HRP20151062T1 - Derivat azola - Google Patents
Derivat azola Download PDFInfo
- Publication number
- HRP20151062T1 HRP20151062T1 HRP20151062TT HRP20151062T HRP20151062T1 HR P20151062 T1 HRP20151062 T1 HR P20151062T1 HR P20151062T T HRP20151062T T HR P20151062TT HR P20151062 T HRP20151062 T HR P20151062T HR P20151062 T1 HRP20151062 T1 HR P20151062T1
- Authority
- HR
- Croatia
- Prior art keywords
- hydroxy
- tetramethylcyclohexyl
- pyrrolidin
- difluoro
- group
- Prior art date
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- 150000007980 azole derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- -1 1,3-benzodioxolanyl group Chemical group 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- NLWIAHYZKRCLBK-NRFANRHFSA-N 1-[(2s)-2-[5-[(3,4-dimethoxyphenoxy)methyl]-1,2-oxazol-3-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=CC([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=NO1 NLWIAHYZKRCLBK-NRFANRHFSA-N 0.000 claims 2
- VHSIFOHQEXXGRB-SFHVURJKSA-N 1-[(2s)-2-[5-[(3,4-dimethoxyphenoxy)methyl]-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=NN=C([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)O1 VHSIFOHQEXXGRB-SFHVURJKSA-N 0.000 claims 2
- KWMWOAPLSZBDAS-SFHVURJKSA-N 2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-[(2s)-2-[5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C=2OC(COC=3C=CC=CC=3)=NN=2)CCC1 KWMWOAPLSZBDAS-SFHVURJKSA-N 0.000 claims 2
- CSZFOLMDHFDLLR-FQEVSTJZSA-N 2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-[(2s)-2-[5-(pyridin-3-yloxymethyl)-1,2-oxazol-3-yl]pyrrolidin-1-yl]ethanone Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(COC=3C=NC=CC=3)=C2)CCC1 CSZFOLMDHFDLLR-FQEVSTJZSA-N 0.000 claims 2
- IRZKMFNDDJGNME-NRFANRHFSA-N 2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-[(2s)-2-[5-[(3,4,5-trimethoxyphenoxy)methyl]-1,2-oxazol-3-yl]pyrrolidin-1-yl]ethanone Chemical compound COC1=C(OC)C(OC)=CC(OCC=2ON=C(C=2)[C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=C1 IRZKMFNDDJGNME-NRFANRHFSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005494 pyridonyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- XOZZPNYSQIRLEN-SFHVURJKSA-N 1-[(2S)-2-[3-[(3,4-dimethoxyphenoxy)methyl]-1H-1,2,4-triazol-5-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=NN=C([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)N1 XOZZPNYSQIRLEN-SFHVURJKSA-N 0.000 claims 1
- MNZLFETUWMJCGM-SFHVURJKSA-N 1-[(2s)-2-[3-[(3,4-dimethoxyphenoxy)methyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=NOC([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=N1 MNZLFETUWMJCGM-SFHVURJKSA-N 0.000 claims 1
- DJLXXGDXRAQEBP-FQEVSTJZSA-N 1-[(2s)-2-[3-[(3,4-dimethoxyphenoxy)methyl]-1,2-oxazol-5-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=NOC([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=C1 DJLXXGDXRAQEBP-FQEVSTJZSA-N 0.000 claims 1
- BLKNOVDRFRHCTP-SFHVURJKSA-N 1-[(2s)-2-[5-[(3,4-dimethoxyphenoxy)methyl]-1,3,4-thiadiazol-2-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=NN=C([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)S1 BLKNOVDRFRHCTP-SFHVURJKSA-N 0.000 claims 1
- IZQLJVNWGSKPHE-FQEVSTJZSA-N 1-[(2s)-2-[5-[(3,4-dimethoxyphenoxy)methyl]-1,3-oxazol-2-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=CN=C([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)O1 IZQLJVNWGSKPHE-FQEVSTJZSA-N 0.000 claims 1
- UPOILGSZTBWGJW-FQEVSTJZSA-N 1-[(2s)-2-[5-[(3,4-dimethoxyphenoxy)methyl]-1,3-thiazol-2-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=CN=C([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)S1 UPOILGSZTBWGJW-FQEVSTJZSA-N 0.000 claims 1
- GOJHEQCIVYDFGQ-IBGZPJMESA-N 1-[(2s)-2-[5-[(3,4-dimethoxyphenoxy)methyl]-1-methyl-1,2,4-triazol-3-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=NC([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=NN1C GOJHEQCIVYDFGQ-IBGZPJMESA-N 0.000 claims 1
- YUNDVXLCFCVZKG-NRFANRHFSA-N 1-[(2s)-2-[5-[(3,4-dimethoxyphenoxy)methyl]-1h-pyrazol-3-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=CC([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=NN1 YUNDVXLCFCVZKG-NRFANRHFSA-N 0.000 claims 1
- GFBHHWWMHWIPDC-KRWDZBQOSA-N 1-[(2s)-2-[5-[(dimethylamino)methyl]-1,2-oxazol-3-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound O1C(CN(C)C)=CC([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=N1 GFBHHWWMHWIPDC-KRWDZBQOSA-N 0.000 claims 1
- DKKAYYVWUDHGNW-AWEZNQCLSA-N 1-[(2s)-2-[5-[(dimethylamino)methyl]-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]-2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound O1C(CN(C)C)=NN=C1[C@H]1N(C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)CCC1 DKKAYYVWUDHGNW-AWEZNQCLSA-N 0.000 claims 1
- WGLZDPMUPHZAIY-NRFANRHFSA-N 2,2-difluoro-1-[(2s)-2-[5-[(3-fluorophenoxy)methyl]-1,2-oxazol-3-yl]pyrrolidin-1-yl]-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)ethanone Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(COC=3C=C(F)C=CC=3)=C2)CCC1 WGLZDPMUPHZAIY-NRFANRHFSA-N 0.000 claims 1
- FXAZPTAOQVPRAZ-NRFANRHFSA-N 2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-[(2s)-2-[5-(phenoxymethyl)-1,2-oxazol-3-yl]pyrrolidin-1-yl]ethanone Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(COC=3C=CC=CC=3)=C2)CCC1 FXAZPTAOQVPRAZ-NRFANRHFSA-N 0.000 claims 1
- KJMXWTZQNNHVEP-SFHVURJKSA-N 2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-[(2s)-2-[5-(pyrimidin-4-yloxymethyl)-1,2-oxazol-3-yl]pyrrolidin-1-yl]ethanone Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(COC=3N=CN=CC=3)=C2)CCC1 KJMXWTZQNNHVEP-SFHVURJKSA-N 0.000 claims 1
- DUBUTXOMIKLOHU-IBGZPJMESA-N 2,2-difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-[(2s)-2-[5-(pyrimidin-5-yloxymethyl)-1,2-oxazol-3-yl]pyrrolidin-1-yl]ethanone Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(COC=3C=NC=NC=3)=C2)CCC1 DUBUTXOMIKLOHU-IBGZPJMESA-N 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- URNUHNTWOWWNFJ-QFIPXVFZSA-N C1=C(OC)C(OC)=CC=C1OCC1=CC([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=NN1C Chemical compound C1=C(OC)C(OC)=CC=C1OCC1=CC([C@H]2N(CCC2)C(=O)C(F)(F)C2(O)CC(C)(C)CC(C)(C)C2)=NN1C URNUHNTWOWWNFJ-QFIPXVFZSA-N 0.000 claims 1
- IVAVIXJIWJPKAB-FQEVSTJZSA-N C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(CN3C=CC(=O)C=C3)=C2)CCC1 Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(CN3C=CC(=O)C=C3)=C2)CCC1 IVAVIXJIWJPKAB-FQEVSTJZSA-N 0.000 claims 1
- HQOQKNBZJXSNRZ-SFHVURJKSA-N C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(CN3C=NC(=O)C=C3)=C2)CCC1 Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(CN3C=NC(=O)C=C3)=C2)CCC1 HQOQKNBZJXSNRZ-SFHVURJKSA-N 0.000 claims 1
- ZUENTVYTXARFQE-NRFANRHFSA-N C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(CNC(=O)C=3C=CC=CC=3)=C2)CCC1 Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(CNC(=O)C=3C=CC=CC=3)=C2)CCC1 ZUENTVYTXARFQE-NRFANRHFSA-N 0.000 claims 1
- GHAXLCRMGIHLDE-NRFANRHFSA-N C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(CNS(=O)(=O)C=3C=CC=CC=3)=C2)CCC1 Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(CNS(=O)(=O)C=3C=CC=CC=3)=C2)CCC1 GHAXLCRMGIHLDE-NRFANRHFSA-N 0.000 claims 1
- SCZZOLISEGDUED-FQEVSTJZSA-N C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(COC=3C=CN=CC=3)=C2)CCC1 Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C2=NOC(COC=3C=CN=CC=3)=C2)CCC1 SCZZOLISEGDUED-FQEVSTJZSA-N 0.000 claims 1
- SZHNYZMZSQRMNU-SFHVURJKSA-N C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C=2OC(CNC(=O)C=3C=CC=CC=3)=NN=2)CCC1 Chemical compound C1C(C)(C)CC(C)(C)CC1(O)C(F)(F)C(=O)N1[C@H](C=2OC(CNC(=O)C=3C=CC=CC=3)=NN=2)CCC1 SZHNYZMZSQRMNU-SFHVURJKSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/42—Oxazoles
-
- 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
-
- 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
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Description
DERIVAT AZOLA
Claims (17)
1. Spoj prikazan s formulom (1)
[image]
naznačen time da R1 predstavlja slijedeću formulu (2)
[image]
prsten A predstavlja bilo koji od prstena predstavljenih sa slijedećim formulama (4)
[image]
X predstavlja -(CH2)m-X1-(CH2)n-;
X1 predstavlja vezu, -O-, -NRaC(=O)-, -C(=O)NRb-, -NRcS(=O)2-, ili -S(=O)2NRd-;
Ra, Rb, Rc, i Rd koji mogu biti isti ili različiti svaki predstavljaju vodikov atom ili C1-6 alkil skupinu;
m i n koji mogu biti isti ili različiti svaki predstavljaju cijeli broj od 0-3;
R2 predstavlja aril skupinu, heteroaril skupinu (navedena aril ili heteroaril skupina mogu biti supstituirane s 1-3 supstitucijskih skupina odabranih iz skupine koja sadrži atom halogena, -2-C1-6 alkil skupinu, te C1-6 alkoksi skupinu (navedena C1-6 alkil skupina ili C1-6 alkoksi skupina mogu biti supstituirane s 1-3 supstitucijskih skupina odabranih iz skupine koja sadrži atom halogena i hidroksi skupinu)), 1,3-benzodioksolanil skupinu, indolil skupinu, morfolil skupinu, hidroksi skupinu, C1-6 alkil skupinu (navedena C1-6 alkil skupina može biti supstituirana s 1-2 hidroksi skupine), amino skupinu, mono-C1-6 alkilamino skupinu, di-C1-6 alkilamino skupinu, C1-6 alkoksi skupinu, C1-6 alkilsulfoniloksi skupinu, piridonil skupinu, ili pirimidinonil skupinu ili njihova farmaceutski prihvatljiva sol.
2. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da X je veza, -CH2O-, -CH2-, -(CH2)2-, -(CH2)3-, -O-, -CH2-NHC(=O)-, -CH2-NHC(=O)-CH2-, ili -CH2-NHS(=O)2-.
3. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da X je -CH2O- ili -CH2-.
4. Spoj ili njegova farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 1 do 3, naznačen time da je prsten A bilo koji od prstenova sa slijedećim formulama (5):
[image]
5. Spoj ili njegova farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 1 do 4, naznačen time da R2 je fenil skupina, piridil skupina, piridazinil skupina ili pirimidil skupina (navedena fenil skupina, piridil skupina ili pirimidil skupina mogu biti supstituirane s 1-3 atoma halogena ili metoksi skupinama), piridonil skupina, ili pirimidinonil skupina.
6. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 5, naznačen time da R2 je fenil skupina ili piridil skupina (navedena fenil skupina ili piridil skupina mogu biti supstituirane s 1-3 metoksi skupine.)
7. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da je prsten A bilo koji od prstenova sa slijedećim formulama (5):
[image]
X je -CH2O- ili -(CH2)2-,
R2 je fenil skupina ili piridil skupina (navedena fenil skupina ili piridil skupina mogu biti supstituirane s 1-3 metoksi skupine).
8. Spoj prema zahtjevu 1, naznačen time da je
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)izoksazol-3-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-((piridin-3-iloksi)metil)izoksazol-3-il)pirolidin-1-il)etanon,
(S)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-((3,4,5-trimetoksifenoksi)metil)izoksazol-3-il)pirolidin-1-il)etanon,
(S)-N-((3-(1-(2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)acetil)pirolidin-2-il)izoksazol-5-il)metil)benzamid,
(S)-N-((3-(1-(2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)acetil)pirolidin-2-il)izoksazol-5-il)metil)benzensulfonamid,
(S)-1-(2-(5-((dimetilamino)metil)izoksazol-3-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)-1,3,4-oksadiazol-2-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-(fenoksimetil)-1,3,4-oksadiazol-2-il)pirolidin-1-il)etanon,
(S)-N-((5-(1-(2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)acetil)pirolidin-2-il)-1,3,4-oksadiazol-2-il)metil)benzamid,
(S)-1-(2-(5-((dimetilamino)metil)-1,3,4-oksadiazol-2-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(3-((3,4-dimetoksifenoksi)metil)-1,2,4-oksadiazol-5-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)-1-metil-1H-pirazol-3-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(3-((3,4-dimetoksifenoksi)metil)-izoksazol-5-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)-1H-pirazol-3-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)-1,3,4-tiadiazol-2-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)-4H-1,2,4-triazol-3-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)-1-metil-1H-1,2,4-triazol-3-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)oksazol-2-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)tiazol-2-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon,
(S)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-(fenoksimetil)izoksazol-3-il)pirolidin-1-il)etanon,
(S)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-((pirimidin-5-iloksi)metil)izoksazol-3-il)pirolidin-1-il)etanon,
(S)-1-((3-(1-(2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)acetil)pirolidin-2-il)izoksazol-5-il)metil)pirimidin-4(1H)-on,
(S)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-((pirimidin-4-iloksi)metil)izoksazol-3-il)pirolidin-1-il)etanon,
(S)-2,2-difluoro-1-(2-(5-((3-fluorofenoksi)metil)izoksazol-3-il)pirolidin-1-il)-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon, ili
(S)-1-((3-(1-(2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)acetil)pirolidin-2-il)izoksazol-5-il)metil)piridin-4(1H)-on, ili
njihova farmaceutski prihvatljiva sol.
9. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj je (S)-1-(2-(5-((3,4-dimetoksifenoksi)metil)izoksazol-3-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon predstavljen sa slijedećom formulom ili njegova farmaceutski prihvatljiva sol.
[image]
10. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj je (S)-1-(2-(5-((3,4-Dimetoksifenoksi)metil)-1,3,4-oksadiazol-2-il)pirolidin-1-il)-2,2-difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)etanon ili njegova farmaceutski prihvatljiva sol.
11. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj je (S)-2,2-Difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-((3,4,5-trimetoksifenoksi)metil)izoksazol-3-il)pirolidin-1-il)etanon predstavljen sa slijedećom formulom ili njegova farmaceutski prihvatljiva sol.
[image]
12. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj je (S)-2,2-Difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-(fenoksimetil)-1,3,4-oksadiazol-2-il)pirolidin-1-il)etanon ili njegova farmaceutski prihvatljiva sol.
13. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj je (S)-2,2-Difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-((piridin-3-iloksi)metil)izoksazol-3-il)pirolidin-1-il)etanon predstavljen sa slijedećom formulom ili njegova farmaceutski prihvatljiva sol.
[image]
14. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj je (S)-2,2-Difluoro-2-(1-hidroksi-3,3,5,5-tetrametilcikloheksil)-1-(2-(5-((piridin-4-iloksi)metil)izoksazol-3-il)pirolidin-1-il)etanon ili njegova farmaceutski prihvatljiva sol.
15. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da spoj je spoj prikazan sa slijedećom formulom ili njegova farmaceutski prihvatljiva sol:
[image]
16. Farmaceutski proizvod naznačen time da kao aktivni sastojak sadrži spoj ili njegovu farmaceutski prihvatljivu sol prema bilo kojem od zahtjeva 1 do 15.
17. Spoj ili njegova farmaceutski prihvatljiva sol prema bilo kojem od zahtjeva 1 do 15 naznačen time da je za uporabu za prevenciju ili liječenje alopecije.
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| JP2011056149 | 2011-03-15 | ||
| PCT/JP2012/056624 WO2012124750A1 (ja) | 2011-03-15 | 2012-03-15 | アゾール誘導体 |
| EP12757646.0A EP2687524B1 (en) | 2011-03-15 | 2012-03-15 | Azole derivative |
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| AU2016224536A1 (en) * | 2015-02-25 | 2017-09-07 | Taisho Pharmaceutical Co., Ltd. | Hair growth composition for cutaneous application |
| JP2017078044A (ja) * | 2015-10-21 | 2017-04-27 | 大正製薬株式会社 | 発毛剤組成物 |
| AU2020417293A1 (en) | 2020-01-03 | 2022-09-01 | Berg Llc | Polycyclic amides as UBE2K modulators for treating cancer |
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| KR0159766B1 (ko) | 1989-10-16 | 1998-12-01 | 후지사와 토모키치로 | 양모제 조성물 |
| WO1992019593A1 (en) | 1991-05-09 | 1992-11-12 | Vertex Pharmaceuticals Incorporated | Novel immunosuppressive compounds |
| US5859031A (en) | 1995-06-07 | 1999-01-12 | Gpi Nil Holdings, Inc. | Small molecule inhibitors of rotamase enzyme activity |
| US5945441A (en) | 1997-06-04 | 1999-08-31 | Gpi Nil Holdings, Inc. | Pyrrolidine carboxylate hair revitalizing agents |
| GB9804426D0 (en) | 1998-03-02 | 1998-04-29 | Pfizer Ltd | Heterocycles |
| CA2333997A1 (en) | 1998-06-02 | 1999-12-09 | Bristol-Myers Squibb Company | Neurotrophic difluoroamide agents |
| KR20010052503A (ko) | 1998-06-03 | 2001-06-25 | 다니엘 피. 맥컬럼 | Ｎ-헤테로사이클릭 카복실산 또는 카복실산 등입체의ｎ-결합된 설폰아미드 |
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| GB9815696D0 (en) | 1998-07-20 | 1998-09-16 | Pfizer Ltd | Heterocyclics |
| US6228872B1 (en) | 1998-11-12 | 2001-05-08 | Bristol-Myers Squibb Company | Neurotrophic diamide and carbamate agents |
| PL352432A1 (en) | 1999-07-09 | 2003-08-25 | Ortho Mc Neil Pharmaceutical | Neurothrophic pyrolydines and piperidines, their affinite composition and methods of using them |
| JP2001247569A (ja) | 1999-08-12 | 2001-09-11 | Japan Tobacco Inc | ピロリジン誘導体又はピペリジン誘導体及びその医薬用途 |
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| JP4221989B2 (ja) | 2002-09-30 | 2009-02-12 | 大正製薬株式会社 | オキサジアゾール誘導体 |
| JP4240978B2 (ja) | 2002-09-30 | 2009-03-18 | 大正製薬株式会社 | アリールオキシメチルオキサジアゾール誘導体 |
| RU2457826C2 (ru) * | 2006-12-20 | 2012-08-10 | Тайсо Фармасьютикал Ко., Лтд. | Профилактическое или терапевтическое средство от алопеции |
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