DE2448869A1 - 4-oxo-2-imidazolidinylidenharnstoffe, verfahren zu ihrer herstellung und arzneimittel - Google Patents
4-oxo-2-imidazolidinylidenharnstoffe, verfahren zu ihrer herstellung und arzneimittelInfo
- Publication number
- DE2448869A1 DE2448869A1 DE19742448869 DE2448869A DE2448869A1 DE 2448869 A1 DE2448869 A1 DE 2448869A1 DE 19742448869 DE19742448869 DE 19742448869 DE 2448869 A DE2448869 A DE 2448869A DE 2448869 A1 DE2448869 A1 DE 2448869A1
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- methyl
- urea
- imidazolidinylidene
- lower alkyl
- 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.)
- Withdrawn
Links
- -1 4-OXO-2-IMIDAZOLIDINYLIDEN Chemical class 0.000 title claims description 60
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 54
- 235000013877 carbamide Nutrition 0.000 claims description 30
- 239000004202 carbamide Substances 0.000 claims description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000012948 isocyanate Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- WTHDKMILWLGDKL-UHFFFAOYSA-N urea;hydrate Chemical compound O.NC(N)=O WTHDKMILWLGDKL-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 241000700159 Rattus Species 0.000 description 19
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- QTPPSTCTONVWRD-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=C(C)C=CC=C1C QTPPSTCTONVWRD-UHFFFAOYSA-N 0.000 description 2
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- 239000005909 Kieselgur Substances 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- NSEZUSFKACELMB-UHFFFAOYSA-N (2,6-dimethylphenyl) cyanate Chemical compound CC1=CC=CC(C)=C1OC#N NSEZUSFKACELMB-UHFFFAOYSA-N 0.000 description 1
- HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 description 1
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- GUCKTQWFKFEVTN-UHFFFAOYSA-N 1-(3-bromophenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=CC(Br)=C1 GUCKTQWFKFEVTN-UHFFFAOYSA-N 0.000 description 1
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- RUEJBUCHAUGKRS-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(3-octyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound CCCCCCCCN1CC(=O)NC1=NC(=O)NC1=CC=CC(Cl)=C1 RUEJBUCHAUGKRS-UHFFFAOYSA-N 0.000 description 1
- UVMJRAGOQOABOE-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(5-oxo-1,4-dihydroimidazol-2-yl)urea Chemical compound ClC1=CC=CC(NC(=O)N=C2NC(=O)CN2)=C1 UVMJRAGOQOABOE-UHFFFAOYSA-N 0.000 description 1
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- DORNEORKHCTYLV-UHFFFAOYSA-N 1-(3-methyl-5-oxo-4h-imidazol-2-yl)-3-(3-nitrophenyl)urea Chemical compound CN1CC(=O)NC1=NC(=O)NC1=CC=CC([N+]([O-])=O)=C1 DORNEORKHCTYLV-UHFFFAOYSA-N 0.000 description 1
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- HBCKYXDOCVRYBP-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-(3-methyl-5-oxo-4h-imidazol-2-yl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)N=C1N(C)CC(=O)N1 HBCKYXDOCVRYBP-UHFFFAOYSA-N 0.000 description 1
- SIQXOHSXPPLXBG-UHFFFAOYSA-N 1-chloro-3-isocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(Cl)C(C)=C1N=C=O SIQXOHSXPPLXBG-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- GFFGYTMCNVMFAJ-UHFFFAOYSA-N 1-isocyanato-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(N=C=O)=C1 GFFGYTMCNVMFAJ-UHFFFAOYSA-N 0.000 description 1
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- AYCDBMRVKSXYKW-UHFFFAOYSA-N 3,4-dimethylphenyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1C AYCDBMRVKSXYKW-UHFFFAOYSA-N 0.000 description 1
- UXBLDQMSOWQULB-UHFFFAOYSA-N 3-amino-2-methyl-6,7,8,9-tetrahydro-5h-cyclohepta[2,3]thieno[2,4-d]pyrimidin-4-one Chemical compound C1CCCCC2=C1SC1=C2C(=O)N(N)C(C)=N1 UXBLDQMSOWQULB-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 230000000994 depressogenic effect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- QSACPWSIIRFHHR-UHFFFAOYSA-N dimethylphenyl isocyanide Natural products CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40802273A | 1973-10-19 | 1973-10-19 | |
| US50879574A | 1974-09-23 | 1974-09-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2448869A1 true DE2448869A1 (de) | 1975-09-04 |
Family
ID=27020109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742448869 Withdrawn DE2448869A1 (de) | 1973-10-19 | 1974-10-14 | 4-oxo-2-imidazolidinylidenharnstoffe, verfahren zu ihrer herstellung und arzneimittel |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5077367A (enExample) |
| AR (1) | AR210320A1 (enExample) |
| AT (1) | AT348536B (enExample) |
| BE (1) | BE821099A (enExample) |
| CA (1) | CA1043339A (enExample) |
| CH (1) | CH614198A5 (enExample) |
| DD (1) | DD114079A5 (enExample) |
| DE (1) | DE2448869A1 (enExample) |
| DK (1) | DK548874A (enExample) |
| ES (1) | ES431153A1 (enExample) |
| FI (1) | FI59993C (enExample) |
| FR (1) | FR2248042B1 (enExample) |
| GB (1) | GB1479909A (enExample) |
| HU (1) | HU170857B (enExample) |
| IE (1) | IE40067B1 (enExample) |
| IL (1) | IL45865A (enExample) |
| IN (1) | IN139447B (enExample) |
| NL (1) | NL7413718A (enExample) |
| NO (1) | NO141162C (enExample) |
| RO (1) | RO64926A (enExample) |
| SE (1) | SE414173B (enExample) |
| YU (1) | YU36932B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016371A1 (de) * | 1979-03-14 | 1980-10-01 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Neue Harnstoffderivate, Verfahren und Zwischenprodukte zu deren Herstellung und Arzneimittel enthaltend ein solches Harnstoffderivat sowie die Verwendung eines solchen Harnstoffderivates bei der Bekämpfung von Krankheiten |
| EP0029663A1 (en) * | 1979-10-29 | 1981-06-03 | McNeilab, Inc. | N-aryl-N'-imidazol-2-ylureas, process for their preparation and pharmaceutical compositions containing them |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2548388A1 (en) * | 2003-12-15 | 2005-06-30 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| EP3653609B1 (en) | 2013-02-12 | 2024-04-03 | Buck Institute for Research on Aging | Hydantoins that modulate bace-mediated app processing |
-
1974
- 1974-10-14 DE DE19742448869 patent/DE2448869A1/de not_active Withdrawn
- 1974-10-15 SE SE7412959A patent/SE414173B/xx unknown
- 1974-10-15 BE BE149558A patent/BE821099A/xx unknown
- 1974-10-16 AR AR256117A patent/AR210320A1/es active
- 1974-10-17 IL IL45865A patent/IL45865A/xx unknown
- 1974-10-17 CH CH1395174A patent/CH614198A5/xx not_active IP Right Cessation
- 1974-10-17 RO RO197480253A patent/RO64926A/ro unknown
- 1974-10-18 YU YU2797/74A patent/YU36932B/xx unknown
- 1974-10-18 HU HU74ME00001786A patent/HU170857B/hu unknown
- 1974-10-18 CA CA211,775A patent/CA1043339A/en not_active Expired
- 1974-10-18 ES ES431153A patent/ES431153A1/es not_active Expired
- 1974-10-18 NO NO743771A patent/NO141162C/no unknown
- 1974-10-18 NL NL7413718A patent/NL7413718A/xx not_active Application Discontinuation
- 1974-10-18 JP JP49119494A patent/JPS5077367A/ja active Pending
- 1974-10-18 FR FR7435155A patent/FR2248042B1/fr not_active Expired
- 1974-10-18 FI FI3065/74A patent/FI59993C/fi active
- 1974-10-18 IE IE2146/74A patent/IE40067B1/xx unknown
- 1974-10-18 DK DK548874A patent/DK548874A/da not_active Application Discontinuation
- 1974-10-18 GB GB45246/74A patent/GB1479909A/en not_active Expired
- 1974-10-18 AT AT840974A patent/AT348536B/de not_active IP Right Cessation
- 1974-10-21 DD DD181808A patent/DD114079A5/xx unknown
- 1974-11-07 IN IN2451/CAL/74A patent/IN139447B/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016371A1 (de) * | 1979-03-14 | 1980-10-01 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Neue Harnstoffderivate, Verfahren und Zwischenprodukte zu deren Herstellung und Arzneimittel enthaltend ein solches Harnstoffderivat sowie die Verwendung eines solchen Harnstoffderivates bei der Bekämpfung von Krankheiten |
| EP0029663A1 (en) * | 1979-10-29 | 1981-06-03 | McNeilab, Inc. | N-aryl-N'-imidazol-2-ylureas, process for their preparation and pharmaceutical compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| DD114079A5 (enExample) | 1975-07-12 |
| YU279774A (en) | 1982-06-18 |
| RO64926A (fr) | 1980-01-15 |
| SE7412959L (enExample) | 1975-04-21 |
| NO743771L (enExample) | 1975-05-20 |
| DK548874A (enExample) | 1975-07-07 |
| HU170857B (hu) | 1977-09-28 |
| AT348536B (de) | 1979-02-26 |
| FR2248042B1 (enExample) | 1978-07-21 |
| JPS5077367A (enExample) | 1975-06-24 |
| FI306574A7 (enExample) | 1975-04-20 |
| NO141162B (no) | 1979-10-15 |
| IL45865A0 (en) | 1975-02-10 |
| FI59993C (fi) | 1981-11-10 |
| YU36932B (en) | 1984-08-31 |
| GB1479909A (en) | 1977-07-13 |
| NL7413718A (nl) | 1975-04-22 |
| IL45865A (en) | 1978-01-31 |
| FI59993B (fi) | 1981-07-31 |
| IE40067B1 (en) | 1979-02-28 |
| IN139447B (enExample) | 1976-06-19 |
| CA1043339A (en) | 1978-11-28 |
| ATA840974A (de) | 1978-07-15 |
| ES431153A1 (es) | 1977-02-01 |
| SE414173B (sv) | 1980-07-14 |
| IE40067L (en) | 1975-04-19 |
| FR2248042A1 (enExample) | 1975-05-16 |
| NO141162C (no) | 1980-01-23 |
| CH614198A5 (en) | 1979-11-15 |
| AU7443874A (en) | 1976-04-29 |
| BE821099A (fr) | 1975-04-15 |
| AR210320A1 (es) | 1977-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |