NO118066B - - Google Patents
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- Publication number
- NO118066B NO118066B NO160494A NO16049465A NO118066B NO 118066 B NO118066 B NO 118066B NO 160494 A NO160494 A NO 160494A NO 16049465 A NO16049465 A NO 16049465A NO 118066 B NO118066 B NO 118066B
- Authority
- NO
- Norway
- Prior art keywords
- time
- devices
- mol
- register
- establishment
- Prior art date
Links
- 230000000694 effects Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 claims 4
- 230000000903 blocking effect Effects 0.000 claims 1
- 238000012544 monitoring process Methods 0.000 claims 1
- 230000011664 signaling Effects 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- 238000001914 filtration Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- -1 4-substituted 2-(5-nitro-2-furyl)-quinazolines Chemical class 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
- ZLLKFYHIFIHVJA-UHFFFAOYSA-N 4-chloro-2-(5-nitrofuran-2-yl)quinazoline Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC(Cl)=C(C=CC=C2)C2=N1 ZLLKFYHIFIHVJA-UHFFFAOYSA-N 0.000 description 2
- 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
- 241001465754 Metazoa Species 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 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
- 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
- 238000002360 preparation method Methods 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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- OLEFNFXYGGTROA-UHFFFAOYSA-N 5-nitrofuran-2-carbonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)O1 OLEFNFXYGGTROA-UHFFFAOYSA-N 0.000 description 1
- HCOZNPZJMDOFFS-UHFFFAOYSA-N 6-chloro-2-(5-nitrofuran-2-yl)quinoline-4-carboxylic acid Chemical compound ClC=1C=C2C(=CC(=NC2=CC1)C=1OC(=CC1)[N+](=O)[O-])C(=O)O HCOZNPZJMDOFFS-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 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
- 229940126062 Compound A Drugs 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 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
- 239000007799 cork Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [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
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing 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
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture 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
- 239000000725 suspension Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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 |
|---|---|
| NO118066B true NO118066B (pt) | 1969-11-03 |
Family
ID=23657580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160494A NO118066B (pt) | 1964-12-14 | 1965-11-16 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3324122A (pt) |
| AT (1) | AT255424B (pt) |
| BE (1) | BE672504A (pt) |
| BR (1) | BR6575667D0 (pt) |
| CH (1) | CH448110A (pt) |
| DE (1) | DE1620076A1 (pt) |
| DK (1) | DK117902B (pt) |
| ES (1) | ES318292A1 (pt) |
| FR (2) | FR4910M (pt) |
| GB (1) | GB1101179A (pt) |
| IL (1) | IL24359A (pt) |
| NL (1) | NL6513634A (pt) |
| NO (1) | NO118066B (pt) |
| SE (1) | SE325579B (pt) |
Families Citing this family (6)
| 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 |
| 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 |
| CH612432A5 (pt) * | 1975-05-12 | 1979-07-31 | Sandoz Ag | |
| 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 |
| US20080146562A1 (en) * | 2003-08-08 | 2008-06-19 | Ulysses Pharmaceutical Products Inc., | Halogenated quinazolinyl nitrofurans as antibacterial agents |
| WO2005014585A1 (en) * | 2003-08-08 | 2005-02-17 | Ulysses Pharmaceutical Products Inc. | Halogenated quinazolinyl nitrofurans as antibacterial agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL265777A (pt) * | 1960-06-09 |
-
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 CH CH1713065A patent/CH448110A/de unknown
- 1965-12-13 GB GB52914/65A patent/GB1101179A/en not_active Expired
- 1965-12-14 BR BR175667/65A patent/BR6575667D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE325579B (pt) | 1970-07-06 |
| FR4910M (pt) | 1967-03-13 |
| CH448110A (de) | 1967-12-15 |
| US3324122A (en) | 1967-06-06 |
| DE1620076A1 (de) | 1970-02-12 |
| FR1460221A (fr) | 1966-06-17 |
| GB1101179A (en) | 1968-01-31 |
| DK117902B (da) | 1970-06-15 |
| BE672504A (pt) | 1966-03-16 |
| BR6575667D0 (pt) | 1973-09-06 |
| AT255424B (de) | 1967-07-10 |
| NL6513634A (pt) | 1966-06-15 |
| ES318292A1 (es) | 1967-03-01 |
| IL24359A (en) | 1969-01-29 |
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