# US 5,708,016 A · Pseudopeptides derived from neurokinins

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- Number: US 5,708,016 A
- Document ID: US5708016A
- Status: Granted
- Kind: A
- Application number: 08/801,037
- Filed: 1997-02-14
- Granted: 1998-01-13
- Earliest claimed: 1996-02-16
- Assignees: Adir et Compagnie
- Inventors: Jean-Luc Fauchere; Nathalie Kucharczyk-Gentric; Emmanuel Canet; Michel Lonchampt
- Web page: https://patentgrep.com/patent/US5708016A

## CPC

- C07K 5/0202: {containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids}
- A61P 1/08: for nausea, cinetosis or vertigo; Antiemetics
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/06: Antimigraine agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00)
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

A compound of formula (I): ##STR1## in which: R.sub.1 represents an indolyl, naphthyl, tetrahydronaphthyl, thienyl, phenyl, optionally substituted, or (C.sub.3 -C.sub.7)cycloalkyl group, n represents an integer such that 1.ltoreq.n.ltoreq.8, m represents an integer such that 1.ltoreq.m.ltoreq.4, R.sub.2 represents an unsubstituted or substituted benzyl group, an unsubstituted or substituted phenyl group or a linear or branched (C.sub.1 -C.sub.6)alkyl group, its enantiomers, diastereoisomers and epimers as well as its addition salts with a pharmaceutically acceptable acid or base, and medicinal products containing the same are useful as substance P antagonists.

## Claims

### Claim 1

A compound selected from the group consisting of those of formula (I): ##STR33## in which: R.sub.1 represents indolyl, naphthyl, tetrahydronaphthyl, thienyl, or phenyl, in each case unsubstituted or substituted with one or more halogen atoms, linear or branched (C.sub.1 -C.sub.6)alkyl, linear or branched (C.sub.1 -C.sub.6)alkoxy, hydroxyl, or trihalomethyl, or R.sub.1 represents a (C.sub.3 -C.sub.7)cycloalkyl group, n represents 1 to 8 inclusive, m represents 1 to 4 inclusive, R.sub.2 represents benzyl which is unsubstituted or substituted with one or more halogen atoms, linear or branched (C.sub.1 -C.sub.6)alkyl, linear or branched (C.sub.1 -C.sub.6)alkoxy, hydroxyl, or trihalomethyl, or phenyl which is unsubstituted or substituted with one or more halogen atoms, linear or branched (C.sub.1 -C.sub.6)alkyl, linear or branched (C.sub.1 -C.sub.6)alkoxy, hydroxyl, or trihalomethyl, or R.sub.2 represents a linear or branched (C.sub.1 -C.sub.6)alkyl group, its enantiomers, diastereoisomers and epimers, and its addition salts with a pharmaceutically-acceptable acid or base.

### Claim 2 (depends on 1)

A compound of claim 1, wherein R.sub.1 represents an indolyl group.

### Claim 3 (depends on 1)

A compound of claim 1, wherein R.sub.2 represents an unsubstituted or substituted benzyl group.

### Claim 4 (depends on 1)

A compound of claim 1, wherein R.sub.2 represents a 3,5-di(trifluoromethyl)benzyl group.

### Claim 5 (depends on 1)

A compound of claim 1, wherein n is equal to 4.

### Claim 6 (depends on 1)

A compound of claim 1, wherein m is equal to 1.

### Claim 7 (depends on 1)

The compound of claim 1 which is selected from {1-›4-(1H-tetrazol-5-yl)butyl!-3-indolyl}carbonyl-Hyp-Trp-OBzl(3,5-ditrifl uoromethyl), its isomers, and its addition salts with a pharmaceutically-acceptable acid or base.

### Claim 8 (depends on 1)

A method for treating living body afflicted with a condition selected from muscle contraction associated with NK.sub.1 receptors, plasma extravasation and bronchoconstriction comprising the step of administering to the living body an amount of a compound of claim 1 which is effective for alleviation of said condition.

### Claim 9 (depends on 1)

A pharmaceutical composition useful as a substance P antagonist comprising as active principle an effective amount of a compound of claim 1, together with one or more pharmaceutically-acceptable excipients or vehicles.