NO752419L

NO752419L -

Info

Publication number: NO752419L
Authority: NO; Norway
Prior art keywords: group; substituted; amino; acid; carboxy
Prior art date: 1974-07-04

Application number

NO75752419A

Other languages

English (en)

Norwegian (no)

Inventor

T Kamiya

Y Saito

M Hashimoto

T Teraji

T Takaya

T Komori

O Nakaguti

T Oku

Y Shiokawa

K Hemmi

H Takasugi

Original Assignee

Fujisawa Pharmaceutical Co

Priority date

1974-07-04

Filing date

1975-07-03

Publication date

1976-01-06

1974-07-04 Priority claimed from JP49077091A external-priority patent/JPS51125061A/ja

1974-07-24 Priority claimed from JP49085526A external-priority patent/JPS51125062A/ja

1974-07-31 Priority claimed from JP49088452A external-priority patent/JPS51125064A/ja

1974-08-30 Priority claimed from JP49100159A external-priority patent/JPS5129476A/ja

1974-09-02 Priority claimed from JP49101712A external-priority patent/JPS5129477A/ja

1974-09-04 Priority claimed from JP49102288A external-priority patent/JPS5129478A/ja

1974-11-26 Priority claimed from JP49136561A external-priority patent/JPS51125065A/ja

1974-11-29 Priority claimed from JP49138137A external-priority patent/JPS51125271A/ja

1974-12-28 Priority claimed from JP751272A external-priority patent/JPS51125272A/ja

1975-02-07 Priority claimed from JP50016584A external-priority patent/JPS5191249A/ja

1975-02-12 Priority claimed from JP50018241A external-priority patent/JPS5195056A/ja

1975-03-12 Priority claimed from JP50030356A external-priority patent/JPS51105052A/ja

1975-03-17 Priority claimed from JP50032703A external-priority patent/JPS51108055A/ja

1975-03-17 Priority claimed from JP50032702A external-priority patent/JPS51108054A/ja

1975-03-18 Priority claimed from JP50033292A external-priority patent/JPS51122058A/ja

1975-03-19 Priority claimed from JP50034830A external-priority patent/JPS51108059A/ja

1975-03-20 Priority claimed from JP50033822A external-priority patent/JPS51108058A/ja

1975-03-20 Priority claimed from JP50033821A external-priority patent/JPS51108057A/ja

1975-07-03 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1976-01-06 Publication of NO752419L publication Critical patent/NO752419L/no

Links

-1 derivatives thereof Chemical group 0.000 claims description 493
150000001875 compounds Chemical class 0.000 claims description 257
239000002253 acid Substances 0.000 claims description 209
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 175
238000000034 method Methods 0.000 claims description 146
125000001424 substituent group Chemical group 0.000 claims description 143
125000003118 aryl group Chemical group 0.000 claims description 124
125000001931 aliphatic group Chemical group 0.000 claims description 113
125000000217 alkyl group Chemical group 0.000 claims description 87
229910052736 halogen Inorganic materials 0.000 claims description 83
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 83
150000002367 halogens Chemical group 0.000 claims description 80
125000002252 acyl group Chemical group 0.000 claims description 73
125000000623 heterocyclic group Chemical group 0.000 claims description 66
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 61
229920006395 saturated elastomer Polymers 0.000 claims description 47
239000001257 hydrogen Substances 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 42
150000003839 salts Chemical group 0.000 claims description 39
229910052799 carbon Inorganic materials 0.000 claims description 38
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
239000003795 chemical substances by application Substances 0.000 claims description 35
125000005236 alkanoylamino group Chemical group 0.000 claims description 33
150000001721 carbon Chemical group 0.000 claims description 32
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 23
125000004442 acylamino group Chemical group 0.000 claims description 22
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 17
125000003710 aryl alkyl group Chemical group 0.000 claims description 15
125000004414 alkyl thio group Chemical group 0.000 claims description 14
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000001183 hydrocarbyl group Chemical group 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 10
239000002168 alkylating agent Substances 0.000 claims description 8
229940100198 alkylating agent Drugs 0.000 claims description 8
125000005239 aroylamino group Chemical group 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 5
238000003776 cleavage reaction Methods 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 1
125000005544 phthalimido group Chemical group 0.000 claims 1
229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 432
239000000243 solution Substances 0.000 description 356
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 252
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 161
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
238000006243 chemical reaction Methods 0.000 description 154
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 151
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 131
239000011541 reaction mixture Substances 0.000 description 121
239000000203 mixture Substances 0.000 description 118
239000002904 solvent Substances 0.000 description 103
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 84
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 80
238000002844 melting Methods 0.000 description 78
230000008018 melting Effects 0.000 description 78
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 77
238000001816 cooling Methods 0.000 description 77
150000001335 aliphatic alkanes Chemical group 0.000 description 67
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 61
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 54
238000000354 decomposition reaction Methods 0.000 description 53
239000000047 product Substances 0.000 description 50
230000002829 reductive effect Effects 0.000 description 49
125000004043 oxo group Chemical group O=* 0.000 description 48
150000002148 esters Chemical class 0.000 description 47
230000008569 process Effects 0.000 description 46
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
239000008346 aqueous phase Substances 0.000 description 42
150000003254 radicals Chemical class 0.000 description 42
238000006722 reduction reaction Methods 0.000 description 41
229910000030 sodium bicarbonate Inorganic materials 0.000 description 39
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
235000017557 sodium bicarbonate Nutrition 0.000 description 38
239000000706 filtrate Substances 0.000 description 37
230000009467 reduction Effects 0.000 description 37
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 36
238000001914 filtration Methods 0.000 description 32
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000007858 starting material Substances 0.000 description 30
125000004432 carbon atom Chemical group C* 0.000 description 29
239000000284 extract Substances 0.000 description 28
125000004356 hydroxy functional group Chemical group O* 0.000 description 28
239000000725 suspension Substances 0.000 description 28
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
239000013078 crystal Substances 0.000 description 26
239000012071 phase Substances 0.000 description 26
239000011135 tin Substances 0.000 description 25
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
238000000862 absorption spectrum Methods 0.000 description 24
239000007864 aqueous solution Substances 0.000 description 23
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
239000003054 catalyst Substances 0.000 description 21
150000002431 hydrogen Chemical class 0.000 description 21
235000011121 sodium hydroxide Nutrition 0.000 description 21
229940083608 sodium hydroxide Drugs 0.000 description 21
238000003756 stirring Methods 0.000 description 21
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
229910052757 nitrogen Chemical group 0.000 description 19
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 18
125000001624 naphthyl group Chemical group 0.000 description 18
239000011780 sodium chloride Substances 0.000 description 18
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 18
239000000843 powder Substances 0.000 description 16
235000011054 acetic acid Nutrition 0.000 description 15
239000002585 base Substances 0.000 description 15
230000000694 effects Effects 0.000 description 15
238000003797 solvolysis reaction Methods 0.000 description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
238000003379 elimination reaction Methods 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
239000003638 chemical reducing agent Substances 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
230000007306 turnover Effects 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229910052783 alkali metal Inorganic materials 0.000 description 12
238000001103 continuous-wave nuclear magnetic resonance spectrum Methods 0.000 description 12
239000005457 ice water Substances 0.000 description 12
239000007788 liquid Substances 0.000 description 12
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
125000006239 protecting group Chemical group 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000011734 sodium Substances 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 11
229910052784 alkaline earth metal Inorganic materials 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
238000005917 acylation reaction Methods 0.000 description 10
125000003342 alkenyl group Chemical group 0.000 description 10
125000005907 alkyl ester group Chemical group 0.000 description 10
125000003277 amino group Chemical group 0.000 description 10
150000003975 aryl alkyl amines Chemical class 0.000 description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
239000000460 chlorine Substances 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
150000007522 mineralic acids Chemical class 0.000 description 10
125000001544 thienyl group Chemical group 0.000 description 10
230000010933 acylation Effects 0.000 description 9
125000001769 aryl amino group Chemical group 0.000 description 9
125000004104 aryloxy group Chemical group 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
238000010531 catalytic reduction reaction Methods 0.000 description 9
229920001429 chelating resin Polymers 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
230000007062 hydrolysis Effects 0.000 description 9
238000006460 hydrolysis reaction Methods 0.000 description 9
150000007529 inorganic bases Chemical class 0.000 description 9
230000000269 nucleophilic effect Effects 0.000 description 9
150000007524 organic acids Chemical class 0.000 description 9
229960003975 potassium Drugs 0.000 description 9
239000011591 potassium Substances 0.000 description 9
229910052700 potassium Inorganic materials 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
229920005989 resin Polymers 0.000 description 9
239000011347 resin Substances 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
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 8
241000588767 Proteus vulgaris Species 0.000 description 8
241000191967 Staphylococcus aureus Species 0.000 description 8
125000003435 aroyl group Chemical group 0.000 description 8
150000001728 carbonyl compounds Chemical class 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
150000007530 organic bases Chemical class 0.000 description 8
229940007042 proteus vulgaris Drugs 0.000 description 8
159000000000 sodium salts Chemical class 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
241000589517 Pseudomonas aeruginosa Species 0.000 description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 7
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
239000001301 oxygen Substances 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
235000011118 potassium hydroxide Nutrition 0.000 description 7
125000004076 pyridyl group Chemical group 0.000 description 7
238000010992 reflux Methods 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
235000017550 sodium carbonate Nutrition 0.000 description 7
239000000126 substance Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
125000002947 alkylene group Chemical group 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
239000011575 calcium Substances 0.000 description 6
229910052791 calcium Inorganic materials 0.000 description 6
125000004663 dialkyl amino group Chemical group 0.000 description 6
238000010828 elution Methods 0.000 description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
239000012452 mother liquor Substances 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
125000000714 pyrimidinyl group Chemical group 0.000 description 6
125000000547 substituted alkyl group Chemical group 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
244000063299 Bacillus subtilis Species 0.000 description 5
235000014469 Bacillus subtilis Nutrition 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
241000588724 Escherichia coli Species 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
150000008065 acid anhydrides Chemical class 0.000 description 5
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
150000001342 alkaline earth metals Chemical class 0.000 description 5
125000000676 alkoxyimino group Chemical group 0.000 description 5
230000000845 anti-microbial effect Effects 0.000 description 5
125000001691 aryl alkyl amino group Chemical group 0.000 description 5
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
229910052742 iron Inorganic materials 0.000 description 5
125000002911 monocyclic heterocycle group Chemical group 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
229910052697 platinum Inorganic materials 0.000 description 5
125000003367 polycyclic group Chemical group 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
238000001179 sorption measurement Methods 0.000 description 5
239000011593 sulfur Chemical group 0.000 description 5
238000005406 washing Methods 0.000 description 5
229910052725 zinc Inorganic materials 0.000 description 5
239000011701 zinc Substances 0.000 description 5
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
241000588722 Escherichia Species 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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