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WO2002074742A3 - Cdk-inhibitory indirubin derivatives having an increased solubility - Google Patents

Cdk-inhibitory indirubin derivatives having an increased solubility Download PDF

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Publication number
WO2002074742A3
WO2002074742A3 PCT/EP2002/002983 EP0202983W WO02074742A3 WO 2002074742 A3 WO2002074742 A3 WO 2002074742A3 EP 0202983 W EP0202983 W EP 0202983W WO 02074742 A3 WO02074742 A3 WO 02074742A3
Authority
WO
WIPO (PCT)
Prior art keywords
diseases
disease
indirubin derivatives
increased solubility
production
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/EP2002/002983
Other languages
German (de)
French (fr)
Other versions
WO2002074742A2 (en
Inventor
Rolf Jautelat
Thomas Brumby
Olaf Prien
Martina Schaefer
Gerhard Siemeister
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.)
Bayer Pharma AG
Original Assignee
Schering AG
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 Schering AG filed Critical Schering AG
Priority to JP2002573751A priority Critical patent/JP2004519502A/en
Publication of WO2002074742A2 publication Critical patent/WO2002074742A2/en
Publication of WO2002074742A3 publication Critical patent/WO2002074742A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/36—Oxygen atoms in position 3, e.g. adrenochrome
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biotechnology (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Immunology (AREA)
  • Hematology (AREA)
  • Hospice & Palliative Care (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Urology & Nephrology (AREA)
  • Toxicology (AREA)
  • Dermatology (AREA)
  • Psychiatry (AREA)
  • Indole Compounds (AREA)

Abstract

The invention relates to indirubin derivatives, which maintain a radically increased solubility while preserving the biological activity at the same time by establishing a quaternary center in the R1 position. The invention also relates to the production of the indirubin derivatives, to their intermediate products for the production, and to their use as a medicament in the treatment of cancer such as solid tumors and leukemia, of autoimmune diseases such as psoriasis, alopecia and multiple sclerosis, of chemotherapeutic drug-induced alopecia and mucositis, of cardiovascular diseases such as stenoses, arterioscleroses and restenoses, of infectious diseases such as those caused by unicellular parasites such as Trypanosoma, Toxoplasma or Plasmodium or by fungi, of nephrological diseases such as glomerulonephritis, of chronic neurodegenerative diseases such as Huntington's disease, amyotrophic lateral sclerosis, Parkinson's disease, AIDS dementia, and Alzheimer's disease, of acute neurodegenerative diseases such as ischaemia of the brain and neurotrauma, of viral infections such as cytomegalic infections, herpes, hepatitis B and C, and of HIV diseases.
PCT/EP2002/002983 2001-03-16 2002-03-18 Cdk-inhibitory indirubin derivatives having an increased solubility Ceased WO2002074742A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2002573751A JP2004519502A (en) 2001-03-16 2002-03-18 CDK-inhibited indirubin derivatives with enhanced solubility

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10114138A DE10114138C2 (en) 2001-03-16 2001-03-16 Cdk-inhibitory Indirubin derivatives with increased solubility
DE10114138.6 2001-03-16

Publications (2)

Publication Number Publication Date
WO2002074742A2 WO2002074742A2 (en) 2002-09-26
WO2002074742A3 true WO2002074742A3 (en) 2003-02-20

Family

ID=7678630

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/002983 Ceased WO2002074742A2 (en) 2001-03-16 2002-03-18 Cdk-inhibitory indirubin derivatives having an increased solubility

Country Status (3)

Country Link
JP (1) JP2004519502A (en)
DE (1) DE10114138C2 (en)
WO (1) WO2002074742A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10129028A1 (en) * 2001-06-11 2003-01-02 Schering Ag Soluble Cdk-inhibitory Indirubin Derivatives
US7582670B2 (en) 2001-12-13 2009-09-01 Natrogen Therapeutics, Inc. Methods of treating an inflammatory-related disease
US20050154046A1 (en) * 2004-01-12 2005-07-14 Longgui Wang Methods of treating an inflammatory-related disease
US8563525B2 (en) 2004-01-12 2013-10-22 Natrogen Therapeutics International, Inc. Methods of treating an inflammatory-related disease
DE102004028899B4 (en) * 2004-06-09 2009-09-03 Technische Universität Dresden Use of a combination for the preventive and / or therapeutic treatment of bacterial infectious diseases or sepsis
US7781478B2 (en) 2004-07-14 2010-08-24 Ptc Therapeutics, Inc. Methods for treating hepatitis C
WO2006117212A2 (en) 2005-05-04 2006-11-09 Develogen Aktiengesellschaft Use of gsk-3 inhibitors for preventing and treating pancreatic autoimmune disorders
AR059066A1 (en) 2006-01-27 2008-03-12 Amgen Inc COMBINATIONS OF THE ANGIOPOYETINE INHIBITOR -2 (ANG2) AND THE VASCULAR ENDOTELIAL GROWTH FACTOR INHIBITOR (VEGF)
WO2008152014A2 (en) * 2007-06-12 2008-12-18 Boehringer Ingelheim International Gmbh 3-hetrocyclylidene-indolinone derivatives as inhibitors of specific cell cycle kinases
NZ584454A (en) 2007-10-12 2011-09-30 Ingenium Pharmaceuticals Gmbh N-[6-phenyl-pyrimidin-4-yl]-amides and urea derivatives as inhibitors of protein kinases
NZ627520A (en) 2010-03-10 2015-10-30 Astrazeneca Ab 4-phenyl pyridine analogues as protein kinase inhibitors
CN103391773A (en) 2010-09-27 2013-11-13 埃克塞里艾克西斯公司 Dual inhibitors of met and vegf for the treatment of castration resistant prostate cancer and osteoblastic bone metastases
EP3242934B1 (en) 2015-01-08 2021-08-18 The Board of Trustees of the Leland Stanford Junior University Factors and cells that provide for induction of bone, bone marrow, and cartilage
WO2024181799A1 (en) * 2023-02-28 2024-09-06 주식회사 씨케이리제온 Novel indoline derivative and use thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998007695A1 (en) * 1996-08-23 1998-02-26 Sugen, Inc. Indolinone combinatorial libraries and related products and methods for the treatment of disease
WO1999062503A2 (en) * 1998-05-29 1999-12-09 Cnrs (Centre National De Recherche Scientifique) France Innovation Scientifique Et Transfert Use of indigoid bisindole derivatives for the manufacture of a medicament to inhibit cyclin dependent kinases
WO2000061555A1 (en) * 1999-04-12 2000-10-19 Gerhard Eisenbrand Indigoid bisindole derivatives
WO2001037819A2 (en) * 1999-11-23 2001-05-31 Centre National De La Recherche Scientifique (C.N.R.S.) Use of indirubine derivatives for making medicines
WO2002034717A1 (en) * 2000-10-24 2002-05-02 Schering Aktiengesellschaft Sulphur-containing indirubin derivatives, production and use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0966963A1 (en) * 1998-05-29 1999-12-29 Gerhard Prof. Dr. Eisenbrand Use of indigoid bisindole derivatives as CDK1 inhibitors

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998007695A1 (en) * 1996-08-23 1998-02-26 Sugen, Inc. Indolinone combinatorial libraries and related products and methods for the treatment of disease
WO1999062503A2 (en) * 1998-05-29 1999-12-09 Cnrs (Centre National De Recherche Scientifique) France Innovation Scientifique Et Transfert Use of indigoid bisindole derivatives for the manufacture of a medicament to inhibit cyclin dependent kinases
WO2000061555A1 (en) * 1999-04-12 2000-10-19 Gerhard Eisenbrand Indigoid bisindole derivatives
WO2001037819A2 (en) * 1999-11-23 2001-05-31 Centre National De La Recherche Scientifique (C.N.R.S.) Use of indirubine derivatives for making medicines
WO2002034717A1 (en) * 2000-10-24 2002-05-02 Schering Aktiengesellschaft Sulphur-containing indirubin derivatives, production and use thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HOESSEL R ET AL: "INDIRUBIN, THE ACTIVE CONSTITUENT OF A CHINESE ANTILEUKAEMIA MEDICINE, INHIBITS CYCLIN-DEPENDENT KINASES", NATURE CELL BIOLOGY, MACMILLAN PUBLISHERS, GB, vol. 1, no. 1, 1 May 1999 (1999-05-01), pages 60 - 67, XP000856197, ISSN: 1465-7392 *

Also Published As

Publication number Publication date
JP2004519502A (en) 2004-07-02
DE10114138C2 (en) 2003-03-27
WO2002074742A2 (en) 2002-09-26
DE10114138A1 (en) 2002-10-02

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