DE2254018A1 - Neue pharmazeutische praeparate - Google Patents
Neue pharmazeutische praeparateInfo
- Publication number
- DE2254018A1 DE2254018A1 DE2254018A DE2254018A DE2254018A1 DE 2254018 A1 DE2254018 A1 DE 2254018A1 DE 2254018 A DE2254018 A DE 2254018A DE 2254018 A DE2254018 A DE 2254018A DE 2254018 A1 DE2254018 A1 DE 2254018A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amino
- pharmaceutical preparation
- preparation according
- methyl
- 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.)
- Pending
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 30
- 150000003839 salts Chemical class 0.000 claims description 36
- DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical compound CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-UHFFFAOYSA-N 0.000 claims description 30
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000001413 amino acids Chemical class 0.000 claims description 21
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 claims description 20
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 claims description 20
- -1 diethylthiocarbamoyl Chemical group 0.000 claims description 17
- 229940122439 Hydroxylase inhibitor Drugs 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 231100000252 nontoxic Toxicity 0.000 claims description 7
- 230000003000 nontoxic effect Effects 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 159000000007 calcium salts Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- BOHRWPVFCVAKKS-UHFFFAOYSA-N 5-pentylpyridine-2-carboxylic acid Chemical compound CCCCCC1=CC=C(C(O)=O)N=C1 BOHRWPVFCVAKKS-UHFFFAOYSA-N 0.000 claims description 2
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 4
- 239000000463 material Substances 0.000 claims 4
- 239000003513 alkali Substances 0.000 claims 2
- YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 claims 1
- GSYSNSTWMPZEQK-UHFFFAOYSA-N 5-butyl-2-methylpyridine Chemical compound CCCCC1=CC=C(C)N=C1 GSYSNSTWMPZEQK-UHFFFAOYSA-N 0.000 claims 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 1
- 229940081066 picolinic acid Drugs 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 11
- 206010020772 Hypertension Diseases 0.000 description 8
- 239000003826 tablet Substances 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 5
- 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 4
- 239000002253 acid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229940100445 wheat starch Drugs 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XMRLUNALKLDUPT-UHFFFAOYSA-L calcium;5-butylpyridine-2-carboxylate Chemical compound [Ca+2].CCCCC1=CC=C(C([O-])=O)N=C1.CCCCC1=CC=C(C([O-])=O)N=C1 XMRLUNALKLDUPT-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CJCSPKMFHVPWAR-UHFFFAOYSA-N 3-Hydroxy-alpha-methyl-DL-tyrosine Chemical compound OC(=O)C(N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- NHTGHBARYWONDQ-UHFFFAOYSA-N (+-)-α-methyl-tyrosine Chemical compound OC(=O)C(N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-UHFFFAOYSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- UYRNFBHAWUOWGM-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(O)C(O)=C1 UYRNFBHAWUOWGM-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- DKXULEFCEORBJK-UHFFFAOYSA-N magnesium;octadecanoic acid Chemical compound [Mg].CCCCCCCCCCCCCCCCCC(O)=O DKXULEFCEORBJK-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1637771 | 1971-11-11 | ||
| CH1354572 | 1972-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2254018A1 true DE2254018A1 (de) | 1973-05-30 |
Family
ID=25712489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2254018A Pending DE2254018A1 (de) | 1971-11-11 | 1972-11-04 | Neue pharmazeutische praeparate |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3883656A (enrdf_load_stackoverflow) |
| AU (1) | AU4864272A (enrdf_load_stackoverflow) |
| BE (1) | BE791253A (enrdf_load_stackoverflow) |
| DE (1) | DE2254018A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2159413B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1405949A (enrdf_load_stackoverflow) |
| IE (1) | IE36780B1 (enrdf_load_stackoverflow) |
| IL (1) | IL40597A (enrdf_load_stackoverflow) |
| NL (1) | NL7214607A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4389415A (en) * | 1978-01-24 | 1983-06-21 | Merck & Co., Inc. | Method of treating hypertension |
| US4321264A (en) * | 1980-04-14 | 1982-03-23 | Merck & Co., Inc. | α-methyldopa compositions |
| EP0374764B1 (en) * | 1988-12-19 | 2001-04-04 | Nec Corporation | Data transfer apparatus |
-
1972
- 1972-10-17 IE IE1403/72A patent/IE36780B1/xx unknown
- 1972-10-17 IL IL40597A patent/IL40597A/en unknown
- 1972-10-27 NL NL7214607A patent/NL7214607A/xx unknown
- 1972-10-30 US US302156A patent/US3883656A/en not_active Expired - Lifetime
- 1972-11-04 DE DE2254018A patent/DE2254018A1/de active Pending
- 1972-11-08 GB GB5151672A patent/GB1405949A/en not_active Expired
- 1972-11-09 FR FR7239713A patent/FR2159413B1/fr not_active Expired
- 1972-11-09 AU AU48642/72A patent/AU4864272A/en not_active Expired
- 1972-11-10 BE BE791253D patent/BE791253A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE791253A (fr) | 1973-05-10 |
| NL7214607A (enrdf_load_stackoverflow) | 1973-05-15 |
| IE36780B1 (en) | 1977-02-16 |
| US3883656A (en) | 1975-05-13 |
| IE36780L (en) | 1973-05-11 |
| AU472689B2 (enrdf_load_stackoverflow) | 1976-06-03 |
| FR2159413B1 (enrdf_load_stackoverflow) | 1975-08-08 |
| FR2159413A1 (enrdf_load_stackoverflow) | 1973-06-22 |
| GB1405949A (en) | 1975-09-10 |
| IL40597A (en) | 1976-06-30 |
| AU4864272A (en) | 1974-05-09 |
| IL40597A0 (en) | 1972-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69916922T2 (de) | Ibuprofenhaltige Arzneizubereitung | |
| DE60026144T2 (de) | Benzamidformulierung mit histon-deacetylase-inhibitoraktivität | |
| DE69623634T2 (de) | Pharmazeutische zusammensetzung von l-dopa ethyl ester | |
| DE2043933C3 (de) | N-(ß-Naphthylaminomethyl)-aminocarbonsäuren sowie diese enthaltende Arzneimittel | |
| DE1795792A1 (de) | Die serumlipoidkonzentration vermindernde arzneimittel | |
| DE2945790A1 (de) | Neutrales kristallines salz einer basischen l-aminosaeure mit l-apfelsaeure und verfahren zu dessen herstellung | |
| DE3785401T2 (de) | Verwendung von Phenylethanolaminen zur Herstellung von Arzneimitteln, wirksam für gastrointestinale Beschwerden. | |
| DE1915798C3 (de) | Antacidum-Präparat in Form einer wäßrigen Suspension | |
| DE60024995T2 (de) | Synergistische kombination: gabapentin und pregabalin | |
| DE2726392A1 (de) | Mittel zur bekaempfung der venoesen thrombose | |
| DE3730277C2 (de) | Salz einer Organogermaniumverbindung und dessen Verwendung | |
| DE2254018A1 (de) | Neue pharmazeutische praeparate | |
| DD209735A5 (de) | Verfahren zur herstellung eines neuen arzneimittelpraeparates | |
| DE2059620C3 (de) | 2-(alpha-(p-Chlorphenoxy)-isobutyryl)aminoäthansulfonsäure, ihre physiologisch verträglichen Salze, Verfahren zur Herstellung dieser Verbindungen und pharmakologisch wirksame Zubereitungen derselben | |
| DE3310584C2 (enrdf_load_stackoverflow) | ||
| DE2460756A1 (de) | Arzneimittel zur verbesserung der endogenen prostaglandinbildung sowie neue n-(pyridylalkyl)-benzamide, die als wirkstoffe fuer die arzneimittel geeignet sind, und verfahren zu deren herstellung | |
| DE2236876A1 (de) | N-substituierte aminosaeuren mit wirkungen gegen viren, entzuendungen und/oder tumoren | |
| EP0308665B1 (de) | Salze der 5-Aminosalicylsäure und sie enthaltende Arzneimittelzubereitungen | |
| DE2615129C3 (de) | Tripeptide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen | |
| DE2131680A1 (de) | 3,4,5-Trialkoxybenzoylaminoalkancarbonsaeure-Verbindungen und ihre Salze sowie Arzneipraeparate | |
| EP0253293B1 (de) | Neue Guanidiniumasparaginate | |
| DE60311134T2 (de) | Oromukosale formulierung und herstellungsverfahren dafür | |
| DE2131616A1 (de) | Pharmazeutisches Praeparat | |
| DE1667903B2 (de) | Verwendung von Cysteinderivaten zur Herstellung von per oral verabreichbaren Mitteln zur Bekämpfung der Seborrhoe | |
| DE1117571B (de) | Verfahren zur Herstellung von choleretisch wirksamer ª-[1-Hydroxy-4-phenylcyclohexyl-(1)]-buttersaeure, deren AEthylester bzw. deren Salzen |