SK100894A3 - Indole compounds, method of their producing, intermediates and pharmaceutical preparations on their base - Google Patents

Indole compounds, method of their producing, intermediates and pharmaceutical preparations on their base Download PDF

Info

Publication number: SK100894A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; alkyl; group; alkoxy
Prior art date: 1992-02-28

Application number

SK1008-94A

Other languages

English (en)

Slovak (sk)

Inventor

Graham Nigel Maw

Julian Blagg

Colin W Greengrass

Paul W Finn

Original Assignee

Pfizer

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.)

1992-02-28

Filing date

1994-08-24

Publication date

1995-04-12

1994-08-24 Application filed by Pfizer filed Critical Pfizer

1995-04-12 Publication of SK100894A3 publication Critical patent/SK100894A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 98
150000002475 indoles Chemical class 0.000 title claims description 13
239000000543 intermediate Substances 0.000 title abstract description 8
239000000825 pharmaceutical preparation Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 276
150000003839 salts Chemical class 0.000 claims abstract description 80
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 50
238000002360 preparation method Methods 0.000 claims abstract description 35
125000003118 aryl group Chemical group 0.000 claims abstract description 32
125000002947 alkylene group Chemical group 0.000 claims abstract description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 13
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
125000004450 alkenylene group Chemical group 0.000 claims abstract description 10
125000004419 alkynylene group Chemical group 0.000 claims abstract description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
-1 indole compound Chemical class 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 43
125000004432 carbon atom Chemical group C* 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 30
229910052799 carbon Inorganic materials 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical group 0.000 claims description 20
125000001072 heteroaryl group Chemical group 0.000 claims description 20
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 19
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 18
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
230000007062 hydrolysis Effects 0.000 claims description 17
238000006460 hydrolysis reaction Methods 0.000 claims description 17
150000001721 carbon Chemical group 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
230000002378 acidificating effect Effects 0.000 claims description 11
230000002401 inhibitory effect Effects 0.000 claims description 11
201000004384 Alopecia Diseases 0.000 claims description 10
125000005605 benzo group Chemical group 0.000 claims description 10
239000011734 sodium Substances 0.000 claims description 10
229910052708 sodium Inorganic materials 0.000 claims description 10
108010029908 3-oxo-5-alpha-steroid 4-dehydrogenase Proteins 0.000 claims description 9
102000001779 3-oxo-5-alpha-steroid 4-dehydrogenase Human genes 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
201000005825 prostate adenocarcinoma Diseases 0.000 claims description 7
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
239000003377 acid catalyst Substances 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000011591 potassium Substances 0.000 claims description 6
229910052700 potassium Inorganic materials 0.000 claims description 6
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 5
SMHUIHXBNYCWHC-UHFFFAOYSA-N 2-methyl-2-[4-(2-methylpropyl)phenyl]-1,3-benzodioxole-5-carboxylic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1(C)OC2=CC(C(O)=O)=CC=C2O1 SMHUIHXBNYCWHC-UHFFFAOYSA-N 0.000 claims description 5
208000002874 Acne Vulgaris Diseases 0.000 claims description 5
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
206010020112 Hirsutism Diseases 0.000 claims description 5
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 5
206010039792 Seborrhoea Diseases 0.000 claims description 5
206010000496 acne Diseases 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
231100000360 alopecia Toxicity 0.000 claims description 5
230000003676 hair loss Effects 0.000 claims description 5
125000003003 spiro group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical class C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 4
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
238000009109 curative therapy Methods 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical compound C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 claims description 3
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 3
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 claims description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims description 3
229940054051 antipsychotic indole derivative Drugs 0.000 claims description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
238000003776 cleavage reaction Methods 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
150000002084 enol ethers Chemical class 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
230000007017 scission Effects 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
KIMLMLODGDVZSJ-UHFFFAOYSA-N 4-[3-[2-methyl-2-[4-(2-methylpropyl)phenyl]-1,3-benzodioxole-5-carbonyl]indol-1-yl]butanoic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1(C)OC2=CC(C(=O)C=3C4=CC=CC=C4N(CCCC(O)=O)C=3)=CC=C2O1 KIMLMLODGDVZSJ-UHFFFAOYSA-N 0.000 claims description 2
HVALIUHAZKCBCO-UHFFFAOYSA-N CC(C)CC1=CC=C(C=C1)C2(OC3=C(O2)C=C(C=C3)C(=O)C4=CC5=CC=CC=C5N4)C Chemical compound CC(C)CC1=CC=C(C=C1)C2(OC3=C(O2)C=C(C=C3)C(=O)C4=CC5=CC=CC=C5N4)C HVALIUHAZKCBCO-UHFFFAOYSA-N 0.000 claims description 2
125000005277 alkyl imino group Chemical group 0.000 claims description 2
125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 17
150000001924 cycloalkanes Chemical class 0.000 claims 1
125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 42
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
125000001475 halogen functional group Chemical group 0.000 abstract 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 36
239000002585 base Chemical class 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
239000000047 product Substances 0.000 description 25
239000000243 solution Substances 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000002253 acid Substances 0.000 description 21
229960003604 testosterone Drugs 0.000 description 21
238000010992 reflux Methods 0.000 description 19
238000005160 1H NMR spectroscopy Methods 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
210000002307 prostate Anatomy 0.000 description 14
239000002904 solvent Substances 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
230000002829 reductive effect Effects 0.000 description 12
NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000010410 layer Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
230000020477 pH reduction Effects 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
239000000872 buffer Substances 0.000 description 7
230000003301 hydrolyzing effect Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
241000700159 Rattus Species 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000003098 androgen Substances 0.000 description 6
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical class C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
239000003921 oil Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000000758 substrate Substances 0.000 description 6
238000011282 treatment Methods 0.000 description 6
108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 5
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 5
238000005119 centrifugation Methods 0.000 description 5
239000012024 dehydrating agents‎ Substances 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 5
239000002245 particle Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
239000002841 Lewis acid Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
238000010828 elution Methods 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
KBPUBCVJHFXPOC-UHFFFAOYSA-N ethyl 3,4-dihydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(O)=C1 KBPUBCVJHFXPOC-UHFFFAOYSA-N 0.000 description 4
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
150000007517 lewis acids Chemical class 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000012545 processing Methods 0.000 description 4
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239000003086 colorant Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229960001389 doxazosin Drugs 0.000 description 1
RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000007071 enzymatic hydrolysis Effects 0.000 description 1
238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
QVEBYVTWJMNUHK-UHFFFAOYSA-N ethyl 4-[3-[2-methyl-2-[4-(2-methylpropyl)phenyl]-1,3-benzodioxole-5-carbonyl]indol-1-yl]butanoate Chemical compound C12=CC=CC=C2N(CCCC(=O)OCC)C=C1C(=O)C(C=C1O2)=CC=C1OC2(C)C1=CC=C(CC(C)C)C=C1 QVEBYVTWJMNUHK-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
229960002074 flutamide Drugs 0.000 description 1
MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
206010020718 hyperplasia Diseases 0.000 description 1
230000002390 hyperplastic effect Effects 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000006210 lotion Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000012261 overproduction Methods 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
229960001289 prazosin Drugs 0.000 description 1
IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
229940095585 testosterone-5-alpha reductase inhibitors for benign prostatic hypertrophy Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
229940045860 white wax Drugs 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Endocrinology (AREA)
Diabetes (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK1008-94A 1992-02-28 1994-08-24 Indole compounds, method of their producing, intermediates and pharmaceutical preparations on their base SK100894A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB929204365A GB9204365D0 (en)	1992-02-28	1992-02-28	Indoles
PCT/EP1993/000380 WO1993017014A1 (fr)	1992-02-28	1993-02-16	DERIVES D'INDOLE SERVANT D'INHIBITEURS DE LA STEROIDE-5$(a)-REDUCTASE

Publications (1)

Publication Number	Publication Date
SK100894A3 true SK100894A3 (en)	1995-04-12

Family

ID=10711259

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1008-94A SK100894A3 (en)	1992-02-28	1994-08-24	Indole compounds, method of their producing, intermediates and pharmaceutical preparations on their base

Country Status (24)

Country	Link
US (1)	US5767139A (fr)
EP (1)	EP0628040B1 (fr)
JP (1)	JP2540016B2 (fr)
KR (1)	KR950700287A (fr)
CN (1)	CN1079465A (fr)
AT (1)	ATE164376T1 (fr)
AU (1)	AU3497793A (fr)
BR (1)	BR9305991A (fr)
CA (1)	CA2117610C (fr)
CZ (1)	CZ207794A3 (fr)
DE (1)	DE69317651T2 (fr)
DK (1)	DK0628040T3 (fr)
ES (1)	ES2115053T3 (fr)
FI (2)	FI943931A0 (fr)
GB (1)	GB9204365D0 (fr)
HR (1)	HRP930227A2 (fr)
HU (1)	HUT71126A (fr)
IL (1)	IL104816A0 (fr)
MX (1)	MX9301112A (fr)
NO (1)	NO943187L (fr)
RU (1)	RU94042391A (fr)
SK (1)	SK100894A3 (fr)
WO (1)	WO1993017014A1 (fr)
ZA (1)	ZA931383B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL109728A0 (en) *	1993-05-28	1994-08-26	Pfizer Res & Dev	Indoles
ES2099007B1 (es) *	1993-07-16	1997-12-01	Pfizer Res & Dev	Derivados de indol.
GB9317096D0 (en) *	1993-08-17	1993-09-29	Pfizer Ltd	Indoles
GB9403516D0 (en) *	1994-02-24	1994-04-13	Pfizer Ltd	Indoles
GB9409583D0 (en) *	1994-05-13	1994-07-06	Pfizer Ltd	Indoles
EP0820441B1 (fr) *	1995-04-10	2002-06-26	Fujisawa Pharmaceutical Co., Ltd.	Derives d'indole utilises en tant qu'inhibiteurs de cgmp-pde
CA2338855A1 (fr)	1998-08-03	2000-02-17	Eli Lilly And Company	Inhibiteurs de spla2 de type indole
FR2796274B1 (fr) *	1999-07-16	2001-09-21	Oreal	Utilisation de l'acide 4,6-dimethoxy-indole 2-carboxylique ou de ses derives pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute
FR2796279B1 (fr)	1999-07-16	2001-09-21	Oreal	Utilisation de l'acide 4,6-dimethoxy-indole 2-carboxylique ou de ses derives pour le traitement de la seborrhee
UA79504C2 (en) *	2002-11-07	2007-06-25	Organon Nv	Indols for treating diseases associated with androgen receptors
HRP20050396A2 (en) *	2002-11-07	2005-06-30	Akzo Nobel N.V.	Indoles useful in the treatment of androgen-receptor related diseases
TW200602317A (en)	2004-04-23	2006-01-16	Akzo Nobel Nv	Novel androgens
GB201102913D0 (en)	2011-02-18	2011-04-06	Univ Birmingham	Novel therapeutic

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3557142A (en) *	1968-02-20	1971-01-19	Sterling Drug Inc	4,5,6,7-tetrahydro-indole-lower-alkanoic acids and esters
PH23498A (en) *	1984-08-06	1989-08-16	Sterling Drug Inc	3-carbonyl-1-aminoalkyl-1h-indoles,composition and use thereof
CA2036307C (fr) *	1990-03-08	2002-07-09	Susan Jean Ward	Compositions anti-glaucome, a base de 3-arylcarbonyl-1-aminoalkyl-1h-indole; methode d'utilisation
GB9011335D0 (en) *	1990-05-21	1990-07-11	Fujisawa Pharmaceutical Co	Indolebutyric acid derivatives and process for preparation thereof
IL109728A0 (en) *	1993-05-28	1994-08-26	Pfizer Res & Dev	Indoles

1992
- 1992-02-28 GB GB929204365A patent/GB9204365D0/en active Pending
1993
- 1993-02-16 FI FI943931A patent/FI943931A0/fi not_active IP Right Cessation
- 1993-02-16 JP JP5514517A patent/JP2540016B2/ja not_active Expired - Fee Related
- 1993-02-16 WO PCT/EP1993/000380 patent/WO1993017014A1/fr not_active Ceased
- 1993-02-16 ES ES93903984T patent/ES2115053T3/es not_active Expired - Lifetime
- 1993-02-16 EP EP93903984A patent/EP0628040B1/fr not_active Expired - Lifetime
- 1993-02-16 BR BR9305991A patent/BR9305991A/pt not_active Application Discontinuation
- 1993-02-16 CA CA002117610A patent/CA2117610C/fr not_active Expired - Fee Related
- 1993-02-16 US US08/256,734 patent/US5767139A/en not_active Expired - Fee Related
- 1993-02-16 AU AU34977/93A patent/AU3497793A/en not_active Abandoned
- 1993-02-16 AT AT93903984T patent/ATE164376T1/de not_active IP Right Cessation
- 1993-02-16 RU RU94042391/04A patent/RU94042391A/ru unknown
- 1993-02-16 DE DE69317651T patent/DE69317651T2/de not_active Expired - Fee Related
- 1993-02-16 HU HU9402466A patent/HUT71126A/hu unknown
- 1993-02-16 CZ CZ942077A patent/CZ207794A3/cs unknown
- 1993-02-16 DK DK93903984.8T patent/DK0628040T3/da active
- 1993-02-22 IL IL104816A patent/IL104816A0/xx unknown
- 1993-02-24 HR HR9204365.2A patent/HRP930227A2/hr not_active Application Discontinuation
- 1993-02-26 ZA ZA931383A patent/ZA931383B/xx unknown
- 1993-02-26 MX MX9301112A patent/MX9301112A/es unknown
- 1993-02-27 CN CN93103673A patent/CN1079465A/zh active Pending
1994
- 1994-08-24 SK SK1008-94A patent/SK100894A3/sk unknown
- 1994-08-27 KR KR1019940703018A patent/KR950700287A/ko not_active Ceased
- 1994-08-29 NO NO943187A patent/NO943187L/no unknown
2000
- 2000-08-09 FI FI20001771A patent/FI20001771A7/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
NO943187L (no)	1994-09-13
FI20001771A7 (fi)	2000-08-09
KR950700287A (ko)	1995-01-16
EP0628040A1 (fr)	1994-12-14
AU3497793A (en)	1993-09-13
BR9305991A (pt)	1997-10-21
CZ207794A3 (en)	1995-01-18
CA2117610C (fr)	2000-07-18
WO1993017014A1 (fr)	1993-09-02
JP2540016B2 (ja)	1996-10-02
ATE164376T1 (de)	1998-04-15
US5767139A (en)	1998-06-16
ES2115053T3 (es)	1998-06-16
FI943931A7 (fi)	1994-08-26
GB9204365D0 (en)	1992-04-08
MX9301112A (es)	1994-07-29
DE69317651D1 (en)	1998-04-30
NO943187D0 (no)	1994-08-29
CN1079465A (zh)	1993-12-15
EP0628040B1 (fr)	1998-03-25
RU94042391A (ru)	1996-08-10
DE69317651T2 (de)	1998-07-09
DK0628040T3 (da)	1998-04-27
HU9402466D0 (en)	1994-10-28
FI943931A0 (fi)	1994-08-26
ZA931383B (en)	1994-08-26
JPH07500347A (ja)	1995-01-12
HRP930227A2 (en)	1996-10-31
HUT71126A (en)	1995-11-28
CA2117610A1 (fr)	1993-09-02
IL104816A0 (en)	1993-06-10

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SK8494A3 (en)	1994-11-09	Endoles, method of their manufacturing and pharmaceutical preparations on their base
DE69317651T2 (de)	1998-07-09	Indol derivate als steroid 5 alpha-reductase inhibitoren
Aikawa et al.	2015	Synthesis and biological evaluation of novel selective androgen receptor modulators (SARMs). Part I
Hartmann et al.	1995	Pyridyl-substituted tetrahydrocyclopropa [a] naphthalenes: highly active and selective inhibitors of P450 arom
HUP0302405A2 (hu)	2003-10-28	Új benzofuránszármazékok
DE69422629T2 (de)	2000-06-29	Indolderivate als 5-alpha-reductase-1 inhibitoren
Guarna et al.	2000	Synthesis of 8-chloro-benzo [c] quinolizin-3-ones as potent and selective inhibitors of human steroid 5α-reductase 1
Hartmann et al.	2004	CYP 17 and CYP 19 inhibitors. Evaluation of fluorine effects on the inhibiting activity of regioselectively fluorinated 1-(Naphthalen-2-ylmethyl) imidazoles
KR100580742B1 (ko)	2006-05-15	벤조[ｃ]퀴놀리진 유도체 및 5 알파-리덕타제억제제로서의 용도
FI113864B (fi)	2004-06-30	Menetelmä indolijohdannaisten valmistamiseksi, jotka ovat käyttökelpoisia steroidi-5alfa-reduktaasin inhibiittoreina
EP0194945B1 (fr)	1988-11-02	Nouveaux dérivés de l'acide thiophène acétique, leur procédé de préparation, les intermédiaires obtenus, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant
WO2001060781A2 (fr)	2001-08-23	Composes diphenyle, preparations et utilisations associees
WO1995023143A1 (fr)	1995-08-31	Derives d'indoles en tant qu'inhibiteurs de la testosterone-5-alpha-reductase
MXPA00006219A (en)	2001-06-26	Benzo[c]quinolizine derivatives and their use as 5 alpha-reductases inhibitors