CA1071626A - Imidazolylquinazoline derivatives - Google Patents
Imidazolylquinazoline derivativesInfo
- Publication number
- CA1071626A CA1071626A CA252,103A CA252103A CA1071626A CA 1071626 A CA1071626 A CA 1071626A CA 252103 A CA252103 A CA 252103A CA 1071626 A CA1071626 A CA 1071626A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- group
- lower alkyl
- compound
- sulphur
- Prior art date
- 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
Links
- VRGOEZCWGBOGCA-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)quinazoline Chemical class C1=CNC(C=2N=C3C=CC=CC3=CN=2)=N1 VRGOEZCWGBOGCA-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000005864 Sulphur Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- -1 piperazino Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- 241000204031 Mycoplasma Species 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000003096 antiparasitic agent Substances 0.000 abstract description 2
- 229940125687 antiparasitic agent Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 230000003569 amebicidal effect Effects 0.000 description 4
- 230000001572 anti-trichomonad Effects 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000224489 Amoeba Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000202956 Mycoplasma arthritidis Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 230000002141 anti-parasite Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HDJUKQSJBOLUKY-UHFFFAOYSA-N 2-(1-methyl-5-nitroimidazol-2-yl)-1h-quinazolin-4-one Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC2=CC=CC=C2C(=O)N1 HDJUKQSJBOLUKY-UHFFFAOYSA-N 0.000 description 1
- YGDXCSXCXZEVMW-UHFFFAOYSA-N 2-[2-[2-(1-methyl-5-nitroimidazol-2-yl)quinazolin-4-yl]oxyethylamino]ethanol Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC(OCCNCCO)=C(C=CC=C2)C2=N1 YGDXCSXCXZEVMW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RVRFUCQSUAQDHE-UHFFFAOYSA-N 4-chloro-2-(1-methyl-5-nitroimidazol-2-yl)quinazoline Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC(Cl)=C(C=CC=C2)C2=N1 RVRFUCQSUAQDHE-UHFFFAOYSA-N 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- 102100025172 Calpain-1 catalytic subunit Human genes 0.000 description 1
- 101710124171 Calpain-1 catalytic subunit Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 241000224432 Entamoeba histolytica Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000204022 Mycoplasma gallisepticum Species 0.000 description 1
- 241000204048 Mycoplasma hominis Species 0.000 description 1
- 241000202938 Mycoplasma hyorhinis Species 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH604175A CH612432A5 (en, 2012) | 1975-05-12 | 1975-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071626A true CA1071626A (en) | 1980-02-12 |
Family
ID=4303274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA252,103A Expired CA1071626A (en) | 1975-05-12 | 1976-05-10 | Imidazolylquinazoline derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4055642A (en, 2012) |
| JP (1) | JPS51138689A (en, 2012) |
| AT (1) | ATA342176A (en, 2012) |
| AU (1) | AU1389176A (en, 2012) |
| BE (1) | BE841669A (en, 2012) |
| CA (1) | CA1071626A (en, 2012) |
| CH (2) | CH612432A5 (en, 2012) |
| DE (1) | DE2619110A1 (en, 2012) |
| DK (1) | DK197476A (en, 2012) |
| ES (1) | ES447751A1 (en, 2012) |
| FI (1) | FI761232A7 (en, 2012) |
| FR (1) | FR2310756A1 (en, 2012) |
| GB (1) | GB1551117A (en, 2012) |
| IL (1) | IL49546A0 (en, 2012) |
| NL (1) | NL7604894A (en, 2012) |
| NO (1) | NO761537L (en, 2012) |
| PT (1) | PT65084B (en, 2012) |
| SE (1) | SE409455B (en, 2012) |
| ZA (1) | ZA762813B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2826526A1 (de) * | 1977-06-17 | 1979-01-04 | Gist Brocades Nv | Kupferkomplexe von phenanthrolin-, isochinolin- und chinazolinderivaten, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von mykoplasmainfektionen |
| GB8429739D0 (en) * | 1984-11-24 | 1985-01-03 | Fbc Ltd | Fungicides |
| JP2657760B2 (ja) * | 1992-07-15 | 1997-09-24 | 小野薬品工業株式会社 | ４−アミノキナゾリン誘導体およびそれを含有する医薬品 |
| AU5261001A (en) | 2000-04-27 | 2001-11-12 | Imperial Cancer Research Technology Ltd | Condensed heteroaryl derivatives |
| CL2004000409A1 (es) * | 2003-03-03 | 2005-01-07 | Vertex Pharma | Compuestos derivados de 2-(cilo sustituido)-1-(amino u oxi sustituido)-quinazolina, inhibidores de canales ionicos de sodio y calcio dependientes de voltaje; composicion farmaceutica; y uso del compuesto en el tratamiento de dolor agudo, cronico, neu |
| CA2528774A1 (en) * | 2003-06-20 | 2005-01-27 | Coley Pharmaceutical Gmbh | Small molecule toll-like receptor (tlr) antagonists |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3324122A (en) * | 1964-12-14 | 1967-06-06 | Norwich Pharma Co | Series of 4-substituted-2-(5-nitro-2-furyl) quinazolines |
| US3705898A (en) * | 1970-01-26 | 1972-12-12 | Morton Norwich Products Inc | Certain 4 - amino - 2-(5-nitro-2-thienyl) quinazolines and the intermediate 4 - chloro-(5 - nitro-2-thienyl)quinazolines therefor |
| BE795636A (fr) * | 1972-02-19 | 1973-08-20 | Schering Ag | Nitroimidazolylpyrimidines, et leur procede de preparation |
-
1975
- 1975-05-12 CH CH604175A patent/CH612432A5/xx not_active IP Right Cessation
-
1976
- 1976-05-03 FI FI761232A patent/FI761232A7/fi not_active Application Discontinuation
- 1976-05-03 DE DE19762619110 patent/DE2619110A1/de not_active Withdrawn
- 1976-05-03 DK DK197476A patent/DK197476A/da unknown
- 1976-05-04 NO NO761537A patent/NO761537L/no unknown
- 1976-05-05 SE SE7605158A patent/SE409455B/xx unknown
- 1976-05-05 US US05/683,291 patent/US4055642A/en not_active Expired - Lifetime
- 1976-05-07 GB GB18778/76A patent/GB1551117A/en not_active Expired
- 1976-05-07 NL NL7604894A patent/NL7604894A/xx unknown
- 1976-05-10 ES ES447751A patent/ES447751A1/es not_active Expired
- 1976-05-10 IL IL49546A patent/IL49546A0/xx unknown
- 1976-05-10 BE BE166912A patent/BE841669A/xx unknown
- 1976-05-10 CA CA252,103A patent/CA1071626A/en not_active Expired
- 1976-05-10 PT PT65084A patent/PT65084B/pt unknown
- 1976-05-11 AT AT342176A patent/ATA342176A/de not_active Application Discontinuation
- 1976-05-11 JP JP51053730A patent/JPS51138689A/ja active Pending
- 1976-05-12 AU AU13891/76A patent/AU1389176A/en not_active Expired
- 1976-05-12 FR FR7614235A patent/FR2310756A1/fr active Granted
- 1976-05-12 ZA ZA762813A patent/ZA762813B/xx unknown
-
1978
- 1978-12-13 CH CH1267878A patent/CH617691A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2310756A1 (fr) | 1976-12-10 |
| FR2310756B1 (en, 2012) | 1978-10-20 |
| ZA762813B (en) | 1977-12-28 |
| SE7605158L (sv) | 1976-11-13 |
| SE409455B (sv) | 1979-08-20 |
| ATA342176A (de) | 1980-08-15 |
| AU1389176A (en) | 1977-11-17 |
| US4055642A (en) | 1977-10-25 |
| BE841669A (fr) | 1976-11-10 |
| GB1551117A (en) | 1979-08-22 |
| FI761232A7 (en, 2012) | 1976-11-13 |
| CH617691A5 (en, 2012) | 1980-06-13 |
| NO761537L (en, 2012) | 1976-11-15 |
| DK197476A (da) | 1976-11-13 |
| CH612432A5 (en, 2012) | 1979-07-31 |
| PT65084B (fr) | 1978-02-06 |
| ES447751A1 (es) | 1977-10-01 |
| NL7604894A (nl) | 1976-11-16 |
| DE2619110A1 (de) | 1976-11-25 |
| JPS51138689A (en) | 1976-11-30 |
| PT65084A (fr) | 1976-06-01 |
| IL49546A0 (en) | 1976-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |