IL102008A - Quinuclidine derivatives pharmaceutical compositions containing them and uses therof - Google Patents
Quinuclidine derivatives pharmaceutical compositions containing them and uses therofInfo
- Publication number
- IL102008A IL102008A IL10200892A IL10200892A IL102008A IL 102008 A IL102008 A IL 102008A IL 10200892 A IL10200892 A IL 10200892A IL 10200892 A IL10200892 A IL 10200892A IL 102008 A IL102008 A IL 102008A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- disorders
- substance
- formula
- methyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 150000008584 quinuclidines Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- 208000002193 Pain Diseases 0.000 claims abstract description 8
- 230000036407 pain Effects 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 55
- 208000035475 disorder Diseases 0.000 claims description 42
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims description 36
- 102100024304 Protachykinin-1 Human genes 0.000 claims description 36
- 101800003906 Substance P Proteins 0.000 claims description 36
- 241000124008 Mammalia Species 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 19
- 230000003042 antagnostic effect Effects 0.000 claims description 14
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- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 claims description 5
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 claims description 5
- VGGMVUWJFXUQBN-YBZGWEFGSA-N (2S,3S)-2-benzhydryl-N-(2-methoxy-5-propan-2-ylphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine dihydrochloride Chemical compound Cl.Cl.C(C)(C)C=1C=CC(=C(C1)N[C@@H]1[C@@](N2CCC1CC2)(C(C2=CC=CC=C2)C2=CC=CC=C2)C)OC VGGMVUWJFXUQBN-YBZGWEFGSA-N 0.000 claims description 2
- UYMNXIGGKXTLHU-VMPREFPWSA-N (2s,3s)-2-benzhydryl-n-(2-methoxy-5-methylphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C)C=C1N[C@@H]1[C@@](C(C=2C=CC=CC=2)C=2C=CC=CC=2)(C)N2CCC1CC2 UYMNXIGGKXTLHU-VMPREFPWSA-N 0.000 claims description 2
- QFTQKCRAJOXJNK-DKJKITOUSA-N (2s,3s)-2-benzhydryl-n-(5-butan-2-yl-2-methoxyphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound CCC(C)C1=CC=C(OC)C(N[C@@H]2[C@](N3CCC2CC3)(C)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QFTQKCRAJOXJNK-DKJKITOUSA-N 0.000 claims description 2
- ZXKQLZMZYWXUJC-CDZUIXILSA-N (2s,3s)-2-benzhydryl-n-(5-tert-butyl-2-methoxyphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)(C)C)C=C1N[C@@H]1[C@@](C(C=2C=CC=CC=2)C=2C=CC=CC=2)(C)N2CCC1CC2 ZXKQLZMZYWXUJC-CDZUIXILSA-N 0.000 claims description 2
- CWWARWOPSKGELM-SARDKLJWSA-N methyl (2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-5-amino-2-[[(2s)-5-amino-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s)-1-[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-5 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 CWWARWOPSKGELM-SARDKLJWSA-N 0.000 claims description 2
- QSBHMJMADHILTB-KYJUHHDHSA-N (2s,3s)-2-benzhydryl-n-(5-ethyl-2-methoxyphenyl)-2-methyl-1-azabicyclo[2.2.2]octan-3-amine Chemical compound CCC1=CC=C(OC)C(N[C@@H]2[C@](N3CCC2CC3)(C)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QSBHMJMADHILTB-KYJUHHDHSA-N 0.000 claims 1
- XPNMCDYOYIKVGB-CONSDPRKSA-N (2s,3s)-2-benzhydryl-n-[(2-methoxy-5-propan-2-ylphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine Chemical compound COC1=CC=C(C(C)C)C=C1CN[C@@H]1[C@H](C(C=2C=CC=CC=2)C=2C=CC=CC=2)N2CCC1CC2 XPNMCDYOYIKVGB-CONSDPRKSA-N 0.000 claims 1
- OPTAPOYRQUYZJY-UHFFFAOYSA-N CS(=O)(=O)O.CC1(N2CCC(C1N)CC2)C(C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound CS(=O)(=O)O.CC1(N2CCC(C1N)CC2)C(C2=CC=CC=C2)C2=CC=CC=C2 OPTAPOYRQUYZJY-UHFFFAOYSA-N 0.000 claims 1
- 230000011514 reflex Effects 0.000 claims 1
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- 239000003890 substance P antagonist Substances 0.000 abstract description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 abstract description 3
- 208000015114 central nervous system disease Diseases 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- -1 methoxybenzyl group Chemical group 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 229910052739 hydrogen Inorganic materials 0.000 description 5
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- HQPBPHWHPVDJQU-UHFFFAOYSA-N methanesulfonic acid;octan-3-amine Chemical compound CS(O)(=O)=O.CCCCCC(N)CC HQPBPHWHPVDJQU-UHFFFAOYSA-N 0.000 description 5
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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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
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Gastroenterology & Hepatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70840491A | 1991-05-31 | 1991-05-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL102008A0 IL102008A0 (en) | 1992-12-30 |
| IL102008A true IL102008A (en) | 1995-12-08 |
Family
ID=24845673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10200892A IL102008A (en) | 1991-05-31 | 1992-05-26 | Quinuclidine derivatives pharmaceutical compositions containing them and uses therof |
Country Status (41)
| Country | Link |
|---|---|
| US (3) | US5807867A (ja) |
| EP (1) | EP0587723B1 (ja) |
| JP (2) | JPH0733386B2 (ja) |
| KR (1) | KR100214905B1 (ja) |
| CN (1) | CN1048492C (ja) |
| AP (1) | AP299A (ja) |
| AT (1) | ATE135006T1 (ja) |
| AU (1) | AU657552B2 (ja) |
| BG (1) | BG61694B1 (ja) |
| BR (1) | BR9206073A (ja) |
| CA (1) | CA2102179C (ja) |
| CZ (1) | CZ281403B6 (ja) |
| DE (4) | DE122006000066I1 (ja) |
| DK (1) | DK0587723T3 (ja) |
| EG (1) | EG19944A (ja) |
| ES (1) | ES2084361T3 (ja) |
| FI (1) | FI114475B (ja) |
| GR (1) | GR3019687T3 (ja) |
| GT (1) | GT199200028A (ja) |
| HU (1) | HU217548B (ja) |
| IE (1) | IE72473B1 (ja) |
| IL (1) | IL102008A (ja) |
| IS (1) | IS1611B (ja) |
| LU (1) | LU91293I2 (ja) |
| MA (1) | MA22539A1 (ja) |
| MX (1) | MX9202554A (ja) |
| NL (1) | NL300250I2 (ja) |
| NO (2) | NO302701B1 (ja) |
| NZ (2) | NZ242956A (ja) |
| OA (1) | OA09867A (ja) |
| PL (1) | PL171379B1 (ja) |
| PT (1) | PT100546B (ja) |
| RO (1) | RO110499B1 (ja) |
| RU (1) | RU2103269C1 (ja) |
| SK (1) | SK390692A3 (ja) |
| TW (1) | TW204349B (ja) |
| UA (1) | UA27776C2 (ja) |
| UY (1) | UY23422A1 (ja) |
| WO (1) | WO1992021677A1 (ja) |
| YU (1) | YU48995B (ja) |
| ZA (1) | ZA923942B (ja) |
Families Citing this family (88)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9206073A (pt) * | 1991-05-31 | 1994-12-06 | Pfizer | Derivados de quinuclidina |
| EP0589924B1 (en) * | 1991-06-20 | 1996-09-04 | Pfizer Inc. | Fluoroalkoxybenzylamino derivatives of nitrogen containing heterocycles |
| CA2141048C (en) * | 1992-08-19 | 2003-03-18 | Harry R. Howard | Substituted benzylamino nitrogen containing non-aromatic heterocycles |
| US5886009A (en) * | 1992-11-12 | 1999-03-23 | Pfizer Inc. | Quinuclidine derivative as a substance P antagonist |
| US5344830A (en) * | 1992-12-10 | 1994-09-06 | Merck & Co., Inc. | N,N-diacylpiperazine tachykinin antagonists |
| IL109646A0 (en) * | 1993-05-19 | 1994-08-26 | Pfizer | Heteroatom substituted alkyl benzylamino-quinuclidines |
| JP2822274B2 (ja) * | 1993-05-19 | 1998-11-11 | ファイザー製薬株式会社 | Ｐ物質拮抗剤としてのヘテロ原子置換アルキルベンジルアミノキヌクリジン類 |
| US5393762A (en) * | 1993-06-04 | 1995-02-28 | Pfizer Inc. | Pharmaceutical agents for treatment of emesis |
| EP0653208A3 (en) * | 1993-11-17 | 1995-10-11 | Pfizer | Substance P antagonists for the treatment or prevention of sunburn. |
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