AU2010261399B2 - Bicyclic and tricyclic compounds as KAT II inhibitors - Google Patents
Bicyclic and tricyclic compounds as KAT II inhibitors Download PDFInfo
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- AU2010261399B2 AU2010261399B2 AU2010261399A AU2010261399A AU2010261399B2 AU 2010261399 B2 AU2010261399 B2 AU 2010261399B2 AU 2010261399 A AU2010261399 A AU 2010261399A AU 2010261399 A AU2010261399 A AU 2010261399A AU 2010261399 B2 AU2010261399 B2 AU 2010261399B2
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- Australia
- Prior art keywords
- amino
- hydroxy
- dihydroquinolin
- rac
- formula
- Prior art date
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- 125000001424 substituent group Chemical group 0.000 claims description 106
- 238000000034 method Methods 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 125000003118 aryl group Chemical group 0.000 claims description 85
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- 150000003839 salts Chemical class 0.000 claims description 73
- 125000003545 alkoxy group Chemical group 0.000 claims description 70
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 35
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 24
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
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- A—HUMAN NECESSITIES
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- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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| EP2646417A1 (en) * | 2010-12-01 | 2013-10-09 | Pfizer Inc | Kat ii inhibitors |
| WO2013005425A1 (ja) * | 2011-07-07 | 2013-01-10 | イハラケミカル工業株式会社 | ニトロベンゼン化合物の製造方法 |
| CN104364253A (zh) * | 2012-06-15 | 2015-02-18 | 辉瑞公司 | 作为kat ii抑制剂的三环化合物 |
| EP3610890A1 (en) | 2012-11-14 | 2020-02-19 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| DK2746250T3 (en) * | 2012-12-21 | 2018-01-02 | Abx Advanced Biochemical Compounds Gmbh | Intermediates and Processes for Preparation of 18F-Labeled Amino Acids |
| JPWO2014174745A1 (ja) * | 2013-04-26 | 2017-02-23 | 国立大学法人京都大学 | Eg5阻害剤 |
| WO2015163339A1 (ja) | 2014-04-23 | 2015-10-29 | 田辺三菱製薬株式会社 | 新規二環性または三環性複素環化合物 |
| CN104592333B (zh) * | 2014-07-23 | 2017-06-27 | 江西科技师范大学 | 一种合成5‑羧基‑2’‑脱氧胞苷的方法 |
| EP3372601B1 (en) | 2015-10-22 | 2022-09-21 | Mitsubishi Tanabe Pharma Corporation | Novel bicyclic heterocyclic compound |
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Non-Patent Citations (2)
| Title |
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| DAVIS, A. L. et al., 'Synthesis and Microbiological Properties of some Substituted Derivatives of 3-Amino-3,4-dihydrocarbostyril', Journal of Medicinal Chemistry, 1970, Vol. 13, No. 3, pages 549-550 * |
| MCCORD, T. J. et al., Journal of Heterocyclic Chemistry, 1981, Vol. 18, No. 5, pages 1035-1039 * |
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