DE1793776A1 - Alpha-alkylthyroxine und verfahren zu ihrer herstellung - Google Patents
Alpha-alkylthyroxine und verfahren zu ihrer herstellungInfo
- Publication number
- DE1793776A1 DE1793776A1 DE19651793776 DE1793776A DE1793776A1 DE 1793776 A1 DE1793776 A1 DE 1793776A1 DE 19651793776 DE19651793776 DE 19651793776 DE 1793776 A DE1793776 A DE 1793776A DE 1793776 A1 DE1793776 A1 DE 1793776A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compound
- inorganic
- acids
- salts
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 10
- 150000007529 inorganic bases Chemical class 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- -1 DL-α-propyl-thyroxine Chemical compound 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000006193 diazotization reaction Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- HRNSODLWWQUGEP-UHFFFAOYSA-N 2-(ethylamino)-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid Chemical compound IC1=CC(CC(NCC)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 HRNSODLWWQUGEP-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 241000700159 Rattus Species 0.000 description 10
- 229940091173 hydantoin Drugs 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 230000037323 metabolic rate Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- XUIIKFGFIJCVMT-LBPRGKRZSA-N L-thyroxine Chemical compound IC1=CC(C[C@H]([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-LBPRGKRZSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229950008325 levothyroxine Drugs 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- 206010003211 Arteriosclerosis coronary artery Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 210000001685 thyroid gland Anatomy 0.000 description 2
- 239000005495 thyroid hormone Substances 0.000 description 2
- 229940036555 thyroid hormone Drugs 0.000 description 2
- CQRBELJPAZUIIW-KRWDZBQOSA-N (2S)-2-amino-2-[[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]methyl]butanoic acid Chemical compound C(C)[C@](N)(CC1=CC(=C(C(=C1)I)OC1=CC=C(C=C1)O)I)C(=O)O CQRBELJPAZUIIW-KRWDZBQOSA-N 0.000 description 1
- MSAGWOOSGXLSMK-SFHVURJKSA-N (2S)-2-amino-2-[[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]methyl]pentanoic acid Chemical compound C(CC)[C@](N)(CC1=CC(=C(C(=C1)I)OC1=CC=C(C=C1)O)I)C(=O)O MSAGWOOSGXLSMK-SFHVURJKSA-N 0.000 description 1
- DXBXFNKWRXAJIA-HNNXBMFYSA-N (2s)-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-2-(propylamino)propanoic acid Chemical compound IC1=CC(C[C@H](NCCC)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 DXBXFNKWRXAJIA-HNNXBMFYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- UDRKGPPMCPQZAX-KRWDZBQOSA-N CCCCCN[C@@H](CC(C=C1I)=CC(I)=C1OC(C=C1I)=CC(I)=C1O)C(O)=O Chemical compound CCCCCN[C@@H](CC(C=C1I)=CC(I)=C1OC(C=C1I)=CC(I)=C1O)C(O)=O UDRKGPPMCPQZAX-KRWDZBQOSA-N 0.000 description 1
- VOPRUZFKMHBDRJ-FQEVSTJZSA-N CCCCC[C@](CC(C=C1I)=CC(I)=C1OC(C=C1)=CC=C1O)(C(O)=O)N Chemical compound CCCCC[C@](CC(C=C1I)=CC(I)=C1OC(C=C1)=CC=C1O)(C(O)=O)N VOPRUZFKMHBDRJ-FQEVSTJZSA-N 0.000 description 1
- VLHNHKPLSLCPKO-UHFFFAOYSA-N COC1=CC=C(CCCCCCC(CCCCCCC(C=C2)=CC=C2OC)=O)C=C1 Chemical compound COC1=CC=C(CCCCCCC(CCCCCCC(C=C2)=CC=C2OC)=O)C=C1 VLHNHKPLSLCPKO-UHFFFAOYSA-N 0.000 description 1
- HRNSODLWWQUGEP-AWEZNQCLSA-N IC1=CC(C[C@H](NCC)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 Chemical compound IC1=CC(C[C@H](NCC)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 HRNSODLWWQUGEP-AWEZNQCLSA-N 0.000 description 1
- 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 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XRRYGMTXOYFERK-UHFFFAOYSA-N [I].[K].[I] Chemical compound [I].[K].[I] XRRYGMTXOYFERK-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 230000000651 anti-goitrogenic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- 230000001897 thyrotoxic effect Effects 0.000 description 1
- 229940034208 thyroxine Drugs 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19641493533 DE1493533C (de) | 1964-04-10 | 1964-04-10 | alpha Alkyl thyroxine und Verfahren zu ihrer Herstellung |
| DE19651793776 DE1793776A1 (de) | 1964-04-10 | 1965-03-11 | Alpha-alkylthyroxine und verfahren zu ihrer herstellung |
| DE19651493567 DE1493567C3 (de) | 1965-10-07 | 1965-10-07 | Ester von alpha-Alkylthyroxinderivaten und Verfahren zu ihrer Herstellung |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0032613 | 1964-04-10 | ||
| DE19651793776 DE1793776A1 (de) | 1964-04-10 | 1965-03-11 | Alpha-alkylthyroxine und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793776A1 true DE1793776A1 (de) | 1974-08-29 |
Family
ID=7020410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651793776 Pending DE1793776A1 (de) | 1964-04-10 | 1965-03-11 | Alpha-alkylthyroxine und verfahren zu ihrer herstellung |
Country Status (13)
-
1965
- 1965-03-08 AT AT203465A patent/AT268547B/de active
- 1965-03-08 AT AT372066A patent/AT268553B/de active
- 1965-03-08 AT AT371966A patent/AT268552B/de active
- 1965-03-11 DE DE19651793776 patent/DE1793776A1/de active Pending
- 1965-03-15 NL NL656503266A patent/NL142402B/xx unknown
- 1965-04-01 GB GB13872/65A patent/GB1100643A/en not_active Expired
- 1965-04-05 FI FI650814A patent/FI43439C/fi active
- 1965-04-07 CH CH480865A patent/CH469664A/de unknown
- 1965-04-08 BE BE662271A patent/BE662271A/xx unknown
- 1965-04-09 ES ES0311669A patent/ES311669A1/es not_active Expired
- 1965-04-09 FR FR1587317D patent/FR1587317A/fr not_active Expired
- 1965-04-09 OA OA51586A patent/OA01689A/xx unknown
- 1965-04-09 DK DK183165AA patent/DK123229B/da unknown
- 1965-04-09 BR BR168876/65A patent/BR6568876D0/pt unknown
- 1965-04-09 SE SE04627/65A patent/SE332994B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| OA01689A (fr) | 1969-12-15 |
| DK123229B (da) | 1972-05-29 |
| AT268553B (de) | 1969-02-10 |
| AT268552B (de) | 1969-02-10 |
| NL6503266A (enrdf_load_stackoverflow) | 1965-10-11 |
| ES311669A1 (es) | 1965-07-01 |
| CH469664A (de) | 1969-03-15 |
| AT268547B (de) | 1969-02-10 |
| BE662271A (enrdf_load_stackoverflow) | 1965-10-08 |
| FR1587317A (enrdf_load_stackoverflow) | 1970-03-20 |
| FI43439B (enrdf_load_stackoverflow) | 1970-12-31 |
| BR6568876D0 (pt) | 1973-08-07 |
| FI43439C (fi) | 1971-04-13 |
| GB1100643A (en) | 1968-01-24 |
| NL142402B (nl) | 1974-06-17 |
| SE332994B (enrdf_load_stackoverflow) | 1971-03-01 |
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