CA2564215A1 - Substituted quinoline derivatives as mitotic kinesin inhibitors - Google Patents
Substituted quinoline derivatives as mitotic kinesin inhibitors Download PDFInfo
- Publication number
- CA2564215A1 CA2564215A1 CA002564215A CA2564215A CA2564215A1 CA 2564215 A1 CA2564215 A1 CA 2564215A1 CA 002564215 A CA002564215 A CA 002564215A CA 2564215 A CA2564215 A CA 2564215A CA 2564215 A1 CA2564215 A1 CA 2564215A1
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- CA
- Canada
- Prior art keywords
- compound
- group
- substituted
- alkyl
- cycloalkyl
- 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.)
- Abandoned
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- 102000010638 Kinesin Human genes 0.000 title abstract description 9
- 108010063296 Kinesin Proteins 0.000 title abstract description 9
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title description 9
- 230000000394 mitotic effect Effects 0.000 title description 7
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 239000000203 mixture Substances 0.000 claims abstract description 71
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 229940002612 prodrug Drugs 0.000 claims abstract description 14
- 239000000651 prodrug Substances 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 13
- 239000003937 drug carrier Substances 0.000 claims abstract description 6
- -1 carboxyl ester Chemical group 0.000 claims description 126
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 206010028980 Neoplasm Diseases 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 12
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
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- 239000001301 oxygen Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002541 furyl group Chemical group 0.000 claims description 4
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- TVEXKRMIKGLDGZ-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloroquinolin-2-yl)-2-methylpropyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C=C(CC=2C=CC=CC=2)C=1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 TVEXKRMIKGLDGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
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- DQOAEPATSHONEH-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3-fluoro-4-methylbenzamide Chemical compound N=1C2=CC=CC=C2C=C(CC=2C=CC=CC=2)C=1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C(F)=C1 DQOAEPATSHONEH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 2
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 206010048832 Colon adenoma Diseases 0.000 claims description 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims description 2
- 208000034578 Multiple myelomas Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 210000000621 bronchi Anatomy 0.000 claims description 2
- 210000003679 cervix uteri Anatomy 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 210000003238 esophagus Anatomy 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
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- UYTKFWJKADWKBQ-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloroquinolin-2-yl)-2-methylpropyl]-3-fluoro-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C=C(CC=2C=CC=CC=2)C=1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C(F)=C1 UYTKFWJKADWKBQ-UHFFFAOYSA-N 0.000 claims description 2
- VUWDJNTXMFZAOD-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzylquinolin-2-yl)-2-methylpropyl]-3,4-dimethylbenzamide Chemical compound N=1C2=CC=CC=C2C=C(CC=2C=CC=CC=2)C=1C(C(C)C)N(CCCN)C(=O)C1=CC=C(C)C(C)=C1 VUWDJNTXMFZAOD-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
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- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
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- 229960000575 trastuzumab Drugs 0.000 claims 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 2
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- 239000005517 L01XE01 - Imatinib Substances 0.000 claims 2
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- 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 2
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- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
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- 235000010487 tragacanth Nutrition 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
- 230000037317 transdermal delivery Effects 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
- 208000029387 trophoblastic neoplasm Diseases 0.000 description 1
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- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Gastroenterology & Hepatology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57312004P | 2004-05-21 | 2004-05-21 | |
| US60/573,120 | 2004-05-21 | ||
| PCT/US2005/017961 WO2005113507A1 (en) | 2004-05-21 | 2005-05-19 | Substituted quinoline derivatives as mitotic kinesin inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2564215A1 true CA2564215A1 (en) | 2005-12-01 |
Family
ID=34970815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002564215A Abandoned CA2564215A1 (en) | 2004-05-21 | 2005-05-19 | Substituted quinoline derivatives as mitotic kinesin inhibitors |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7452996B2 (enExample) |
| EP (1) | EP1753723B1 (enExample) |
| JP (1) | JP2008502721A (enExample) |
| CN (1) | CN1956960A (enExample) |
| AT (1) | ATE404536T1 (enExample) |
| AU (1) | AU2005245492A1 (enExample) |
| BR (1) | BRPI0511433A (enExample) |
| CA (1) | CA2564215A1 (enExample) |
| DE (1) | DE602005008953D1 (enExample) |
| DK (1) | DK1753723T3 (enExample) |
| ES (1) | ES2311992T3 (enExample) |
| HR (1) | HRP20080493T3 (enExample) |
| MX (1) | MXPA06011958A (enExample) |
| PL (1) | PL1753723T3 (enExample) |
| PT (1) | PT1753723E (enExample) |
| RS (1) | RS50670B (enExample) |
| RU (1) | RU2385867C2 (enExample) |
| SI (1) | SI1753723T1 (enExample) |
| WO (1) | WO2005113507A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
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| BRPI0511433A (pt) * | 2004-05-21 | 2007-12-11 | Chiron Corp | derivados de quinolina substituìda como inibidores de cinesina mitótica |
| AU2005273705B8 (en) | 2004-08-18 | 2010-01-28 | Astrazeneca Ab | Enantiomers of selected fused pyrimidones and uses in the treatment and prevention of cancer |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP3095456A1 (en) * | 2005-11-04 | 2016-11-23 | Glaxosmithkline LLC | Methods for administering hypoglycemic agents |
| BRPI0719883A2 (pt) | 2006-10-09 | 2015-05-05 | Takeda Pharmaceutical | Inibidores de quinase |
| CA2668661A1 (en) * | 2006-11-13 | 2008-05-29 | Novartis Ag | Substituted pyrazole and triazole compounds as ksp inhibitors |
| MX2009007260A (es) * | 2007-01-05 | 2009-07-10 | Novartis Ag | Derivados de imidazol como inhibidores de proteina de huso de cinesina (eg-5). |
| FR2940289B1 (fr) * | 2008-12-23 | 2014-09-12 | Biopharmed | Derives de la classe des hydroxyquinoleines aminees pour le traitement du cancer du pancreas |
| US8748626B2 (en) * | 2010-04-15 | 2014-06-10 | Novartis Ag | Oxazole and thiazole compounds as KSP inhibitors |
| AU2011239977B2 (en) * | 2010-04-15 | 2014-11-27 | Novartis Ag | Triazole compounds as KSP inhibitors |
| EP3444363B1 (en) | 2011-06-03 | 2020-11-25 | Eisai R&D Management Co., Ltd. | Biomarkers for prediciting and assessing responsiveness of thyroid and kidney cancer subjects to lenvatinib compounds |
| RU2486175C2 (ru) * | 2011-09-12 | 2013-06-27 | Закрытое Акционерное Общество "Фарм-Синтез" | Производные хинолина, в частности 5,6,7-замещенные 1-(2-хлорхинолин-3-ил)-4-диметиламино-2-(нафталин-1-ил)-1-фенилбутан-2-олы, способ получения и применение соединений |
| US9458161B1 (en) | 2011-11-03 | 2016-10-04 | Vanderblit University | TSPO ligands for cancer imaging and treatment |
| NZ631362A (en) * | 2012-08-13 | 2016-09-30 | Array Biopharma Inc | Arry-520 for use in treating cancer in a patient with low aag |
| KR102329681B1 (ko) | 2014-08-28 | 2021-11-23 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 고순도의 퀴놀린 유도체 및 이를 제조하는 방법 |
| KR20250024102A (ko) | 2015-02-25 | 2025-02-18 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 퀴놀린 유도체의 고미 억제 방법 |
| AU2015384801B2 (en) | 2015-03-04 | 2022-01-06 | Eisai R&D Management Co., Ltd. | Combination of a PD-1 antagonist and a VEGFR/FGFR/RET tyrosine kinase inhibitor for treating cancer |
| ES2886107T3 (es) | 2015-06-16 | 2021-12-16 | Prism Biolab Co Ltd | Antineoplásico |
| RU2728932C2 (ru) * | 2015-08-19 | 2020-08-03 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Терапевтическое средство для лечения рака желчевыводящих путей |
| SG11201801083UA (en) | 2015-08-20 | 2018-03-28 | Eisai R&D Man Co Ltd | Tumor therapeutic agent |
| US12303505B2 (en) | 2017-02-08 | 2025-05-20 | Eisai R&D Management Co., Ltd. | Tumor-treating pharmaceutical composition |
| US20200197384A1 (en) | 2017-05-16 | 2020-06-25 | Eisai R&D Management Co., Ltd. | Treatment of hepatocellular carcinoma |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6172087B1 (en) * | 1998-06-03 | 2001-01-09 | Gpi Nil Holding, Inc. | N-oxide of heterocyclic ester, amide, thioester, or ketone hair growth compositions and uses |
| EP1165519A1 (en) | 1999-04-02 | 2002-01-02 | Neurogen Corporation | Aryl and heteroaryl fused aminoalkyl-imidazole derivatives and their use as antidiabetics |
| DE60028227T2 (de) | 1999-10-27 | 2007-03-29 | Cytokinetics, Inc., South San Francisco | Chinazolinone benutzende verfahren und zusammenstellungen |
| US6545004B1 (en) * | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
| AU2001296799A1 (en) | 2000-10-06 | 2002-04-15 | Neurogen Corporation | Benzimidazole and indole derivatives as crf receptor modulators |
| KR100883184B1 (ko) | 2000-12-11 | 2009-02-12 | 암젠 인코포레이션 | Ｃｘｃｒ3 길항제 |
| EP1351671A1 (en) | 2001-01-19 | 2003-10-15 | Cytokinetics, Inc. | Triphenylmethane kinesin inhibitors |
| EP1360180A1 (en) | 2001-01-19 | 2003-11-12 | Cytokinetics, Inc. | Phenothiazine kinesin inhibitors |
| WO2003039460A2 (en) | 2001-11-07 | 2003-05-15 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| US6753428B2 (en) | 2001-11-20 | 2004-06-22 | Cytokinetics, Inc. | Process for the racemization of chiral quinazolinones |
| WO2003049527A2 (en) | 2001-12-06 | 2003-06-19 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| US7244723B2 (en) | 2001-12-06 | 2007-07-17 | Merck & Co., Inc. | Substituted furopyrimidinones as a mitotic kinesin inhibitors |
| DE60222302T2 (de) | 2001-12-06 | 2008-05-29 | Merck & Co., Inc. | Inhibitoren von mitotischem kinesin |
| EP1481077B1 (en) | 2001-12-06 | 2009-11-04 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| EP1551812B1 (en) | 2001-12-06 | 2009-03-04 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| WO2003059289A2 (en) | 2002-01-10 | 2003-07-24 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
| CA2475879A1 (en) | 2002-02-15 | 2003-08-28 | Cytokinetics, Inc. | Synthesis of quinazolinones |
| AU2003249597B2 (en) | 2002-03-08 | 2007-06-28 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
| PL211300B1 (pl) | 2002-04-17 | 2012-05-31 | Cytokinetics Inc | Związek i kompozycja zawierająca ten związek |
| WO2003094839A2 (en) | 2002-05-09 | 2003-11-20 | Cytokinetics, Inc. | Pyrimidinone compounds, compositions and methods |
| AU2003270015A1 (en) | 2002-05-09 | 2003-12-02 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| EP1513820A4 (en) | 2002-05-23 | 2006-09-13 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| EP1509507A4 (en) | 2002-05-23 | 2006-09-13 | Merck & Co Inc | INHIBITORS OF MITOTIC KINESINE |
| PL374190A1 (en) | 2002-06-14 | 2005-10-03 | Merck & Co, Inc. | Mitotic kinesin inhibitors |
| AU2003236527A1 (en) | 2002-06-14 | 2003-12-31 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| EP1515949B1 (en) | 2002-06-14 | 2007-03-14 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP2005537257A (ja) | 2002-07-08 | 2005-12-08 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン結合部位 |
| EP1539727B1 (en) | 2002-07-17 | 2009-02-18 | Cytokinetics, Inc. | Compounds, compositions, and methods for treating cellular proliferative diseases |
| EP1537089A4 (en) | 2002-07-23 | 2008-04-16 | Cytokinetics Inc | CONNECTIONS, COMPOSITIONS AND PROCEDURES |
| EP1539180A4 (en) | 2002-08-21 | 2006-08-30 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| JP2005539062A (ja) | 2002-09-13 | 2005-12-22 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
| BRPI0511433A (pt) * | 2004-05-21 | 2007-12-11 | Chiron Corp | derivados de quinolina substituìda como inibidores de cinesina mitótica |
-
2005
- 2005-05-19 BR BRPI0511433-0A patent/BRPI0511433A/pt not_active IP Right Cessation
- 2005-05-19 RS RSP-2008/0534A patent/RS50670B/sr unknown
- 2005-05-19 PT PT05752901T patent/PT1753723E/pt unknown
- 2005-05-19 PL PL05752901T patent/PL1753723T3/pl unknown
- 2005-05-19 ES ES05752901T patent/ES2311992T3/es not_active Expired - Lifetime
- 2005-05-19 US US11/133,509 patent/US7452996B2/en not_active Expired - Fee Related
- 2005-05-19 JP JP2007527522A patent/JP2008502721A/ja active Pending
- 2005-05-19 SI SI200530384T patent/SI1753723T1/sl unknown
- 2005-05-19 CN CNA2005800164405A patent/CN1956960A/zh active Pending
- 2005-05-19 WO PCT/US2005/017961 patent/WO2005113507A1/en not_active Ceased
- 2005-05-19 DK DK05752901T patent/DK1753723T3/da active
- 2005-05-19 MX MXPA06011958A patent/MXPA06011958A/es active IP Right Grant
- 2005-05-19 HR HR20080493T patent/HRP20080493T3/xx unknown
- 2005-05-19 DE DE602005008953T patent/DE602005008953D1/de not_active Expired - Lifetime
- 2005-05-19 AU AU2005245492A patent/AU2005245492A1/en not_active Abandoned
- 2005-05-19 EP EP05752901A patent/EP1753723B1/en not_active Expired - Lifetime
- 2005-05-19 AT AT05752901T patent/ATE404536T1/de not_active IP Right Cessation
- 2005-05-19 RU RU2006145336/04A patent/RU2385867C2/ru not_active IP Right Cessation
- 2005-05-19 CA CA002564215A patent/CA2564215A1/en not_active Abandoned
-
2008
- 2008-09-30 US US12/242,360 patent/US20090028858A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1956960A (zh) | 2007-05-02 |
| PL1753723T3 (pl) | 2009-01-30 |
| WO2005113507A1 (en) | 2005-12-01 |
| JP2008502721A (ja) | 2008-01-31 |
| ATE404536T1 (de) | 2008-08-15 |
| US20090028858A1 (en) | 2009-01-29 |
| BRPI0511433A (pt) | 2007-12-11 |
| EP1753723B1 (en) | 2008-08-13 |
| DK1753723T3 (da) | 2008-10-20 |
| RS50670B (sr) | 2010-06-30 |
| AU2005245492A1 (en) | 2005-12-01 |
| US20050261337A1 (en) | 2005-11-24 |
| RU2385867C2 (ru) | 2010-04-10 |
| ES2311992T3 (es) | 2009-02-16 |
| SI1753723T1 (sl) | 2009-04-30 |
| PT1753723E (pt) | 2008-11-19 |
| EP1753723A1 (en) | 2007-02-21 |
| MXPA06011958A (es) | 2006-12-15 |
| DE602005008953D1 (de) | 2008-09-25 |
| HRP20080493T3 (hr) | 2009-02-28 |
| US7452996B2 (en) | 2008-11-18 |
| RU2006145336A (ru) | 2008-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |