NO790778L - Fremgangsmaate ved fremstilling av antirhinovirale midler - Google Patents

Fremgangsmaate ved fremstilling av antirhinovirale midler

Info

Publication number: NO790778L
Authority: NO; Norway
Prior art keywords: methyl; ethyl; thieno; pyrazolo; reaction
Prior art date: 1978-03-10

Application number

NO790778A

Other languages

English (en)

Norwegian (no)

Inventor

Edward Charles Hermann

Joel Gayton Whitney

Original Assignee

Du Pont

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.)

1978-03-10

Filing date

1979-03-08

Publication date

1979-09-11

1978-12-21 Priority claimed from US05/970,732 external-priority patent/US4220776A/en

1979-03-08 Application filed by Du Pont filed Critical Du Pont

1979-09-11 Publication of NO790778L publication Critical patent/NO790778L/no

Links

238000000034 method Methods 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 5
230000002128 anti-rhinoviral effect Effects 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 31
-1 1-adamantyl Chemical group 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Chemical group 0.000 claims description 4
239000000376 reactant Substances 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 3
MUXPPYATEKVUBJ-UHFFFAOYSA-N 2,2-diethylbutanoyl chloride Chemical compound CCC(CC)(CC)C(Cl)=O MUXPPYATEKVUBJ-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000004965 chloroalkyl group Chemical group 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229910052731 fluorine Chemical group 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
239000011737 fluorine Chemical group 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
241000709661 Enterovirus Species 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
238000001914 filtration Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000011282 treatment Methods 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000000725 suspension Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
201000009240 nasopharyngitis Diseases 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
229940080818 propionamide Drugs 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
IAOVZTOQEPQEIO-UHFFFAOYSA-N 3-bromothieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CC=C2C(Br)=C(C(=O)N)SC2=N1 IAOVZTOQEPQEIO-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
206010061494 Rhinovirus infection Diseases 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
SFDIRKDBTVHEEY-UHFFFAOYSA-N ethyl 3-bromothieno[2,3-b]pyridine-2-carboxylate Chemical compound C1=CC=C2C(Br)=C(C(=O)OCC)SC2=N1 SFDIRKDBTVHEEY-UHFFFAOYSA-N 0.000 description 3
210000004072 lung Anatomy 0.000 description 3
239000000203 mixture Substances 0.000 description 3
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical group CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 2
NNHOXSZGHYROQO-UHFFFAOYSA-N 3-bromothieno[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=CC=C2C(Br)=C(C(=O)O)SC2=N1 NNHOXSZGHYROQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
241000700647 Variola virus Species 0.000 description 2
241000700605 Viruses Species 0.000 description 2
239000008272 agar Substances 0.000 description 2
238000005915 ammonolysis reaction Methods 0.000 description 2
230000000840 anti-viral effect Effects 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
IGNOIXRUJYCWDS-UHFFFAOYSA-N cyanomethyl 2-(cyanomethylsulfanyl)pyridine-3-carboxylate Chemical compound N#CCOC(=O)C1=CC=CN=C1SCC#N IGNOIXRUJYCWDS-UHFFFAOYSA-N 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
229950001902 dimevamide Drugs 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000006186 oral dosage form Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000007505 plaque formation Effects 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 2
229910001950 potassium oxide Inorganic materials 0.000 description 2
230000002265 prevention Effects 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000002636 symptomatic treatment Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000011287 therapeutic dose Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
229960005486 vaccine Drugs 0.000 description 2
VSUIAFYDBFDVDV-UHFFFAOYSA-N 3-bromothieno[3,2-b]pyridine-2-carbonitrile Chemical compound C1=CN=C2C(Br)=C(C#N)SC2=C1 VSUIAFYDBFDVDV-UHFFFAOYSA-N 0.000 description 1
IKQJCFYKKWWOIS-UHFFFAOYSA-N 3-chlorothieno[2,3-b]pyridine-2-carbonitrile Chemical compound C1=CC=C2C(Cl)=C(C#N)SC2=N1 IKQJCFYKKWWOIS-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
208000005100 Herpetic Keratitis Diseases 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
241000712431 Influenza A virus Species 0.000 description 1
241000282560 Macaca mulatta Species 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
206010028735 Nasal congestion Diseases 0.000 description 1
206010073938 Ophthalmic herpes simplex Diseases 0.000 description 1
241000709664 Picornaviridae Species 0.000 description 1
208000036071 Rhinorrhea Diseases 0.000 description 1
206010039101 Rhinorrhoea Diseases 0.000 description 1
206010039105 Rhinoviral infections Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 description 1
208000036142 Viral infection Diseases 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
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000002832 anti-viral assay Methods 0.000 description 1
230000000890 antigenic effect Effects 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
238000009835 boiling Methods 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
239000002775 capsule Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
TTZUCVNWOZLIGL-UHFFFAOYSA-N chembl362994 Chemical compound C1=CC=C2N(C)C(O)=C(N=NC(S)=N)C2=C1 TTZUCVNWOZLIGL-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
208000030499 combat disease Diseases 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229960004716 idoxuridine Drugs 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000012678 infectious agent Substances 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
244000000056 intracellular parasite Species 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
GFWOMJATTSHQFM-UHFFFAOYSA-N n-ethyl-2-propan-2-ylcycloheptane-1-carboxamide Chemical compound CCNC(=O)C1CCCCCC1C(C)C GFWOMJATTSHQFM-UHFFFAOYSA-N 0.000 description 1
238000002663 nebulization Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
206010041232 sneezing Diseases 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000007944 thiolates Chemical group 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
229960003636 vidarabine Drugs 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO790778A 1978-03-10 1979-03-08 Fremgangsmaate ved fremstilling av antirhinovirale midler NO790778L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US88525278A	1978-03-10	1978-03-10
US05/970,732 US4220776A (en)	1978-12-21	1978-12-21	N-(Pyridothienopyrazol)amides

Publications (1)

Publication Number	Publication Date
NO790778L true NO790778L (no)	1979-09-11

Family

ID=27128754

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO790778A NO790778L (no)	1978-03-10	1979-03-08	Fremgangsmaate ved fremstilling av antirhinovirale midler

Country Status (18)

Country	Link
EP (1)	EP0004319B1 (de)
JP (1)	JPS54145698A (de)
AR (1)	AR221612A1 (de)
AT (1)	AT369370B (de)
AU (1)	AU522953B2 (de)
CA (1)	CA1114372A (de)
DE (1)	DE2960549D1 (de)
DK (1)	DK28979A (de)
ES (1)	ES478502A1 (de)
FI (1)	FI790818A7 (de)
GR (1)	GR66657B (de)
HU (1)	HU179006B (de)
IL (1)	IL56828A (de)
NO (1)	NO790778L (de)
NZ (1)	NZ189870A (de)
PH (1)	PH14896A (de)
PT (1)	PT69319A (de)
SU (1)	SU745368A3 (de)

1979
- 1979-01-23 DK DK28979A patent/DK28979A/da unknown
- 1979-03-07 AU AU44881/79A patent/AU522953B2/en not_active Ceased
- 1979-03-07 CA CA322,910A patent/CA1114372A/en not_active Expired
- 1979-03-07 SU SU792734256A patent/SU745368A3/ru active
- 1979-03-08 PT PT69319A patent/PT69319A/pt unknown
- 1979-03-08 DE DE7979100705T patent/DE2960549D1/de not_active Expired
- 1979-03-08 NO NO790778A patent/NO790778L/no unknown
- 1979-03-08 PH PH22265A patent/PH14896A/en unknown
- 1979-03-08 EP EP79100705A patent/EP0004319B1/de not_active Expired
- 1979-03-09 ES ES478502A patent/ES478502A1/es not_active Expired
- 1979-03-09 JP JP2817479A patent/JPS54145698A/ja active Pending
- 1979-03-09 NZ NZ189870A patent/NZ189870A/xx unknown
- 1979-03-09 FI FI790818A patent/FI790818A7/fi not_active Application Discontinuation
- 1979-03-09 GR GR58555A patent/GR66657B/el unknown
- 1979-03-09 HU HU79DU301A patent/HU179006B/hu unknown
- 1979-03-09 IL IL56828A patent/IL56828A/xx unknown
- 1979-03-09 AT AT0179679A patent/AT369370B/de not_active IP Right Cessation
- 1979-03-18 AR AR275757A patent/AR221612A1/es active

Also Published As

Publication number	Publication date
AU522953B2 (en)	1982-07-01
FI790818A7 (fi)	1979-09-11
PH14896A (en)	1982-01-08
GR66657B (de)	1981-04-07
IL56828A0 (en)	1979-05-31
AT369370B (de)	1982-12-27
DK28979A (da)	1979-09-11
AU4488179A (en)	1979-09-13
AR221612A1 (es)	1981-02-27
HU179006B (en)	1982-08-28
NZ189870A (en)	1981-07-13
PT69319A (en)	1979-04-01
DE2960549D1 (en)	1981-11-05
ATA179679A (de)	1982-05-15
ES478502A1 (es)	1980-07-01
EP0004319A1 (de)	1979-10-03
JPS54145698A (en)	1979-11-14
SU745368A3 (ru)	1980-06-30
EP0004319B1 (de)	1981-08-05
IL56828A (en)	1981-12-31
CA1114372A (en)	1981-12-15

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AU2009313134B8 (en)	2015-05-28	Novel halogen-substituted compounds
EP1569919B1 (de)	2012-04-18	Nicht-nukleosidische reverse-transkriptase-inhibitoren
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WO2010133312A1 (de)	2010-11-25	Halogen-substituierte verbindungen als pestizide
JPS61148178A (ja)	1986-07-05	チエニルチアゾ−ル化合物
NO164349B (no)	1990-06-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive n-(piperidinyl-alkyl)-karboksamider og deres salter.
JP5902172B2 (ja)	2016-04-13	広範囲のインフルエンザ抗ウイルス薬としての新規ピペラジン類似体
EP0005357B1 (de)	1983-02-09	N-(Benzothienopyrazol)amide und diese enthaltende Arzneimittel
AU2005219689A1 (en)	2005-09-15	Novel cyclic compound having 4-pyridylalkylthio group having (un)substituted amino introduced therein
US4220776A (en)	1980-09-02	N-(Pyridothienopyrazol)amides
NO780059L (no)	1978-07-10	Fremgangsmaate til fremstilling av terapeutisk virksomme forbindelser og preparater inneholdende disse
NO790778L (no)	1979-09-11	Fremgangsmaate ved fremstilling av antirhinovirale midler
EP2933254B1 (de)	2021-01-20	Neuartige verbindung, pharmazeutisch verträgliches salz und optisches isomer davon, verfahren zur herstellung davon und pharmazeutische zusammensetzung zur prävention oder behandlung von viruserkrankungen damit als wirkstoff
WO2011061277A1 (en)	2011-05-26	Amino aryl acetamides and their use in the treatment of malaria
DK142767B (da)	1981-01-19	Analogifremgangsmåde til fremstilling af 1- og dl-(racem-)formerne af derivater af 6-(m-aminophenyl)-2,3,5,6-tetrahydroimidazo(2,1-b)thiazol.
FI60712B (fi)	1981-11-30	Foerfarande foer framstaellning av 6-(m-(6-halogennikotinoylamino)fenyl)- eller 6-(m-(6-halogenisonikotinoylamino)fenyl)-2,3,5,6-tetrahydroimidazo-(2,1-b)tiazol anvaendbar som maskmedel
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HK40059923B (en)	2025-09-19	Compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient
HK40059923A (en)	2022-05-13	Compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient
JP2912007B2 (ja)	1999-06-28	５，１１―ジヒドロ―６Ｈ―ジピリド〔３，２―ｂ：２′，３′―ｅ〕〔１，４〕ジアゼピンおよび該化合物を含有するＨＩＶ感染の予防又は治療用組成物
HK1216253B (en)	2021-08-20	Novel compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient
DK141121B (da)	1980-01-21	Analogifremgangsmåde til fremstilling af 2,3-dihydro-1-benzothiepin-4-carboxylsyreamider eller terapeutisk anvendelige salte deraf med baser.