NL8006341A - Voor roentgenstralen amorfe, fysiologisch toelaatbare zuuradditiezouten van ergotalkaloiden en dihydroer- gotalkaloiden, werkwijze voor de bereiding en toepas- sing daarvan in de therapie. - Google Patents
Voor roentgenstralen amorfe, fysiologisch toelaatbare zuuradditiezouten van ergotalkaloiden en dihydroer- gotalkaloiden, werkwijze voor de bereiding en toepas- sing daarvan in de therapie. Download PDFInfo
- Publication number
- NL8006341A NL8006341A NL8006341A NL8006341A NL8006341A NL 8006341 A NL8006341 A NL 8006341A NL 8006341 A NL8006341 A NL 8006341A NL 8006341 A NL8006341 A NL 8006341A NL 8006341 A NL8006341 A NL 8006341A
- Authority
- NL
- Netherlands
- Prior art keywords
- amorphous
- acid addition
- rays
- addition salts
- alkaloids
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims description 50
- 229960003133 ergot alkaloid Drugs 0.000 claims description 24
- 229930013930 alkaloid Natural products 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 229960002032 dihydroergocryptine Drugs 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229960004943 ergotamine Drugs 0.000 claims description 8
- OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical class C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 claims description 8
- XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 claims description 8
- XWMMZDZUHSYSPU-UHFFFAOYSA-N Dihydroergosine Natural products C1=CC(C2CC(CN(C)C2C2)C(=O)NC3(C(=O)N4C(C(N5CCCC5C4(O)O3)=O)CC(C)C)C)=C3C2=CNC3=C1 XWMMZDZUHSYSPU-UHFFFAOYSA-N 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 229960004704 dihydroergotamine Drugs 0.000 claims description 6
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine Chemical class C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 4
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 206010003119 arrhythmia Diseases 0.000 claims description 4
- 210000000748 cardiovascular system Anatomy 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 210000005259 peripheral blood Anatomy 0.000 claims description 4
- 239000011886 peripheral blood Substances 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- PBUNVLRHZGSROC-VTIMJTGVSA-N dihydro-alpha-ergocryptine Chemical compound C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1 PBUNVLRHZGSROC-VTIMJTGVSA-N 0.000 claims description 3
- NQRDVLDEYJYWQR-SZGCSELGSA-N dihydroergovaline Chemical class C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C)=C3C2=CNC3=C1 NQRDVLDEYJYWQR-SZGCSELGSA-N 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 208000008384 ileus Diseases 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- LIMAOLZSWRJOMG-HJPBWRTMSA-N dihydroergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C(C)C)C1=CC=CC=C1 LIMAOLZSWRJOMG-HJPBWRTMSA-N 0.000 claims description 2
- 229960004318 dihydroergocristine Drugs 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 4
- 150000003797 alkaloid derivatives Chemical class 0.000 claims 2
- 230000001376 precipitating effect Effects 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 22
- QHZUABXEBRGBLP-LKWYKXIFSA-N (6aR,9R,10aR)-N-[(2R,4R,9aS,9bR)-4-benzyl-9b-hydroxy-3,5-dioxo-2-propan-2-yl-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR,9R,10aR)-N-[(2R,4R,9aS,9bR)-9b-hydroxy-3,5-dioxo-2,4-di(propan-2-yl)-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR,10aR)-N-[(2S,4S,9bS)-9b-hydroxy-4-(2-methylpropyl)-3,5-dioxo-2-propan-2-yl-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)C4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2CC(CN(C)[C@@H]2C2)C(=O)N[C@@]3(C(=O)C4[C@@H](C(N5CCCC5[C@@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(C21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 QHZUABXEBRGBLP-LKWYKXIFSA-N 0.000 description 16
- 239000000945 filler Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VCCNKWWXYVWTLT-CYZBKYQRSA-N 7-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one Chemical compound C1=C(O)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 VCCNKWWXYVWTLT-CYZBKYQRSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 10
- 229960001903 ergotamine tartrate Drugs 0.000 description 10
- ADYPXRFPBQGGAH-UMYZUSPBSA-N dihydroergotamine mesylate Chemical compound CS(O)(=O)=O.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)C1=CC=CC=C1 ADYPXRFPBQGGAH-UMYZUSPBSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 5
- 229960001948 caffeine Drugs 0.000 description 5
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000968 intestinal effect Effects 0.000 description 4
- 239000007937 lozenge Substances 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BTLDVNBXSZELNL-DDLCCZDQSA-N ergotamine methansulfonate Chemical compound CS(O)(=O)=O.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C=3C=CC=C4NC=C(C=34)C2)=C1)C)C1=CC=CC=C1 BTLDVNBXSZELNL-DDLCCZDQSA-N 0.000 description 3
- 235000011389 fruit/vegetable juice Nutrition 0.000 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 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 description 1
- FXDJFTCVYTUARH-YZPGULDNSA-N 76f2r89o7x Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)C1=CC=CC=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)C1=CC=CC=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)C1=CC=CC=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)C1=CC=CC=C1 FXDJFTCVYTUARH-YZPGULDNSA-N 0.000 description 1
- RTAPDZBZLSXHQQ-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-2,6-dione Chemical class N1C(=O)NC(=O)C2=C1N=C(C)N2 RTAPDZBZLSXHQQ-UHFFFAOYSA-N 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010065508 Orthostatic hypertension Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- LGDAGYXJBDILKZ-UHFFFAOYSA-N [2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1$l^{6},2-benzothiazin-4-yl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 LGDAGYXJBDILKZ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 201000002676 cerebral atherosclerosis Diseases 0.000 description 1
- PBKVEOSEPXMKDN-LZHUFOCISA-N chembl2311030 Chemical class CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)CC)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 PBKVEOSEPXMKDN-LZHUFOCISA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- XWMMZDZUHSYSPU-ZADNKJPOSA-N dhesn Chemical compound C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C)=C3C2=CNC3=C1 XWMMZDZUHSYSPU-ZADNKJPOSA-N 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- QKMRPKVJXKAXHL-OLNIQZLRSA-N dihydroergonine Chemical compound C([C@H]1[C@]2(O)O3)CCN1C(=O)[C@H](C(C)C)N2C(=O)[C@]3(CC)NC(=O)[C@H]1CN(C)[C@H](CC=2C3=C4C=CC=C3NC=2)[C@@H]4C1 QKMRPKVJXKAXHL-OLNIQZLRSA-N 0.000 description 1
- 229960003643 dihydroergotamine tartrate Drugs 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU286779 | 1979-11-22 | ||
| YU2867/79A YU41681B (en) | 1979-11-22 | 1979-11-22 | Process for preparing x-ray amorhous physiologically tolerated acid additional salts of ergot alcaloids and dihydroergot alcaloids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8006341A true NL8006341A (nl) | 1981-06-16 |
Family
ID=25558910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8006341A NL8006341A (nl) | 1979-11-22 | 1980-11-20 | Voor roentgenstralen amorfe, fysiologisch toelaatbare zuuradditiezouten van ergotalkaloiden en dihydroer- gotalkaloiden, werkwijze voor de bereiding en toepas- sing daarvan in de therapie. |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS56164195A (https=) |
| BE (1) | BE886262A (https=) |
| DE (1) | DE3043832A1 (https=) |
| ES (1) | ES8205796A1 (https=) |
| FR (1) | FR2470133A1 (https=) |
| GB (1) | GB2063864B (https=) |
| LU (1) | LU82945A1 (https=) |
| NL (1) | NL8006341A (https=) |
| PT (1) | PT72078B (https=) |
| YU (1) | YU41681B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU87190A1 (fr) * | 1988-04-06 | 1989-11-14 | Wurth Paul Sa | Machine de percage de trous de coulee d'un four a cuve |
-
1979
- 1979-11-22 YU YU2867/79A patent/YU41681B/xx unknown
-
1980
- 1980-11-19 ES ES496969A patent/ES8205796A1/es not_active Expired
- 1980-11-19 LU LU82945A patent/LU82945A1/de unknown
- 1980-11-19 PT PT72078A patent/PT72078B/pt unknown
- 1980-11-19 GB GB8037133A patent/GB2063864B/en not_active Expired
- 1980-11-20 FR FR8024632A patent/FR2470133A1/fr active Granted
- 1980-11-20 NL NL8006341A patent/NL8006341A/nl not_active Application Discontinuation
- 1980-11-20 DE DE19803043832 patent/DE3043832A1/de not_active Ceased
- 1980-11-20 BE BE0/202868A patent/BE886262A/fr not_active IP Right Cessation
- 1980-11-21 JP JP16343880A patent/JPS56164195A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2470133A1 (fr) | 1981-05-29 |
| PT72078A (en) | 1980-12-01 |
| GB2063864A (en) | 1981-06-10 |
| GB2063864B (en) | 1983-07-20 |
| PT72078B (en) | 1981-09-29 |
| LU82945A1 (de) | 1981-03-26 |
| ES496969A0 (es) | 1982-08-01 |
| ES8205796A1 (es) | 1982-08-01 |
| YU286779A (en) | 1983-06-30 |
| JPS56164195A (en) | 1981-12-17 |
| DE3043832A1 (de) | 1981-09-17 |
| FR2470133B3 (https=) | 1982-09-03 |
| BE886262A (fr) | 1981-03-16 |
| YU41681B (en) | 1987-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6348456B1 (en) | Method of treating chemical dependency in mammals and a composition therefor | |
| CN101998957A (zh) | 取代的黄嘌呤衍生物 | |
| JPH0130834B2 (https=) | ||
| AU652951B2 (en) | Codeine salt of a substituted carboxylic acid, processes for the preparation thereof, its use and pharmaceutical compositions | |
| KR930001835B1 (ko) | 신규 히단토인(Hydantoin) 유도체의 제조방법 | |
| GB2038818A (en) | ???,???-Dihydropolyprenyl Alcohols and Pharmaceutical Compositions thereof | |
| IL102456A (en) | Medicinal preparations containing a history of xanthine for the treatment of secondary damage to nerve cells and functional disorders of closed skull-brain injury, some such new compounds | |
| US4085214A (en) | Stable pro-drug forms of theophylline | |
| HRP20090470A2 (hr) | Sol 3-benzil-2-methil-2.3.3.a.4.5.6.7,7a-octahidrobenzo[d]isoksazol-4-ona | |
| FI85142B (fi) | Foerfarande foer framstaellning av ergolinestrar. | |
| NL8006341A (nl) | Voor roentgenstralen amorfe, fysiologisch toelaatbare zuuradditiezouten van ergotalkaloiden en dihydroer- gotalkaloiden, werkwijze voor de bereiding en toepas- sing daarvan in de therapie. | |
| US3328424A (en) | 1-isopropylamino-2-hydroxy-3-(2'-isopropoxy-phenoxy)-propane and salts thereof | |
| US4338319A (en) | Method for the treatment of chronic obstructive airway or cardiac diseases | |
| US3275654A (en) | 1-isopropylamino-2-hydroxy-3-phenoxy-propanes and salts thereof | |
| TW209167B (https=) | ||
| US20040106671A1 (en) | Remedies for vesical hyperesthesia | |
| US4820837A (en) | 1-hydroxy-oxo-5H-pyrido(3,2-a)phenoxazine-3-carboxylic acid esters | |
| DE10137038A1 (de) | N-3,7 Substituted 1-Methylxanthine Derivates Displaying Inhibitory Activites on Type Five Phosphodiesterase | |
| JPS627167B2 (https=) | ||
| JPH062748B2 (ja) | 新規ヒダントイン誘導体及び該化合物を有効成分として含有する医薬組成物 | |
| JPS6245525A (ja) | 脂質低下剤 | |
| JPH04270222A (ja) | 脳機能改善剤 | |
| CH628321A5 (en) | Process for the preparation of derivatives of isobutyramide and medical composition containing these derivatives | |
| HU189660B (en) | Process for the separation of enantiomers of 2,3,3a,4,5,6-hexahydro-1h-indolo/3,2,1-de/ 1,5-naphthyridine and for preparing pharmaceutical compositions containing such compounds | |
| WO1998057645A1 (en) | Hepatic edema remedy |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |