# US 5,703,100 A · Modulators of acetylcholine receptors

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,703,100 A
- Document ID: US5703100A
- Status: Granted
- Kind: A
- Application number: 08/485,398
- Filed: 1995-06-07
- Granted: 1997-12-30
- Earliest claimed: 1994-11-10
- Assignees: Sibia Neurosciences, Inc.
- Inventors: Ian A. McDonald; Jeffrey P. Whitten; Nicholas D. Cosford
- Web page: https://patentgrep.com/patent/US5703100A

## CPC

- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/02: for peripheral neuropathies
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 25/30: for treating abuse or dependence
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 405/14: containing three or more hetero rings
- C07F 7/0814: {said ring is substituted at a C ring atom by Si}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

In accordance with the present invention, there is provided a class of pyridine compounds which are modulators of acetylcholine receptors. The compounds of the invention displace acetylcholine receptor ligands from their binding sites. Invention compounds may act as agonists, partial agonists, antagonists or allosteric modulators of acetylcholine receptors, and are useful for a variety of therapeutic applications, such as the treatment of Alzheimer's disease and other disorders involving memory loss and/or dementia (including AIDS dementia); disorders of attention and focus (such as attention deficit disorder); disorders of extrapyramidal motor function such as Parkinson's disease, Huntington's disease, Gilles de la Tourette syndrome and tardive dyskinesia; mood and emotional disorders such as depression, panic, anxiety and psychosis; substance abuse including withdrawal syndromes and substitution therapy; neuroendocrine disorders and dysregulation of food intake, including bulimia and anorexia; disorders of nociception and control of pain; autonomic disorders including dysfunction of gastrointestinal motility and function such as inflammatory bowel disease, irritable bowel syndrome, diarrhea, constipation, gastric acid secretion and ulcers; pheochromocytoma; cardiovascular dysfunction including hypertension and cardia arrhythmias, comedication in surgical procedures, and the like.

## Claims

### Claim 1

A compound having the structure ##STR9## wherein A is a 1, 2 or 3 atom bridging species which forms part of a saturated or monounsaturated 5-, 6- or 7-membered ring including N.sup.7, C.sup.8, C.sup.9 and B;
B is selected from --O--, --S--, --NR.sup.10, wherein R.sup.10 is selected from hydrogen, lower alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl; --C.sup.10 HR.sup.10a --, wherein R.sup.10a is selected from hydrogen, lower alkyl, hydroxyalkyl, aryl, aryloxyalkyl, fluoro, trifluoromethyl, cyano, cyanomethyl, --OR', --NR'.sub.2, or --SR', wherein each R' is independently hydrogen, lower alkyl, alkenyl, alkynyl or aryl, provided, however, that neither the --NR'.sub.2 nor the --SR' functionality is conjugated with an alkenyl or alkynyl functionality; or B is .dbd.C.sup.10 R.sup.10a -- or .dbd.N--, provided there is no double bond in the ring between A and B, or between B and C.sup.9 when there is a double bond between N.sup.7 and C.sup.8, and provided that B is not a heteroatom when A is a 1 atom bridging species;
R.sup.2, R.sup.4, and R.sup.6 are each independently selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic, trifluoromethyl, halogen, cyano, nitro;
--S(O)R', --S(O)R' or --S(O).sub.2 NHR', wherein each R' is as defined above, provided, however, that when R.sup.2, R.sup.4, R.sup.5 or R.sup.6 is --S(O)R', R' is not hydrogen, alkenyl or alkynyl, and provided that when R.sup.2, R.sup.4, R.sup.5 or R.sup.6 is S(O).sub.2 NHR', R' is not alkenyl or alkynyl;
--C(O)R", wherein R" is selected from hydrogen, alkyl, substituted alkyl, alkoxy, alkylamino, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, aryloxy, arylamino, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic or trifluoromethyl, provided, however, that the carbonyl functionality is not conjugated with an alkenyl or alkynyl functionality;
--OR''', wherein R''' is selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, aroyl, substituted aroyl, heterocyclic, substituted heterocyclic, acyl, trifluoromethyl, alkylsulfonyl or arylsulfonyl, provided, however, that the --OR''' functionality is not conjugated with an alkenyl or alkynyl functionality;
--NR'''.sub.2, wherein each R''' is independently as defined above, or each R''' and the N to which they are attached can cooperate to form a 4-, 5-, 6- or 7-membered ring; provided, however, that the --NR'''.sub.2 functionality is not conjugated with an alkenyl or alkynyl functionality;
--SR"", wherein R"" is selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic or trifluoromethyl, provided, however, that the --SR"" functionality is not conjugated with an alkenyl or alkynyl functionality; or
--SiR'"".sub.3, wherein R'"" is selected from alkyl or aryl;
R.sup.5 is selected from alkynyl, substituted alkynyl, aryl or substituted aryl;
R.sup.7 is selected from hydrogen, lower alkyl, aryl, substituted aryl, alkylaryl, or substituted alkylaryl, or R.sup.7 is absent when there is a double bond between N.sup.7 and C.sup.8 ; and
R.sup.9 and R.sup.9a are each independently selected from hydrogen, lower alkyl, hydroxyalkyl, aryl, aryloxyalkyl, fluoro, trifluoromethyl, cyano, cyanomethyl, --OR', --NR'.sub.2, or --SR', wherein each R' is as defined above, provided, however, that neither the --NR'.sub.2 nor the --SR' functionality is conjugated with an alkenyl or alkynyl functionality.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein A is a 1, 2 or 3 atom bridging species selected from alkylene, or --O--, --C(O)--, --N(R.sup.11)--, and/or --S--containing alkylene moiety, wherein R.sup.11 is hydrogen or a lower alkyl moiety; provided, however, that the ring formed by N.sup.7, C.sup.8, C.sup.9, A and B does not contain any covalent heteroatom-heteroatom single bonds, or any heteroatom-methylene-heteroatom bonding relationships.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein A is selected from --CH.sub.2 --, --CH.sub.2 CH.sub.2 --or --C(O)--.

### Claim 4 (depends on 1)

A compound according to claim 1 wherein B is C.sup.10 HR.sup.10a --, wherein R.sup.10a is selected from hydrogen or lower alkyl.

### Claim 5 (depends on 4)

A compound according to claim 4 wherein R.sup.10a is hydrogen.

### Claim 6 (depends on 1)

A compound according to claim 1 wherein R.sup.2 is hydrogen or amino.

### Claim 7 (depends on 1)

A compound according to claim 1 wherein R.sup.4 is selected from hydrogen, aryl, alkoxy or aryloxy.

### Claim 8 (depends on 1)

A compound according to claim 1 wherein R.sup.5 is selected from alkynyl, aryl, substituted aryl, trialkylsilyl, arylalkyl, arylalkenyl or arylalkynyl.

### Claim 9 (depends on 1)

A compound according to claim 1 wherein the alkynyl moiety at R.sup.5 has the structure:
--C.tbd.C--R.sup.5'
wherein R.sup.5' is selected from hydrogen alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic, trifluoromethyl, halogen, cyano, nitro;
--S(O)R', --S(O).sub.2 R' or --S(O).sub.2 NHR', wherein each R' is as defined above, provided, however, that when R.sup.2, R.sup.4, R.sup.5 or R.sup.6 is --S(O)R', R' is not hydrogen, alkenyl or alkynyl, and provided that when R.sup.2, R.sup.4, R.sup.5 or R.sup.6 is --S(O).sub.2 NHR', R' is not alkenyl or alkynyl;
--C(O)R", wherein R" is selected from hydrogen, alkyl, substituted alkyl, alkoxy, alkylamino, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, aryloxy, arylamino, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic or trifluoromethyl, provided, however, that the carbonyl functionality is not conjugated with an alkenyl or alkynyl functionality;
--OR'" , wherein R'" is selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, aroyl, substituted aroyl, heterocyclic, substituted heterocyclic, acyl, trifluoromethyl, alkylsulfonyl or arylsulfonyl, provided, however, that the --OR'" functionality is not conjugated with an alkenyl or alkynyl functionality;
--NR'".sub.2, wherein each R'" is independently as defined above, or each R'" and the N to which they are attached can cooperate to form a 4-, 5-, 6- or 7- membered ring; provided, however, that the --NR'".sub.2 functionality is not conjugated with an alkenyl or alkynyl functionality;
--SR"", wherein R"" is selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic or trifluoromethyl, provided, however, that the --SR"" functionality is not conjugated with an alkenyl or alkynyl functionality; or
--SiR'"".sub.3, wherein R'"" is selected from alkyl or aryl;
alkylene, substituted alkylene, arylene, substituted arylene, so that the resulting compound is a polyfunctional species, bearing two or more of the substituted pyridyl structures contemplated by structure I.

### Claim 10 (depends on 9)

A compound according to claim 9 wherein R.sup.5' is hydrogen, methyl, ethyl, propyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, methoxymethyl, 2-hydroxy-2-isopropyl, dimethylaminomethyl or phenyl.

### Claim 11 (depends on 1)

A compound according to claim 1 wherein R.sup.6 is selected from hydrogen, chlorine, amino, methyl or alkoxy.

### Claim 12 (depends on 1)

A compound according to claim 1 wherein R.sup. 7 is absent or selected from hydrogen or methyl.

### Claim 13 (depends on 1)

A compound according to claim 1 wherein R.sup.9 and R.sup.9a are each independently selected from hydrogen, lower alkyl, alkoxy or aryloxy.

### Claim 14 (depends on 1)

A compound according to claim 1 wherein said compound is substantially optically pure.

### Claim 15 (depends on 1)

A compound according to claim 1 wherein said compound is a racemic mixture or a diasteromeric mixture.

### Claim 16 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =an alkynyl moiety having the structure:
--C.tbd.C--R.sup.5'
wherein R.sup.5' is selected from hydrogen, lower alkyl, hydroxyalkyl, alkoxyalkyl, dialkylaminoalkyl, aryl or 5-›1-(10-›5-(3-›1-methyl-2-pyrrolidinyl!pyridine) deca-1,9-diynyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 17 (depends on 16)

A compound according to claim 16 wherein R.sup.5' is selected from hydrogen, methyl, ethyl, propyl, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, methoxymethyl, 1-hydroxyisopropyl, dimethylaminomethyl, and phenyl.

### Claim 18 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =3-chloro-4-hydroxyphenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 19 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
.dbd.--CH.sub.3 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =3-chlorophenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 20 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or ---CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =3-fluoro-4-methoxyphenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 21 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =4-hydroxyphenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 22 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =4-biphenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 23 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =phenylethynyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 24 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =4-methoxyphenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 25 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =4-fluorophenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 26 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =3-fluoro-4-hydroxyphenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 27 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =4-methylphenyl,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 28 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --or --CH.sub.2 CH.sub.2 --,
B=--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 is selected from 3-chloro-4-methoxyphenyl, 4-aminophenyl, 4-acetamidophenyl, 4-acetoxyphenyl, 3-chloro-4-acetoxyphenyl, 3-chloro-4-acetamidophenyl, 4-methane sulfonanilido, or 3-chloro-4-methanesulfonanilido,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 29 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 is selected from ethynyl, 3-chloro-4-hydroxyphenyl, 3-chlorophenyl, 3-fluoro-4-methoxyphenyl, 4-hydroxyphenyl, 4-biphenyl, phenylethynyl, 4-methoxyphenyl, 4-fluorophenyl, 3-fluoro-4-hydroxyphenyl or 4-methylphenyl,
R.sup.6 =hydrogen,
R.sup.7 is not present due to the presence of a double bond between N.sup.7 and C.sup.8,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 30 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 is selected from 3-chloro-4-methoxyphenyl, 4-aminophenyl, 4-acetamidophenyl, 4-acetoxyphenyl, 3-chloro-4-acetoxyphenyl, 3-chloro-4-acetamidophenyl , 4-methane sulfonanilido, or 3-chloro-4-methanesulfonanilido,
R.sup.6 =hydrogen,
R.sup.7 is not present due to the presence of a double bond between N.sup.7 and C.sup.8,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 31

A pharmaceutical composition comprising a compound of the structure ##STR10## in the form of a pharmaceutically acceptable non-toxic acid addition salt, wherein:
A is a 1, 2 or 3 atom bridging species which forms part of a saturated or monounsaturated 5-, 6- or 7-membered ring including N.sup.7, C.sup.8, C.sup.9 and B;
B is selected from --O--, --S--, --NR.sup.10 --, wherein R.sup.10 is selected from hydrogen, lower alkyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl; --C.sup.10 HR.sup.10a --, wherein R.sup.10a is selected from hydrogen, lower alkyl, hydroxyalkyl, aryl, aryloxyalkyl, fluoro, trifluoromethyl, cyano, cyanomethyl, --OR', --NR'.sub.2, or --SR', wherein each R' is independently hydrogen, lower alkyl, alkenyl, alkynyl or aryl, provided, however, that neither the --NR'.sub.2 nor the --SR' functionality is conjugated with an alkenyl or alkynyl functionality; or B is .dbd.C.sup.10 R.sup.10a -- or .dbd.N--, provided there is no double bond in the ring between A and B, or between B and C.sup.9 when there is a double bond between N.sup.7 and C.sup.8, and provided that B is not a heteroatom when A is a 1 atom bridging species;
R.sup.2, R.sup.4, and R.sup.6 are each independently selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic, trifluoromethyl, halogen, cyano, nitro;
--S(O)R', --S(O).sub.2 R' or --S(O).sub.2 NHR', wherein each R' is as defined above, provided, however, that when R.sup.2, R.sup.4, R.sup.5 or R.sup. 6 is --S(O)R', R' is not hydrogen, alkenyl or alkynyl, and provided that when R.sup.2, R.sup.4, R.sup.5 or R.sup.6 is S(O).sub.2 NHR', R' is not alkenyl or alkynyl;
--C(O)R", wherein R" is selected from hydrogen, alkyl, substituted alkyl, alkoxy, alkylamino, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, aryloxy, arylamino, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic or trifluoromethyl, provided, however, that the carbonyl functionality is not conjugated with an alkenyl or alkynyl functionality;
--OR'", wherein R'" is selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, aroyl, substituted aroyl, heterocyclic, substituted heterocyclic, acyl, trifluoromethyl, alkylsulfonyl or arylsulfonyl, provided, however, that the --OR'" functionality is not conjugated with an alkenyl or alkynyl functionality;
--NR'".sub.2, wherein each R'" is independently as defined above, or each R'" and the N to which they are attached can cooperate to form a 4-, 5-, 6- or 7-membered ring; provided, however, that the --NR'".sub.2, functionality is not conjugated with an alkenyl or alkynyl functionality;
--SR"", wherein R"" is selected from hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, alkylaryl, substituted alkylaryl, arylalkyl, substituted arylalkyl, heterocyclic, substituted heterocyclic or trifluoromethyl, provided, however, that the --SR"" functionality is not conjugated with an alkenyl or alkynyl functionality; or
--SiR'"".sub.3, wherein R'"" is selected from alkyl or aryl;
R.sup.5 is selected from alkynyl, substituted alkynyl, aryl, or substituted aryl;
R.sup.7 is selected from hydrogen, lower alkyl, aryl, substituted aryl, alkylaryl, or substituted alkylaryl, or R.sup.7 is absent when there is a double bond between N.sup.7 and C.sup.8 ; and
R.sup.9 and R.sup.9a are each independently selected from hydrogen, lower alkyl, hydroxyalkyl, aryl, aryloxyalkyl, fluoro, trifluoromethyl, cyano, cyanomethyl, --OR', --NR'.sub.2, or --SR', wherein each R' is as defined above, provided, however, that neither the --NR'.sub.2 nor the --SR' functionality is conjugated with an alkenyl or alkynyl functionality.

### Claim 32 (depends on 1)

A method of modulating the activity of acetylcholine receptors, said method comprising:
contacting cell-associated acetylcholine receptors with a sufficient concentration of a compound according to claim 1 to modulate the activity of said acetylcholine receptors.

### Claim 33 (depends on 1)

Method for treating Parkinson's disease, said method comprising administering a therapeutically effective amount of a compound according to claim 1 to a patient suffering from Parkinson's disease.

### Claim 34 (depends on 1)

Method for treating Alzheimer's disease, said method comprising administering a therapeutically effective amount of a compound according to claim 1 to a patient suffering from Alzheimer's disease.

### Claim 35 (depends on 1)

Method for treating dementia, said method comprising administering a therapeutically effective amount of a compound according to claim 1 to a patient suffering from dementia.

### Claim 36 (depends on 1)

Method for controlling pain, said method comprising administering a pain-reducing amount of a compound according to claim 1 to a patient suffering from pain.

### Claim 37 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 -- or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =--C.tbd.C--CH.sub.3,
R.sup.6 =hydrogen,
R.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 38 (depends on 1)

A compound according to claim 1 wherein:
A.dbd.--CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =--C.tbd.C--CH.sub.3,
R.sup.6 =hydrogen,
R.sup.7 =methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 39 (depends on 31)

A composition according to claim 31 wherein A, B, R.sup.2, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9 and R.sup.9a of said compound are defined as follows:
A.dbd.--CH.sub.2 -- or --CH.sub.2 CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =--C.tbd.C--CH.sub.3,
R.sup.6 =hydrogen,
.sup.7 =hydrogen or methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.

### Claim 40 (depends on 31)

A composition according to claim 31 wherein A, B, R.sup.2, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.9 and R.sup.9a of said compound are defined as follows:
A.dbd.--CH.sub.2 --,
B.dbd.--CH.sub.2 --,
R.sup.2 =hydrogen,
R.sup.4 =hydrogen,
R.sup.5 =--C.tbd.C--CH.sub.3,
R.sup.6 =hydrogen,
R.sup.7 =methyl,
R.sup.9 =hydrogen, and
R.sup.9a =hydrogen.