# US 4,393,225 A · AI-77 Compounds and pharmaceutically acceptable salts thereof

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- Number: US 4,393,225 A
- Document ID: US4393225A
- Status: Granted
- Kind: A
- Application number: 06/167,581
- Filed: 1980-07-11
- Granted: 1983-07-12
- Earliest claimed: 1979-07-11
- Assignees: Asahi Kasei Kogyo Kabushiki Kaisha
- Inventors: Hiroshi Hayashi; Yukiji Shimojima; Takashi Shirai; Torao Ishida; Mitsuru Shibukawa
- Web page: https://patentgrep.com/patent/US4393225A

## CPC

- C12N 1/205: Bacterial isolates
- C07D 311/76: Benzo[c]pyrans
- C12P 13/02: Amides, e.g. chloramphenicol {or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes (peptides C12P21/00 or C07K)}
- C12P 17/06: containing a six-membered hetero ring, e.g. fluorescein
- C12P 17/162: {Heterorings having oxygen atoms as the only ring heteroatoms, e.g. Lasalocid}
- C12R 2001/07: Bacillus
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12R: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS

## Abstract

AI-77 compounds, pharmaceutically acceptable salts thereof, and a process for the preparation thereof are described, said compounds having the formulae ##STR1## wherein: X is NR.sub.6 or O; Y is NHR.sub.5 or combine with Z to provide a link for bonding C and C; Z is H or combines with Y to provide a link for bonding C and C; R.sub.1, R.sub.3 and R.sub.5 are each H, R', --CH.sub.2 R, or --COR; R.sub.6 is H or R; R.sub.7 is H, R or CH.sub.2 R; R is a hydrocarbon group consisting of a saturated or unsaturated straight or branched aliphatic group of C.sub.1 to C.sub.17, an aromatic group of C.sub.6 to C.sub.10, a cage type group of C.sub.7 to C.sub.10, a monocyclic aliphatic group of C.sub.3 to C.sub.8, an aromatic-aliphatic group of C.sub.7 to C.sub.15, a heterocyclic hydrocarbon of C.sub.1 to C.sub.9, wherein the above hydrocarbons can be substituted with one or more groups selected from halogen, oxo, carboxyl, hydroxyl, a saturated or unsaturated straight or branched aliphatic group of C.sub.1 to C.sub.5, an aromatic group of C.sub.6 to C.sub.10, a monocyclic aliphatic group of C.sub.3 to C.sub.8, an aromatic-aliphatic group of C.sub.7 to C.sub.11, alkoxy of C.sub.1 to C.sub.5, thioalkoxyl of C.sub.1 to C.sub.5, carboalkoxyl of C.sub.1 to C.sub.6, acyl of C.sub.1 to C.sub.5, acyloxy of C.sub.2 to C.sub.6 and a heterocyclic group of C.sub.1 to C.sub.9 ; R' is the same as R exclusive of those groups wherein unsaturated carbon or tertiary carbon is directly bonded to O or N; R.sub.2 is H, or combines with T.sub.1 to provide a link for bonding C and O in a lactone ring; T.sub.1 is OH or combines with R.sub.2 to provide a link for bonding C and O in a lactone ring; R.sub.4 is H or combines with T.sub.2 to provide a link for bonding C and O in a lactone ring; and T.sub.2 is OH or combines with R.sub.4 to provide a link for bonding C and O in a lactone ring; and pharmaceutically acceptable salts thereof.

## Claims

### Claim 1

An AI-77 compound of the formula (I) or (II): ##STR792## wherein: X is NR.sub.6 or O;
Y is NHR.sub.5 or combines with Z to provide a link for bonding C and C;
Z is H or combines with Y to provide a link for bonding C and C;
R.sub.1, R.sub.3 and R.sub.5 are each H, R', --CH.sub.2 R, or --COR;
R.sub.6 is H or R;
R.sub.7 is H, R or CH.sub.2 R;
R is a hydrocarbon group consisting of a straight or branched alkyl group of C.sub.1 to C.sub.17 containing from 0 to 3 double bonds or triple bonds, an aromatic group of C.sub.6 to C.sub.10, a bridged hydrocarbon group of C.sub.7 to C.sub.10, a cycloalkyl group of C.sub.3 to C.sub.8 and an arylaliphatic group having a C.sub.6 to C.sub.10 aromatic group on a C.sub.1 to C.sub.5 aliphatic group, wherein the above hydrocarbons can be substituted with halogen, oxo, carboxyl, hydroxyl, a straight or branched aliphatic group of C.sub.1 to C.sub.5 containing from 0 to 3 double bonds or triple bonds, an aromatic group of C.sub.6 to C.sub.10, a cycloalkyl group of C.sub.3 to C.sub.8, an aromatic-aliphatic group of C.sub.7 to C.sub.11, alkoxy of C.sub.1 to C.sub.5, thioalkoxyl or C.sub.1 to C.sub.5, carboalkoxy of C.sub.2 to C.sub.6, acyl of C.sub.1 to C.sub.6 or acyloxy of C.sub.2 to C.sub.6 ;
R' is the same as R exclusive of those groups wherein unsaturated carbon or tertiary carbon is directly bonded to O or N;
R.sub.4 is H or combines with T.sub.2 to provide a link for bonding C and O in a lactone ring; and
T.sub.2 is OH or combines with R.sub.4 to provide a link for bonding C and O in a lactone ring;
or a pharmaceutically acceptable salt thereof with hydrohalogenic acid, phosphoric acid, sulfuric acid, oxalic acid, maleic acid or an organic sulfonic acid.

### Claim 2 (depends on 1)

A compound of the formula (I) according to claim 1 wherein said compound is represented by the formula ##STR793## or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

A compound of the formula (I) according to claim 1 wherein said compound is represented by the formula ##STR794## or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

A compound of the formula (I) according to claim 1 wherein said compound is represented by the formula ##STR795## wherein R.sub.9 is methyl or ethyl; or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 1)

A compound of the formula (I) according to claim 1 wherein said compound is represented by the formula ##STR796## or a pharmaceutically acceptable salt thereof.