MX171888B - PROCEDURE FOR THE PREPARATION OF PROLINE DERIVATIVES - Google Patents

PROCEDURE FOR THE PREPARATION OF PROLINE DERIVATIVES

Info

Publication number
MX171888B
MX171888B MX010799A MX1079982A MX171888B MX 171888 B MX171888 B MX 171888B MX 010799 A MX010799 A MX 010799A MX 1079982 A MX1079982 A MX 1079982A MX 171888 B MX171888 B MX 171888B
Authority
MX
Mexico
Prior art keywords
alpha
group
formula
amino acid
preparation
Prior art date
Application number
MX010799A
Other languages
Spanish (es)
Inventor
Isao Matsunaga
Tomoyasu Iwaoka
Noriko Obatake
Yunichiro Aono
Yoshikazu Hinohara
Hideki Nakano
Masafumi Fukushima
Hiroyuki Nabata
Kazushige Sakai
Shun-Ichi Hata
Sadako Tanaka
Kiyonori Kuromaru
Yasuo Fujimura
Original Assignee
Chugai Pharmaceutical Co 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
Priority claimed from JP56094002A external-priority patent/JPS57209270A/en
Priority claimed from JP56137823A external-priority patent/JPS5839661A/en
Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd
Publication of MX171888B publication Critical patent/MX171888B/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La presente invención se refiere a un procedimiento para la preparación de derivados de prolina, de la fórmula (I): ( en donde R es un grupo unido al grupo alfa-amino del aminoácido, y se selecciona del grupo que consta de ciclopropancarbonilo, ciclohexancarbonilo y adamantancarbonilo; A es glicina, sarcosina o un radical de alfa-D-aminoácido, y tiene un grupo alfa-carbonilo que forma un tiol-ester unido con un átomo de azufre), o sus sales farmaceuticas aceptables, caracterizado por hacer reaccionar un compuesto de la fórmula (IV): R - A' - OH ( en donde A' es glicina, sarcosina o un radial de alfa-D-amino ácido, protegido o sin proteger; y R tiene las definiciones señaladas anteriormente), o su derivado reactivo, con un compuesto de la fórmula (V); ( en donde R' es un átomo de hidrógeno o un grupo protector del carboxilo), o su derivado reactivo, en un solvente orgánico inerte, a una temperatura entre -50 y + 20 grados C, remover cualquier grupo protector del producto de reacción y, opcionalmente, convertir el producto de reacción en una sal farmaceutica aceptable.The present invention relates to a process for the preparation of proline derivatives, of the formula (I): (wherein R is a group attached to the alpha-amino group of the amino acid, and is selected from the group consisting of cyclopropancarbonyl, cyclohexancarbonyl and adamantancarbonyl; A is glycine, sarcosine, or an alpha-D-amino acid radical, and has an alpha-carbonyl group that forms a thiol-ester linked with a sulfur atom), or its acceptable pharmaceutical salts, characterized by reacting a compound of formula (IV): R - A '- OH (where A' is glycine, sarcosine or a radial of alpha-D-amino acid, protected or unprotected; and R has the definitions outlined above), or its reactive derivative, with a compound of formula (V); (where R 'is a hydrogen atom or a carboxyl protecting group), or its reactive derivative, in an inert organic solvent, at a temperature between -50 and + 20 degrees C, remove any protecting group from the reaction product and optionally converting the reaction product to an acceptable pharmaceutical salt.

MX010799A 1981-06-19 1982-06-16 PROCEDURE FOR THE PREPARATION OF PROLINE DERIVATIVES MX171888B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP56094002A JPS57209270A (en) 1981-06-19 1981-06-19 Proline derivative
JP56137823A JPS5839661A (en) 1981-09-03 1981-09-03 Preparation of proline derivative

Publications (1)

Publication Number Publication Date
MX171888B true MX171888B (en) 1993-11-23

Family

ID=26435270

Family Applications (2)

Application Number Title Priority Date Filing Date
MX193189A MX155724A (en) 1981-06-19 1982-06-16 PROCEDURE FOR THE PREPARATION OF PROLINE DERIVATIVES
MX010799A MX171888B (en) 1981-06-19 1982-06-16 PROCEDURE FOR THE PREPARATION OF PROLINE DERIVATIVES

Family Applications Before (1)

Application Number Title Priority Date Filing Date
MX193189A MX155724A (en) 1981-06-19 1982-06-16 PROCEDURE FOR THE PREPARATION OF PROLINE DERIVATIVES

Country Status (19)

Country Link
KR (1) KR890000769B1 (en)
AT (1) AT377496B (en)
CA (1) CA1235120A (en)
CH (1) CH651825A5 (en)
DE (1) DE3222779A1 (en)
DK (1) DK156054C (en)
ES (2) ES8307216A1 (en)
FI (1) FI75804C (en)
FR (1) FR2508040B1 (en)
GB (1) GB2102412B (en)
HU (1) HU188177B (en)
IL (1) IL65954A (en)
IT (1) IT1157053B (en)
MX (2) MX155724A (en)
NL (1) NL193282C (en)
NO (1) NO156408C (en)
PT (1) PT75076B (en)
SE (1) SE453595B (en)
SU (1) SU1316556A3 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6354321A (en) * 1985-03-27 1988-03-08 Ajinomoto Co Inc Blood sugar lowering agent
KR870007114A (en) * 1986-01-21 1987-08-14 우에노 기미오 Stable Solid Agents of Thiol Ester Derivatives
ZA896851B (en) 1988-09-14 1990-06-27 Hoffmann La Roche Use of ace-inhibitors
EP0634175B1 (en) * 1993-07-15 2001-01-10 F. Hoffmann-La Roche Ag Pharmaceutical combination, containing a renin-angiotensin-system inhibitor and an endothelin antagonist

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA802420B (en) * 1979-05-18 1981-04-29 Squibb & Sons Inc Aminoacyl derivatives of mercaptoacyl amino acids

Also Published As

Publication number Publication date
ATA558581A (en) 1984-08-15
DE3222779A1 (en) 1983-01-27
MX155724A (en) 1988-04-20
GB2102412A (en) 1983-02-02
PT75076B (en) 1984-05-09
CA1235120A (en) 1988-04-12
ES513277A0 (en) 1983-07-01
FI822171A0 (en) 1982-06-16
NL193282C (en) 1999-05-06
DK156054C (en) 1989-11-06
ES520582A0 (en) 1984-04-01
DE3222779C2 (en) 1991-01-03
SE8203814L (en) 1982-12-20
NO821997L (en) 1982-12-20
CH651825A5 (en) 1985-10-15
IT1157053B (en) 1987-02-11
ES8403868A1 (en) 1984-04-01
GB2102412B (en) 1985-01-09
NO156408B (en) 1987-06-09
IL65954A (en) 1986-03-31
FR2508040B1 (en) 1986-07-04
DK156054B (en) 1989-06-19
FI822171L (en) 1982-12-20
IL65954A0 (en) 1982-09-30
FR2508040A1 (en) 1982-12-24
NO156408C (en) 1987-09-16
SE453595B (en) 1988-02-15
ES8307216A1 (en) 1983-07-01
PT75076A (en) 1982-07-01
FI75804B (en) 1988-04-29
HU188177B (en) 1986-03-28
DK273082A (en) 1982-12-20
KR840000488A (en) 1984-02-22
SU1316556A3 (en) 1987-06-07
IT8267772A0 (en) 1982-06-16
NL193282B (en) 1999-01-04
NL8202472A (en) 1983-01-17
AT377496B (en) 1985-03-25
FI75804C (en) 1988-08-08
KR890000769B1 (en) 1989-04-05

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