CA1114400A - Derives antiviraux amines et amidines de glycerol et de propanediols - Google Patents

Derives antiviraux amines et amidines de glycerol et de propanediols

Info

Publication number: CA1114400A
Authority: CA; Canada
Prior art keywords: hexadecyl; compound; glycerol; mmoles; solution
Prior art date: 1977-08-18
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

CA362,367A

Other languages

English (en)

Inventor

Allen R. Kraska

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.)

Pfizer Corp SRL

Original Assignee

Pfizer Corp SRL

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.)

1977-08-18

Filing date

1980-10-14

Publication date

1981-12-15

1977-08-18 Priority claimed from US05/825,535 external-priority patent/US4166132A/en

1980-10-14 Application filed by Pfizer Corp SRL filed Critical Pfizer Corp SRL

1980-10-14 Priority to CA362,367A priority Critical patent/CA1114400A/fr

1981-12-15 Application granted granted Critical

1981-12-15 Publication of CA1114400A publication Critical patent/CA1114400A/fr

Status Expired legal-status Critical Current

Links

-1 amidine derivatives of glycerol Chemical class 0.000 title claims description 39
150000001412 amines Chemical class 0.000 title abstract description 7
230000000840 anti-viral effect Effects 0.000 title description 9
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 16
239000002253 acid Substances 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims description 85
229910052739 hydrogen Inorganic materials 0.000 claims description 40
238000000034 method Methods 0.000 claims description 26
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
230000008569 process Effects 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 91
241000124008 Mammalia Species 0.000 abstract description 9
125000003342 alkenyl group Chemical group 0.000 abstract description 6
150000001409 amidines Chemical class 0.000 abstract description 3
230000003612 virological effect Effects 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 74
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 70
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
239000000203 mixture Substances 0.000 description 61
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
239000007787 solid Substances 0.000 description 38
229910052757 nitrogen Inorganic materials 0.000 description 37
229910052799 carbon Inorganic materials 0.000 description 33
239000003921 oil Substances 0.000 description 25
235000019198 oils Nutrition 0.000 description 24
241000700605 Viruses Species 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
229910052943 magnesium sulfate Inorganic materials 0.000 description 20
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 19
238000000921 elemental analysis Methods 0.000 description 19
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
238000010828 elution Methods 0.000 description 18
239000000047 product Substances 0.000 description 17
101150041968 CDC13 gene Proteins 0.000 description 16
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
210000004027 cell Anatomy 0.000 description 16
239000012259 ether extract Substances 0.000 description 15
239000007789 gas Substances 0.000 description 15
102000014150 Interferons Human genes 0.000 description 13
108010050904 Interferons Proteins 0.000 description 13
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
229910000041 hydrogen chloride Inorganic materials 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
235000011187 glycerol Nutrition 0.000 description 12
238000010898 silica gel chromatography Methods 0.000 description 12
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 11
238000010992 reflux Methods 0.000 description 11
239000011734 sodium Substances 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
239000011780 sodium chloride Substances 0.000 description 11
238000007792 addition Methods 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
230000037396 body weight Effects 0.000 description 10
229940079322 interferon Drugs 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
241000699670 Mus sp. Species 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
239000002609 medium Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000009472 formulation Methods 0.000 description 7
208000015181 infectious disease Diseases 0.000 description 7
239000000463 material Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
241000711975 Vesicular stomatitis virus Species 0.000 description 6
208000036142 Viral infection Diseases 0.000 description 6
239000003443 antiviral agent Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000007858 starting material Substances 0.000 description 6
230000004083 survival effect Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
230000009385 viral infection Effects 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
241000726306 Irus Species 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
239000002245 particle Substances 0.000 description 5
229940115272 polyinosinic:polycytidylic acid Drugs 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
230000001413 cellular effect Effects 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
239000010452 phosphate Substances 0.000 description 4
239000002953 phosphate buffered saline Substances 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
108091003079 Bovine Serum Albumin Proteins 0.000 description 3
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 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
208000037062 Polyps Diseases 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000000120 cytopathologic effect Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000012894 fetal calf serum Substances 0.000 description 3
230000001605 fetal effect Effects 0.000 description 3
238000005227 gel permeation chromatography Methods 0.000 description 3
239000001963 growth medium Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
239000005457 ice water Substances 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
230000002458 infectious effect Effects 0.000 description 3
229940047124 interferons Drugs 0.000 description 3
238000012423 maintenance Methods 0.000 description 3
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229940068968 polysorbate 80 Drugs 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000001488 sodium phosphate Substances 0.000 description 3
229910000162 sodium phosphate Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
125000005490 tosylate group Chemical group 0.000 description 3
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
239000006145 Eagle's minimal essential medium Substances 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000000592 Nasal Polyps Diseases 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
239000007975 buffered saline Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
244000309466 calf Species 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000084 colloidal system Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012531 culture fluid Substances 0.000 description 2
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
210000002950 fibroblast Anatomy 0.000 description 2
238000001914 filtration Methods 0.000 description 2
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 2
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 2
238000011534 incubation Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
208000016366 nasal cavity polyp Diseases 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000001294 propane Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010791 quenching Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
241000894007 species Species 0.000 description 2
238000003756 stirring Methods 0.000 description 2
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 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
FXPQEQPJRBVGRB-UHFFFAOYSA-N 1,3-dihexadecoxypropan-2-amine Chemical compound CCCCCCCCCCCCCCCCOCC(N)COCCCCCCCCCCCCCCCC FXPQEQPJRBVGRB-UHFFFAOYSA-N 0.000 description 1
SUXARMXOCMNMFR-UHFFFAOYSA-N 1-(2,3-dihexadecoxypropyl)-4-phenylpiperidine-4-carbonitrile Chemical compound C1CN(CC(COCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCC)CCC1(C#N)C1=CC=CC=C1 SUXARMXOCMNMFR-UHFFFAOYSA-N 0.000 description 1
QDQMRNALDYYEFA-UHFFFAOYSA-N 1-(3-azidopropoxy)hexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCN=[N+]=[N-] QDQMRNALDYYEFA-UHFFFAOYSA-N 0.000 description 1
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
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125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
CVKOOKPNCVYHNY-UHFFFAOYSA-N 3-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC(C#N)=C1 CVKOOKPNCVYHNY-UHFFFAOYSA-N 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
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125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

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CA362,367A 1977-08-18 1980-10-14 Derives antiviraux amines et amidines de glycerol et de propanediols Expired CA1114400A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA362,367A CA1114400A (fr)	1977-08-18	1980-10-14	Derives antiviraux amines et amidines de glycerol et de propanediols

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/825,535 US4166132A (en)	1977-08-18	1977-08-18	Antiviral amine derivatives of glycerol and propanediols
US825,535		1977-08-18
CA309,488A CA1102354A (fr)	1977-08-18	1978-08-16	Traduction non-disponible
CA362,367A CA1114400A (fr)	1977-08-18	1980-10-14	Derives antiviraux amines et amidines de glycerol et de propanediols

Publications (1)

Publication Number	Publication Date
CA1114400A true CA1114400A (fr)	1981-12-15

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ID=27165804

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Application Number	Title	Priority Date	Filing Date
CA362,367A Expired CA1114400A (fr)	1977-08-18	1980-10-14	Derives antiviraux amines et amidines de glycerol et de propanediols

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CA (1)	CA1114400A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5013482A (en) *	1988-07-21	1991-05-07	Ciba-Geigy Corporation	Corrosion inhibition
US5176850A (en) *	1988-07-21	1993-01-05	Ciba-Geigy Corporation	Substituted glycerol compounds

1980
- 1980-10-14 CA CA362,367A patent/CA1114400A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5013482A (en) *	1988-07-21	1991-05-07	Ciba-Geigy Corporation	Corrosion inhibition
US5176850A (en) *	1988-07-21	1993-01-05	Ciba-Geigy Corporation	Substituted glycerol compounds

Legal Events

Date	Code	Title	Description
1998-12-15	MKEX	Expiry

Publication	Publication Date	Title
CA1102354A (fr)	1981-06-02	Traduction non-disponible
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EP3758495A1 (fr)	2021-01-06	Compositions de nanoparticules
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DE3212375A1 (de)	1983-02-03	Angrenzend substituierte cycloalkan-amid-analgetika
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EP0296573A2 (fr)	1988-12-28	Nucléosides, leur préparation et compositions pharmaceutiques
CH627753A5 (de)	1982-01-29	Verfahren zur herstellung von neuen sulfonylbenzimidazolen.
US3932643A (en)	1976-01-13	Phenanthridines and phenanthridinones as antiviral agents
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DD255351A5 (de)	1988-03-30	Verfahren zur herstellung von carbocyclischen purinnucleosiden
EP0038161A1 (fr)	1981-10-21	2,6-Diaminonebularines, leur préparation et leur utilisation
CA1121358A (fr)	1982-04-06	Derives amines et amidines du glycerol et du propanediol utilises comme agents antiviraux
FI67556B (fi)	1984-12-31	Foerfarande foer framstaellning av nya saosom antivirala medelanvaendbara substituerade acetofenonderivat
US11655238B2 (en)	2023-05-23	MMPL3 inhibitors, compositions and uses thereof
US4262021A (en)	1981-04-14	Antiviral amine and amidine derivatives of glycerol and propanediols
Tronchet et al.	1994	Anti-HIV derivatives of 1-(2, 3-dideoxy-3-N-hydroxyamino-β-D-threo-pentofuranosyl) thymine
US4193999A (en)	1980-03-18	Antiviral amine derivatives of propanediols
US4215146A (en)	1980-07-29	Antiviral amine derivatives of glycerol and propanediols
US3532741A (en)	1970-10-06	Amino,monomethylamino and dimethylamino derivatives of decahydro-1,5,2,4 - ethanediylidenecyclopenta(cd) pentalene
US5489609A (en)	1996-02-06	2-aminoethanesulfonic acid zinc complex compound
EP0080305A1 (fr)	1983-06-01	2'-Déoxyuridines à activité antivirale, leur préparation et emploi
KR830000465B1 (ko)	1983-03-09	항바이러스제인 글리세롤 및 프로판디올의 아민 및 아미딘유도체의 제조방법

CA1114400A - Derives antiviraux amines et amidines de glycerol et de propanediols - Google Patents

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Priority Applications (1)

Applications Claiming Priority (4)

Publications (1)

Family

ID=27165804

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

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