TW200301117A - Piperazine derivatives that destabilize androgen receptors - Google Patents

Piperazine derivatives that destabilize androgen receptors Download PDF

Info

Publication number: TW200301117A
Authority: TW; Taiwan
Prior art keywords: trifluoromethyl; methyl; dihydro; benzonitrile; dioxo
Prior art date: 2001-11-23

Application number

TW091134064A

Other languages

English (en)

Chinese (zh)

Inventor

Arwed Cleve

Christoph Huwe

Volker Schulze

Helmut Morack

Dieter Zopf

Hoffmann Jens

Reichel Andreas

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-11-23

Filing date

2002-11-22

Publication date

2003-07-01

2001-11-23 Priority claimed from DE2001159035 external-priority patent/DE10159035A1/de

2002-08-19 Priority claimed from DE2002138742 external-priority patent/DE10238742A1/de

2002-11-22 Application filed by Schering Ag filed Critical Schering Ag

2003-07-01 Publication of TW200301117A publication Critical patent/TW200301117A/zh

Links

108010080146 androgen receptors Proteins 0.000 title claims abstract description 16
102000001307 androgen receptors Human genes 0.000 title claims abstract description 15
150000004885 piperazines Chemical class 0.000 title abstract 2
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 154
206010060862 Prostate cancer Diseases 0.000 claims abstract description 13
208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 13
229910052740 iodine Inorganic materials 0.000 claims abstract description 5
-1 imino (thiomethyl) Chemical group 0.000 claims description 846
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 558
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 399
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 395
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 338
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 306
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 267
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 266
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 133
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 122
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 121
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 114
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 102
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 93
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 93
SOZGHDCEWOLLHV-UHFFFAOYSA-N 2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC=C1C#N SOZGHDCEWOLLHV-UHFFFAOYSA-N 0.000 claims description 88
229910052757 nitrogen Inorganic materials 0.000 claims description 73
125000003118 aryl group Chemical group 0.000 claims description 68
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 53
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 53
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 52
229910052799 carbon Inorganic materials 0.000 claims description 51
239000000126 substance Substances 0.000 claims description 47
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 46
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 44
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 42
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
150000001412 amines Chemical class 0.000 claims description 30
JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 25
229910052717 sulfur Inorganic materials 0.000 claims description 25
239000011593 sulfur Substances 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 24
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 23
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 23
238000011282 treatment Methods 0.000 claims description 23
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 21
206010028980 Neoplasm Diseases 0.000 claims description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 21
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 20
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
125000002947 alkylene group Chemical group 0.000 claims description 18
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 18
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
235000019441 ethanol Nutrition 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
239000004305 biphenyl Substances 0.000 claims description 14
239000006071 cream Substances 0.000 claims description 14
230000005764 inhibitory process Effects 0.000 claims description 14
QUUYRYYUKNNNNS-UHFFFAOYSA-N piperidine-1-carboximidamide Chemical compound NC(=N)N1CCCCC1 QUUYRYYUKNNNNS-UHFFFAOYSA-N 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
239000011737 fluorine Substances 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
239000003098 androgen Substances 0.000 claims description 12
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 10
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
125000004122 cyclic group Chemical group 0.000 claims description 9
150000002576 ketones Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 claims description 9
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 8
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
239000002671 adjuvant Substances 0.000 claims description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 7
125000000623 heterocyclic group Chemical group 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 7
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 7
125000000168 pyrrolyl group Chemical group 0.000 claims description 7
150000003254 radicals Chemical class 0.000 claims description 7
125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
230000001419 dependent effect Effects 0.000 claims description 6
150000002391 heterocyclic compounds Chemical class 0.000 claims description 6
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
239000013067 intermediate product Substances 0.000 claims description 5
125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 5
PJSOCBVWZJGTHW-UHFFFAOYSA-N n-(1h-indazol-5-yl)-5-[3-methoxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl]-1,3-oxazol-2-amine Chemical compound C1=C(OC)C(OCCOCCOC)=CC=C1C(O1)=CN=C1NC1=CC=C(NN=C2)C2=C1 PJSOCBVWZJGTHW-UHFFFAOYSA-N 0.000 claims description 5
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 5
UERQMZVFUXRQOD-UHFFFAOYSA-N piperidine-1-carbothioamide Chemical compound NC(=S)N1CCCCC1 UERQMZVFUXRQOD-UHFFFAOYSA-N 0.000 claims description 5
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
238000006467 substitution reaction Methods 0.000 claims description 5
125000003944 tolyl group Chemical group 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 4
RDYSDCWZHHUGIB-UHFFFAOYSA-N 6,8-dihydroxy-3-methyl-2h-isoquinolin-1-one Chemical compound OC1=CC(O)=C2C(=O)NC(C)=CC2=C1 RDYSDCWZHHUGIB-UHFFFAOYSA-N 0.000 claims description 4
125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000005909 ethyl alcohol group Chemical group 0.000 claims description 4
239000000796 flavoring agent Substances 0.000 claims description 4
125000004222 fluoren-1-yl group Chemical group [H]C1=C([H])C2=C(C([H])=C1[H])C([H])([H])C1=C(*)C([H])=C([H])C([H])=C21 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 3
ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 3
230000001687 destabilization Effects 0.000 claims description 3
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 3
235000019634 flavors Nutrition 0.000 claims description 3
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 3
YRBKSJIXFZPPGF-UHFFFAOYSA-N hexazine Chemical compound N1=NN=NN=N1 YRBKSJIXFZPPGF-UHFFFAOYSA-N 0.000 claims description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
NVPICXQHSYQKGM-UHFFFAOYSA-N piperidine-1-carbonitrile Chemical compound N#CN1CCCCC1 NVPICXQHSYQKGM-UHFFFAOYSA-N 0.000 claims description 3
229940124530 sulfonamide Drugs 0.000 claims description 3
RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 claims description 3
XHTUOWXUBNMVEU-UHFFFAOYSA-N 1-benzoyl-5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione Chemical group O=C1C(CC)(CCC(C)C)C(=O)NC(=O)N1C(=O)C1=CC=CC=C1 XHTUOWXUBNMVEU-UHFFFAOYSA-N 0.000 claims description 2
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
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125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
239000004202 carbamide Substances 0.000 claims description 2
235000013877 carbamide Nutrition 0.000 claims description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
239000000194 fatty acid Substances 0.000 claims description 2
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125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
239000000047 product Substances 0.000 claims description 2
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
150000007857 hydrazones Chemical class 0.000 claims 55
ZYVLSAGHWKSBFW-UHFFFAOYSA-N C1(C=CC(N1)=O)=O.C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound C1(C=CC(N1)=O)=O.C1=CC=CC=2C3=CC=CC=C3CC12 ZYVLSAGHWKSBFW-UHFFFAOYSA-N 0.000 claims 7
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
KBUVRXNOTZNAPI-UHFFFAOYSA-N 1-benzylpyrene Chemical compound C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1CC1=CC=CC=C1 KBUVRXNOTZNAPI-UHFFFAOYSA-N 0.000 claims 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 claims 2
BJRAJQXIQXPPQX-UHFFFAOYSA-N n-[2-(trifluoromethyl)phenyl]piperidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1NC(=O)N1CCCCC1 BJRAJQXIQXPPQX-UHFFFAOYSA-N 0.000 claims 2
229960003495 thiamine Drugs 0.000 claims 2
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OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229940100640 transdermal system Drugs 0.000 description 1
238000012546 transfer Methods 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000005751 tumor progression Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000012447 xenograft mouse model Methods 0.000 description 1
229940033942 zoladex Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
- 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
- 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
- C07D403/06—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
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C07D413/02—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
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
- 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
- C07D417/14—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 three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

TW091134064A 2001-11-23 2002-11-22 Piperazine derivatives that destabilize androgen receptors TW200301117A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2001159035 DE10159035A1 (de)	2001-11-23	2001-11-23	Androgenrezeptor destabilisierende Piperazinderivate
DE2002138742 DE10238742A1 (de)	2002-08-19	2002-08-19	Androgenrezeptor destabilisierende Piperazinderivate

Publications (1)

Publication Number	Publication Date
TW200301117A true TW200301117A (en)	2003-07-01

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ID=26010698

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW091134064A TW200301117A (en)	2001-11-23	2002-11-22	Piperazine derivatives that destabilize androgen receptors

Country Status (5)

Country	Link
AU (1)	AU2002360932A1 (fr)
PE (1)	PE20030708A1 (fr)
TW (1)	TW200301117A (fr)
UY (1)	UY27544A1 (fr)
WO (1)	WO2003043983A1 (fr)

Cited By (1)

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Publication number	Priority date	Publication date	Assignee	Title
TWI813106B (zh) *	2020-12-30	2023-08-21	財團法人工業技術研究院	雄性激素受體結合分子及其用途

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US20030195192A1 (en) *	2002-04-05	2003-10-16	Fortuna Haviv	Nicotinamides having antiangiogenic activity
JP2006519755A (ja) *	2002-11-20	2006-08-31	ロレアル	ピラゾール−カルボキシアミドを含有する毛髪の手入れ用又は睫毛用の組成物、毛髪及び睫毛の成長を刺激し、及び／又は抜毛を防止するためのそれらの使用
FR2847160A1 (fr) *	2002-11-20	2004-05-21	Oreal	Composition capillaire contenant un compose pyrasol-carboxamide, son utilisation pour stimuler la pousse des cheveux et/ou freiner leur chute
US7592466B2 (en)	2003-10-09	2009-09-22	Abbott Laboratories	Ureas having antiangiogenic activity
AU2005216200A1 (en) *	2004-02-22	2005-09-09	Government Of The United States Of America, As Represented By The Secretary Department Of Health And Human Services	Maleiimide anti-tumor phosphatase inhibitors
CN101039927A (zh) *	2004-09-09	2007-09-19	财团法人乙卯研究所	5－羟色胺5－ht3受体激动剂
CN102464631B (zh) *	2010-11-08	2016-08-10	中国科学院上海药物研究所	哌嗪取代的1,3-二取代脲类化合物及哌嗪取代的酰胺类化合物及其制备方法和用途
BR102012000187A2 (pt) *	2012-01-05	2018-04-10	Univ Rio De Janeiro	Derivados n-fenilpiperazínicos antagonistas de adrenoceptores a1a, a1d e de receptores 5-ht1a no tratamento da hiperplasia prostática benigna, composições farmacêuticas contendo os mesmos

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FR2693461B1 (fr) *	1992-07-08	1994-09-02	Roussel Uclaf	Nouvelles phénylimidazolidines substituées, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant.
US5859014A (en) *	1995-06-09	1999-01-12	Syntex (U.S.A.) Inc.	Pyrimidinedione, pyrimidinetrione, triazinedione and tetrahydroquinazolinedione derivatives as α1 -adrenergic receptor antagonists
US5656651A (en) *	1995-06-16	1997-08-12	Biophysica Inc.	Androgenic directed compositions
US6673799B1 (en) *	1998-09-22	2004-01-06	Yamanouchi Pharmaceutical Co. Ltd.	Cyanophenyl derivative

2002
- 2002-10-31 AU AU2002360932A patent/AU2002360932A1/en not_active Abandoned
- 2002-10-31 WO PCT/EP2002/012182 patent/WO2003043983A1/fr not_active Ceased
- 2002-11-21 UY UY27544A patent/UY27544A1/es not_active Application Discontinuation
- 2002-11-22 TW TW091134064A patent/TW200301117A/zh unknown
- 2002-11-22 PE PE2002001124A patent/PE20030708A1/es not_active Application Discontinuation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI813106B (zh) *	2020-12-30	2023-08-21	財團法人工業技術研究院	雄性激素受體結合分子及其用途
US12152035B2 (en)	2020-12-30	2024-11-26	Industrial Technology Research Institute	Androgen receptor binding molecule and use thereof

Also Published As

Publication number	Publication date
AU2002360932A1 (en)	2003-06-10
UY27544A1 (es)	2003-06-30
PE20030708A1 (es)	2003-08-28
WO2003043983A1 (fr)	2003-05-30

Publication	Publication Date	Title
US6861432B2 (en)	2005-03-01	Piperazine derivatives that destabilize androgen receptors
US11247971B2 (en)	2022-02-15	Small molecule inhibitors of lactate dehydrogenase and methods of use thereof
CN101765596B (zh)	2015-04-29	用于治疗过增生症状和与血管生成有关疾病的缺氧诱导因子(hif)抑制剂
JP5275148B2 (ja)	2013-08-28	二環性化合物、その製造法および用途
JP5755417B2 (ja)	2015-07-29	肝細胞増殖因子（分散因子）活性のピラゾール誘導体モジュレーター
JP6234938B2 (ja)	2017-11-22	置換トリアジン誘導体および可溶性グアニル酸シクラーゼの刺激剤としてのその使用
JP6411513B2 (ja)	2018-10-24	Ｅｐ４のリガンドとしての新規なベンズイミダゾール誘導体
US7262185B2 (en)	2007-08-28	Benzazepine derivative, process for producing the same, and use
TW201012798A (en)	2010-04-01	Substituted pyrrolidine-2-carboxamides
KR20130004316A (ko)	2013-01-09	비스아릴-결합된 아릴트리아졸론 및 그의 용도
TW201111378A (en)	2011-04-01	Substituted (heteroarylmethyl) thiohydantoins
NL2000299C2 (nl)	2007-11-20	Verbindingen die bruikbaar zijn bij een behandeling.
JP2012176988A (ja)	2012-09-13	ヘリックス１２指向非ステロイド性抗アンドロゲン
FR2850652A1 (fr)	2004-08-06	Nouveaux derives d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases
TW200804312A (en)	2008-01-16	Novel triazole derivatives as Ghrelin analogue ligands of growth hormone secretagogue receptors
KR102212146B1 (ko)	2021-02-03	신규 피라졸 유도체
JPH11504010A (ja)	1999-04-06	アドレナリン性α▲下１ａ▼受容体アンタゴニスト
CN102666531A (zh)	2012-09-12	杂环-取代的2-乙酰氨基-5-芳基-1,2,4-三唑酮和其应用
TW201004925A (en)	2010-02-01	Hydroxamate-based inhibitors of deacetylases b
NL1031626C2 (nl)	2007-03-19	Verbindingen die bruikbaar zijn in therapie.
CN102272125A (zh)	2011-12-07	哒嗪酮衍生物
TW200301117A (en)	2003-07-01	Piperazine derivatives that destabilize androgen receptors
EP2154139A1 (fr)	2010-02-17	Composé hétérocyclique bicyclique
US20040198799A1 (en)	2004-10-07	Methods of increasing endogenous testosterone levels
JP2006151810A (ja)	2006-06-15	ジヒドロチエノキノリン誘導体及びそれを含む細胞接着阻害剤