HU185018B - Process for the preparation of alkyl-urea derivatives, as well as pharmaceutical compositions sontaining said compounds - Google Patents
Process for the preparation of alkyl-urea derivatives, as well as pharmaceutical compositions sontaining said compounds Download PDFInfo
- Publication number
- HU185018B HU185018B HU802647A HU264780A HU185018B HU 185018 B HU185018 B HU 185018B HU 802647 A HU802647 A HU 802647A HU 264780 A HU264780 A HU 264780A HU 185018 B HU185018 B HU 185018B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- defined above
- compound
- alkyl
- compounds
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- -1 methylene, ethylene, 1,2-propylene, 1,2-propenylene Chemical group 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 3
- 230000004060 metabolic process Effects 0.000 claims 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 2
- 230000002195 synergetic effect Effects 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- KSNRDYQOHXQKAB-UHFFFAOYSA-N 2,2,4-trimethyl-3,4-dihydro-1h-quinoline Chemical compound C1=CC=C2C(C)CC(C)(C)NC2=C1 KSNRDYQOHXQKAB-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 239000004006 olive oil Substances 0.000 description 6
- 235000008390 olive oil Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 5
- 239000012973 diazabicyclooctane Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
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- 241000416162 Astragalus gummifer Species 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 235000010487 tragacanth Nutrition 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- QRWRJDVVXAXGBT-UHFFFAOYSA-N 2-Methylindoline Chemical compound C1=CC=C2NC(C)CC2=C1 QRWRJDVVXAXGBT-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- DBTXKKVNZQBWLP-UHFFFAOYSA-N 1-hexyl-2-methyl-3h-indole-2-carboxamide Chemical compound C1=CC=C2CC(C(N)=O)(C)N(CCCCCC)C2=C1 DBTXKKVNZQBWLP-UHFFFAOYSA-N 0.000 description 1
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
- OVSDUSCJLIXRAU-UHFFFAOYSA-N 2,2,4-trimethyl-n-octyl-3,4-dihydroquinoline-1-carboxamide Chemical compound C1=CC=C2C(C)CC(C)(C)N(C(=O)NCCCCCCCC)C2=C1 OVSDUSCJLIXRAU-UHFFFAOYSA-N 0.000 description 1
- SAVUMXSYABQGLT-UHFFFAOYSA-N 6-butoxy-2,2,4-trimethyl-n-octyl-3,4-dihydroquinoline-1-carboxamide Chemical compound C1=C(OCCCC)C=C2C(C)CC(C)(C)N(C(=O)NCCCCCCCC)C2=C1 SAVUMXSYABQGLT-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
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- XQKRPEDJRVOOAA-UHFFFAOYSA-J [Mg+2].[Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O Chemical compound [Mg+2].[Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XQKRPEDJRVOOAA-UHFFFAOYSA-J 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792945238 DE2945238A1 (de) | 1979-11-09 | 1979-11-09 | Verwendung von alkylharnstoffderivaten in arzneimitteln zur behandlung von fettstoffwechselstoerungen |
| DE19803030024 DE3030024A1 (de) | 1980-08-08 | 1980-08-08 | Alkylharnstoffderivate zur behandlung von erkrankungen des fettstoffwechsels, verfahren zu deren herstellung, deren verwendung in arzneimitteln zur behandlung von festtstoffwechselstoerungen, diese enthaltende arzneimittel und verfahren zur herstellung der arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185018B true HU185018B (en) | 1984-11-28 |
Family
ID=25781919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU802647A HU185018B (en) | 1979-11-09 | 1980-11-03 | Process for the preparation of alkyl-urea derivatives, as well as pharmaceutical compositions sontaining said compounds |
Country Status (10)
| Country | Link |
|---|---|
| US (4) | US4510156A (index.php) |
| EP (1) | EP0028765B1 (index.php) |
| AU (1) | AU538478B2 (index.php) |
| CA (1) | CA1191133A (index.php) |
| DE (1) | DE3062981D1 (index.php) |
| DK (1) | DK475380A (index.php) |
| ES (1) | ES496650A0 (index.php) |
| GR (1) | GR72127B (index.php) |
| HU (1) | HU185018B (index.php) |
| NO (1) | NO156087B (index.php) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5003106A (en) * | 1983-07-19 | 1991-03-26 | American Cyanamid Company | Antiatherosclerotic ureas and thioureas |
| DE3738237A1 (de) * | 1987-11-11 | 1989-05-24 | Bayer Ag | Bis-indolyl-ethylen |
| DE3738238A1 (de) * | 1987-11-11 | 1989-05-24 | Bayer Ag | Bis-indolyl-ethylen-aldehyde |
| US6673334B1 (en) * | 2000-10-16 | 2004-01-06 | Mallinkcrodt, Inc. | Light sensitive compounds for instant determination of organ function |
| US6669926B1 (en) * | 2000-10-16 | 2003-12-30 | Mallinckrodt, Inc. | Hydrophilic light absorbing indole compounds for determination of physiological function in critically ill patients |
| US7297286B2 (en) * | 2002-07-29 | 2007-11-20 | Nanoclean Technologies, Inc. | Methods for resist stripping and other processes for cleaning surfaces substantially free of contaminants |
| US7101260B2 (en) * | 2002-07-29 | 2006-09-05 | Nanoclean Technologies, Inc. | Methods for resist stripping and other processes for cleaning surfaces substantially free of contaminants |
| US7134941B2 (en) * | 2002-07-29 | 2006-11-14 | Nanoclean Technologies, Inc. | Methods for residue removal and corrosion prevention in a post-metal etch process |
| US7066789B2 (en) * | 2002-07-29 | 2006-06-27 | Manoclean Technologies, Inc. | Methods for resist stripping and other processes for cleaning surfaces substantially free of contaminants |
| US6764385B2 (en) * | 2002-07-29 | 2004-07-20 | Nanoclean Technologies, Inc. | Methods for resist stripping and cleaning surfaces substantially free of contaminants |
| TWI329102B (en) * | 2006-08-15 | 2010-08-21 | Nat Health Research Institutes | Thiourea compounds and method for inhibiting hepatitis c virus infection |
| US7985763B2 (en) * | 2007-04-10 | 2011-07-26 | National Health Research Institutes | Hepatitis C virus inhibitors |
| TW200848016A (en) * | 2007-06-08 | 2008-12-16 | Nat Health Research Institutes | Thiourea compound and composition of treating hepatitis C virus infection |
| US8198284B2 (en) * | 2008-04-30 | 2012-06-12 | National Health Research Institutes | Treatment of neurodegenerative disorders with thiourea compounds |
| HRP20210431T1 (hr) | 2013-11-18 | 2021-05-14 | Forma Therapeutics, Inc. | Pripravci tetrahidrokinolina kao inhibitori bet bromodomene |
| RU2720237C2 (ru) | 2013-11-18 | 2020-04-28 | Форма Терапеутикс, Инк. | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет |
| US20220380314A1 (en) * | 2019-09-17 | 2022-12-01 | Bial - R&D Investments, S.A. | Substituted, saturated and unsaturated n-heterocyclic carboxamides and related compounds for their use in the treatment of medical disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2364347A (en) * | 1940-09-26 | 1944-12-05 | Eastman Kodak Co | Nitrogen heterocyclic compounds |
| US3143545A (en) * | 1961-11-27 | 1964-08-04 | Searle & Co | 4-aminoalkanoyl-2-phenyl-3, 4-dihydro-2h-1, 4-benzothiazines |
| US3880847A (en) * | 1969-04-05 | 1975-04-29 | Bayer Ag | Thiocarbamic acid derivatives |
| US3890348A (en) * | 1973-03-26 | 1975-06-17 | Sandoz Ag | Indole-1 and indoline-1-carboxamides and thiocarboxamides |
| GB1574019A (en) * | 1977-01-14 | 1980-09-03 | Joullie International Sa | Therapeutically useful 3,4,5-trimethoxybenzene derivatives |
| IL51342A (en) * | 1977-01-27 | 1980-11-30 | Abic Ltd | Ethoxyquin derivatives,their preparation and pharmaceutical and veterinary compositions comprising them |
-
1980
- 1980-10-29 DE DE8080106612T patent/DE3062981D1/de not_active Expired
- 1980-10-29 EP EP80106612A patent/EP0028765B1/de not_active Expired
- 1980-10-31 NO NO803266A patent/NO156087B/no unknown
- 1980-11-03 HU HU802647A patent/HU185018B/hu unknown
- 1980-11-07 ES ES496650A patent/ES496650A0/es active Granted
- 1980-11-07 GR GR63313A patent/GR72127B/el unknown
- 1980-11-07 CA CA000364269A patent/CA1191133A/en not_active Expired
- 1980-11-07 DK DK475380A patent/DK475380A/da not_active Application Discontinuation
- 1980-11-07 AU AU64189/80A patent/AU538478B2/en not_active Ceased
-
1982
- 1982-02-10 US US06/347,599 patent/US4510156A/en not_active Expired - Fee Related
- 1982-09-27 US US06/424,828 patent/US4460607A/en not_active Expired - Fee Related
- 1982-09-27 US US06/424,829 patent/US4466964A/en not_active Expired - Fee Related
-
1984
- 1984-01-23 US US06/573,168 patent/US4574124A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3062981D1 (en) | 1983-06-09 |
| US4466964A (en) | 1984-08-21 |
| ES8200094A1 (es) | 1981-10-16 |
| AU538478B2 (en) | 1984-08-16 |
| US4574124A (en) | 1986-03-04 |
| NO803266L (no) | 1981-05-11 |
| EP0028765B1 (de) | 1983-05-04 |
| US4510156A (en) | 1985-04-09 |
| CA1191133A (en) | 1985-07-30 |
| ES496650A0 (es) | 1981-10-16 |
| GR72127B (index.php) | 1983-09-16 |
| NO156087B (no) | 1987-04-13 |
| US4460607A (en) | 1984-07-17 |
| EP0028765A1 (de) | 1981-05-20 |
| DK475380A (da) | 1981-05-10 |
| AU6418980A (en) | 1981-05-14 |
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