NO134656B - - Google Patents

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Publication number: NO134656B
Authority: NO; Norway
Prior art keywords: bis; dibenzofuran; acid; compound; compounds
Prior art date: 1970-09-14

Application number

NO3394/71A

Other languages

English (en)

Norwegian (no)

Other versions

NO134656C (pt

Inventor

W L Albrecht

R W Fleming

Original Assignee

Richardson Merrell Inc

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.)

1970-09-14

Filing date

1971-09-13

Publication date

1976-08-16

1971-09-13 Application filed by Richardson Merrell Inc filed Critical Richardson Merrell Inc

1976-08-16 Publication of NO134656B publication Critical patent/NO134656B/no

1976-11-24 Publication of NO134656C publication Critical patent/NO134656C/no

Links

150000001875 compounds Chemical class 0.000 claims description 40
TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 14
230000000840 anti-viral effect Effects 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 5
UYTYOSNFCVYCDS-UHFFFAOYSA-N 2-chloro-1-[8-(2-chloroacetyl)dibenzofuran-2-yl]ethanone Chemical compound C1=C(C(=O)CCl)C=C2C3=CC(C(=O)CCl)=CC=C3OC2=C1 UYTYOSNFCVYCDS-UHFFFAOYSA-N 0.000 claims description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
-1 bis-[2-(diethylamino)acetyl]dibenzofuran Chemical compound 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
OUIWLPBJLPYGOH-UHFFFAOYSA-N 4-chloro-1-[8-(4-chlorobutanoyl)dibenzofuran-2-yl]butan-1-one Chemical compound C1=C(C(=O)CCCCl)C=C2C3=CC(C(=O)CCCCl)=CC=C3OC2=C1 OUIWLPBJLPYGOH-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000012458 free base Substances 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
241000700605 Viruses Species 0.000 description 16
241001465754 Metazoa Species 0.000 description 14
239000004480 active ingredient Substances 0.000 description 11
208000015181 infectious disease Diseases 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000011282 treatment Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
230000000694 effects Effects 0.000 description 8
102000014150 Interferons Human genes 0.000 description 7
108010050904 Interferons Proteins 0.000 description 7
229940079322 interferon Drugs 0.000 description 7
230000000069 prophylactic effect Effects 0.000 description 7
230000001225 therapeutic effect Effects 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000037396 body weight Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
239000007787 solid Substances 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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
230000001717 pathogenic effect Effects 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
UHCRFLYKHXRLRI-UHFFFAOYSA-N 4-morpholin-4-yl-1-[8-(4-morpholin-4-ylbutanoyl)dibenzofuran-2-yl]butan-1-one Chemical compound C=1C=C2OC3=CC=C(C(=O)CCCN4CCOCC4)C=C3C2=CC=1C(=O)CCCN1CCOCC1 UHCRFLYKHXRLRI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000709664 Picornaviridae Species 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000470 constituent Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
230000000415 inactivating effect Effects 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
241000894007 species Species 0.000 description 2
150000003512 tertiary amines Chemical group 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
230000003612 virological effect Effects 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ORKZZNJFSSKSLS-UHFFFAOYSA-N 2-(diethylamino)-1-[8-[2-(diethylamino)acetyl]dibenzofuran-2-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C1=C(C(=O)CN(CC)CC)C=C2C3=CC(C(=O)CN(CC)CC)=CC=C3OC2=C1 ORKZZNJFSSKSLS-UHFFFAOYSA-N 0.000 description 1
RCOQUBUUUCYCJE-UHFFFAOYSA-N 2-(dimethylamino)-1-[8-[2-(dimethylamino)acetyl]dibenzofuran-2-yl]ethanone;dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl.C1=C(C(=O)CN(C)C)C=C2C3=CC(C(=O)CN(C)C)=CC=C3OC2=C1 RCOQUBUUUCYCJE-UHFFFAOYSA-N 0.000 description 1
LHEGATUXJNBGRM-UHFFFAOYSA-N 2-(dimethylamino)-1-[8-[2-(dimethylamino)acetyl]dibenzothiophen-2-yl]ethanone Chemical compound C1=C(C(=O)CN(C)C)C=C2C3=CC(C(=O)CN(C)C)=CC=C3SC2=C1 LHEGATUXJNBGRM-UHFFFAOYSA-N 0.000 description 1
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
KBOGMBQWZCIHNQ-UHFFFAOYSA-N 5-chloro-3-methylpentanoyl chloride Chemical compound ClCCC(C)CC(Cl)=O KBOGMBQWZCIHNQ-UHFFFAOYSA-N 0.000 description 1
SVNNWKWHLOJLOK-UHFFFAOYSA-N 5-chloropentanoyl chloride Chemical compound ClCCCCC(Cl)=O SVNNWKWHLOJLOK-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
241000271566 Aves Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241000700198 Cavia Species 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000710188 Encephalomyocarditis virus Species 0.000 description 1
238000005967 Finkelstein reaction Methods 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
241000699694 Gerbillinae Species 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000282339 Mustela Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000606651 Rickettsiales Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010046865 Vaccinia virus infection Diseases 0.000 description 1
239000012345 acetylating agent Substances 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004826 dibenzofurans Chemical class 0.000 description 1
IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940015043 glyoxal Drugs 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000009545 invasion Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229940107700 pyruvic acid Drugs 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
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960004889 salicylic acid Drugs 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
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
208000007089 vaccinia Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO3394/71A 1970-09-14 1971-09-13 NO134656C (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/072,171 US4146624A (en)	1970-09-14	1970-09-14	Method of treating viruses with bis-basic ketones of dibenzofuran

Publications (2)

Publication Number	Publication Date
NO134656B true NO134656B (pt)	1976-08-16
NO134656C NO134656C (pt)	1976-11-24

Family

ID=22106024

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3394/71A NO134656C (pt)	1970-09-14	1971-09-13

Country Status (7)

Country	Link
US (1)	US4146624A (pt)
AU (1)	AU461332B2 (pt)
BE (1)	BE772582A (pt)
CA (1)	CA973477A (pt)
FR (1)	FR2106515B1 (pt)
GB (2)	GB1368469A (pt)
NO (1)	NO134656C (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2211460A (en) *	1987-11-19	1989-07-05	Gohei Mizota	Manufacturing method for layerlike multicoloured moulding
TW248556B (pt) *	1993-01-18	1995-06-01	Takeda Pharm Industry Co
US5763609A (en)	1996-03-21	1998-06-09	Neurogen Corporation	Certain pyrrolo pyridine-3-carboxamides; a new class of gaba brain receptor ligands

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3083201A (en) *	1961-02-13	1963-03-26	Smith Kline French Lab	Glyoxal derivatives of dibenzofuran and dibenzothiophene
US3867409A (en) *	1969-06-16	1975-02-18	Richardson Merrell Inc	Bis-basic esters of dibenzofuran
US3682921A (en) *	1971-05-19	1972-08-08	Aldrich Chem Co Inc	Dibenzofuryl ketones

1970
- 1970-09-14 US US05/072,171 patent/US4146624A/en not_active Expired - Lifetime
1971
- 1971-09-02 CA CA121,987A patent/CA973477A/en not_active Expired
- 1971-09-06 GB GB4151471A patent/GB1368469A/en not_active Expired
- 1971-09-06 GB GB3514473A patent/GB1368470A/en not_active Expired
- 1971-09-13 NO NO3394/71A patent/NO134656C/no unknown
- 1971-09-13 AU AU33394/71A patent/AU461332B2/en not_active Expired
- 1971-09-14 FR FR7133096A patent/FR2106515B1/fr not_active Expired
- 1971-09-14 BE BE772582A patent/BE772582A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU3339471A (en)	1973-03-22
CA973477A (en)	1975-08-26
GB1368469A (en)	1974-09-25
US4146624A (en)	1979-03-27
BE772582A (fr)	1972-01-17
NO134656C (pt)	1976-11-24
GB1368470A (en)	1974-09-25
FR2106515A1 (pt)	1972-05-05
FR2106515B1 (pt)	1974-09-06
AU461332B2 (en)	1975-05-22

Publication	Publication Date	Title
FI64357C (fi)	1983-11-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara ftalazin-4-ylaettiksyraderivat
US3862134A (en)	1975-01-21	Phenylbenzofuran acrylic acid compounds and salts and esters thereof
US2996503A (en)	1961-08-15	Derivatives of heterocyclic compounds
US3719712A (en)	1973-03-06	2-phenylethynyl-benzyl-amines
JPH0217534B2 (pt)	1990-04-20
US4025552A (en)	1977-05-24	3-(4'-Alkoxy-benzoyl)-1,2,2-trimethylcyclopentane-carboxylic acids, methods of use and compositions containing such compounds
NO134656B (pt)	1976-08-16
EP1068193A1 (en)	2001-01-17	Benzylpiperazinyl- and benzylpiperidinyl ethanone derivatives, their preparation and their use as dopamine d 4? receptor antagonists
KR0182093B1 (ko)	1999-05-01	4-(p-플로오로페닐)-3-[(3,4-(메틸렌디옥시)페녹시)메틸]피페리딘의 n-p-할로벤조일메틸 유도체
US3506653A (en)	1970-04-14	Non-steroid hormonal agents
US2944053A (en)	1960-07-05	Uiiilcu
US3932424A (en)	1976-01-13	Bis-basic ethers of carbazole
US3720680A (en)	1973-03-13	Bis-basic ethers and thioethers of dibenzothiophene
US3906007A (en)	1975-09-16	Bis-basic ketones of dibenzofuran
US2615024A (en)	1952-10-21	Basic esters and amides of 7-substituted-coumarin-4-acetic acids and salts and processes of preparation
US4528294A (en)	1985-07-09	Benzoyl-phenyl-piperidine derivatives
CA2704649C (en)	2015-02-17	Tetracyclic dipyrano-coumarin compounds with anti-hiv and anti-mycobacterium tuberculosis activities
US3800044A (en)	1974-03-26	Pharmaceutical methods using a substituted 10-aminoalkyl-9,10-dihydroanthracene
Sharma et al.	1975	Potential filaricides. 6. Synthesis of 3, 8-disubstituted 1, 3, 8-triazabicyclo [4.4. 0] decan-2-ones and-thiones
SU895283A3 (ru)	1981-12-30	Способ получени производных @ -алкил-о-оксибензиламина или их солей
NO133446B (pt)	1976-01-26
KR870000034B1 (ko)	1987-02-07	〔1-옥소-2-아릴 또는 티에닐-2-치환-5-인다닐옥시〕알칸산의 제조방법
IE66828B1 (en)	1996-02-07	Thioxanthenone antitumor agents
US3442890A (en)	1969-05-06	Substituted 3-benzazocin-16-ones
US2970152A (en)	1961-01-31	Anilinobenzoquinone derivatives