LT3950B - Process for the preparation of (1h-azol-1-ylmethyl)substituted benzotriazole derivatives - Google Patents
Process for the preparation of (1h-azol-1-ylmethyl)substituted benzotriazole derivatives Download PDFInfo
- Publication number
- LT3950B LT3950B LTIP1625A LTIP1625A LT3950B LT 3950 B LT3950 B LT 3950B LT IP1625 A LTIP1625 A LT IP1625A LT IP1625 A LTIP1625 A LT IP1625A LT 3950 B LT3950 B LT 3950B
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- LT
- Lithuania
- Prior art keywords
- formula
- parts
- compound
- base
- benzotriazole
- Prior art date
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- -1 (1h-azol-1-ylmethyl)substituted benzotriazole Chemical class 0.000 title claims abstract description 110
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 161
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 22
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 3
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims abstract 2
- 239000002585 base Substances 0.000 claims description 273
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 13
- 239000012964 benzotriazole Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 238000007126 N-alkylation reaction Methods 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- 239000000262 estrogen Substances 0.000 abstract description 19
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 125000001544 thienyl group Chemical group 0.000 abstract description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 239000005556 hormone Substances 0.000 abstract 1
- 229940088597 hormone Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 193
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 142
- 239000000203 mixture Substances 0.000 description 117
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 239000003480 eluent Substances 0.000 description 66
- 239000000047 product Substances 0.000 description 65
- 239000000243 solution Substances 0.000 description 65
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- 239000011541 reaction mixture Substances 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
- 239000000543 intermediate Substances 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 239000000741 silica gel Substances 0.000 description 31
- 229910002027 silica gel Inorganic materials 0.000 description 31
- 239000000284 extract Substances 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 229960001701 chloroform Drugs 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229940011871 estrogen Drugs 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 17
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 102000014654 Aromatase Human genes 0.000 description 12
- 108010078554 Aromatase Proteins 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 235000008504 concentrate Nutrition 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229910045601 alloy Inorganic materials 0.000 description 10
- 239000000956 alloy Substances 0.000 description 10
- 239000002199 base oil Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 150000002367 halogens Chemical group 0.000 description 7
- 229910017604 nitric acid Inorganic materials 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 235000010288 sodium nitrite Nutrition 0.000 description 7
- FZOSXLXDYSQZMM-UHFFFAOYSA-N 1-hydroxy-6-(imidazol-1-ylmethyl)benzotriazole Chemical compound C1=C2N(O)N=NC2=CC=C1CN1C=CN=C1 FZOSXLXDYSQZMM-UHFFFAOYSA-N 0.000 description 6
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
- 239000005909 Kieselgur Substances 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 229960005309 estradiol Drugs 0.000 description 6
- 229930182833 estradiol Natural products 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 4
- RYBZZHARXAYSBW-UHFFFAOYSA-N 6-[bromo(phenyl)methyl]-1-methylbenzotriazole;hydrobromide Chemical compound Br.C1=C2N(C)N=NC2=CC=C1C(Br)C1=CC=CC=C1 RYBZZHARXAYSBW-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 210000001589 microsome Anatomy 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 230000003169 placental effect Effects 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- HVMPEJLLFWORGU-UHFFFAOYSA-N 1-hydroxy-6-(1-imidazol-1-ylethyl)benzotriazole;hydrochloride Chemical compound Cl.C=1C=C2N=NN(O)C2=CC=1C(C)N1C=CN=C1 HVMPEJLLFWORGU-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- IVIDKWNVUKRSMS-UHFFFAOYSA-N 4-[imidazol-1-yl-(3-methylbenzotriazol-5-yl)methyl]benzoic acid;hydrochloride Chemical compound Cl.C1=C2N(C)N=NC2=CC=C1C(N1C=NC=C1)C1=CC=C(C(O)=O)C=C1 IVIDKWNVUKRSMS-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001565 benzotriazoles Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
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- 239000000460 chlorine Substances 0.000 description 3
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- 238000006193 diazotization reaction Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 238000000099 in vitro assay Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000003880 polar aprotic solvent Substances 0.000 description 3
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
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- 229930192474 thiophene Natural products 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5602187A | 1987-06-01 | 1987-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1625A LTIP1625A (en) | 1995-07-25 |
| LT3950B true LT3950B (en) | 1996-05-27 |
Family
ID=22001654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1625A LT3950B (en) | 1987-06-01 | 1993-12-16 | Process for the preparation of (1h-azol-1-ylmethyl)substituted benzotriazole derivatives |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0293978B1 (da) |
| JP (1) | JPH0662612B2 (da) |
| KR (1) | KR970000952B1 (da) |
| CN (1) | CN1022184C (da) |
| AU (1) | AU603446B2 (da) |
| BG (2) | BG50278A3 (da) |
| CA (1) | CA1307271C (da) |
| CY (1) | CY1866A (da) |
| DE (1) | DE3884055T2 (da) |
| DK (1) | DK175218B1 (da) |
| ES (1) | ES2059490T3 (da) |
| FI (1) | FI90078C (da) |
| HK (1) | HK114795A (da) |
| HU (2) | HU201056B (da) |
| IE (1) | IE61823B1 (da) |
| IL (1) | IL86551A (da) |
| LT (1) | LT3950B (da) |
| LV (1) | LV10452B (da) |
| NO (1) | NO169900C (da) |
| NZ (1) | NZ224714A (da) |
| PT (1) | PT87623B (da) |
| RU (1) | RU1838308C (da) |
| UA (1) | UA11192A (da) |
| ZA (1) | ZA883861B (da) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2002859C (en) * | 1988-11-29 | 1998-12-29 | Jean P. F. Van Wauwe | Method of treating epithelial disorders |
| US5157046A (en) * | 1988-11-29 | 1992-10-20 | Janssen Pharmaceutica N.V. | Method of treating epithelial disorders |
| GB8827820D0 (en) * | 1988-11-29 | 1988-12-29 | Janssen Pharmaceutica Nv | (1h-azol-1-ylmethyl)substituted quinoline derivatives |
| DE59010171D1 (de) * | 1989-07-14 | 1996-04-11 | Ciba Geigy Ag | Substituierte Benzonitrile |
| CA2026792A1 (en) * | 1989-11-01 | 1991-05-02 | Michael N. Greco | (6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1h-benzotriazole derivatives |
| US5066656A (en) * | 1989-11-01 | 1991-11-19 | Janssen Pharmaceutica N.V. | Pharmacologically active (6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)- and (5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl) substituted 1H-benzotriazole derivatives |
| NZ236440A (en) * | 1989-12-15 | 1993-07-27 | Merck & Co Inc | Reversal of sexual phenotype in poultry using an inhibitor of steroid biotransformation and/or aromatase inhibitor, poultry produced by this process |
| AU7124691A (en) * | 1990-02-27 | 1991-08-29 | Ciba-Geigy Ag | Benzofurans |
| DE4010797A1 (de) * | 1990-04-04 | 1991-10-10 | Hoechst Ag | Substituierte azole, verfahren zu deren herstellung, diese enthaltende mittel und deren verwendung |
| EP0457716A1 (de) * | 1990-04-20 | 1991-11-21 | Ciba-Geigy Ag | Naphthalinderivate |
| TW224461B (da) * | 1990-09-18 | 1994-06-01 | Ciba Geigy Ag | |
| US5162337A (en) * | 1990-10-05 | 1992-11-10 | Merck & Co., Inc. | Animal growth promotion |
| TW210334B (da) * | 1990-12-12 | 1993-08-01 | Ciba Geigy Ag | |
| CH683151A5 (de) * | 1991-04-24 | 1994-01-31 | Ciba Geigy Ag | Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus. |
| EP0641785B1 (en) * | 1991-09-02 | 1999-10-27 | Yamanouchi Pharmaceutical Co. Ltd. | Triazolylated tertiary amine compound or salt thereof |
| US5635521A (en) * | 1991-09-23 | 1997-06-03 | Sandoz Ltd. | Imidazolylmethyl-pyridines |
| JP2700595B2 (ja) * | 1992-05-21 | 1998-01-21 | 呉羽化学工業株式会社 | アゾール誘導体を含有する抗アロマターゼ剤 |
| JPH08502990A (ja) * | 1992-11-10 | 1996-04-02 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 鏡像体的に純粋な６−［（４−クロロフェニル）（１ｈ−１，２，４−トリアゾール−１−イル）メチル−１−メチル−１ｈ−ベンゾトリアゾールの製造方法 |
| EP0684235A1 (en) * | 1994-05-27 | 1995-11-29 | Mochida Pharmaceutical Co., Ltd. | Novel azolyl methyl phenyl derivatives having aromatase inhibitory activity |
| WO1997006788A1 (en) * | 1995-08-14 | 1997-02-27 | Janssen Pharmaceutica N.V. | Transdermal administration of vorozole |
| IT1286866B1 (it) * | 1996-10-28 | 1998-07-17 | Menarini Farma Ind | Composti furano-eterociclici,loro preparazione ed uso come inibitori di aromatasi |
| KR100559816B1 (ko) * | 1996-12-24 | 2006-03-10 | 쥬가이 세이야쿠 가부시키가이샤 | Ｎｏｓ 저해작용을 가진 방향족 아민 유도체 |
| EP1295880A4 (en) * | 2000-06-28 | 2004-05-06 | Ssp Co Ltd | IMIDAZOLE DERIVATIVES OR THEIR SALTS AND THE MEDICINES CONTAINING THEM |
| US7135575B2 (en) | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| KR101099281B1 (ko) * | 2003-03-03 | 2011-12-26 | 어레이 바이오파마 인크. | ｐ38 억제제 및 그의 사용 방법 |
| EP1845973B1 (en) | 2005-01-21 | 2015-08-12 | Astex Therapeutics Limited | Pharmaceutical compounds |
| EP1874304B1 (en) * | 2005-04-29 | 2009-07-15 | Janssen Pharmaceutica N.V. | Benzotriazole derivatives as cannabinoid receptor antagonists |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| CN101291950B (zh) | 2005-09-15 | 2013-01-02 | 科学与工业研究会 | 咪唑基取代的类固醇和茚满-1-酮衍生物 |
| WO2007089646A1 (en) | 2006-01-31 | 2007-08-09 | Array Biopharma Inc. | Kinase inhibitors and methods of use thereof |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP2013540145A (ja) * | 2010-10-21 | 2013-10-31 | ウニベルシテート デス ザールランデス | コルチゾール依存性疾患の治療用の選択的ｃｙｐ１１ｂ１阻害剤 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4410539A (en) | 1980-10-23 | 1983-10-18 | Pfizer Inc. | Heterocyclic thromboxane synthetase inhibitors and pharmaceutical compositions containing them |
| EP0165781A1 (en) | 1984-06-18 | 1985-12-27 | Eli Lilly And Company | Aromatase inhibiting N-substituted imidazole derivatives |
| US4609666A (en) | 1984-06-18 | 1986-09-02 | Eli Lilly And Company | Aromatase inhibiting derivatives of α,α-bis(4-halophenyl)methyltetrazoles and triazoles |
| US4902025A (en) | 1987-12-31 | 1990-02-20 | Joseph Albrecht, Bohrfutterfabrik Gmbh & Co. | Self-clamping or self-tightening chuck |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4602025A (en) * | 1984-06-18 | 1986-07-22 | Eli Lilly And Company | Aromatase inhibitors |
| US4659730A (en) * | 1984-06-18 | 1987-04-21 | Eli Lilly And Company | Aromatase inhibiting imidazole derivatives |
| US4801594A (en) * | 1984-06-18 | 1989-01-31 | Eli Lilly And Company | Aromatase inhibitors |
-
1988
- 1988-05-19 NZ NZ224714A patent/NZ224714A/xx unknown
- 1988-05-20 UA UA4355784A patent/UA11192A/uk unknown
- 1988-05-20 RU SU884355784A patent/RU1838308C/ru active
- 1988-05-23 AU AU16537/88A patent/AU603446B2/en not_active Expired
- 1988-05-25 CA CA000567618A patent/CA1307271C/en not_active Expired - Lifetime
- 1988-05-26 DE DE88201061T patent/DE3884055T2/de not_active Expired - Lifetime
- 1988-05-26 ES ES88201061T patent/ES2059490T3/es not_active Expired - Lifetime
- 1988-05-26 EP EP88201061A patent/EP0293978B1/en not_active Expired - Lifetime
- 1988-05-26 CY CY186688A patent/CY1866A/xx unknown
- 1988-05-30 ZA ZA883861A patent/ZA883861B/xx unknown
- 1988-05-30 IL IL86551A patent/IL86551A/xx not_active IP Right Cessation
- 1988-05-31 DK DK198802952A patent/DK175218B1/da not_active IP Right Cessation
- 1988-05-31 FI FI882552A patent/FI90078C/fi not_active IP Right Cessation
- 1988-05-31 NO NO882390A patent/NO169900C/no not_active IP Right Cessation
- 1988-05-31 PT PT87623A patent/PT87623B/pt not_active IP Right Cessation
- 1988-05-31 IE IE164088A patent/IE61823B1/en not_active IP Right Cessation
- 1988-05-31 BG BG084328A patent/BG50278A3/xx unknown
- 1988-06-01 CN CN88103408A patent/CN1022184C/zh not_active Expired - Lifetime
- 1988-06-01 KR KR1019880006557A patent/KR970000952B1/ko not_active Expired - Lifetime
- 1988-06-01 JP JP63132886A patent/JPH0662612B2/ja not_active Expired - Lifetime
- 1988-06-01 HU HU882783A patent/HU201056B/hu unknown
-
1992
- 1992-11-27 LV LVP-92-233A patent/LV10452B/lv unknown
-
1993
- 1993-10-18 BG BG098159A patent/BG60429B2/bg unknown
- 1993-12-16 LT LTIP1625A patent/LT3950B/lt not_active IP Right Cessation
-
1995
- 1995-06-29 HU HU95P/P00533P patent/HU211482A9/hu unknown
- 1995-07-13 HK HK114795A patent/HK114795A/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4410539A (en) | 1980-10-23 | 1983-10-18 | Pfizer Inc. | Heterocyclic thromboxane synthetase inhibitors and pharmaceutical compositions containing them |
| EP0165781A1 (en) | 1984-06-18 | 1985-12-27 | Eli Lilly And Company | Aromatase inhibiting N-substituted imidazole derivatives |
| US4609666A (en) | 1984-06-18 | 1986-09-02 | Eli Lilly And Company | Aromatase inhibiting derivatives of α,α-bis(4-halophenyl)methyltetrazoles and triazoles |
| US4902025A (en) | 1987-12-31 | 1990-02-20 | Joseph Albrecht, Bohrfutterfabrik Gmbh & Co. | Self-clamping or self-tightening chuck |
Non-Patent Citations (3)
| Title |
|---|
| IUPAC-IUB COMM. ON BIOCHEM. NOMENCLATURE: "IUPAC tentative rules for the nomenclature of organic chemistry. Section E. Fundamental stereochemistry", J. ORG. CHEM., 1970, pages 2849 - 2867 |
| J. IAN MASON, BARBARA A. MURRY, MICHAEL OLCOT: "Imidazole antimycotics: Inhibitors of steroid aromatase", BIOCHEMICAL PHARMACOLOGY, 1985, pages 1087, XP023849128, DOI: doi:10.1016/0006-2952(85)90613-6 |
| R.S. CAHN, C.K. INGOLD, V. PRELOG: "Specification of Molecular Chirality", ANGEW. CHEM. INT. ED. ENGL., 1966, pages 385 - 511 |
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Legal Events
| Date | Code | Title | Description |
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| MK9A | Expiry of a patent |
Effective date: 20131216 |