ZA200206956B - Derivatives of quinoline as alpha-2 antagonists. - Google Patents
Derivatives of quinoline as alpha-2 antagonists. Download PDFInfo
- Publication number
- ZA200206956B ZA200206956B ZA200206956A ZA200206956A ZA200206956B ZA 200206956 B ZA200206956 B ZA 200206956B ZA 200206956 A ZA200206956 A ZA 200206956A ZA 200206956 A ZA200206956 A ZA 200206956A ZA 200206956 B ZA200206956 B ZA 200206956B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- alkoxy
- formula
- mono
- Prior art date
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- 239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 title description 12
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 196
- 150000001875 compounds Chemical class 0.000 claims description 153
- 125000003545 alkoxy group Chemical group 0.000 claims description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 65
- 125000003282 alkyl amino group Chemical group 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- -1 (C3-Cg)cycloalky Chemical group 0.000 claims description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 239000005557 antagonist Substances 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000002837 carbocyclic group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 13
- 210000003169 central nervous system Anatomy 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 108060003345 Adrenergic Receptor Proteins 0.000 claims description 10
- 102000017910 Adrenergic receptor Human genes 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 8
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004559 acridin-9-yl group Chemical group C1=CC=CC2=NC3=CC=CC=C3C(=C12)* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000001555 benzenes Chemical group 0.000 claims description 2
- ASJSNRRPCZXGRL-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)phenyl]-1,2,3,4-tetrahydroacridin-9-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=C(CCCC2)C2=NC2=CC=CC=C12 ASJSNRRPCZXGRL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- VBDVCLHMPVSOQZ-UHFFFAOYSA-N 2-[4-[4-(acridin-9-ylamino)phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 VBDVCLHMPVSOQZ-UHFFFAOYSA-N 0.000 claims 1
- 101150110920 FRO1 gene Proteins 0.000 claims 1
- GOVQEKRSQZBPAX-UHFFFAOYSA-N [1-[4-(acridin-9-ylamino)phenyl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1C(C=C1)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 GOVQEKRSQZBPAX-UHFFFAOYSA-N 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 26
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
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- HSWPZIDYAHLZDD-UHFFFAOYSA-N atipamezole Chemical compound C1C2=CC=CC=C2CC1(CC)C1=CN=CN1 HSWPZIDYAHLZDD-UHFFFAOYSA-N 0.000 description 17
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- BPXINCHFOLVVSG-UHFFFAOYSA-N 9-chloroacridine Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=NC2=C1 BPXINCHFOLVVSG-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VWOJSRICSKDKAW-UHFFFAOYSA-N 1-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCNCC1 VWOJSRICSKDKAW-UHFFFAOYSA-N 0.000 description 7
- MOZNZNKHRXRLLF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1 MOZNZNKHRXRLLF-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 230000008485 antagonism Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- HRLIOXLXPOHXTA-NSHDSACASA-N dexmedetomidine Chemical compound C1([C@@H](C)C=2C(=C(C)C=CC=2)C)=CN=C[N]1 HRLIOXLXPOHXTA-NSHDSACASA-N 0.000 description 6
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- 238000001727 in vivo Methods 0.000 description 6
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- 239000000556 agonist Substances 0.000 description 5
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- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- GZNDUKANJZIZOT-UHFFFAOYSA-N 1-methyl-4-(4-nitrophenyl)piperazine Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C=C1 GZNDUKANJZIZOT-UHFFFAOYSA-N 0.000 description 4
- 102000012305 Alpha 2A adrenoceptor Human genes 0.000 description 4
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- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- RBNLMAXLHADNEU-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carbonitrile Chemical compound C1=CC=C2C(=O)C(C#N)=CNC2=C1 RBNLMAXLHADNEU-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
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- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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-
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20000480A FI20000480A0 (fi) | 2000-03-01 | 2000-03-01 | Kinoliini- ja naftaleenijohdannaisia alfa-2 antagonisteina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200206956B true ZA200206956B (en) | 2003-12-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200206956A ZA200206956B (en) | 2000-03-01 | 2002-08-29 | Derivatives of quinoline as alpha-2 antagonists. |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1263733A2 (fr) |
| JP (1) | JP2003525274A (fr) |
| KR (1) | KR20020089372A (fr) |
| CN (1) | CN1468224A (fr) |
| AR (1) | AR034249A1 (fr) |
| AU (1) | AU2001239331A1 (fr) |
| BR (1) | BR0108816A (fr) |
| CA (1) | CA2400657A1 (fr) |
| CZ (1) | CZ20022880A3 (fr) |
| EE (1) | EE200200490A (fr) |
| FI (1) | FI20000480A0 (fr) |
| HU (1) | HUP0204458A3 (fr) |
| IL (1) | IL151093A0 (fr) |
| MX (1) | MXPA02008402A (fr) |
| NO (1) | NO20024159D0 (fr) |
| PE (1) | PE20011084A1 (fr) |
| PL (1) | PL357874A1 (fr) |
| RU (1) | RU2002125944A (fr) |
| SK (1) | SK12332002A3 (fr) |
| WO (1) | WO2001064645A2 (fr) |
| ZA (1) | ZA200206956B (fr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1628109A (zh) * | 2002-02-05 | 2005-06-15 | 诺沃挪第克公司 | 新颖的芳基－与杂芳基－哌嗪 |
| ATE374773T1 (de) | 2002-04-03 | 2007-10-15 | Orion Corp | Polycyclische verbindungen als potenten alpha2- adrenoceptor antagonisten |
| WO2003082825A1 (fr) * | 2002-04-03 | 2003-10-09 | Orion Corporation | Utilisation de l'antagoniste d'un alfa2-adrenocepteur en cas de maladies du snc |
| AU2003224482A1 (en) * | 2002-04-30 | 2003-11-17 | Korea Research Institute Of Chemical Technology | Quinoline derivatives as caspase-3 inhibitor, preparation for producing the same and pharmaceutical composition comprising the same |
| WO2004067513A1 (fr) * | 2003-01-27 | 2004-08-12 | Oy Juvantia Pharma Ltd | Antagonistes pour recepteurs alpha-2 adrenergiques |
| CA2614116A1 (fr) | 2005-07-04 | 2007-01-11 | Novo Nordisk A/S | Medicaments |
| US8183239B2 (en) | 2005-10-31 | 2012-05-22 | Janssen Pharmaceutica Nv | Substituted piperazines and piperidines as modulators of the neuropeptide Y2 receptor |
| EP1968961A2 (fr) | 2005-12-21 | 2008-09-17 | Decode Genetics EHF | Inhibiteurs de biaryl-azote-heterocycle de lta4h pour traiter l'inflammation |
| RU2008150485A (ru) * | 2006-05-22 | 2010-06-27 | Янссен Фармацевтика Н.В. (Be) | Замещенные производные пиразинона для применения в качестве лекарственного средства |
| US8318927B2 (en) | 2006-05-23 | 2012-11-27 | High Point Pharmaceuticals, Llc | 6-(4-cyclopropylpiperazin-1-yl)-2′-methyl-[3, 4′]-bipyridine and its uses as a medicament |
| CN102295606A (zh) | 2006-05-29 | 2011-12-28 | 高点制药有限责任公司 | 合成3-（1，3-苯并间二氧杂环戊烯-5-基）-6-（4-环丙基哌嗪-1-基）-哒嗪的方法及其适用的中间体 |
| EP2014656A3 (fr) | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | Nouveaux antagonistes d'hétéocycliques h3 |
| TWI457122B (zh) | 2007-07-20 | 2014-10-21 | Orion Corp | 作為用於治療周邊和中央神經系統疾病之alpha2C拮抗劑的2,3－二氫苯並[1,4]戴奧辛－2－基甲基衍生物 |
| US8324213B2 (en) | 2008-10-07 | 2012-12-04 | Merck Sharp & Dohme Corp. | Biaryl-spiroaminooxazoline analogues as alpha 2C adrenergic receptor modulators |
| TW201024282A (en) | 2008-11-20 | 2010-07-01 | Orion Corp | New pharmaceutical compounds |
| MX2012006580A (es) * | 2009-12-11 | 2012-09-28 | Genecode As | Metodo para facilitar la sobrevivencia de celulas neurales usando mimeticos de ligandos (gfl) de la familia gdnf o activadores de la ruta de señalizacion de ret. |
| CN103524413B (zh) * | 2012-07-04 | 2016-04-20 | 江苏先声药物研究有限公司 | 氢化吖啶衍生物及其应用 |
| JOP20200052A1 (ar) * | 2013-12-19 | 2017-06-16 | Bayer Pharma AG | بيبريدينيل تتراهيدرو كوينولينات مستبدلة واستخدامها كمعضدات مستقبل أدريني ألفا- 2c |
| WO2015153535A1 (fr) | 2014-03-31 | 2015-10-08 | MiRx Pharmaceuticals, LLC | Nouveaux inhibiteurs hdmx et leur utilisation dans le traitement du cancer |
| WO2016135137A1 (fr) | 2015-02-23 | 2016-09-01 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Dérivés de 4-(phénylamino)quinoléine substitués en tant qu'inhibiteurs de mth1 pour la thérapie du cancer |
| WO2016135140A1 (fr) | 2015-02-23 | 2016-09-01 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Dérivés de 4-aminoquinazoline en tant qu'inhibiteurs de mth1 pour la thérapie du cancer |
| WO2016135139A1 (fr) | 2015-02-23 | 2016-09-01 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Dérivés de 2,3-dihydrocyclopenta[b]quinoléine en tant qu'inhibiteurs de mth1 pour la thérapie du cancer |
| WO2016135138A1 (fr) | 2015-02-23 | 2016-09-01 | Cemm - Forschungszentrum Für Molekulare Medizin Gmbh | Dérivés d'oxoquinoléine en tant qu'inhibiteurs de mth1 pour la thérapie du cancer |
| CN107337641B (zh) * | 2017-07-01 | 2020-04-28 | 广东医科大学 | 一种4-柔性胺基-2-芳乙烯基喹啉类衍生物及其制备方法和应用 |
| JP2024536926A (ja) * | 2021-09-07 | 2024-10-08 | ギズモ セラピューティクス インコーポレイテッド | グリコサミノグリカンとのアミロイドペプチド相互作用の阻害剤を含む化合物及び医薬組成物、治療の方法、並びにその使用 |
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| GB9510757D0 (en) * | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
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2000
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- 2001-02-28 AU AU2001239331A patent/AU2001239331A1/en not_active Abandoned
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- 2001-02-28 JP JP2001563488A patent/JP2003525274A/ja active Pending
- 2001-02-28 CZ CZ20022880A patent/CZ20022880A3/cs unknown
- 2001-02-28 CN CNA018059236A patent/CN1468224A/zh active Pending
- 2001-02-28 EP EP01913918A patent/EP1263733A2/fr not_active Withdrawn
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- 2001-02-28 RU RU2002125944/04A patent/RU2002125944A/ru not_active Application Discontinuation
- 2001-02-28 CA CA002400657A patent/CA2400657A1/fr not_active Abandoned
- 2001-02-28 EE EEP200200490A patent/EE200200490A/xx unknown
- 2001-02-28 HU HU0204458A patent/HUP0204458A3/hu unknown
- 2001-02-28 BR BR0108816-5A patent/BR0108816A/pt not_active Application Discontinuation
- 2001-02-28 KR KR1020027011453A patent/KR20020089372A/ko not_active Application Discontinuation
- 2001-02-28 IL IL15109301A patent/IL151093A0/xx unknown
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2002
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- 2002-08-30 NO NO20024159A patent/NO20024159D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20024159L (no) | 2002-08-30 |
| CA2400657A1 (fr) | 2001-09-07 |
| AU2001239331A1 (en) | 2001-09-12 |
| IL151093A0 (en) | 2003-04-10 |
| HUP0204458A3 (en) | 2004-07-28 |
| FI20000480A0 (fi) | 2000-03-01 |
| CZ20022880A3 (cs) | 2003-06-18 |
| KR20020089372A (ko) | 2002-11-29 |
| CN1468224A (zh) | 2004-01-14 |
| PL357874A1 (en) | 2004-07-26 |
| NO20024159D0 (no) | 2002-08-30 |
| AR034249A1 (es) | 2004-02-18 |
| PE20011084A1 (es) | 2001-10-25 |
| WO2001064645A3 (fr) | 2001-12-27 |
| EE200200490A (et) | 2003-12-15 |
| HUP0204458A2 (hu) | 2003-04-28 |
| MXPA02008402A (es) | 2003-10-14 |
| SK12332002A3 (sk) | 2003-07-01 |
| RU2002125944A (ru) | 2004-02-27 |
| WO2001064645A2 (fr) | 2001-09-07 |
| BR0108816A (pt) | 2002-12-10 |
| EP1263733A2 (fr) | 2002-12-11 |
| JP2003525274A (ja) | 2003-08-26 |
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