PL143836B1 - Method of obtaining novel substituted ureas - Google Patents
Method of obtaining novel substituted ureas Download PDFInfo
- Publication number
- PL143836B1 PL143836B1 PL1983240284A PL24028483A PL143836B1 PL 143836 B1 PL143836 B1 PL 143836B1 PL 1983240284 A PL1983240284 A PL 1983240284A PL 24028483 A PL24028483 A PL 24028483A PL 143836 B1 PL143836 B1 PL 143836B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- carbon atoms
- alkyl
- benzyl
- substituent
- Prior art date
Links
- 235000013877 carbamide Nutrition 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 7
- 150000003672 ureas Chemical class 0.000 title claims description 3
- -1 ortho-phenylene Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006277 halobenzyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000006178 methyl benzyl group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 17
- 239000004202 carbamide Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- SAPLBENRNUWLDZ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(3-chlorophenyl)urea Chemical compound C=1C=CC(Cl)=CC=1NC(=O)N(CCCC)CC1=CC=CC=C1 SAPLBENRNUWLDZ-UHFFFAOYSA-N 0.000 description 2
- JLKZDESEPHIECO-UHFFFAOYSA-N 2,4-dichloro-n-[(2,4-dimethylphenyl)methyl]aniline Chemical compound CC1=CC(C)=CC=C1CNC1=CC=C(Cl)C=C1Cl JLKZDESEPHIECO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- PUEUFOKKVOOXEW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]butan-1-amine Chemical compound CCCCNCC1=CC=CC=C1Cl PUEUFOKKVOOXEW-UHFFFAOYSA-N 0.000 description 2
- HIPXPABRMMYVQD-UHFFFAOYSA-N n-benzylbutan-1-amine Chemical compound CCCCNCC1=CC=CC=C1 HIPXPABRMMYVQD-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- CQCRPHVZWXLSLZ-UHFFFAOYSA-N 1-benzyl-1-butyl-3-(2,4-dimethylphenyl)urea Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)N(CCCC)CC1=CC=CC=C1 CQCRPHVZWXLSLZ-UHFFFAOYSA-N 0.000 description 1
- QUOBVYPFBJUOAJ-UHFFFAOYSA-N 1-isocyanato-2,4-dimethylbenzene Chemical compound CC1=CC=C(N=C=O)C(C)=C1 QUOBVYPFBJUOAJ-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- BWSMFVJXLIVYOM-UHFFFAOYSA-N ethyl 4-[(4-phenylmethoxyphenyl)methylideneamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N=CC(C=C1)=CC=C1OCC1=CC=CC=C1 BWSMFVJXLIVYOM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- DGWIPMVOWWLJMU-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-1-(2,4-dimethylphenyl)methanimine Chemical compound CC1=CC(C)=CC=C1C=NC1=CC=C(Cl)C=C1Cl DGWIPMVOWWLJMU-UHFFFAOYSA-N 0.000 description 1
- WWIIUZRDEYPOAR-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)methyl]-2,4-dimethylaniline Chemical compound CC1=CC(C)=CC=C1NCC1=CC=C(Cl)C=C1Cl WWIIUZRDEYPOAR-UHFFFAOYSA-N 0.000 description 1
- YSEGFBXNCKAPKQ-UHFFFAOYSA-N n-[(2,4-dimethylphenyl)methyl]-2,4-dimethylaniline Chemical compound CC1=CC(C)=CC=C1CNC1=CC=C(C)C=C1C YSEGFBXNCKAPKQ-UHFFFAOYSA-N 0.000 description 1
- SIBVVRORCRNRLU-UHFFFAOYSA-N n-benzyl-2,4-dimethylaniline Chemical compound CC1=CC(C)=CC=C1NCC1=CC=CC=C1 SIBVVRORCRNRLU-UHFFFAOYSA-N 0.000 description 1
- MMEIYVXPSXIGET-UHFFFAOYSA-N n-benzyl-4-chloroaniline Chemical compound C1=CC(Cl)=CC=C1NCC1=CC=CC=C1 MMEIYVXPSXIGET-UHFFFAOYSA-N 0.000 description 1
- PERRBGDAOVSLIV-UHFFFAOYSA-N n-butyl-2-chlorobenzamide Chemical compound CCCCNC(=O)C1=CC=CC=C1Cl PERRBGDAOVSLIV-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
- C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
- C07C273/1827—X being H
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
Description
II r——— i K x - 134-139° 111-117° N-/2-chlorobenzylideno/-2-chloroanilina N-/4-metylobenzylideno/-4-metyloanilina i X l ! XI 90-93u N-/4-benzyloksybenzylideno/-4-karboetoksyanilina N-benzylldeno-3-nitroanilina 14D-142C ! XII 69-72° i —i Przyklad XIII. Sposób wytwarzania N-/2,4-dimetylobenzylo/-2,4-dichloroaniliny.Mieszanine 13,9 g N-/2,4-dimetylobenzylideno/-2,4-dichloroaniliny, 1,89 g borowodorku sodu i 150 ml etanolu mieszano ogrzewajac pod chlodnica zwrotna przez 1 godzine, pozostawiono do ochlodzenia i wylano do wody. Pd przekrystalizowaniu z etanolu otrzymano N-/2,4-dimetylobenzy- lo/-2,4-dichloroaniline o temperaturze topnienia 88-90°.Inne analizy otrzymane sposobem opisanym w przykladzie XIII przedstawiono w tablicy 3i Tablica 3 R?zyklad Zwiazek Temperatura topnienia XIV N-/2,4-dimetylobenzylo/-2,4-dimetyloanilina 72-74c N-/2,4-dichlorobenzylo/-2,4-dimetyloanilina TC-72L XVI N-benzylo-4-chloroanilina 48-49 XVII XVIII N-benzylo-2,4-dimetyloanilina 28-33u N-/2,4-dichlorobenzylo/-2,4-dichloroanilina 84-86u XIX XX ¦+ N-/2-chlorob enzylo/-2-chloroanilina 41-44L N-/4-metylobenzylo/-4-metyloanilina N-/4-benzyloksybenzylo/-4-karboetoksyanilina N-benzylo-3-nitroanilina 50-54u XXI XXII 147-150 10 6-10 8C Przyklad XXIII. Sposób wytwarzania l-benzylo-1-/n-butylo/-3-/2,4-dimetylo- fenylo/mocznika. Roztwór 4,89 g 2,4-dimetylofenyloizocyjanianu w 100 ml heksanu dodano do roz¬ tworu 4,41 g N-benzylo-n-butyloaminy v 150 ml heksanu i roztwór mieszano w temperaturze poko¬ jowej przez 2 godziny a nastepnie odparowano. Ibzostaly osad przekrystalizowano z pentanu otrzymujac 1-benzylo-1-/n-butylo/-3-/2,4-dimetylofenylo/mocznik o temperaturze topnienia 70-71°C.Przyklad XXIV. Sposób wytwarzania 1 -benzylo-1 -/n-butylo/-3-/3-chlorofenylo/ mocznika. Roztwór 1,56 g chloromrówczanu fenylu w 50 ml eteru wkroplono do mieszanego roztworu 2,55 g 3-chloroaniliny w 35 ml eterui Mieszanine mieszano przez 1 godzine w temperaraturze pokojowej a nastepnie przesaczono. Frzesacz odparowano i pozostalosc krystalizowano z heksanu otrzymujac tt-/3-chlorofenylo/karbaminian fenylui143 836 11 Roztwór 1,46 g N-/3-chlorofenylo/-karbaminianu fenylu w 15 ml tetrahydrofuranu dodano do roztworu 1,92 g N-benzylo-n-butyloaminy w 20 ml tetrahydrofuranu i mieszanine mieszano pod chlodnica zwrotna przez 24 godziny. Mieszanine rozcienczono heksanem i wytracony osad odsaczono, R) przekrystalizowaniu z pentanu otrzymano 1-benzylo-1-/n-butylo/-3-/3-chlorofenylo/mocznik o temperaturze topnienia 69-70°C, Przykl ad XXV, Sposób wytwarzania N-/n-butylo/-2-chlorobenzyloaminy, Roztwór 21,2 g N-/n-butylo/-2-chlorobenzamidu w 100 ml tetrahydrofuranu dodano chlodzac do 200 ml 1M borowodorku w tetrahydrofuranie i mieszanine mieszano ogrzewajac pod chlodnica zwrotna przez 18 godzin, pozostawiono do ochlodzenia i potraktowano 6N kwasem solnym. Rozpuszczalnik orga¬ niczny odparowano i pozostalosc rozdzielono miedzy eter i roztwór wodny wodorotlenku sodu. War¬ stwe eterowa oddzielono, wysuszono i odparowano, Ebzostalosc destylowano otrzymujac N-/n-bu- tylo/-2-chlorobenzyloamine w postaci bezbarwnej cieczy o temperaturze wrzenia 65-75°• Moczniki przedstawione w tablicy 4 otrzymano z odpowiednich aryloizocyjanianów i amin drugorzedowych sposobem wedlug wynalazku.Tablica4 i Przyklad i Zwiazek i Temperatura i | ! | topnienia ! L_____ __J________ _______________________________________________-,-U------_------_ _---__-_| i XXVI i 1f1-dibenzylo-3-/3-metylofenylo/mocznik J 126-123° J i XXVII i 1,1-dibenzylo-3-/4-metylofenylo/mocznik ! 170-172° } j XXVIII j 1,1-dibenzylo-3-/4-n-butylofenylo/mocznik J 104-10 6° ¦ | XXIX | 1,1-dibenzylo-3-/2,4,5-trimetylofenylo/mocznik J 141-142° J i XXX ! 1,1-dibenzylo-3-/2,4,6-trimetylofenylo/mocznik { 163-165° ! ¦ 1 _ _ . »...—^_««j*.^*.——— i j XXXI [ 1,1-dibenzylo-3-/2-bromofenylo/mocznik i 118-119 ¦ i XXXII ! 1,1-dibenzylo-3-/4-jodofenylo/mocznik | 233-235° j L_-_ __-_ __ «_« —__ - _-- _-_-_-_ -._- — ____——-___-.-J-_____—------ | ! XXXIII ! 1,1-dibenzylo-3-/3,5-dichlorofenylo/mocznik i ... 144-145° | j XXXIV j 1,1-dibenzylo-3-/3-acetylofenylo/mocznik [ 124-127° j ! XXXV ! 1,1-dibenzylo/-3-/4-karboetoksyfenylo/mocznik | 91-93 ! i XXXVI i 1,1-dibenzylo-3-/4-fenoksyfenylo/mocznik ! 144-146 ! j XXXVII | 1,1-dibenzylo-3-/3-chloro-2-metoksyfenylo/mocznik j 138-139° | i XXXVIII I 1,1-dibenzylo-3-/4-chloro-3-trifluorometylofenylo/ \ \ j j mocznik " J 146-143 j i XXXIX ! 1f1-dibenzylo-3-/4-chloro-2-trifluorometylofenylo/ j ft j j | mocznik j 82-83 j i XL I 1f1-dibenzylo-3-/2,5-difluorofenylo/mocznik j 67-68 J j XLI j 1,1-dibenzylo-3-/2,4-dibromofenylo/mocznik i 107-108° i | XLII | 1-benzylo-1-/n-butylo/-3-benzylo-3-/2,4,6-trimetylo- [ j j i fenylo/mocznik i 63-69 i | XLIII j 1,1-dibenzylo-3-/3,4-dibenzofenylo/mocznik j 173-172° j ! XLIV ! 1,1-dibenzylo-3-/2-trifluorometylofenylo/mocznik | 111-114° |12 143 836 PL PL PL PL PL PL PL PL
Claims (1)
1*2 oznacza grupy alkilowa, alkoksylowa lub alkenylowa o 5-12 atomach wegla lub grupe aralkilo¬ wa o 7-14 atomach wegla,w której pierscien aromatyczny ewentualnie zawiera co najmniej jeden podstawnik obejmujacy grupe alkilowa o 1-10 atomach wegla, grupe alkoksylowa o 1-10 atomach wegla, grupe fenoksylowa, benzyloksylowa, metylenodioksylowa, grupe alkilotiolowa o 1-4 atomach wegla, grupe fenylowa, atom chlorowca, grupe trichlorowcometylowa, grupe adamantylowa, grupe karboalkoksylowa o 1-4 atomach wegla lub grupe nitrowa, a R, oznacza atom wodoru lub grupe alkilowa o 1-4 atomach wegla, alkenylowa o 1-4 atomach wegla, alkinylowa o 1-4 atomach wegla, benzylowa, benzylowa posiadajaca co najnniej Jeden podstawnik Z wybrany niezaleznie sposród okreslonych symbolem X, znamienny tym, ze aryloizocyjanian o wzorze ogólnym 2, w którym X ma wyzej podane znaczenie, poddaje sie reakcji z drugorzedowa amina o ogól¬ nym wzorze 3, w którym R, i R« maja wyzej podane znaczenia. Fh 0 Ri \ II / N-C-N R2 WZÓR 1 *^r N-C=0 WZCfR 2 /Rl HN R2 WZtfR 3 Pracownia Poligraficzna UP PRL. Naklad 100 egz. Cena 400 zl
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/342,693 US4473579A (en) | 1982-01-26 | 1982-01-26 | Antiatherosclerotic tetrasubstituted ureas and thioureas |
| US06/342,698 US4387105A (en) | 1982-01-26 | 1982-01-26 | Methods of treating atherosclerosis with dialkylureas and dialkylthioureas |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL240284A1 PL240284A1 (en) | 1985-01-02 |
| PL143836B1 true PL143836B1 (en) | 1988-03-31 |
Family
ID=26993144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1983240284A PL143836B1 (en) | 1982-01-26 | 1983-01-25 | Method of obtaining novel substituted ureas |
Country Status (20)
| Country | Link |
|---|---|
| KR (1) | KR890001808B1 (pl) |
| AT (1) | AT391313B (pl) |
| AU (1) | AU562699B2 (pl) |
| CH (1) | CH654571A5 (pl) |
| DE (1) | DE3247581A1 (pl) |
| DK (1) | DK160869C (pl) |
| ES (2) | ES8406422A1 (pl) |
| FI (1) | FI85013C (pl) |
| FR (1) | FR2521134B1 (pl) |
| GB (1) | GB2113684B (pl) |
| GR (1) | GR77186B (pl) |
| HU (1) | HU200746B (pl) |
| IE (1) | IE54683B1 (pl) |
| IL (1) | IL67417A (pl) |
| IT (1) | IT1203647B (pl) |
| NL (1) | NL8300269A (pl) |
| NO (1) | NO158417C (pl) |
| PL (1) | PL143836B1 (pl) |
| PT (1) | PT76138A (pl) |
| SE (1) | SE462653B (pl) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2138804A (en) * | 1983-04-27 | 1984-10-31 | Sumitomo Chemical Co | Fungicidal N-phenylcarbamates |
| GB2149394B (en) * | 1983-07-19 | 1986-09-24 | American Cyanamid Co | Ureas |
| US4818899A (en) * | 1986-12-03 | 1989-04-04 | Minnesota Mining And Manufacturing Company | Second harmonic generation by carbamic acid derivatives |
| US5116848A (en) * | 1988-03-30 | 1992-05-26 | Warner-Lambert Company | N-(((2,6-disubstituted)phenyl)-n-diarylalkyl)ureas as antihyperlipidemic and antiatherosclerotic agents |
| ATE98223T1 (de) * | 1988-03-30 | 1993-12-15 | Warner Lambert Co | N-(((2,6-disubstituierte)phenyl>n'- arylalkyl> harnstoffe als antihypercholesterolemische und antiatherosclerotische mittel. |
| WO1991011994A1 (en) * | 1990-02-14 | 1991-08-22 | Chugai Seiyaku Kabushiki Kaisha | Inhibitor of denatured ldl formation |
| US5668136A (en) * | 1990-09-25 | 1997-09-16 | Eisai Co., Ltd. | Trisubstituted benzene derivatives, composition and methods of treatment |
| HUT62558A (en) * | 1991-07-01 | 1993-05-28 | Sandoz Ag | Process for producing n-phenylthiourea derivaties and pharmaceutical compositions comprising same |
| JP3612328B2 (ja) * | 1992-07-20 | 2005-01-19 | エーザイ株式会社 | ベンゼン誘導体 |
| JP2003524574A (ja) * | 1997-08-05 | 2003-08-19 | ノボ ノルディスク アクティーゼルスカブ | ２，５−及び３，５−二置換アニリン誘導体、その調製及び使用 |
| TW415942B (en) * | 1997-09-03 | 2000-12-21 | American Home Prod | Novel substituted 1-aryl-3-heteroaryl-thioureas and substituted 1-aryl-3-heteroaryl-isothioureas as antiatherosclerotic agents |
| US6455566B1 (en) | 1997-09-03 | 2002-09-24 | Wyeth | Substituted 1-aryl-3-heteroaryl-thioureas (or isothioureas) as antiatherosclerotic agents |
| CA2284864A1 (en) * | 1998-01-21 | 1999-07-29 | Zymogenetics, Inc. | Dialkyl ureas as calcitonin mimetics |
| WO2009009122A2 (en) * | 2007-07-10 | 2009-01-15 | Amgen Inc. | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL212631A (pl) * | 1949-12-06 | |||
| US2688039A (en) * | 1952-02-08 | 1954-08-31 | Ciba Pharm Prod Inc | Halogen-containing di-(substituted phenyl)-thioureas |
| US3326663A (en) * | 1964-09-25 | 1967-06-20 | Shell Oil Co | Herbicidal phenylureas |
| US3335142A (en) * | 1965-07-07 | 1967-08-08 | American Cyanamid Co | Process for the preparation of n, n'-disubstituted ureas |
| US3659012A (en) * | 1969-05-26 | 1972-04-25 | Lilly Co Eli | Methods of treating helminth infections with thiourea derivatives |
| US3728386A (en) * | 1970-07-27 | 1973-04-17 | Exxon Research Engineering Co | N-cycloalkylalkyl and n-cycloalkyl substituted phenyl ureas and halo acetamides |
| US3928437A (en) * | 1970-09-02 | 1975-12-23 | Ciba Geigy Corp | Phenoxy-phenyl, phenylthiophenyl, phenylsulfonylphenyl and phenylaminophenyl diaminothioureas |
| US3856952A (en) * | 1973-03-01 | 1974-12-24 | Pennwalt Corp | Synergistic antimicrobial compositions employing certain n-(phenyl-carbamyl)amino-benzene sulfonyl flourides |
| US3903130A (en) * | 1974-05-03 | 1975-09-02 | Stauffer Chemical Co | 1-Trifluormethylphenyl-3-dicyanophenyl urea |
| DE2928485A1 (de) * | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
-
1982
- 1982-12-05 IL IL67417A patent/IL67417A/xx not_active IP Right Cessation
- 1982-12-22 DE DE19823247581 patent/DE3247581A1/de not_active Withdrawn
- 1982-12-28 KR KR8205843A patent/KR890001808B1/ko active
-
1983
- 1983-01-14 GR GR70261A patent/GR77186B/el unknown
- 1983-01-21 AU AU10681/83A patent/AU562699B2/en not_active Ceased
- 1983-01-24 GB GB08301863A patent/GB2113684B/en not_active Expired
- 1983-01-25 CH CH404/83A patent/CH654571A5/de not_active IP Right Cessation
- 1983-01-25 IE IE146/83A patent/IE54683B1/en not_active IP Right Cessation
- 1983-01-25 NO NO830238A patent/NO158417C/no unknown
- 1983-01-25 NL NL8300269A patent/NL8300269A/nl not_active Application Discontinuation
- 1983-01-25 ES ES519246A patent/ES8406422A1/es not_active Expired
- 1983-01-25 PL PL1983240284A patent/PL143836B1/pl unknown
- 1983-01-25 AT AT0023983A patent/AT391313B/de not_active IP Right Cessation
- 1983-01-25 DK DK028683A patent/DK160869C/da not_active IP Right Cessation
- 1983-01-25 PT PT76138A patent/PT76138A/pt not_active IP Right Cessation
- 1983-01-25 IT IT47605/83A patent/IT1203647B/it active
- 1983-01-25 HU HU83227A patent/HU200746B/hu not_active IP Right Cessation
- 1983-01-25 FI FI830247A patent/FI85013C/fi not_active IP Right Cessation
- 1983-01-25 FR FR8301082A patent/FR2521134B1/fr not_active Expired
- 1983-01-25 SE SE8300370A patent/SE462653B/sv not_active IP Right Cessation
-
1984
- 1984-04-11 ES ES531508A patent/ES531508A0/es active Granted
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