HRP20161745T1 - N-[4-(kinolin-4-iloksi)cikloheksil(methil)](hetero)arilkarboksamidi kao antagonisti receptora androgena, njihova proizvodnja i uporaba kao medicinskih proizvoda - Google Patents
N-[4-(kinolin-4-iloksi)cikloheksil(methil)](hetero)arilkarboksamidi kao antagonisti receptora androgena, njihova proizvodnja i uporaba kao medicinskih proizvoda Download PDFInfo
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- HRP20161745T1 HRP20161745T1 HRP20161745TT HRP20161745T HRP20161745T1 HR P20161745 T1 HRP20161745 T1 HR P20161745T1 HR P20161745T T HRP20161745T T HR P20161745TT HR P20161745 T HRP20161745 T HR P20161745T HR P20161745 T1 HRP20161745 T1 HR P20161745T1
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- cyclohexyl
- trans
- oxy
- methyl
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims 5
- 229940123407 Androgen receptor antagonist Drugs 0.000 title 1
- 239000003936 androgen receptor antagonist Substances 0.000 title 1
- 125000005842 heteroatom Chemical group 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 18
- 239000012453 solvate Substances 0.000 claims 18
- -1 amino- Chemical class 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 230000003463 hyperproliferative effect Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- LKYNGTHMKCTTQC-UHFFFAOYSA-N 1,2-oxazole-3-carboxamide Chemical compound NC(=O)C=1C=CON=1 LKYNGTHMKCTTQC-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229940127554 medical product Drugs 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- QFVJJXMRDAEYGJ-UHFFFAOYSA-N 3,4-difluoro-N-(4-quinolin-4-yloxycyclohexyl)benzamide Chemical compound C1=C(F)C(F)=CC=C1C(=O)NC1CCC(OC=2C3=CC=CC=C3N=CC=2)CC1 QFVJJXMRDAEYGJ-UHFFFAOYSA-N 0.000 claims 1
- SMJFZIKHGRDRRK-UHFFFAOYSA-N 4-fluoro-N-[[4-(8-fluoroquinolin-4-yl)oxycyclohexyl]methyl]benzamide Chemical group C1=CC(F)=CC=C1C(=O)NCC1CCC(OC=2C3=CC=CC(F)=C3N=CC=2)CC1 SMJFZIKHGRDRRK-UHFFFAOYSA-N 0.000 claims 1
- ZEPTVVCRIXZZHA-JCNLHEQBSA-N Cc1cc(no1)C(=O)NC[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N Chemical compound Cc1cc(no1)C(=O)NC[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N ZEPTVVCRIXZZHA-JCNLHEQBSA-N 0.000 claims 1
- HWJBWEFGDIMYFK-WKILWMFISA-N Cc1cc(no1)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N Chemical compound Cc1cc(no1)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N HWJBWEFGDIMYFK-WKILWMFISA-N 0.000 claims 1
- GZACDNAICNLZMR-WGSAOQKQSA-N Cc1ccc(cc1F)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N Chemical compound Cc1ccc(cc1F)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N GZACDNAICNLZMR-WGSAOQKQSA-N 0.000 claims 1
- ZAPKMVNTBKOLHE-WGSAOQKQSA-N Fc1cc(F)cc(c1)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N Chemical compound Fc1cc(F)cc(c1)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N ZAPKMVNTBKOLHE-WGSAOQKQSA-N 0.000 claims 1
- YVOIFCKRNYSADD-QAQDUYKDSA-N Fc1cc(ccc1Cl)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N Chemical compound Fc1cc(ccc1Cl)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N YVOIFCKRNYSADD-QAQDUYKDSA-N 0.000 claims 1
- JUJUXYMWBSDELG-QAQDUYKDSA-N Fc1ccc(cc1Cl)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N Chemical compound Fc1ccc(cc1Cl)C(=O)N[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N JUJUXYMWBSDELG-QAQDUYKDSA-N 0.000 claims 1
- ZMKIYBGNNRFQBA-UHFFFAOYSA-N N-[4-(8-bromoquinolin-4-yl)oxycyclohexyl]-3-fluorobenzamide Chemical compound FC1=CC=CC(C(=O)NC2CCC(CC2)OC=2C3=CC=CC(Br)=C3N=CC=2)=C1 ZMKIYBGNNRFQBA-UHFFFAOYSA-N 0.000 claims 1
- REQDIIXPFUIHKZ-UHFFFAOYSA-N N-[4-(8-bromoquinolin-4-yl)oxycyclohexyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC2CCC(CC2)OC=2C3=CC=CC(Br)=C3N=CC=2)=N1 REQDIIXPFUIHKZ-UHFFFAOYSA-N 0.000 claims 1
- CZSVKYOFKOKXIO-KOMQPUFPSA-N O=C(NC[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N)c1ccon1 Chemical compound O=C(NC[C@H]1CC[C@@H](CC1)Oc1ccnc2c(cccc12)C#N)c1ccon1 CZSVKYOFKOKXIO-KOMQPUFPSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 102000001307 androgen receptors Human genes 0.000 claims 1
- 108010080146 androgen receptors Proteins 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims 1
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D413/12—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 chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (15)
1. Spoj s općom formulom (I)
[image]
naznačen time da
R1 predstavlja H, cijano, fluor, klor ili brom;
A predstavlja fenil ili 5-člani heteroaril, pri čemu ovaj fenil ili ovaj 5-člani heteroaril je proizvoljno supstituiran s jednim, dva ili tri supstituenata koji su odabrani međusobno neovisno iz skupa koji čine: halogen, cijano, alkil-, haloalkil-, cikloalkil-, heterociklil-, hidroksi, alkoksi-, fluoralkoksi-, cikloalkiloksi-, amino-, alkilamino-, dialkilamino-, cikloalkilamino-, alkilcikloalkilamino-, dicikloalkilamino-, alkilkarbonilamino-, cikloalkilkarbonilamino-, alkilsulfanil-, cikloalkilsulfanil-, alkilsulfonil-, cikloalkilsulfonil-, aminosulfonil-, alkilaminosulfonil-, cikloalkilaminosulfonil-; alkoksikarbonil-;
n = 0, 1 ili 2;
ili jedna od njegovih soli, jedan od njegovih solvata ili solvati njegovih soli.
2. Spoj prema zahtjevu 1, naznačen time R1 predstavlja H, cijano, fluor ili brom; A predstavlja fenil ili 5-člani heteroaril, pri čemu ovaj fenil ili ovaj 5-člani heteroaril je proizvoljno supstituiran s jednim ili dva supstituenta koji su odabrani međusobno neovisno iz skupa koji čine: halogen, cijano, alkil-, haloalkil-; n = 0 ili 1; ili jedna od njegovih soli, jedan od njegovih solvata ili solvati njegovih soli.
3. Spoj prema zahtjevu 1, naznačen time
R1 predstavlja H, brom, cijano ili fluor;
A predstavlja fenil ili 5-člani heteroaril, pri čemu ovaj fenil ili ovaj 5-člani heteroaril je proizvoljno supstituiran s jednim ili dva supstituenta koji su odabrani međusobno neovisno iz skupa koji čine: fluor, klor, cijano, metil ili trifluormetil;
n = 0 for 1;
ili jedna od njegovih soli, jedan od njegovih solvata ili solvati njegovih soli.
4. Spoj prema zahtjevu 1, naznačen time da A predstavlja fenil, pri čemu ovaj fenil je proizvoljno supstituiran s jednim ili dva supstituenta koji su odabrani međusobno neovisno iz skupa koji čine fluor, klor, cijano, metil, trifluormetil.
5. Spoj prema zahtjevu 1, naznačen time da A predstavlja fenil, pri čemu je ovaj fenil proizvoljno supstituiran sa supstituentom fluorom.
6. Spoj prema zahtjevu 1, naznačen time da je odabran od
N-({trans-4-[(8-fluorkinolin-4-il)oksi]cikloheksil}metil)-4-fluorbenzamida,
N-{trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}-5-metilizoksazol-3-karboksamida,
N-[trans-4-(4-kinoliloksi)cikloheksil]-3,4-difluorbenzamida,
N-({trans-4-[(8-fluorkinolin-4-il)oksi]cikloheksil}metil)-3-metilizoksazol-4-karboksamida,
N-({trans-4-[(8-fluorkinolin-4-il)oksi]cikloheksil}metil)-izoksazol-5-karboksamida,
N-({trans-4-[(8-fluorkinolin-4-il)oksi]cikloheksil}metil)izoksazol-3-karboksamida,
N-({trans-4-[(8-fluorkinolin-4-il)oksi]cikloheksil}metil)-5-metilizoksazol-3-karboksamida,
N-({trans-4-[(8-fluorkinolin-4-il)oksi]cikloheksil}metil)-1H-pirazol-3-karboksamida,
N-{[trans-4-(4-kinoliloksi)cikloheksil]metil}-3,4-difluorbenzamida,
N-{[trans-4-(4-kinoliloksi)cikloheksil]metil}-3-fluorbenzamida,
N-{[trans-4-(4-kinoliloksi)cikloheksil]metil}-5-metilizoksazol-3-karboksamida,
N-{trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}-3-fluorbenzamida,
N-{trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}-3,4-difluorbenzamida,
N-{trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}-3-fluor-4-metilbenzamida,
N-{trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}-4-cijanobenzamida,
N-{trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}-3-fluor-4-(trifluormetil)benzamida,
N-{trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}-4-fluorbenzamida,
N-{trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}-3-klor-4-fluorbenzamida,
N-{trans-4-(4-kinoliloksi)cikloheksil}-3-fluorbenzamida,
N-({trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}metil)-5-metilizoksazol-3-karboksamida,
N-({trans-4-[(8-bromkinolin-4-il)oksi]cikloheksil}metil)izoksazol-3-karboksamida,
N-{[trans-4-(4-kinoliloksi)cikloheksil]metil}-4-cijanobenzamida,
N-trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}-3-fluorbenzamida,
N-trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}-3,4-difluorbenzamida,
N-trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}-4-fluorbenzamida,
N-{trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}-5-metilizoksazol-3-karboksamida,
3-klor-N-{trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}-4-fluorbenzamida,
N-{trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}-3-fluor-4-metilbenzamida,
4-klor-N-{trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}-3-fluorbenzamida,
N-{trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}-3,5-difluorbenzamida,
N-({trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}metil)izoksazol-3-karboksamida,
N-({trans-4-[(8-cijanokinolin-4-il)oksi]cikloheksil}metil)-5-metilizoksazol-3-karboksamida.
7. Postupak za proizvodnju spoja s formulom (I) ili jedne od njegovih soli, jednog od njegovih solvata ili solvata njegovih soli prema zahtjevu 1, naznačen time da spoj s općom formulom (II)
[image]
u kojoj R1 i n imaju značenje definirano u zahtjevu 1,
reagira sa kiselim kloridom A-COCl, u kojem A ima značenje definirano u zahtjevu 1,
u prisutnosti baze,
i dobiveni spoj s formulom (I) se proizvoljno pretvara s odgovarajućim (i) otapalom i/ili (ii) bazom ili kiselinom u njegov solvat, sol i/ili solvat soli.
8. Postupak za proizvodnju spoja s formulom (I) ili jedne od njegovih soli, njegovih solvata ili solvata njegovih soli prema zahtjevu 1, naznačen time da spoj s općom formulom (II)
[image]
u kojoj R1 i n imaju značenje definirano u zahtjevu 1,
reagira s kiselinom A-COOH, u kojoj A ima značenje definirano u zahtjevu 1,
u prisutnosti pogodnog reagensa za spajanje i baze,
i dobiveni spoj s formulom (I) se proizvoljno pretvara s odgovarajućim (i) otapalom i/ili (ii) bazom ili kiselinom u njegov solvat, sol i/ili solvat soli.
9. Postupak za proizvodnju spoja s formulom (I) prema zahtjevu 1, u kojoj R1= cijano, ili jedna od njegovih soli, jedan od njegovih solvata ili solvati njegovih soli, naznačen time da se spoj s općom formulom (VII)
[image]
u kojoj n i A imaju značenje definirano u zahtjevu 1,
podvrgava reakciji izmjene brom/cijano,
i dobiveni spoj s formulom (I) u kojoj R1 = cijano, se proizvoljno pretvara s odgovarajućim (i) otapalom i/ili (ii) bazom ili kiselinom u njegov solvat, sol i/ili solvat soli.
10. Spoj kako je definirano u jednom od zahtjeva 1 do 6, naznačen time da je za uporabu za liječenje i/ili sprječavanje hiperproliferativne bolesti.
11. Spoj za uporabu prema zahtjevu 10, naznačen time da hiperproliferativna bolest je hiperproliferativna bolest koja je ovisna o androgenom receptoru.
12. Spoj kako je definirano u jednom od zahtjeva 1 do 6, naznačen time da je za uporabu za liječenje i/ili sprječavanje sindroma policističnih jajnika.
13. Medicinski proizvod, naznačen time da sadrži spoj kako je definirano u jednom od zahtjeva 1 do 6, u kombinaciji s drugom aktivnom tvari.
14. Medicinski proizvod, naznačen time da sadrži spoj kako je definirano u jednom od zahtjeva 1 do 6, u kombinaciji s inertnim, netoksičnim, farmaceutski prikladnim pomoćnim sredstvom.
15. Spoj s općom formulom (II)
[image]
naznačen time da R1 i n imaju značenje definirano u zahtjevu 1.
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| EP12004764 | 2012-06-26 | ||
| PCT/EP2013/063118 WO2014001247A1 (en) | 2012-06-26 | 2013-06-24 | N-[4-(Quinolin-4-yloxy)cyclohexyl(methyl)](hetero)arylcarboxamides as androgen receptor antagonists, production and use thereof as medicinal products |
| EP13731325.0A EP2864291B1 (en) | 2012-06-26 | 2013-06-24 | N-[4-(quinolin-4-yloxy)cyclohexyl(methyl)](hetero)arylcarboxamides as androgen receptor antagonists, production and use thereof as medicinal products |
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| CA2945819A1 (en) * | 2014-04-22 | 2015-10-29 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| AR102537A1 (es) | 2014-11-05 | 2017-03-08 | Flexus Biosciences Inc | Agentes inmunomoduladores |
| TWI726969B (zh) | 2016-01-11 | 2021-05-11 | 比利時商健生藥品公司 | 用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物 |
| EP3452451A4 (en) * | 2016-05-04 | 2019-11-13 | Bristol-Myers Squibb Company | INDOLEAMINE 2,3-DIOXYGENASE INHIBITORS AND METHODS OF USE |
| KR20190003686A (ko) | 2016-05-04 | 2019-01-09 | 브리스톨-마이어스 스큅 컴퍼니 | 인돌아민 2,3-디옥시게나제의 억제제 및 그의 사용 방법 |
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| AU2001268040A1 (en) | 2000-06-23 | 2002-01-08 | Eli Lilly And Company | Methods and compounds for inhibiting mrp1 |
| DE60233736D1 (de) | 2001-06-22 | 2009-10-29 | Kirin Pharma K K | Chinolinderivat und chinazolinderivat, die die selbstphosphorylierung des hepatocytus-proliferator-rezeptors hemmen, und diese enthaltende medizinische zusammensetzung |
| CN100528846C (zh) | 2002-09-11 | 2009-08-19 | 株式会社吴羽 | 胺化合物及其用途 |
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| SE0302573D0 (sv) | 2003-09-26 | 2003-09-26 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
| EP1725238A4 (en) | 2004-03-17 | 2009-04-01 | Glaxo Group Ltd | ACETYLCHOLINE M 3 MUSCARINIC RECEPTOR ANTAGONISTS |
| SE0401342D0 (sv) | 2004-05-25 | 2004-05-25 | Astrazeneca Ab | Therapeutic compounds |
| WO2005117570A1 (en) | 2004-05-27 | 2005-12-15 | Jack Saffron | Feeding dish to prevent pest infestation |
| RU2007119427A (ru) | 2004-11-09 | 2008-12-20 | СмитКлайн Бичем Корпорейшн (US) | Соединения, являющиеся ингибиторами гликогенфосфорилазы, и фармацевтические композиции на их основе |
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