BRPI0610183A2 - Composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, uso de um composto ou de um sal farmaceuticamente aceitável do mesmo - Google Patents

Info

Publication number

BRPI0610183A2

BRPI0610183A2 BRPI0610183-6A BRPI0610183A BRPI0610183A2 BR PI0610183 A2 BRPI0610183 A2 BR PI0610183A2 BR PI0610183 A BRPI0610183 A BR PI0610183A BR PI0610183 A2 BRPI0610183 A2 BR PI0610183A2

Authority

BR

Brazil

Prior art keywords

formula

methyl

compound

compound according

mmol

Prior art date

2005-05-13

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 190
• 150000003839 salts Chemical class 0.000 title claims abstract description 43
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 22
• 208000029725 Metabolic bone disease Diseases 0.000 claims abstract description 12
• 206010049088 Osteopenia Diseases 0.000 claims abstract description 12
• 239000003085 diluting agent Substances 0.000 claims abstract description 10
• 206010057671 Female sexual dysfunction Diseases 0.000 claims abstract description 8
• 206010057672 Male sexual dysfunction Diseases 0.000 claims abstract description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
• -1 pyridiazinyl Chemical group 0.000 claims description 53
• 230000002829 reductive effect Effects 0.000 claims description 46
• 125000000623 heterocyclic group Chemical group 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 125000004076 pyridyl group Chemical group 0.000 claims description 26
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 239000000460 chlorine Substances 0.000 claims description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 210000000988 bone and bone Anatomy 0.000 claims description 19
• 210000003205 muscle Anatomy 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 150000002431 hydrogen Chemical group 0.000 claims description 15
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 238000002560 therapeutic procedure Methods 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• 206010058359 Hypogonadism Diseases 0.000 claims description 7
• 206010060862 Prostate cancer Diseases 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 206010024264 Lethargy Diseases 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims description 6
• 208000010392 Bone Fractures Diseases 0.000 claims description 5
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 5
• 238000009167 androgen deprivation therapy Methods 0.000 claims description 5
• 230000003930 cognitive ability Effects 0.000 claims description 5
• 230000008717 functional decline Effects 0.000 claims description 5
• 201000001881 impotence Diseases 0.000 claims description 5
• 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 5
• 208000001076 sarcopenia Diseases 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 3
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000004306 triazinyl group Chemical group 0.000 claims description 3
• 150000003973 alkyl amines Chemical class 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 1
• NFGGQMYSOLVBLF-UHFFFAOYSA-N phenyl(1h-pyrrol-2-yl)methanone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CN1 NFGGQMYSOLVBLF-UHFFFAOYSA-N 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 59
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 20
• 208000035475 disorder Diseases 0.000 abstract description 16
• 208000036119 Frailty Diseases 0.000 abstract 1
• 206010003549 asthenia Diseases 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 95
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 55
• 239000000203 mixture Substances 0.000 description 53
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
• 238000006243 chemical reaction Methods 0.000 description 46
• 102100032187 Androgen receptor Human genes 0.000 description 44
• 108010080146 androgen receptors Proteins 0.000 description 44
• 238000002360 preparation method Methods 0.000 description 42
• 239000000243 solution Substances 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• 239000012141 concentrate Substances 0.000 description 38
• 230000000694 effects Effects 0.000 description 38
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
• 235000019439 ethyl acetate Nutrition 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000003098 androgen Substances 0.000 description 32
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
• 238000005160 1H NMR spectroscopy Methods 0.000 description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
• 239000000284 extract Substances 0.000 description 29
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
• 238000003756 stirring Methods 0.000 description 28
• 239000000849 selective androgen receptor modulator Substances 0.000 description 27
• 239000003446 ligand Substances 0.000 description 26
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 25
• 210000001519 tissue Anatomy 0.000 description 25
• 238000011282 treatment Methods 0.000 description 25
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
• 235000019341 magnesium sulphate Nutrition 0.000 description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
• 238000009739 binding Methods 0.000 description 21
• 230000027455 binding Effects 0.000 description 20
• 239000000047 product Substances 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 17
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• 229910002027 silica gel Inorganic materials 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• 239000010410 layer Substances 0.000 description 15
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 14
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• 239000003921 oil Substances 0.000 description 13
• 235000019198 oils Nutrition 0.000 description 13
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
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• 239000011734 sodium Substances 0.000 description 10
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