DE3149478C2 - - Google Patents
Info
- Publication number
- DE3149478C2 DE3149478C2 DE3149478A DE3149478A DE3149478C2 DE 3149478 C2 DE3149478 C2 DE 3149478C2 DE 3149478 A DE3149478 A DE 3149478A DE 3149478 A DE3149478 A DE 3149478A DE 3149478 C2 DE3149478 C2 DE 3149478C2
- Authority
- DE
- Germany
- Prior art keywords
- group
- compound
- methyl
- mixture
- general formula
- 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 claims description 39
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- -1 hydroxy, methoxy Chemical group 0.000 claims description 8
- 230000000202 analgesic effect Effects 0.000 claims description 6
- 230000001754 anti-pyretic effect Effects 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N isourea group Chemical group NC(O)=N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000829 suppository Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
- 229960003415 propylparaben Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RQKFYFNZSHWXAW-UHFFFAOYSA-N 3-chloro-p-toluidine Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 3
- KRNMSEFCRXHLRW-UHFFFAOYSA-N 5-methyl-1h-imidazole-4-carboxylic acid;hydrochloride Chemical compound Cl.CC=1NC=NC=1C(O)=O KRNMSEFCRXHLRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- NMIZONYLXCOHEF-UHFFFAOYSA-N 1h-imidazole-2-carboxamide Chemical compound NC(=O)C1=NC=CN1 NMIZONYLXCOHEF-UHFFFAOYSA-N 0.000 description 2
- RZLXZNBOXJDOCU-UHFFFAOYSA-N 5-methyl-1h-imidazole-4-carbonyl chloride;hydrochloride Chemical compound Cl.CC=1N=CNC=1C(Cl)=O RZLXZNBOXJDOCU-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 210000001156 gastric mucosa Anatomy 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- YJDAWQKGDLDHGU-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-5-methyl-1h-imidazole-4-carboxamide Chemical compound N1C=NC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C YJDAWQKGDLDHGU-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical compound C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JBOQEFIUVWTFJV-UHFFFAOYSA-N 5-methyl-1h-imidazole-4-carbonyl chloride Chemical compound CC=1NC=NC=1C(Cl)=O JBOQEFIUVWTFJV-UHFFFAOYSA-N 0.000 description 1
- ULHLTDXPKWELHQ-UHFFFAOYSA-N 5-methyl-imidazole-4-carboxylic acid Chemical compound CC=1NC=NC=1C(O)=O ULHLTDXPKWELHQ-UHFFFAOYSA-N 0.000 description 1
- ZGEZGJOBIVJVEQ-UHFFFAOYSA-N 5-methyl-n-(2,4,6-trimethylphenyl)-1h-imidazole-4-carboxamide Chemical compound N1C=NC(C(=O)NC=2C(=CC(C)=CC=2C)C)=C1C ZGEZGJOBIVJVEQ-UHFFFAOYSA-N 0.000 description 1
- HFACYQDTELBSKV-UHFFFAOYSA-N 5-methyl-n-(3-methyl-4-nitrophenyl)-1h-imidazole-4-carboxamide Chemical compound N1C=NC(C(=O)NC=2C=C(C)C(=CC=2)[N+]([O-])=O)=C1C HFACYQDTELBSKV-UHFFFAOYSA-N 0.000 description 1
- UIUAFOLNWPBDHU-UHFFFAOYSA-N 5-methyl-n-[2-(trifluoromethyl)phenyl]-1h-imidazole-4-carboxamide Chemical compound N1C=NC(C(=O)NC=2C(=CC=CC=2)C(F)(F)F)=C1C UIUAFOLNWPBDHU-UHFFFAOYSA-N 0.000 description 1
- HZVBAHLWXBSJNJ-UHFFFAOYSA-N 5-methyl-n-phenyl-1h-imidazole-4-carboxamide Chemical class N1C=NC(C(=O)NC=2C=CC=CC=2)=C1C HZVBAHLWXBSJNJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229960000212 aminophenazone Drugs 0.000 description 1
- 229960004977 anhydrous lactose Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- IJXCPBJIHVODNQ-UHFFFAOYSA-N n-(2-fluorophenyl)-5-methyl-1h-imidazole-4-carboxamide Chemical compound N1C=NC(C(=O)NC=2C(=CC=CC=2)F)=C1C IJXCPBJIHVODNQ-UHFFFAOYSA-N 0.000 description 1
- GZWMYPBGEUHYBL-UHFFFAOYSA-N n-(2-methoxyphenyl)-5-methyl-1h-imidazole-4-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=C(C)NC=N1 GZWMYPBGEUHYBL-UHFFFAOYSA-N 0.000 description 1
- FSURPMDDQOPNEZ-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)-5-methyl-1h-imidazole-4-carboxamide Chemical compound N1C=NC(C(=O)NC=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1C FSURPMDDQOPNEZ-UHFFFAOYSA-N 0.000 description 1
- BERVCLNJJSCKJQ-UHFFFAOYSA-N n-(5-chloro-2-methoxyphenyl)-5-methyl-1h-imidazole-4-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)C1=C(C)NC=N1 BERVCLNJJSCKJQ-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES502162A ES502162A0 (es) | 1981-04-16 | 1981-04-16 | Procedimiento para la obtencion de derivados del imidazol. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3149478A1 DE3149478A1 (de) | 1982-11-04 |
| DE3149478C2 true DE3149478C2 (en, 2012) | 1989-07-13 |
Family
ID=8482378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813149478 Granted DE3149478A1 (de) | 1981-04-16 | 1981-12-14 | Imidazol-derivate |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4539331A (en, 2012) |
| JP (1) | JPS57175172A (en, 2012) |
| AU (1) | AU540226B2 (en, 2012) |
| BE (1) | BE891468A (en, 2012) |
| CH (1) | CH650255A5 (en, 2012) |
| DE (1) | DE3149478A1 (en, 2012) |
| ES (1) | ES502162A0 (en, 2012) |
| FR (1) | FR2504133A1 (en, 2012) |
| GB (1) | GB2096990B (en, 2012) |
| IE (1) | IE51950B1 (en, 2012) |
| IL (1) | IL64449A0 (en, 2012) |
| IT (1) | IT1142102B (en, 2012) |
| NL (1) | NL8105568A (en, 2012) |
| NZ (1) | NZ199228A (en, 2012) |
| SE (1) | SE8107470L (en, 2012) |
| ZA (1) | ZA818689B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10017362A1 (de) * | 2000-04-07 | 2001-10-18 | Infineon Technologies Ag | Einrichtung und Verfahren zur Datenübergabe zwischen zwei Recheneinheiten |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4578386A (en) * | 1984-02-10 | 1986-03-25 | Usv Pharmaceutical Corp. | 7,8-Dihydroimidazo[1,5-a]pyrazin-8-ones |
| US5073566A (en) * | 1989-11-30 | 1991-12-17 | Eli Lilly And Company | Angiotensin ii antagonist 1,3-imidazoles and use thereas |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE140966C (en, 2012) * | ||||
| US3303199A (en) * | 1963-07-15 | 1967-02-07 | Geigy Chem Corp | Certain imidazolone derivatives and process for making same |
| US3438992A (en) * | 1966-11-09 | 1969-04-15 | Merck & Co Inc | Certain lower-alkyl sulfinylmethyl pyridines |
| US3558640A (en) * | 1967-12-20 | 1971-01-26 | Merck & Co Inc | Certain pyridyl and thiazolyl methylthiopropionic acids and derivatives |
| US3668212A (en) * | 1968-12-12 | 1972-06-06 | Merck & Co Inc | Methylsulfinylmethylthiazole |
| GB1360982A (en) * | 1970-08-27 | 1974-07-24 | Beecham Group Ltd | Derivatives of 1-phenyl-5-aminoimidazole and compositions thereof |
| BE795808A (fr) * | 1972-02-24 | 1973-08-22 | Beecham Group Ltd | Amidazoles polysubstitues |
| JPS53101373A (en) * | 1977-02-17 | 1978-09-04 | Kanebo Ltd | Imidazole-4(5)-carboxylic acid anilide derivatives |
-
1981
- 1981-04-16 ES ES502162A patent/ES502162A0/es active Granted
- 1981-12-03 AU AU78228/81A patent/AU540226B2/en not_active Ceased
- 1981-12-04 IL IL64449A patent/IL64449A0/xx unknown
- 1981-12-07 GB GB8136780A patent/GB2096990B/en not_active Expired
- 1981-12-10 FR FR8123082A patent/FR2504133A1/fr active Granted
- 1981-12-10 NZ NZ199228A patent/NZ199228A/en unknown
- 1981-12-10 NL NL8105568A patent/NL8105568A/nl not_active Application Discontinuation
- 1981-12-14 CH CH7954/81A patent/CH650255A5/fr not_active IP Right Cessation
- 1981-12-14 IE IE2941/81A patent/IE51950B1/en unknown
- 1981-12-14 SE SE8107470A patent/SE8107470L/xx not_active Application Discontinuation
- 1981-12-14 DE DE19813149478 patent/DE3149478A1/de active Granted
- 1981-12-14 BE BE0/206826A patent/BE891468A/fr not_active IP Right Cessation
- 1981-12-15 JP JP56202369A patent/JPS57175172A/ja active Granted
- 1981-12-15 ZA ZA818689A patent/ZA818689B/xx unknown
- 1981-12-15 IT IT25592/81A patent/IT1142102B/it active
-
1984
- 1984-02-21 US US06/581,651 patent/US4539331A/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10017362A1 (de) * | 2000-04-07 | 2001-10-18 | Infineon Technologies Ag | Einrichtung und Verfahren zur Datenübergabe zwischen zwei Recheneinheiten |
| DE10017362B4 (de) * | 2000-04-07 | 2004-02-12 | Infineon Technologies Ag | Einrichtung und Verfahren zur Datenübergabe zwischen zwei Recheneinheiten |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8125592A0 (it) | 1981-12-15 |
| AU540226B2 (en) | 1984-11-08 |
| FR2504133A1 (fr) | 1982-10-22 |
| JPS57175172A (en) | 1982-10-28 |
| IE51950B1 (en) | 1987-04-29 |
| BE891468A (fr) | 1982-03-31 |
| FR2504133B1 (en, 2012) | 1984-12-14 |
| US4539331A (en) | 1985-09-03 |
| IL64449A0 (en) | 1982-03-31 |
| ZA818689B (en) | 1982-11-24 |
| ES8207519A1 (es) | 1982-10-01 |
| JPH0216302B2 (en, 2012) | 1990-04-16 |
| ES502162A0 (es) | 1982-10-01 |
| DE3149478A1 (de) | 1982-11-04 |
| IE812941L (en) | 1982-10-16 |
| CH650255A5 (fr) | 1985-07-15 |
| NL8105568A (nl) | 1982-11-16 |
| GB2096990A (en) | 1982-10-27 |
| SE8107470L (sv) | 1982-10-17 |
| NZ199228A (en) | 1984-05-31 |
| GB2096990B (en) | 1984-06-13 |
| AU7822881A (en) | 1982-10-21 |
| IT1142102B (it) | 1986-10-08 |
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| 8101 | Request for examination as to novelty | ||
| 8105 | Search report available | ||
| 8126 | Change of the secondary classification |
Ipc: C07D233/90 |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |