IE39102L - Piperazine derivatives - Google Patents
Piperazine derivativesInfo
- Publication number
- IE39102L IE39102L IE740650A IE65074A IE39102L IE 39102 L IE39102 L IE 39102L IE 740650 A IE740650 A IE 740650A IE 65074 A IE65074 A IE 65074A IE 39102 L IE39102 L IE 39102L
- Authority
- IE
- Ireland
- Prior art keywords
- ethyl
- piperazinyl
- oxo
- dihydro
- pyrimidine
- Prior art date
Links
- 150000004885 piperazines Chemical class 0.000 title 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 7
- 230000003301 hydrolyzing effect Effects 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 6
- 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 5
- 238000006228 Dieckmann condensation reaction Methods 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 230000001590 oxidative effect Effects 0.000 abstract 4
- 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
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 abstract 2
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical class OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 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)
Abstract
A process for preparing 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-c arboxylic acids(I) and its pharmaceutically acceptable salts, which comprises hydrolyzing 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-c arbonitrils(II') oxidizing 6-lower alkanoyl-8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrim idines (II"), and if desired, hydrolyzing the product; or subjecting alkyl 4-(N-substituted ethyl-N-ethyl)amino 2-(1-piperazinyl)-pyrimidine-5-carboxylates(IV) to a Dieckmann reaction, dehydrogenating the resulting 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6,7,8-tetrahydropyrido(2,3-d) pyrimidines (III), then oxidizing or hydrolyzing the resulting 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxo-pyrido(2,3-d)pyrimidines(II) and if desired, converting the resulting 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido2,3-d) pyrimidine-6-carboxylic acids(II) to a pharmaceutically acceptable salt, and a process for proparing 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido(2,3-d)pyrimidines(II), which comprises dehydrogenating 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6.7.8-tetrahydropyrido(2,3-d)pyrimid ines (III), or subjecting alkyl 4-(N-substituted ethyl-N-ethyl)amino-2-(1-piperazinyl)-pyrimidine-5-carboxylates(IV) to a Dieckmann reaction, and dehydrogenating the resulting 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6,7,8-tetrahydropyrido(2,3-d)pyrimid ines(III). The 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl) pyrido(2,3-d)pyrimidine-6-carboxylic acids (I) and their pharmaceutically acceptable salts are useful as antibacterial agents, and 5 8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido(2,3-c)pyrimidines (II) are used as intermediates for producing the 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl) pyrido(2,3-d)pyrimidine-6-carboxylic acids (I).
A process for preparing 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acids(I) and its pharmaceutically acceptable salts, which comprises hydrolyzing 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carbonitrils(II') oxidizing 6-lower alkanoyl-8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidines (II"), and if desired, hydrolyzing the product; or subjecting alkyl 4-(N-substituted ethyl-N-ethyl)amino 2-(1-piperazinyl)-pyrimidine-5-carboxylates(IV) to a Dieckmann reaction, dehydrogenating the resulting 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6,7,8-tetrahydropyrido(2,3-d) pyrimidines (III), then oxidizing or hydrolyzing the resulting 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxo-pyrido(2,3-d)pyrimidines(II) and if desired, converting the resulting 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido¢2,3-d) pyrimidine-6-carboxylic acids(II) to a pharmaceutically acceptable salt, and a process for proparing 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido(2,3-d)pyrimidines(II), which comprises dehydrogenating 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6.7.8-tetrahydropyrido(2,3-d)pyrimidines (III), or subjecting alkyl 4-(N-substituted ethyl-N-ethyl)amino-2-(1-piperazinyl)-pyrimidine-5-carboxylates(IV) to a Dieckmann reaction, and dehydrogenating the resulting 8-ethyl-2-(1-piperazinyl)-5-oxo-5,6,7,8-tetrahydropyrido(2,3-d)pyrimidines(III). The 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl) pyrido(2,3-d)pyrimidine-6-carboxylic acids (I) and their pharmaceutically acceptable salts are useful as antibacterial agents, and 5 8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido(2,3-c)pyrimidines (II) are used as intermediates for producing the 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl) pyrido(2,3-d)pyrimidine-6-carboxylic acids (I).
[CA1066701A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3845373A JPS5546400B2 (en) | 1973-04-03 | 1973-04-03 | |
| JP5654473A JPS565753B2 (en) | 1973-05-21 | 1973-05-21 | |
| JP6446473A JPS565755B2 (en) | 1973-06-07 | 1973-06-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE39102L true IE39102L (en) | 1974-10-03 |
| IE39102B1 IE39102B1 (en) | 1978-08-02 |
Family
ID=27289838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE00650/74A IE39102B1 (en) | 1973-04-03 | 1974-03-25 | Method for the preparation of piperazine derivatives |
Country Status (11)
| Country | Link |
|---|---|
| AR (2) | AR204003A1 (en) |
| AT (1) | AT340931B (en) |
| CA (1) | CA1066701A (en) |
| CH (1) | CH593281A5 (en) |
| ES (1) | ES424851A1 (en) |
| FI (1) | FI56011C (en) |
| IE (1) | IE39102B1 (en) |
| NL (1) | NL186087C (en) |
| NO (1) | NO142221C (en) |
| PH (2) | PH10529A (en) |
| SE (1) | SE416051B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1209163B (en) * | 1979-12-21 | 1989-07-10 | Unibios S P A Trecate Novara | PROCEDURE FOR THE MANUFACTURE OF: 6-ALCOSSICARBONIL-8-ETHYL-5-OXO-5,8 DIIDRO-APERTA PAR. SQUARE 2,3-DCHIUSA PAR. SQUARE-PRIMIDINE 2-REPLACED AND ACID CORRESPONDING BOOKS. |
| PT2448938E (en) | 2009-06-29 | 2014-07-31 | Incyte Corp | Pyrimidinones as pi3k inhibitors |
| TW201130842A (en) | 2009-12-18 | 2011-09-16 | Incyte Corp | Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors |
| WO2011075643A1 (en) | 2009-12-18 | 2011-06-23 | Incyte Corporation | Substituted heteroaryl fused derivatives as pi3k inhibitors |
| JP5961187B2 (en) | 2010-12-20 | 2016-08-02 | インサイト・ホールディングス・コーポレイションＩｎｃｙｔｅ Ｈｏｌｄｉｎｇｓ Ｃｏｒｐｏｒａｔｉｏｎ | N- (1- (substituted phenyl) ethyl) -9H-purin-6-amine as a PI3K inhibitor |
| EP3196202B1 (en) | 2011-09-02 | 2019-02-27 | Incyte Holdings Corporation | Heterocyclylamines as pi3k inhibitors |
| AR090548A1 (en) | 2012-04-02 | 2014-11-19 | Incyte Corp | BICYCLIC AZAHETEROCICLOBENCILAMINS AS PI3K INHIBITORS |
| US10077277B2 (en) | 2014-06-11 | 2018-09-18 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as PI3K inhibitors |
| PL3262046T3 (en) | 2015-02-27 | 2021-05-04 | Incyte Corporation | Salts of pi3k inhibitor and processes for their preparation |
| WO2016183060A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
| WO2016183063A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Crystalline forms of a pi3k inhibitor |
| KR102884803B1 (en) | 2018-06-01 | 2025-11-12 | 인사이트 코포레이션 | Dosage regimens for the treatment of PI3K-related disorders |
-
1974
- 1974-01-01 AR AR253060A patent/AR204003A1/en active
- 1974-01-30 CA CA191,286A patent/CA1066701A/en not_active Expired
- 1974-02-01 SE SE7401361A patent/SE416051B/en not_active IP Right Cessation
- 1974-02-04 NL NLAANVRAGE7401509,A patent/NL186087C/en not_active IP Right Cessation
- 1974-02-04 NO NO740349A patent/NO142221C/en unknown
- 1974-02-04 FI FI298/74A patent/FI56011C/en active
- 1974-02-14 CH CH205474A patent/CH593281A5/en not_active IP Right Cessation
- 1974-03-25 IE IE00650/74A patent/IE39102B1/en unknown
- 1974-04-02 ES ES424851A patent/ES424851A1/en not_active Expired
- 1974-04-03 PH PH15698A patent/PH10529A/en unknown
- 1974-04-03 AT AT277774A patent/AT340931B/en not_active IP Right Cessation
-
1975
- 1975-01-01 AR AR258571A patent/AR204660A1/en active
- 1975-09-05 PH PH17546A patent/PH10984A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1066701A (en) | 1979-11-20 |
| CH593281A5 (en) | 1977-11-30 |
| NO142221B (en) | 1980-04-08 |
| NL7401509A (en) | 1974-10-07 |
| PH10984A (en) | 1977-10-18 |
| AT340931B (en) | 1978-01-10 |
| IE39102B1 (en) | 1978-08-02 |
| NL186087C (en) | 1990-09-17 |
| NO740349L (en) | 1974-10-04 |
| FI56011B (en) | 1979-07-31 |
| ATA277774A (en) | 1977-05-15 |
| ES424851A1 (en) | 1976-06-01 |
| PH10529A (en) | 1977-05-30 |
| FI56011C (en) | 1979-11-12 |
| AR204003A1 (en) | 1975-11-12 |
| SE416051B (en) | 1980-11-24 |
| NO142221C (en) | 1980-07-16 |
| AR204660A1 (en) | 1976-02-20 |
| NL186087B (en) | 1990-04-17 |
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