NO851035L

NO851035L - Fremgangsmaate til fremstilling av nye 1,2,4-triazacykloalkaderivater

Fremgangsmaate til fremstilling av nye 1,2,4-triazacykloalkaderivater

Info

Publication number: NO851035L
Authority: NO; Norway
Prior art keywords: lower alkyl; atoms; formula; acid; alkylthio
Prior art date: 1984-03-16

Application number

NO851035A

Other languages

English (en)

Norwegian (no)

Inventor

Knut A Jaeggi

Roland Heckendorn

Original Assignee

Ciba Geigy

Priority date

1984-03-16

Filing date

1985-03-15

Publication date

1985-09-17

1985-03-15 Application filed by Ciba Geigy filed Critical Ciba Geigy

1985-09-17 Publication of NO851035L publication Critical patent/NO851035L/no

Links

238000000034 method Methods 0.000 title claims description 39
238000002360 preparation method Methods 0.000 title claims description 7
-1 carboxy- Chemical class 0.000 claims description 251
125000000217 alkyl group Chemical group 0.000 claims description 210
150000001875 compounds Chemical class 0.000 claims description 96
150000003839 salts Chemical class 0.000 claims description 86
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
125000004432 carbon atom Chemical group C* 0.000 claims description 66
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 62
125000003545 alkoxy group Chemical group 0.000 claims description 59
125000004414 alkyl thio group Chemical group 0.000 claims description 55
125000004043 oxo group Chemical group O=* 0.000 claims description 47
229910052736 halogen Inorganic materials 0.000 claims description 30
125000004423 acyloxy group Chemical group 0.000 claims description 29
150000002367 halogens Chemical class 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 24
125000001931 aliphatic group Chemical group 0.000 claims description 21
125000003396 thiol group Chemical class [H]S* 0.000 claims description 21
125000005530 alkylenedioxy group Chemical group 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
WOECEBYDZBDXMQ-UHFFFAOYSA-N 3-(3-tert-butyl-5-phenyl-1,2,4-triazol-1-yl)pyridine Chemical compound C=1C=CN=CC=1N1N=C(C(C)(C)C)N=C1C1=CC=CC=C1 WOECEBYDZBDXMQ-UHFFFAOYSA-N 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
LVIZDJZOWPJGJD-UHFFFAOYSA-N 3-tert-butyl-1,5-bis(4-methoxyphenyl)-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C(C)(C)C)=NN1C1=CC=C(OC)C=C1 LVIZDJZOWPJGJD-UHFFFAOYSA-N 0.000 claims description 3
241000534944 Thia Species 0.000 claims description 3
125000005237 alkyleneamino group Chemical group 0.000 claims description 3
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
OLGOVVIIQHJTND-UHFFFAOYSA-N 3-(5-tert-butyl-2-phenyl-1,2,4-triazol-3-yl)pyridine Chemical compound C=1C=CC=CC=1N1N=C(C(C)(C)C)N=C1C1=CC=CN=C1 OLGOVVIIQHJTND-UHFFFAOYSA-N 0.000 claims description 2
PTZACPIOZNJNET-UHFFFAOYSA-N 3-(ethylsulfanylmethyl)-1,5-bis(4-methoxyphenyl)-1,2,4-triazole Chemical compound C=1C=C(OC)C=CC=1N1N=C(CSCC)N=C1C1=CC=C(OC)C=C1 PTZACPIOZNJNET-UHFFFAOYSA-N 0.000 claims description 2
GIBHKTJFLHCMJJ-UHFFFAOYSA-N 3-[3-tert-butyl-5-(4-methoxyphenyl)-1,2,4-triazol-1-yl]pyridine Chemical compound COC1=CC=C(C=C1)C1=NC(=NN1C=1C=NC=CC=1)C(C)(C)C GIBHKTJFLHCMJJ-UHFFFAOYSA-N 0.000 claims description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
KKJLDWNXEZCYNT-UHFFFAOYSA-N [1,5-bis(4-methoxyphenyl)-1,2,4-triazol-3-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=NC(CO)=NN1C1=CC=C(OC)C=C1 KKJLDWNXEZCYNT-UHFFFAOYSA-N 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
125000003107 substituted aryl group Chemical group 0.000 claims 1
239000002253 acid Substances 0.000 description 74
235000002639 sodium chloride Nutrition 0.000 description 72
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 52
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
239000003795 chemical substances by application Substances 0.000 description 30
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
239000002585 base Substances 0.000 description 26
150000002148 esters Chemical class 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
150000008064 anhydrides Chemical class 0.000 description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
150000007513 acids Chemical class 0.000 description 18
229910052751 metal Inorganic materials 0.000 description 17
239000002184 metal Substances 0.000 description 17
230000002829 reductive effect Effects 0.000 description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
239000013543 active substance Substances 0.000 description 16
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 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
230000009467 reduction Effects 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
230000002378 acidificating effect Effects 0.000 description 14
229910052783 alkali metal Inorganic materials 0.000 description 14
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 13
229910052784 alkaline earth metal Inorganic materials 0.000 description 13
150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
229910052500 inorganic mineral Inorganic materials 0.000 description 13
235000010755 mineral Nutrition 0.000 description 13
239000011707 mineral Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
235000014113 dietary fatty acids Nutrition 0.000 description 12
239000000194 fatty acid Substances 0.000 description 12
229930195729 fatty acid Natural products 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
150000002430 hydrocarbons Chemical group 0.000 description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
150000001412 amines Chemical class 0.000 description 11
239000012442 inert solvent Substances 0.000 description 11
229920001223 polyethylene glycol Polymers 0.000 description 11
239000007858 starting material Substances 0.000 description 11
239000003826 tablet Substances 0.000 description 11
239000008096 xylene Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
238000007792 addition Methods 0.000 description 10
239000000825 pharmaceutical preparation Substances 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
229910052801 chlorine Inorganic materials 0.000 description 9
125000001841 imino group Chemical group [H]N=* 0.000 description 9
239000012071 phase Substances 0.000 description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
229920002472 Starch Polymers 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 8
238000009835 boiling Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000002904 solvent Substances 0.000 description 8
235000019698 starch Nutrition 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
239000013078 crystal Substances 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
230000007062 hydrolysis Effects 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 7
230000001590 oxidative effect Effects 0.000 description 7
235000011007 phosphoric acid Nutrition 0.000 description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
235000010288 sodium nitrite Nutrition 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
239000000454 talc Substances 0.000 description 7
229910052623 talc Inorganic materials 0.000 description 7
235000012222 talc Nutrition 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 6
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
239000002202 Polyethylene glycol Substances 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 6
239000003513 alkali Substances 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
150000001342 alkaline earth metals Chemical class 0.000 description 6
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
238000001816 cooling Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
235000011187 glycerol Nutrition 0.000 description 6
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
239000008101 lactose Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000008107 starch Substances 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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
150000001335 aliphatic alkanes Chemical class 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000004305 biphenyl Substances 0.000 description 5
235000010290 biphenyl Nutrition 0.000 description 5
125000006267 biphenyl group Chemical group 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
239000008298 dragée Substances 0.000 description 5
150000002191 fatty alcohols Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000002674 ointment Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
230000007017 scission Effects 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000000600 sorbitol Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
OCTBILKUFVVQMV-UHFFFAOYSA-N 3-(chloromethyl)-1,5-bis(4-methoxyphenyl)-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C1=NC(CCl)=NN1C1=CC=C(OC)C=C1 OCTBILKUFVVQMV-UHFFFAOYSA-N 0.000 description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000002841 Lewis acid Substances 0.000 description 4
239000005662 Paraffin oil Substances 0.000 description 4
229920000180 alkyd Polymers 0.000 description 4
150000003973 alkyl amines Chemical class 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
229910052793 cadmium Inorganic materials 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
229960000541 cetyl alcohol Drugs 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
239000006071 cream Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
239000013067 intermediate product Substances 0.000 description 4
229910052742 iron Inorganic materials 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
150000007517 lewis acids Chemical class 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
229910052749 magnesium Inorganic materials 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229910052987 metal hydride Inorganic materials 0.000 description 4
150000004681 metal hydrides Chemical class 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
150000005846 sugar alcohols Polymers 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
239000011701 zinc Substances 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
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SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
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229910052748 manganese Inorganic materials 0.000 description 2
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NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
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230000000144 pharmacologic effect Effects 0.000 description 2
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DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
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AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
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VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
PVRSIFAEUCUJPK-UHFFFAOYSA-N (4-methoxyphenyl)hydrazine Chemical compound COC1=CC=C(NN)C=C1 PVRSIFAEUCUJPK-UHFFFAOYSA-N 0.000 description 1
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