FI58913C - Foerfarande foer framstaellning av farmaceutiskt anvaendbara tryptofansalt - Google Patents
Foerfarande foer framstaellning av farmaceutiskt anvaendbara tryptofansalt Download PDFInfo
- Publication number
- FI58913C FI58913C FI2520/74A FI252074A FI58913C FI 58913 C FI58913 C FI 58913C FI 2520/74 A FI2520/74 A FI 2520/74A FI 252074 A FI252074 A FI 252074A FI 58913 C FI58913 C FI 58913C
- Authority
- FI
- Finland
- Prior art keywords
- salt
- tryptophan
- water
- salts
- aqueous solution
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 19
- 229960004799 tryptophan Drugs 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 239000011575 calcium Substances 0.000 claims description 12
- QIVBCDIJIAJPQS-UHFFFAOYSA-N tryptophan Chemical compound C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- 239000002244 precipitate Substances 0.000 claims description 10
- -1 p-chlorobenzyloxy group Chemical group 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- IJWMYYIUFNJDKN-UHFFFAOYSA-N (4-chlorophenyl)methyl carbonochloridate Chemical compound ClC(=O)OCC1=CC=C(Cl)C=C1 IJWMYYIUFNJDKN-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 159000000000 sodium salts Chemical class 0.000 description 25
- 159000000007 calcium salts Chemical class 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 159000000003 magnesium salts Chemical class 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 230000001262 anti-secretory effect Effects 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000001663 anti-spastic effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- QJERBBQXOMUURJ-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CC(C(=O)O)NC(=O)C1=CC=C(Cl)C=C1 QJERBBQXOMUURJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- 239000012154 double-distilled water Substances 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 201000005917 gastric ulcer Diseases 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical group OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- ISNMKURUTRDPMG-UHFFFAOYSA-N 2-[(4-chlorophenyl)methoxycarbonylamino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CC(C(=O)O)NC(=O)OCC1=CC=C(Cl)C=C1 ISNMKURUTRDPMG-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 229940127007 Compound 39 Drugs 0.000 description 1
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical class C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 206010043275 Teratogenicity Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000008951 colonic inflammation Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 208000010643 digestive system disease Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000211 teratogenicity Toxicity 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—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
- C07D209/20—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 substituted additionally by nitrogen atoms, e.g. tryptophane
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39705173A | 1973-09-13 | 1973-09-13 | |
| US39705173 | 1973-09-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI252074A7 FI252074A7 (enExample) | 1975-03-14 |
| FI58913B FI58913B (fi) | 1981-01-30 |
| FI58913C true FI58913C (fi) | 1981-05-11 |
Family
ID=23569669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2520/74A FI58913C (fi) | 1973-09-13 | 1974-08-28 | Foerfarande foer framstaellning av farmaceutiskt anvaendbara tryptofansalt |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5231923B2 (enExample) |
| AT (1) | AT338258B (enExample) |
| AU (1) | AU468784B2 (enExample) |
| BE (1) | BE819650A (enExample) |
| CA (1) | CA1028332A (enExample) |
| CH (1) | CH614195A5 (enExample) |
| DE (1) | DE2442303A1 (enExample) |
| ES (1) | ES429988A1 (enExample) |
| FI (1) | FI58913C (enExample) |
| FR (1) | FR2243691B1 (enExample) |
| GB (1) | GB1433679A (enExample) |
| HK (1) | HK38779A (enExample) |
| HU (1) | HU168975B (enExample) |
| NL (1) | NL7411211A (enExample) |
| NO (1) | NO743260L (enExample) |
| SE (1) | SE399885B (enExample) |
| ZA (1) | ZA745448B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55130556U (enExample) * | 1979-03-09 | 1980-09-16 | ||
| WO2021240333A1 (en) * | 2020-05-24 | 2021-12-02 | Galimedix Therapeutics Inc. | Crystalline forms of solvates of tryptophan derivatives, compositions comprising them and uses thereof |
-
1974
- 1974-08-02 AU AU72870/74A patent/AU468784B2/en not_active Expired
- 1974-08-22 NL NL7411211A patent/NL7411211A/xx unknown
- 1974-08-23 GB GB3722474A patent/GB1433679A/en not_active Expired
- 1974-08-26 ZA ZA00745448A patent/ZA745448B/xx unknown
- 1974-08-28 FI FI2520/74A patent/FI58913C/fi active
- 1974-09-04 DE DE2442303A patent/DE2442303A1/de not_active Withdrawn
- 1974-09-06 BE BE148301A patent/BE819650A/xx not_active IP Right Cessation
- 1974-09-09 SE SE7411375A patent/SE399885B/xx unknown
- 1974-09-11 NO NO743260A patent/NO743260L/no unknown
- 1974-09-11 AT AT733774A patent/AT338258B/de not_active IP Right Cessation
- 1974-09-11 CH CH1234174A patent/CH614195A5/xx not_active IP Right Cessation
- 1974-09-12 JP JP49105439A patent/JPS5231923B2/ja not_active Expired
- 1974-09-12 HU HURO800A patent/HU168975B/hu unknown
- 1974-09-12 CA CA209,032A patent/CA1028332A/en not_active Expired
- 1974-09-12 ES ES429988A patent/ES429988A1/es not_active Expired
- 1974-09-12 FR FR7430928A patent/FR2243691B1/fr not_active Expired
-
1979
- 1979-06-14 HK HK387/79A patent/HK38779A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATA733774A (de) | 1976-12-15 |
| SE399885B (sv) | 1978-03-06 |
| CA1028332A (en) | 1978-03-21 |
| AU468784B2 (en) | 1976-01-22 |
| ZA745448B (en) | 1975-09-24 |
| AT338258B (de) | 1977-08-10 |
| SE7411375L (enExample) | 1975-03-14 |
| FI252074A7 (enExample) | 1975-03-14 |
| GB1433679A (en) | 1976-04-28 |
| NO743260L (enExample) | 1975-04-07 |
| FR2243691B1 (enExample) | 1978-02-03 |
| JPS5058065A (enExample) | 1975-05-20 |
| DE2442303A1 (de) | 1975-03-27 |
| FR2243691A1 (enExample) | 1975-04-11 |
| JPS5231923B2 (enExample) | 1977-08-18 |
| HU168975B (enExample) | 1976-08-28 |
| ES429988A1 (es) | 1976-09-16 |
| NL7411211A (nl) | 1975-03-17 |
| HK38779A (en) | 1979-06-22 |
| CH614195A5 (en) | 1979-11-15 |
| BE819650A (fr) | 1974-12-31 |
| FI58913B (fi) | 1981-01-30 |
| AU7287074A (en) | 1976-01-22 |
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