CA2611060A1 - Quinoline derivatives as nk3 antagonists - Google Patents
Quinoline derivatives as nk3 antagonists Download PDFInfo
- Publication number
- CA2611060A1 CA2611060A1 CA002611060A CA2611060A CA2611060A1 CA 2611060 A1 CA2611060 A1 CA 2611060A1 CA 002611060 A CA002611060 A CA 002611060A CA 2611060 A CA2611060 A CA 2611060A CA 2611060 A1 CA2611060 A1 CA 2611060A1
- Authority
- CA
- Canada
- Prior art keywords
- 6alkyl
- cyanomethyl
- phenyl
- pharmaceutically
- disease
- 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.)
- Abandoned
Links
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 3
- 239000005557 antagonist Substances 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 238000000034 method Methods 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 26
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 20
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
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- NGIJJOHATIDYHC-UHFFFAOYSA-N 3-(cyanomethyl)-2-phenyl-n-(1-phenylpropyl)quinoline-4-carboxamide Chemical compound C=1C=CC=CC=1C(CC)NC(=O)C(C1=CC=CC=C1N=1)=C(CC#N)C=1C1=CC=CC=C1 NGIJJOHATIDYHC-UHFFFAOYSA-N 0.000 claims description 2
- HJPHSXDMFNIHNB-SANMLTNESA-N 3-(cyanomethyl)-n-[(s)-cyclopropyl-(3-fluorophenyl)methyl]-2-(3-fluorophenyl)quinoline-4-carboxamide Chemical compound FC1=CC=CC([C@@H](NC(=O)C=2C3=CC=CC=C3N=C(C=2CC#N)C=2C=C(F)C=CC=2)C2CC2)=C1 HJPHSXDMFNIHNB-SANMLTNESA-N 0.000 claims description 2
- DQJSYELBRVAASP-RUZDIDTESA-N methyl (2r)-2-[[3-(cyanomethyl)-2-phenylquinoline-4-carbonyl]amino]-2-phenylacetate Chemical compound N([C@@H](C(=O)OC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(CC#N)C=1C1=CC=CC=C1 DQJSYELBRVAASP-RUZDIDTESA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- ZLQPXWZKRCEEHM-QHCPKHFHSA-N 3-(cyanomethyl)-2-(3-fluorophenyl)-n-[(1s)-1-phenylpropyl]quinoline-4-carboxamide Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(CC#N)C=1C1=CC=CC(F)=C1 ZLQPXWZKRCEEHM-QHCPKHFHSA-N 0.000 claims 1
- UOUOEFBZRSHKCK-SFHVURJKSA-N 3-(cyanomethyl)-2-phenyl-n-[(1s)-1-phenylethyl]quinoline-4-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(=O)C(C1=CC=CC=C1N=1)=C(CC#N)C=1C1=CC=CC=C1 UOUOEFBZRSHKCK-SFHVURJKSA-N 0.000 claims 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
-
- 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
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P1/12—Antidiarrhoeals
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- 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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68741805P | 2005-06-03 | 2005-06-03 | |
| US60/687,418 | 2005-06-03 | ||
| PCT/SE2006/000630 WO2006130080A2 (en) | 2005-06-03 | 2006-05-30 | Quinoline derivatives as nk3 anatgonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2611060A1 true CA2611060A1 (en) | 2006-12-07 |
Family
ID=37482086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002611060A Abandoned CA2611060A1 (en) | 2005-06-03 | 2006-05-30 | Quinoline derivatives as nk3 antagonists |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20080200500A1 (https=) |
| EP (1) | EP1891012A2 (https=) |
| JP (1) | JP2008542367A (https=) |
| KR (1) | KR20080016591A (https=) |
| CN (1) | CN101189211A (https=) |
| AU (1) | AU2006253054A1 (https=) |
| CA (1) | CA2611060A1 (https=) |
| IL (1) | IL187410A0 (https=) |
| MX (1) | MX2007014831A (https=) |
| NO (1) | NO20080033L (https=) |
| WO (1) | WO2006130080A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008131779A1 (en) | 2007-04-26 | 2008-11-06 | H. Lundbeck A/S | Isoquinolinone derivatives as nk3 antagonists |
| US8173639B2 (en) | 2007-04-26 | 2012-05-08 | H. Lundbeck A/S | Isoquinolinone derivatives as NK3 antagonists |
| EA201170074A1 (ru) | 2008-06-23 | 2011-10-31 | Х. Лундбекк А/С | Изохинолиноновые производные в качестве антагонистов nk3 |
| US8242134B2 (en) | 2008-09-15 | 2012-08-14 | H. Lundbeck A/S | Isoquinolinone derivatives as NK3 antagonists |
| TW201016688A (en) | 2008-10-20 | 2010-05-01 | Lundbeck & Co As H | Isoquinolinone derivatives as NK3 antagonists |
| TW201143768A (en) | 2009-12-15 | 2011-12-16 | Lundbeck & Co As H | Pyridone derivatives as NK3 antagonists |
| TW201144311A (en) | 2010-03-12 | 2011-12-16 | Lundbeck & Co As H | Azaisoquionolinone derivatives as NK3 antagonists |
| EP3915560A1 (en) | 2014-06-25 | 2021-12-01 | Emory University | Methods of managing conditioned fear with neurokinin receptor antagonists |
| KR20160069683A (ko) | 2014-12-09 | 2016-06-17 | 백찬욱 | 콤비보트 및 그 제작 방법 |
| EP3704271B1 (en) | 2017-11-02 | 2026-01-28 | California Institute of Technology | Neurokinin antagonists and uses thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK282721B6 (sk) * | 1994-05-27 | 2002-11-06 | Smithkline Beecham S.P.A. | Nepeptidové NK3 antagonistické látky, spôsob ich výroby, farmaceutické prostriedky s ich obsahom a ich použitie |
| IT1270615B (it) * | 1994-07-14 | 1997-05-07 | Smithkline Beecham Farma | Uso di derivati di chinolina |
| AR004735A1 (es) * | 1995-11-24 | 1999-03-10 | Smithkline Beecham Spa | Quinoleina 4-amido sustituida, un procedimiento para su preparacion, una composicion farmaceutica que los contiene y el uso de los mismos para lapreparacion de un medicamento. |
| GB9524137D0 (en) * | 1995-11-24 | 1996-01-24 | Smithkline Beecham Spa | Novel compounds |
| EP0983262B1 (en) * | 1997-05-23 | 2003-07-09 | GlaxoSmithKline S.p.A. | Quinoline-4-carboxamide derivatives as nk-2 and nk-3 receptor antagonists |
| AP1201A (en) * | 1997-09-17 | 2003-09-01 | Smithkline Beecham Corp | Method for the synthesis of quinoline derivatives. |
| JP2002530377A (ja) * | 1998-11-20 | 2002-09-17 | スミスクライン・ビーチャム・ソシエタ・ペル・アチオニ | Ｎｋ−３およびｎｋ−２受容体アンタゴニストとしてのキノリン−４−カルボキシアミド誘導体 |
| DE60209362T2 (de) * | 2001-04-11 | 2006-10-26 | Glaxosmithkline S.P.A. | 3-substituierte chinolin-4-carbonsäureamidderivate als nk-3- und nk-2-rezeptorantagonisten |
| CN101282964A (zh) * | 2005-08-11 | 2008-10-08 | 阿斯利康(瑞典)有限公司 | 作为nk3受体调节剂的氧-吡啶基喹啉酰胺 |
| AR058051A1 (es) * | 2005-09-21 | 2008-01-23 | Astrazeneca Ab | Quinolinas de alquilnitrilo.proceso de obtencion y composiciones farmaceuticas. |
| EP1981882A4 (en) * | 2006-01-27 | 2009-11-18 | Astrazeneca Ab | QUINOLINES SUBSTITUTED BY AN AMIDE |
-
2006
- 2006-05-30 MX MX2007014831A patent/MX2007014831A/es not_active Application Discontinuation
- 2006-05-30 EP EP06747824A patent/EP1891012A2/en not_active Withdrawn
- 2006-05-30 JP JP2008514588A patent/JP2008542367A/ja active Pending
- 2006-05-30 AU AU2006253054A patent/AU2006253054A1/en not_active Abandoned
- 2006-05-30 KR KR1020077027965A patent/KR20080016591A/ko not_active Withdrawn
- 2006-05-30 US US11/914,583 patent/US20080200500A1/en not_active Abandoned
- 2006-05-30 WO PCT/SE2006/000630 patent/WO2006130080A2/en not_active Ceased
- 2006-05-30 CA CA002611060A patent/CA2611060A1/en not_active Abandoned
- 2006-05-30 CN CNA2006800196735A patent/CN101189211A/zh active Pending
-
2007
- 2007-11-15 IL IL187410A patent/IL187410A0/en unknown
-
2008
- 2008-01-03 NO NO20080033A patent/NO20080033L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007014831A (es) | 2008-02-15 |
| EP1891012A2 (en) | 2008-02-27 |
| US20080200500A1 (en) | 2008-08-21 |
| WO2006130080A3 (en) | 2007-01-25 |
| WO2006130080A2 (en) | 2006-12-07 |
| NO20080033L (no) | 2008-01-03 |
| CN101189211A (zh) | 2008-05-28 |
| KR20080016591A (ko) | 2008-02-21 |
| AU2006253054A1 (en) | 2006-12-07 |
| JP2008542367A (ja) | 2008-11-27 |
| IL187410A0 (en) | 2008-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20100531 |