DK2878594T3 - Difluormethylenforbindelse - Google Patents

Difluormethylenforbindelse Download PDF

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DK2878594T3
DK2878594T3 DK13823704.5T DK13823704T DK2878594T3 DK 2878594 T3 DK2878594 T3 DK 2878594T3 DK 13823704 T DK13823704 T DK 13823704T DK 2878594 T3 DK2878594 T3 DK 2878594T3
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compound
methyl
indazol
cyano
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Keita Nagai
Motoaki BABA
Shinichi Fujioka
Koh Nagasawa
Hirobumi Takahashi
Eri KONDOH
Sachie SOGO
Kenichi Tanaka
Yoshiki Itoh
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Sato Pharma
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    • 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
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    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
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    • A61P13/00—Drugs for disorders of the urinary system
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    • 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
    • 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
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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    • C07D401/00—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
    • 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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    • C07D401/14—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 three or more hetero rings
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    • C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D413/02—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
    • 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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Claims (19)

1. Forbindelse repræsenteret ved formlen (I) eller et farmaceutisk acceptabelt salt af forbindelsen: formlen (I): TKemisk formel 11
hvor R1 repræsenterer en gruppe repræsenteret ved den almene formel: -Q1-A1; Q1 repræsenterer en methylengruppe; A1 repræsenterer en arylgruppe eller en heteroarylgruppe eventuelt substitueret med 1 til 3 substituent(er) udvalgt blandt den følgende <substituentgruppe L> (hvor de tilstødende eventuelt to substituenter i arylgruppen eller heteroa-rylgruppen sammen kan danne en C-ι- til C6 alkylenedioxygruppe); R2 repræsenterer et hydrogenatom, en substituent udvalgt blandt den følgende <substituentgruppe M> eller en gruppe repræsenteret ved den almene formel: -Q2-A2; Q2 repræsenterer en enkeltbinding, en Ci- til C6-alkylengruppe eller C2- til C6-alkenylengruppe (hvor helheden af hver af 1 eller 2 eller flere methylen-gruppe(r), som udgør C1- til Ce-alkylengruppen, uafhængigt kan udskiftes med et oxygenatom, et nitrogenatom eller en carbonylgruppe, og/eller hydroge-net(erne), som udgør methylengruppen(rne), kan substitueres med et halogenatom, en cyanogruppe, en hydroxylgruppe eller en C1- til C6-alkylgruppe); A2 repræsenterer en cycloalkylgruppe, en alifatisk heterocyklusgruppe, en arylgruppe eller en heteroarylgruppe eventuelt substitueret med 1 til 3 substi-tuent(er) udvalgt blandt <substituentgruppe L> (hvor de tilstødende eventuelt to substituenter i arylgruppen eller heteroarylgruppen sammen kan danne en C1- til C6-alkylenedioxygruppe); W1, W2, W3 og W4 hver uafhængigt er et nitrogenatom eller en methingruppe eventuelt med substituent(er) udvalgt fra gruppen bestående af et halogenatom, en hydroxylgruppe, en cyanogruppe, en Ci- til C6-alkylgruppe, en cy-cloalkylgruppe, en halo-Ci- til C6-alkylgruppe, en Ci- til Ce-alkoxygruppe og en halo- Ci- til C6-alkoxygruppe; forudsat at 0 til 4 af W\ W2, W3 og W4 er nitro-genatom(er); X og Y hver især er en enkeltbinding; Z repræsenterer COOH; hvor <substituentgruppe L> og <substituentgruppe M> er defineret som følger: <substituentgruppe L>: et halogenatom, en hydroxylgruppe, en nitrogruppe, en cyanogruppe, en for-mylgruppe, en aminogruppe, en carboxylgruppe, en Ci- til C6- alkylgruppe, en halo-Ci- til C6-alkylgruppe, en cycloalkyl gruppe, en Ci- til C6- alkoxygruppe, en halo-Ci- til C6- alkoxygruppe, en hydroxy-Ci- til C6-alkylgruppe, en Ci- til Ce-alkoxy Ci- til C6- alkylgruppe, en C2- til Cz-alkoxycarbonylgruppe, en C2- til C7-alkanoylgruppe, en Ci- til C6-alkylthiogruppe, en Ci- til- C6-alkylsulfonyl-gruppe, en Ci- til C6-alkylaminogruppe, en di-Ci- til C6-alkylaminogruppe, en carbamoylgruppe, en mono- Ci- til Ce-alkylcarbamoylgruppe, en di-Ci- til Ce-alkylcarbamoylgruppe, en C2- til Ci3-alkanoylaminogruppe, en Ci- til Ci2-al-kylsulfonylaminogruppe, en C2- til Ci3-alkoxycarbonylaminogruppe, en aralkyl-gruppe, en aryloxygruppe, en heteroaryloxygruppe, en C2- til C6alkenylgruppe og en cyano- Ci- til Cealkylgruppe <substituentgruppe M>: et halogenatom, en hydroxylgruppe, en nitrogruppe, en cyanogruppe, en for-mylgruppe, en aminogruppe, en carboxylgruppe, en Ci- til C6-alkylgruppe, en halo-Ci- til C6-alkylgruppe, en cycloalkylgruppe, en Ci til C6- alkoxygruppe, en halo-Ci til C6-alkoxygruppe, en hydroxy-Ci- til C6-alkylgruppe, en Ci- til C6-alkoxy Ci- til C6-alkylgruppe, en C2 til Cz-alkoxy- carbonylgruppe, en C2- til C7-alkanoylgruppe, en Ci- til C6- alkylthio gruppe, en Ci- til C6- alkylsulfonyl-gruppe, en Ci- til C6- alkylaminogruppe, en di- Ci- til C6-alkylaminogruppe, en carbamoylgruppe, en mono- Ci- til Cealkylcarbamoylgruppe, en di- Ci- til C6-alkylcarbamoylgruppe, en C2- til Ci3-alkanoylaminogruppe, en Ci- til Ci2-al-kylsulfonylaminogruppe og en C2- til Ci3-alkoxycarbonylaminogruppe]; og bortset fra at formel (I) repræsenterer: [1-(2,6-dichlorbenzyl)-3-methyl-1H-indazol-6-yl]difluor-eddikesyre; kalium [1 -(2,6-dichlorbenzyl)-3-methyl-1 H-indazol-6-yl]difluoracetat; [1-(2-cyano-6-methylbenzyl)-3-methyl-1H-indol-6-yl]difluoreddikesyre; [1-(2-cyano-6-hydroxymethylbenzyl)-3-methyl-1H-indazol-6-yl]difluored- dikesyre; kalium [1 -(2-cyano-6-hydroxymethylbenzyl)-3-methyl-1 H-indazol-6-yl]difluo-racetat; [1-(2-cyano-6-methylbenzyl)-3-cyclopropyl-1H-indazol-6-yl]difluoreddikesyre; [1-(2-cyano-6-methylbenzyl)-3-isopropyl-1H-indazol-6-yl]difluoreddikesyre; [3-chlor-1-(2-cyano-6-methylbenzyl)-1 H-indazol-6-yl]difluoreddikesyre; [1-(2-cyano-6-methylbenzyl)-3-ethyl-1H-indazol-6-yl]difluoreddikesyre; [1-(2-cyano-6-methylbenzyl)-3-difluormethyl-1H-indazol-6-yl]difluored-dikesyre; og [1-(2-cyano-6-methylbenzyl)-3-hydroxymethyl-1H-indazol-6-yl]difluored- dikesyre.
2. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge krav 1, hvor R2 er et halogenatom, en cyanogruppe, en C-ι- til C6-alkylgruppe, en halo-Ci- til C6-alkylgruppe, en cycloalkylgruppe eller en hydroxy-Ci- til C6-al-kylgruppe.
3. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge et af kravene 1 til 2, hvor A1 er en eventuelt substitueret phenylgruppe, en eventuelt substitueret naphthylgruppe, en eventuelt substitueret quinolylgruppe, en eventuelt substitueret isoquinolylgruppe, en eventuelt substitueret isoindolyl-gruppe eller en eventuelt substitueret benzothienylgruppe.
4. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge et af kravene 1 til 3, hvor R2 er en methylgruppe, en ethylgruppe, en trifluormethyl-gruppe, en hydroxymethylgruppe eller et chlorinatom.
5. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge et af kravene 1 til 4, hvor W1 er et nitrogenatom.
6. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge et af kravene 1 til 5, hvor W2, W3 og W4 hver især er en gruppe repræsenteret ved den almene formel:=CH-.
7. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge krav 1, som er [1-(2-chlor-6-fluorbenzyl)-3-methyl-1H-indazol-6-yl]difluoreddike-syre.
8. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge krav 1, som er [1-(2,3-dichlorbenzyl)-3-methyl-1FI-indazol-6-yl]difluoreddikesyre.
9. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge krav 1, som er difluor[1-(2-fluor-6-trifluormethylbenzyl)-3-methyl-1FI-indazol-6-yl]eddikesyre.
10. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge krav 1, som er [1-(2-cyano-6-methylbenzyl)-3-methyl-1FI-indazol-6-yl]difluo-reddikesyre.
11. Forbindelse eller et farmaceutisk acceptabelt salt af forbindelsen ifølge krav 1, som er [1-(2-cyano-6-cyclopropylbenzyl)-3-methyl-1FI-indazol-6-yl]difluoreddikesyre.
12. URAT 1 -inhibitor omfattende forbindelsen eller et farmaceutisk acceptabelt salt af forbindelsen ifølge et af de foregående krav.
13. Blodurinsyre-niveausænkende middel omfattende forbindelsen eller et farmaceutisk acceptabelt salt af forbindelsen ifølge et af kravene 1 til 11.
14. Farmaceutisk sammensætning til anvendelse inden for behandlingen eller forebyggelsen af en patologisk tilstand associeret med blodurinsyre, omfattende forbindelsen eller et farmaceutisk acceptabelt salt af forbindelsen ifølge et af kravene 1 til 11 og et farmaceutisk acceptabelt bærestof.
15. Farmaceutisk sammensætning til anvendelse ifølge krav 14, hvor den patologiske tilstand associeret med blodurinsyre er udvalgt fra gruppen bestående af hyperurikæmi, gigtknude, akut gigtarthritis, kronisk gigtarthritis, gigtnyre, urolithiasis, en forstyrrelse i nyrefunktionn, koronare ateriesygdomme og iskæmiske hjertesygdomme.
16. Farmaceutisk sammensætning til anvendelse ifølge krav 14, hvor den patologiske tilstand, som er associeret med blodurinsyre, er hyperurikæmi.
17. Forbindelse ifølge et af kravene 1 til 11, til anvendelse som et medikament.
18. Forbindelse ifølge et af kravene 1 til 11 til anvendelse inden for behandlingen afen patologisk tilstand associeret med blodurinsyre.
19. Forbindelse ifølge et af kravene 1 til 11 til anvendelse inden for behandlingen af hyperurikæmi, gigtknude, akut gigtarthritis, kronisk gigtarthritis, gigtnyre, urolithiasis, en forstyrrelse i nyrefunktionen, koronare ateriesygdomme eller iskæmiske hjertesygdomme.
DK13823704.5T 2012-07-27 2013-07-26 Difluormethylenforbindelse DK2878594T3 (da)

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