BG61321B2 - (1н-имидазол-1-илметил) заместени бензимидазолови производни - Google Patents

Info

Publication number

BG61321B2

BG61321B2 BG097951A BG9795193A BG61321B2 BG 61321 B2 BG61321 B2 BG 61321B2 BG 097951 A BG097951 A BG 097951A BG 9795193 A BG9795193 A BG 9795193A BG 61321 B2 BG61321 B2 BG 61321B2

Authority

BG

Bulgaria

Prior art keywords

parts

formula

compound

imidazol

alkyl

Prior art date

1986-09-15

Links

• Espacenet
• Global Dossier
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• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 213
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 238000000034 method Methods 0.000 claims abstract description 27
• 238000002360 preparation method Methods 0.000 claims abstract description 17
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 14
• 125000001424 substituent group Chemical group 0.000 claims abstract description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
• 239000002585 base Substances 0.000 claims description 138
• -1 amine salt Chemical class 0.000 claims description 127
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 239000001257 hydrogen Substances 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 42
• 150000002431 hydrogen Chemical group 0.000 claims description 31
• 239000002253 acid Substances 0.000 claims description 30
• 238000006243 chemical reaction Methods 0.000 claims description 28
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 239000003098 androgen Substances 0.000 claims description 19
• 150000003254 radicals Chemical class 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 14
• 238000007363 ring formation reaction Methods 0.000 claims description 14
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 239000003638 chemical reducing agent Substances 0.000 claims description 11
• 239000012442 inert solvent Substances 0.000 claims description 11
• 229910052751 metal Inorganic materials 0.000 claims description 11
• 239000002184 metal Substances 0.000 claims description 11
• 239000003153 chemical reaction reagent Substances 0.000 claims description 10
• 230000002829 reductive effect Effects 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
• 238000007126 N-alkylation reaction Methods 0.000 claims description 8
• 239000003513 alkali Substances 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 5
• 238000010934 O-alkylation reaction Methods 0.000 claims description 5
• 229910052783 alkali metal Inorganic materials 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
• 238000002955 isolation Methods 0.000 claims description 5
• 238000000746 purification Methods 0.000 claims description 5
• 238000011065 in-situ storage Methods 0.000 claims description 4
• DCGOMTSIZLGUOK-UHFFFAOYSA-N 6-[imidazol-1-yl(phenyl)methyl]-2-methyl-1h-benzimidazole Chemical compound C1=C2NC(C)=NC2=CC=C1C(N1C=NC=C1)C1=CC=CC=C1 DCGOMTSIZLGUOK-UHFFFAOYSA-N 0.000 claims description 3
• 150000007513 acids Chemical class 0.000 claims description 3
• 230000009471 action Effects 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• 150000001340 alkali metals Chemical class 0.000 claims description 3
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
• 150000001735 carboxylic acids Chemical class 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 125000000524 functional group Chemical group 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 239000002609 medium Substances 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 230000008878 coupling Effects 0.000 claims description 2
• 238000010168 coupling process Methods 0.000 claims description 2
• 238000005859 coupling reaction Methods 0.000 claims description 2
• 239000012458 free base Substances 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• UGFHIPBXIWJXNA-UHFFFAOYSA-N liarozole Chemical compound ClC1=CC=CC(C(C=2C=C3NC=NC3=CC=2)N2C=NC=C2)=C1 UGFHIPBXIWJXNA-UHFFFAOYSA-N 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
• 238000004519 manufacturing process Methods 0.000 claims 2
• 101100482220 Sulfurisphaera tokodaii (strain DSM 16993 / JCM 10545 / NBRC 100140 / 7) triC gene Proteins 0.000 claims 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
• 150000001447 alkali salts Chemical class 0.000 claims 1
• 150000001556 benzimidazoles Chemical class 0.000 claims 1
• 125000004093 cyano group Chemical group *C#N 0.000 claims 1
• 230000001131 transforming effect Effects 0.000 claims 1
• 229940088597 hormone Drugs 0.000 abstract description 6
• 239000005556 hormone Substances 0.000 abstract description 6
• 230000002378 acidificating effect Effects 0.000 abstract description 4
• 241001465754 Metazoa Species 0.000 abstract description 2
• 230000005764 inhibitory process Effects 0.000 abstract description 2
• 230000002265 prevention Effects 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 361
• 239000000203 mixture Substances 0.000 description 187
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 130
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 106
• 239000003480 eluent Substances 0.000 description 98
• 239000000243 solution Substances 0.000 description 97
• 239000000047 product Substances 0.000 description 94
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 75
• 229960001701 chloroform Drugs 0.000 description 75
• 239000011541 reaction mixture Substances 0.000 description 67
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 55
• 238000003756 stirring Methods 0.000 description 53
• 239000000543 intermediate Substances 0.000 description 50
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 48
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 44
• 239000000284 extract Substances 0.000 description 39
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• 238000010898 silica gel chromatography Methods 0.000 description 33
• 239000002904 solvent Substances 0.000 description 32
• 229960004592 isopropanol Drugs 0.000 description 30
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 229910021529 ammonia Inorganic materials 0.000 description 24
• 239000000706 filtrate Substances 0.000 description 24
• 238000001816 cooling Methods 0.000 description 23
• 238000010992 reflux Methods 0.000 description 22
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 21
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• 239000003054 catalyst Substances 0.000 description 21
• 229960000583 acetic acid Drugs 0.000 description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 19
• 235000011054 acetic acid Nutrition 0.000 description 18
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• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 17
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 17
• 235000011114 ammonium hydroxide Nutrition 0.000 description 16
• 229920006395 saturated elastomer Polymers 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
• 239000010410 layer Substances 0.000 description 14
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
• 238000004440 column chromatography Methods 0.000 description 13
• 239000007858 starting material Substances 0.000 description 13
• 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 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
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• 239000000908 ammonium hydroxide Substances 0.000 description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
• 150000002148 esters Chemical group 0.000 description 10
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
• 150000001299 aldehydes Chemical class 0.000 description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
• 239000005457 ice water Substances 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
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• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 8
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• 238000009835 boiling Methods 0.000 description 8
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
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• 239000005909 Kieselgur Substances 0.000 description 7
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