USRE44638E1 - Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta - Google Patents
Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta Download PDFInfo
- Publication number
- USRE44638E1 USRE44638E1 US13/730,256 US200513730256A USRE44638E US RE44638 E1 USRE44638 E1 US RE44638E1 US 200513730256 A US200513730256 A US 200513730256A US RE44638 E USRE44638 E US RE44638E
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- United States
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- compound
- phenyl
- quinazolin
- ylamino
- purin
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
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Abstract
Description
File Name | Date of Creation | Size (bytes) |
616082000800seqlist.txt | Dec. 14, 2007 | 27,947 bytes |
R2 is hydrogen, methyl, chloro, or fluoro; R3 is hydrogen or fluoro; R6 is NH2, hydrogen, or fluoro; R7 is hydrogen or R5 and R7 are taken together to form
R8 is methyl, trifluoromethyl, chloro, or fluoro; R4 is hydrogen, fluoro, chloro, OH, OCH3, OCH2C═CH, O(CH2)2N (CH3)2, C(═O)CH3, C═CH, CN, C(═O)NH2, OCH2C (═O)NH2, O(CH2)2OCH3, O(CH2)2N(CH3)2,
and R5 is methyl, ethyl, propyl, phenyl, CH2OH, CH2OCH2C6H5, CH2CF3, CH2OC(CH3)3, CH2C═CH, (CH2)3N(C2H5)2, (CH2)3NH2, (CH2)4NH2, (CH2)3NHC (—O)OCH2C6H5, or (CH2)4NHC(—O)OCH2C6H5; Rc is hydrogen, methyl, fluoro, or bromo; and n is 0 or 1.
5′ Primer | (SEQ ID NO: 3) |
5′-GATCGAATTCGGCGCCACCATGGACTACAAGGACGACGATGACAAGT |
GCTTCAGTTTCATAATGCCTCC-3′ |
3′ Primer | (SEQ ID NO: 4) |
5′-GATCGCGGCCGCTTAAGATCTGTAGTCTTTCCGAACTGTGTG-3′ |
The 5′ primer was built to contain a FLAG® tag in frame with the p110β sequence. After amplification, the FLAG®-p110β sequence was subcloned using standard recombinant techniques into the EcoR1-Not1 sites of pFastbac HTa (Life Technologies), such that the clone was in frame with the His tag of the vector.
5′ Primer | (SEQ ID NO: 5) |
5′-AGAATGCGGCCGCATGGAGCTGGAGAACTATAAACAGCCC-3′ |
3′ Primer | (SEQ ID NO: 6) |
5′-CGCGGATCCTTAGGCTGAATGTTTCTCTCCTTGTTTG-3′ |
A FLAG® tag was subsequently attached to the 5′ end of the p110γ sequence and was cloned in the BamH1-Spe1 sites of pFastbac HTb (Life Technologies) using standard recombinant DNA techniques, with the FLAG®-110γ sequence in-frame with the His tag of the vector.
TABLE 1 | ||||||
Human | ||||||
Delta | Alpha- | Beta- | Gamma- | PMN | Human B | |
IC50 | Delta | Delta | Delta | Elastase | Lymphocyte | |
(nM) | Ratio | Ratio | Ratio | EC50 (nM) | EC50 (nM) | |
Compound | 12 | 662 | 78 | 67 | 382 | 1.6 |
117 | ||||||
Compound | 16 | 608 | 74 | 66 | 84 | 4.6 |
98 | ||||||
Compound | 9 | 248 | 49 | 21 | 119 | 6.1 |
107 | ||||||
Compound | 45 | 250 | 72 | 38 | 298 | 30.7 |
174 | ||||||
Compound | 26 | 721 | 94 | 62 | 584 | |
93 | ||||||
Claims (2)
Priority Applications (1)
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US13/730,256 USRE44638E1 (en) | 2004-05-13 | 2005-05-12 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
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US57078404P | 2004-05-13 | 2004-05-13 | |
PCT/US2005/016778 WO2005113556A1 (en) | 2004-05-13 | 2005-05-12 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US11/596,092 US7932260B2 (en) | 2004-05-13 | 2005-05-12 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US13/730,256 USRE44638E1 (en) | 2004-05-13 | 2005-05-12 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
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US13/163,597 Abandoned US20120015964A1 (en) | 2004-05-13 | 2011-06-17 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US13/728,807 Active US8586597B2 (en) | 2004-05-13 | 2012-12-27 | 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
US13/730,276 Active 2025-07-21 USRE44599E1 (en) | 2004-05-13 | 2012-12-28 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US13/765,610 Active US8779131B2 (en) | 2004-05-13 | 2013-02-12 | 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)-ethyl]-3H-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
US14/049,163 Active US8980901B2 (en) | 2004-05-13 | 2013-10-08 | 5-fluoro-3-phenyl-2[1-(9H-purin-6-ylamino)propyl]-3H-quinazolin-4-one and 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as inhibitors of human phosphatidylinositol 3-kinase delta |
US14/049,154 Active US8993583B2 (en) | 2004-05-13 | 2013-10-08 | 5-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)propyl]-3H-quinazolin-4-one and 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as inhibitors of human phosphatidylinositol 3-kinase delta |
US14/284,331 Active US9149477B2 (en) | 2004-05-13 | 2014-05-21 | 5-fluoro-3-phenyl-2-[1-(9h-purin-6-ylamino)propyl]-3h-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
US14/826,096 Active US10336756B2 (en) | 2004-05-13 | 2015-08-13 | (S)-2-(1-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one precursor of a quinazolinone as inhibitor of human phosphatidylinositol 3-kinase delta |
US16/418,558 Active US10906907B2 (en) | 2004-05-13 | 2019-05-21 | Tert-butyl (s)-(1-(5-fluoro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl)carbamate precursor of a quinazolinone inhibitor of human phosphatidylinositol 3-kinase delta and a process for preparing thereof |
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US11/596,092 Ceased US7932260B2 (en) | 2004-05-13 | 2005-05-12 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US12/732,124 Abandoned US20100256167A1 (en) | 2004-05-13 | 2010-03-25 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US12/732,128 Active 2025-07-21 US8207153B2 (en) | 2004-05-13 | 2010-03-25 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US13/163,597 Abandoned US20120015964A1 (en) | 2004-05-13 | 2011-06-17 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US13/728,807 Active US8586597B2 (en) | 2004-05-13 | 2012-12-27 | 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
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US13/765,610 Active US8779131B2 (en) | 2004-05-13 | 2013-02-12 | 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)-ethyl]-3H-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
US14/049,163 Active US8980901B2 (en) | 2004-05-13 | 2013-10-08 | 5-fluoro-3-phenyl-2[1-(9H-purin-6-ylamino)propyl]-3H-quinazolin-4-one and 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as inhibitors of human phosphatidylinositol 3-kinase delta |
US14/049,154 Active US8993583B2 (en) | 2004-05-13 | 2013-10-08 | 5-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)propyl]-3H-quinazolin-4-one and 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as inhibitors of human phosphatidylinositol 3-kinase delta |
US14/284,331 Active US9149477B2 (en) | 2004-05-13 | 2014-05-21 | 5-fluoro-3-phenyl-2-[1-(9h-purin-6-ylamino)propyl]-3h-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
US14/826,096 Active US10336756B2 (en) | 2004-05-13 | 2015-08-13 | (S)-2-(1-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one precursor of a quinazolinone as inhibitor of human phosphatidylinositol 3-kinase delta |
US16/418,558 Active US10906907B2 (en) | 2004-05-13 | 2019-05-21 | Tert-butyl (s)-(1-(5-fluoro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl)carbamate precursor of a quinazolinone inhibitor of human phosphatidylinositol 3-kinase delta and a process for preparing thereof |
US17/103,631 Abandoned US20210332047A1 (en) | 2004-05-13 | 2020-11-24 | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
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EP (4) | EP1761540B1 (en) |
JP (1) | JP2007537291A (en) |
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