IT1307331B1 - New quinoline 4-carboxamide derivatives - have NK3 and/or NK2 binding activity, useful for treating respiratory, inflammatory gastrointestinal, renal and CNS disorders - Google Patents
New quinoline 4-carboxamide derivatives - have NK3 and/or NK2 binding activity, useful for treating respiratory, inflammatory gastrointestinal, renal and CNS disordersInfo
- Publication number
- IT1307331B1 IT1307331B1 ITMI961689A IT1307331B1 IT 1307331 B1 IT1307331 B1 IT 1307331B1 IT MI961689 A ITMI961689 A IT MI961689A IT 1307331 B1 IT1307331 B1 IT 1307331B1
- Authority
- IT
- Italy
- Prior art keywords
- alkyl
- amino
- mono
- optionally substituted
- ring
- Prior art date
Links
- 230000027455 binding Effects 0.000 title abstract 3
- LEWDKQKVAFOMPI-UHFFFAOYSA-N quinoline-4-carboxamide Chemical class C1=CC=C2C(C(=O)N)=CC=NC2=C1 LEWDKQKVAFOMPI-UHFFFAOYSA-N 0.000 title abstract 2
- 208000018522 Gastrointestinal disease Diseases 0.000 title 1
- 208000015114 central nervous system disease Diseases 0.000 title 1
- 230000002496 gastric effect Effects 0.000 title 1
- 230000002757 inflammatory effect Effects 0.000 title 1
- 208000017169 kidney disease Diseases 0.000 title 1
- 230000000241 respiratory effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 14
- 125000003545 alkoxy group Chemical group 0.000 abstract 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000006413 ring segment Chemical group 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- 125000004945 acylaminoalkyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 125000001485 cycloalkadienyl group Chemical group 0.000 abstract 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000002746 neurokinin 2 receptor antagonist Substances 0.000 abstract 1
- 239000002740 neurokinin 3 receptor antagonist Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- -1 sulphonamido Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Abstract
Quinoline 4-carboxamide derivatives of formula (I) and their salts and solvates are new. Ar = optionally substituted aryl or 5-7C cycloalkadienyl or an optionally substituted single or fused ring hetero-aromatic group; R = 1-6C alkyl, 3-7C cycloalkyl, 3-7C cycloalkylalkyl, optionally substituted Ph or Ph(1-6C alkyl), an optionally substituted 5-membered heteroaromatic ring containing up to four heteroatoms N or O, hydroxy(1-6C alkyl), amino(1-6C alkyl), 1-6C alkylaminoalkyl, di(1-6C alkyl)aminoalkyl, 1-6C acylaminoalkyl, 1-6C alkoxyalkyl, 1-6C alkylcarbonyl, carboxy, 1-6C alkoxycarbonyl, 1-6C alkoxycarbonyl-(1-6C alkyl), aminocarbonyl, 1-6C alkylaminocarbonyl, di(1-6C alkyl)-aminocarbonyl, halo(1-6C alkyl), or (CH2)p; p = 2 or 3 such that, taken with a C atom from Ar, a ring is formed; R1 = H or up to four of 1-6C alkyl, 1-6C alkenyl, aryl, 1-6C alkoxy, OH, halo, NO2, CN, carboxy, carboxamido, sulphonamido, 1-6C alkoxycarbonyl, CF3, acyloxy, phthalimido, NH2 or mono- or di-(1-6C alkyl)amino; R2 = O(CH2)nX or NHCONHY; X = alkyl (optionally substituted with one or two groups OH or NH2), carboxy, CN, 1-6C alkoxycarbonyl, aminocarbonyl, mono- or di-(1-6C alkyl)aminocarbonyl, amino(1-6C alkyl)aminocarbonyl or mono- or di(1-6C alkyl)amino(1-6C alkyl)aminocarbonyl; or X = NX1X2 or a C-linked single or fused ring heterocyclic group where any ring is an optionally unsaturated 5- to 6-membered ring containing 1 or 2 N atoms and optionally 1 or 2 additional heteroatoms N or O and where 1 or 2 ring atoms are optionally substituted with 1-6C alkyl, OH, NH2, mono- or bis-(1-6C alkyl)amino or oxo; X1, X2 = H, carboxyalkylcarbonyl, alkoxycarbonyl-alkylcarbonyl, alkylcarbonyl, arylcarbonyl, heteroaryl-carbonyl, aryl-(1-6C alkyl)carbonyl, heteroaryl(1-6C alkyl)carbonyl, amino-carbonyl, mono- or bis(1-6C alkyl)aminocarbonyl, amino(1-6C alkyl)carbonyl, mono- or bis(1-6C alkyl)amino(1-6C alkyl)carbonyl, a group COTCOT1 or a 5-9-membered single or fused-ring cycloalkyl group containing 1 or 2 N atoms and optionally containing 1 or 2 additional heteroatoms N or O, and where 1 or 2 of the ring atoms are optionally substituted with 1-6C alkyl and the ring is optionally fused to a benzene ring; (all aryl or heteroaryl groups are optionally substituted with up to 2 of OH, 1-6C alkoxy, hydroxy(1-6C alkyl), amino(1-6C alkyl), mono- or bis(1-6C alkyl)amino, mono- or bis(1-6C alkyl)amino(1-6C alkyl), amino(1-6C alkoxy), mono or bis(1-6C alkyl)amino(1-6C alkoxy), carboxy, 1-6C alkylcarbonyl, 1-6C alkoxycarbonyl, carboxy(1-6C alkyl), carboxy(1-6C alkoxy) and 1-6C alkylcarbonyl(1-6C alkoxy); any alkyl groups of hetero(1-6C alkyl) or aryl(1-6C alkyl) groups is optionally substituted with amino or mono- or bis(1-6C alkyl)amino; n = 0-7, provided that when X = NX1X2, n = 2-7 and X1 and X2 are not both H; R3 = 1-6C alkyl, 3-7C cycloalkyl, 4-7C cycloalkylalkyl; or optionally substituted aryl or single or fused ring aromatic heterocyclic group; T = 1-6C alkylene or 2-6C alkenylene; T1 = OH or 1-6C alkoxy; Y = 1-6C alkyl, aryl, aryl(1-3C alkyl) or (CH2)p'X3; p' = 1-4; X3 = carboxy, 1-6C alkoxycarbonyl or CONH(CH2)qNX4X5; q = 2-4; and X4, X5 = H, 1-6C alkyl or 1-6C alkylcarbonyl. Also claimed is a combined NK2/NK3 antagonist (A), having NK2/NK3 binding affinity ratio of 0.005-20 (preferably 0.1-10) or having equal binding affinities.
Priority Applications (35)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT96MI001689 IT1307331B1 (en) | 1996-08-02 | 1996-08-02 | New quinoline 4-carboxamide derivatives - have NK3 and/or NK2 binding activity, useful for treating respiratory, inflammatory gastrointestinal, renal and CNS disorders |
DE69634416T DE69634416T2 (en) | 1995-11-24 | 1996-11-22 | QUINOLINE DERIVATIVES |
PCT/EP1996/005203 WO1997021680A1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
CZ981579A CZ157998A3 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives, process of their preparation, pharmaceutical composition and use |
EP96941023A EP0876347B1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
AT96941023T ATE289994T1 (en) | 1995-11-24 | 1996-11-22 | QUINOLINE DERIVATIVES |
IL12452296A IL124522A0 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
SK667-98A SK66798A3 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivative, preparation method thereof, pharmaceutical composition containing the same and its use |
US09/077,151 US6277862B1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
CN96199753A CN1207730A (en) | 1995-11-24 | 1996-11-22 | Quinoline derivs. |
EA199800477A EA002124B1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
ES96941023T ES2236757T3 (en) | 1995-11-24 | 1996-11-22 | DERIVATIVES OF QUINOLINA. |
BR9611820A BR9611820A (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
JP9521658A JP2000501104A (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
AU10317/97A AU1031797A (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
CA002238298A CA2238298A1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
NZ500371A NZ500371A (en) | 1995-11-24 | 1996-11-22 | NK-2/NK-3 antagonists and their use in treating respiratory disease |
APAP/P/1998/001237A AP9801237A0 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives. |
TR1998/00924T TR199800924T2 (en) | 1995-11-24 | 1996-11-22 | Quinoline t�revleri. |
NZ323387A NZ323387A (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives having neurokinin antagonist activity, preparation and use thereof |
KR1019980703873A KR19990071597A (en) | 1995-11-24 | 1996-11-22 | Quinoline derivative |
PL96326967A PL326967A1 (en) | 1995-11-24 | 1996-11-22 | Quinoline derivatives |
TW085114500A TW353066B (en) | 1995-11-24 | 1996-11-23 | Arylquinoline-carboxamide derivatives and pharmaceutical compositions containing them |
ARP960105317A AR004972A1 (en) | 1995-11-24 | 1996-11-25 | QUINOLINE COMPOUND 4-CARBOXAMIDES N-SUBSTITUTED, A PROCEDURE FOR ITS PREPARATION, THE USE OF THE SAME FOR THE MANUFACTURE OF A MEDICINAL PRODUCT, A PHARMACEUTICAL COMPOSITION AND ANTAGONIST NK-2 / NK-3. |
UY24547A UY24547A1 (en) | 1996-08-02 | 1997-05-07 | PROCEDURE FOR PREPARING QUINOLINE DERIVATIVES |
DZ970089A DZ2241A1 (en) | 1996-08-02 | 1997-05-18 | New compounds. |
IDP971650A ID17399A (en) | 1996-08-02 | 1997-05-19 | NEW SENYAWA, SPECIALLY THE NEW CHINOLINA DERIVATES |
PE1997000392A PE69898A1 (en) | 1996-08-02 | 1997-05-20 | QUINOLINE DERIVATIVES |
MA24625A MA24590A1 (en) | 1996-08-02 | 1997-05-20 | PROCESS FOR THE PREPARATION OF NEW COMPOUNDS |
PE2001000478A PE20011273A1 (en) | 1996-08-02 | 1997-05-20 | QUINOLINE DERIVATIVES AS ANTAGONISTS OF NEUROQUININ NK-2 / NK-3 RECEPTORS |
UY24733A UY24733A1 (en) | 1995-11-24 | 1997-09-30 | NEW COMPOUNDS |
OA9800061A OA11010A (en) | 1995-11-24 | 1998-05-22 | Quinoline derivatives |
MX9804107A MX9804107A (en) | 1995-11-24 | 1998-05-22 | Quinoline derivatives. |
NO19982331A NO311212B1 (en) | 1995-11-24 | 1998-05-22 | Quinoline derivatives, their use and process for their preparation, and pharmaceutical compositions containing them |
BG102558A BG102558A (en) | 1995-11-24 | 1998-06-18 | Quinoline derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT96MI001689 IT1307331B1 (en) | 1996-08-02 | 1996-08-02 | New quinoline 4-carboxamide derivatives - have NK3 and/or NK2 binding activity, useful for treating respiratory, inflammatory gastrointestinal, renal and CNS disorders |
Publications (3)
Publication Number | Publication Date |
---|---|
ITMI961689A0 ITMI961689A0 (en) | 1996-08-02 |
ITMI961689A1 ITMI961689A1 (en) | 1998-02-02 |
IT1307331B1 true IT1307331B1 (en) | 2001-10-30 |
Family
ID=11374759
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IT96MI001689 IT1307331B1 (en) | 1995-11-24 | 1996-08-02 | New quinoline 4-carboxamide derivatives - have NK3 and/or NK2 binding activity, useful for treating respiratory, inflammatory gastrointestinal, renal and CNS disorders |
Country Status (6)
Country | Link |
---|---|
DZ (1) | DZ2241A1 (en) |
ID (1) | ID17399A (en) |
IT (1) | IT1307331B1 (en) |
MA (1) | MA24590A1 (en) |
PE (2) | PE20011273A1 (en) |
UY (1) | UY24547A1 (en) |
-
1996
- 1996-08-02 IT IT96MI001689 patent/IT1307331B1/en active
-
1997
- 1997-05-07 UY UY24547A patent/UY24547A1/en not_active IP Right Cessation
- 1997-05-18 DZ DZ970089A patent/DZ2241A1/en active
- 1997-05-19 ID IDP971650A patent/ID17399A/en unknown
- 1997-05-20 PE PE2001000478A patent/PE20011273A1/en not_active Application Discontinuation
- 1997-05-20 PE PE1997000392A patent/PE69898A1/en not_active Application Discontinuation
- 1997-05-20 MA MA24625A patent/MA24590A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
UY24547A1 (en) | 1997-10-13 |
PE20011273A1 (en) | 2002-02-23 |
ITMI961689A0 (en) | 1996-08-02 |
DZ2241A1 (en) | 2002-12-18 |
MA24590A1 (en) | 1999-04-01 |
ITMI961689A1 (en) | 1998-02-02 |
ID17399A (en) | 1997-12-24 |
PE69898A1 (en) | 1999-01-24 |
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