GB1112874A - Esters of ª-alkyl thyronine derivatives and method of preparing these compounds - Google Patents
Esters of ª-alkyl thyronine derivatives and method of preparing these compoundsInfo
- Publication number
- GB1112874A GB1112874A GB43633/66A GB4363366A GB1112874A GB 1112874 A GB1112874 A GB 1112874A GB 43633/66 A GB43633/66 A GB 43633/66A GB 4363366 A GB4363366 A GB 4363366A GB 1112874 A GB1112874 A GB 1112874A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- iodo
- formula
- thyronine
- ethyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title abstract 11
- 150000002148 esters Chemical class 0.000 title abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 8
- HUSVOOUYGVGJGG-INIZCTEOSA-N (2s)-2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]-2-methylpropanoic acid Chemical compound IC1=CC(C[C@@](N)(C)C(O)=O)=CC(I)=C1OC1=CC=C(O)C=C1 HUSVOOUYGVGJGG-INIZCTEOSA-N 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 229940091173 hydantoin Drugs 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 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 abstract 1
- OCAZOCCWHWCEPV-KRWDZBQOSA-N (2s)-2-formamido-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]-2-methylpropanoic acid Chemical compound IC1=CC(C[C@](C)(NC=O)C(O)=O)=CC(I)=C1OC1=CC=C(O)C=C1 OCAZOCCWHWCEPV-KRWDZBQOSA-N 0.000 abstract 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 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- HRAXGVJSADRJIA-UHFFFAOYSA-N 5-ethyl-5-[(4-hydroxy-3,5-dinitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound C=1C([N+]([O-])=O)=C(O)C([N+]([O-])=O)=CC=1CC1(CC)NC(=O)NC1=O HRAXGVJSADRJIA-UHFFFAOYSA-N 0.000 abstract 1
- ZTBOBXARFVAOAG-UHFFFAOYSA-N 5-ethyl-5-[(4-hydroxyphenyl)methyl]imidazolidine-2,4-dione Chemical compound C=1C=C(O)C=CC=1CC1(CC)NC(=O)NC1=O ZTBOBXARFVAOAG-UHFFFAOYSA-N 0.000 abstract 1
- IWGAWBQHEVRJFX-UHFFFAOYSA-N 5-ethyl-5-[(4-methoxyphenyl)methyl]imidazolidine-2,4-dione Chemical compound C=1C=C(OC)C=CC=1CC1(CC)NC(=O)NC1=O IWGAWBQHEVRJFX-UHFFFAOYSA-N 0.000 abstract 1
- 238000007167 Hofmann rearrangement reaction Methods 0.000 abstract 1
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 1
- CKNXBBLTSYQOEW-UHFFFAOYSA-N [K].CC1=CC=C(S(=O)(=O)NI)C=C1 Chemical compound [K].CC1=CC=C(S(=O)(=O)NI)C=C1 CKNXBBLTSYQOEW-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- OMCWXFSQPKBREP-UHFFFAOYSA-N acetic acid;hydroiodide Chemical compound I.CC(O)=O OMCWXFSQPKBREP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- -1 hydroxyphenoxy compound Chemical class 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000026045 iodination Effects 0.000 abstract 1
- 238000006192 iodination reaction Methods 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
Classifications
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0037070 | 1965-10-07 | ||
| DE19651493567 DE1493567C3 (de) | 1965-10-07 | 1965-10-07 | Ester von alpha-Alkylthyroxinderivaten und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1112874A true GB1112874A (en) | 1968-05-08 |
Family
ID=31947311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43633/66A Expired GB1112874A (en) | 1965-10-07 | 1966-09-29 | Esters of ª-alkyl thyronine derivatives and method of preparing these compounds |
Country Status (15)
-
1966
- 1966-09-22 FI FI662493A patent/FI45188C/fi active
- 1966-09-23 IL IL26568A patent/IL26568A/xx unknown
- 1966-09-26 AT AT01111/68A patent/AT282081B/de active
- 1966-09-26 AT AT108968A patent/AT275750B/de active
- 1966-09-26 AT AT01113/68A patent/AT277481B/de active
- 1966-09-26 AT AT901566A patent/AT270090B/de active
- 1966-09-29 GB GB43633/66A patent/GB1112874A/en not_active Expired
- 1966-10-03 YU YU1863/66A patent/YU34028B/xx unknown
- 1966-10-04 OA OA52616A patent/OA02150A/xx unknown
- 1966-10-05 NO NO165017A patent/NO119317B/no unknown
- 1966-10-05 CH CH1433666A patent/CH471064A/de not_active IP Right Cessation
- 1966-10-05 SU SU1105855A patent/SU374817A3/ru active
- 1966-10-06 DK DK518966AA patent/DK127383B/da unknown
- 1966-10-06 SE SE13497/66A patent/SE345259B/xx unknown
- 1966-10-07 BE BE687980D patent/BE687980A/xx unknown
- 1966-10-07 BR BR183492/66A patent/BR6683492D0/pt unknown
- 1966-10-07 FR FR79226A patent/FR1496285A/fr not_active Expired
- 1966-10-07 NL NL666614150A patent/NL147133B/xx unknown
-
1968
- 1968-09-26 AT AT111268A patent/AT287927B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT275750B (de) | 1969-11-10 |
| AT282081B (de) | 1970-06-10 |
| NL6614150A (enrdf_load_stackoverflow) | 1967-04-10 |
| NL147133B (nl) | 1975-09-15 |
| AT287927B (de) | 1971-02-10 |
| AT270090B (de) | 1969-04-10 |
| FI45188B (enrdf_load_stackoverflow) | 1971-12-31 |
| BR6683492D0 (pt) | 1973-12-04 |
| OA02150A (fr) | 1970-05-05 |
| SE345259B (enrdf_load_stackoverflow) | 1972-05-23 |
| BE687980A (enrdf_load_stackoverflow) | 1967-04-07 |
| FI45188C (fi) | 1972-04-10 |
| IL26568A (en) | 1971-02-25 |
| NO119317B (enrdf_load_stackoverflow) | 1970-05-04 |
| FR1496285A (fr) | 1967-09-29 |
| YU34028B (en) | 1978-10-31 |
| SU374817A3 (enrdf_load_stackoverflow) | 1973-03-20 |
| DK127383B (da) | 1973-10-29 |
| AT277481B (de) | 1969-12-29 |
| YU186366A (en) | 1978-05-15 |
| CH471064A (de) | 1969-04-15 |
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