DE1643965A1 - Neue Karbamid-Derivate und Verfahren zu ihrer Herstellung - Google Patents
Neue Karbamid-Derivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1643965A1 DE1643965A1 DE19681643965 DE1643965A DE1643965A1 DE 1643965 A1 DE1643965 A1 DE 1643965A1 DE 19681643965 DE19681643965 DE 19681643965 DE 1643965 A DE1643965 A DE 1643965A DE 1643965 A1 DE1643965 A1 DE 1643965A1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- general formula
- phenyl
- group
- unsubstituted
- 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 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000003672 ureas Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 3
- 230000002365 anti-tubercular Effects 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 150000003585 thioureas Chemical class 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- UCDWFUGHXVFQMT-UHFFFAOYSA-N 4-(3-methylbutoxy)-n-phenylaniline Chemical compound C1=CC(OCCC(C)C)=CC=C1NC1=CC=CC=C1 UCDWFUGHXVFQMT-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000002540 isothiocyanates Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 238000009736 wetting Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- -1 4-ethoxyphenyl Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 2
- 229960004909 aminosalicylic acid Drugs 0.000 description 2
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- HXDMRUHZGHWXOI-UHFFFAOYSA-N propyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCCOC(=O)N=C=S HXDMRUHZGHWXOI-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LXWFHMREWLOKLM-UHFFFAOYSA-N CP-24879 Chemical compound CC(C)CCOC1=CC=C(N)C=C1 LXWFHMREWLOKLM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- 244000026610 Cynodon dactylon var. affinis Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 244000309464 bull Species 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
- 241001233037 catfish Species 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000003245 coal 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
- QGIRBAOVIAHGDV-UHFFFAOYSA-N ethyl thiocyanatoformate Chemical compound CCOC(=O)SC#N QGIRBAOVIAHGDV-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001549 tubercolostatic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
- C07C335/28—Y being a hetero atom, e.g. thiobiuret
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001004 | 1967-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1643965A1 true DE1643965A1 (de) | 1971-07-15 |
Family
ID=10996662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681643965 Pending DE1643965A1 (de) | 1967-01-24 | 1968-01-23 | Neue Karbamid-Derivate und Verfahren zu ihrer Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT278855B (enrdf_load_stackoverflow) |
| CH (1) | CH495341A (enrdf_load_stackoverflow) |
| DE (1) | DE1643965A1 (enrdf_load_stackoverflow) |
| DK (1) | DK115766B (enrdf_load_stackoverflow) |
| FR (1) | FR7827M (enrdf_load_stackoverflow) |
| GB (1) | GB1211041A (enrdf_load_stackoverflow) |
| NL (1) | NL6800901A (enrdf_load_stackoverflow) |
| SE (1) | SE331275B (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA6904362B (enrdf_load_stackoverflow) * | 1968-06-18 | |||
| FR2196794A1 (en) * | 1972-08-24 | 1974-03-22 | Dainippon Pharmaceutical Co | 1-(pyridyl)-3-substd-thiourea derivs - hypoxia inhibitors |
| US4072696A (en) * | 1973-02-12 | 1978-02-07 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US4556483A (en) * | 1984-08-17 | 1985-12-03 | American Cyanamid Company | Neutral hydrocarboxycarbonyl thiourea sulfide collectors |
| GB2163068B (en) * | 1984-08-17 | 1988-09-28 | American Cyanamid Co | Neutral circuit sulfide collectors |
| USRE32786E (en) * | 1984-08-17 | 1988-11-22 | American Cyanamid Company | Neutral hydrocarboxycarbonyl thiourea sulfide collectors |
| US4556482A (en) * | 1984-08-17 | 1985-12-03 | American Cyanamid Company | Process for the flotation of base metal sulfide minerals in acid, neutral or mildly alkaline circuits |
-
1968
- 1968-01-12 GB GB197168A patent/GB1211041A/en not_active Expired
- 1968-01-19 DK DK21968A patent/DK115766B/da unknown
- 1968-01-19 NL NL6800901A patent/NL6800901A/xx unknown
- 1968-01-23 SE SE89068A patent/SE331275B/xx unknown
- 1968-01-23 FR FR136949A patent/FR7827M/fr not_active Expired
- 1968-01-23 DE DE19681643965 patent/DE1643965A1/de active Pending
- 1968-01-24 CH CH108068A patent/CH495341A/de not_active IP Right Cessation
- 1968-01-24 AT AT69368A patent/AT278855B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1211041A (en) | 1970-11-04 |
| CH495341A (de) | 1970-08-31 |
| FR7827M (enrdf_load_stackoverflow) | 1970-05-25 |
| AT278855B (de) | 1970-02-10 |
| SE331275B (enrdf_load_stackoverflow) | 1970-12-21 |
| NL6800901A (enrdf_load_stackoverflow) | 1968-07-25 |
| DK115766B (da) | 1969-11-10 |
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