DE2123639A1 - S-Nitro-S-methylcarbamoyloxychinolin und Verfahren zu dessen Herstellung - Google Patents
S-Nitro-S-methylcarbamoyloxychinolin und Verfahren zu dessen HerstellungInfo
- Publication number
- DE2123639A1 DE2123639A1 DE19712123639 DE2123639A DE2123639A1 DE 2123639 A1 DE2123639 A1 DE 2123639A1 DE 19712123639 DE19712123639 DE 19712123639 DE 2123639 A DE2123639 A DE 2123639A DE 2123639 A1 DE2123639 A1 DE 2123639A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- methylcarbamoyloxyquinoline
- inorganic
- salts
- preparation
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 235000005985 organic acids Nutrition 0.000 claims description 5
- GKPRSAKLBYSVKI-UHFFFAOYSA-N (5-nitroquinolin-8-yl) N-methylcarbamate Chemical compound [N+](=O)([O-])C1=C2C=CC=NC2=C(C=C1)OC(NC)=O GKPRSAKLBYSVKI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 3
- RJIWZDNTCBHXAL-UHFFFAOYSA-N nitroxoline Chemical compound C1=CN=C2C(O)=CC=C([N+]([O-])=O)C2=C1 RJIWZDNTCBHXAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 241000123650 Botrytis cinerea Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000221779 Fusarium sambucinum Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000208822 Lactuca Species 0.000 description 2
- 235000003228 Lactuca sativa Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- -1 ethylcarbamoyloxychinolin Chemical compound 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
- MYODENLXTDMHTA-UHFFFAOYSA-N 7a-(trichloromethylsulfanyl)-4,5-dihydro-3ah-isoindole-1,3-dione Chemical compound C1=CCCC2C(=O)NC(=O)C21SC(Cl)(Cl)Cl MYODENLXTDMHTA-UHFFFAOYSA-N 0.000 description 1
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010026389 Gramicidin Proteins 0.000 description 1
- 206010021531 Impetigo Diseases 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 206010023375 Kerion Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 208000010195 Onychomycosis Diseases 0.000 description 1
- 208000006311 Pyoderma Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 229960004905 gramicidin Drugs 0.000 description 1
- ZWCXYZRRTRDGQE-SORVKSEFSA-N gramicidina Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CC=3C4=CC=CC=C4NC=3)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC=O)C(C)C)CC(C)C)C(=O)NCCO)=CNC2=C1 ZWCXYZRRTRDGQE-SORVKSEFSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 208000005005 intertrigo Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- NEOCJLWBSDEGCI-UHFFFAOYSA-N quinolin-2-yl carbamate Chemical compound C1=CC=CC2=NC(OC(=O)N)=CC=C21 NEOCJLWBSDEGCI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
- C07D215/34—Carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR707017393A FR2088061B1 (enrdf_load_stackoverflow) | 1970-05-13 | 1970-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2123639A1 true DE2123639A1 (de) | 1971-11-25 |
Family
ID=9055444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712123639 Pending DE2123639A1 (de) | 1970-05-13 | 1971-05-12 | S-Nitro-S-methylcarbamoyloxychinolin und Verfahren zu dessen Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU2877371A (enrdf_load_stackoverflow) |
| BE (1) | BE767002A (enrdf_load_stackoverflow) |
| DE (1) | DE2123639A1 (enrdf_load_stackoverflow) |
| ES (1) | ES391071A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2088061B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1309723A (enrdf_load_stackoverflow) |
| IL (1) | IL36802A0 (enrdf_load_stackoverflow) |
| NL (1) | NL7106417A (enrdf_load_stackoverflow) |
| ZA (1) | ZA713117B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3347014A1 (de) * | 1983-12-24 | 1985-07-04 | Vdo Schindling | Zeigereinrichtung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH438307A (de) * | 1964-06-04 | 1967-06-30 | Agripat Sa | Verfahren zur Herstellung neuer heterocyclischer Carbaminsäureester und ihre Verwendung zur Bekämpfung phytopathogener Pilze |
-
1970
- 1970-05-13 FR FR707017393A patent/FR2088061B1/fr not_active Expired
-
1971
- 1971-05-10 IL IL36802A patent/IL36802A0/xx unknown
- 1971-05-11 NL NL7106417A patent/NL7106417A/xx unknown
- 1971-05-11 BE BE767002A patent/BE767002A/xx unknown
- 1971-05-12 DE DE19712123639 patent/DE2123639A1/de active Pending
- 1971-05-12 ES ES391071A patent/ES391071A1/es not_active Expired
- 1971-05-12 AU AU28773/71A patent/AU2877371A/en not_active Expired
- 1971-05-13 ZA ZA713117A patent/ZA713117B/xx unknown
- 1971-05-13 GB GB1475871*[A patent/GB1309723A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3347014A1 (de) * | 1983-12-24 | 1985-07-04 | Vdo Schindling | Zeigereinrichtung |
Also Published As
| Publication number | Publication date |
|---|---|
| IL36802A0 (en) | 1971-07-28 |
| GB1309723A (en) | 1973-03-14 |
| FR2088061A1 (enrdf_load_stackoverflow) | 1972-01-07 |
| FR2088061B1 (enrdf_load_stackoverflow) | 1973-04-06 |
| ES391071A1 (es) | 1973-07-16 |
| AU2877371A (en) | 1972-11-16 |
| NL7106417A (enrdf_load_stackoverflow) | 1971-11-16 |
| BE767002A (fr) | 1971-11-12 |
| ZA713117B (en) | 1972-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |