CA1066701A - Method for the preparation of piperazine derivatives - Google Patents

Method for the preparation of piperazine derivatives

Info

Publication number: CA1066701A
Authority: CA; Canada
Prior art keywords: group; compound; formula; ethyl; piperazinyl
Prior art date: 1973-04-03
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

CA191,286A

Other languages

English (en)

French (fr)

Other versions

CA191286S (fr

Inventor

Jun-Ichi Matsumoto

Shinichi Nakamura

Shinsaku Minami

Masanao Shimizu

Yoshiyuki Takase

Kazuyo Kawaguchi

Shinsaku Mishio

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.)

Sumitomo Pharma Co Ltd

Original Assignee

Dainippon Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1973-04-03

Filing date

1974-01-30

Publication date

1979-11-20

1973-04-03 Priority claimed from JP3845373A external-priority patent/JPS5546400B2/ja

1973-05-21 Priority claimed from JP5654473A external-priority patent/JPS565753B2/ja

1973-06-07 Priority claimed from JP6446473A external-priority patent/JPS565755B2/ja

1974-01-30 Application filed by Dainippon Pharmaceutical Co Ltd filed Critical Dainippon Pharmaceutical Co Ltd

1979-11-20 Application granted granted Critical

1979-11-20 Publication of CA1066701A publication Critical patent/CA1066701A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 26
150000004885 piperazines Chemical class 0.000 title description 3
238000002360 preparation method Methods 0.000 title description 3
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 10
230000003301 hydrolyzing effect Effects 0.000 claims abstract description 9
238000006228 Dieckmann condensation reaction Methods 0.000 claims abstract description 6
230000001590 oxidative effect Effects 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 85
125000002252 acyl group Chemical group 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
239000000543 intermediate Substances 0.000 abstract description 30
-1 amino 2-(1-piperazinyl)-pyrimidine-5-carboxylates Chemical class 0.000 abstract description 18
239000002253 acid Substances 0.000 abstract description 8
239000003242 anti bacterial agent Substances 0.000 abstract description 4
JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical class N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 abstract description 4
YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical class OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 abstract description 2
DWUNHXXOHDQQFW-UHFFFAOYSA-N 8-ethyl-2-piperazin-1-yl-6,7-dihydropyrido[2,3-d]pyrimidin-5-one Chemical class N1=C2N(CC)CCC(=O)C2=CN=C1N1CCNCC1 DWUNHXXOHDQQFW-UHFFFAOYSA-N 0.000 abstract 3
150000003230 pyrimidines Chemical class 0.000 abstract 2
159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 abstract 1
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
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HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
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238000007912 intraperitoneal administration Methods 0.000 description 4
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230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
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238000005303 weighing Methods 0.000 description 4
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235000019698 starch Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
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241000589517 Pseudomonas aeruginosa Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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230000001580 bacterial effect Effects 0.000 description 2
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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230000003197 catalytic effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940093476 ethylene glycol Drugs 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
ZIEWSZYVEDTXGH-UHFFFAOYSA-N pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC=N1 ZIEWSZYVEDTXGH-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
SAFWHKYSCUAGHQ-UHFFFAOYSA-N sodium;hypoiodite Chemical compound [Na+].I[O-] SAFWHKYSCUAGHQ-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000007864 suspending Methods 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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
- C07D239/48—Two nitrogen atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA191,286A 1973-04-03 1974-01-30 Method for the preparation of piperazine derivatives Expired CA1066701A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
JP3845373A JPS5546400B2 (xx)	1973-04-03	1973-04-03
JP5654473A JPS565753B2 (xx)	1973-05-21	1973-05-21
JP6446473A JPS565755B2 (xx)	1973-06-07	1973-06-07

Publications (1)

Publication Number	Publication Date
CA1066701A true CA1066701A (en)	1979-11-20

Family

ID=27289838

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA191,286A Expired CA1066701A (en)	1973-04-03	1974-01-30	Method for the preparation of piperazine derivatives

Country Status (11)

Country	Link
AR (2)	AR204003A1 (xx)
AT (1)	AT340931B (xx)
CA (1)	CA1066701A (xx)
CH (1)	CH593281A5 (xx)
ES (1)	ES424851A1 (xx)
FI (1)	FI56011C (xx)
IE (1)	IE39102B1 (xx)
NL (1)	NL186087C (xx)
NO (1)	NO142221C (xx)
PH (2)	PH10529A (xx)
SE (1)	SE416051B (xx)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0031120A1 (en) *	1979-12-21	1981-07-01	Unibios S.p.A.	A process for the production of 2-substituted 6-alkoxycarbonyl-8-ethyl-5-oxo-5,8-dihydro-pyrido(2,3-d)-pyrimidines and of corresponding free acids
US8680108B2 (en)	2009-12-18	2014-03-25	Incyte Corporation	Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors
US8759359B2 (en)	2009-12-18	2014-06-24	Incyte Corporation	Substituted heteroaryl fused derivatives as PI3K inhibitors
US8940752B2 (en)	2009-06-29	2015-01-27	Incyte Corporation	Pyrimidinones as PI3K inhibitors
US9199982B2 (en)	2011-09-02	2015-12-01	Incyte Holdings Corporation	Heterocyclylamines as PI3K inhibitors
US9527848B2 (en)	2010-12-20	2016-12-27	Incyte Holdings Corporation	N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors
US9732097B2 (en)	2015-05-11	2017-08-15	Incyte Corporation	Process for the synthesis of a phosphoinositide 3-kinase inhibitor
US9944646B2 (en)	2012-04-02	2018-04-17	Incyte Holdings Corporation	Bicyclic azaheterocyclobenzylamines as PI3K inhibitors
US9988401B2 (en)	2015-05-11	2018-06-05	Incyte Corporation	Crystalline forms of a PI3K inhibitor
US10077277B2 (en)	2014-06-11	2018-09-18	Incyte Corporation	Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US10336759B2 (en)	2015-02-27	2019-07-02	Incyte Corporation	Salts and processes of preparing a PI3K inhibitor
US12226418B2 (en)	2019-05-31	2025-02-18	Incyte Corporation	Dosing regimen for the treatment of PI3K related disorders

1974
- 1974-01-01 AR AR253060A patent/AR204003A1/es active
- 1974-01-30 CA CA191,286A patent/CA1066701A/en not_active Expired
- 1974-02-01 SE SE7401361A patent/SE416051B/xx not_active IP Right Cessation
- 1974-02-04 NL NLAANVRAGE7401509,A patent/NL186087C/xx not_active IP Right Cessation
- 1974-02-04 FI FI298/74A patent/FI56011C/fi active
- 1974-02-04 NO NO740349A patent/NO142221C/no unknown
- 1974-02-14 CH CH205474A patent/CH593281A5/de not_active IP Right Cessation
- 1974-03-25 IE IE00650/74A patent/IE39102B1/xx unknown
- 1974-04-02 ES ES424851A patent/ES424851A1/es not_active Expired
- 1974-04-03 PH PH15698A patent/PH10529A/en unknown
- 1974-04-03 AT AT277774A patent/AT340931B/de not_active IP Right Cessation
1975
- 1975-01-01 AR AR258571A patent/AR204660A1/es active
- 1975-09-05 PH PH17546A patent/PH10984A/en unknown

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0031120A1 (en) *	1979-12-21	1981-07-01	Unibios S.p.A.	A process for the production of 2-substituted 6-alkoxycarbonyl-8-ethyl-5-oxo-5,8-dihydro-pyrido(2,3-d)-pyrimidines and of corresponding free acids
US9975907B2 (en)	2009-06-29	2018-05-22	Incyte Holdings Corporation	Pyrimidinones as PI3K inhibitors
US8940752B2 (en)	2009-06-29	2015-01-27	Incyte Corporation	Pyrimidinones as PI3K inhibitors
US10829502B2 (en)	2009-06-29	2020-11-10	Incyte Corporation	Pyrimidinones as PI3K inhibitors
US11401280B2 (en)	2009-06-29	2022-08-02	Incyte Holdings Corporation	Pyrimidinones as PI3K inhibitors
US10428087B2 (en)	2009-06-29	2019-10-01	Incyte Corporation	Pyrimidinones as PI3K inhibitors
US8680108B2 (en)	2009-12-18	2014-03-25	Incyte Corporation	Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors
US8759359B2 (en)	2009-12-18	2014-06-24	Incyte Corporation	Substituted heteroaryl fused derivatives as PI3K inhibitors
US9527848B2 (en)	2010-12-20	2016-12-27	Incyte Holdings Corporation	N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors
US9815839B2 (en)	2010-12-20	2017-11-14	Incyte Corporation	N-(1-(substituted-phenyl)ethyl)-9H-purin-6-amines as PI3K inhibitors
US9730939B2 (en)	2011-09-02	2017-08-15	Incyte Holdings Corporation	Heterocyclylamines as PI3K inhibitors
US11819505B2 (en)	2011-09-02	2023-11-21	Incyte Corporation	Heterocyclylamines as PI3K inhibitors
US11433071B2 (en)	2011-09-02	2022-09-06	Incyte Corporation	Heterocyclylamines as PI3K inhibitors
US12201636B2 (en)	2011-09-02	2025-01-21	Incyte Corporation	Heterocyclylamines as PI3K inhibitors
US10092570B2 (en)	2011-09-02	2018-10-09	Incyte Holdings Corporation	Heterocyclylamines as PI3K inhibitors
US9707233B2 (en)	2011-09-02	2017-07-18	Incyte Holdings Corporation	Heterocyclylamines as PI3K inhibitors
US9199982B2 (en)	2011-09-02	2015-12-01	Incyte Holdings Corporation	Heterocyclylamines as PI3K inhibitors
US10646492B2 (en)	2011-09-02	2020-05-12	Incyte Corporation	Heterocyclylamines as PI3K inhibitors
US10376513B2 (en)	2011-09-02	2019-08-13	Incyte Holdings Corporation	Heterocyclylamines as PI3K inhibitors
US10259818B2 (en)	2012-04-02	2019-04-16	Incyte Corporation	Bicyclic azaheterocyclobenzylamines as PI3K inhibitors
US9944646B2 (en)	2012-04-02	2018-04-17	Incyte Holdings Corporation	Bicyclic azaheterocyclobenzylamines as PI3K inhibitors
US10479803B2 (en)	2014-06-11	2019-11-19	Incyte Corporation	Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US11130767B2 (en)	2014-06-11	2021-09-28	Incyte Corporation	Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US10077277B2 (en)	2014-06-11	2018-09-18	Incyte Corporation	Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US11999751B2 (en)	2014-06-11	2024-06-04	Incyte Corporation	Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors
US10336759B2 (en)	2015-02-27	2019-07-02	Incyte Corporation	Salts and processes of preparing a PI3K inhibitor
US11084822B2 (en)	2015-02-27	2021-08-10	Incyte Corporation	Salts and processes of preparing a PI3K inhibitor
US12024522B2 (en)	2015-02-27	2024-07-02	Incyte Corporation	Salts and processes of preparing a PI3K inhibitor
US10125150B2 (en)	2015-05-11	2018-11-13	Incyte Corporation	Crystalline forms of a PI3K inhibitor
US9988401B2 (en)	2015-05-11	2018-06-05	Incyte Corporation	Crystalline forms of a PI3K inhibitor
US9732097B2 (en)	2015-05-11	2017-08-15	Incyte Corporation	Process for the synthesis of a phosphoinositide 3-kinase inhibitor
US12226418B2 (en)	2019-05-31	2025-02-18	Incyte Corporation	Dosing regimen for the treatment of PI3K related disorders

Also Published As

Publication number	Publication date
SE416051B (sv)	1980-11-24
FI56011C (fi)	1979-11-12
NO740349L (no)	1974-10-04
NL7401509A (xx)	1974-10-07
AR204660A1 (es)	1976-02-20
ATA277774A (de)	1977-05-15
NL186087C (nl)	1990-09-17
CH593281A5 (en)	1977-11-30
PH10984A (en)	1977-10-18
FI56011B (fi)	1979-07-31
IE39102L (en)	1974-10-03
NL186087B (nl)	1990-04-17
PH10529A (en)	1977-05-30
AT340931B (de)	1978-01-10
ES424851A1 (es)	1976-06-01
NO142221B (no)	1980-04-08
NO142221C (no)	1980-07-16
AR204003A1 (es)	1975-11-12
IE39102B1 (en)	1978-08-02

Publication	Publication Date	Title
US4352803A (en)	1982-10-05	Novel naphthyridine derivatives, intermediates thereof, processes for preparation thereof, and use thereof
EP0027752B1 (en)	1983-12-21	Naphthyridine derivatives, processes for their preparation and pharmaceutical compositions containing them
US3755340A (en)	1973-08-28	Amino derivatives of pyrazolopyridine carboxylic acids and esters
US3673184A (en)	1972-06-27	Certain 2-substituted-5,8-dihydro-5-oxopyrido{8 2,3-d{9 pyrimidine-6-carboxylic acid derivatives
JPH0314811B2 (xx)	1991-02-27
CA1066701A (en)	1979-11-20	Method for the preparation of piperazine derivatives
NO158507B (no)	1988-06-13	Analogifremgangsmaate for fremstilling av terapeutisk aktive 9-halogen-7-okso-2,3-dihydro-7h-pyrido (1,2,3-de)(1,4)-benzoksazin-6-karboksylsyreforbindelser.
US3887557A (en)	1975-06-03	Piperazine derivatives and processes for preparation thereof
DK162638B (da)	1991-11-25	Analogifremgangsmaade til fremstilling af 6-fluor-1,4-dihydro-4-oxo-3-quinolincarboxylsyrederivater og udgangsmateriale til brug ved fremgangsmaaden
US3962443A (en)	1976-06-08	Antibacterial pharmaceutical compositions and processes for preparation thereof
CA1073456A (en)	1980-03-11	Piperazine derivatives and processes for preparation thereof
NO860199L (no)	1986-07-11	Mellomprodukter for fremstilling av 6,7-disubstituerte 1-cyklopropyl-1,4-dihydro-4-okso-1,8-naftyridin-3-karboksylsyrer.
PL143730B1 (en)	1988-03-31	Process for preparing derivatives of 7-/pyrrolyl-1-/-1-ethyl-1,4-dihydro-4-ketoquinoline-/or-4-keto-1,8-naphtiridine/-3-carboxylic acid
JPS60233089A (ja)	1985-11-19	キノリン‐ベノキサジン抗菌性化合物
US3856799A (en)	1974-12-24	Intermediates for production of amino derivatives of pyrazolopyridine carboxylic acids and esters
EP0210025A2 (en)	1987-01-28	5-Substituted-6-aminopyrimidine derivatives, composition and uses
US3833594A (en)	1974-09-03	Amino derivatives of pyrazolopyridine carboxylic acids and esters
US3373168A (en)	1968-03-12	Certain benzazepinoxyridoindole compounds and their preparation
EP0244352B1 (en)	1993-03-31	Pyrido[4,3-d]pyrimidine derivatives
JPS5817758B2 (ja)	1983-04-09	新規な２−アミノ−８−シクロプロピル−５−オキソ−５，８−ジヒドロ−ピリド〔２，３−ｄ〕ピリミジン−６−カルボン酸化合物
US4022779A (en)	1977-05-10	Amino derivatives of pyrido(3,4-b)pyrazine carboxylic acids and esters
HU180782B (en)	1983-04-29	Process for producing pyrido-bracket-2,1-a-bracket closed-quinazoline derivatives
US3313818A (en)	1967-04-11	7, 10-dihydro-3, 10-dioxo-7-(lower-alkyl)-3h-pyrano[3, 2-f]quinoline-3-carboxylic acid derivatives
CA1073905A (en)	1980-03-18	Pyrazolo (1,5-a) pyrido (3,2-e) pyrimidine-7-carboxylic acid derivatives
US3850940A (en)	1974-11-26	Intermediate pyrazolopyridine carbonitriles