CA1047042A - Thienyl and thietyl compounds - Google Patents
Thienyl and thietyl compoundsInfo
- Publication number
- CA1047042A CA1047042A CA224,634A CA224634A CA1047042A CA 1047042 A CA1047042 A CA 1047042A CA 224634 A CA224634 A CA 224634A CA 1047042 A CA1047042 A CA 1047042A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- compound
- tert
- urea
- thienyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- 125000001544 thienyl group Chemical group 0.000 title abstract description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000004202 carbamide Substances 0.000 claims abstract description 19
- ZJEBGSGYSRSENA-UHFFFAOYSA-N 1-tert-butyl-3-(2,3-dihydrothiophen-4-yl)urea Chemical compound CC(C)(C)NC(=O)NC1=CSCC1 ZJEBGSGYSRSENA-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 159000000007 calcium salts Chemical class 0.000 claims 3
- DUUSUVFTWMHSJT-UHFFFAOYSA-N 1-(2-methylbutan-2-yl)-3-(3-methyl-2,3-dihydrothiophen-4-yl)urea Chemical compound CCC(C)(C)NC(=O)NC1=CSCC1C DUUSUVFTWMHSJT-UHFFFAOYSA-N 0.000 claims 1
- YMVAAGWNXIAADD-UHFFFAOYSA-N 1-(2-methylbutan-2-yl)-3-(4-methyl-2h-thiet-3-yl)urea Chemical compound CCC(C)(C)NC(=O)NC1=C(C)SC1 YMVAAGWNXIAADD-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 8
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
- 235000013877 carbamide Nutrition 0.000 abstract 3
- 150000003672 ureas Chemical class 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000000376 reactant Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 206010020772 Hypertension Diseases 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 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 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 amyl-3-(5-methyl-4,5-dihydro-3-thienyl)urea Chemical compound 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZNFFXBMYRMWPNU-UHFFFAOYSA-N 1-tert-butyl-3-(3-methyl-2,3-dihydrothiophen-4-yl)urea Chemical compound CC1CSC=C1NC(=O)NC(C)(C)C ZNFFXBMYRMWPNU-UHFFFAOYSA-N 0.000 description 1
- RCDLDAQNYJHKSB-UHFFFAOYSA-N 2-methylthietan-3-one Chemical compound CC1SCC1=O RCDLDAQNYJHKSB-UHFFFAOYSA-N 0.000 description 1
- CGLTVEXYPJALGS-UHFFFAOYSA-N 4-methyl-1,1-dioxothiolan-3-one Chemical compound CC1CS(=O)(=O)CC1=O CGLTVEXYPJALGS-UHFFFAOYSA-N 0.000 description 1
- CGCRKRJUWOOJMO-UHFFFAOYSA-N 4-methylthiolan-3-one Chemical compound CC1CSCC1=O CGCRKRJUWOOJMO-UHFFFAOYSA-N 0.000 description 1
- ZQMVZNAFLSJGOS-UHFFFAOYSA-N 5-methyl-1,1-dioxothiolan-3-one Chemical group CC1CC(=O)CS1(=O)=O ZQMVZNAFLSJGOS-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 101150096839 Fcmr gene Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000290333 Vanilla fragrans Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WHSVYFAUHAUURG-UHFFFAOYSA-N benzene;ethyl acetate;methanol Chemical compound OC.CCOC(C)=O.C1=CC=CC=C1 WHSVYFAUHAUURG-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229960004486 desoxycorticosterone acetate Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- KOWWOODYPWDWOJ-LVBPXUMQSA-N elatine Chemical compound C([C@]12CN(C3[C@@]45OCO[C@]44[C@H]6[C@@H](OC)[C@@H]([C@H](C4)OC)C[C@H]6[C@@]3([C@@H]1[C@@H]5OC)[C@@H](OC)CC2)CC)OC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O KOWWOODYPWDWOJ-LVBPXUMQSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000004873 systolic arterial blood pressure Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 1
- DQOHDRDDPZNSQI-UHFFFAOYSA-N thietan-3-one Chemical compound O=C1CSC1 DQOHDRDDPZNSQI-UHFFFAOYSA-N 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
- C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/04—Four-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46169974A | 1974-04-17 | 1974-04-17 | |
| US05/555,307 US4009847A (en) | 1974-04-17 | 1975-03-11 | 1-Tertiary-alkyl-3-(substituted thienyl)ureas and 1-tertiary-alkyl-3-(substituted thietyl)ureas as antihypertensive agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047042A true CA1047042A (en) | 1979-01-23 |
Family
ID=27040095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA224,634A Expired CA1047042A (en) | 1974-04-17 | 1975-04-15 | Thienyl and thietyl compounds |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4009847A (en, 2012) |
| JP (1) | JPS50148349A (en, 2012) |
| AR (1) | AR208545A1 (en, 2012) |
| CA (1) | CA1047042A (en, 2012) |
| CH (1) | CH611292A5 (en, 2012) |
| DD (1) | DD117223A5 (en, 2012) |
| DE (1) | DE2516554A1 (en, 2012) |
| DK (1) | DK164175A (en, 2012) |
| ES (1) | ES436648A1 (en, 2012) |
| FI (1) | FI751128A7 (en, 2012) |
| FR (1) | FR2267773B1 (en, 2012) |
| GB (1) | GB1461209A (en, 2012) |
| HU (1) | HU173052B (en, 2012) |
| IE (1) | IE41143B1 (en, 2012) |
| IL (1) | IL47095A (en, 2012) |
| LU (1) | LU72306A1 (en, 2012) |
| NL (1) | NL7504570A (en, 2012) |
| NO (1) | NO144071C (en, 2012) |
| PH (1) | PH11722A (en, 2012) |
| SE (1) | SE417965B (en, 2012) |
| YU (1) | YU96075A (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4156738A (en) * | 1977-10-07 | 1979-05-29 | E. I. Du Pont De Nemours And Company | Ureidonitriles useful as antihypertensives |
| US6344476B1 (en) | 1997-05-23 | 2002-02-05 | Bayer Corporation | Inhibition of p38 kinase activity by aryl ureas |
| US6187799B1 (en) * | 1997-05-23 | 2001-02-13 | Onyx Pharmaceuticals | Inhibition of raf kinase activity using aryl ureas |
| US7329670B1 (en) * | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
| US7517880B2 (en) * | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| US20080300281A1 (en) * | 1997-12-22 | 2008-12-04 | Jacques Dumas | Inhibition of p38 Kinase Activity Using Aryl and Heteroaryl Substituted Heterocyclic Ureas |
| US20080269265A1 (en) * | 1998-12-22 | 2008-10-30 | Scott Miller | Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas |
| US7928239B2 (en) | 1999-01-13 | 2011-04-19 | Bayer Healthcare Llc | Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas |
| WO2000042012A1 (en) | 1999-01-13 | 2000-07-20 | Bayer Corporation | φ-CARBOXYARYL SUBSTITUTED DIPHENYL UREAS AS RAF KINASE INHIBITORS |
| WO2000041698A1 (en) * | 1999-01-13 | 2000-07-20 | Bayer Corporation | φ-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7351834B1 (en) | 1999-01-13 | 2008-04-01 | Bayer Pharmaceuticals Corporation | ω-Carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7235576B1 (en) | 2001-01-12 | 2007-06-26 | Bayer Pharmaceuticals Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7371763B2 (en) * | 2001-04-20 | 2008-05-13 | Bayer Pharmaceuticals Corporation | Inhibition of raf kinase using quinolyl, isoquinolyl or pyridyl ureas |
| EP2295057B1 (en) * | 2001-12-03 | 2013-01-23 | Bayer HealthCare LLC | Aryl urea compounds in combination with other cytostatic or cytotoxic agents for treating human cancers |
| US20080108672A1 (en) * | 2002-01-11 | 2008-05-08 | Bernd Riedl | Omega-Carboxyaryl Substituted Diphenyl Ureas As Raf Kinase Inhibitors |
| US20040023961A1 (en) * | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
| AU2003209118A1 (en) | 2002-02-11 | 2003-09-04 | Bayer Pharmaceuticals Corporation | Aryl ureas as kinase inhibitors |
| AU2003209119A1 (en) * | 2002-02-11 | 2003-09-04 | Bayer Pharmaceuticals Corporation | Pyridine, quinoline, and isoquinoline n-oxides as kinase inhibitors |
| EP2324825A1 (en) * | 2002-02-11 | 2011-05-25 | Bayer Healthcare LLC | Aryl ureas with angiogenesis inhibiting activity |
| US7557129B2 (en) * | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| DE602004011340T2 (de) * | 2003-05-20 | 2008-11-06 | Bayer Healthcare Llc | Diaryl-harnstoffe mit kinasehemmender wirkung |
| PT1663978E (pt) * | 2003-07-23 | 2008-02-15 | Bayer Pharmaceuticals Corp | Omega-carboxiaril difenil ureia substituída por flúor para o tratamento e a prevenção de doenças e estados patológicos |
| WO2005110994A2 (en) * | 2004-04-30 | 2005-11-24 | Bayer Pharmaceuticals Corporation | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH452475A (de) * | 1965-05-20 | 1968-05-31 | Bayer Ag | Verfahren zum Färben und Bedrucken von synthetischem Textilmaterial mit Anthrachinonfarbstoffen |
-
1975
- 1975-03-11 US US05/555,307 patent/US4009847A/en not_active Expired - Lifetime
- 1975-03-26 SE SE7503523A patent/SE417965B/xx unknown
- 1975-04-15 CA CA224,634A patent/CA1047042A/en not_active Expired
- 1975-04-15 IL IL47095A patent/IL47095A/xx unknown
- 1975-04-16 NO NO751351A patent/NO144071C/no unknown
- 1975-04-16 PH PH17061A patent/PH11722A/en unknown
- 1975-04-16 FI FI751128A patent/FI751128A7/fi not_active Application Discontinuation
- 1975-04-16 FR FR7511796A patent/FR2267773B1/fr not_active Expired
- 1975-04-16 HU HU75DU237A patent/HU173052B/hu unknown
- 1975-04-16 DD DD185482A patent/DD117223A5/xx unknown
- 1975-04-16 YU YU00960/75A patent/YU96075A/xx unknown
- 1975-04-16 AR AR258396A patent/AR208545A1/es active
- 1975-04-16 ES ES436648A patent/ES436648A1/es not_active Expired
- 1975-04-16 DK DK164175A patent/DK164175A/da not_active IP Right Cessation
- 1975-04-16 DE DE19752516554 patent/DE2516554A1/de not_active Withdrawn
- 1975-04-16 GB GB1567175A patent/GB1461209A/en not_active Expired
- 1975-04-17 NL NL7504570A patent/NL7504570A/xx not_active Application Discontinuation
- 1975-04-17 JP JP50045924A patent/JPS50148349A/ja active Pending
- 1975-04-17 IE IE865/75A patent/IE41143B1/xx unknown
- 1975-04-17 CH CH494875A patent/CH611292A5/xx not_active IP Right Cessation
- 1975-04-17 LU LU72306A patent/LU72306A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE417965B (sv) | 1981-04-27 |
| SE7503523L (sv) | 1975-10-20 |
| PH11722A (en) | 1978-05-30 |
| NO144071B (no) | 1981-03-09 |
| IE41143B1 (en) | 1979-10-24 |
| DK164175A (da) | 1975-10-18 |
| CH611292A5 (en, 2012) | 1979-05-31 |
| IL47095A (en) | 1978-03-10 |
| FR2267773A1 (en, 2012) | 1975-11-14 |
| HU173052B (hu) | 1979-02-28 |
| NL7504570A (nl) | 1975-10-21 |
| NO751351L (en, 2012) | 1975-10-20 |
| FI751128A7 (en, 2012) | 1975-10-18 |
| IL47095A0 (en) | 1975-06-25 |
| JPS50148349A (en, 2012) | 1975-11-27 |
| ES436648A1 (es) | 1977-08-01 |
| LU72306A1 (en, 2012) | 1976-03-17 |
| YU96075A (en) | 1983-04-27 |
| AR208545A1 (es) | 1977-02-15 |
| FR2267773B1 (en, 2012) | 1978-08-18 |
| IE41143L (en) | 1975-10-17 |
| GB1461209A (en) | 1977-01-13 |
| US4009847A (en) | 1977-03-01 |
| AU8013575A (en) | 1976-10-21 |
| DE2516554A1 (de) | 1975-10-30 |
| DD117223A5 (en, 2012) | 1976-01-05 |
| NO144071C (no) | 1981-06-17 |
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