CA1097638A - Imidazo-as-triazine derivatives - Google Patents

Imidazo-as-triazine derivatives

Info

Publication number: CA1097638A
Authority: CA; Canada
Prior art keywords: methyl; triazin; imidazo; propyl; phenyl
Prior art date: 1977-02-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA296,027A

Other languages

English (en)

French (fr)

Inventor

Rolf Paul

Judith Menschik

Bryant L. Walworth

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-02-03

Filing date

1978-02-02

Publication date

1981-03-17

1977-10-18 Priority claimed from US05/843,174 external-priority patent/US4107307A/en

1977-11-07 Priority claimed from US05/848,836 external-priority patent/US4124766A/en

1978-02-02 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1981-03-17 Application granted granted Critical

1981-03-17 Publication of CA1097638A publication Critical patent/CA1097638A/en

Status Expired legal-status Critical Current

Links

AIMBMQACKYCWKB-UHFFFAOYSA-N 7h-imidazo[4,5-e][1,2,4]triazine Chemical class C1=NN=C2NC=NC2=N1 AIMBMQACKYCWKB-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 115
238000000034 method Methods 0.000 claims abstract description 113
230000008569 process Effects 0.000 claims abstract description 60
239000001257 hydrogen Substances 0.000 claims abstract description 43
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
-1 bromo, chloro, iodo Chemical group 0.000 claims abstract description 36
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
239000001301 oxygen Substances 0.000 claims abstract description 14
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical group 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
239000011593 sulfur Substances 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract description 4
125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 30
239000000126 substance Substances 0.000 claims description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
239000003960 organic solvent Substances 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
238000010992 reflux Methods 0.000 claims description 12
150000004702 methyl esters Chemical class 0.000 claims description 11
238000009835 boiling Methods 0.000 claims description 9
238000010438 heat treatment Methods 0.000 claims description 9
239000012442 inert solvent Substances 0.000 claims description 9
WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 claims description 8
MBPOEUWFBVJHPT-UHFFFAOYSA-N 6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound N12C(=O)NN=CC2=CN=C1C1=CC=CC=C1 MBPOEUWFBVJHPT-UHFFFAOYSA-N 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
OUYFNJMMIHHXCE-UHFFFAOYSA-N 8-methyl-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(C)N=C2C1=CC=CC=C1 OUYFNJMMIHHXCE-UHFFFAOYSA-N 0.000 claims description 6
230000002152 alkylating effect Effects 0.000 claims description 5
239000007789 gas Substances 0.000 claims description 5
CLAYGDBKHGPTDC-UHFFFAOYSA-N 6-propyl-3h-imidazo[1,5-d][1,2,4]triazine-4-thione Chemical compound C1=NNC(=S)N2C(CCC)=NC=C21 CLAYGDBKHGPTDC-UHFFFAOYSA-N 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 4
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 4
WSLHABVSCHEJPP-UHFFFAOYSA-N 6,8-dibromo-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(Br)N=C2Br WSLHABVSCHEJPP-UHFFFAOYSA-N 0.000 claims description 3
GPQDFZOLGWYHJU-UHFFFAOYSA-N 8-bromo-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(Br)N=C2C1=CC=CC=C1 GPQDFZOLGWYHJU-UHFFFAOYSA-N 0.000 claims description 3
KGJOHYXBJQXCCC-UHFFFAOYSA-N 8-chloro-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(Cl)N=C2C1=CC=CC=C1 KGJOHYXBJQXCCC-UHFFFAOYSA-N 0.000 claims description 3
MOWCUJJAWXTYQL-UHFFFAOYSA-N 8-iodo-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(I)N=C2C1=CC=CC=C1 MOWCUJJAWXTYQL-UHFFFAOYSA-N 0.000 claims description 3
BDOAATXZVMJJTJ-UHFFFAOYSA-N 8-methyl-6-propyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NN=C(O)N2C(CCC)=NC(C)=C21 BDOAATXZVMJJTJ-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
HGFVSHZVVFIGRO-UHFFFAOYSA-N ethyl N-[(2-tert-butyl-5-methyl-1H-imidazol-4-yl)methylideneamino]carbamate Chemical compound CCOC(=O)NN=CC=1N=C(C(C)(C)C)NC=1C HGFVSHZVVFIGRO-UHFFFAOYSA-N 0.000 claims description 3
230000026030 halogenation Effects 0.000 claims description 3
238000005658 halogenation reaction Methods 0.000 claims description 3
238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
125000001118 alkylidene group Chemical group 0.000 claims description 2
HZBWRBNRGXTDCJ-UHFFFAOYSA-N ethyl N-[(2,5-dimethyl-1H-imidazol-4-yl)methylideneamino]carbamate Chemical compound CCOC(=O)NN=CC=1N=C(C)NC=1C HZBWRBNRGXTDCJ-UHFFFAOYSA-N 0.000 claims description 2
AVBGZJLTQXJYDU-UHFFFAOYSA-N ethyl N-[(2-phenyl-1H-imidazol-5-yl)methylideneamino]carbamate Chemical compound CCOC(=O)NN=CC1=CNC(C=2C=CC=CC=2)=N1 AVBGZJLTQXJYDU-UHFFFAOYSA-N 0.000 claims description 2
ZTNOMVZYHVGGFI-UHFFFAOYSA-N ethyl N-[(2-propyl-1H-imidazol-5-yl)methylideneamino]carbamate Chemical compound CCCC1=NC(C=NNC(=O)OCC)=CN1 ZTNOMVZYHVGGFI-UHFFFAOYSA-N 0.000 claims description 2
JRXYWLUSAMGKJG-UHFFFAOYSA-N ethyl N-[(5-methyl-1H-imidazol-4-yl)methylideneamino]carbamate Chemical compound CCOC(=O)NN=CC=1N=CNC=1C JRXYWLUSAMGKJG-UHFFFAOYSA-N 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
ZERHGAZTVAVLAD-UHFFFAOYSA-N methyl N-[(2-propyl-1H-imidazol-5-yl)methylideneamino]carbamodithioate Chemical compound CCCC1=NC(C=NNC(=S)SC)=CN1 ZERHGAZTVAVLAD-UHFFFAOYSA-N 0.000 claims description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 11
PQQJTBGWBNXLAY-UHFFFAOYSA-N 1,8-dimethyl-6-propyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound CC1=NNC(=O)N2C(CCC)=NC(C)=C21 PQQJTBGWBNXLAY-UHFFFAOYSA-N 0.000 claims 2
ONHKIFLLHVZOSM-UHFFFAOYSA-N 1-ethyl-8-methyl-6-propyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound CCC1=NNC(=O)N2C(CCC)=NC(C)=C21 ONHKIFLLHVZOSM-UHFFFAOYSA-N 0.000 claims 2
RAVTZAAADOSHAN-UHFFFAOYSA-N 6,8-dimethyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(C)N=C2C RAVTZAAADOSHAN-UHFFFAOYSA-N 0.000 claims 2
LQRXOPUSPXNDAD-UHFFFAOYSA-N 6-(3-aminophenyl)-8-bromo-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound NC1=CC=CC(C=2N3C(=O)NN=CC3=C(Br)N=2)=C1 LQRXOPUSPXNDAD-UHFFFAOYSA-N 0.000 claims 2
ZPNYDJXZRNCPTH-UHFFFAOYSA-N 6-(3-nitrophenyl)-3H-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound [N+](=O)([O-])C=1C=C(C=CC1)C1=NC=C2N1C(NN=C2)=O ZPNYDJXZRNCPTH-UHFFFAOYSA-N 0.000 claims 2
MJZMWJIXBDMSQB-UHFFFAOYSA-N 6-cyclopropyl-3H-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1(CC1)C1=NC=C2N1C(NN=C2)=O MJZMWJIXBDMSQB-UHFFFAOYSA-N 0.000 claims 2
KQVMFGBJLFULLY-UHFFFAOYSA-N 6-propyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C(CCC)=NC=C21 KQVMFGBJLFULLY-UHFFFAOYSA-N 0.000 claims 2
BMCUHHKYFQFPEF-UHFFFAOYSA-N 6-tert-butyl-8-methyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(C)N=C2C(C)(C)C BMCUHHKYFQFPEF-UHFFFAOYSA-N 0.000 claims 2
GYRNWWWCIUGQRS-UHFFFAOYSA-N 8-methyl-1,6-dipropyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound CCCC1=NN=C(O)N2C(CCC)=NC(C)=C21 GYRNWWWCIUGQRS-UHFFFAOYSA-N 0.000 claims 2
GBQQIMAKWFXDDK-UHFFFAOYSA-N 8-methyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(C)N=C2 GBQQIMAKWFXDDK-UHFFFAOYSA-N 0.000 claims 2
DKBLIXBFYPMVIH-UHFFFAOYSA-N 8-methyl-6-phenyl-3-prop-2-ynylimidazo[1,5-d][1,2,4]triazin-4-one Chemical compound CC=1N=C(N2C(N(N=CC21)CC#C)=O)C2=CC=CC=C2 DKBLIXBFYPMVIH-UHFFFAOYSA-N 0.000 claims 2
125000005907 alkyl ester group Chemical group 0.000 claims 2
WGCICQJXVYFFCA-UHFFFAOYSA-N 3-iodoprop-1-yne Chemical compound ICC#C WGCICQJXVYFFCA-UHFFFAOYSA-N 0.000 claims 1
MTVARWNWRVCNNE-UHFFFAOYSA-N 8-methyl-3h-imidazo[1,5-d][1,2,4]triazine-4-thione Chemical compound C1=NNC(=S)N2C1=C(C)N=C2 MTVARWNWRVCNNE-UHFFFAOYSA-N 0.000 claims 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 1
YTFVYNGKHPDOLB-UHFFFAOYSA-N ethyl N-[(5-methyl-2-phenyl-1H-imidazol-4-yl)methylideneamino]carbamate Chemical compound N1C(C)=C(C=NNC(=O)OCC)N=C1C1=CC=CC=C1 YTFVYNGKHPDOLB-UHFFFAOYSA-N 0.000 claims 1
SUOLNUSOEGLZLR-UHFFFAOYSA-N ethyl N-[(5-methyl-2-propyl-1H-imidazol-4-yl)methylideneamino]carbamate Chemical compound CCCC1=NC(C=NNC(=O)OCC)=C(C)N1 SUOLNUSOEGLZLR-UHFFFAOYSA-N 0.000 claims 1
NRZHXHPKQBXFLP-UHFFFAOYSA-N methyl N-[(5-methyl-1H-imidazol-4-yl)methylideneamino]carbamodithioate Chemical compound CSC(=S)NN=CC=1N=CNC=1C NRZHXHPKQBXFLP-UHFFFAOYSA-N 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
229940095074 cyclic amp Drugs 0.000 abstract description 17
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 11
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 11
150000002431 hydrogen Chemical group 0.000 abstract description 11
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 7
102000004190 Enzymes Human genes 0.000 abstract description 6
108090000790 Enzymes Proteins 0.000 abstract description 6
230000002401 inhibitory effect Effects 0.000 abstract description 2
150000002894 organic compounds Chemical class 0.000 abstract description 2
ONOJCVBIBBEBGK-UHFFFAOYSA-N 3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical class OC1=NN=CC2=CN=CN12 ONOJCVBIBBEBGK-UHFFFAOYSA-N 0.000 abstract 1
241001061127 Thione Species 0.000 abstract 1
239000000203 mixture Substances 0.000 description 105
239000000047 product Substances 0.000 description 96
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
239000007787 solid Substances 0.000 description 62
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
239000000243 solution Substances 0.000 description 43
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 41
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
239000002253 acid Substances 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 25
235000019441 ethanol Nutrition 0.000 description 24
229960004756 ethanol Drugs 0.000 description 23
238000004458 analytical method Methods 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
150000002148 esters Chemical class 0.000 description 18
238000012360 testing method Methods 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
235000013350 formula milk Nutrition 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
229940022682 acetone Drugs 0.000 description 13
239000013078 crystal Substances 0.000 description 13
241000196324 Embryophyta Species 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000001914 filtration Methods 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
QDYTUZCWBJRHKK-UHFFFAOYSA-N imidazole-4-methanol Chemical compound OCC1=CNC=N1 QDYTUZCWBJRHKK-UHFFFAOYSA-N 0.000 description 10
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
239000000872 buffer Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000011347 resin Substances 0.000 description 9
229920005989 resin Polymers 0.000 description 9
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
150000002576 ketones Chemical class 0.000 description 8
239000000463 material Substances 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
235000017550 sodium carbonate Nutrition 0.000 description 8
239000000725 suspension Substances 0.000 description 8
238000001816 cooling Methods 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
229910017604 nitric acid Inorganic materials 0.000 description 7
239000003921 oil Substances 0.000 description 7
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 6
238000003556 assay Methods 0.000 description 6
229940076134 benzene Drugs 0.000 description 6
239000008120 corn starch Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
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 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
239000003610 charcoal Substances 0.000 description 5
230000005484 gravity Effects 0.000 description 5
229960004592 isopropanol Drugs 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
235000015424 sodium Nutrition 0.000 description 5
229940083542 sodium Drugs 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
LFKJFIOTRHYONM-UHFFFAOYSA-N 2-phenyl-1h-imidazole-5-carbaldehyde Chemical compound N1C(C=O)=CN=C1C1=CC=CC=C1 LFKJFIOTRHYONM-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
YNNGZCVDIREDDK-UHFFFAOYSA-N aminocarbamodithioic acid Chemical class NNC(S)=S YNNGZCVDIREDDK-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 4
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 4
238000009472 formulation Methods 0.000 description 4
230000002363 herbicidal effect Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000010410 layer Substances 0.000 description 4
210000004072 lung Anatomy 0.000 description 4
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000006228 supernatant Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
239000006188 syrup Substances 0.000 description 4
ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 description 3
QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000282693 Cercopithecidae Species 0.000 description 3
239000004338 Dichlorodifluoromethane Substances 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
244000309464 bull Species 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
239000008187 granular material Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
WOSLIVMIANGCOW-UHFFFAOYSA-N imidazo[4,5-e][1,2,4]triazin-3-one Chemical group O=C1N=NC2=NC=NC2=N1 WOSLIVMIANGCOW-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ZJPCLNLMECIJKX-UHFFFAOYSA-N (2,5-dimethyl-1h-imidazol-4-yl)methanol Chemical compound CC1=NC(C)=C(CO)N1 ZJPCLNLMECIJKX-UHFFFAOYSA-N 0.000 description 2
XMKYXMNRMGDDGL-UHFFFAOYSA-N (2-benzyl-1h-imidazol-5-yl)methanol Chemical compound OCC1=CNC(CC=2C=CC=CC=2)=N1 XMKYXMNRMGDDGL-UHFFFAOYSA-N 0.000 description 2
UPXKPKGRBQIARE-UHFFFAOYSA-N (2-tert-butyl-1h-imidazol-5-yl)methanol Chemical compound CC(C)(C)C1=NC(CO)=CN1 UPXKPKGRBQIARE-UHFFFAOYSA-N 0.000 description 2
SQQVWKXBKXSCEC-UHFFFAOYSA-N (2-tert-butyl-5-methyl-1h-imidazol-4-yl)methanol Chemical compound CC=1NC(C(C)(C)C)=NC=1CO SQQVWKXBKXSCEC-UHFFFAOYSA-N 0.000 description 2
RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 2
PTHGVOCFAZSNNA-UHFFFAOYSA-N 2-butyl-1h-imidazole-5-carbaldehyde Chemical compound CCCCC1=NC=C(C=O)N1 PTHGVOCFAZSNNA-UHFFFAOYSA-N 0.000 description 2
ZWULFIBGPXWGFG-UHFFFAOYSA-N 2-methyl-1h-imidazole-5-carbaldehyde Chemical compound CC1=NC=C(C=O)N1 ZWULFIBGPXWGFG-UHFFFAOYSA-N 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
RJJUHCRCATVRBK-UHFFFAOYSA-N 2-propyl-1h-imidazole-5-carbaldehyde Chemical compound CCCC1=NC=C(C=O)N1 RJJUHCRCATVRBK-UHFFFAOYSA-N 0.000 description 2
BSGNHGCLZZKFNY-UHFFFAOYSA-N 2-tert-butyl-1h-imidazole-5-carbaldehyde Chemical compound CC(C)(C)C1=NC(C=O)=CN1 BSGNHGCLZZKFNY-UHFFFAOYSA-N 0.000 description 2
IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 2
KMWCSNCNHSEXIF-UHFFFAOYSA-N 5-methyl-1h-imidazole-4-carbaldehyde Chemical compound CC=1N=CNC=1C=O KMWCSNCNHSEXIF-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
241000167854 Bourreria succulenta Species 0.000 description 2
244000056139 Brassica cretica Species 0.000 description 2
235000003351 Brassica cretica Nutrition 0.000 description 2
235000003343 Brassica rupestris Nutrition 0.000 description 2
240000006122 Chenopodium album Species 0.000 description 2
235000009344 Chenopodium album Nutrition 0.000 description 2
244000058871 Echinochloa crus-galli Species 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
240000003461 Setaria viridis Species 0.000 description 2
235000002248 Setaria viridis Nutrition 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
239000004147 Sorbitan trioleate Substances 0.000 description 2
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
DJUJEXMLAMEFDS-UHFFFAOYSA-N [2-(2-propoxyphenyl)-1h-imidazol-5-yl]methanol Chemical compound CCCOC1=CC=CC=C1C1=NC(CO)=CN1 DJUJEXMLAMEFDS-UHFFFAOYSA-N 0.000 description 2
GCBSRPOGGYIYGZ-UHFFFAOYSA-N [2-(methoxymethyl)-1h-imidazol-5-yl]methanol Chemical compound COCC1=NC(CO)=CN1 GCBSRPOGGYIYGZ-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
STYCVEYASXULRN-UHFFFAOYSA-N butanimidamide;hydrochloride Chemical compound [Cl-].CCCC(N)=[NH2+] STYCVEYASXULRN-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000019693 cherries Nutrition 0.000 description 2
239000007958 cherry flavor Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000012154 double-distilled water Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
230000009969 flowable effect Effects 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
238000000227 grinding Methods 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
230000036244 malformation Effects 0.000 description 2
RQPIIWWJAUAQKF-UHFFFAOYSA-N methyl 2,2-dimethylpropanimidate;hydrochloride Chemical compound Cl.COC(=N)C(C)(C)C RQPIIWWJAUAQKF-UHFFFAOYSA-N 0.000 description 2
NRVFREDCSTUHLY-UHFFFAOYSA-N methyl N-[(2-phenyl-1H-imidazol-5-yl)methylideneamino]carbamodithioate Chemical compound CSC(=S)NN=CC1=CNC(C=2C=CC=CC=2)=N1 NRVFREDCSTUHLY-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
235000010460 mustard Nutrition 0.000 description 2
OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
229910052625 palygorskite Inorganic materials 0.000 description 2
239000003182 parenteral nutrition solution Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000001902 propagating effect Effects 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
229940081974 saccharin Drugs 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
235000010234 sodium benzoate Nutrition 0.000 description 2
239000004299 sodium benzoate Substances 0.000 description 2
229960003885 sodium benzoate Drugs 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
235000019337 sorbitan trioleate Nutrition 0.000 description 2
229960000391 sorbitan trioleate Drugs 0.000 description 2
238000003860 storage Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
230000009974 thixotropic effect Effects 0.000 description 2
231100000167 toxic agent Toxicity 0.000 description 2
239000003440 toxic substance Substances 0.000 description 2
238000010792 warming Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
RNWHYZRESQFIPX-UHFFFAOYSA-N (2-benzyl-5-methyl-1h-imidazol-4-yl)methanol Chemical compound N1C(CO)=C(C)N=C1CC1=CC=CC=C1 RNWHYZRESQFIPX-UHFFFAOYSA-N 0.000 description 1
MQRMTENGXFRETM-UHFFFAOYSA-N (2-methyl-1h-imidazol-5-yl)methanol Chemical compound CC1=NC=C(CO)N1 MQRMTENGXFRETM-UHFFFAOYSA-N 0.000 description 1
GGRBEFVMJHQWFG-UHFFFAOYSA-N (2-phenyl-1h-imidazol-5-yl)methanol Chemical compound OCC1=CNC(C=2C=CC=CC=2)=N1 GGRBEFVMJHQWFG-UHFFFAOYSA-N 0.000 description 1
IIUFTJVORFTWDC-UWVGGRQHSA-N (4S,5S)-4,5-dimethyl-2-(3-methylphenyl)-4,5-dihydro-1H-imidazole Chemical compound C[C@@H]1N=C(N[C@H]1C)C=1C=C(C=CC1)C IIUFTJVORFTWDC-UWVGGRQHSA-N 0.000 description 1
YWKSINPSASCIMZ-WHFBIAKZSA-N (4s,5s)-4,5-dimethyl-4,5-dihydro-1h-imidazole Chemical compound C[C@@H]1NC=N[C@H]1C YWKSINPSASCIMZ-WHFBIAKZSA-N 0.000 description 1
AXJZCJSXNZZMDU-UHFFFAOYSA-N (5-methyl-1h-imidazol-4-yl)methanol Chemical compound CC=1N=CNC=1CO AXJZCJSXNZZMDU-UHFFFAOYSA-N 0.000 description 1
RZHVENCMBIPGNJ-UHFFFAOYSA-N (5-methyl-2-propyl-1h-imidazol-4-yl)methanol Chemical compound CCCC1=NC(CO)=C(C)N1 RZHVENCMBIPGNJ-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
JLLNQGHQFQJAKQ-UHFFFAOYSA-N 1,3-dihydroxyimidazolidine Chemical compound ON1CCN(O)C1 JLLNQGHQFQJAKQ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
ZOMATQMEHRJKLO-UHFFFAOYSA-N 1h-imidazol-2-ylmethanol Chemical class OCC1=NC=CN1 ZOMATQMEHRJKLO-UHFFFAOYSA-N 0.000 description 1
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
ARDGQYVTLGUJII-UHFFFAOYSA-N 2,2-dimethylpropanimidamide;hydrochloride Chemical compound Cl.CC(C)(C)C(N)=N ARDGQYVTLGUJII-UHFFFAOYSA-N 0.000 description 1
MFFWADYNIVRMMM-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole-4-carbaldehyde Chemical compound CC1=NC(C=O)=C(C)N1 MFFWADYNIVRMMM-UHFFFAOYSA-N 0.000 description 1
ZKPDACHGKIGSJV-UHFFFAOYSA-N 2-benzyl-1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC(CC=2C=CC=CC=2)=N1 ZKPDACHGKIGSJV-UHFFFAOYSA-N 0.000 description 1
URODTOQIGNUZCY-UHFFFAOYSA-N 2-benzyl-5-methyl-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(C)NC(CC=2C=CC=CC=2)=N1 URODTOQIGNUZCY-UHFFFAOYSA-N 0.000 description 1
JKEYQFINLZPTNK-UHFFFAOYSA-N 2-benzyl-5-propyl-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(CCC)NC(CC=2C=CC=CC=2)=N1 JKEYQFINLZPTNK-UHFFFAOYSA-N 0.000 description 1
UETFVEJXNHDCPU-UHFFFAOYSA-N 2-tert-butyl-5-methyl-1h-imidazole-4-carbaldehyde Chemical compound CC=1NC(C(C)(C)C)=NC=1C=O UETFVEJXNHDCPU-UHFFFAOYSA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 1
102000004008 5'-Nucleotidase Human genes 0.000 description 1
XVWOWPZGRZBDLS-UHFFFAOYSA-N 5-(dimethoxymethyl)-2-phenyl-1h-imidazole Chemical compound N1C(C(OC)OC)=CN=C1C1=CC=CC=C1 XVWOWPZGRZBDLS-UHFFFAOYSA-N 0.000 description 1
QALCPTMLNVUKMD-UHFFFAOYSA-N 5-(dimethoxymethyl)-4-iodo-2-phenyl-1h-imidazole Chemical compound IC1=C(C(OC)OC)NC(C=2C=CC=CC=2)=N1 QALCPTMLNVUKMD-UHFFFAOYSA-N 0.000 description 1
GVWNPRUANAXMAA-UHFFFAOYSA-N 5-ethyl-2-phenyl-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(CC)NC(C=2C=CC=CC=2)=N1 GVWNPRUANAXMAA-UHFFFAOYSA-N 0.000 description 1
SPNRJKKWXOGXKU-UHFFFAOYSA-N 5-iodo-2-phenyl-1h-imidazole-4-carbaldehyde Chemical compound N1C(C=O)=C(I)N=C1C1=CC=CC=C1 SPNRJKKWXOGXKU-UHFFFAOYSA-N 0.000 description 1
SHEJHKQCPUPVHA-UHFFFAOYSA-N 5-methyl-2-(3-methylphenyl)-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(C)NC(C=2C=C(C)C=CC=2)=N1 SHEJHKQCPUPVHA-UHFFFAOYSA-N 0.000 description 1
VIKGPHOEADGPIA-UHFFFAOYSA-N 5-methyl-2-(4-nitrophenyl)-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(C)NC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 VIKGPHOEADGPIA-UHFFFAOYSA-N 0.000 description 1
KFVGBCOFGJKBPM-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(C)NC(C=2C=CC=CC=2)=N1 KFVGBCOFGJKBPM-UHFFFAOYSA-N 0.000 description 1
CHUGUCQQTLHMKZ-UHFFFAOYSA-N 5-methyl-2-propyl-1h-imidazole-4-carbaldehyde Chemical compound CCCC1=NC(C)=C(C=O)N1 CHUGUCQQTLHMKZ-UHFFFAOYSA-N 0.000 description 1
CCBICNZACWTJTD-UHFFFAOYSA-N 6-(methoxymethyl)-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C(COC)=NC=C21 CCBICNZACWTJTD-UHFFFAOYSA-N 0.000 description 1
QOULTHINUSERBD-UHFFFAOYSA-N 6-benzyl-8-propyl-3h-imidazo[1,5-d][1,2,4]triazine-4-thione Chemical compound C1=NNC(=S)N2C1=C(CCC)N=C2CC1=CC=CC=C1 QOULTHINUSERBD-UHFFFAOYSA-N 0.000 description 1
QCIHIQNTTLSRAG-UHFFFAOYSA-N 6-phenyl-3h-imidazo[1,5-d][1,2,4]triazine-4-thione Chemical compound N12C(=S)NN=CC2=CN=C1C1=CC=CC=C1 QCIHIQNTTLSRAG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
IJYREXWLSRDEOX-UHFFFAOYSA-N 8-(bromomethyl)-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(CBr)N=C2C1=CC=CC=C1 IJYREXWLSRDEOX-UHFFFAOYSA-N 0.000 description 1
LPBISUMHIXPTOW-UHFFFAOYSA-N 8-bromo-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(Br)N=C2 LPBISUMHIXPTOW-UHFFFAOYSA-N 0.000 description 1
CYFMQDBVVDHMKG-UHFFFAOYSA-N 8-bromo-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazine-4-thione Chemical compound C1=NNC(=S)N2C1=C(Br)N=C2C1=CC=CC=C1 CYFMQDBVVDHMKG-UHFFFAOYSA-N 0.000 description 1
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 1
244000237956 Amaranthus retroflexus Species 0.000 description 1
235000004135 Amaranthus viridis Nutrition 0.000 description 1
244000036975 Ambrosia artemisiifolia Species 0.000 description 1
235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000209764 Avena fatua Species 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
239000002126 C01EB10 - Adenosine Substances 0.000 description 1
BFBFLUQKWLYWHW-UHFFFAOYSA-N CNNC(=O)N=N Chemical compound CNNC(=O)N=N BFBFLUQKWLYWHW-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
235000009332 Chenopodium rubrum Nutrition 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
241000282552 Chlorocebus aethiops Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
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 1
241000208296 Datura Species 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
235000021506 Ipomoea Nutrition 0.000 description 1
241000207783 Ipomoea Species 0.000 description 1
240000001549 Ipomoea eriocarpa Species 0.000 description 1
235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
238000006809 Jones oxidation reaction Methods 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
101001092200 Mus musculus RNA binding protein fox-1 homolog 3 Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000238367 Mya arenaria Species 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 1
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
244000275012 Sesbania cannabina Species 0.000 description 1
241000533293 Sesbania emerus Species 0.000 description 1
235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
240000003194 Sida rhombifolia Species 0.000 description 1
235000002834 Sida rhombifolia Nutrition 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000000944 Soxhlet extraction Methods 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
DNSMUPVUQGOFGT-UHFFFAOYSA-N [(5-methyl-2-propyl-1H-imidazol-4-yl)methylideneamino]carbamic acid Chemical compound CCCC1=NC(C=NNC(O)=O)=C(C)N1 DNSMUPVUQGOFGT-UHFFFAOYSA-N 0.000 description 1
VMTQRMVGJPFHDS-UHFFFAOYSA-N [5-methyl-2-(3-methylphenyl)-1h-imidazol-4-yl]methanol Chemical compound OCC1=C(C)NC(C=2C=C(C)C=CC=2)=N1 VMTQRMVGJPFHDS-UHFFFAOYSA-N 0.000 description 1
AWTOXNCMRSQBOX-UHFFFAOYSA-N [5-methyl-2-(4-nitrophenyl)-1h-imidazol-4-yl]methanol Chemical compound OCC1=C(C)NC(C=2C=CC(=CC=2)[N+]([O-])=O)=N1 AWTOXNCMRSQBOX-UHFFFAOYSA-N 0.000 description 1
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 1
LRKXKVGZYYTEEJ-UHFFFAOYSA-N [[5-methyl-2-(3-methylphenyl)-1H-imidazol-4-yl]methylideneamino]carbamic acid Chemical compound OC(=O)NN=CC1=C(C)NC(C=2C=C(C)C=CC=2)=N1 LRKXKVGZYYTEEJ-UHFFFAOYSA-N 0.000 description 1
QEAXZIMXYPAZAX-UHFFFAOYSA-N [amino-(3-methylphenyl)methylidene]azanium;chloride Chemical compound [Cl-].CC1=CC=CC(C(N)=[NH2+])=C1 QEAXZIMXYPAZAX-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
229960005305 adenosine Drugs 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
238000011166 aliquoting Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
235000003484 annual ragweed Nutrition 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
239000012131 assay buffer Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
125000003943 azolyl group Chemical group 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
229940058679 baza Drugs 0.000 description 1
230000008901 benefit Effects 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
235000006263 bur ragweed Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003518 caustics Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
235000003488 common ragweed Nutrition 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000012937 correction Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
VHJLVAABSRFDPM-ZXZARUISSA-N dithioerythritol Chemical compound SC[C@H](O)[C@H](O)CS VHJLVAABSRFDPM-ZXZARUISSA-N 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
HXDVBUOHJZMCDP-UHFFFAOYSA-N ethyl 2-imino-2-phenylacetate;hydrochloride Chemical compound Cl.CCOC(=O)C(=N)C1=CC=CC=C1 HXDVBUOHJZMCDP-UHFFFAOYSA-N 0.000 description 1
BBPOSHQFMBVAMI-UHFFFAOYSA-N ethyl 2-methoxyethanimidate Chemical compound CCOC(=N)COC BBPOSHQFMBVAMI-UHFFFAOYSA-N 0.000 description 1
APHMNTYBVWSBMO-UHFFFAOYSA-N ethyl N-[(2-tert-butyl-1H-imidazol-5-yl)methylideneamino]carbamate Chemical compound CCOC(=O)NN=CC1=CNC(C(C)(C)C)=N1 APHMNTYBVWSBMO-UHFFFAOYSA-N 0.000 description 1
AGUMHUYEEFHCLO-UHFFFAOYSA-N ethyl N-[(5-chloro-2-phenyl-1H-imidazol-4-yl)methylideneamino]carbamate Chemical compound N1C(Cl)=C(C=NNC(=O)OCC)N=C1C1=CC=CC=C1 AGUMHUYEEFHCLO-UHFFFAOYSA-N 0.000 description 1
YUSOXWXMQRWRDP-UHFFFAOYSA-N ethyl N-[[2-(2-propoxyphenyl)-1H-imidazol-5-yl]methylideneamino]carbamate Chemical compound CCCOC1=CC=CC=C1C1=NC(C=NNC(=O)OCC)=CN1 YUSOXWXMQRWRDP-UHFFFAOYSA-N 0.000 description 1
ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
238000003304 gavage Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
208000006278 hypochromic anemia Diseases 0.000 description 1
SUXODDGAYNUAAK-UHFFFAOYSA-N imidazo[4,5-e][1,2,4]triazine-3-thione Chemical class N1=NC(N=C2C1=NC=N2)=S SUXODDGAYNUAAK-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002664 inhalation therapy Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000002642 intravenous therapy Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
CCJHDZZUWZIVJF-UHFFFAOYSA-N iodo nitrate Chemical compound [O-][N+](=O)OI CCJHDZZUWZIVJF-UHFFFAOYSA-N 0.000 description 1
238000002386 leaching Methods 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229940057952 methanol Drugs 0.000 description 1
SGRXCTYMFBHRRR-UHFFFAOYSA-N methyl N-[(2-methyl-1H-imidazol-5-yl)methylideneamino]carbamodithioate Chemical compound CSC(=S)NN=CC1=CNC(C)=N1 SGRXCTYMFBHRRR-UHFFFAOYSA-N 0.000 description 1
PJCOTVYIUUFDEI-UHFFFAOYSA-N methyl N-[(5-methyl-2-phenyl-1H-imidazol-4-yl)methylideneamino]carbamodithioate Chemical compound N1C(C)=C(C=NNC(=S)SC)N=C1C1=CC=CC=C1 PJCOTVYIUUFDEI-UHFFFAOYSA-N 0.000 description 1
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
239000011812 mixed powder Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
108010028584 nucleotidase Proteins 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000004382 potting Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
108010043671 prostatic acid phosphatase Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
235000009736 ragweed Nutrition 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000001044 red dye Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
229960000581 salicylamide Drugs 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
239000003998 snake venom Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
229940001607 sodium bisulfite Drugs 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
238000000527 sonication Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940104261 taurate Drugs 0.000 description 1
CXEMWUYNUIKMNF-UHFFFAOYSA-N tert-butyl 4-chlorosulfonylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(S(Cl)(=O)=O)CC1 CXEMWUYNUIKMNF-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
229940055764 triaz Drugs 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000009637 wintergreen oil Substances 0.000 description 1

Classifications

- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen atoms
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

CA296,027A 1977-02-03 1978-02-02 Imidazo-as-triazine derivatives Expired CA1097638A (en)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date	Title
US76531777A	1977-02-03	1977-02-03
US76531877A	1977-02-03	1977-02-03
US765,318		1977-02-03
US765,317		1977-02-03
US84317377A	1977-10-18	1977-10-18
US843,174		1977-10-18
US843,173		1977-10-18
US05/843,174 US4107307A (en)	1977-02-03	1977-10-18	Imidazo [1,5-d]-as-triazine-4(3H)-ones and thiones
US848,836		1977-11-06
US05/848,836 US4124766A (en)	1977-02-03	1977-11-07	Substituted 3-(4-imidazolylmethylene)carbazic and thiocarbazic acid esters

Publications (1)

Publication Number	Publication Date
CA1097638A true CA1097638A (en)	1981-03-17

Family

ID=27542181

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA296,027A Expired CA1097638A (en)	1977-02-03	1978-02-02	Imidazo-as-triazine derivatives

Country Status (15)

Country	Link
JP (1)	JPS596316B2 (da)
AR (1)	AR224613A1 (da)
BE (1)	BE863567A (da)
CA (1)	CA1097638A (da)
CH (1)	CH636615A5 (da)
DE (1)	DE2804435A1 (da)
DK (1)	DK48778A (da)
FR (1)	FR2384772A1 (da)
GB (1)	GB1597671A (da)
GR (1)	GR73810B (da)
IE (1)	IE46511B1 (da)
IL (1)	IL53783A (da)
NL (1)	NL7801230A (da)
SE (1)	SE7801270L (da)
YU (1)	YU22078A (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3212749A1 (de) *	1982-04-06	1983-10-13	Basf Ag, 6700 Ludwigshafen	Neue 5-substituierte 4-methylimidazole und verfahren zu ihrer herstellung
DE3302413A1 (de) *	1983-01-21	1984-07-26	Schering AG, 1000 Berlin und 4709 Bergkamen	Triazinone, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit selektiver herbizider wirkung
JPS6337712A (ja) *	1986-08-01	1988-02-18	Hitachi Ltd	電界効果トランジスタの保護回路
JPH02185069A (ja) *	1988-12-02	1990-07-19	Motorola Inc	高エネルギー阻止能力及び温度補償された阻止電圧を具備する半導体デバイス
RU2103262C1 (ru) *	1992-07-16	1998-01-27	Лонца АГ Гампель/Валлис	Способ получения 2-замещенных 5-хлоримидазол-4-карбальдегидов
US5484939A (en) *	1993-03-12	1996-01-16	Lonza Ltd.	2-substituted 5-chlorimidazoles
US5442075A (en) *	1993-03-12	1995-08-15	Lonza Ltd.	Process for the production of 2-substituted 5-chlorimidazole-4-carbaldehydes
ATE157655T1 (de) *	1993-03-12	1997-09-15	Lonza Ag	Verfahren zur herstellung von gegebenfalls 2- substituierten 5-chlorimidazolen
CA2135541C (en) *	1993-11-15	2006-01-10	Gareth Griffiths	Process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes
CA2175420C (en) *	1995-05-17	2007-04-10	Gareth Griffiths	Process for the preparation of optionally 2-substituted 5-chloroimidazole-4-carbaldehydes
JP4103149B2 (ja)	1996-01-05	2008-06-18	ロンザリミテッド	２−置換５−クロロイミダゾール−４−カルブアルデヒドの製造方法
FR2842809A1 (fr) *	2002-07-26	2004-01-30	Greenpharma Sas	NOUVELLES PYRAZOLO[1,5-a]-1,3,5-TRIAZINES SUBSTITUEES ET LEURS ANALOGUES, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, UTILISATION A TITRE DE MEDICAMENT ET PROCEDES POUR LEUR PREPARATION

1978
- 1978-01-11 IL IL53783A patent/IL53783A/xx unknown
- 1978-01-13 GR GR55160A patent/GR73810B/el unknown
- 1978-01-16 GB GB1728/78A patent/GB1597671A/en not_active Expired
- 1978-01-23 AR AR270809A patent/AR224613A1/es active
- 1978-01-31 IE IE208/78A patent/IE46511B1/en unknown
- 1978-01-31 YU YU00220/78A patent/YU22078A/xx unknown
- 1978-02-02 DE DE19782804435 patent/DE2804435A1/de not_active Withdrawn
- 1978-02-02 NL NL7801230A patent/NL7801230A/xx not_active Application Discontinuation
- 1978-02-02 BE BE184833A patent/BE863567A/xx not_active IP Right Cessation
- 1978-02-02 CH CH114578A patent/CH636615A5/de not_active IP Right Cessation
- 1978-02-02 DK DK48778A patent/DK48778A/da not_active Application Discontinuation
- 1978-02-02 CA CA296,027A patent/CA1097638A/en not_active Expired
- 1978-02-02 SE SE7801270A patent/SE7801270L/xx unknown
- 1978-02-03 FR FR7803141A patent/FR2384772A1/fr not_active Withdrawn
- 1978-02-03 JP JP53010649A patent/JPS596316B2/ja not_active Expired

Also Published As

Publication number	Publication date
FR2384772A1 (fr)	1978-10-20
DK48778A (da)	1978-08-04
YU22078A (en)	1983-12-31
IL53783A (en)	1982-08-31
GR73810B (da)	1984-04-17
JPS5398994A (en)	1978-08-29
IE46511B1 (en)	1983-07-13
DE2804435A1 (de)	1978-08-17
BE863567A (fr)	1978-08-02
SE7801270L (sv)	1978-09-29
IE780208L (en)	1978-08-03
NL7801230A (nl)	1978-08-07
IL53783A0 (en)	1978-04-30
JPS596316B2 (ja)	1984-02-10
AR224613A1 (es)	1981-12-30
CH636615A5 (en)	1983-06-15
GB1597671A (en)	1981-09-09

Legal Events

Date	Code	Title	Description
1998-03-17	MKEX	Expiry

Publication	Publication Date	Title
CA1097638A (en)	1981-03-17	Imidazo-as-triazine derivatives
CA1065322A (en)	1979-10-30	Imidazole and 1,2,4-triazole compounds
US6020492A (en)	2000-02-01	Deazapurine derivatives; a new class of CRF1 specific ligands
US4107307A (en)	1978-08-15	Imidazo [1,5-d]-as-triazine-4(3H)-ones and thiones
CA1212952A (en)	1986-10-21	1-phenyl-2-triazolyl-ethyl ether derivatives and their use as fungicides
US3940415A (en)	1976-02-24	1-(Imidazolyl-1)-2-aryloxy-3-hydroxy-alkanes
USRE30511E (en)	1981-02-10	Imidazo[1,5-d]-as-triazine-4(3H)-ones and thiones
NL8201021A (nl)	1982-10-18	2-fenoxyalkyl-1,2,4-triazool-3-on verbindingen en derivaten daarvan met antidepressieve werking; werkwijze voor het bereiden daarvan; farmaceutische preparaten; werkwijze voor het behandelen van depressie bij zoogdieren.
CA1092128A (en)	1980-12-23	Combatting fungi with 1-(azol-1-yl)-4-halo-1-phenoxy- butan-2-ones and -ols
US5644057A (en)	1997-07-01	Deazapurine derivatives; a new class of CRF1 specific ligands
US3996366A (en)	1976-12-07	Thio derivatives of imidazol-1-yl carboxamides
FI95036C (fi)	1995-12-11	Tieno-triatsolo-diatsepiinijohdosten valmistusmenetelmä
EP0244098A2 (en)	1987-11-04	Thiazolotriazole herbicides
US3910909A (en)	1975-10-07	Process for the preparation of 1,2,4-triazin-5-one compounds
EP0244097A2 (en)	1987-11-04	Pyrazolopyrimidine herbicides
JPS6052148B2 (ja)	1985-11-18	α−アゾリル−β−ヒドロキシ−ケトン、その製造方法および殺菌剤組成物
CA1173445A (en)	1984-08-28	Quinolone derivatives and their use as pharmaceuticals
EP0352946A1 (en)	1990-01-31	Triazole antifungal agents
EP0191514B1 (en)	1991-04-03	Imidazole derivatives, their preparation and their use as fungicides
US4124766A (en)	1978-11-07	Substituted 3-(4-imidazolylmethylene)carbazic and thiocarbazic acid esters
US4107308A (en)	1978-08-15	Imidazo[1,5-d]-as-triazines
US4168964A (en)	1979-09-25	Method for the control of undesired plant species using imidazo-as-triazinones and triazine-thiones
US4167570A (en)	1979-09-11	2-Methyl-6-alkyl-11-aminoalkyl-6,11-dihydro-5H-pyrido(2,3-B)(1,5)benzodiazepin-5-ones and salts thereof
EP0254364B1 (en)	1991-09-11	Imidazole derivative
US4215220A (en)	1980-07-29	1-(2-Oxysubstituted-3-anilinopropyl)-imidazoles