NO165147B - 1h-imidazo(4,5-c)-kinolin-5-oxydforbindelser. - Google Patents
1h-imidazo(4,5-c)-kinolin-5-oxydforbindelser. Download PDFInfo
- Publication number
- NO165147B NO165147B NO890824A NO890824A NO165147B NO 165147 B NO165147 B NO 165147B NO 890824 A NO890824 A NO 890824A NO 890824 A NO890824 A NO 890824A NO 165147 B NO165147 B NO 165147B
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- alkyl
- quinoline
- imidazo
- phenyl
- Prior art date
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- -1 (phenyl)-ethyl Chemical group 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- RBKTVDLDAPUNMV-UHFFFAOYSA-N 1-(2-methylpropyl)-5-oxidoimidazo[4,5-c]quinolin-5-ium Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C[N+]([O-])=C21 RBKTVDLDAPUNMV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- JFMKIQOIIMSWIM-UHFFFAOYSA-N 4-n-(2-methylpropyl)quinoline-3,4-diamine Chemical compound C1=CC=C2C(NCC(C)C)=C(N)C=NC2=C1 JFMKIQOIIMSWIM-UHFFFAOYSA-N 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 239000006184 cosolvent Substances 0.000 claims 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- DCKDJXAYJHREKA-UHFFFAOYSA-N 2-imidazo[4,5-c]quinolin-1-ylethyl benzoate Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1CCOC(=O)C1=CC=CC=C1 DCKDJXAYJHREKA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ARBYUNTVRNFIQO-UHFFFAOYSA-N (2-acetyloxy-3-imidazo[4,5-c]quinolin-1-ylpropyl) acetate Chemical compound C1=CC=CC2=C3N(CC(COC(=O)C)OC(C)=O)C=NC3=CN=C21 ARBYUNTVRNFIQO-UHFFFAOYSA-N 0.000 description 1
- CXYOCSTZCULCAE-UHFFFAOYSA-N 1-(2-methylpropyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=CN=C21 CXYOCSTZCULCAE-UHFFFAOYSA-N 0.000 description 1
- CPPIRAFONZTAOX-UHFFFAOYSA-N 2-(5-oxidoimidazo[4,5-c]quinolin-5-ium-1-yl)ethyl benzoate Chemical compound C1=2C3=CC=CC=C3[N+]([O-])=CC=2N=CN1CCOC(=O)C1=CC=CC=C1 CPPIRAFONZTAOX-UHFFFAOYSA-N 0.000 description 1
- HKIWBOKRKRFJNV-UHFFFAOYSA-N 2-imidazo[4,5-c]quinolin-1-ylethanol Chemical compound C1=CC=CC2=C3N(CCO)C=NC3=CN=C21 HKIWBOKRKRFJNV-UHFFFAOYSA-N 0.000 description 1
- FFWPANGYEXMAAS-UHFFFAOYSA-N 3-imidazo[4,5-c]quinolin-1-ylpropane-1,2-diol Chemical compound C1=CC=CC2=C3N(CC(O)CO)C=NC3=CN=C21 FFWPANGYEXMAAS-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- XEKYEOYIBDYIGT-UHFFFAOYSA-N C12=CC=CC=C2[N+]([O-])=CC2=C1NC=N2 Chemical class C12=CC=CC=C2[N+]([O-])=CC2=C1NC=N2 XEKYEOYIBDYIGT-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Physical Water Treatments (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Alarm Systems (AREA)
- Quinoline Compounds (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Luminescent Compositions (AREA)
Description
Foreliggende oppfinnelse angår hittil ukjente lH-imidazo[4,5-c]kinolin-5-oxyd-forbindelser som er kjenne-tegnet ved at de har generell formel
hvori Rg er valgt fra alkyl med 1 til 10 carbonatomer, cyclohexylmethyl, hydroxyalkyl med 1 til 6 carbonatomer, acyloxyalkyl hvori acyloxygruppen er alkanoyloxy med 2 til 4 carbonatomer eller benzoyloxy, og alkylgruppen inneholder 1 til 6 carbonatomer, benzyl, (fenyl)-ethyl og fenyl, hvori benzyl-, (fenyl)-ethyl-eller fenyl-substituenten eventuelt er substituert i benzenringen med 1 eller 2 grupper uavhengig valgt fra alkyl med 1 til 4 carbonatomer, alkylalkanoat hvori alkylgruppen har 1
til 4 carbonatomer, og alkanoatgruppen inneholder 2 til
4 carbonatomer, alkoxy med 1 til 4 carbonatomer og halogen, forutsatt at hvis benzenringen er substituert med 2 av de nevnte grupper, inneholder disse grupper tilsammen ikke mer enn 6 carbonatomer; Rg er valgt fra hydrogen og alkyl med 1 til 8 carbonatomer; og hver gruppe R,, er uavhengig valgt fra alkyl med 1 til 4 carbonatomer, og n er et helt tall 0-2, forutsatt at hvis n er 2, inneholder substituentene R,.
tilsammen ikke mer enn 6 carbonatomer.
Forbindelsene av formel XXII er anvendbare mellomprodukter ved fremstilling av forbindelser med formel I og enkelte av forbindelsene av formel II, som beskrevet i norske ålment tilgjengelige søknader 844565 og 890822.
i Forbindelsene av generell formel XXII fremstilles ved oxydasjon av forbindelser av generell formel VII
med et typisk oxydasjonsmiddel som anvendes for dannelse av N-oxyder. Egnede oxydasjonsmidler innbefatter persyre og hydrogenperoxyd. Oxydasjonsreaksjonen utføres fortrinnsvis i iseddik. Oppvarming anvendes vanligvis for å akselerere reaksjonshastigheten.
Oppfinnelsen illustreres nærmere i de etterfølgende eksempler.
Eksempel 1
Fremstilling av en forbindelse av formel XXII
Til en oppløsning av 9,3 g (0,0413 mol) 1-isobutyl-lH-imidazo[4,5-c]kinolin i 150 ml eddiksyre ble tilsatt 1,5 ekvivalenter (0,062 mol) 30 % hydrogenperoxyd. 'Blahdingen ble oppvarmet til 54 - 70° C i 1 dag og ble deretter inndampet. Residuet ble nøytralisert med mettet natriumbicar-bonatløsning, og den resulterende blanding ble ekstrahert med diklormethan. Ekstrakene ble tørket og deretter inndampet under dannelse av et residuum som størknet gradvis til et gult fast stoff, 1-isobutyl-lH-imidazo[4,5-c]kinolin-5-oxyd. Dette produkt ble omkrystallisert to ganger fra ethylacetat under dannelse av et grønt fast stoff, sm.p. 211 - 213° C.
Analyse for ci4<Hi>5N30:
Under anvendelse av metoden beskrevet i eksemplet, ble de forbindelser av formel XXII vist i etterfølgende tabell I, fremstilt.
Eksempel 2
Del A
Til en omrørt, kald (5° C) blanding av 29,1 g (0,136 mol) 1-(2-hydroxyethyl)-lH-imidazo[4,5-c]kinolin
(fra eksempel 52) og 500 ml pyridin ble i små porsjoner tilsatt 23,9 g (0,17 mol) benzoylklorid. Blandingen fikk opp-varmes langsomt til 20° C og ble deretter omrørt i 18 timer ved 20° C. Løsningen ble inndampet og vann ble tilsatt til residuet. Det faste stoff ble fraskilt ved filtrering, vasket med vann og ble omkrystallisert fra en 50:50 ethylacetat/hexan-blanding. Omkrystallisering fra ethylacetat og igjen fra ethanol ga hvite krystaller av 1-(2-benzoyloxy-ethyl) -lH-imidazo [4 , 5-c ]kinolin, sm.p. 149 - 151° C. Analyse: for C^9<H>^5<N>3°2:
Beregnet: C 71,9 H 4,8 N 13,2 %
Funnet : C 71,8 H 4,6 N 13,2 %
Del B
En blanding av 67,5 g (0,213 mol) l-(2-benzoyloxyethyl)-lH-imidazo[4,5-c]kinolin, 36,3 g (0,32 mol) 30 % hydrogenperoxyd og 450 ml iseddik ble oppvarmet til 65° C i 2 dager under omrøring. Løsningen ble deretter inndampet i vakuum og residuet ble tilsatt til vann. Blandingen ble nøytralisert med vandig natrium-hydroxydløsning og natriumbicarbonat. Det faste stoff ble fraskilt ved filtrering, vasket med vann og ble omkrystallisert fra methanol under dannelse av et brunt fast stoff, 1-(2-benzoyloxyethyl)-lH-imidazo[4,5-c]kinolin-5-oxyd.
Eksempel 3
Del A
Under anvendelse av metoden ifølge eksempel 2A ble benzoylklorid omsatt med 1-(2,3-dihydroxypropyl)-1H-imidazo [4 ,5-c JkinoMn (fra eksempel 70) under dannelse av 1-(2,3-dibenzoyloxypropyl)-lH-iraidazo[4,5-cJkinolin.
Del B
Det urene produkt fra del A ble omsatt med hydrogenperoxyd etter metoden beskrevet i eksempel 120 under dannelse av 1-(2,3-dibemzoyloxypropyl)-lH-imidazo[4,5-c]kinblin-5-oxyd som et blekgult fast stoff som smeltet ved 73 - 82° C.
Eksempel 4
Del A
1-(2,3-dihydroxypropyl)-lH-imidazo[4,5-c]kinolin ble omsatt med overskudd av eddiksyreanhydrid under dannelse av 1-(2,3-diacetoxypropyl)-lH-imidazo[4,5-c]-kinolin.
Del B
Produktet fra del A ble omsatt med hydrogenperoxyd etter metoden beskrevet i eksempel 2B under dannelse av 1-(2,3-diacetoxypropyl)-lH-imidazo[4,5-c]kirolin-5-oxyd som et brungult fast stoff hvor smeltepunktet for det urene mate-riale var 84 - 86° C.
Under anvendelse av den tidligere beskrevne metode, ble de mellomprodukter av formel XXII som er vist i etterfølgende tabell II, fremstilt.
Claims (1)
- Eksempel 5Til 10,0 g (0,0464 mol) 3-amino-4-(isobutylamino)-kinolin ble tilsatt 9,0 g (0,0604 mol) triethylorthoformiat, og blandingen ble oppvarmet til 125 - 130°C i 3 timer. Blandingen fikk deretter av-kjøles til romtemperatur, og 30 ml iseddik og 7,9 g (0,0696 mol) 30 % hydrogenperoxydløsning ble tilsatt. Den resulterende blanding ble oppvarmet til 68 - 70° C på et oljebad i 24 timer. Iseddiken ble fjernet ved azeotrop destillasjon under anvendelse av heptan som ko-løsningsmid-del. Mettet natriumbicarbonatløsning ble tilsatt til residuet for å nøytralisere dette. Det beige-farvede faste stoff som ble utfelt ble filtrert fra, vasket med vann og tørket under dannelse av 10,0 g urent 1-isobutyl-lH-imidazo-[4,5-c]kinolin-5-oxyd. Dette faste stoff ble oppslemmet i litt kald aceton og ble fraskilt ved filtrering, vasket og tørket under dannelse av 6,2 g renset produkt med sirup. 205 - 209° C.lH-imidazo[4,5-c]kinolin-5-oxyd-forbindelser,karakterisert ved at de har generell formel hvori R6 er valgt fra alkyl med 1 til 10 carbonatomer, cyclohexylmethyl, hydroxyalkyl med 1 til 6 carbonatomer, acyloxyalkyl hvoriacyloxygruppen er alkanoyloxy med 2 til 4 carbonatomer eller benzoyloxy, og alkylgruppen inneholder 1 til 6 carbonatomer, benzyl, (fenyl)-ethyl og fenyl, hvori benzyl-, (fenyl)-ethyl-eller fenyl-substituenten eventuelt er substituert i benzenringen med 1 eller 2 grupper uavhengig valgt fra alkyl med 1 til 4 carbonatomer, alkylalkanoat hvori alkylgruppen har 1 til 4 carbonatomer, og alkanoatgruppen inneholder 2 til 4 carbonatomer, alkoxy med 1 til 4 carbonatomer og halogen, forutsatt at hvis benzenringen er substituert med 2 av de nevnte grupper, inneholder disse grupper tilsammen ikke mer enn 6 carbonatomer; Rg er valgt fra hydrogen og alkyl med 1 til 8 carbonatomer; og hver gruppe R,- er uavhengig valgt fra alkyl med 1 til 4 carbonatomer, og n er et helt tall 0-2, forutsatt at hvis n er 2, inneholder substituentene R^ tilsammen ikke mer enn 6 carbonatomer.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO890824A NO165147C (no) | 1983-11-18 | 1989-02-27 | 1h-imidazo(4,5-c)-kinolin-5-oxydforbindelser. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US55315783A | 1983-11-18 | 1983-11-18 | |
US55315883A | 1983-11-18 | 1983-11-18 | |
NO844565A NO163819C (no) | 1983-11-18 | 1984-11-15 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 1h-imidazo(4,5-c)kinolin og derivater derav. |
NO890824A NO165147C (no) | 1983-11-18 | 1989-02-27 | 1h-imidazo(4,5-c)-kinolin-5-oxydforbindelser. |
Publications (4)
Publication Number | Publication Date |
---|---|
NO890824L NO890824L (no) | 1985-05-20 |
NO890824D0 NO890824D0 (no) | 1989-02-27 |
NO165147B true NO165147B (no) | 1990-09-24 |
NO165147C NO165147C (no) | 1991-01-02 |
Family
ID=27070262
Family Applications (7)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO844565A NO163819C (no) | 1983-11-18 | 1984-11-15 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 1h-imidazo(4,5-c)kinolin og derivater derav. |
NO890824A NO165147C (no) | 1983-11-18 | 1989-02-27 | 1h-imidazo(4,5-c)-kinolin-5-oxydforbindelser. |
NO890823A NO165146C (no) | 1983-11-18 | 1989-02-27 | 1h-imidazo-(4,5-c)-kinolin-4-klorforbindelser. |
NO890822A NO165145C (no) | 1983-11-18 | 1989-02-27 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 1h-imidazo-(4,5-c)-kinolin-4-aminderivater. |
NO890826A NO168705C (no) | 1983-11-18 | 1989-02-27 | 3-nitro-kinoliner. |
NO890825A NO169437C (no) | 1983-11-18 | 1989-02-27 | 3-amino-kinoliner. |
NO1999015C NO1999015I1 (no) | 1983-11-18 | 1999-07-08 | Imiquimod |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO844565A NO163819C (no) | 1983-11-18 | 1984-11-15 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 1h-imidazo(4,5-c)kinolin og derivater derav. |
Family Applications After (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO890823A NO165146C (no) | 1983-11-18 | 1989-02-27 | 1h-imidazo-(4,5-c)-kinolin-4-klorforbindelser. |
NO890822A NO165145C (no) | 1983-11-18 | 1989-02-27 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 1h-imidazo-(4,5-c)-kinolin-4-aminderivater. |
NO890826A NO168705C (no) | 1983-11-18 | 1989-02-27 | 3-nitro-kinoliner. |
NO890825A NO169437C (no) | 1983-11-18 | 1989-02-27 | 3-amino-kinoliner. |
NO1999015C NO1999015I1 (no) | 1983-11-18 | 1999-07-08 | Imiquimod |
Country Status (15)
Country | Link |
---|---|
EP (2) | EP0145340B1 (no) |
JP (1) | JPS60123488A (no) |
KR (1) | KR900005657B1 (no) |
AT (2) | ATE84525T1 (no) |
AU (2) | AU581190B2 (no) |
CA (1) | CA1271477A (no) |
DE (3) | DE19975027I2 (no) |
DK (6) | DK164280C (no) |
ES (1) | ES537677A0 (no) |
IE (1) | IE57874B1 (no) |
IL (2) | IL84537A (no) |
NL (2) | NL980041I2 (no) |
NO (7) | NO163819C (no) |
NZ (1) | NZ210228A (no) |
PH (1) | PH22338A (no) |
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CA2653941C (en) | 2006-05-31 | 2013-01-08 | The Regents Of The University Of California | Substituted amino purine derivatives and uses thereof |
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US3700674A (en) * | 1969-04-30 | 1972-10-24 | American Cyanamid Co | 4-alkylamino-3-nitroquinolines |
ZA832938B (en) * | 1982-05-03 | 1984-12-24 | Lilly Co Eli | 2-phenylimidazo(4,5-c)pyridines |
-
1984
- 1984-11-13 CA CA000467706A patent/CA1271477A/en not_active Expired - Lifetime
- 1984-11-14 AU AU35402/84A patent/AU581190B2/en not_active Expired
- 1984-11-15 DK DK542684A patent/DK164280C/da not_active IP Right Cessation
- 1984-11-15 ES ES537677A patent/ES537677A0/es active Granted
- 1984-11-15 NO NO844565A patent/NO163819C/no not_active IP Right Cessation
- 1984-11-16 EP EP84307974A patent/EP0145340B1/en not_active Expired - Lifetime
- 1984-11-16 DE DE1999175027 patent/DE19975027I2/de active Active
- 1984-11-16 IE IE2952/84A patent/IE57874B1/en not_active IP Right Cessation
- 1984-11-16 PH PH31451A patent/PH22338A/en unknown
- 1984-11-16 EP EP88116137A patent/EP0310950B1/en not_active Expired - Lifetime
- 1984-11-16 AT AT88116137T patent/ATE84525T1/de not_active IP Right Cessation
- 1984-11-16 DE DE8888116137T patent/DE3486043T2/de not_active Expired - Lifetime
- 1984-11-16 AT AT84307974T patent/ATE49763T1/de active
- 1984-11-16 NZ NZ210228A patent/NZ210228A/xx unknown
- 1984-11-16 IL IL84537A patent/IL84537A/xx not_active IP Right Cessation
- 1984-11-16 DE DE8484307974T patent/DE3481124D1/de not_active Expired - Lifetime
- 1984-11-17 JP JP59243142A patent/JPS60123488A/ja active Granted
- 1984-11-17 KR KR1019840007224A patent/KR900005657B1/ko not_active IP Right Cessation
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1987
- 1987-11-19 IL IL84537A patent/IL84537A0/xx unknown
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1989
- 1989-02-14 AU AU29911/89A patent/AU611997B2/en not_active Expired
- 1989-02-27 NO NO890824A patent/NO165147C/no not_active IP Right Cessation
- 1989-02-27 NO NO890823A patent/NO165146C/no not_active IP Right Cessation
- 1989-02-27 NO NO890822A patent/NO165145C/no not_active IP Right Cessation
- 1989-02-27 NO NO890826A patent/NO168705C/no not_active IP Right Cessation
- 1989-02-27 NO NO890825A patent/NO169437C/no not_active IP Right Cessation
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1991
- 1991-07-16 DK DK135891A patent/DK164455C/da not_active IP Right Cessation
- 1991-07-16 DK DK136191A patent/DK164452C/da not_active IP Right Cessation
- 1991-07-16 DK DK135791A patent/DK169179B1/da not_active IP Right Cessation
- 1991-07-16 DK DK136091A patent/DK164451C/da not_active IP Right Cessation
- 1991-07-16 DK DK135991A patent/DK165921C/da not_active IP Right Cessation
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1998
- 1998-12-14 NL NL980041C patent/NL980041I2/nl unknown
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1999
- 1999-07-08 NO NO1999015C patent/NO1999015I1/no unknown
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