WO2002034729A1 - Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds - Google Patents

Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds Download PDF

Info

Publication number
WO2002034729A1
WO2002034729A1 PCT/HU2001/000103 HU0100103W WO0234729A1 WO 2002034729 A1 WO2002034729 A1 WO 2002034729A1 HU 0100103 W HU0100103 W HU 0100103W WO 0234729 A1 WO0234729 A1 WO 0234729A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
general formula
alkyl group
optionally substituted
triazoles
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.)
Ceased
Application number
PCT/HU2001/000103
Other languages
English (en)
French (fr)
Other versions
WO2002034729A8 (en
Inventor
Sándor BOKOTEY
Éva CSIKÓS
Csaba GÖNCZI
Félix HAJDÚ
István HERMECZ
Gergely HÉJA
Benjámin PODÁNYI
Andrea SÁNTÁNÉ CSUTOR
Tiborné SZOMOR
Györgyné SZVOBODA
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.)
Sanofi Aventis France
Original Assignee
Sanofi Synthelabo SA
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.)
Filing date
Publication date
Priority to US10/415,042 priority Critical patent/US20040039203A1/en
Priority to CA002427045A priority patent/CA2427045A1/en
Priority to PL01360786A priority patent/PL360786A1/xx
Priority to HR20030424A priority patent/HRP20030424A2/xx
Priority to JP2002537720A priority patent/JP2004512329A/ja
Priority to MXPA03003506A priority patent/MXPA03003506A/es
Priority to SK511-2003A priority patent/SK5112003A3/sk
Priority to BR0114828-1A priority patent/BR0114828A/pt
Application filed by Sanofi Synthelabo SA filed Critical Sanofi Synthelabo SA
Priority to AU2002214170A priority patent/AU2002214170A1/en
Priority to HU0303346A priority patent/HUP0303346A2/hu
Priority to EP01982628A priority patent/EP1337519A1/en
Publication of WO2002034729A1 publication Critical patent/WO2002034729A1/en
Anticipated expiration legal-status Critical
Publication of WO2002034729A8 publication Critical patent/WO2002034729A8/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Definitions

  • R is -salkyl group; C 3 - ⁇ 3 cycloalkyl-Co- 4 alkyl group, optionally substituted by one or more 15 C ⁇ - 3 alkyl group; phenyl-Co- alkyl-, (CH ) n -morpholino-, piperidino-, pyrrolidino- or piperazino-group, optionally substituted by one or more halogen atom, C]- 3 alkyl group,
  • n 1-5
  • R 1 , R 2 , R 3 , and R 4 independently stand for hydrogen, halogen, C h alky! group, C ⁇ - 3 alkoxy 20 group or trifluoromethyl group, with the proviso that at least one of the substituents R 1 , R 2 ,
  • R 3 , and R 4 stands for hydrogen.
  • the substituted aminoguanidine is synthesized step-by step starting from hydrazide and cyanamide, the ring closure is carried out by thermolysis in pyridine hydrochloride.
  • the synthesis does not utilize some reasonable possibilities given in the aminoguanidine structure [Ger. Offen. 1,808,677 (C.A. 72, 90561m 1970)].
  • n 1-5
  • R 1 , R 2 , R 3 , and R 4 are the same as defined above and R 5 stands for hydrogen atom or for -salkyl group- in the presence of an alkali alcoholate.
  • aldehydes of formula II are commercially available or they can be prepared by methods known from the literature. In the process according to the invention for alkali alcoholate preferably sodium- or potassium alcoholate is used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/HU2001/000103 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds Ceased WO2002034729A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
SK511-2003A SK5112003A3 (en) 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4- triazoles and substituted aminoguanidines as intermediate compounds
PL01360786A PL360786A1 (en) 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds
HR20030424A HRP20030424A2 (en) 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds
JP2002537720A JP2004512329A (ja) 2000-10-26 2001-10-25 １，５−二置換−３−アミノ−１，２，４−トリアゾールおよび中間体化合物としての置換アミノグアニジンの製造方法
MXPA03003506A MXPA03003506A (es) 2000-10-26 2001-10-25 Procedimiento para la preparacion de 1,5-disubstituidos-3-amino-1,2,3-triazoles y aminoguanidinas substituidas como compuestos intermedios.
BR0114828-1A BR0114828A (pt) 2000-10-26 2001-10-25 Processo para a preparação de 1,5-dissubstituìdo-3-amino-1,2,4-triazóis e aminoguanidinas substituìdas como compostos intermediários
AU2002214170A AU2002214170A1 (en) 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds
US10/415,042 US20040039203A1 (en) 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4,-triazoles and substituted aminoguanidines as intermediate compounds
CA002427045A CA2427045A1 (en) 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds
HU0303346A HUP0303346A2 (hu) 2000-10-26 2001-10-25 Eljárás 1,5-diszubsztituált-3-amino-1,2,4-triazolok előállítására
EP01982628A EP1337519A1 (en) 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituated-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU0004154A HUP0004154A3 (en) 2000-10-26 2000-10-26 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazole derivatives
HUP0004154 2000-10-26

Publications (2)

Publication Number Publication Date
WO2002034729A1 true WO2002034729A1 (en) 2002-05-02
WO2002034729A8 WO2002034729A8 (en) 2004-04-08

Family

ID=89978699

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU2001/000103 Ceased WO2002034729A1 (en) 2000-10-26 2001-10-25 Process for the preparation of 1,5-disubstituted-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds

Country Status (14)

Country Link
US (1) US20040039203A1 (enExample)
EP (1) EP1337519A1 (enExample)
JP (1) JP2004512329A (enExample)
CN (1) CN1471516A (enExample)
AU (1) AU2002214170A1 (enExample)
BR (1) BR0114828A (enExample)
CA (1) CA2427045A1 (enExample)
CZ (1) CZ20031437A3 (enExample)
HR (1) HRP20030424A2 (enExample)
HU (1) HUP0004154A3 (enExample)
MX (1) MXPA03003506A (enExample)
PL (1) PL360786A1 (enExample)
SK (1) SK5112003A3 (enExample)
WO (1) WO2002034729A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025022310A1 (en) * 2023-07-25 2025-01-30 Pi Industries Ltd. A method for preparing 1-alkyl-1h-1,2,4-traizol-3-amine compounds

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1537892A (fr) * 1966-07-21 1968-08-30 British Petroleum Co Composition de lubrifiant synthétique
DE1808677A1 (de) * 1967-11-14 1970-01-02 Merck & Co Inc Triazolylaminopyrazine und Verfahren zu deren Herstellung
US3541217A (en) * 1969-06-30 1970-11-17 Lilly Co Eli Omicron-chlorobenzylaminoguanidine for treating bovine ketosis
US3541218A (en) * 1969-06-18 1970-11-17 Lilly Co Eli Omicron-fluorobenzylaminoguanidine for diabetes
CH530965A (de) * 1964-05-05 1972-11-30 Wander Ag Dr A Verfahren zur Herstellung von 2,6-Dihalogen-phenylalkylaminoguanidinen
CH530964A (de) * 1964-05-05 1972-11-30 Wander Ag Dr A Verfahren zur Herstellung von Phenylalkylaminoguanidinen
US3714363A (en) * 1970-08-11 1973-01-30 Sandoz Ag Substituted amino guanidine as anti-diabetic agents
CH533603A (de) * 1966-06-02 1973-02-15 Wander Ag Dr A Verfahren zur Herstellung von Phenylalkylaminoguanidinen
DE4321109A1 (de) * 1993-06-25 1995-01-05 Sanol Arznei Schwarz Gmbh Verbindungen mit Nitrosohydrazinpartialstruktur
WO1999055321A1 (en) * 1998-04-24 1999-11-04 Mitokor Compounds and methods for treating mitochondria-associated diseases

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5994577A (en) * 1994-11-23 1999-11-30 Larsen; Scott D. Aminoguanidine carboxylates for the treatment of non-insulin-dependent diabetes mellitus

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH530965A (de) * 1964-05-05 1972-11-30 Wander Ag Dr A Verfahren zur Herstellung von 2,6-Dihalogen-phenylalkylaminoguanidinen
CH530964A (de) * 1964-05-05 1972-11-30 Wander Ag Dr A Verfahren zur Herstellung von Phenylalkylaminoguanidinen
CH533603A (de) * 1966-06-02 1973-02-15 Wander Ag Dr A Verfahren zur Herstellung von Phenylalkylaminoguanidinen
FR1537892A (fr) * 1966-07-21 1968-08-30 British Petroleum Co Composition de lubrifiant synthétique
DE1808677A1 (de) * 1967-11-14 1970-01-02 Merck & Co Inc Triazolylaminopyrazine und Verfahren zu deren Herstellung
US3541218A (en) * 1969-06-18 1970-11-17 Lilly Co Eli Omicron-fluorobenzylaminoguanidine for diabetes
US3541217A (en) * 1969-06-30 1970-11-17 Lilly Co Eli Omicron-chlorobenzylaminoguanidine for treating bovine ketosis
US3714363A (en) * 1970-08-11 1973-01-30 Sandoz Ag Substituted amino guanidine as anti-diabetic agents
DE4321109A1 (de) * 1993-06-25 1995-01-05 Sanol Arznei Schwarz Gmbh Verbindungen mit Nitrosohydrazinpartialstruktur
WO1999055321A1 (en) * 1998-04-24 1999-11-04 Mitokor Compounds and methods for treating mitochondria-associated diseases

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
"Remington's Pharmaceutical Sciences", 1990, MACK PUBLISHING CO.
ARM. KHIM. ZH. (1971), 24(4), 338-44 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; AROYAN, A. A. ET AL: "Syntheses based on 4-alkoxybenzylhydrazines", XP002192020, retrieved from STN Database accession no. 75:118088 *
DATABASE CROSSFIRE BEILSTEIN [online] BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFT, FRANKFURT AM MAIN, DE; XP002192019, Database accession no. 571876 *
ER-RHAIMINI, ABDERRAHMAN ET AL: "Synthesis and photochemical degradation of N-arylmethyl derivatives of the herbicide 3-amino-1,2,4-triazole", J.HETEROCYCL.CHEM. (1992), 29(6), 1561-6, XP002192018 *
GAZZ. CHIM. ITAL., vol. 29, no. I 105, 1899, pages 89 - 106 *
J. F. KING; A. HAWSON; B. L. HUSTON; L. J. DANKS; J. KOMERY: "49", CAN. J. CHEM., 1971, pages 943
J. ORG. CHEM., vol. 53, 1988, pages 3621
J. ORG. CHEM., vol. 68, 2003, pages 4123
OJA; SARANSAARI, PROC. WEST. PHARMACOL. SOC., vol. 50, 2007, pages 8 - 15
SZYMANSKY; WINIARSKA, POSTEPY. HIG. MED DOSW., vol. 62, 2008, pages 75 - 86
WARSKULAT IS MTSAI, METHODS ENZYMOL., vol. 428, 2007, pages 439 - 58

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025022310A1 (en) * 2023-07-25 2025-01-30 Pi Industries Ltd. A method for preparing 1-alkyl-1h-1,2,4-traizol-3-amine compounds

Also Published As

Publication number Publication date
HUP0004154A3 (en) 2003-11-28
AU2002214170A1 (en) 2002-05-06
JP2004512329A (ja) 2004-04-22
MXPA03003506A (es) 2004-05-04
WO2002034729A8 (en) 2004-04-08
HU0004154D0 (enExample) 2001-01-29
EP1337519A1 (en) 2003-08-27
PL360786A1 (en) 2004-09-20
CA2427045A1 (en) 2002-05-02
SK5112003A3 (en) 2004-01-08
CN1471516A (zh) 2004-01-28
CZ20031437A3 (cs) 2004-10-13
BR0114828A (pt) 2003-10-28
HRP20030424A2 (en) 2005-10-31
US20040039203A1 (en) 2004-02-26
HUP0004154A2 (hu) 2002-11-28

Similar Documents

Publication Publication Date Title
EP2799425A1 (en) Preparation process of an agonist of the thrombopoietin receptor
US6153752A (en) Process for preparing heterocycles
WO2003076374A1 (en) PROCESS FOR PRODUCING trans-4-AMINO-1-CYCLOHEXANECARBOXYLIC ACID DERIVATIVE
US5648487A (en) Process for the preparation of aminotriazine derivatives
JP2682705B2 (ja) ２，６−ジクロロフェニルアミノベンゼン酢酸誘導体及びジフェニルアミン誘導体の製造方法。
JP4770826B2 (ja) ２−オキシインドール誘導体の製造法
EP1337519A1 (en) Process for the preparation of 1,5-disubstituated-3-amino-1,2,4-triazoles and substituted aminoguanidines as intermediate compounds
JP7474754B2 (ja) ジアミノピリミジン誘導体またはその酸付加塩の新規な製造方法
CZ145489A3 (cs) Způsob přípravy dimethyl-1,4-dihydro-2,6-dimethyl-4-(2´-nitrofenyl)pyridin-3,5-dikarboxylátu
JPH0541628B2 (enExample)
JPH02202871A (ja) ３―フェニルピロール誘導体の製造方法
HU199414B (en) Process for producing substituted indolinone derivatives
US4071684A (en) Process for producing 3-substituted 1,2,4-triazines
US4948902A (en) Process for making substituted pyrazoles
JP3079221B2 (ja) ２−アミノ−４−アルコキシ−ｓ−トリアジンの製造方法
JPS5811434B2 (ja) ホルミル酢酸エステルのアシルヒドラゾンの製造法
JP4126944B2 (ja) ５−アミノ−４−ニトロソピラゾール化合物の製法
JP4078328B2 (ja) ２−オキシインドール誘導体の製造法
HU194176B (en) Process for production of derivatives of new 7-phormildekahydridinoline
US4892956A (en) 5-cyano-4,5-dihydro-3,4-dicarboxypyrazole derivatives
HUP0303346A2 (hu) Eljárás 1,5-diszubsztituált-3-amino-1,2,4-triazolok előállítására
JP2810747B2 (ja) ピリジン誘導体の製造方法
JPH04290856A (ja) モノアシル化ヒドラジンの製造方法
US4924001A (en) Process for preparing 5-cyano-4, 5-dihydro-3,4-dicarboxypyrazole derivatives
JP2011178706A (ja) アルコキシ置換トリアジン化合物の製造方法

Legal Events

Date Code Title Description
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: PA/a/2003/003506

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 432/MUMNP/2003

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2427045

Country of ref document: CA

Ref document number: 2002537720

Country of ref document: JP

Ref document number: 5112003

Country of ref document: SK

WWE Wipo information: entry into national phase

Ref document number: 018181708

Country of ref document: CN

WWE Wipo information: entry into national phase

Ref document number: 2001982628

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: PV2003-1437

Country of ref document: CZ

WWE Wipo information: entry into national phase

Ref document number: P20030424A

Country of ref document: HR

WWE Wipo information: entry into national phase

Ref document number: 10415042

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 2001982628

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i

Free format text: IN PCT GAZETTE 18/2002 UNDER (71) THE NAME SHOULD READ "SANOFI-SYNTHELABO"

WWP Wipo information: published in national office

Ref document number: PV2003-1437

Country of ref document: CZ

WWR Wipo information: refused in national office

Ref document number: PV2003-1437

Country of ref document: CZ

WWW Wipo information: withdrawn in national office

Ref document number: 2001982628

Country of ref document: EP