WO2005105804A1 - 7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES, AS WELL AS THEIR THERAPEUTICALLY ACCEPTABLE SALTS, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND PROCESS FOR PRODUCTION THE ACTIVE AGENT - Google Patents

7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES, AS WELL AS THEIR THERAPEUTICALLY ACCEPTABLE SALTS, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND PROCESS FOR PRODUCTION THE ACTIVE AGENT Download PDF

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Publication number
WO2005105804A1
WO2005105804A1 PCT/HU2005/000040 HU2005000040W WO2005105804A1 WO 2005105804 A1 WO2005105804 A1 WO 2005105804A1 HU 2005000040 W HU2005000040 W HU 2005000040W WO 2005105804 A1 WO2005105804 A1 WO 2005105804A1
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
alkyl
reaction
pyrrolo
methine
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/HU2005/000040
Other languages
English (en)
French (fr)
Inventor
János SZOLCSÁNYI
László Orfi
György Kéri
Frigyes Wáczek
Erika Pintér
Zsuzsanna Helyes
Tamás Szüts
József NÉMETH
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.)
Individual
Original Assignee
Individual
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
Application filed by Individual filed Critical Individual
Priority to CA002564277A priority Critical patent/CA2564277A1/en
Priority to AT05739554T priority patent/ATE462706T1/de
Priority to US11/587,851 priority patent/US20080214583A1/en
Priority to JP2007510131A priority patent/JP2007534737A/ja
Priority to DE602005020281T priority patent/DE602005020281D1/de
Priority to AU2005238287A priority patent/AU2005238287A1/en
Priority to EP05739554A priority patent/EP1756110B1/en
Publication of WO2005105804A1 publication Critical patent/WO2005105804A1/en
Priority to IL178906A priority patent/IL178906A0/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the compounds of general formula (I) are basic substances of pharmaceutical preparations of neurogenic and not neurogenic antiphlogistic, as well as paregoric effect, neuropathic hyperalgesia reducing ones, those for hindering rheumatic arthritis or treatment of destruction of bone or chondrus in joints, as well as for other diseases, which may be connected with other inflammatory processes e. g. asthma, eczema, psoriasis.
  • RI is alkyl, aryl, heteroaryl or aryl-alkyl with 1-4 carbon atoms group, heteroaryl- alkyl with 1-4 carbon atoms group, morpholino-alkyl with 1-4 carbon atoms group or dialkylamino-alkyl with 1-4 carbon atoms group.
  • R2, R3 independently of each other are hydrogen, methyl, ethyl, propyl, isopropyl or cyclopropyl groups or R2 and R3 together are tetramethylene group.
  • RIO is hydrogen or nitrile group
  • Rl l is hydrogen, methyl, ethyl, propyl, isopropyl, tert.- butyl group or tetramethylene ring connected to X
  • amines of aniline type are used the solvent is changed to a protic one advantageously methanol, ethanol or isopropanol and they are brought into reaction with malonic acid dinitrile using alkaline medium (aqueous solution of KOH or NaOH) in inert atmosphere.
  • alkaline medium aqueous solution of KOH or NaOH
  • the intermediate compound of general formula (II) is filtered having cooled the mixture then mixed with formic acid of 5 to 10 mass excess (of 85 to 98 mass %) at reflux temperature for 1 hour to 2 days.
  • the mixture is then poured onto icy water and the precipitated product is isolated either by filtering or extraction with ethyl acetate at neutral pH.
  • the version C) of the process is performed similarly but the hydrazine derivative is brought into reaction with isatin.
  • the NMR photos were taken by apparatus Bruker AC300.
  • the apparatus used for measurement of HPLC was:
  • the melting points were measured by the apparatus B ⁇ chi Melting Point B-540.
  • Example 2 40 g of 2-amino-4,5-dimemyl-l-(3-cUorophenyl)--mino-3-cyano-pyrrole (Example 1) was refluxed in 200 g of formic acid for 10 hours. The mixture was then poured onto ice and stirred for 1 hour. The precipitated material was filtered out and washed with water. The product was dried at room temperature and used in the following reaction without further purification. (27 g; 60 %).
  • the compound was produced as described in the Example 5 with the difference that the primary substance was the known intermediate product marked as im3_l (2.71 g of the substance).
  • Example 94 (Study of pharmaceutical effect) Examination of the in vivo neurogenic inflammation inhibiting effect.
  • the thickness of ears was measured again after 30 minutes and the swelling was defined as per cents of the initial thickness.
  • the animals were killed thereafter by bleeding to death, their ears were cut and the mass of the ears was measured.
  • the stain accumulated in the tissue pieces was extracted with 1.5 ml of formamide at 20 C° for 72 hours.
  • the optical densities of the solutions were determined by spectrophotometry (with microplate reader) at the wavelength of 620 nm.
  • the quantity of extravased stain (indicating the plasma albumin quantity) was defined in units of mg per humid tissue
  • the values measured in the ears treated in alcohol were subtracted from the ones measured in the ears treated with capsaicine at both animals.
  • the animals treated with solvent served as control.
  • the partial unilateral ligation of n. ishiadicus causes diminution of the mechanonociceptive threshold of the extremity (Seltzer's operation).
  • the mechanonociception was examined with Ugo Basile's analgesimeter (Randall- Selitto test).
  • the foot of the animal was put under a teflon cone with rounded end and gradually increasing force was exerted onto middle region of the beck of foot.
  • the pain threshold is the value when the animal pulls its leg out. It may be read out in grams by the hand moving before linear scale.
  • the change of the mechanical threshold was expressed in per cents of the own initial threshold.
  • the nervus ischiadus of the thigh of male Sprague-Dawley rats was prepared on the one side in pentobarbital narcosis after control measurements then 1/3 to 1/2 part of the nerves were carefully detached, tightly bound with non-traumatic thread

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/HU2005/000040 2004-04-29 2005-04-25 7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES, AS WELL AS THEIR THERAPEUTICALLY ACCEPTABLE SALTS, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND PROCESS FOR PRODUCTION THE ACTIVE AGENT Ceased WO2005105804A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CA002564277A CA2564277A1 (en) 2004-04-29 2005-04-25 7h-pyrrolo[2,3-d]pyrimidine derivatives, as well as their therapeutically acceptable salts, pharmaceutical preparations containing them and process for production the active agent
AT05739554T ATE462706T1 (de) 2004-04-29 2005-04-25 7h-pyrroloä2,3-düpyrimidinderivate sowie deren therapeutisch annehmbare salze, pharmazeutische zubereitungen, die diese enthalten, und verfahren zur herstellung des wirkstoffs
US11/587,851 US20080214583A1 (en) 2004-04-29 2005-04-25 7H-Pyrrolo[2,3-D]Pyrimidine Derivatives, As Well As Their Therapeutically Acceptable Salts, Pharmaceutical Preparations Containing Them And Process For Production The Active Agent
JP2007510131A JP2007534737A (ja) 2004-04-29 2005-04-25 ７Ｈ−ピロロ［２，３−ｄ］ピリミジン誘導体、ならびにその治療的に許容される塩、それらを含有する製薬調製物および活性剤を生成するプロセス
DE602005020281T DE602005020281D1 (de) 2004-04-29 2005-04-25 7H-PYRROLOÄ2,3-dÜPYRIMIDINDERIVATE SOWIE DEREN THERAPEUTISCH ANNEHMBARE SALZE, PHARMAZEUTISCHE ZUBEREITUNGEN, DIE DIESE ENTHALTEN, UND VERFAHREN ZUR HERSTELLUNG DES WIRKSTOFFS
AU2005238287A AU2005238287A1 (en) 2004-04-29 2005-04-25 7H-pyrrolo[2,3-d]pyrimidine derivatives, as well as their therapeutically acceptable salts, pharmaceutical preparations containing them and process for production the active agent
EP05739554A EP1756110B1 (en) 2004-04-29 2005-04-25 7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES, AS WELL AS THEIR THERAPEUTICALLY ACCEPTABLE SALTS, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND PROCESS FOR PRODUCTION THE ACTIVE AGENT
IL178906A IL178906A0 (en) 2004-04-29 2006-10-26 7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES, AS WELL AS THEIR THERAPEUTICALLY ACCEPTABLE SALTS, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND PROCESS FOR PRODUCTION THE ACTIVE AGENT

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU0400891A HUP0400891A2 (en) 2004-04-29 2004-04-29 7h-pyrrolo[2,3-d]pyrimidine derivatives, their pharmaceutically acceptable salts, pharmaceutical compositions containing them and process for the production of the compounds
HUP0400891 2004-04-29

Publications (1)

Publication Number Publication Date
WO2005105804A1 true WO2005105804A1 (en) 2005-11-10

Family

ID=89982174

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU2005/000040 Ceased WO2005105804A1 (en) 2004-04-29 2005-04-25 7H-PYRROLO[2,3-d]PYRIMIDINE DERIVATIVES, AS WELL AS THEIR THERAPEUTICALLY ACCEPTABLE SALTS, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND PROCESS FOR PRODUCTION THE ACTIVE AGENT

Country Status (13)

Country Link
US (1) US20080214583A1 (https=)
EP (1) EP1756110B1 (https=)
JP (1) JP2007534737A (https=)
KR (1) KR20070047737A (https=)
CN (1) CN1972946A (https=)
AT (1) ATE462706T1 (https=)
AU (1) AU2005238287A1 (https=)
CA (1) CA2564277A1 (https=)
DE (1) DE602005020281D1 (https=)
HU (1) HUP0400891A2 (https=)
IL (1) IL178906A0 (https=)
RU (1) RU2391344C2 (https=)
WO (1) WO2005105804A1 (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014145576A3 (en) * 2013-03-15 2014-12-18 Northwestern University Substituted pyrrolo(2,3-d)pyrimidines for the treatment of cancer
WO2016042349A1 (en) * 2014-09-17 2016-03-24 Pécsi Tudományegyetem New agents for treating neurogenic inflammation and neuropathic hyperalgesia related disorders

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150133426A1 (en) * 2012-05-21 2015-05-14 Bayer Pharma Aktiengesellschaft Substituted pyrrolopyrimidines
RU2603770C2 (ru) * 2014-11-28 2016-11-27 Федеральное государственное автономное образовательное учреждение высшего образования "Белгородский государственный национальный исследовательский университет" (НИУ "БелГУ") Замещенные пиразинопиримидиноны как блокаторы trpa1 каналов, фармацевтическая композиция, способы их получения и применения
CN110483526B (zh) * 2019-09-09 2021-10-01 辽宁大学 含芳基腙结构的吡唑并[1,5-a]嘧啶类衍生物及其应用
CN119613409B (zh) * 2024-12-05 2026-04-17 浙江工业大学 吡咯并[2,3-d]嘧啶衍生物及其在制备抗炎药物中的应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4229453A (en) * 1978-04-27 1980-10-21 Bayer Aktiengesellschaft Substituted 5,6-dimethylpyrrolo[2,3-d]pyrimidine compounds, their production and their medicinal use
EP1081149A1 (en) * 1998-05-19 2001-03-07 Otsuka Pharmaceutical Factory, Inc. PYRAZOLO 1,5-a]PYRIMIDINE DERIVATIVES
WO2001042246A2 (en) * 1999-12-10 2001-06-14 Pfizer Products Inc. PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS

Family Cites Families (2)

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RU2001111033A (ru) * 1998-09-18 2003-05-20 Басф Акциенгезелльшафт (De) Пирролопиримидины в качестве ингибиторов протеинкиназ
BRPI0514094A (pt) * 2004-08-02 2008-05-27 Osi Pharm Inc composto, composição, e, método de tratamento de distúrbio hiperproliferativo

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4229453A (en) * 1978-04-27 1980-10-21 Bayer Aktiengesellschaft Substituted 5,6-dimethylpyrrolo[2,3-d]pyrimidine compounds, their production and their medicinal use
EP1081149A1 (en) * 1998-05-19 2001-03-07 Otsuka Pharmaceutical Factory, Inc. PYRAZOLO 1,5-a]PYRIMIDINE DERIVATIVES
WO2001042246A2 (en) * 1999-12-10 2001-06-14 Pfizer Products Inc. PYRROLO[2,3-d]PYRIMIDINE COMPOUNDS

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
TRAXLER P M ET AL: "4-(PHENYLAMINO)PYRROLOPYRIMIDINES: POTENT AND SELECTIVE, ATP SITE DIRECTED INHIBITORS OF THE EGF-RECEPTOR PROTEIN TYROSINE KINASE", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 39, no. 12, December 1996 (1996-12-01), pages 2285 - 2292, XP002053503, ISSN: 0022-2623 *
W.M. BASYOUNI, H.M. HOSNI, K.A.M. EL-BAYOUKI: "Pyrrolo[2,3-d]pyrimidines. Part 3: Synthesis of some novel 4-substituted pyrrolo[2,3-d]pyrimidines and their related derivatives", JOURNAL OF CHEMICAL RESEARCH, MINIPRINT, vol. 12, 1997, pages 2771 - 2789, XP009054934 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014145576A3 (en) * 2013-03-15 2014-12-18 Northwestern University Substituted pyrrolo(2,3-d)pyrimidines for the treatment of cancer
US9981968B2 (en) 2013-03-15 2018-05-29 Northwestern University Substituted pyrrolo[2,3-d]pyrimidines for the treatment of cancer and proliferative disorders
WO2016042349A1 (en) * 2014-09-17 2016-03-24 Pécsi Tudományegyetem New agents for treating neurogenic inflammation and neuropathic hyperalgesia related disorders

Also Published As

Publication number Publication date
AU2005238287A1 (en) 2005-11-10
CA2564277A1 (en) 2005-11-10
HUP0400891A2 (en) 2006-04-28
US20080214583A1 (en) 2008-09-04
ATE462706T1 (de) 2010-04-15
EP1756110B1 (en) 2010-03-31
RU2391344C2 (ru) 2010-06-10
HU0400891D0 (en) 2004-07-28
EP1756110A1 (en) 2007-02-28
IL178906A0 (en) 2007-03-08
RU2006141393A (ru) 2008-06-10
CN1972946A (zh) 2007-05-30
JP2007534737A (ja) 2007-11-29
DE602005020281D1 (de) 2010-05-12
KR20070047737A (ko) 2007-05-07

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