CA2351865A1 - Derives de quinoline-4-carboxamide utilises comme antagonistes des recepteurs nk-3 et nk-2 - Google Patents
Derives de quinoline-4-carboxamide utilises comme antagonistes des recepteurs nk-3 et nk-2 Download PDFInfo
- Publication number
- CA2351865A1 CA2351865A1 CA002351865A CA2351865A CA2351865A1 CA 2351865 A1 CA2351865 A1 CA 2351865A1 CA 002351865 A CA002351865 A CA 002351865A CA 2351865 A CA2351865 A CA 2351865A CA 2351865 A1 CA2351865 A1 CA 2351865A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- optionally substituted
- phenyl
- alkyl
- 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
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 title description 5
- 108010040716 Neurokinin-3 Receptors Proteins 0.000 title description 5
- 102100029409 Neuromedin-K receptor Human genes 0.000 title description 5
- 102100037342 Substance-K receptor Human genes 0.000 title description 3
- 239000002464 receptor antagonist Substances 0.000 title description 3
- 229940044551 receptor antagonist Drugs 0.000 title description 3
- LEWDKQKVAFOMPI-UHFFFAOYSA-N quinoline-4-carboxamide Chemical class C1=CC=C2C(C(=O)N)=CC=NC2=C1 LEWDKQKVAFOMPI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 316
- -1 cyano, carboxy Chemical group 0.000 claims abstract description 103
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 239000012453 solvate Substances 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 19
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000005518 carboxamido group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims abstract 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 238000011282 treatment Methods 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 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
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- 239000000126 substance Substances 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
- UHXUVDXVVNWPJA-UHFFFAOYSA-N n-(pyrrolidin-1-ylmethylidene)methanesulfonamide Chemical compound CS(=O)(=O)N=CN1CCCC1 UHXUVDXVVNWPJA-UHFFFAOYSA-N 0.000 claims description 4
- RTZLYHMXDDWBLO-UHFFFAOYSA-N n-methyl-1-pyrrolidin-1-ylmethanimine Chemical compound CN=CN1CCCC1 RTZLYHMXDDWBLO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- JKOROYFWCVXNMW-UHFFFAOYSA-N pyrrolidin-1-ylmethylidenecyanamide Chemical compound N#CN=CN1CCCC1 JKOROYFWCVXNMW-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
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- 238000003818 flash chromatography Methods 0.000 description 27
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- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 11
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- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
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- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- BSAAEEAUGZMUNT-UHFFFAOYSA-N methyl 3-(bromomethyl)-2-phenylquinoline-4-carboxylate Chemical compound N=1C2=CC=CC=C2C(C(=O)OC)=C(CBr)C=1C1=CC=CC=C1 BSAAEEAUGZMUNT-UHFFFAOYSA-N 0.000 description 9
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- 239000005557 antagonist Substances 0.000 description 7
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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Abstract
Cette invention se rapporte à un composé, ou un solvate ou sel de ce composé, représenté par la formule (I), où Ar représente un aryle éventuellement substitué ou un groupe cycloalkdiényle C¿5-7,? ou un groupe cycloalkyle C¿5-7? éventuellement substitué, ou un groupe hétérocyclique aromatique à anneaux simples ou condensés éventuellement substitué; R représente hydrogène, alkyle C¿1-6? linéaire ou ramifié, cycloalkyle C¿3-7?, cycloalkylalkyle C¿3-7?; R¿1? représente hydrogène ou jusqu'à 3 substituants optionnels choisis dans la liste des radicaux suivants: alkyle C¿1-6?, alcényle C¿1-6?, aryle, alcoxy C¿1-6?, hydroxy, halogène, nitro, cyano, carboxy, carboxamido, sulfonamido, alcoxycarbonyle C¿1-6?, trifluorométhyle, acyloxy, amino ou mono et di-alkylamino C¿1-6?; R¿2? représente une fraction (CH¿2?)¿n?-NY¿1?Y¿2?, où n est égal à un nombre entier compris entre 1 et 9, Y¿1? et Y¿2? sont choisis séparément parmi alkyle C¿1-6?, alkyle C¿1-6? substitué par hydroxy, alcoxy, alkylamino C¿1-6? ou bis (alkyle C¿1-6?)amino, cycloalkyle C3-6; azacycloalkyle C4-6, alcényle C¿1-6?; aryle ou aryle-alkyle C¿1-6?, où Y¿1? et Y¿2? forment avec l'atome d'azote auquel ils sont liés un groupe hétérocyclique à anneaux simples ou condensés liés par N éventuellement substitué; R¿3? représente alkyle C¿1-6? linéaire ou ramifié, cycloalkyle C¿3-7?, cycloalkylalkyle C¿4-7?, aryle éventuellement substitué ou un groupe hétérocyclique aromatique à anneaux simples ou condensés éventuellement substitué; et R¿4? représente hydrogène ou alkyle C¿1-6?; R¿5? représente hydrogène ou halogène. Cette invention se rapporte en outre à un procédé de préparation de ces composés, à une composition pharmaceutique comprenant ces composés et à l'utilisation de ces composés et de cette composition en médecine.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9825552.4A GB9825552D0 (en) | 1998-11-20 | 1998-11-20 | Novel compounds |
| GB9825553.2 | 1998-11-20 | ||
| GB9825552.4 | 1998-11-20 | ||
| GBGB9825553.2A GB9825553D0 (en) | 1998-11-20 | 1998-11-20 | Novel Compounds |
| PCT/EP1999/009115 WO2000031037A1 (fr) | 1998-11-20 | 1999-11-19 | Derives de quinoline-4-carboxamide utilises comme antagonistes des recepteurs nk-3 et nk-2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2351865A1 true CA2351865A1 (fr) | 2000-06-02 |
Family
ID=26314705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002351865A Abandoned CA2351865A1 (fr) | 1998-11-20 | 1999-11-19 | Derives de quinoline-4-carboxamide utilises comme antagonistes des recepteurs nk-3 et nk-2 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1131295A1 (fr) |
| JP (1) | JP2002530377A (fr) |
| KR (1) | KR20010075726A (fr) |
| CN (1) | CN1406225A (fr) |
| AR (2) | AR021354A1 (fr) |
| AU (1) | AU768708B2 (fr) |
| BR (1) | BR9915475A (fr) |
| CA (1) | CA2351865A1 (fr) |
| CO (1) | CO5150149A1 (fr) |
| HK (1) | HK1041257A1 (fr) |
| HU (1) | HUP0104959A3 (fr) |
| IL (1) | IL143137A0 (fr) |
| MX (1) | MXPA01005095A (fr) |
| NO (1) | NO20012473L (fr) |
| NZ (1) | NZ511777A (fr) |
| PL (1) | PL347721A1 (fr) |
| TR (1) | TR200101412T2 (fr) |
| WO (1) | WO2000031037A1 (fr) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7037922B1 (en) | 2000-03-10 | 2006-05-02 | Neurogen Corporation | Aryl fused 2,4-disubstituted pyridines: NK3 receptor ligands |
| EP1334089A1 (fr) * | 2000-11-13 | 2003-08-13 | GlaxoSmithKline S.p.A. | Derives de la quinoline en tant qu'antagonistes de nk-3 et nk-2 |
| GB0027701D0 (en) * | 2000-11-13 | 2000-12-27 | Smithkline Beecham Spa | Novel compounds |
| JP2004519432A (ja) * | 2000-11-28 | 2004-07-02 | グラクソスミスクライン・ソシエタ・ペル・アチオニ | 新規化合物 |
| GB0028964D0 (en) * | 2000-11-28 | 2001-01-10 | Smithkline Beecham Spa | Novel compounds |
| JP2004517082A (ja) * | 2000-11-28 | 2004-06-10 | グラクソスミスクライン・ソシエタ・ペル・アチオニ | Nk−3アンタゴニストとしてのキノリン誘導体 |
| NZ570181A (en) | 2001-04-10 | 2010-02-26 | Ortho Mcneil Janssen Pharm | 1,3,8-Triazaspiro[4.5]decan-4-one derivatives useful for the treatment of ORL-1 receptor mediated disorders |
| GB0109122D0 (en) * | 2001-04-11 | 2001-05-30 | Smithkline Beecham Spa | Novel compounds |
| JP2004525184A (ja) * | 2001-04-11 | 2004-08-19 | グラクソスミスクライン・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3−置換キノリン−4−カルボキサミド誘導体 |
| MY134211A (en) * | 2001-05-18 | 2007-11-30 | Smithkline Beecham Corp | Novel use |
| WO2004002484A1 (fr) * | 2002-06-26 | 2004-01-08 | Kyowa Hakko Kogyo Co., Ltd. | Inhibiteur de phosphodiesterase |
| EA009369B1 (ru) | 2002-09-09 | 2007-12-28 | Янссен Фармацевтика, Н.В. | Производные гидроксизамещенного 1,3,8-триазинспиро[4,5]декан-4-она, полезные для лечения расстройств, опосредованных orl-рецептором |
| GB0303086D0 (en) | 2003-02-11 | 2003-03-19 | Merck Sharp & Dohme | New compounds |
| JP2007521276A (ja) * | 2003-06-25 | 2007-08-02 | スミスクライン・ビーチャム・コーポレイション | Nk−2およびnk−3として用いるための4−カルボキサミドキノリン誘導体 |
| GB0419192D0 (en) | 2004-08-27 | 2004-09-29 | Merck Sharp & Dohme | Therapeutic agents |
| GB0425076D0 (en) * | 2004-11-12 | 2004-12-15 | Smithkline Beecham Corp | Novel compounds |
| GB0509405D0 (en) * | 2005-05-10 | 2005-06-15 | Merck Sharp & Dohme | Therapeutic compounds |
| EP1891012A2 (fr) * | 2005-06-03 | 2008-02-27 | AstraZeneca AB | Derives de quinoline utilises comme antagonistes de nk3 |
| GB0515580D0 (en) | 2005-07-29 | 2005-09-07 | Merck Sharp & Dohme | Therapeutic compounds |
| AR057130A1 (es) | 2005-09-21 | 2007-11-14 | Astrazeneca Ab | Quinolinas de alquilsulfoxido y una composicion farmaceutica |
| WO2007039123A2 (fr) * | 2005-09-22 | 2007-04-12 | Smithkline Beecham Corporation | Traitement combine |
| TW201018662A (en) * | 2005-12-12 | 2010-05-16 | Astrazeneca Ab | Alkylsulphonamide quinolines |
| EP2055705A4 (fr) * | 2006-07-31 | 2014-08-20 | Ono Pharmaceutical Co | Composé auquel un groupe cyclique est lié par une liaison spiro et son utilisation |
| MX2009005641A (es) | 2006-11-28 | 2009-06-05 | Janssen Pharmaceutica Nv | Sales de 3-(3-amino-2-(r)-hidroxi-propil)-1-(4-fluoro-fenil)-8-(8- metil-naftalen-1-ilmetil)-1,3,8-triaza-espiro[4,5]deca n-4-ona. |
| WO2008097976A1 (fr) * | 2007-02-09 | 2008-08-14 | Kalypsys, Inc. | Modulateurs hétérocycliques de tgr5 pour le traitement des maladies |
| CN101679430B (zh) | 2007-04-09 | 2013-12-25 | 詹森药业有限公司 | 用于治疗焦虑和抑郁症的作为orl-1受体的配体的1,3,8-三取代-1,3,8-三氮杂-螺[4.5]癸-4-酮衍生物 |
| JP5819397B2 (ja) * | 2010-03-23 | 2015-11-24 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーGlaxoSmithKline LLC | Trpv4拮抗薬 |
| AU2014255512A1 (en) | 2013-04-19 | 2015-11-12 | Astrazeneca Ab | A NK3 receptor antagonist compound (NK3RA) for use in a method for the treatment of polycystic ovary syndrome (PCOS) |
| WO2017072629A1 (fr) | 2015-10-29 | 2017-05-04 | Cadila Healthcare Limited | Combinaison pharmaceutique d'antagoniste du récepteur nk3 et de biguanides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2191352C (fr) * | 1994-05-27 | 2001-01-30 | Carlo Farina | Derives de quinoline utilises comme antagonistes du recepteur nk3 de la tachykinine |
| 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. |
| AU8209898A (en) * | 1997-05-23 | 1998-12-11 | Smithkline Beecham Spa | Quinoline-4-carboxamide derivatives as nk-2 and nk-3 receptor antagonists |
-
1999
- 1999-11-19 CA CA002351865A patent/CA2351865A1/fr not_active Abandoned
- 1999-11-19 AU AU17770/00A patent/AU768708B2/en not_active Ceased
- 1999-11-19 MX MXPA01005095A patent/MXPA01005095A/es unknown
- 1999-11-19 AR ARP990105926A patent/AR021354A1/es unknown
- 1999-11-19 WO PCT/EP1999/009115 patent/WO2000031037A1/fr not_active Ceased
- 1999-11-19 NZ NZ511777A patent/NZ511777A/en unknown
- 1999-11-19 CN CN99815753A patent/CN1406225A/zh active Pending
- 1999-11-19 CO CO99072805A patent/CO5150149A1/es unknown
- 1999-11-19 AR ARP990105927A patent/AR021355A1/es not_active Application Discontinuation
- 1999-11-19 PL PL99347721A patent/PL347721A1/xx unknown
- 1999-11-19 EP EP99961001A patent/EP1131295A1/fr not_active Withdrawn
- 1999-11-19 TR TR2001/01412T patent/TR200101412T2/xx unknown
- 1999-11-19 HK HK02101024.6A patent/HK1041257A1/zh unknown
- 1999-11-19 BR BR9915475-7A patent/BR9915475A/pt not_active IP Right Cessation
- 1999-11-19 IL IL14313799A patent/IL143137A0/xx unknown
- 1999-11-19 KR KR1020017006343A patent/KR20010075726A/ko not_active Withdrawn
- 1999-11-19 HU HU0104959A patent/HUP0104959A3/hu unknown
- 1999-11-19 JP JP2000583865A patent/JP2002530377A/ja active Pending
-
2001
- 2001-05-18 NO NO20012473A patent/NO20012473L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL347721A1 (en) | 2002-04-22 |
| IL143137A0 (en) | 2002-04-21 |
| AU768708B2 (en) | 2004-01-08 |
| TR200101412T2 (tr) | 2001-10-22 |
| WO2000031037A1 (fr) | 2000-06-02 |
| CN1406225A (zh) | 2003-03-26 |
| MXPA01005095A (es) | 2002-04-24 |
| AR021355A1 (es) | 2002-07-17 |
| BR9915475A (pt) | 2001-12-18 |
| HUP0104959A2 (hu) | 2002-04-29 |
| JP2002530377A (ja) | 2002-09-17 |
| AU1777000A (en) | 2000-06-13 |
| HUP0104959A3 (en) | 2003-01-28 |
| NZ511777A (en) | 2003-12-19 |
| CO5150149A1 (es) | 2002-04-29 |
| KR20010075726A (ko) | 2001-08-09 |
| EP1131295A1 (fr) | 2001-09-12 |
| AR021354A1 (es) | 2002-07-17 |
| HK1041257A1 (zh) | 2002-07-05 |
| NO20012473D0 (no) | 2001-05-18 |
| NO20012473L (no) | 2001-07-18 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |