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GB2001960A - Pharmaceutically Active alpha -Halomethyl Derivatives of alpha -Amino Acids - Google Patents

Pharmaceutically Active alpha -Halomethyl Derivatives of alpha -Amino Acids

Info

Publication number
GB2001960A
GB2001960A GB7827967A GB7827967A GB2001960A GB 2001960 A GB2001960 A GB 2001960A GB 7827967 A GB7827967 A GB 7827967A GB 7827967 A GB7827967 A GB 7827967A GB 2001960 A GB2001960 A GB 2001960A
Authority
GB
United Kingdom
Prior art keywords
alpha
hydrogen
carbon atoms
amino acids
pharmaceutically active
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
Application number
GB7827967A
Other versions
GB2001960B (en
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.)
Merrell Toraude et Cie
Original Assignee
Merrell Toraude et Cie
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 Merrell Toraude et Cie filed Critical Merrell Toraude et Cie
Publication of GB2001960A publication Critical patent/GB2001960A/en
Application granted granted Critical
Publication of GB2001960B publication Critical patent/GB2001960B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C07D223/08—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Urology & Nephrology (AREA)
  • Communicable Diseases (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Saccharide Compounds (AREA)

Abstract

The derivatives have the formulae <IMAGE> wherein Y is -CH2F, -CHF2, -CF2, -CH2Cl or -CHCl2; Z is beta -methylthioethyl, beta -thioethyl, beta -benzylthioethyl, S-(5'- desoxyadenosin- 5'-yl)-S-methyl- thioethyl, gamma -guanidinopropyl, or RaHN(CH2)n- wherein n is 3 or 4, or HN(CH2)n- wherein n is 3 or 4, or <IMAGE> wherein Y2 is -CH2F, -CHF2 or -CF3; Ra, if present, and Rb are the same or different and are each hydrogen, (C1-4alkyl)carbonyl, (C1-4alkoxy)carbonyl or -CO-CHNH2-R2 wherein R2 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and R1 is hydroxy, alkoxy of from 1 to 8 carbon atoms, -NR4R5 wherein R4 and R5 are the same or different and are each hydrogen or alkyl of 1 to 4 carbon atoms, or -CHR3-COOH wherein R3 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl (with certain provisos); and the lactams thereof when Z is H2N(CH2)n- and Rb is hydrogen.
GB7827967A 1977-07-11 1978-06-27 Alpha-halomethyl derivatives of alpha-amino acids Expired GB2001960B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US81476577A 1977-07-11 1977-07-11
US2875779A 1979-04-10 1979-04-10
US2875879A 1979-04-10 1979-04-10

Publications (2)

Publication Number Publication Date
GB2001960A true GB2001960A (en) 1979-02-14
GB2001960B GB2001960B (en) 1982-02-24

Family

ID=27363337

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7827967A Expired GB2001960B (en) 1977-07-11 1978-06-27 Alpha-halomethyl derivatives of alpha-amino acids

Country Status (9)

Country Link
JP (1) JPS5419913A (en)
AU (1) AU522660B2 (en)
BE (3) BE868882A (en)
CA (1) CA1091661A (en)
CH (1) CH642055A5 (en)
DE (1) DE2828739A1 (en)
FR (1) FR2430418A1 (en)
GB (1) GB2001960B (en)
NL (2) NL190662C (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0046713A1 (en) * 1980-08-23 1982-03-03 Merrell Toraude Et Compagnie Fluorinated pentene diamine derivatives
JPS5841843A (en) * 1981-08-19 1983-03-11 メレル・トロ−ド・エ・カンパニ− Fluorinated diaminoalkene derivative
JPS5874641A (en) * 1981-08-19 1983-05-06 メレル・トロ−ド・エ・カンパニ− Decarboxylase-inhibiting fluorinated alkane diamine derivative
WO2021209563A1 (en) 2020-04-16 2021-10-21 Som Innovation Biotech, S.A. Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus
CN120943886A (en) * 2025-10-16 2025-11-14 浙江肽昇生物医药有限公司 A method for synthesizing the tripeptide Fmoc-Pro-Pro-Pro-OH

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4399151A (en) 1980-06-16 1983-08-16 Merrell Dow Pharmaceuticals Inc. Method of inhibiting the growth of protozoa
PH16634A (en) * 1980-06-16 1983-12-05 Merrell Dow Pharma Method of inhibiting the growth of protozoa
JPS5791958A (en) * 1980-08-23 1982-06-08 Merrell Toraude & Co Fluorinated pentene diamine derivative
US4437873A (en) 1981-03-23 1984-03-20 Merrell Dow Pharmaceuticals Inc. Method of inhibiting algae
US4435425A (en) 1982-04-09 1984-03-06 Merrell Toraude Et Compagnie Fluorinated diaminobutane derivatives
JPS62148462A (en) * 1985-12-19 1987-07-02 メレルダウフア−マス−テイカルズ　インコ−ポレ−テツド Novel method of controlling growth of protozoa
EP0326766B1 (en) * 1988-02-05 1992-06-17 Merrell Dow Pharmaceuticals Inc. 5-substituted ornithine derivatives
CA1319123C (en) * 1988-08-31 1993-06-15 Andrew T. Au Method for the production of (-) 2-substituted-ornithines
US6187296B1 (en) 1998-01-23 2001-02-13 The Board Of Regents Of The University Of Oklahoma Lysine decarboxylase inhibitors for the prevention and treatment of periodontal disease
US6103220A (en) * 1998-01-23 2000-08-15 Levine; Martin Lysine decarboxylase inhibitors for the prevention and treatment of periodontal disease
US7015349B2 (en) 2003-03-26 2006-03-21 The Gillette Company Reduction of hair growth

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ187377A (en) * 1977-06-01 1981-05-15 Merck & Co Inc A-amino-a-substituted alkyl-a-fluoromethylacetic acids

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0046713A1 (en) * 1980-08-23 1982-03-03 Merrell Toraude Et Compagnie Fluorinated pentene diamine derivatives
JPS5841843A (en) * 1981-08-19 1983-03-11 メレル・トロ−ド・エ・カンパニ− Fluorinated diaminoalkene derivative
JPS5874641A (en) * 1981-08-19 1983-05-06 メレル・トロ−ド・エ・カンパニ− Decarboxylase-inhibiting fluorinated alkane diamine derivative
WO2021209563A1 (en) 2020-04-16 2021-10-21 Som Innovation Biotech, S.A. Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus
CN120943886A (en) * 2025-10-16 2025-11-14 浙江肽昇生物医药有限公司 A method for synthesizing the tripeptide Fmoc-Pro-Pro-Pro-OH

Also Published As

Publication number Publication date
NL950027I2 (en) 1997-06-02
NL190662B (en) 1994-01-17
JPS5419913A (en) 1979-02-15
CA1091661A (en) 1980-12-16
BE881208A (en) 1980-05-16
DE2828739A1 (en) 1979-02-01
NL7807453A (en) 1979-01-15
BE868882A (en) 1978-11-03
GB2001960B (en) 1982-02-24
NL950027I1 (en) 1996-02-01
FR2430418A1 (en) 1980-02-01
FR2430418B1 (en) 1984-07-13
BE881209A (en) 1980-05-16
NL190662C (en) 1994-06-16
AU3732778A (en) 1980-01-03
JPH0122259B2 (en) 1989-04-25
CH642055A5 (en) 1984-03-30
AU522660B2 (en) 1982-06-17

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Legal Events

Date Code Title Description
CTFF Supplementary protection certificate filed

Free format text: SPC/GB93/118, 930629

CTFG Supplementary protection certificate granted

Free format text: SPC/GB93/118, 931203, EXPIRES:20030626

PE20 Patent expired after termination of 20 years

Effective date: 19980626

CTFE Supplementary protection certificate entered into force

Free format text: SPC/GB93/118, 19980627, EXPIRES: 20030626

SPCE Supplementary protection certificate expired

Spc suppl protection certif: SPC/GB93/118

Expiry date: 20030626