CA1074803A - 1-thiazolinyl-5(6)-substituant-ben-zimidazoles - Google Patents

1-thiazolinyl-5(6)-substituant-ben-zimidazoles

Info

Publication number: CA1074803A
Authority: CA; Canada
Prior art keywords: alpha; amino; benzimidazole; thiazolin; hydroxy
Prior art date: 1977-02-08
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

CA271,306A

Other languages

English (en)

Inventor

James H. Wikel

James W. Chamberlin

Charles J. Paget

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.)

Eli Lilly and Co

Original Assignee

Eli Lilly and 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.)

1977-02-08

Filing date

1977-02-08

Publication date

1980-04-01

1977-02-08 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1977-02-08 Priority to CA271,306A priority Critical patent/CA1074803A/fr

1980-04-01 Application granted granted Critical

1980-04-01 Publication of CA1074803A publication Critical patent/CA1074803A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 29
-1 alkyl lithium Chemical compound 0.000 claims abstract description 20
230000007062 hydrolysis Effects 0.000 claims abstract description 6
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 6
230000018044 dehydration Effects 0.000 claims abstract description 5
238000006297 dehydration reaction Methods 0.000 claims abstract description 5
229910052744 lithium Inorganic materials 0.000 claims abstract description 4
230000010933 acylation Effects 0.000 claims abstract description 3
238000005917 acylation reaction Methods 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 23
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 4
125000001118 alkylidene group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 claims description 2
LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 claims description 2
JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims 13
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
MJOVZNXYZWBZCZ-UHFFFAOYSA-N [2-amino-3-(4,5-dihydro-1,3-thiazol-2-yl)benzimidazol-5-yl]-phenylmethanone Chemical compound NC1=NC2=CC=C(C(=O)C=3C=CC=CC=3)C=C2N1C1=NCCS1 MJOVZNXYZWBZCZ-UHFFFAOYSA-N 0.000 claims 1
ZRIDOZNUOSTIRL-UHFFFAOYSA-N [2-amino-7-(4,5-dihydro-1,3-thiazol-2-yl)-3h-benzimidazol-5-yl]-phenylmethanone Chemical compound C1=C2NC(N)=NC2=C(C=2SCCN=2)C=C1C(=O)C1=CC=CC=C1 ZRIDOZNUOSTIRL-UHFFFAOYSA-N 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000007818 Grignard reagent Substances 0.000 abstract description 3
150000004795 grignard reagents Chemical class 0.000 abstract description 3
239000003443 antiviral agent Substances 0.000 abstract 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 16
241000700605 Viruses Species 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
241000709661 Enterovirus Species 0.000 description 8
239000000243 solution Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
241001466953 Echovirus Species 0.000 description 4
241000991587 Enterovirus C Species 0.000 description 4
208000000474 Poliomyelitis Diseases 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
108091003079 Bovine Serum Albumin Proteins 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000710185 Mengo virus Species 0.000 description 3
125000002723 alicyclic group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
229940124339 anthelmintic agent Drugs 0.000 description 3
239000000921 anthelmintic agent Substances 0.000 description 3
150000001556 benzimidazoles Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012091 fetal bovine serum Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
241000712461 unidentified influenza virus Species 0.000 description 3
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 2
241000709687 Coxsackievirus Species 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
230000000507 anthelmentic effect Effects 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
230000000840 anti-viral effect Effects 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
235000001055 magnesium Nutrition 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229940091250 magnesium supplement Drugs 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229960005322 streptomycin Drugs 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
WVRLKTCLXAUFLG-UHFFFAOYSA-N 1-(2-phenyl-1H-benzimidazol-4-yl)-4,5-dihydro-3H-1,3-thiazole Chemical class S1(=CNCC1)C1=CC=CC=2N=C(NC=21)C1=CC=CC=C1 WVRLKTCLXAUFLG-UHFFFAOYSA-N 0.000 description 1
PDOHXRTUUOTTIR-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-thiazol-2-yl)-6-(1-phenylprop-1-enyl)benzimidazol-2-amine Chemical compound C=1C=C2N=C(N)N(C=3SCCN=3)C2=CC=1C(=CC)C1=CC=CC=C1 PDOHXRTUUOTTIR-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
RZMKWQVADPIKCJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl(phenyl)methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C1=CC=CC=C1 RZMKWQVADPIKCJ-UHFFFAOYSA-N 0.000 description 1
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
KRXGEFPVDMGGGU-UHFFFAOYSA-N 4-(4,5-dihydro-3h-1,3-thiazol-1-yl)-1h-benzimidazol-2-amine Chemical class C1=CC=C2NC(N)=NC2=C1S1=CNCC1 KRXGEFPVDMGGGU-UHFFFAOYSA-N 0.000 description 1
241000220479 Acacia Species 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
241000282465 Canis Species 0.000 description 1
241000282552 Chlorocebus aethiops Species 0.000 description 1
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
STECJAGHUSJQJN-USLFZFAMSA-N LSM-4015 Chemical compound C1([C@@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-USLFZFAMSA-N 0.000 description 1
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 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
238000010521 absorption reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical compound [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000011161 development Methods 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
210000003292 kidney cell Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
229960000869 magnesium oxide Drugs 0.000 description 1
235000012245 magnesium oxide Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
230000007505 plaque formation Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 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
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray 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
239000008117 stearic acid Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000002769 thiazolinyl group Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA271,306A 1977-02-08 1977-02-08 1-thiazolinyl-5(6)-substituant-ben-zimidazoles Expired CA1074803A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA271,306A CA1074803A (fr)	1977-02-08	1977-02-08	1-thiazolinyl-5(6)-substituant-ben-zimidazoles

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA271,306A CA1074803A (fr)	1977-02-08	1977-02-08	1-thiazolinyl-5(6)-substituant-ben-zimidazoles

Publications (1)

Publication Number	Publication Date
CA1074803A true CA1074803A (fr)	1980-04-01

Family

ID=4107889

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA271,306A Expired CA1074803A (fr)	1977-02-08	1977-02-08	1-thiazolinyl-5(6)-substituant-ben-zimidazoles

Country Status (1)

Country	Link
CA (1)	CA1074803A (fr)

1977
- 1977-02-08 CA CA271,306A patent/CA1074803A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-04-01	MKEX	Expiry

Publication	Publication Date	Title
CA1197245A (fr)	1985-11-26	Benzimidazoles olefiniques
US4216313A (en)	1980-08-05	Antiviral thiazinyl benzimidazoles
IE43618B1 (en)	1981-04-08	2-(amino or acylamino)-1-(thiazolinyl or dihydrothiazinyl)-benzimidazole-5(6)-carboxylic acid esters
US4174454A (en)	1979-11-13	Alkylidenylmethyl-substituted 1-sulfonylbenzimidazoles
PL150841B1 (en)	1990-07-31	Purine compounds.
EP0199393A1 (fr)	1986-10-29	Dérivés d'indène et de naphtalène
US4134896A (en)	1979-01-16	5,6-Dihydro-4-oxo-4H-thieno[2,3-b]thiopyran-5-carboxamides, and process for the preparation thereof
CA1074803A (fr)	1980-04-01	1-thiazolinyl-5(6)-substituant-ben-zimidazoles
US4230868A (en)	1980-10-28	α-Alkyl-α-hydroxybenzyl-substituted 1-sulfonylbenzimidazoles
CA1079737A (fr)	1980-06-17	1-sulfonyl-5(6)-a substitution-benzimidazoles
US4049816A (en)	1977-09-20	Antiviral 2-amino-5-[1-(indol-3-yl)alkyl]-2-thiazolin-4-ones
US4338315A (en)	1982-07-06	Antiviral method employing thiazinyl benzimidazole derivatives
US4293558A (en)	1981-10-06	Antiviral thiazolinyl benzimidazoles and derivatives
US4338329A (en)	1982-07-06	Antiviral method employing 1-sulfonylbenzimidazoles
JPS6117828B2 (fr)	1986-05-09
GB1568542A (en)	1980-05-29	2-(amino or acylamino)-1-(2-thiazolin-2-yl)benzimidazoles
US4065570A (en)	1977-12-27	Antiviral 5-(substituted benzal) hydantoins
US4264617A (en)	1981-04-28	Antiviral 5-(substituted benzal) hydantoins
US4013770A (en)	1977-03-22	Antiviral 5-(substituted benzal) hydantoins
IE44597B1 (en)	1982-01-27	2-(amino or acylamino)-1-(2-thiazolin-2-yl)benzimidazoles
KR810000232B1 (ko)	1981-03-23	1-티아졸리닐-5(6)-치환-벤즈이미다졸 유도체의 제조방법
JPH08134044A (ja)	1996-05-28	新規ピリミジン化合物、中間体及びそれらの製造法
US4330555A (en)	1982-05-18	Indanyloxamic derivatives, their preparation and pharmaceutical compositions containing them
KR800001218B1 (ko)	1980-10-24	티아졸리닐 케로벤즈아미다졸 및 이의 유도체의 제조방법
CS202561B2 (cs)	1981-01-30	Způsob výroby l-sulfonylbenzimidazolů, substituovaných na karbonylové skupině