DE (1) | DE602005012069D1 (https=) |
| ES (1) | ES2318478T3 (https=) |
| PL (1) | PL1732926T3 (https=) |
| PT (1) | PT1732926E (https=) |
| RU (1) | RU2006138864A (https=) |
| WO (1) | WO2005100357A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3947758B2 (ja) * | 2003-03-07 | 2007-07-25 | アストラゼネカ アクチボラグ | 新規縮合ヘテロサイクル及びその使用 |
| AR050920A1 (es) * | 2003-03-07 | 2006-12-06 | Astrazeneca Ab | Enantiomeros de heterociclos fusionados seleccionados y usos de los mismos |
| ATE419249T1 (de) * | 2004-04-06 | 2009-01-15 | Novartis Vaccines & Diagnostic | Inhibitoren von mitotischem kinesin |
| KR101170925B1 (ko) * | 2004-06-18 | 2012-08-07 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 암 치료용 키네신 방추 단백질 (ｋｓｐ) 억제제로서의ｎ-(1-(1-벤질-4-페닐-1ｈ-이미다졸-2-일)-2,2-디메틸프로필)벤자미드 유도체 및 관련 화합물 |
| RU2007106552A (ru) * | 2004-07-22 | 2008-08-27 | Астразенека Аб (Se) | Конденсированные пиримидоны, пригодные для лечения и предотвращения злокачественного новообразования |
| US20060041128A1 (en) * | 2004-08-18 | 2006-02-23 | Astrazeneca Ab | Selected fused heterocyclics and uses thereof |
| CN101027309B (zh) * | 2004-08-18 | 2010-10-27 | 阿斯利康(瑞典)有限公司 | 所选择的稠合嘧啶酮的对映体和在治疗和预防癌症中的用途 |
| AU2007323998B2 (en) * | 2006-11-13 | 2011-09-22 | Novartis Ag | Substituted pyrazole and triazole compounds as KSP inhibitors |
| AU2008205169B2 (en) * | 2007-01-05 | 2012-02-02 | Novartis Ag | Imidazole derivatives as kinesin spindle protein inhibitors (Eg-5) |
| WO2010042392A2 (en) * | 2008-10-06 | 2010-04-15 | Merck & Co., Inc. | Hiv integrase inhibitors |
| US10786578B2 (en) | 2014-08-05 | 2020-09-29 | Novartis Ag | CKIT antibody drug conjugates |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2157285B (en) | 1984-04-11 | 1987-10-28 | Erba Farmitalia | 1h, 7h-pyrazolo1, 5-a pyrimidine-7-one derivatives and process for their preparation |
| US20050107404A1 (en) | 2001-12-06 | 2005-05-19 | Fraley Mark E. | Mitotic kinesin inhibitors |
| CA2485148A1 (en) * | 2002-05-09 | 2003-11-20 | Cytokinetics, Inc. | Pyrimidinone compounds, compositions and methods |
| EP1513820A4 (en) | 2002-05-23 | 2006-09-13 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| AU2003256805A1 (en) * | 2002-07-23 | 2004-02-09 | Cytokinetics, Inc. | Compounds compositions and methods |
| WO2004064741A2 (en) * | 2003-01-17 | 2004-08-05 | Cytokinetics Inc. | Compounds, compositions, and methods |
| US7345046B2 (en) * | 2003-05-30 | 2008-03-18 | Chiron Corporation | Heteroaryl-fused pyrimidinyl compounds as anticancer agents |
| WO2004113335A2 (en) | 2003-06-20 | 2004-12-29 | Chiron Corporation | Pyridino[1,2-a]pyrimidin-4-one compounds as anticancer agents |
| ATE419249T1 (de) * | 2004-04-06 | 2009-01-15 | Novartis Vaccines & Diagnostic | Inhibitoren von mitotischem kinesin |
-
2005
- 2005-04-06 AT AT05732607T patent/ATE419249T1/de active
- 2005-04-06 KR KR1020067021822A patent/KR20060135035A/ko not_active Withdrawn
- 2005-04-06 PL PL05732607T patent/PL1732926T3/pl unknown
- 2005-04-06 AU AU2005233576A patent/AU2005233576A1/en not_active Abandoned
- 2005-04-06 WO PCT/US2005/011642 patent/WO2005100357A1/en not_active Ceased
- 2005-04-06 RU RU2006138864/04A patent/RU2006138864A/ru not_active Application Discontinuation
- 2005-04-06 PT PT05732607T patent/PT1732926E/pt unknown
- 2005-04-06 US US11/547,834 patent/US20080249112A1/en not_active Abandoned
- 2005-04-06 DE DE602005012069T patent/DE602005012069D1/de not_active Expired - Lifetime
- 2005-04-06 US US11/100,923 patent/US7504405B2/en not_active Expired - Fee Related
- 2005-04-06 ES ES05732607T patent/ES2318478T3/es not_active Expired - Lifetime
- 2005-04-06 BR BRPI0509653-7A patent/BRPI0509653A/pt not_active IP Right Cessation
- 2005-04-06 CN CNA2005800174322A patent/CN1984912A/zh active Pending
- 2005-04-06 EP EP05732607A patent/EP1732926B1/en not_active Expired - Lifetime
- 2005-04-06 CA CA002561904A patent/CA2561904A1/en not_active Abandoned
- 2005-04-06 JP JP2007507466A patent/JP4895220B2/ja not_active Expired - Fee Related
-
2009
- 2009-03-04 US US12/398,118 patent/US20090171082A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20050228002A1 (en) | 2005-10-13 |
| JP2007532554A (ja) | 2007-11-15 |
| RU2006138864A (ru) | 2008-05-20 |
| US7504405B2 (en) | 2009-03-17 |
| JP4895220B2 (ja) | 2012-03-14 |
| CN1984912A (zh) | 2007-06-20 |
| ATE419249T1 (de) | 2009-01-15 |
| US20090171082A1 (en) | 2009-07-02 |
| AU2005233576A1 (en) | 2005-10-27 |
| BRPI0509653A (pt) | 2007-10-09 |
| ES2318478T3 (es) | 2009-05-01 |
| EP1732926B1 (en) | 2008-12-31 |
| US20080249112A1 (en) | 2008-10-09 |
| PL1732926T3 (pl) | 2009-06-30 |
| WO2005100357A1 (en) | 2005-10-27 |
| DE602005012069D1 (de) | 2009-02-12 |
| CA2561904A1 (en) | 2005-10-27 |
| PT1732926E (pt) | 2009-04-03 |
| EP1732926A1 (en) | 2006-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20061020 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |