NO122426B - - Google Patents
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- Publication number
- NO122426B NO122426B NO169139A NO16913967A NO122426B NO 122426 B NO122426 B NO 122426B NO 169139 A NO169139 A NO 169139A NO 16913967 A NO16913967 A NO 16913967A NO 122426 B NO122426 B NO 122426B
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- furyl
- nitro
- oxadiazol
- salts
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 19
- -1 alkali metal salt Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 150000003839 salts Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 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
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 241000224526 Trichomonas Species 0.000 description 3
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 208000005448 Trichomonas Infections Diseases 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 206010044620 Trichomoniasis Diseases 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 241001058196 Tritrichomonas foetus Species 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZLMJMSJWJFRBEC-BJUDXGSMSA-N potassium-38 Chemical compound [38K] ZLMJMSJWJFRBEC-BJUDXGSMSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0038484 | 1966-03-14 | ||
| DE19661670338 DE1670338A1 (de) | 1966-03-14 | 1966-03-14 | Verfahren zur Herstellung von antimikrobiell wirksamen Nitrofuranderivaten |
| DEC0039685 | 1966-07-22 | ||
| DES0039686 | 1966-07-22 | ||
| DEC0039684 | 1966-07-22 | ||
| DE19661670370 DE1670370A1 (de) | 1966-03-14 | 1966-07-22 | Verfahren zur herstellung von antimikrobiell wirksamen nitrofuranderivaten |
| DEC0039686 | 1966-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122426B true NO122426B (fr) | 1971-06-28 |
Family
ID=27561261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO169139A NO122426B (fr) | 1966-03-14 | 1967-07-21 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US3557099A (fr) |
| CH (5) | CH509341A (fr) |
| DE (4) | DE1670338A1 (fr) |
| ES (2) | ES337963A1 (fr) |
| FR (4) | FR6185M (fr) |
| GB (2) | GB1184044A (fr) |
| MY (1) | MY7300103A (fr) |
| NL (2) | NL6706448A (fr) |
| NO (1) | NO122426B (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4007185A (en) * | 1967-01-31 | 1977-02-08 | Abbott Laboratories | 3,5-Substituted-1,2,4-oxadiazole inner quaternary ammonium salts |
| GB1228142A (fr) * | 1967-03-31 | 1971-04-15 | ||
| DE2860691D1 (en) * | 1977-07-12 | 1981-08-13 | Synthelabo | 1,2,4-oxadiazol derivatives, their preparation and application in pharmaceutical compositions |
| US5420146A (en) * | 1994-05-10 | 1995-05-30 | American Home Products Corporation | Di-oxadiazolidine derivatives as antihyperglycemic agents |
| US7652018B2 (en) * | 2006-08-15 | 2010-01-26 | Wyeth Llc | Imidazolidin-2-one derivatives useful as PR modulators |
| US7538107B2 (en) | 2006-08-15 | 2009-05-26 | Wyeth | Oxazinan-2-one derivatives useful as PR modulators |
| US7649007B2 (en) * | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| TW200815428A (en) * | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3146232A (en) * | 1962-09-17 | 1964-08-25 | Saikachi Haruo | 5-(5-nitro-2-furyl-mono- and di-vinylene)-1, 3, 4-oxadiazoline-2-one and process |
| US3336304A (en) * | 1964-01-28 | 1967-08-15 | Fujisawa Pharmaceutical Co | 1, 3, 4-oxadiazolin-5-one derivatives and process for the preparation thereof |
-
1966
- 1966-03-14 DE DE19661670338 patent/DE1670338A1/de not_active Withdrawn
- 1966-07-22 DE DE19661670371 patent/DE1670371A1/de active Pending
- 1966-07-22 DE DE19661670370 patent/DE1670370A1/de active Pending
- 1966-07-22 DE DE19661670372 patent/DE1670372A1/de active Pending
-
1967
- 1967-01-24 US US611266A patent/US3557099A/en not_active Expired - Lifetime
- 1967-01-24 US US611239A patent/US3474462A/en not_active Expired - Lifetime
- 1967-03-13 GB GB01689/67A patent/GB1184044A/en not_active Expired
- 1967-03-13 ES ES337963A patent/ES337963A1/es not_active Expired
- 1967-03-14 CH CH368767A patent/CH509341A/de not_active IP Right Cessation
- 1967-03-14 FR FR98602A patent/FR6185M/fr not_active Expired
- 1967-03-14 CH CH1452169D patent/CH507284A/de not_active IP Right Cessation
- 1967-03-14 FR FR98604A patent/FR1514028A/fr not_active Expired
- 1967-05-02 GB GB20281/67A patent/GB1189315A/en not_active Expired
- 1967-05-09 NL NL6706448A patent/NL6706448A/xx unknown
- 1967-05-31 CH CH654269A patent/CH486486A/fr not_active IP Right Cessation
- 1967-05-31 CH CH654369A patent/CH475273A/fr not_active IP Right Cessation
- 1967-05-31 CH CH766267A patent/CH476012A/fr not_active IP Right Cessation
- 1967-06-21 FR FR1601067D patent/FR1601067A/fr not_active Expired
- 1967-06-22 FR FR111460A patent/FR6558M/fr not_active Expired
- 1967-06-23 NL NL6708759A patent/NL6708759A/xx unknown
- 1967-07-21 ES ES343314A patent/ES343314A1/es not_active Expired
- 1967-07-21 NO NO169139A patent/NO122426B/no unknown
-
1973
- 1973-12-31 MY MY1973103A patent/MY7300103A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES343314A1 (es) | 1968-12-01 |
| GB1189315A (en) | 1970-04-22 |
| FR6185M (fr) | 1968-07-15 |
| US3557099A (en) | 1971-01-19 |
| MY7300103A (en) | 1973-12-31 |
| DE1670338A1 (de) | 1972-08-10 |
| US3474462A (en) | 1969-10-21 |
| FR1514028A (fr) | 1968-02-16 |
| CH486486A (fr) | 1970-02-28 |
| NL6708759A (fr) | 1968-01-23 |
| CH476012A (fr) | 1969-07-31 |
| DE1670371A1 (de) | 1971-01-28 |
| DE1670372A1 (de) | 1971-01-14 |
| GB1184044A (en) | 1970-03-11 |
| NL6706448A (fr) | 1968-01-23 |
| DE1670370A1 (de) | 1973-03-29 |
| CH509341A (de) | 1971-06-30 |
| FR6558M (fr) | 1968-12-23 |
| FR1601067A (fr) | 1970-08-10 |
| CH475273A (fr) | 1969-07-15 |
| CH507284A (de) | 1971-05-15 |
| ES337963A1 (es) | 1968-03-16 |
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