AU599610B2 - Derivatives of quinuclidine - Google Patents
Derivatives of quinuclidine Download PDFInfo
- Publication number
- AU599610B2 AU599610B2 AU64859/86A AU6485986A AU599610B2 AU 599610 B2 AU599610 B2 AU 599610B2 AU 64859/86 A AU64859/86 A AU 64859/86A AU 6485986 A AU6485986 A AU 6485986A AU 599610 B2 AU599610 B2 AU 599610B2
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- Australia
- Prior art keywords
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- pharmaceutical composition
- compound
- aryl
- af102b
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000008584 quinuclidines Chemical class 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 106
- 238000000034 method Methods 0.000 claims description 98
- 238000011282 treatment Methods 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 43
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 claims description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims description 41
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 claims description 41
- 229960001697 physostigmine Drugs 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 230000001713 cholinergic effect Effects 0.000 claims description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 23
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- 239000001257 hydrogen Substances 0.000 claims description 22
- -1 oyclohexyl Chemical group 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 20
- UANSQQFYKHHDJM-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=CC2=C1 UANSQQFYKHHDJM-KRWDZBQOSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 230000037396 body weight Effects 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 210000003169 central nervous system Anatomy 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical class C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 10
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 9
- 229960001231 choline Drugs 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 8
- 239000000787 lecithin Substances 0.000 claims description 8
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- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 8
- 229960001685 tacrine Drugs 0.000 claims description 8
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 claims description 7
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- OYTKINVCDFNREN-UHFFFAOYSA-N amifampridine Chemical compound NC1=CC=NC=C1N OYTKINVCDFNREN-UHFFFAOYSA-N 0.000 claims description 7
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- ZXNRTKGTQJPIJK-UHFFFAOYSA-N aniracetam Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(=O)CCC1 ZXNRTKGTQJPIJK-UHFFFAOYSA-N 0.000 claims description 7
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
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- 229960004526 piracetam Drugs 0.000 claims description 7
- ZULJGOSFKWFVRX-UHFFFAOYSA-N pramiracetam Chemical compound CC(C)N(C(C)C)CCNC(=O)CN1CCCC1=O ZULJGOSFKWFVRX-UHFFFAOYSA-N 0.000 claims description 7
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- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
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- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- LWKDQGSBGMZMNO-UHFFFAOYSA-N 3-methylidene-1-azabicyclo[2.2.2]octane Chemical compound C1CC2C(=C)CN1CC2 LWKDQGSBGMZMNO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL7756886 | 1986-01-10 | ||
| IL77568 | 1986-01-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6485986A AU6485986A (en) | 1987-07-16 |
| AU599610B2 true AU599610B2 (en) | 1990-07-26 |
Family
ID=11056499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU64859/86A Expired AU599610B2 (en) | 1986-01-10 | 1986-11-06 | Derivatives of quinuclidine |
Country Status (5)
| Country | Link |
|---|---|
| KR (1) | KR940009791B1 (enrdf_load_stackoverflow) |
| AR (1) | AR242213A1 (enrdf_load_stackoverflow) |
| AU (1) | AU599610B2 (enrdf_load_stackoverflow) |
| IN (1) | IN164199B (enrdf_load_stackoverflow) |
| ZA (1) | ZA868369B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU666734B2 (en) * | 1992-07-10 | 1996-02-22 | Daiichi Sankyo Company, Limited | Composition for curing Sjoegren syndrome disease |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL87234A (en) * | 1987-08-13 | 1992-02-16 | Israel Inst Biolog Res | Optical isomers of 2-methylspiro(1,3-oxathiolane-5,3')quinuclidine,their preparation and pharmaceutical compositions containing them |
| US4876260A (en) * | 1987-10-28 | 1989-10-24 | State Of Israel, Israel Institute Of Biological Research | Oxathiolanes |
| US4985420A (en) * | 1987-12-10 | 1991-01-15 | Duphar International Research B.V. | 1,7-annelated indolecarboxylic acid esters and -amides |
-
1986
- 1986-11-03 ZA ZA868369A patent/ZA868369B/xx unknown
- 1986-11-04 IN IN865/MAS/86A patent/IN164199B/en unknown
- 1986-11-06 AU AU64859/86A patent/AU599610B2/en not_active Expired
- 1986-11-07 AR AR86305822A patent/AR242213A1/es active
- 1986-11-10 KR KR1019860009513A patent/KR940009791B1/ko not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU666734B2 (en) * | 1992-07-10 | 1996-02-22 | Daiichi Sankyo Company, Limited | Composition for curing Sjoegren syndrome disease |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA868369B (en) | 1987-11-25 |
| KR870007165A (ko) | 1987-08-17 |
| KR940009791B1 (ko) | 1994-10-17 |
| AR242213A1 (es) | 1993-03-31 |
| AU6485986A (en) | 1987-07-16 |
| IN164199B (enrdf_load_stackoverflow) | 1989-01-28 |
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