DK1882684T3 - Pyrrolidinderivat eller salt deraf - Google Patents

Pyrrolidinderivat eller salt deraf Download PDF

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DK1882684T3
DK1882684T3 DK06746579.9T DK06746579T DK1882684T3 DK 1882684 T3 DK1882684 T3 DK 1882684T3 DK 06746579 T DK06746579 T DK 06746579T DK 1882684 T3 DK1882684 T3 DK 1882684T3
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methyl
ethyl
naphthyl
group
amino
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DK06746579.9T
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Shunichiro Hachiya
Makoto Oku
Takashi Shin
Keisuke Matsuura
Ryushi Seo
Takashi Kamikubo
Yoh Terada
Masanao Sanagi
Kousei Yoshihara
Taisuke Takahashi
Misawa Hana Mukai
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Astellas Pharma Inc
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Claims (11)

1. Pyrrolidinderivat som vist med den almene formel (I) eller et farmaceutisk acceptabelt salt deraf
CD hvilke tegn i formlen har de følgende betydninger: A og B: hver uafhængigt -C(R7)(R7a)- eller -C(O)-, R7 og R7a: hver uafhængigt -H, Ci-5 alkyl, aryl eller -C(O)OR0; R°: -H eller Ci-6 alkyl; X: enkeltbinding, *-0(0)-, *-0C(0)-, *-N(R8)C(0)- eller *-S(0)n-, hvor * betegner binding til R1; R8: -H eller Ci-6 alkyl, η: O, 1 eller 2, R1: -H, eller C1-12 alkyl, C2-6 alkenyl, aryl, heteroringgruppe eller cycloalkyl, hvor C1-12 alkyl og C2-6 alkenyl kan være substitueret med en gruppe valgt fra følgende gruppe G eller gruppe Ga; hvor aryl- og heteroringgruppen kan være substitueret med en gruppe valgt fra følgende gruppe P; hvor cycloalkylgruppen kan være substitueret med en gruppe valgt fra følgende gruppe Q; gruppe P: halogen, nitro, cyano, Ci-e alkyl, halogeno Ci-6 alkyl, -C(OH)(halogeno Οι-e alkyl)2, Ci-6 alkylen-C(0)0R°, C2-6 alkenylen-C(0)0R°, Ci-6 alkylen-C(0)N(R°)2, -Ο-Ci-e alkylen - C(0)0R°, -O-C1-6 alkylen-C(0)N(R°)2, -0R°, -O-halogeno Ci-6 alkyl, -N(R°)2, -NR°-C(0)R°, -C(0)-R°, -C(0)0R°, -C(0)N(R°)2, -C(0)NR°-Ci-6 alkylen-C(0)0R°, -C(O)NR0-Ci-6alkylen-C(O)N(R0)2, -C(O)NR0-S(O)2-Ci-6 alkyl, aryl, Ci-6 alkylen-aryl, -O-aryl, -S(0)2NH2, -S(0)n-aryl og heteroringgruppe, hvor arylgruppen og heteroringgruppen respektivt kan være substitueret med en gruppe valgt fra følgende gruppe Pa; gruppe Pa: halogen, nitro, cyano, Ci-β alkyl, halogeno Ci-β alkyl, -OR0, -O-halogeno Ci-6 alkyl, oxo, -C(O)OR0 og -C(0)N(R°)2 ; gruppe Q: Ci-e alkyl, -OR0, -O-halogeno Ci-5 alkyl, oxo, -C(O)-OR0, - C(0)N(R°)2-, -N(R°)2, -NR0 -C(0)R°, -NR0- Ci-β alkylen-C(O)OR0, -NR0- Ci-5 alkylen-C(0)N(R°)2, aryl og heteroringgruppe, hvor arylgruppen og heteroringgruppen respektivt kan være substitueret med en gruppe valgt fra den førnævnte gruppe Pa; gruppe G: halogen, oxo, -OR0, -O-halogeno Ci-6 alkyl, -N(R°)2, -NR°-C(0)R°, -C(O)OR0, -C(0)N(R°)2, -C(0)N(R8) - Ci-β alkylen-C(O)OR0, -C(0)NR°- Ci-6 alkylen-C(0)N(R°)2, cycloalkyl, aryl og heteroringgruppe, hvor cycloalkylgruppen kan være substitueret med en gruppe valgt fra gruppen Q og arylgruppen og heteroringgruppen respektivt kan være substitueret med en gruppe valgt fra gruppen P; gruppe Ga: -O-aryl, -S(0)n-aryl, -C(0)-aryl, -NR°-C(0)-aryl, -C(0)NR°-aryl, -C(0)NR°-(Ci-6 alkylen der kan være substitueret med -C(O)OR0)-aryl, -C(0)NR°-hetero ring gruppe, hvor arylgruppen og heteroringgruppen respektivt kan være substitueret med en gruppe valgt fra den førnævnte gruppe Pa; R2 og R3: hver uafhængigt -H, Ci-β alkyl, halogeno Ci-β alkyl, -OC(O)-R0, cycloalkyl, Ci-6 alkylen-cycloalkyl, aryl, Ci-6 alkylen-aryl, heteroringgruppe eller Ci-6 alkylen-heteroringgruppe, hvor aryl- og heteroringgruppen i R2 og R3 kan respektivt være substitueret med en gruppe valgt fra den førnævnte gruppe Pa, eller R2 og R3 i kombination kan danne en cycloalkylring eller heteroring, der respektivt kan være substitueret med en gruppe valgt fra den førnævnte gruppe Pa, sammen med carbonatomet til hvilket de er bundet; R4: en aryl- eller heteroarylringgruppe, der respektivt kan være substitueret med en gruppe valgt fra halogen, nitro, cyano, Ci-6 alkyl, halogeno Ci-6 alkyl, -OR0, -0-halogeno Ci-e alkyl, oxo, -C(0)0R°, -C(0)N(R°)2 eller -O-aryl; R5: Ci-6 alkyl eller halogeno Ci-6 alkyl; og R6: -H, Ci-6 alkyl eller halogeno Ci-6 alkyl, med det forbehold at når R4 er usubstitueret phenyl, er mindst én af R2 og R3 ikke -H, hvor cycloalkyl betegner C3-12 cycloalkyl, aryl betegner en Ce-14 monocyklisk til tricyklisk aryl, og heteroring betegner en mættet, umættet eller delvist umættet 4- til 8-leddet monocyklisk heteroring, 8- til 14-leddet bicycloheteroring eller 11- til 20-leddet tricyklisk heteroring der har 1 til 4 heteroatomer valgt fra O, S og N.
2. Forbindelsen eller et farmaceutisk acceptabelt salt deraf beskrevet i krav 1, hvor A og B er -CH2-, R1-/- er HO2C- C1-6 alkylen -OC(O)-; HO2C- C1-6 alkylen -C(O)-; (cycloalkyl substitueret med -C02H)-0C(0)-; (cycloalkyl substitueret med -C02H)-C(0)-; phenyl som er substitueret med -CO2H og yderligere kan være substitueret med en gruppe valgt fra gruppen bestående af halogen, halogeno Ci-6 alkyl og -O- C1-6 alkyl; (phenyl som er substitueret med -CO2H og yderligere kan være substitueret med en gruppe valgt fra gruppen bestående af halogen, halogeno C1-6 alkyl og -O- C1-6 alkyl)-OC(O)-; eller (phenyl som er substitueret med -C02H og yderligere kan være substitueret med en gruppe valgt fra bestående af halogen, halogeno C1-6 alkyl og -O- C1-6 alkyl) -NHC(O)-, R2 er phenyl der kan være substitueret med en gruppe valgt fra bestående af halogen, C1-6 alkyl og halogeno Ci-e alkyl, R3 er -H, R4 er aryl der kan være substitueret med -O- C1-6 alkyl, og R5 er methyl.
3. Forbindelsen eller et farmaceutisk acceptabelt salt deraf beskrevet i krav 1, som er valgt fra gruppen bestående af 4-({[((3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino>methyl)-4-phenylpyrrolidin-l- yl]carbonyl}oxy)benzoesyre, 3-((5-{[(3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino>methyl)-4-phenyl- pyrrolidin-l-yl]carbonyl}-2-furyl)thiophen-2-carboxylsyre, 6-{((3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino}methyl)-4-[3- (trifluormethyl)phenyl]pyrrolidin-l-yl]-6-oxohexanonsyre, 4-[((3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-l- yljbenzoesyre, 3,3-dimethyl-5-[(3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino>methyl)-4-phenylpyrrolidin-l-yl]-5 -oxopentanonsyre, 4-({[((3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-l-yl] carbonyl>amino)benzoesyre, 2,2-dimethyl-5-[(3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino}methyl)-4- phenylpyrrolidin-l-yl]-5-oxopentanonsyre, 4-[({((3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino}methyl)-4-[3- (trifluormethyl)phenyl]pyrrolidin-l-yl>carbonyl)oxy]benzoesyre, 4-({[((3S,4S)-3-(3-fluorphenyl)-4-({[(lR)-l-(l-naphthyl)ethyl]amino> methyl)pyrrolidin-l-yl]carbonyl}oxy)benzoesyre, 4-({[((3S,4S)-3-(3-methylphenyl)-4-({[(lR)-l-(l-naphthyl)ethyl]amino> methyl) py rrol i d i η-1 -yl ] carbonyl }oxy)benzoesyre, 4-({[((3S,4S)-3-(2,3-difluorphenyl)-4-({[(lR)-l-(l-naphthyl)ethyl]amino> methyl)pyrrolidin-l-yl]carbonyl}oxy)benzoesyre, 3.5- difluor-4-[(3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-l-yl] benzoesyre, 3 -methoxy-4-({[(3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino>methyl)-4-phenylpyrrolidin-l-yl]carbonyl}amino)benzoesyre, 4- ({[((3S,4S)-3-({[l-(l-benzothien-3-yl)ethyl]amino>methyl)-4-phenylpyrrolidin-1-yl] carbonyl}oxy)benzoesyre, 5- [((3S,4S)-3-(3-fluorphenyl)-4-({[(lR)-l-(l-naphthyl)ethyl]amino> methyl)pyrrolidin-l-yl]-2,2-dimethyl-5-oxopentanonsyre, 3-methoxy-4-({[(3S,4S)-3-(3-methylphenyl)-4-({[(lR)-l-(l-naphthyl)ethyl] amino>methyl)pyrrolidin-l-yl]carbonyl>amino)benzoesyre, 3.5- difluor-4-[(3S,4S)-3-(3-methylphenyl)-4-({[(lR)-l-(l-naphthyl)ethyl] amino>methyl)pyrrolidin-l-yl]benzoesyre, (lR)-l-(l-naphthyl)-N-({(3S,4S)-4-phenyl-l-[4-(lH-tetrazol-5-yl)phenyl] pyrrolidin-3-yl}methyl)ethanamin, 3-methyl-4-({[(3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino}methyl)-4-phenyl pyrrolidin-l-yl]carbonyl>amino)benzoesyre, 3-chloro-4-({[(3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino>methyl)-4-phenyl pyrrolidin-l-yl]carbonyl>amino)benzoesyre, 3- fluor-4-({[(3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino>methyl)-4-phenylpyrrolidin-l-yl]carbonyl}annino)benzoesyre, 5-[((3S,4S)-3-(2,3-difluorphenyl)-4-({[(lR)-l-(l-naphthyl)ethyl]amino>-methyl) pyrrolidin-l-yl]-2,2-dimethyl-5-oxopentanonsyre, og 4- [((3S,4S)-3-(2,3-difluorphenyl)-4-({[(lR)-l-(l-naphthyl)ethyl]-amino>methyl) pyrrolidin-l-yl]-3,5-difluorbenzoesyre.
4. Forbindelsen eller et farmaceutisk acceptabelt salt deraf beskrevet i krav 1, som er 4-({[((3S,4S)-3-({[(lR)-l-(l-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-l- yl]carbonyl}oxy)benzoesyre.
5. Forbindelsen eller et farmaceutisk acceptabelt salt deraf beskrevet i krav 1, som er 4-({[((3S,4S)-3-(3-fluorphenyl)-4-({[(lR)-l-(l- naphthyl)ethyl]amino}methyl)pyrrolidin-l-yl]carbonyl}oxy)benzoesyre.
6. Farmaceutisk præparat der omfatter forbindelsen beskrevet i et hvilket som helst af kravene 1 to 5 eller et farmaceutisk acceptabelt salt deraf og en farmaceutisk acceptabel bærer.
7. Forbindelsen ifølge et hvilket som helst af kravene 1 til 5 eller et farmaceutisk acceptabelt salt deraf til anvendelse som et medikament.
8. Forbindelsen ifølge et hvilket som helst af kravene 1 til 5 eller et farmaceutisk acceptabelt salt deraf, til anvendelse i behandlingen af hyperparathyroidisme, nyreosteodystrofi eller hypercalcæmi.
9. Forbindelsen ifølge et hvilket som helst af kravene 1 til 5 eller et farmaceutisk acceptabelt salt deraf, til anvendelse i behandlingen af hyperparathyroidisme.
10. Forbindelsen ifølge et hvilket som helst af kravene 1 til 5 eller et farmaceutisk acceptabelt salt deraf, til anvendelse i behandlingen af nyreosteodystrofi.
11. Forbindelsen ifølge et hvilket som helst af kravene 1 til 5 eller et farmaceutisk acceptabelt salt deraf, til anvendelse i behandlingen af hypercalcæmi.
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