GB812366A - Improvements in and relating to derivatives of pyrimidine and the preparation thereof - Google Patents

Improvements in and relating to derivatives of pyrimidine and the preparation thereof

Info

Publication number
GB812366A
GB812366A GB2382355A GB2382355A GB812366A GB 812366 A GB812366 A GB 812366A GB 2382355 A GB2382355 A GB 2382355A GB 2382355 A GB2382355 A GB 2382355A GB 812366 A GB812366 A GB 812366A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
pyrimidine
amino
mercapto
diethoxyethylpyrimidine
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.)
Expired
Application number
GB2382355A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation Ltd
Filing date
Publication date
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Publication of GB812366A publication Critical patent/GB812366A/en
Expired legal-status Critical Current

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Classifications

    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises pyrrolo (2,3-d) pyrimidines of the general formula (I) (wherein X is a hydrogen atom or a hydroxy, amino or mercapto group and Y is a hydrogen or chlorine atom or a hydroxy, amino or mercapto group). These are prepared by cyclising acetals of the general formula (II) by the action of a strong acid, such as sulphuric acid, in a solvent such as 95 peer cent ethanol, followed if desired by interconversion of X and Y by processes of chlorination, amination, thiation or dethiation. <FORM:0812366/IV (b)/1> <FORM:0812366/IV (b)/2> In examples, 2,4-dihydroxy-, 2-mercapto-4-hydroxy -, 2 - mercapto - 4 - amino -, 2 - amino-4 - hydroxy -, 2,4 - diamino -, 4 - hydroxy - and 2 - hydroxy - 4 - amino - pyrrolo (2,3 - d)-pyrimidine are prepared from the corresponding acetals; pyrrolo (2,3-d) pyrimidine and 4-hydroxypyrrolo (2,3-d) pyrimidine are prepared by dethiating 4 - mercapto - and 2 - mercapto - 4-hydroxy-pyrrolo (2,3-d) pyrimidine respectively; 4 - chloropyrrolo (2,3-d) pyrimidine is prepared by the action of phosphorus oxychloride on the corresponding hydroxy compound, and converted to 4-mercaptopyrrolo (2,3-d)-pyrimidine by the action of thiourea, and to 4-aminopyrrolo (2,3-d) pyrimidine by the action of ammonia. Also described is an alternative preparation of 2,4-dihydroxypyrrolo (2,3-3) pyrimidine by heating together 6-amino-2,4-dihydroxypyrimidine and chloroacetaldehyde in aqueous sodium acetate. 2,4 - Dihydroxy - 6 - amino - 5 - diethoxyethylpyrimidine is prepared from urea and ethylacetalcyanoacetate (itself prepared from ethyl cyanoacetate and bromoacetal), 2-mercapto-4-hydroxy - 6 - amino - 5 - diethoxyethylpyrimidine from thiourea and ethylacetalcyanoacetate, 2-mercapto - 4,6 - diamino - 5 - diethoxyethylpyrimidine from thiourea and acetalmalononitrile, 2,6 - diamino - 4 - hydroxy - 5 - diethoxyethylpyrimidine from guanidine and ethylacetalcyanoacetate, 2,4,6 - triamino - 5 - diethoxyethylpyrimidine from guanidine and acetalmalonitrile and 2 - hydroxy - 4,6 - diamino - 5 - diethoxyethylpyrimidine from urea and acetalmalonitrile.
GB2382355A 1955-08-18 Improvements in and relating to derivatives of pyrimidine and the preparation thereof Expired GB812366A (en)

Publications (1)

Publication Number Publication Date
GB812366A true GB812366A (en) 1959-04-22

Family

ID=1737967

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2382355A Expired GB812366A (en) 1955-08-18 Improvements in and relating to derivatives of pyrimidine and the preparation thereof

Country Status (1)

Country Link
GB (1) GB812366A (en)

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3225047A (en) * 1964-02-24 1965-12-21 Bristol Myers Co N,n'-bis(pyrimidine-5-acetyl)ethylene diamines
US3296261A (en) * 1965-03-09 1967-01-03 Bristol Myers Co 6-hydroxy-pyrimidine-5-acetamides
US4571423A (en) * 1982-03-16 1986-02-18 Takeda Chemical Industries Ltd. Substituted 5-aminomethyl-2-acylaminopyrrolo[2,3-d]pyrimidin-4-ones
US4595530A (en) * 1983-03-17 1986-06-17 Takeda Chemical Industries, Ltd. Thiodeazapurine derivatives
US5349064A (en) * 1989-06-14 1994-09-20 Takeda Chemical Industries, Ltd. Production of pyrrolopyrimidines
US7429596B2 (en) 2003-06-20 2008-09-30 The Regents Of The University Of California 1H-pyrrolo [2,3-D] pyrimidine derivatives and methods of use thereof
US7585868B2 (en) 2006-04-04 2009-09-08 The Regents Of The University Of California Substituted pyrazolo[3,4-D]pyrimidines as kinase antagonists
US8476431B2 (en) 2008-11-03 2013-07-02 Itellikine LLC Benzoxazole kinase inhibitors and methods of use
US8569323B2 (en) 2009-07-15 2013-10-29 Intellikine, Llc Substituted isoquinolin-1(2H)-one compounds, compositions, and methods thereof
US8604032B2 (en) 2010-05-21 2013-12-10 Infinity Pharmaceuticals, Inc. Chemical compounds, compositions and methods for kinase modulation
US8637542B2 (en) 2008-03-14 2014-01-28 Intellikine, Inc. Kinase inhibitors and methods of use
US8697709B2 (en) 2008-10-16 2014-04-15 The Regents Of The University Of California Fused ring heteroaryl kinase inhibitors
US8703778B2 (en) 2008-09-26 2014-04-22 Intellikine Llc Heterocyclic kinase inhibitors
US8703777B2 (en) 2008-01-04 2014-04-22 Intellikine Llc Certain chemical entities, compositions and methods
US8785454B2 (en) 2009-05-07 2014-07-22 Intellikine Llc Heterocyclic compounds and uses thereof
US8785470B2 (en) 2011-08-29 2014-07-22 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US8809349B2 (en) 2011-01-10 2014-08-19 Infinity Pharmaceuticals, Inc. Processes for preparing isoquinolinones and solid forms of isoquinolinones
US8828998B2 (en) 2012-06-25 2014-09-09 Infinity Pharmaceuticals, Inc. Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors
US8901133B2 (en) 2010-11-10 2014-12-02 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US8940742B2 (en) 2012-04-10 2015-01-27 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US8969363B2 (en) 2011-07-19 2015-03-03 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US8980899B2 (en) 2009-10-16 2015-03-17 The Regents Of The University Of California Methods of inhibiting Ire1
US8993580B2 (en) 2008-03-14 2015-03-31 Intellikine Llc Benzothiazole kinase inhibitors and methods of use
US9056877B2 (en) 2011-07-19 2015-06-16 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9096611B2 (en) 2008-07-08 2015-08-04 Intellikine Llc Kinase inhibitors and methods of use
US9295673B2 (en) 2011-02-23 2016-03-29 Intellikine Llc Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof
US9321772B2 (en) 2011-09-02 2016-04-26 The Regents Of The University Of California Substituted pyrazolo[3,4-D]pyrimidines and uses thereof
US9359365B2 (en) 2013-10-04 2016-06-07 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9359349B2 (en) 2007-10-04 2016-06-07 Intellikine Llc Substituted quinazolines as kinase inhibitors
US9481667B2 (en) 2013-03-15 2016-11-01 Infinity Pharmaceuticals, Inc. Salts and solid forms of isoquinolinones and composition comprising and methods of using the same
US9512125B2 (en) 2004-11-19 2016-12-06 The Regents Of The University Of California Substituted pyrazolo[3.4-D] pyrimidines as anti-inflammatory agents
JP2017008027A (en) * 2007-06-08 2017-01-12 セノミックス インコーポレイテッド Modulation of chemosensory receptors and ligands associated therewith
US9629843B2 (en) 2008-07-08 2017-04-25 The Regents Of The University Of California MTOR modulators and uses thereof
US9708348B2 (en) 2014-10-03 2017-07-18 Infinity Pharmaceuticals, Inc. Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof
US9751888B2 (en) 2013-10-04 2017-09-05 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9775844B2 (en) 2014-03-19 2017-10-03 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US10087154B2 (en) 2008-07-31 2018-10-02 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US10131668B2 (en) 2012-09-26 2018-11-20 The Regents Of The University Of California Substituted imidazo[1,5-a]pYRAZINES for modulation of IRE1
US10160761B2 (en) 2015-09-14 2018-12-25 Infinity Pharmaceuticals, Inc. Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same
US10759806B2 (en) 2016-03-17 2020-09-01 Infinity Pharmaceuticals, Inc. Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors
US10919914B2 (en) 2016-06-08 2021-02-16 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US11110096B2 (en) 2014-04-16 2021-09-07 Infinity Pharmaceuticals, Inc. Combination therapies
US11147818B2 (en) 2016-06-24 2021-10-19 Infinity Pharmaceuticals, Inc. Combination therapies
US11897889B2 (en) 2020-08-18 2024-02-13 Incyte Corporation Process and intermediates for preparing a JAK1 inhibitor
US11905292B2 (en) 2020-08-18 2024-02-20 Incyte Corporation Process and intermediates for preparing a JAK inhibitor
US11945813B2 (en) 2018-08-07 2024-04-02 Firmenich Incorporated 5-substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof

Cited By (90)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3225047A (en) * 1964-02-24 1965-12-21 Bristol Myers Co N,n'-bis(pyrimidine-5-acetyl)ethylene diamines
US3296261A (en) * 1965-03-09 1967-01-03 Bristol Myers Co 6-hydroxy-pyrimidine-5-acetamides
US4571423A (en) * 1982-03-16 1986-02-18 Takeda Chemical Industries Ltd. Substituted 5-aminomethyl-2-acylaminopyrrolo[2,3-d]pyrimidin-4-ones
US4595530A (en) * 1983-03-17 1986-06-17 Takeda Chemical Industries, Ltd. Thiodeazapurine derivatives
US5349064A (en) * 1989-06-14 1994-09-20 Takeda Chemical Industries, Ltd. Production of pyrrolopyrimidines
US5496946A (en) * 1989-06-14 1996-03-05 Takeda Chemical Industries, Ltd. Production of pyrrolopyrimidines and intermediates therefor
US7429596B2 (en) 2003-06-20 2008-09-30 The Regents Of The University Of California 1H-pyrrolo [2,3-D] pyrimidine derivatives and methods of use thereof
US9512125B2 (en) 2004-11-19 2016-12-06 The Regents Of The University Of California Substituted pyrazolo[3.4-D] pyrimidines as anti-inflammatory agents
US7585868B2 (en) 2006-04-04 2009-09-08 The Regents Of The University Of California Substituted pyrazolo[3,4-D]pyrimidines as kinase antagonists
US8642604B2 (en) 2006-04-04 2014-02-04 The Regents Of The University Of California Substituted pyrazolo[3,2-d]pyrimidines as anti-cancer agents
US9493467B2 (en) 2006-04-04 2016-11-15 The Regents Of The University Of California PI3 kinase antagonists
JP2017008027A (en) * 2007-06-08 2017-01-12 セノミックス インコーポレイテッド Modulation of chemosensory receptors and ligands associated therewith
US9359349B2 (en) 2007-10-04 2016-06-07 Intellikine Llc Substituted quinazolines as kinase inhibitors
US11433065B2 (en) 2008-01-04 2022-09-06 Intellikine Llc Certain chemical entities, compositions and methods
US9822131B2 (en) 2008-01-04 2017-11-21 Intellikine Llc Certain chemical entities, compositions and methods
US9216982B2 (en) 2008-01-04 2015-12-22 Intellikine Llc Certain chemical entities, compositions and methods
US8703777B2 (en) 2008-01-04 2014-04-22 Intellikine Llc Certain chemical entities, compositions and methods
US9655892B2 (en) 2008-01-04 2017-05-23 Intellikine Llc Certain chemical entities, compositions and methods
US8785456B2 (en) 2008-01-04 2014-07-22 Intellikine Llc Substituted isoquinolin-1(2H)-ones, and methods of use thereof
US8637542B2 (en) 2008-03-14 2014-01-28 Intellikine, Inc. Kinase inhibitors and methods of use
US9637492B2 (en) 2008-03-14 2017-05-02 Intellikine Llc Benzothiazole kinase inhibitors and methods of use
US8993580B2 (en) 2008-03-14 2015-03-31 Intellikine Llc Benzothiazole kinase inhibitors and methods of use
US9096611B2 (en) 2008-07-08 2015-08-04 Intellikine Llc Kinase inhibitors and methods of use
US9828378B2 (en) 2008-07-08 2017-11-28 Intellikine Llc Kinase inhibitors and methods of use
US9629843B2 (en) 2008-07-08 2017-04-25 The Regents Of The University Of California MTOR modulators and uses thereof
US10308621B2 (en) 2008-07-31 2019-06-04 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US10087154B2 (en) 2008-07-31 2018-10-02 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US10570105B2 (en) 2008-07-31 2020-02-25 Firmenich Incorporated Processes and intermediates for making sweet taste enhancers
US8703778B2 (en) 2008-09-26 2014-04-22 Intellikine Llc Heterocyclic kinase inhibitors
US9296742B2 (en) 2008-09-26 2016-03-29 Intellikine Llc Heterocyclic kinase inhibitors
US9790228B2 (en) 2008-09-26 2017-10-17 Intellikine Llc Heterocyclic kinase inhibitors
US8697709B2 (en) 2008-10-16 2014-04-15 The Regents Of The University Of California Fused ring heteroaryl kinase inhibitors
US8476431B2 (en) 2008-11-03 2013-07-02 Itellikine LLC Benzoxazole kinase inhibitors and methods of use
US8476282B2 (en) 2008-11-03 2013-07-02 Intellikine Llc Benzoxazole kinase inhibitors and methods of use
US8785454B2 (en) 2009-05-07 2014-07-22 Intellikine Llc Heterocyclic compounds and uses thereof
US9315505B2 (en) 2009-05-07 2016-04-19 Intellikine Llc Heterocyclic compounds and uses thereof
US9522146B2 (en) 2009-07-15 2016-12-20 Intellikine Llc Substituted Isoquinolin-1(2H)-one compounds, compositions, and methods thereof
US9206182B2 (en) 2009-07-15 2015-12-08 Intellikine Llc Substituted isoquinolin-1(2H)-one compounds, compositions, and methods thereof
US8569323B2 (en) 2009-07-15 2013-10-29 Intellikine, Llc Substituted isoquinolin-1(2H)-one compounds, compositions, and methods thereof
US8980899B2 (en) 2009-10-16 2015-03-17 The Regents Of The University Of California Methods of inhibiting Ire1
US8604032B2 (en) 2010-05-21 2013-12-10 Infinity Pharmaceuticals, Inc. Chemical compounds, compositions and methods for kinase modulation
US9181221B2 (en) 2010-05-21 2015-11-10 Infinity Pharmaceuticals, Inc. Chemical compounds, compositions and methods for kinase modulation
US9738644B2 (en) 2010-05-21 2017-08-22 Infinity Pharmaceuticals, Inc. Chemical compounds, compositions and methods for kinase modulation
US8901133B2 (en) 2010-11-10 2014-12-02 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9388183B2 (en) 2010-11-10 2016-07-12 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9840505B2 (en) 2011-01-10 2017-12-12 Infinity Pharmaceuticals, Inc. Solid forms of (S)-3-(1-(9H-purin-6-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-1 (2H)-one and methods of use thereof
US9290497B2 (en) 2011-01-10 2016-03-22 Infinity Pharmaceuticals, Inc. Processes for preparing isoquinolinones and solid forms of isoquinolinones
US8809349B2 (en) 2011-01-10 2014-08-19 Infinity Pharmaceuticals, Inc. Processes for preparing isoquinolinones and solid forms of isoquinolinones
USRE46621E1 (en) 2011-01-10 2017-12-05 Infinity Pharmaceuticals, Inc. Processes for preparing isoquinolinones and solid forms of isoquinolinones
US11312718B2 (en) 2011-01-10 2022-04-26 Infinity Pharmaceuticals, Inc. Formulations of (S)-3-(1-(9H-purin-6-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one
US10550122B2 (en) 2011-01-10 2020-02-04 Infinity Pharmaceuticals, Inc. Solid forms of (S)-3-(1-(9H-purin-6-ylamino)ethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one and methods of use thereof
US9295673B2 (en) 2011-02-23 2016-03-29 Intellikine Llc Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof
US8969363B2 (en) 2011-07-19 2015-03-03 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9056877B2 (en) 2011-07-19 2015-06-16 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9605003B2 (en) 2011-07-19 2017-03-28 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9718815B2 (en) 2011-07-19 2017-08-01 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9546180B2 (en) 2011-08-29 2017-01-17 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US8785470B2 (en) 2011-08-29 2014-07-22 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9115141B2 (en) 2011-08-29 2015-08-25 Infinity Pharmaceuticals, Inc. Substituted isoquinolinones and methods of treatment thereof
US9895373B2 (en) 2011-09-02 2018-02-20 The Regents Of The University Of California Substituted pyrazolo[3,4-D]pyrimidines and uses thereof
US9321772B2 (en) 2011-09-02 2016-04-26 The Regents Of The University Of California Substituted pyrazolo[3,4-D]pyrimidines and uses thereof
US8940742B2 (en) 2012-04-10 2015-01-27 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9255108B2 (en) 2012-04-10 2016-02-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
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US9527847B2 (en) 2012-06-25 2016-12-27 Infinity Pharmaceuticals, Inc. Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors
US10822340B2 (en) 2012-09-26 2020-11-03 The Regents Of The University Of California Substituted imidazolopyrazine compounds and methods of using same
US11613544B2 (en) 2012-09-26 2023-03-28 The Regents Of The University Of California Substituted imidazo[1,5-a]pyrazines for modulation of IRE1
US10131668B2 (en) 2012-09-26 2018-11-20 The Regents Of The University Of California Substituted imidazo[1,5-a]pYRAZINES for modulation of IRE1
US9481667B2 (en) 2013-03-15 2016-11-01 Infinity Pharmaceuticals, Inc. Salts and solid forms of isoquinolinones and composition comprising and methods of using the same
US9751888B2 (en) 2013-10-04 2017-09-05 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9828377B2 (en) 2013-10-04 2017-11-28 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US10329299B2 (en) 2013-10-04 2019-06-25 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9359365B2 (en) 2013-10-04 2016-06-07 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US11541059B2 (en) 2014-03-19 2023-01-03 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
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US9775844B2 (en) 2014-03-19 2017-10-03 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US11944631B2 (en) 2014-04-16 2024-04-02 Infinity Pharmaceuticals, Inc. Combination therapies
US11110096B2 (en) 2014-04-16 2021-09-07 Infinity Pharmaceuticals, Inc. Combination therapies
US10253047B2 (en) 2014-10-03 2019-04-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US10941162B2 (en) 2014-10-03 2021-03-09 Infinity Pharmaceuticals, Inc. Heterocyclic compounds and uses thereof
US9708348B2 (en) 2014-10-03 2017-07-18 Infinity Pharmaceuticals, Inc. Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof
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