US3324122A - Series of 4-substituted-2-(5-nitro-2-furyl) quinazolines - Google Patents
Series of 4-substituted-2-(5-nitro-2-furyl) quinazolines Download PDFInfo
- Publication number
- US3324122A US3324122A US418311A US41831164A US3324122A US 3324122 A US3324122 A US 3324122A US 418311 A US418311 A US 418311A US 41831164 A US41831164 A US 41831164A US 3324122 A US3324122 A US 3324122A
- Authority
- US
- United States
- Prior art keywords
- mole
- compound
- mixture
- furyl
- solution
- 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 - Lifetime
Links
- -1 4-substituted-2-(5-nitro-2-furyl) quinazolines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ADYNJDNYIVZXNK-UHFFFAOYSA-N quinazoline;dihydrochloride Chemical compound Cl.Cl.N1=CN=CC2=CC=CC=C21 ADYNJDNYIVZXNK-UHFFFAOYSA-N 0.000 description 2
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 description 1
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 1
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- AUEOHSUMWXAPBX-UHFFFAOYSA-N nifurquinazol Chemical compound N=1C2=CC=CC=C2C(N(CCO)CCO)=NC=1C1=CC=C([N+]([O-])=O)O1 AUEOHSUMWXAPBX-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US418311A US3324122A (en) | 1964-12-14 | 1964-12-14 | Series of 4-substituted-2-(5-nitro-2-furyl) quinazolines |
| IL24359A IL24359A (en) | 1964-12-14 | 1965-09-23 | 4-substituted-2-(5-nitro-2-furyl)-quinazolines and a process for their production |
| ES0318292A ES318292A1 (es) | 1964-12-14 | 1965-10-08 | Metodo de preparacion de 2-(5-nitro-2-furil) quinazolinas 4sustituidas. |
| DE19651620076 DE1620076A1 (de) | 1964-12-14 | 1965-10-13 | Verfahren zur Herstellung von neuen 2-(5-Nitro-2-furyl)-chinazolinen |
| SE13375/65A SE325579B (de) | 1964-12-14 | 1965-10-15 | |
| DK535765AA DK117902B (da) | 1964-12-14 | 1965-10-20 | Fremangsmåde til fremstilling af 4-substituerede 2-(5-nitro-2-furyl)-kinazoliner eller syreadditionssalte deraf. |
| NL6513634A NL6513634A (de) | 1964-12-14 | 1965-10-21 | |
| AT1028165A AT255424B (de) | 1964-12-14 | 1965-11-15 | Verfahren zur Herstellung von neuen 2-(5-Nitro-2-furyl)-chinazolinen |
| NO160494A NO118066B (de) | 1964-12-14 | 1965-11-16 | |
| BE672504A BE672504A (de) | 1964-12-14 | 1965-11-18 | |
| FR41817A FR4910M (de) | 1964-12-14 | 1965-12-10 | |
| FR41816A FR1460221A (fr) | 1964-12-14 | 1965-12-10 | Nouvelles quinazolines substituées par un radical nitrofurannique |
| CH1713065A CH448110A (de) | 1964-12-14 | 1965-12-13 | Verfahren zur Herstellung von neuen 2-(5-Nitro-2-furyl)-chinazolinen |
| GB4532167A GB1101180A (en) | 1964-12-14 | 1965-12-13 | Improvements in or relating to nitrofuryl quinazolines |
| GB52914/65A GB1101179A (en) | 1964-12-14 | 1965-12-13 | Improvements in or relating to nitrofuryl quinazolines |
| BR175667/65A BR6575667D0 (pt) | 1964-12-14 | 1965-12-14 | Processo de preparacao de 2-(5-nitro-2-turil)-quinazolinas substituidas na posicao 4 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US418311A US3324122A (en) | 1964-12-14 | 1964-12-14 | Series of 4-substituted-2-(5-nitro-2-furyl) quinazolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3324122A true US3324122A (en) | 1967-06-06 |
Family
ID=23657580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US418311A Expired - Lifetime US3324122A (en) | 1964-12-14 | 1964-12-14 | Series of 4-substituted-2-(5-nitro-2-furyl) quinazolines |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3324122A (de) |
| AT (1) | AT255424B (de) |
| BE (1) | BE672504A (de) |
| BR (1) | BR6575667D0 (de) |
| CH (1) | CH448110A (de) |
| DE (1) | DE1620076A1 (de) |
| DK (1) | DK117902B (de) |
| ES (1) | ES318292A1 (de) |
| FR (2) | FR4910M (de) |
| GB (1) | GB1101179A (de) |
| IL (1) | IL24359A (de) |
| NL (1) | NL6513634A (de) |
| NO (1) | NO118066B (de) |
| SE (1) | SE325579B (de) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542784A (en) * | 1968-04-05 | 1970-11-24 | Norwich Pharma Co | 4-(hydroxyanilino)-2-(5-nitro-2-furyl)quinazolines |
| US4055642A (en) * | 1975-05-12 | 1977-10-25 | Sandoz Ltd. | Imidazolyl-2-quinazoline derivatives |
| US5436233A (en) * | 1992-07-15 | 1995-07-25 | Ono Pharmaceutical Co., Ltd. | 4-aminoquinazoline derivatives |
| WO2005014585A1 (en) * | 2003-08-08 | 2005-02-17 | Ulysses Pharmaceutical Products Inc. | Halogenated quinazolinyl nitrofurans as antibacterial agents |
| US20080146562A1 (en) * | 2003-08-08 | 2008-06-19 | Ulysses Pharmaceutical Products Inc., | Halogenated quinazolinyl nitrofurans as antibacterial agents |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184462A (en) * | 1960-06-09 | 1965-05-18 | Mead Johnson & Co | Certain 4-substituted quinazolines |
-
1964
- 1964-12-14 US US418311A patent/US3324122A/en not_active Expired - Lifetime
-
1965
- 1965-09-23 IL IL24359A patent/IL24359A/xx unknown
- 1965-10-08 ES ES0318292A patent/ES318292A1/es not_active Expired
- 1965-10-13 DE DE19651620076 patent/DE1620076A1/de active Pending
- 1965-10-15 SE SE13375/65A patent/SE325579B/xx unknown
- 1965-10-20 DK DK535765AA patent/DK117902B/da unknown
- 1965-10-21 NL NL6513634A patent/NL6513634A/xx unknown
- 1965-11-15 AT AT1028165A patent/AT255424B/de active
- 1965-11-16 NO NO160494A patent/NO118066B/no unknown
- 1965-11-18 BE BE672504A patent/BE672504A/xx unknown
- 1965-12-10 FR FR41817A patent/FR4910M/fr not_active Expired
- 1965-12-10 FR FR41816A patent/FR1460221A/fr not_active Expired
- 1965-12-13 GB GB52914/65A patent/GB1101179A/en not_active Expired
- 1965-12-13 CH CH1713065A patent/CH448110A/de unknown
- 1965-12-14 BR BR175667/65A patent/BR6575667D0/pt unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184462A (en) * | 1960-06-09 | 1965-05-18 | Mead Johnson & Co | Certain 4-substituted quinazolines |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542784A (en) * | 1968-04-05 | 1970-11-24 | Norwich Pharma Co | 4-(hydroxyanilino)-2-(5-nitro-2-furyl)quinazolines |
| US4055642A (en) * | 1975-05-12 | 1977-10-25 | Sandoz Ltd. | Imidazolyl-2-quinazoline derivatives |
| US5436233A (en) * | 1992-07-15 | 1995-07-25 | Ono Pharmaceutical Co., Ltd. | 4-aminoquinazoline derivatives |
| WO2005014585A1 (en) * | 2003-08-08 | 2005-02-17 | Ulysses Pharmaceutical Products Inc. | Halogenated quinazolinyl nitrofurans as antibacterial agents |
| US20060258693A1 (en) * | 2003-08-08 | 2006-11-16 | Suzanne Chamberland | Halogenated quinazolinyl nitrofurans as antibacterial agents |
| US20080146562A1 (en) * | 2003-08-08 | 2008-06-19 | Ulysses Pharmaceutical Products Inc., | Halogenated quinazolinyl nitrofurans as antibacterial agents |
| US7410974B2 (en) | 2003-08-08 | 2008-08-12 | Ulysses Pharmaceutical Products, Inc. | Halogenated Quinazolinyl nitrofurans as antibacterial agents |
Also Published As
| Publication number | Publication date |
|---|---|
| FR4910M (de) | 1967-03-13 |
| ES318292A1 (es) | 1967-03-01 |
| FR1460221A (fr) | 1966-06-17 |
| NL6513634A (de) | 1966-06-15 |
| BR6575667D0 (pt) | 1973-09-06 |
| AT255424B (de) | 1967-07-10 |
| NO118066B (de) | 1969-11-03 |
| DE1620076A1 (de) | 1970-02-12 |
| SE325579B (de) | 1970-07-06 |
| DK117902B (da) | 1970-06-15 |
| IL24359A (en) | 1969-01-29 |
| GB1101179A (en) | 1968-01-31 |
| BE672504A (de) | 1966-03-16 |
| CH448110A (de) | 1967-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: NORWICH EATON PHARMACEUTICALS, INC., 17 EATON AVE. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:MORTON-NORWICH PRODUCTS, INC., A CORP. OF DE;REEL/FRAME:004085/0126 Effective date: 19820609 |