SK66898A3 - Quinoline-4-carboxamide derivatives, their preparation and their use - Google Patents

Quinoline-4-carboxamide derivatives, their preparation and their use Download PDF

Info

Publication number: SK66898A3
Authority: SK; Slovakia
Prior art keywords: alkyl; formula; group; compound; quinoline
Prior art date: 1995-11-24

Application number

SK668-98A

Other languages

English (en)

Slovak (sk)

Inventor

Giuseppe A M Giardina

Mario Grugni

Luca F Raveglia

Carlo Farina

Original Assignee

Smithkline Beecham Spa

Priority date (The priority date 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 date listed.)

1995-11-24

Filing date

1996-11-22

Publication date

1998-12-02

1995-11-24 Priority claimed from ITMI952462 external-priority patent/IT1276171B1/it

1996-08-02 Priority claimed from IT96MI001688 external-priority patent/IT1307330B1/it

1996-11-22 Application filed by Smithkline Beecham Spa filed Critical Smithkline Beecham Spa

1998-12-02 Publication of SK66898A3 publication Critical patent/SK66898A3/sk

Links

LEWDKQKVAFOMPI-UHFFFAOYSA-N quinoline-4-carboxamide Chemical class C1=CC=C2C(C(=O)N)=CC=NC2=C1 LEWDKQKVAFOMPI-UHFFFAOYSA-N 0.000 title claims description 21
238000002360 preparation method Methods 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims abstract description 222
-1 cyano, carboxy Chemical group 0.000 claims abstract description 80
125000000217 alkyl group Chemical group 0.000 claims abstract description 48
150000003839 salts Chemical class 0.000 claims abstract description 39
239000012453 solvate Substances 0.000 claims abstract description 27
125000003118 aryl group Chemical group 0.000 claims abstract description 26
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 16
150000002367 halogens Chemical class 0.000 claims abstract description 16
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 11
125000001424 substituent group Chemical group 0.000 claims abstract description 11
125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 8
125000005842 heteroatom Chemical group 0.000 claims abstract description 8
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 6
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000004945 acylaminoalkyl group Chemical group 0.000 claims abstract description 3
125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims abstract description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
125000005518 carboxamido group Chemical group 0.000 claims abstract description 3
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
125000005544 phthalimido group Chemical group 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 35
125000004429 atom Chemical group 0.000 claims description 14
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000002837 carbocyclic group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
208000037920 primary disease Diseases 0.000 claims description 6
208000037921 secondary disease Diseases 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
239000013543 active substance Substances 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 12
125000003277 amino group Chemical group 0.000 abstract description 3
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract description 2
125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 abstract description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
125000006727 (C1-C6) alkenyl group Chemical group 0.000 abstract 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 195
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 148
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
235000019439 ethyl acetate Nutrition 0.000 description 73
239000000243 solution Substances 0.000 description 72
239000011541 reaction mixture Substances 0.000 description 63
239000000460 chlorine Substances 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
239000003480 eluent Substances 0.000 description 46
238000006243 chemical reaction Methods 0.000 description 43
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 43
239000000203 mixture Substances 0.000 description 41
238000005160 1H NMR spectroscopy Methods 0.000 description 40
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
239000000741 silica gel Substances 0.000 description 40
229910002027 silica gel Inorganic materials 0.000 description 40
238000003818 flash chromatography Methods 0.000 description 37
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
239000011734 sodium Substances 0.000 description 34
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
238000002844 melting Methods 0.000 description 26
230000008018 melting Effects 0.000 description 26
239000002904 solvent Substances 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
239000012043 crude product Substances 0.000 description 25
239000012044 organic layer Substances 0.000 description 25
229920006395 saturated elastomer Polymers 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 20
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
238000000921 elemental analysis Methods 0.000 description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
238000010992 reflux Methods 0.000 description 14
239000000047 product Substances 0.000 description 13
238000001816 cooling Methods 0.000 description 11
239000003208 petroleum Substances 0.000 description 11
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
125000006413 ring segment Chemical group 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
208000035475 disorder Diseases 0.000 description 9
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
ZSVACLAZDFXWQG-UHFFFAOYSA-N 3-methyl-2-phenylquinoline-4-carboxylic acid Chemical compound N1=C2C=CC=CC2=C(C(O)=O)C(C)=C1C1=CC=CC=C1 ZSVACLAZDFXWQG-UHFFFAOYSA-N 0.000 description 8
230000003197 catalytic effect Effects 0.000 description 8
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
ABPUPHVEUMCNPO-QFIPXVFZSA-N 3-(2-aminoethoxy)-2-phenyl-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(OCCN)C=1C1=CC=CC=C1 ABPUPHVEUMCNPO-QFIPXVFZSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
102000005962 receptors Human genes 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
239000002808 molecular sieve Substances 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000001665 trituration Methods 0.000 description 6
BIAVGWDGIJKWRM-FQEVSTJZSA-N 3-hydroxy-2-phenyl-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(O)C=1C1=CC=CC=C1 BIAVGWDGIJKWRM-FQEVSTJZSA-N 0.000 description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
101800002813 Neurokinin-B Proteins 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
201000010099 disease Diseases 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
108090000765 processed proteins & peptides Proteins 0.000 description 5
238000000746 purification Methods 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical compound C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 4
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
101001125071 Homo sapiens Neuromedin-K receptor Proteins 0.000 description 4
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NHXYSAFTNPANFK-HDMCBQFHSA-N Neurokinin B Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCSC)NC(=O)[C@@H](N)CC(O)=O)C1=CC=CC=C1 NHXYSAFTNPANFK-HDMCBQFHSA-N 0.000 description 4
102000046798 Neurokinin B Human genes 0.000 description 4
102100029409 Neuromedin-K receptor Human genes 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
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238000009835 boiling Methods 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
239000012458 free base Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
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AQFLVLHRZFLDDV-VIFPVBQESA-N (1s)-1-phenylpropan-1-amine Chemical compound CC[C@H](N)C1=CC=CC=C1 AQFLVLHRZFLDDV-VIFPVBQESA-N 0.000 description 3
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
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125000001624 naphthyl group Chemical group 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
230000007433 nerve pathway Effects 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
239000002746 neurokinin 2 receptor antagonist Substances 0.000 description 1
239000002740 neurokinin 3 receptor antagonist Substances 0.000 description 1
230000002981 neuropathic effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
CVXGFPPAIUELDV-UHFFFAOYSA-N phenacylazanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=CC=C1 CVXGFPPAIUELDV-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical group C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
235000021395 porridge Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
HGHPGHVNTQSTNM-UHFFFAOYSA-N quinolin-2-ylmethanamine Chemical class C1=CC=CC2=NC(CN)=CC=C21 HGHPGHVNTQSTNM-UHFFFAOYSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000011514 reflex Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000002000 scavenging effect Effects 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
108010016070 senktide Proteins 0.000 description 1
230000020341 sensory perception of pain Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000000392 somatic effect Effects 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
230000009870 specific binding Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
210000005070 sphincter Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229940071117 starch glycolate Drugs 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
239000002466 tachykinin receptor agonist Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
USDQHYUIPHSBOM-UHFFFAOYSA-N tert-butyl 3-methyl-2-phenylquinoline-4-carboxylate Chemical compound N1=C2C=CC=CC2=C(C(=O)OC(C)(C)C)C(C)=C1C1=CC=CC=C1 USDQHYUIPHSBOM-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000759 toxicological effect Toxicity 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
230000002455 vasospastic effect Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- 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
- A61P27/00—Drugs for disorders of the senses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Immunology (AREA)
Neurosurgery (AREA)
Pulmonology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK668-98A 1995-11-24 1996-11-22 Quinoline-4-carboxamide derivatives, their preparation and their use SK66898A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
ITMI952462 IT1276171B1 (it)	1995-11-24	1995-11-24	Derivati chinolinici
IT96MI001688 IT1307330B1 (it)	1996-08-02	1996-08-02	Derivati chinolinici
PCT/EP1996/005207 WO1997019926A1 (fr)	1995-11-24	1996-11-22	Nouveaux derives de quinoline-4-carboxamide, leur preparation et leur utilisation en tant qu'antagonistes des recepteurs des neurokinines 3 (nk-3) et des neurokinines 2 (nk-2)

Publications (1)

Publication Number	Publication Date
SK66898A3 true SK66898A3 (en)	1998-12-02

Family

ID=26331327

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK668-98A SK66898A3 (en)	1995-11-24	1996-11-22	Quinoline-4-carboxamide derivatives, their preparation and their use

Country Status (26)

Country	Link
US (1)	US20020068827A1 (fr)
EP (1)	EP1019377A1 (fr)
JP (1)	JP2000513325A (fr)
KR (1)	KR19990071598A (fr)
CN (1)	CN1207729A (fr)
AP (1)	AP9801238A0 (fr)
AR (1)	AR004735A1 (fr)
AU (1)	AU1031897A (fr)
BG (1)	BG102557A (fr)
BR (1)	BR9611757A (fr)
CA (1)	CA2238328A1 (fr)
CZ (1)	CZ158098A3 (fr)
DZ (1)	DZ2128A1 (fr)
EA (1)	EA001771B1 (fr)
HU (1)	HUP9901016A3 (fr)
IL (1)	IL124418A0 (fr)
MA (1)	MA24011A1 (fr)
MX (1)	MX9804108A (fr)
NO (1)	NO311213B1 (fr)
OA (1)	OA11011A (fr)
PL (1)	PL326928A1 (fr)
SK (1)	SK66898A3 (fr)
TR (1)	TR199800883T2 (fr)
TW (1)	TW409123B (fr)
UY (2)	UY24375A1 (fr)
WO (1)	WO1997019926A1 (fr)

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US6780875B2 (en) *	1998-11-20	2004-08-24	Smithkline Beecham S.P.A.	Quinoline-4-carboxamide derivatives as NK-3 and NK-2 receptor antagonists
CN1406225A (zh) *	1998-11-20	2003-03-26	葛兰素史密丝克莱恩有限公司	用作nk－3和nk－2受体拮抗剂的喹啉－4－甲酰胺衍生物
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WO2000058313A1 (fr)	1999-03-29	2000-10-05	Neurogen Corporation	Derives de quinoline 4-substitues en tant que ligands des recepteurs de gaba
AU4802500A (en)	1999-04-26	2000-11-10	Neurogen Corporation	2-aminoquinolinecarboxamides: neurokinin receptor ligands
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SE0302139D0 (sv) *	2003-07-28	2003-07-28	Astrazeneca Ab	Novel compounds
GB0318727D0 (en) *	2003-08-08	2003-09-10	Smithkline Beecham Corp	Novel compounds
GB0425077D0 (en) *	2004-11-12	2004-12-15	Smithkline Beecham Corp	Novel compounds
AU2006253054A1 (en) *	2005-06-03	2006-12-07	Astrazeneca Ab	Quinoline derivatives as NK3 anatgonists
AU2006259890A1 (en) *	2005-06-23	2006-12-28	Astrazeneca Ab	Quinoline 3 -sulfonate esters as NK3 receptor modulators
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EP1915363A1 (fr) *	2005-08-11	2008-04-30	AstraZeneca AB	Modulateurs récépteurs nk3 en tant qu'amides de quinoléine oxopyridyl
JP2009504641A (ja) *	2005-08-11	2009-02-05	アストラゼネカ・アクチエボラーグ	Ｎｋ−３受容体の調節剤としてのアルキルピリジルキノリン
AR057130A1 (es)	2005-09-21	2007-11-14	Astrazeneca Ab	Quinolinas de alquilsulfoxido y una composicion farmaceutica
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WO2008114002A1 (fr)	2007-03-22	2008-09-25	Astrazeneca Ab	Dérivés de quinoléine destinés au traitement de maladies inflammatoires
US8106073B2 (en)	2007-11-30	2012-01-31	Astrazeneca Ab	Quinoline derivatives 057
CN102924375B (zh) *	2012-06-21	2015-02-18	江苏恩华药业股份有限公司	Talnetant中间体及其制备方法和应用
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1996
- 1996-11-21 AR ARP960105282A patent/AR004735A1/es unknown
- 1996-11-22 EP EP96941025A patent/EP1019377A1/fr not_active Withdrawn
- 1996-11-22 AU AU10318/97A patent/AU1031897A/en not_active Abandoned
- 1996-11-22 SK SK668-98A patent/SK66898A3/sk unknown
- 1996-11-22 MA MA24399A patent/MA24011A1/fr unknown
- 1996-11-22 TR TR1998/00883T patent/TR199800883T2/xx unknown
- 1996-11-22 CZ CZ981580A patent/CZ158098A3/cs unknown
- 1996-11-22 HU HU9901016A patent/HUP9901016A3/hu unknown
- 1996-11-22 IL IL12441896A patent/IL124418A0/xx unknown
- 1996-11-22 PL PL96326928A patent/PL326928A1/xx unknown
- 1996-11-22 JP JP09520158A patent/JP2000513325A/ja active Pending
- 1996-11-22 BR BR9611757A patent/BR9611757A/pt unknown
- 1996-11-22 EA EA199800538A patent/EA001771B1/ru not_active IP Right Cessation
- 1996-11-22 UY UY24375A patent/UY24375A1/es not_active IP Right Cessation
- 1996-11-22 CN CN96199747A patent/CN1207729A/zh active Pending
- 1996-11-22 WO PCT/EP1996/005207 patent/WO1997019926A1/fr not_active Ceased
- 1996-11-22 KR KR1019980703874A patent/KR19990071598A/ko not_active Withdrawn
- 1996-11-22 CA CA002238328A patent/CA2238328A1/fr not_active Abandoned
- 1996-11-22 AP APAP/P/1998/001238A patent/AP9801238A0/en unknown
- 1996-11-23 DZ DZ960173A patent/DZ2128A1/fr active
- 1996-11-23 TW TW085114501A patent/TW409123B/zh not_active IP Right Cessation
1997
- 1997-05-16 UY UY24555A patent/UY24555A1/es not_active Application Discontinuation
1998
- 1998-05-22 MX MX9804108A patent/MX9804108A/es unknown
- 1998-05-22 OA OA9800062A patent/OA11011A/en unknown
- 1998-05-22 NO NO19982333A patent/NO311213B1/no not_active IP Right Cessation
- 1998-06-18 BG BG102557A patent/BG102557A/bg unknown
2001
- 2001-11-26 US US09/994,402 patent/US20020068827A1/en not_active Abandoned

Also Published As

Publication number	Publication date
CZ158098A3 (cs)	1998-10-14
TW409123B (en)	2000-10-21
PL326928A1 (en)	1998-11-09
NO982333L (no)	1998-07-22
CN1207729A (zh)	1999-02-10
NO311213B1 (no)	2001-10-29
UY24375A1 (es)	1997-05-22
AR004735A1 (es)	1999-03-10
AU1031897A (en)	1997-06-19
HUP9901016A3 (en)	2002-01-28
EP1019377A1 (fr)	2000-07-19
AP9801238A0 (en)	1998-06-30
BG102557A (bg)	1999-03-31
US20020068827A1 (en)	2002-06-06
MA24011A1 (fr)	1997-07-01
UY24555A1 (es)	2001-04-30
OA11011A (en)	2003-03-06
KR19990071598A (ko)	1999-09-27
EA199800538A1 (ru)	1998-12-24
JP2000513325A (ja)	2000-10-10
TR199800883T2 (xx)	2000-12-21
DZ2128A1 (fr)	2002-10-26
EA001771B1 (ru)	2001-08-27
MX9804108A (es)	1998-09-30
NO982333D0 (no)	1998-05-22
CA2238328A1 (fr)	1997-06-05
IL124418A0 (en)	1998-12-06
HUP9901016A2 (hu)	2000-03-28
WO1997019926A1 (fr)	1997-06-05
BR9611757A (pt)	1999-04-06

Publication	Publication Date	Title
US20020068827A1 (en)	2002-06-06	Quinoline-4-carboxamide derivatives, their preparation and their use as neurokinin 3 ( NK-3 ) - and neurokinin 2 ( NK-3 ) receptor antagonists
US6277862B1 (en)	2001-08-21	Quinoline derivatives
JP2002530377A (ja)	2002-09-17	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
SK159299A3 (en)	2000-06-12	Quinoline-4-carboxamide derivatives as nk-2 and nk-3 receptor antagonists
ES2254688T3 (es)	2006-06-16	Derivados de quinolina-4-carboxamida como antagonistas de los receptores nk-3 y nk-2.
JP2004529145A (ja)	2004-09-24	新規化合物
US20040077658A1 (en)	2004-04-22	Quinoline-4-carboxamide derivatives as nk-3 and nk-2 receptor antagonists
JP2002530378A (ja)	2002-09-17	Ｎｋ−２およびｎｋ−３受容体リガンドとしてのキノリン誘導体
JP2004517062A (ja)	2004-06-10	Ｎｋ−３およびｎｋ−２アンタゴニストとしてのキノリン誘導体
JP2004517079A (ja)	2004-06-10	新規化合物
JP2004519432A (ja)	2004-07-02	新規化合物
AU757836B2 (en)	2003-03-06	Quinoline derivatives
Luca et al.	0	PCT WORLD) INTELLECTUAL PROPERTY ORGANIZATION
JP2006516632A (ja)	2006-07-06	Ｎｋ−２およびｎｋ−３受容体アンタゴニストとしてのキノリン誘導体
AU4263200A (en)	2000-11-30	Quinoline-4-carboxamide derivatives, their preparation and their use as neurokinin 3 (NK-3)- and neurokinin 2 (NK-2) receptor antagonists
CZ416199A3 (cs)	2000-08-16	Chinolin-4-karboxamidové deriváty jako antagonisté receptoru pro NK-2 a NK-3
KR20010012823A (ko)	2001-02-26	Ｎｋ-2 및 ｎｋ-3 수용체 길항제로서의퀴놀린-4-카르복스아미드 유도체
US20040097518A1 (en)	2004-05-20	Quinoline derivatives as nk-3 antagonists
HUP9903427A2 (hu)	2000-02-28	Kinolinszármazékok, eljárás előállításukra, valamint a vegyületeket tartalmazó gyógyszerkészítmények
NZ500371A (en)	2001-08-31	NK-2/NK-3 antagonists and their use in treating respiratory disease
AU1031797A (en)	1997-07-03	Quinoline derivatives
ITMI972352A1 (it)	1999-04-17	Derivati chinolinici, procedimento per la loro preparazione e uso come antagonisti del recettore nk3
ITMI961688A1 (it)	1998-02-02	Derivati chinolinici