NO174509B - Analogifremgangsmaate for fremstilling av terapeutisk aktive (1H-azol- 1-ylmetyl)substituerte kinolin-, kinazolin- eller kinoksazolinderivater - Google Patents

Info

Publication number

NO174509B

NO174509B NO894734A NO894734A NO174509B NO 174509 B NO174509 B NO 174509B NO 894734 A NO894734 A NO 894734A NO 894734 A NO894734 A NO 894734A NO 174509 B NO174509 B NO 174509B

Authority

NO

Norway

Prior art keywords

formula

parts

alkyl

residue

compounds

Prior art date

1988-11-29

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• -1 1H-Azol-1-ylmethyl Chemical group 0.000 title claims abstract description 58
• 238000000034 method Methods 0.000 title claims abstract description 32
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical class N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title claims abstract description 7
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims description 13
• 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 264
• 239000001257 hydrogen Substances 0.000 claims abstract description 124
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 124
• 239000002253 acid Substances 0.000 claims abstract description 32
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 30
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
• 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 claims abstract description 10
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 100
• 238000003756 stirring Methods 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• 150000002431 hydrogen Chemical group 0.000 claims description 60
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
• 238000006243 chemical reaction Methods 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 239000002904 solvent Substances 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
• 238000007363 ring formation reaction Methods 0.000 claims description 21
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000002883 imidazolyl group Chemical group 0.000 claims description 15
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
• 239000003054 catalyst Substances 0.000 claims description 14
• 238000009833 condensation Methods 0.000 claims description 13
• 230000005494 condensation Effects 0.000 claims description 13
• 239000012442 inert solvent Substances 0.000 claims description 12
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 11
• 125000001544 thienyl group Chemical group 0.000 claims description 11
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 239000003638 chemical reducing agent Substances 0.000 claims description 8
• 239000003513 alkali Substances 0.000 claims description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
• 229910052783 alkali metal Inorganic materials 0.000 claims description 6
• 229910021529 ammonia Inorganic materials 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 6
• 229930185107 quinolinone Natural products 0.000 claims description 6
• 238000006798 ring closing metathesis reaction Methods 0.000 claims description 6
• 238000007126 N-alkylation reaction Methods 0.000 claims description 5
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 4
• 230000003213 activating effect Effects 0.000 claims description 4
• 150000004716 alpha keto acids Chemical class 0.000 claims description 4
• 229910052751 metal Inorganic materials 0.000 claims description 4
• 239000002184 metal Substances 0.000 claims description 4
• 230000009467 reduction Effects 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 150000001412 amines Chemical class 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 3
• 239000012458 free base Substances 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 230000002140 halogenating effect Effects 0.000 claims description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 235000006408 oxalic acid Nutrition 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• 230000007306 turnover Effects 0.000 claims description 2
• 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• 230000004069 differentiation Effects 0.000 abstract description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 3
• 230000035755 proliferation Effects 0.000 abstract description 3
• 230000002159 abnormal effect Effects 0.000 abstract description 2
• 210000000981 epithelium Anatomy 0.000 abstract description 2
• 239000008194 pharmaceutical composition Substances 0.000 abstract 2
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
• 239000004480 active ingredient Substances 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 303
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 294
• 239000000543 intermediate Substances 0.000 description 176
• 239000000203 mixture Substances 0.000 description 125
• 239000000047 product Substances 0.000 description 114
• 239000000243 solution Substances 0.000 description 104
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
• 238000002844 melting Methods 0.000 description 101
• 230000008018 melting Effects 0.000 description 101
• 239000011541 reaction mixture Substances 0.000 description 91
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
• 239000003480 eluent Substances 0.000 description 85
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 72
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
• 239000000741 silica gel Substances 0.000 description 66
• 229910002027 silica gel Inorganic materials 0.000 description 66
• 238000004440 column chromatography Methods 0.000 description 61
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
• 239000000284 extract Substances 0.000 description 50
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 238000010992 reflux Methods 0.000 description 42
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• 235000019441 ethanol Nutrition 0.000 description 38
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 36
• 229930002330 retinoic acid Natural products 0.000 description 36
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 35
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 33
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 29
• 229960001701 chloroform Drugs 0.000 description 27
• 239000000706 filtrate Substances 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• 239000013067 intermediate product Substances 0.000 description 17
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
• 238000001816 cooling Methods 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
• 239000005457 ice water Substances 0.000 description 14
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 12
• 239000008280 blood Substances 0.000 description 12
• 210000004369 blood Anatomy 0.000 description 12
• LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
• 239000012279 sodium borohydride Substances 0.000 description 12
• 229910000033 sodium borohydride Inorganic materials 0.000 description 12
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 125000005059 halophenyl group Chemical group 0.000 description 11
• 229960004592 isopropanol Drugs 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• 229960001727 tretinoin Drugs 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• 241001465754 Metazoa Species 0.000 description 9
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
• 239000003098 androgen Substances 0.000 description 9
• 238000004128 high performance liquid chromatography Methods 0.000 description 9
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 9
• 230000004060 metabolic process Effects 0.000 description 9
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
• QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 235000011114 ammonium hydroxide Nutrition 0.000 description 8
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
• 238000001704 evaporation Methods 0.000 description 8
• 230000008020 evaporation Effects 0.000 description 8
• 150000008282 halocarbons Chemical class 0.000 description 8
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
• 230000000144 pharmacologic effect Effects 0.000 description 8
• SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 8
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
• 239000007868 Raney catalyst Substances 0.000 description 7
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
• 229910000564 Raney nickel Inorganic materials 0.000 description 7
• 241000700159 Rattus Species 0.000 description 7
• 239000002585 base Substances 0.000 description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
• 238000011084 recovery Methods 0.000 description 7
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 6
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 6
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 6
• 239000005909 Kieselgur Substances 0.000 description 6
• 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 6
• 241000700157 Rattus norvegicus Species 0.000 description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
• 229940011871 estrogen Drugs 0.000 description 6
• 239000000262 estrogen Substances 0.000 description 6
• 229960002897 heparin Drugs 0.000 description 6
• 229920000669 heparin Polymers 0.000 description 6
• 230000010354 integration Effects 0.000 description 6
• 230000036470 plasma concentration Effects 0.000 description 6
• 238000011002 quantification Methods 0.000 description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
• 238000000825 ultraviolet detection Methods 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 239000000908 ammonium hydroxide Substances 0.000 description 5
• 230000037396 body weight Effects 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 229950005499 carbon tetrachloride Drugs 0.000 description 5
• 239000000460 chlorine Substances 0.000 description 5
• 230000007812 deficiency Effects 0.000 description 5
• MGSWAHQQBHNCEI-UHFFFAOYSA-N ethyl 4-methyl-2-oxopentanoate Chemical compound CCOC(=O)C(=O)CC(C)C MGSWAHQQBHNCEI-UHFFFAOYSA-N 0.000 description 5
• 239000010410 layer Substances 0.000 description 5
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
• 239000000376 reactant Substances 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 239000012258 stirred mixture Substances 0.000 description 5
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
• 229930192474 thiophene Natural products 0.000 description 5
• KDVFRMMRZOCFLS-UHFFFAOYSA-N 2-oxopentanoic acid Chemical compound CCCC(=O)C(O)=O KDVFRMMRZOCFLS-UHFFFAOYSA-N 0.000 description 4
• HNPKZIDUJAFHKE-UHFFFAOYSA-N 4-(imidazol-1-ylmethyl)benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1CN1C=NC=C1 HNPKZIDUJAFHKE-UHFFFAOYSA-N 0.000 description 4
• GGUIKTLTNIMAHY-UHFFFAOYSA-N 4-[(3-chlorophenyl)-imidazol-1-ylmethyl]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1C(N1C=NC=C1)C1=CC=CC(Cl)=C1 GGUIKTLTNIMAHY-UHFFFAOYSA-N 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• 150000001204 N-oxides Chemical class 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 229940030486 androgens Drugs 0.000 description 4
• 239000000010 aprotic solvent Substances 0.000 description 4
• 238000010533 azeotropic distillation Methods 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 229910052799 carbon Inorganic materials 0.000 description 4
• 210000004027 cell Anatomy 0.000 description 4
• 239000012141 concentrate Substances 0.000 description 4
• 238000002425 crystallisation Methods 0.000 description 4
• 230000008025 crystallization Effects 0.000 description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• 238000004821 distillation Methods 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 238000002474 experimental method Methods 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
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