DD283375A5 - Verwendung des tromethamin-salzes von 1-methyl-beta-oxo-alpha-(phenylcarbamoyl);2-pyrrol-propionitril - Google Patents
Verwendung des tromethamin-salzes von 1-methyl-beta-oxo-alpha-(phenylcarbamoyl);2-pyrrol-propionitril Download PDFInfo
- Publication number
- DD283375A5 DD283375A5 DD88323311A DD32331188A DD283375A5 DD 283375 A5 DD283375 A5 DD 283375A5 DD 88323311 A DD88323311 A DD 88323311A DD 32331188 A DD32331188 A DD 32331188A DD 283375 A5 DD283375 A5 DD 283375A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methyl
- beta
- phenylcarbamoyl
- salt
- oxo
- Prior art date
Links
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 title claims abstract description 21
- -1 PHENYLCARBAMOYL Chemical class 0.000 title description 3
- HDSRPMNZJOKFPL-UHFFFAOYSA-N 3-(1h-pyrrol-2-yl)propanenitrile Chemical compound N#CCCC1=CC=CN1 HDSRPMNZJOKFPL-UHFFFAOYSA-N 0.000 title 1
- 229940124347 antiarthritic drug Drugs 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 3
- 229940079593 drug Drugs 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims description 17
- KBQUAIAGRLAZGP-UHFFFAOYSA-N Prinomide Chemical compound CN1C=CC=C1C(=O)C(C#N)C(=O)NC1=CC=CC=C1 KBQUAIAGRLAZGP-UHFFFAOYSA-N 0.000 claims description 11
- 230000005764 inhibitory process Effects 0.000 claims description 9
- 230000002917 arthritic effect Effects 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 229960000281 trometamol Drugs 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 230000035605 chemotaxis Effects 0.000 claims description 3
- 230000003448 neutrophilic effect Effects 0.000 claims description 2
- 230000002686 anti-diuretic effect Effects 0.000 claims 1
- 229940124538 antidiuretic agent Drugs 0.000 claims 1
- 239000003160 antidiuretic agent Substances 0.000 claims 1
- 229940124622 immune-modulator drug Drugs 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
- 230000002456 anti-arthritic effect Effects 0.000 abstract description 3
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 241000124008 Mammalia Species 0.000 description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 210000000845 cartilage Anatomy 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000008422 cartilage matrix degradation Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
- 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 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108090000145 Bacillolysin Proteins 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- YFCDLVPYFMHRQZ-UHFFFAOYSA-N N-Nitrosodiethanolamine Chemical compound OCCN(N=O)CCO YFCDLVPYFMHRQZ-UHFFFAOYSA-N 0.000 description 2
- 102000035092 Neutral proteases Human genes 0.000 description 2
- 108091005507 Neutral proteases Proteins 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000024932 T cell mediated immunity Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000003501 co-culture Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000002519 immonomodulatory effect Effects 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 210000005222 synovial tissue Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- IVLBXSITZYYBMY-UHFFFAOYSA-N 2-amino-1,1,2-trichloroethanol Chemical class ClC(C(O)(Cl)Cl)N IVLBXSITZYYBMY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 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 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 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 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 241000219061 Rheum Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 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
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 230000002434 immunopotentiative effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000000492 nasalseptum Anatomy 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 201000004595 synovitis Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 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 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by 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
- 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)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1987/003413 WO1989005798A1 (en) | 1987-12-18 | 1987-12-18 | TROMETHAMINE SALT OF 1-METHYL-beta-OXO-alpha-(PHENYLCARBAMOYL)-2-PYRROLEPROPIONITRILE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD283375A5 true DD283375A5 (de) | 1990-10-10 |
Family
ID=22202723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88323311A DD283375A5 (de) | 1987-12-18 | 1988-12-16 | Verwendung des tromethamin-salzes von 1-methyl-beta-oxo-alpha-(phenylcarbamoyl);2-pyrrol-propionitril |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4977181A (es) |
| JP (1) | JPH02502534A (es) |
| KR (1) | KR890009868A (es) |
| AT (1) | AT390437B (es) |
| AU (1) | AU3596889A (es) |
| DD (1) | DD283375A5 (es) |
| DE (1) | DE3842250A1 (es) |
| DK (1) | DK704188A (es) |
| ES (1) | ES2012578A6 (es) |
| FI (1) | FI885828L (es) |
| FR (1) | FR2624856A1 (es) |
| GB (1) | GB2211187A (es) |
| HU (1) | HU199788B (es) |
| IL (1) | IL88654A0 (es) |
| IT (1) | IT1235336B (es) |
| LU (1) | LU87406A1 (es) |
| NL (1) | NL8803092A (es) |
| NO (1) | NO885576L (es) |
| PT (1) | PT88104A (es) |
| WO (1) | WO1989005798A1 (es) |
| YU (1) | YU227788A (es) |
| ZA (1) | ZA889355B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02502534A (ja) * | 1987-12-18 | 1990-08-16 | チバ‐ガイギー アクチェンゲゼルシャフト | 1‐メチル‐β‐オキソ‐α‐(フェニルカルバモイル)‐2‐ピロールプロピオニトリルのトロメタミン塩 |
| ES2058024B1 (es) * | 1992-11-10 | 1995-05-01 | Menarini Lab | Nuevo derivado arilpropionico, procedimiento de fabricacion del mismo y su utilizacion como analgesico. |
| US5431717A (en) * | 1993-12-03 | 1995-07-11 | Geobiotics, Inc. | Method for rendering refractory sulfide ores more susceptible to biooxidation |
| US7008979B2 (en) | 2002-04-30 | 2006-03-07 | Hydromer, Inc. | Coating composition for multiple hydrophilic applications |
| KR100576332B1 (ko) | 2004-07-16 | 2006-05-03 | 강승우 | 신규한 글라이세리드 유도체 및 이를 포함하는 통증완화용조성물 |
| LT2854768T (lt) | 2012-05-30 | 2017-06-12 | Fresenius Kabi Oncology Limited | Pemetreksedo farmacinės kompozicijos |
| JP2023527698A (ja) * | 2020-05-20 | 2023-06-30 | エフ. ホフマン-ラ ロシュ アーゲー | 新規マロニトリル誘導体 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4028772A (en) * | 1971-04-02 | 1973-09-27 | Merck & Co., Inc | Chemical processes |
| GB1398072A (en) * | 1971-06-14 | 1975-06-18 | May & Baker Ltd | Cyclopentane derivatives |
| US4089969A (en) * | 1976-07-14 | 1978-05-16 | Syntex (U.S.A.) Inc. | 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof |
| DD151307A5 (de) * | 1979-06-11 | 1981-10-14 | Ciba Geigy Ag | Verfahren zur herstellung von alphacarbamoyl-pyrrol-propionitrilen |
| US4256759A (en) * | 1979-06-11 | 1981-03-17 | Ciba-Geigy Corporation | Alphacarbamoyl-pyrrolpropionitriles |
| HU185926B (en) * | 1979-09-27 | 1985-04-28 | Agostne Kahan | Process for preparing water soluble derivatives of non-steroid antiinflammatory compositions and pharmaceutical compositins containing such derivatives |
| US4644010A (en) * | 1982-09-28 | 1987-02-17 | Ciba-Geigy Corporation | Certain β-oxo-α-carbamoylpyrrolepropionitriles |
| JPH02502534A (ja) * | 1987-12-18 | 1990-08-16 | チバ‐ガイギー アクチェンゲゼルシャフト | 1‐メチル‐β‐オキソ‐α‐(フェニルカルバモイル)‐2‐ピロールプロピオニトリルのトロメタミン塩 |
-
1987
- 1987-12-18 JP JP63500815A patent/JPH02502534A/ja active Pending
- 1987-12-18 WO PCT/US1987/003413 patent/WO1989005798A1/en not_active Ceased
- 1987-12-18 US US07/424,297 patent/US4977181A/en not_active Expired - Fee Related
-
1988
- 1988-07-26 PT PT88104A patent/PT88104A/pt not_active Application Discontinuation
- 1988-12-11 IL IL88654A patent/IL88654A0/xx unknown
- 1988-12-14 ZA ZA889355A patent/ZA889355B/xx unknown
- 1988-12-14 GB GB8829136A patent/GB2211187A/en not_active Withdrawn
- 1988-12-14 LU LU87406A patent/LU87406A1/de unknown
- 1988-12-15 IT IT8848657A patent/IT1235336B/it active
- 1988-12-15 DE DE3842250A patent/DE3842250A1/de not_active Withdrawn
- 1988-12-15 NO NO88885576A patent/NO885576L/no unknown
- 1988-12-16 FI FI885828A patent/FI885828L/fi not_active Application Discontinuation
- 1988-12-16 NL NL8803092A patent/NL8803092A/nl not_active Application Discontinuation
- 1988-12-16 ES ES888803830A patent/ES2012578A6/es not_active Expired - Lifetime
- 1988-12-16 AT AT0307488A patent/AT390437B/de not_active IP Right Cessation
- 1988-12-16 DD DD88323311A patent/DD283375A5/de not_active IP Right Cessation
- 1988-12-16 DK DK704188A patent/DK704188A/da not_active Application Discontinuation
- 1988-12-16 KR KR1019880016763A patent/KR890009868A/ko not_active Withdrawn
- 1988-12-16 HU HU886477A patent/HU199788B/hu not_active IP Right Cessation
- 1988-12-16 FR FR8816638A patent/FR2624856A1/fr not_active Withdrawn
- 1988-12-16 YU YU02277/88A patent/YU227788A/xx unknown
-
1989
- 1989-03-21 AU AU35968/89A patent/AU3596889A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL88654A0 (en) | 1989-07-31 |
| FI885828A7 (fi) | 1989-06-19 |
| NO885576D0 (no) | 1988-12-15 |
| DK704188D0 (da) | 1988-12-16 |
| DK704188A (da) | 1989-06-19 |
| KR890009868A (ko) | 1989-08-04 |
| ATA307488A (de) | 1989-10-15 |
| IT8848657A0 (it) | 1988-12-15 |
| NL8803092A (nl) | 1989-07-17 |
| FI885828A0 (fi) | 1988-12-16 |
| WO1989005798A1 (en) | 1989-06-29 |
| LU87406A1 (de) | 1990-02-28 |
| FR2624856A1 (en) | 1989-06-23 |
| HUT48582A (en) | 1989-06-28 |
| GB2211187A (en) | 1989-06-28 |
| US4977181A (en) | 1990-12-11 |
| ZA889355B (en) | 1989-10-25 |
| ES2012578A6 (es) | 1990-04-01 |
| GB8829136D0 (en) | 1989-01-25 |
| NO885576L (no) | 1989-06-19 |
| AT390437B (de) | 1990-05-10 |
| FI885828L (fi) | 1989-06-19 |
| HU199788B (en) | 1990-03-28 |
| DE3842250A1 (de) | 1989-06-29 |
| IT1235336B (it) | 1992-06-30 |
| JPH02502534A (ja) | 1990-08-16 |
| YU227788A (en) | 1990-08-31 |
| PT88104A (pt) | 1989-09-14 |
| AU3596889A (en) | 1990-01-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2226340C2 (es) | ||
| DE2332878C2 (de) | Salze von Cephalosporinen mit Arginin und Lysin, ihre Herstellung und injizierbare pharmazeutische Zubereitungen | |
| DE2709820A1 (de) | Neue cysteinderivate | |
| DE2234651A1 (de) | Eckige klammer auf 1-(p-chlorbenzoyl)5-methoxy-2-methyl-3-indol eckige klammer zu acetoxyessigsaeure, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln | |
| DD283375A5 (de) | Verwendung des tromethamin-salzes von 1-methyl-beta-oxo-alpha-(phenylcarbamoyl);2-pyrrol-propionitril | |
| EP0576906A1 (de) | Neue Thienothiazinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Antiinflammatorium und Analgeticum | |
| EP0313935B1 (de) | Enolether von 6-Chlor-4-hydroxy-2-methyl-N-(2-pyridyl)-2H-thieno(2,3-e)-1,2-thiazin-3-carbonsäureamid-1,1-dioxid, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung | |
| DE1934392C3 (de) | Neue 2-Pyridylthioamide und Verfahren zu ihrer Herstellung | |
| DE2054142A1 (de) | Pyridinsulfonsauren | |
| DE2530515C2 (de) | 4- bzw. 7-Hydroxy-4,5,6,7-tetrahydrothieno-[3,2-c] bzw.[2,3-c] pyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittelzubereitungen | |
| DE2332733A1 (de) | Psychotherapeutisch wirksame 2-aminothiazolabkoemmlinge und diese enthaltende arzneimittel | |
| DE2535799C3 (de) | N'- [1 -(p-Chlorbenzoyl)-5-methoxy-2-methyl-3indolyl-acetoxy- alkyl] -N-(N-benzoyl- N'JS'-di-npropyl-DL-isoglutaminyloxy- alkyD-piperazine und diese enthaltene Entzündungen und Gelenksaffektionen hemmende Präparate | |
| DE2415064A1 (de) | N-arylsulfonylharnstoffderivate, sie enthaltende arzneimittel und ihre herstellung | |
| CH516593A (de) | Verfahren zur Herstellung von neuen Estern von a-Aminobenzyl-penicillin | |
| DE2410982C3 (de) | Arzneimitel mit Sedativ- und Tranquilizer-Wirkung | |
| DE2031360A1 (de) | Neue cyclische Verbindungen und Ver fahren zu ihrer Herstellung | |
| DE2360560A1 (de) | Neue sydnon-derivate | |
| DE2609574A1 (de) | Monosubstituiertes piperazinderivat, verfahren zu seiner herstellung und es enthaltende arzneimittel | |
| EP0049538A2 (de) | Verwendung von Thioharnstoffderivaten als Arzneimittel bei der Behandlung von Fettstoffwechselstörungen | |
| AT390254B (de) | Verfahren zur herstellung von neuen aminderivaten der 4-phenyl-4-oxo-2-butensaeure und von deren salzen | |
| AT394045B (de) | Neue sulfamoyl-thiophene, verfahren zu ihrer herstellung und ihre verwendung | |
| DE3149478A1 (de) | Imidazol-derivate | |
| AT345852B (de) | Verfahren zur herstellung neuer furylharnstoffe | |
| DE3700158A1 (de) | 4,5-di-(phenyl)-oxazol-2-propionsaeurederivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE2433681A1 (de) | Neue benzyloxysulfamide, deren salze, verfahren zur herstellung und pharmazeutische zusammensetzungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |