# US 5,708,006 A · Neurokinin antagonists

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- Number: US 5,708,006 A
- Document ID: US5708006A
- Status: Granted
- Kind: A
- Application number: 08/476,987
- Filed: 1995-06-07
- Granted: 1998-01-13
- Earliest claimed: 1994-09-17
- Assignees: Boehringer Ingelheim GmbH
- Inventors: Horst Dollinger; Gerd Schnorrenberg; Hans Briem; Birgit Jung; Georg Speck
- Web page: https://patentgrep.com/patent/US5708006A

## CPC

- C07D 213/74: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C07D 211/14: with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C07D 211/22: by oxygen atoms
- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C07D 211/58: attached in position 4
- C07D 215/38: Nitrogen atoms (nitro radicals C07D215/18)
- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- C07D 295/125: with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D 317/58: Radicals substituted by nitrogen atoms (nitro radicals C07D317/52)
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 451/02: containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07C 2601/02: with a three-membered ring
- C07C 2601/14: The ring being saturated
- C07C 2601/18: with a ring being at least seven-membered
- C07C 2602/08: the other ring being five-membered, e.g. indane
- C07C 2602/10: the other ring being six-membered, e.g. tetraline
- C07C 2603/18: Fluorenes; Hydrogenated fluorenes
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The invention relates to new compounds of general formula I ##STR1## and the pharmaceutically acceptable salts thereof, wherein A, B, Z, R.sup.1, R.sup.2, R.sup.3 and m are defined as in the specification, processes for preparing them and pharmaceutical compositions containing these compounds. The compounds are valuable neurokinin (tachykinin) antagonists.

## Claims

### Claim 1

A compound of formula (I) ##STR16## wherein A is phenyl optionally substituted by one, two or three R.sup.4 ; B is --C(O)--CH.sub.2 -- or --C(O)--CH.sub.2 --CH.sub.2 --;
Z is piperidinyl substituted by R.sup.8 ;
R.sup.1 is H, C.sub.1-6 alkyl or phenyl;
R.sup.2 is H, C.sub.1-6 alkyl optionally substituted by a phenyl group or --CO--C.sub.1-3 alkyl optionally substituted by a phenyl group,
R.sup.3 is H, C.sub.1-6 alkyl, C.sub.1-6 alkyl substituted by one, two or three fluorine atoms, halogen or C.sub.1-6 alkoxy,
m is 1, 2 or 3;
each R.sup.4 is independently C.sub.1-6 alkyl, C.sub.1-6 alkyl substituted by one, two or three fluorine atoms, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio or halogen, or two adjacent R.sup.4 groups denote --O--(CH.sub.2)--O-- or --(CH.sub.2).sub.3-5 --;
R.sup.8 is hydrogen, C.sub.3-7 cycloalkyl, phenyl, ##STR17## C.sub.1-6 alkyl, allyl, --(CH.sub.2).sub.2-6 OH, --(C.sub.1-3)alkylphenyl, diphenylmethyl or --(C.sub.1-3)alkyl(C.sub.3-7)cycloalkyl, wherein the phenyl groups may be substituted by one or two substituents selected from methyl, F, Cl, OCH.sub.3, SCH.sub.3, CF.sub.3, OH or NO.sub.2, or substituted by --O--CH.sub.2 --O-- linking two adjacent carbon atoms of the phenyl; or R.sub.8 is --CH.sub.2 OH, --OH, ##STR18## wherein the last 6 groups mentioned are in position 3 or 4; R.sup.12 is H or methyl; and
R.sup.14 is H, C.sub.1-6 alkyl, phenyl or cyclohexyl, wherein if two R.sup.14 s are present and one of the R.sup.14 s is phenyl or cyclohexyl, the other R.sup.14 must be H.

### Claim 2 (depends on 1)

The compound according to claim 1 wherein B is --C(O)--CH.sub.2 -- and R.sup.1 is H.

### Claim 3

The compound N-›2-(3,4-dichlorophenyl)-2-(4-piperidine-1-yl)piperidine-1-yl)-ethyl!-2-( 3,5-bistrifluoromethylphenyl)-acetamide.

### Claim 4 (depends on 1, 2, 3)

A pharmaceutical composition comprising a compound according to claim 1, 2 or 3 and a pharmaceutically acceptable carrier.