DK2348016T3 - Phenylpyrrolaminoguanidinderivater - Google Patents

Phenylpyrrolaminoguanidinderivater Download PDF

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DK2348016T3
DK2348016T3 DK11164583.4T DK11164583T DK2348016T3 DK 2348016 T3 DK2348016 T3 DK 2348016T3 DK 11164583 T DK11164583 T DK 11164583T DK 2348016 T3 DK2348016 T3 DK 2348016T3
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optionally substituted
compound
alkyl
amino
mono
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DK11164583.4T
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Arne Boman
Thomas Engelbrecht Norkild Jonassen
Torbjörn Lundstedt
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Synact Pharma Aps
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/42—Nitro radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms

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Claims (15)

  1. Phenylpyrrolaminoguanidinderivater
    1. Forbindelse med den almene formel (I)
    (i) inkluderende tautomere former deraf, hvor n er 1, 2 eller 3; hver Ri, R2, R3, R4 og Rs er uafhængigt valgt fra gruppen bestående af hydrogen, eventuelt substitueret Ci-e-alkyl, eventuelt substitueret C3-6-cycloalkyl, eventuelt substitueret C2-e-alkenyl, eventuelt substitueret C4-e-alkadienyl, eventuelt substitueret C2-e-alkynyl, hydroxy, eventuelt substitueret Ci-6-alkoxy, eventuelt substitueret C2-e-alkenyloxy, carboxy, eventuelt substitueret Ci-6-alkoxycarbonyl, eventuelt substitueret Ci-6-alkylcarbonyl, formyl, Ci-e-alkylsulfonylamino, eventuelt substitueret aryl, eventuelt substitueret aryloxycarbonyl, eventuelt substitueret aryloxy, eventuelt substitueret arylcarbonyl, eventuelt substitueret arylamino, arylsulfonylamino, eventuelt substitueret heteroaryl, eventuelt substitueret heteroaryloxycarbonyl, eventuelt substitueret heteroaryloxy, eventuelt substitueret heteroarylcarbonyl, eventuelt substitueret heteroarylamino, heteroarylsulfonylamino, eventuelt substitueret heterocyclyl, eventuelt substitueret heterocyclyloxycarbonyl, eventuelt substitueret heterocyclyloxy, eventuelt substitueret heterocyclylcarbonyl, eventuelt substitueret heterocyclylamino, heterocyclylsulfonylamino, amino, mono- og di(Ci-e-alkyl)amino, carbamoyl, mono- og di(Ci-6-alkyl)aminocarbonyl, amino-Ci-e-alkyl-aminocarbonyl, mono- og di(Ci-6-alkyl)amino-Ci-6-alkyl-aminocarbonyl, Ci-e- alkylcarbonylamino, amino-Ci-6-alkylcarbonylamino, mono- og di(Ci-6-alkyl)amino-Ci-6-alkyl-carbonylamino, cyano, guanidino, carbamido, Ci-6-alkanoyloxy, Ci-6-alkylsulfonyl, Ci-e-alkylsulphinyl, Ci-6-alkylsulfonyloxy, aminosulfonyl, mono- og di(Ci-6-alkyl)aminosulfonyl, nitro, eventuelt substitueret Ci-6-alkylthio og halogen, hvor en hvilken som helst nitrogenbundet Ci-6-alkyl eventuelt er substitueret med hydroxy, Ci-e-alkoxy, C2-e-alkenyloxy, amino, mono- og di(Ci-6-alkyl)amino, carboxy, Ci-e-alkylcarbonylamino, halogen, Ci-6-alkylthio, Ci-e-alkyl-sulfonyl-amino eller guanidin; hver R6 og R7 er uafhængigt valgt fra gruppen bestående af hydrogen, eventuelt substitueret Ci-6-alkyl, eventuelt substitueret C2-6-alkenyl, eventuelt substitueret C4-6-alkadienyl, eventuelt substitueret C2-e-alkynyl, eventuelt substitueret C1-6-alkoxycarbonyl, eventuelt substitueret Ci-e-alkylcarbonyl, eventuelt substitueret aryl, eventuelt substitueret aryloxycarbonyl, eventuelt substitueret arylcarbonyl, eventuelt substitueret heteroaryl, eventuelt substitueret heteroaryloxycarbonyl, eventuelt substitueret heteroarylcarbonyl, aminocarbonyl, mono- og di(Ci-6-alkyl)aminocarbonyl, amino-Ci-6-alkyl-aminocarbonyl og mono- og di(Ci-6-alkyl)amino-Ci-6-alkyl-aminocarbonyl; eller R6 og R7 sammen kan danne en fem-eller seks-leddet nitrogen-indeholdende ring; eller et farmaceutisk acceptabelt salt deraf.
  2. 2. Forbindelsen ifølge krav 1, hvor hver Ri, R2, R3, R4 og R5 er uafhængigt valgt fra gruppen bestående af hydrogen, eventuelt substitueret Ci-e-alkyl, eventuelt substitueret C2-6-alkenyl, eventuelt substitueret C2-6-alkynyl, hydroxy, eventuelt substitueret Ci-e-alkoxy, eventuelt substitueret C2-6-alkenyloxy, carboxy, eventuelt substitueret Ci-6-alkoxycarbonyl, eventuelt substitueret Ci-e-alkylcarbonyl, formyl, amino, mono- og di(Ci-6-alkyl)amino, carbamoyl, mono- og di(Ci-6-alkyl)aminocarbonyl, amino-Ci-e-alkylaminocarbonyl, mono- og di(Ci-e-alkyl)amino-Ci-6-alkyl-aminocarbonyl, Ci-e-alkylcarbonylamino, amino-Ci-e-alkyl-carbonylamino, mono- og di(Ci-6-alkyl)amino-Ci-6-alkylcarbonylamino, cyano, carbamido, Ci-6-alkanoyloxy, Ci-e-alkylsulfonyl, Ci-e-alkylsulphinyl, Ci-e-alkylsulfonyloxy, aminosulfonyl, mono- og di(Ci-6-alkyl)aminosulfonyl, nitro, eventuelt substitueret Ci-6-alkylthio og halogen.
  3. 3. Forbindelsen ifølge krav 2, hvor hver Ri, R2, R3, R4 og R5 er uafhængigt valgt fra gruppen bestående af hydrogen, eventuelt substitueret Ci-e-alkyl, eventuelt substitueret C2-6-alkenyl, hydroxy, eventuelt substitueret Ci-e-alkoxy, amino, cyano, nitro og halogen.
  4. 4. Forbindelsen ifølge et hvilket som helst af kravene 1-3, hvor Re og R7 begge er hydrogen.
  5. 5. Forbindelsen ifølge et hvilket som helst af kravene 1-4, hvor Ri, R2, R4 og Rs er hydrogen og R3 er som defineret i et hvilket som helst af kravene 1-3.
  6. 6. Forbindelsen ifølge krav 5, hvor R3 er er placeret i 2-positionen.
  7. 7. Forbindelsen ifølge krav 5, hvor R3 er placeret i 4-positionen.
  8. 8. Forbindelsen ifølge et hvilket som helst af kravene 1-7, hvor forbindelsen har strukturen vist i den almene formel (la)
    (la) og hvor n, Ri, R2, R3, R4, R5, Re og R7 er som defineret i et hvilket som helst af kravene 1-7.
  9. 9. Forbindelsen ifølge et hvilket som helst af kravene 1-8, hvor n er 1.
  10. 10. Farmaceutisk sammensætning omfattende en forbindelse som defineret i et hvilket som helst af kravene 1-9 og en farmaceutisk acceptabel bærer eller excipiens.
  11. 11. Forbindelse som defineret i et hvilket som helst af kravene 1-9 til anvendelse som medikament.
  12. 12. Forbindelse som defineret i et hvilket som helst af kravene 1-9 til anvendelse i behandlingen af fedme.
  13. 13. Forbindelse som defineret i et hvilket som helst af kravene 1-9 til anvendelse i behandlingen af insulin-resistens.
  14. 14. Forbindelse som defineret i et hvilket som helst af kravene 1-9 til fremstillingen af et medikament til behandlingen af diabetes mellitus.
  15. 15. Forbindelse som defineret i et hvilket som helst af kravene 1-9 til anvendelse i behandlingen afen inflammatorisk tilstand.
DK11164583.4T 2006-06-09 2007-06-11 Phenylpyrrolaminoguanidinderivater DK2348016T3 (da)

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EP07730054A EP2035373B1 (en) 2006-06-09 2007-06-11 Phenyl pyrrole aminoguanidine derivatives

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EP (2) EP2348016B1 (da)
JP (1) JP5444523B2 (da)
CN (1) CN101466669B (da)
AT (1) ATE508111T1 (da)
AU (1) AU2007255366B2 (da)
CA (1) CA2688485C (da)
CY (1) CY1117851T1 (da)
DE (1) DE602007014363D1 (da)
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ES (1) ES2571253T3 (da)
HU (1) HUE029016T2 (da)
MX (1) MX2008015454A (da)
NZ (1) NZ573457A (da)
PL (1) PL2348016T3 (da)
SI (1) SI2348016T1 (da)
WO (1) WO2007141343A1 (da)
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EP2025674A1 (de) 2007-08-15 2009-02-18 sanofi-aventis Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
WO2009071101A1 (en) * 2007-12-07 2009-06-11 Action Pharma A/S N-modified aminoguanidine derivatives
WO2009074157A1 (en) * 2007-12-13 2009-06-18 Action Pharma A/S Fully-modified phenyl pyrrole aminoguanidines
UA99555C2 (en) 2008-11-12 2012-08-27 Элджи Лайф Саенсез Лтд. Melanocortin receptor agonists
CN112292125B (zh) * 2018-06-22 2023-10-31 西奈克制药有限公司 蛋白尿的治疗
LT3773558T (lt) 2019-05-10 2022-09-12 Synact Pharma Aps Kompleksinis artrito gydymas
CN120617247A (zh) * 2020-03-31 2025-09-12 西奈克制药有限公司 症状性病毒性疾病的治疗
EP4359076B1 (en) 2021-06-21 2025-08-06 SynAct Pharma ApS Phenyl pyrrole aminoguanidine salts and formulations
WO2023218048A1 (en) 2022-05-12 2023-11-16 Synact Pharma Aps Resomelagon and its derivatives for the treatment of cardiovascular disease, hypertension and atherosclerosis
CN120584099A (zh) * 2022-12-21 2025-09-02 西奈克制药有限公司 苯基吡咯肼甲脒化合物的多晶型物

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ZA200810347B (en) 2010-05-26
US20110082183A1 (en) 2011-04-07
CA2688485C (en) 2016-01-05
EP2035373B1 (en) 2011-05-04
EP2348016A1 (en) 2011-07-27
JP2009539809A (ja) 2009-11-19
HK1160136A1 (en) 2012-08-10
AU2007255366A1 (en) 2007-12-13
NZ573457A (en) 2011-06-30
AU2007255366B2 (en) 2013-07-18
US8058306B2 (en) 2011-11-15
MX2008015454A (es) 2009-01-30
WO2007141343A1 (en) 2007-12-13
DE602007014363D1 (de) 2011-06-16
JP5444523B2 (ja) 2014-03-19
CA2688485A1 (en) 2007-12-13
CY1117851T1 (el) 2017-05-17
ES2571253T3 (es) 2016-05-24
CN101466669B (zh) 2011-11-30
ATE508111T1 (de) 2011-05-15
HUE029016T2 (en) 2017-02-28
SI2348016T1 (sl) 2016-10-28
EP2035373A1 (en) 2009-03-18
PL2348016T3 (pl) 2016-09-30
CN101466669A (zh) 2009-06-24

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