DE3237575A1 - Neue orale mopidamolformen - Google Patents
Neue orale mopidamolformenInfo
- Publication number
- DE3237575A1 DE3237575A1 DE19823237575 DE3237575A DE3237575A1 DE 3237575 A1 DE3237575 A1 DE 3237575A1 DE 19823237575 DE19823237575 DE 19823237575 DE 3237575 A DE3237575 A DE 3237575A DE 3237575 A1 DE3237575 A1 DE 3237575A1
- Authority
- DE
- Germany
- Prior art keywords
- mopidamol
- acid
- acidic
- auxiliaries
- forms according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- FOYWNSCCNCUEPU-UHFFFAOYSA-N mopidamol Chemical compound C12=NC(N(CCO)CCO)=NC=C2N=C(N(CCO)CCO)N=C1N1CCCCC1 FOYWNSCCNCUEPU-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 229950010718 mopidamol Drugs 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 27
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 40
- 230000002378 acidificating effect Effects 0.000 claims description 32
- 239000001530 fumaric acid Substances 0.000 claims description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 17
- 235000011087 fumaric acid Nutrition 0.000 claims description 17
- 239000008187 granular material Substances 0.000 claims description 17
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 14
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 14
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 14
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 14
- 239000002775 capsule Substances 0.000 claims description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 7
- 239000011975 tartaric acid Substances 0.000 claims description 7
- 235000002906 tartaric acid Nutrition 0.000 claims description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
- 239000000314 lubricant Substances 0.000 claims description 5
- 239000008188 pellet Substances 0.000 claims description 5
- 239000002966 varnish Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 239000001828 Gelatine Substances 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 229960005070 ascorbic acid Drugs 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 235000015165 citric acid Nutrition 0.000 claims description 3
- 238000007908 dry granulation Methods 0.000 claims description 3
- 239000003925 fat Substances 0.000 claims description 3
- 229920000159 gelatin Polymers 0.000 claims description 3
- 235000019322 gelatine Nutrition 0.000 claims description 3
- 239000001630 malic acid Substances 0.000 claims description 3
- 235000011090 malic acid Nutrition 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 230000000979 retarding effect Effects 0.000 claims description 3
- 238000005550 wet granulation Methods 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 229960003403 betaine hydrochloride Drugs 0.000 claims description 2
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000007906 compression Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000007903 gelatin capsule Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920001522 polyglycol ester Polymers 0.000 claims description 2
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims description 2
- 239000003232 water-soluble binding agent Substances 0.000 claims description 2
- 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 2
- 235000010944 ethyl methyl cellulose Nutrition 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 230000006835 compression Effects 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 239000001761 ethyl methyl cellulose Substances 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 239000004922 lacquer Substances 0.000 claims 1
- 229920003087 methylethyl cellulose Polymers 0.000 claims 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 13
- 150000003839 salts Chemical class 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 208000007536 Thrombosis Diseases 0.000 abstract 1
- 230000002785 anti-thrombosis Effects 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 230000036210 malignancy Effects 0.000 abstract 1
- 239000003826 tablet Substances 0.000 description 56
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 26
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000007941 film coated tablet Substances 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 15
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 14
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 14
- 235000019359 magnesium stearate Nutrition 0.000 description 13
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 13
- 229910002012 Aerosil® Inorganic materials 0.000 description 12
- 229920002261 Corn starch Polymers 0.000 description 12
- 239000008120 corn starch Substances 0.000 description 12
- 229940099112 cornstarch Drugs 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 12
- 230000036765 blood level Effects 0.000 description 11
- 238000001035 drying Methods 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- 230000036470 plasma concentration Effects 0.000 description 8
- 238000007873 sieving Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 4
- 239000001509 sodium citrate Substances 0.000 description 4
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 4
- 235000011083 sodium citrates Nutrition 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- -1 etc. Chemical compound 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 2
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- HWPKGOGLCKPRLZ-UHFFFAOYSA-M monosodium citrate Chemical compound [Na+].OC(=O)CC(O)(C([O-])=O)CC(O)=O HWPKGOGLCKPRLZ-UHFFFAOYSA-M 0.000 description 2
- 235000018342 monosodium citrate Nutrition 0.000 description 2
- 239000002524 monosodium citrate Substances 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- 239000002510 pyrogen Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 1
- RWHRFHQRVDUPIK-UHFFFAOYSA-N 50867-57-7 Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O RWHRFHQRVDUPIK-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- PCXFBLNXBPTBGZ-UHFFFAOYSA-L magnesium octadecanoate acetate Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)[O-].[Mg+2].C(C)(=O)[O-] PCXFBLNXBPTBGZ-UHFFFAOYSA-L 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002444 monopotassium citrate Substances 0.000 description 1
- 235000015861 monopotassium citrate Nutrition 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- WKZJASQVARUVAW-UHFFFAOYSA-M potassium;hydron;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [K+].OC(=O)CC(O)(C(O)=O)CC([O-])=O WKZJASQVARUVAW-UHFFFAOYSA-M 0.000 description 1
- 235000008476 powdered milk Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823237575 DE3237575A1 (de) | 1982-10-09 | 1982-10-09 | Neue orale mopidamolformen |
| AT83109510T ATE21481T1 (de) | 1982-10-09 | 1983-09-24 | Neue orale mopidamolformen. |
| DE8383109510T DE3365465D1 (en) | 1982-10-09 | 1983-09-24 | Oral galenical forms of mopidamol |
| EP83109510A EP0108898B1 (de) | 1982-10-09 | 1983-09-24 | Neue orale Mopidamolformen |
| FI833605A FI79650C (fi) | 1982-10-09 | 1983-10-05 | Foerfarande foer framstaellning av mopidamols instantformer. |
| DK460683A DK158541C (da) | 1982-10-09 | 1983-10-06 | Orale mopidamolformer og fremgangsmaade til deres fremstilling |
| NO833638A NO833638L (no) | 1982-10-09 | 1983-10-06 | Fremgangsmaate for fremstilling av nye orale mopidamolformer. |
| GB08326877A GB2128088B (en) | 1982-10-09 | 1983-10-07 | Oral mopidamol preparations |
| IE2358/83A IE56058B1 (en) | 1982-10-09 | 1983-10-07 | New oral mopidamol preparations |
| US06/539,998 US4596705A (en) | 1982-10-09 | 1983-10-07 | Oral mopidamol preparation |
| ES526331A ES8500743A1 (es) | 1982-10-09 | 1983-10-07 | Procedimiento para preparar formas de mopidamol como granulados, granulos o tabletas |
| GR72641A GR79015B (enExample) | 1982-10-09 | 1983-10-07 | |
| ZA837499A ZA837499B (en) | 1982-10-09 | 1983-10-07 | Mopidamol preparations |
| IL69930A IL69930A (en) | 1982-10-09 | 1983-10-07 | Oral mopidamol preparations and their production |
| JP58188283A JPH07558B2 (ja) | 1982-10-09 | 1983-10-07 | モピダモール製剤 |
| CA000438670A CA1228546A (en) | 1982-10-09 | 1983-10-07 | Oral mopidamol preparations |
| NZ205894A NZ205894A (en) | 1982-10-09 | 1983-10-07 | Pharmaceutical compositions containing mopidamol(2,6-bis(diethanolamino)-4-piperidino-pyrimido(5,4-d)pyrimidine) |
| AU19985/83A AU560251B2 (en) | 1982-10-09 | 1983-10-07 | Pharmaceutical compositions of mopidamol |
| PT77467A PT77467B (de) | 1982-10-09 | 1983-10-07 | Neue orale mopidamolformen |
| US06/772,166 US4650664A (en) | 1982-10-09 | 1985-09-03 | Oral mopidamol preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823237575 DE3237575A1 (de) | 1982-10-09 | 1982-10-09 | Neue orale mopidamolformen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3237575A1 true DE3237575A1 (de) | 1984-04-12 |
Family
ID=6175408
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823237575 Withdrawn DE3237575A1 (de) | 1982-10-09 | 1982-10-09 | Neue orale mopidamolformen |
| DE8383109510T Expired DE3365465D1 (en) | 1982-10-09 | 1983-09-24 | Oral galenical forms of mopidamol |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383109510T Expired DE3365465D1 (en) | 1982-10-09 | 1983-09-24 | Oral galenical forms of mopidamol |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4596705A (enExample) |
| EP (1) | EP0108898B1 (enExample) |
| JP (1) | JPH07558B2 (enExample) |
| AT (1) | ATE21481T1 (enExample) |
| AU (1) | AU560251B2 (enExample) |
| CA (1) | CA1228546A (enExample) |
| DE (2) | DE3237575A1 (enExample) |
| DK (1) | DK158541C (enExample) |
| ES (1) | ES8500743A1 (enExample) |
| FI (1) | FI79650C (enExample) |
| GB (1) | GB2128088B (enExample) |
| GR (1) | GR79015B (enExample) |
| IE (1) | IE56058B1 (enExample) |
| IL (1) | IL69930A (enExample) |
| NO (1) | NO833638L (enExample) |
| NZ (1) | NZ205894A (enExample) |
| PT (1) | PT77467B (enExample) |
| ZA (1) | ZA837499B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4596705A (en) * | 1982-10-09 | 1986-06-24 | Dr. Karl Thomae Gmbh | Oral mopidamol preparation |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8414220D0 (en) * | 1984-06-04 | 1984-07-11 | Sterwin Ag | Medicaments in unit dose form |
| GB8524001D0 (en) * | 1985-09-30 | 1985-11-06 | Glaxo Group Ltd | Pharmaceutical composition |
| CA1323833C (en) * | 1987-04-28 | 1993-11-02 | Yatindra M. Joshi | Pharmaceutical compositions in the form of beadlets and method |
| US5364646A (en) * | 1990-01-10 | 1994-11-15 | Dr. Karl Thomae Gmbh | Oral pharmaceutical forms of pimobendan |
| CA2039742A1 (en) * | 1990-04-23 | 1991-10-24 | Andrew B. Dennis | Tablet composition and method for problem pharmaceutical materials |
| US5156845A (en) * | 1990-05-04 | 1992-10-20 | Colgate-Palmolive Company | Dry mouth lozenge |
| US5523289A (en) * | 1991-04-15 | 1996-06-04 | Abbott Laboratories | Pharmaceutical composition |
| WO1992020326A1 (en) * | 1991-05-20 | 1992-11-26 | Marion Laboratories, Inc. | Multi-layered controlled release formulation |
| EP1093814A1 (en) * | 1999-10-22 | 2001-04-25 | Boehringer Ingelheim Pharma KG | Use of dipyridamole or mopidamol in the manufacture of a medicament for the treatment and prevention of fibrin-dependent microcirculation disorders |
| MXPA02008403A (es) * | 2000-02-28 | 2004-09-27 | Vectura Ltd | Mejoras en o relacionadas con el suministro de farmacos por via oral. |
| US7064130B2 (en) * | 2001-04-20 | 2006-06-20 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Use of radical-scavenging compounds for treatment and prevention of NO-dependent microcirculation disorders |
| US20030181488A1 (en) | 2002-03-07 | 2003-09-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof |
| WO2004050068A1 (en) * | 2002-11-29 | 2004-06-17 | Janssen Pharmaceutica N.V. | Pharmaceutical compositions comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base |
| CN1747734A (zh) * | 2003-02-07 | 2006-03-15 | 贝林格尔·英格海姆国际有限公司 | 潘生丁或单哌潘生丁在治疗和预防mmp－9－依赖性疾病中的用途 |
| CN1812792A (zh) | 2003-04-24 | 2006-08-02 | 贝林格尔.英格海姆国际有限公司 | 双嘧达莫或单哌潘生丁用于治疗和预防凝血酶过量产生和/或凝血酶受体表达增加引起的血栓栓塞疾病和紊乱 |
| CA2536401C (en) * | 2003-11-04 | 2011-08-30 | Shire Laboratories Inc. | Compositions of quaternary ammonium compounds containing bioavailability enhancers |
| EP2210605B1 (en) * | 2003-11-04 | 2017-03-01 | TCD Royalty Sub, LLC | Once daily dosage forms of trospium |
| DE102004011512B4 (de) * | 2004-03-08 | 2022-01-13 | Boehringer Ingelheim Vetmedica Gmbh | Pharmazeutische Zubereitung enthaltend Pimobendan |
| EP1579862A1 (en) | 2004-03-25 | 2005-09-28 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the reduction of heart size in mammals suffering from heart failure |
| US8980894B2 (en) | 2004-03-25 | 2015-03-17 | Boehringer Ingelheim Vetmedica Gmbh | Use of PDE III inhibitors for the treatment of asymptomatic (occult) heart failure |
| US9205054B2 (en) | 2005-03-22 | 2015-12-08 | Losan Pharma Gmbh | Solubilized ibuprofen |
| EP1915137B8 (de) | 2005-08-10 | 2013-09-11 | ADD Advanced Drug Delivery Technologies, Ltd. | Orales präparat mit kontrollierter freisetzung |
| ES2531215T3 (es) * | 2006-01-27 | 2015-03-11 | Aptalis Pharmatech Inc | Sistemas de administración de fármacos que comprenden un agente de bloqueo selectivo de la serotonina 5-HT3 débilmente básico y ácidos orgánicos |
| CA2640382C (en) * | 2006-01-27 | 2015-12-29 | Eurand, Inc | Drug delivery systems comprising weakly basic drugs and organic acids |
| US7731604B2 (en) * | 2006-10-31 | 2010-06-08 | Taylor Made Golf Company, Inc. | Golf club iron head |
| EP1920785A1 (en) * | 2006-11-07 | 2008-05-14 | Boehringer Ingelheim Vetmedica Gmbh | Liquid preparation comprising a complex of pimobendan and cyclodextrin |
| UA97813C2 (uk) * | 2006-12-05 | 2012-03-26 | Янссен Фармацевтика Н.В. | Фумаратна сіль (альфа s, бета r)-6-бром-альфа-[2-(диметиламіно)етил]-2-метоксі-альфа-1-нафталеніл-бета-феніл-3-хінолінетанолу |
| US8133506B2 (en) * | 2008-03-12 | 2012-03-13 | Aptalis Pharmatech, Inc. | Drug delivery systems comprising weakly basic drugs and organic acids |
| WO2010060874A1 (en) | 2008-11-25 | 2010-06-03 | Boehringer Ingelheim Vetmedica Gmbh | Phosphodiesterase type iii (pde iii) inhibitors or ca2+-sensitizing agents for the treatment of hypertrophic cardiomyopathy |
| US20110003005A1 (en) * | 2009-07-06 | 2011-01-06 | Gopi Venkatesh | Methods of Treating PDNV and PONV with Extended Release Ondansetron Compositions |
| ES2924478T3 (es) | 2012-03-15 | 2022-10-07 | Boehringer Ingelheim Vetmedica Gmbh | Formulación de comprimidos farmacéuticos para el sector médico veterinario, método de producción y uso de los mismos |
| EP2898886B1 (en) | 2012-09-19 | 2017-02-15 | Taiho Pharmaceutical Co., Ltd. | Pharmaceutical composition for oral administration with improved elution and/or absorbency |
| JP6272475B2 (ja) | 2013-07-19 | 2018-01-31 | ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハーＢｏｅｈｒｉｎｇｅｒ Ｉｎｇｅｌｈｅｉｍ Ｖｅｔｍｅｄｉｃａ ＧｍｂＨ | 防腐エーテル化シクロデキストリン誘導体含有液体水性医薬組成物 |
| CN110721164B (zh) | 2013-12-04 | 2024-09-17 | 勃林格殷格翰动物保健有限公司 | 匹莫苯的改善的药物组合物 |
| JP6525897B2 (ja) * | 2016-01-21 | 2019-06-05 | 日清オイリオグループ株式会社 | タブレットの硬度調整剤 |
| US10537570B2 (en) | 2016-04-06 | 2020-01-21 | Boehringer Ingelheim Vetmedica Gmbh | Use of pimobendan for the reduction of heart size and/or the delay of onset of clinical symptoms in patients with asymptomatic heart failure due to mitral valve disease |
| CN109942445A (zh) * | 2019-02-26 | 2019-06-28 | 山东瑞弘生物科技有限公司 | 甜菜碱盐酸盐合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322755A (en) | 1964-03-10 | 1967-05-30 | Boehringer Sohn Ingelheim | Basic-substituted 1, 2, 3, 4-tetrahydropyrimido [5, 4-d]-pyrimidines |
| DD146547A5 (de) * | 1978-07-15 | 1981-02-18 | Boehringer Sohn Ingelheim | Arzneimittel-retardform mit unloeslichen poroesen diffusionshuellen |
| EP0019586A1 (de) * | 1979-05-11 | 1980-11-26 | Ciba-Geigy Ag | Neue antithrombotische Kombinationspräparate |
| DE2931573A1 (de) * | 1979-08-03 | 1981-02-26 | Thomae Gmbh Dr K | Mittel zur bekaempfung des wachstums von krebszellen und dessen herstellung |
| DE3000979A1 (de) * | 1980-01-12 | 1981-07-23 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue dipyridamol-retardformen und verfahren zu ihrer herstellung |
| DE3124090A1 (de) * | 1981-06-19 | 1983-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue orale dipyridamolformen |
| DE3126703A1 (de) * | 1981-07-07 | 1983-01-27 | Dr. Karl Thomae Gmbh, 7950 Biberach | Bromhexin-retardform und verfahren zu ihrer herstellung |
| DE3237575A1 (de) * | 1982-10-09 | 1984-04-12 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue orale mopidamolformen |
-
1982
- 1982-10-09 DE DE19823237575 patent/DE3237575A1/de not_active Withdrawn
-
1983
- 1983-09-24 AT AT83109510T patent/ATE21481T1/de not_active IP Right Cessation
- 1983-09-24 EP EP83109510A patent/EP0108898B1/de not_active Expired
- 1983-09-24 DE DE8383109510T patent/DE3365465D1/de not_active Expired
- 1983-10-05 FI FI833605A patent/FI79650C/fi not_active IP Right Cessation
- 1983-10-06 DK DK460683A patent/DK158541C/da not_active IP Right Cessation
- 1983-10-06 NO NO833638A patent/NO833638L/no unknown
- 1983-10-07 US US06/539,998 patent/US4596705A/en not_active Expired - Lifetime
- 1983-10-07 IE IE2358/83A patent/IE56058B1/en not_active IP Right Cessation
- 1983-10-07 GB GB08326877A patent/GB2128088B/en not_active Expired
- 1983-10-07 NZ NZ205894A patent/NZ205894A/en unknown
- 1983-10-07 GR GR72641A patent/GR79015B/el unknown
- 1983-10-07 ES ES526331A patent/ES8500743A1/es not_active Expired
- 1983-10-07 IL IL69930A patent/IL69930A/xx not_active IP Right Cessation
- 1983-10-07 PT PT77467A patent/PT77467B/pt not_active IP Right Cessation
- 1983-10-07 ZA ZA837499A patent/ZA837499B/xx unknown
- 1983-10-07 AU AU19985/83A patent/AU560251B2/en not_active Ceased
- 1983-10-07 JP JP58188283A patent/JPH07558B2/ja not_active Expired - Lifetime
- 1983-10-07 CA CA000438670A patent/CA1228546A/en not_active Expired
-
1985
- 1985-09-03 US US06/772,166 patent/US4650664A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4596705A (en) * | 1982-10-09 | 1986-06-24 | Dr. Karl Thomae Gmbh | Oral mopidamol preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ205894A (en) | 1986-08-08 |
| GB2128088B (en) | 1986-04-30 |
| DK460683A (da) | 1984-04-10 |
| EP0108898A1 (de) | 1984-05-23 |
| IL69930A0 (en) | 1984-01-31 |
| NO833638L (no) | 1984-04-10 |
| US4596705A (en) | 1986-06-24 |
| CA1228546A (en) | 1987-10-27 |
| EP0108898B1 (de) | 1986-08-20 |
| ATE21481T1 (de) | 1986-09-15 |
| ZA837499B (en) | 1985-06-26 |
| GR79015B (enExample) | 1984-10-02 |
| JPH07558B2 (ja) | 1995-01-11 |
| IE56058B1 (en) | 1991-04-10 |
| FI833605A0 (fi) | 1983-10-05 |
| GB2128088A (en) | 1984-04-26 |
| FI833605L (fi) | 1984-04-10 |
| IL69930A (en) | 1986-08-31 |
| DK460683D0 (da) | 1983-10-06 |
| AU560251B2 (en) | 1987-04-02 |
| PT77467B (de) | 1986-05-07 |
| FI79650C (fi) | 1990-02-12 |
| DE3365465D1 (en) | 1986-09-25 |
| FI79650B (fi) | 1989-10-31 |
| US4650664A (en) | 1987-03-17 |
| GB8326877D0 (en) | 1983-11-09 |
| PT77467A (de) | 1983-11-01 |
| DK158541B (da) | 1990-06-05 |
| AU1998583A (en) | 1984-04-12 |
| ES526331A0 (es) | 1984-11-01 |
| IE832358L (en) | 1984-04-09 |
| ES8500743A1 (es) | 1984-11-01 |
| JPS5989615A (ja) | 1984-05-23 |
| DK158541C (da) | 1990-11-05 |
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| 8139 | Disposal/non-payment of the annual fee |