GB2005659A - Substituted alpha -Halomethyl Phenylalanines - Google Patents
Substituted alpha -Halomethyl PhenylalaninesInfo
- Publication number
- GB2005659A GB2005659A GB7827966A GB7827966A GB2005659A GB 2005659 A GB2005659 A GB 2005659A GB 7827966 A GB7827966 A GB 7827966A GB 7827966 A GB7827966 A GB 7827966A GB 2005659 A GB2005659 A GB 2005659A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- carbon atoms
- carbonyl
- alkyl
- phenylalanines
- 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.)
- Granted
Links
- 235000008729 phenylalanine Nutrition 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- -1 methylenedioxy Chemical group 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Peptides Or Proteins (AREA)
Abstract
Novel pharmaceutically useful compounds of the formula <IMAGE> and pharmaceutically acceptable salts and individual optical isomers thereof, wherein Y is -CH2F, -CHF2, -CH2Cl or -CHCl2; R1 is hydrogen, (C1-4alkyl)carbonyl, (C1-4alkoxy)carbonyl or -CO-CHNH2-R27 wherein R27 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R is hydroxy, alkoxy of 1 to 8 carbon atoms, -NR7R8 wherein R7 and R8 are the same or different and are each hydrogen or alkyl of 1 to 4 carbon atoms or -NH-CHR9-COOH wherein R9 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or p- hydroxybenzyl; and R2, R3, R4, R5 and R6 are various combinations of hydrogen, methyl, ethyl, tert-butyl, halogen, trifluoromethyl and OR10 wherein R10 is hydrogen, alkyl of 1 to 8 carbon atoms, (C1-6alkyl)carbonyl, benzoyl or phenyl (C1-6alkyl)-carbonyl or R3 and R4 together are methylenedioxy.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81424377A | 1977-07-11 | 1977-07-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2005659A true GB2005659A (en) | 1979-04-25 |
| GB2005659B GB2005659B (en) | 1982-02-17 |
Family
ID=25214519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7827966A Expired GB2005659B (en) | 1977-07-11 | 1978-06-27 | Halomethyl amino acids |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5484544A (en) |
| AU (1) | AU525684B2 (en) |
| BE (1) | BE868881A (en) |
| CH (1) | CH636846A5 (en) |
| DE (1) | DE2828738A1 (en) |
| DK (1) | DK309378A (en) |
| ES (3) | ES471595A1 (en) |
| FR (1) | FR2397391A1 (en) |
| GB (1) | GB2005659B (en) |
| IE (1) | IE46932B1 (en) |
| IL (1) | IL54913A0 (en) |
| IT (1) | IT1105534B (en) |
| NL (1) | NL7807454A (en) |
| NZ (1) | NZ187538A (en) |
| SE (1) | SE7807690L (en) |
| ZA (1) | ZA783273B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007600A1 (en) * | 1978-07-24 | 1980-02-06 | Merck & Co. Inc. | Alpha-difluoromethyl amino acids and pharmaceutical composition containing the same |
| EP0040150A1 (en) * | 1980-05-09 | 1981-11-18 | Merrell Toraude Et Compagnie | Fluoromethylated tyrosine methyl ester |
| JPS5777657A (en) * | 1980-08-23 | 1982-05-15 | Merrell Toraude & Co | Manufacture of aminonitrile derivative |
| CN113302176A (en) * | 2018-12-06 | 2021-08-24 | 先达生物科技公司 | Decarboxylase inhibitors for the treatment of parkinson's disease |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL59481A0 (en) * | 1977-07-11 | 1980-05-30 | Merrell Toraude & Co | -halomethyl amino acids |
| FR2450247A1 (en) * | 1979-02-28 | 1980-09-26 | Tamsir Ndike Wade | Alpha-amino-beta,beta-di:fluoro carboxylic acid ester(s) - prepd. by reaction of hydrofluoric acid with 2-substd. 3-carboxy-ester-1-azirine have potential use as antibacterials and CNS stimulants |
| IE49522B1 (en) * | 1979-04-26 | 1985-10-16 | Merrell Toraude & Co | Alpha-halomethylaminoacids |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3046300A (en) * | 1960-10-21 | 1962-07-24 | Merck & Co Inc | alpha-trifluoromethyloxyphenylalanines |
| NZ187377A (en) * | 1977-06-01 | 1981-05-15 | Merck & Co Inc | A-amino-a-substituted alkyl-a-fluoromethylacetic acids |
| IE47542B1 (en) * | 1977-06-01 | 1984-04-18 | Merck & Co Inc | Di-and tri-fluoromethyl amino acids and amines,compositions and processes for preparing said compounds |
-
1978
- 1978-06-07 ZA ZA00783273A patent/ZA783273B/en unknown
- 1978-06-08 IE IE1167/78A patent/IE46932B1/en not_active IP Right Cessation
- 1978-06-13 NZ NZ187538A patent/NZ187538A/en unknown
- 1978-06-15 IL IL7854913A patent/IL54913A0/en not_active IP Right Cessation
- 1978-06-21 AU AU37312/78A patent/AU525684B2/en not_active Expired
- 1978-06-27 GB GB7827966A patent/GB2005659B/en not_active Expired
- 1978-06-30 DE DE19782828738 patent/DE2828738A1/en not_active Withdrawn
- 1978-07-07 CH CH742978A patent/CH636846A5/en not_active IP Right Cessation
- 1978-07-08 JP JP8253178A patent/JPS5484544A/en active Granted
- 1978-07-10 SE SE7807690A patent/SE7807690L/en unknown
- 1978-07-10 FR FR7820516A patent/FR2397391A1/en active Granted
- 1978-07-10 ES ES471595A patent/ES471595A1/en not_active Expired
- 1978-07-10 DK DK783093A patent/DK309378A/en unknown
- 1978-07-10 IT IT50230/78A patent/IT1105534B/en active
- 1978-07-10 BE BE189190A patent/BE868881A/en not_active IP Right Cessation
- 1978-07-11 NL NL7807454A patent/NL7807454A/en not_active Application Discontinuation
-
1979
- 1979-03-12 ES ES478517A patent/ES478517A1/en not_active Expired
- 1979-03-12 ES ES478516A patent/ES478516A1/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0007600A1 (en) * | 1978-07-24 | 1980-02-06 | Merck & Co. Inc. | Alpha-difluoromethyl amino acids and pharmaceutical composition containing the same |
| EP0040150A1 (en) * | 1980-05-09 | 1981-11-18 | Merrell Toraude Et Compagnie | Fluoromethylated tyrosine methyl ester |
| JPS5777657A (en) * | 1980-08-23 | 1982-05-15 | Merrell Toraude & Co | Manufacture of aminonitrile derivative |
| CN113302176A (en) * | 2018-12-06 | 2021-08-24 | 先达生物科技公司 | Decarboxylase inhibitors for the treatment of parkinson's disease |
| EP3891122A4 (en) * | 2018-12-06 | 2022-10-05 | Senda Biosciences, Inc. | Decarboxylase inhibitors for treating parkinson's disease |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6326101B2 (en) | 1988-05-27 |
| IL54913A0 (en) | 1978-08-31 |
| NZ187538A (en) | 1982-08-17 |
| IT1105534B (en) | 1985-11-04 |
| ES478516A1 (en) | 1979-07-16 |
| IT7850230A0 (en) | 1978-07-10 |
| SE7807690L (en) | 1979-01-12 |
| NL7807454A (en) | 1979-01-15 |
| IE781167L (en) | 1979-01-11 |
| ES478517A1 (en) | 1979-07-16 |
| GB2005659B (en) | 1982-02-17 |
| AU525684B2 (en) | 1982-11-25 |
| DE2828738A1 (en) | 1979-02-01 |
| JPS5484544A (en) | 1979-07-05 |
| DK309378A (en) | 1979-01-12 |
| FR2397391B1 (en) | 1981-02-20 |
| ES471595A1 (en) | 1979-10-01 |
| FR2397391A1 (en) | 1979-02-09 |
| ZA783273B (en) | 1979-06-27 |
| BE868881A (en) | 1978-11-03 |
| AU3731278A (en) | 1980-01-03 |
| CH636846A5 (en) | 1983-06-30 |
| IE46932B1 (en) | 1983-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940627 |