GB993754A - Improvements in or relating to novel thyromimetic compounds - Google Patents

Improvements in or relating to novel thyromimetic compounds

Info

Publication number
GB993754A
GB993754A GB45251/62A GB4525162A GB993754A GB 993754 A GB993754 A GB 993754A GB 45251/62 A GB45251/62 A GB 45251/62A GB 4525162 A GB4525162 A GB 4525162A GB 993754 A GB993754 A GB 993754A
Authority
GB
United Kingdom
Prior art keywords
acetyl
ethyl ester
compound
prepared
iodine
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
Application number
GB45251/62A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB993754A publication Critical patent/GB993754A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0993754/C2/1> in which R is a C2- 7 alkyl group or a phenyl group, and non-toxic, pharmaceutically acceptable salts thereof. The term "alkyl group" includes cycloalkyl groups. The compounds may be prepared by reacting a 3-R-4-methoxyphenol with N-acetyl-3,5-dinitro-tyrosine ethyl ester to prepare an N-acetyl-3-[41-(411 -methoxy-311-R-phenoxy) - 31,51 - dinitrophenyl] - analine ethyl ester, reducing the nitro groups of this compound to amino group and replacing these by iodine atoms by way of the tetra-azotized compound to give the corresponding N-acetyl-3 - [41 - (411 - methoxy - 311 - R - phenoxy) - 31,51-diiodophenyl]-analine ethyl ester (I) and treating the diiodo compound with a mixture of hydriodic and acetic acids. Alternatively, they may be prepared by reacting a bis-(3-R-4-methoxyphenyl)iodonium iodine (prepared from a 2-R-methoxybenzene and iodine trifluoro-acetate), with N-acetyl-3,5-diiode-tyrosine ethyl ester to produce (I) and then proceeding as above. Pharmaceutical compositions having thyromimetric activity comprise a compound of the invention together with a pharmaceutical carrier. The compositions may be formulated as capsules, tablets, lotions, ointments, aqueous suspensions or suppositories.
GB45251/62A 1961-12-05 1962-11-29 Improvements in or relating to novel thyromimetic compounds Expired GB993754A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US157249A US3149153A (en) 1961-12-05 1961-12-05 3'-substituted-3, 5-diiodothyronine and salts thereof

Publications (1)

Publication Number Publication Date
GB993754A true GB993754A (en) 1965-06-02

Family

ID=22562938

Family Applications (1)

Application Number Title Priority Date Filing Date
GB45251/62A Expired GB993754A (en) 1961-12-05 1962-11-29 Improvements in or relating to novel thyromimetic compounds

Country Status (3)

Country Link
US (1) US3149153A (en)
FR (1) FR2299M (en)
GB (1) GB993754A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8501372D0 (en) * 1985-01-18 1985-02-20 Smith Kline French Lab Chemical compounds
US5061798A (en) * 1985-01-18 1991-10-29 Smith Kline & French Laboratories, Ltd. Benzyl pyridyl and pyridazinyl compounds
US7504435B2 (en) * 2001-01-31 2009-03-17 The Arizona Board Of Regents On Behalf Of The University Of Arizona Method for stimulating weight loss and/or for lowering triglycerides in patients
US6534676B2 (en) * 2001-01-31 2003-03-18 The Arizona Board Of Regents On Behalf Of The University Of Arizona Method to treat chronic heart failure and/or elevated cholesterol levels using 3,5-diiodothyropropionic acid and method to prepare same
US9428444B2 (en) 2013-07-24 2016-08-30 Azico Biophore India Private Limited Process for the preparation of levothyroxine sodium

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2970165A (en) * 1957-10-01 1961-01-31 Warner Lambert Pharmaceutical Sulfate compounds

Also Published As

Publication number Publication date
US3149153A (en) 1964-09-15
FR2299M (en) 1964-01-27

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