Peptides and process for preparing the same

• US 4,563,306 A
• Filed: 08/17/1984
• Issued: 01/07/1986
• Est. Priority Date: 09/07/1983
• Status: Expired due to Fees

• Current Assignee: Tanabe Seiyaku Co Ltd (Mitsubishi Chemical Group Corp.)
• Original Assignee: Tanabe Seiyaku Co Ltd (Mitsubishi Chemical Group Corp.)
• Inventors: Sugano, Hiroshi, Yamamura, Michio, Ishida, Ryuichi
• Primary Examiner(s): NOT, DEFINED
• Application Number:
  US06/641,978
• Time in Patent Office: 508 Days
• Field of Search: 260/112.5 TR, 514/18, 514/19
• US Class Current: 530/331
• CPC Class Codes: C07D 217/26 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 311/76 Benzo[c]pyrans
• CPC Class Codes: C07K 5/06147 and His-amino acid; Derivatives thereof
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

A compound of the formula: ##STR1## wherein A is a group of the formula: ##STR2## R¹ and R² are the same or different and each hydrogen atom, nitro, amino, a protected amino, hydroxy or lower alkoxy,

Y is oxygen atom or a group of the formula: --NR³ --,

R³ is hydrogen atom or lower alkyl,

X is methylene or sulfur atom and

the dotted line is an optional double bond, or a pharmaceutically acceptable acid addition salt thereof is useful as a medicine for the treatment of consciousness disorders.

Claims

1. A compound of the formula:

##STR20## wherein A is a group of the formula;

##STR21## R¹ and R² are the same or different and each hydrogen atom, nitro, amino, a protected amino, hydroxy or lower alkoxy,

Y is oxygen atom or a group of the formula;

--NR³ --,

R³ is hydrogen atom or lower alkyl,

X is methylene or sulfur atom and the dotted line is an optional double bond, or a pharmaceutically acceptable acid addition salt thereof.

2. The compound of claim 1, wherein R¹ and R² are the same or different and each hydrogen atom, nitro, amino, lower alkoxycarbonylamino, hydroxy or methoxy and R³ is hydrogen atom or methyl.

3. The compound of claim 2, wherein A is a group of the formula:

##STR22## R¹ and R² are the same or different and each hydrogen atom, nitro, amino, tert-butoxycarbonylamino, hydroxy or methoxy,

Y is oxygen atom or a group of the formula;

--NR³ --,

R³ is hydrogen atom or methyl and the dotted line is an optional double bond.

4. The compound of claim 3, wherein R¹ and R² are the same or different and each hydrogen atom, nitro or amino, Y is a group of the formula:

--NR³ --, R³ is hydrogen atom or methyl, X is methylene and the dotted line is an optional double bond.

5. The compound of claim 4, wherein A is a group of the formula:

##STR23## R¹ and R² are the same or different and each hydrogen atom or amino

Y is a group of the formula;

--NR³ --,

R³ is hydrogen atom or methyl and

X is methylene.

6. The compound of claim 5, wherein A and other constituent amino acid residues are all of the S-configuration.

7. The compound of claim 6, which is N.sup.α

-[(3S)-1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-L-histidyl-L-prolinamide or a pharmaceutically acceptable acid addition salt thereof.

8. The compound of claim 6, which is N.sup.α

-[(3S)-2-methyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-L-histidyl-L-prolinamide or a pharmaceutically acceptable acid addition salt thereof.

9. The compound of claim 6, which is N.sup.α

-[(3S)-1-oxo-7-amino-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]-L-histidyl-L-prolinamide or a pharmaceutically acceptable acid addition salt thereof.