DK2669270T3 - Indol-relaterede forbindelser som URAT1-hæmmere - Google Patents

Indol-relaterede forbindelser som URAT1-hæmmere Download PDF

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DK2669270T3
DK2669270T3 DK12739424.5T DK12739424T DK2669270T3 DK 2669270 T3 DK2669270 T3 DK 2669270T3 DK 12739424 T DK12739424 T DK 12739424T DK 2669270 T3 DK2669270 T3 DK 2669270T3
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synthesis
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Keita Nagai
Koh Nagasawa
Hirobumi Takahashi
Motoaki BABA
Shinichi Fujioka
Eri KONDOH
Kenichi Tanaka
Yoshiki Itoh
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Sato Pharma
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    • 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
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    • 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
    • A61P13/04—Drugs for disorders of the urinary system for urolithiasis
    • 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
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    • 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
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • A—HUMAN NECESSITIES
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    • 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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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    • 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
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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    • C07D209/04—Indoles; Hydrogenated indoles
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    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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  • Indole Compounds (AREA)

Claims (20)

1. Forbindelse repræsenteret ved Formel (I):
(I) [i formlen, R1 betegner en gruppe repræsenteret ved den almene formel: -Q1-A1; Q1 betegner en CrC6-alkylengruppe; A1 betegner en phenylgruppe, som er substitueret med en til tre substituenter udvalgt fra <Substituentgruppe L> beskrevet senere, naphthylgruppe eller en heteroarylgruppe, udvalgt blandt en pyridylgruppe, en quinolylgruppe, en thi-enylgruppe, en pyrazolylgruppe, en thiazolylgruppe, en isoxazolylgruppe eller en benzothienylgruppe, som kan være substitueret med en til tre substituenter udvalgt fra <Substituentgruppe L> beskrevet senere (heri kan hvilke som helst to substituenter grænsende op til hinanden på arylgruppen eller hete-roarylgruppen forbinde sig med hinanden for at danne en CrC6-alkylen-dioxygruppe); —- betegner en dobbeltbinding eller en enkeltbinding; når — er en dobbeltbinding, W1 betegner et nitrogenatom eller en gruppe repræsenteret ved den almene formel: =C(Ra)-, og W2 betegner en gruppe repræsenteret ved den almene formel: =C(Rb)-; når ™ er en enkeltbinding, W1 betegner en gruppe repræsenteret ved den almene formel: -C(Raa)(Rab)-, og W2 betegner en gruppe repræsenteret ved den almene formel: -C(Rba)(Rbb)-,; Ra og Rb betegner hver især uafhængigt et hydrogenatom, eller en substituent udvalgt fra <Substituentgruppe M> beskrevet senere; Raa og Rab betegner et hydrogenatom,; Rba og Rbb betegner hver især uafhængigt et hydrogenatom eller en substituent udvalgt fra <Substituentgruppe N> W3, W4 og W5 betegner hver især uafhængigt et nitrogenatom, eller en methingruppe; forudsat at nul til fire af W1, W2, W3, W4 og W5 er nitrogenatomer; X betegner en enkeltbinding, et oxygenatom, en carbonylgruppe eller en C2-C6-alkenylengruppe; Y er en enkeltbinding eller (CRYlRYl )n (heri er n et hvilket som helst helt tal fra 1 til 3, i er et hvilket som helst helt tal fra 1 til n, og (CRYlRYl)n betegner (CRY1RY1) når n = 1; betegner (CWY1RY1')-(CRY2RY2) når n = 2; betegner (CRY1RYr)-(CRY2RY2')-(CRY3RY3') når n = 3; heri er RY1, RYr, RY2, RY2', RY3 og RY3', er hver især uafhængigt et hydrogenatom, eller en substituent udvalgt fra <Substituentgruppe N>, Z betegner CONR3R4, S03 R2, en 5-tetrazolylgruppe, en 2-oxo-1,3,4-oxadiazolylgruppe eller en 2-thioxo-1,3,4-oxadiazolylgruppe; hvor, R2, R3 og R4 betegner et hydrogenatom, <Substituentgruppe L>: et halogenatom, en cyanogruppe, en CrC6-alkylgruppe og en cycloalkyl-gruppe, <Substituentgruppe M>: et halogenatom, en CrC6-alkylgruppe og en cycloalkylgruppe, <Substituentgruppe N>: en hydroxylgruppe og en CrC6-alkylgruppe, eller et farmaceutisk acceptabelt salt af forbindelsen.
2. Forbindelse ifølge krav 1, hvor understrukturen beskrevet nedenfor:
er udvalgt blandt følgende:
eller et farmaceutisk acceptabelt salt af forbindelsen.
3. Forbindelse ifølge krav 2, hvor X er en enkeltbinding, et oxygenatom, en carbonylgruppe eller en vinylengruppe, eller et farmaceutisk acceptabelt salt af forbindelsen.
4. Forbindelse ifølge krav 3, hvor Q1 er en methylengruppe, eller et farmaceutisk acceptabelt salt af forbindelsen.
5. Forbindelse ifølge krav 4, hvor arylgruppen eller heteroarylgruppen af A1 er en phenylgruppe, en naphthyl-gruppe, en quinolylgruppe eller en benzothienylgruppe, eller et farmaceutisk acceptabelt salt af forbindelsen.
6. Forbindelse ifølge krav 5, hvor <Substituentgruppe L> er gruppen bestående af et halogenatom, en cyano-gruppe, en methylgruppe og en cyclopropylgruppe, eller et farmaceutisk acceptabelt salt af forbindelsen.
7. Forbindelse ifølge krav 1, eller et farmaceutisk acceptabelt salt af forbindelsen, hvor forbindelsen er en hvilken som helst af de følgende: (I) 1 -(2,6-dichlorbenzyl)-3-methyl-6-(1 FI-tetrazol-5-ylmethyl)-1 Fl-indazol, (η) 1 -(2-chlor-6-methylbenzyl)-3-methyl-6-(1 H-tetrazol-5-yl)-1 H-pyrazolo[4,3-b]pyridin, (o) 1 -(2-chlor-6-cyclopropylbenzyl)-3-methyl-6-(1 H-tetrazol-5-yl)-1 H-pyrazo- lo[4,3-b]pyridin, (r) 3-chlor-1 -(2-chlor-6-methylbenzyl)-6-(1 H-tetrazol-5-yl)-1 H-pyrazolo[4,3-b]pyridin.
8. Forbindelse ifølge krav 1, som er 1 -(2,6-dichlorbenzyl)-3-methyl-6-(1 H-tetrazol-5-ylmethyl)-1 H-indazol, eller et farmaceutisk acceptabelt salt af forbindelsen.
9. Forbindelse ifølge krav 1, som er 1 -(2-chlor-6-methylbenzyl)-3-methyl-6-(1 H-tetrazol-5-yl)-1 FI-pyrazolo[4,3-b]pyridin, eller et farmaceutisk acceptabelt salt af forbindelsen.
10. Forbindelse ifølge krav 1, som er 1 -(2-chlor-6-cyclopropylbenzyl)-3-methyl-6-(1 H-tetrazol-5-yl)-1 H-pyrazolo[4,3-b]pyridin, eller et farmaceutisk acceptabelt salt af forbindelsen.
11. Forbindelse ifølge krav 1, som er 3-chlor-1 -(2-chlor-6-methylbenzyl)-6-(1 H-tetrazol-5-yl)-1 FI-pyrazolo[4,3-b]pyridin, eller et farmaceutisk acceptabelt salt af forbindelsen.
12. Forbindelse ifølge krav 1, som er 1 -(2,3-dichlorbenzyl)-3-methyl-6-(1 H-tetrazol-5-yl)-1 FI-pyrazolo[4,3-b]pyridin, eller et farmaceutisk acceptabelt salt af forbindelsen.
13. Forbindelse ifølge krav 1, som er 1 -(2,6-dichlorbenzyl)-3-ethyl-6-(1 H-tetrazol-5-yl)-1 FI-pyrazolo[4,3-b]pyridin, eller et farmaceutisk acceptabelt salt af forbindelsen.
14. Forbindelse ifølge krav 1, som er 3-chlor-1 -(2,6-dichlorbenzyl)-6-(1 H-tetrazol-5-yl)-1 FI-pyrazolo[4,3-b]pyridin, eller et farmaceutisk acceptabelt salt af forbindelsen.
15. Forbindelse ifølge et af kravene 1 til 14 eller et farmaceutisk acceptabelt salt af forbindelsen til anvendelse ved behandling af patologiske tilstande associeret med urinsyre i blodet.
16. Forbindelse ifølge et af kravene 1 til 14 eller et farmaceutisk acceptabelt salt deraf til anvendelse ifølge krav 15, hvor den patologiske tilstand associeret med urinsyre i blodet er udvalgt fra gruppen bestående af hyperurikæmi, gigtknude, akut gigtarthritis, kronisk gigtarthritis, gigtnyre, urolithiasis, en lidelse i nyrefunktionen, en koronar ateriesygdom og en iskæmisk hjertesygdom.
17. Forbindelse ifølge et af kravene 1 til 14 eller et farmaceutisk acceptabelt salt deraf til anvendelse ifølge krav 15, hvor den patologiske tilstand associeret med urinsyre i blodet er hyperurikæmi.
18. Farmaceutisk sammensætning til anvendelse ved behandling eller forebyggelse af patologiske tilstande associeret med urinsyre i blodet omfattende forbindelsen ifølge et af kravene 1 til 14 eller et farmaceutisk acceptabelt salt af forbindelsen og en farmaceutisk acceptabel bærer.
19. Farmaceutisk sammensætning til anvendelse ifølge krav 18, hvor den patologiske tilstand associeret med urinsyre i blodet er udvalgt fra gruppen bestående af hyperurikæmi, gigtknude, akut gigtarthritis, kronisk gigtarthritis, gigtnyre, urolithiasis, en lidelse i nyrefunktionen, en koronar ateriesygdom og en iskæmisk hjertesygdom.
20. Farmaceutisk sammensætning ifølge krav 18, hvor den patologiske tilstand associeret med urinsyre i blodet er hyperurikæmi.
DK12739424.5T 2011-01-28 2012-01-30 Indol-relaterede forbindelser som URAT1-hæmmere DK2669270T3 (da)

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WO (1) WO2012102405A1 (da)

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