SK75094A3 - Naphthyridine derivatives - Google Patents

Naphthyridine derivatives Download PDF

Info

Publication number: SK75094A3
Authority: SK; Slovakia
Prior art keywords: group; formula; alkyl; carbon atoms; hydrogen atom
Prior art date: 1991-12-23

Application number

SK750-94A

Other languages

English (en)

Slovak (sk)

Inventor

Bernard J Armitage

John G Bowen

Malcolm J Grossley

Ian M Hunneyball

Bruce W Leslie

Thomas K Miller

Michael Spowage

Original Assignee

Boots Co Plc

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.)

1991-12-23

Filing date

1992-12-12

Publication date

1995-04-12

1992-12-12 Application filed by Boots Co Plc filed Critical Boots Co Plc

1995-04-12 Publication of SK75094A3 publication Critical patent/SK75094A3/sk

Links

150000005054 naphthyridines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 188
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 94
125000000217 alkyl group Chemical group 0.000 claims abstract description 58
239000001257 hydrogen Substances 0.000 claims abstract description 53
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
238000000034 method Methods 0.000 claims abstract description 28
125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 19
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 19
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
125000003277 amino group Chemical group 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 7
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
125000005236 alkanoylamino group Chemical group 0.000 claims abstract description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 3
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract 3
125000005019 carboxyalkenyl group Chemical group 0.000 claims abstract 3
125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 claims abstract 2
-1 or C 1 -C 6 alkanoyl Chemical group 0.000 claims description 83
125000004432 carbon atom Chemical group C* 0.000 claims description 78
125000005843 halogen group Chemical group 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
238000010438 heat treatment Methods 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
239000007788 liquid Substances 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
239000002585 base Substances 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
208000025747 Rheumatic disease Diseases 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
239000000376 reactant Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
AQZNKLJRHSWVOV-UHFFFAOYSA-N ethyl 6-ethoxy-4-(4-methoxyanilino)-7-methyl-1,8-naphthyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2N=C(C)C(OCC)=CC2=C1NC1=CC=C(OC)C=C1 AQZNKLJRHSWVOV-UHFFFAOYSA-N 0.000 claims description 4
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 2
MFQRHPQDMCQXGL-UHFFFAOYSA-N 6-ethoxy-n-(4-methoxyphenyl)-7-methyl-1,8-naphthyridin-4-amine Chemical compound C1=CN=C2N=C(C)C(OCC)=CC2=C1NC1=CC=C(OC)C=C1 MFQRHPQDMCQXGL-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
239000011260 aqueous acid Substances 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
UXBIXOXDACBTDG-UHFFFAOYSA-N 1-adamantyl radical Chemical compound C1C(C2)CC3C[C]1CC2C3 UXBIXOXDACBTDG-UHFFFAOYSA-N 0.000 claims 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
KHVFTTVPXONUEK-UHFFFAOYSA-N 4-[(6-ethoxy-7-methyl-1,8-naphthyridin-4-yl)amino]-2,6-dimethylphenol Chemical compound C1=CN=C2N=C(C)C(OCC)=CC2=C1NC1=CC(C)=C(O)C(C)=C1 KHVFTTVPXONUEK-UHFFFAOYSA-N 0.000 claims 1
239000012380 dealkylating agent Substances 0.000 claims 1
150000003053 piperidines Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 122
239000003435 antirheumatic agent Substances 0.000 abstract description 6
125000004414 alkyl thio group Chemical group 0.000 abstract description 2
125000001589 carboacyl group Chemical group 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 5
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
125000002723 alicyclic group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 112
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 47
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
239000007787 solid Substances 0.000 description 29
238000003756 stirring Methods 0.000 description 28
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000004480 active ingredient Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
238000001914 filtration Methods 0.000 description 11
239000003208 petroleum Substances 0.000 description 11
238000010992 reflux Methods 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000009835 boiling Methods 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
239000005662 Paraffin oil Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000002775 capsule Substances 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
239000003826 tablet Substances 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
239000000843 powder Substances 0.000 description 7
206010039073 rheumatoid arthritis Diseases 0.000 description 7
239000000725 suspension Substances 0.000 description 7
AQSRRZGQRFFFGS-UHFFFAOYSA-N 2-methylpyridin-3-ol Chemical compound CC1=NC=CC=C1O AQSRRZGQRFFFGS-UHFFFAOYSA-N 0.000 description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
230000003628 erosive effect Effects 0.000 description 6
125000004494 ethyl ester group Chemical group 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
230000000670 limiting effect Effects 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
230000000699 topical effect Effects 0.000 description 6
239000003981 vehicle Substances 0.000 description 6
CGXLVFZJJOXEDF-UHFFFAOYSA-N 1,8-naphthyridine-3-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CN=C21 CGXLVFZJJOXEDF-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000010410 layer Substances 0.000 description 5
201000008482 osteoarthritis Diseases 0.000 description 5
230000009467 reduction Effects 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
BATUATIMONERQY-UHFFFAOYSA-N 5-ethoxy-6-methylpyridin-2-amine Chemical compound CCOC1=CC=C(N)N=C1C BATUATIMONERQY-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
206010003246 arthritis Diseases 0.000 description 4
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
235000019271 petrolatum Nutrition 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
HLTDBMHJSBSAOM-UHFFFAOYSA-N 2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CC=N1 HLTDBMHJSBSAOM-UHFFFAOYSA-N 0.000 description 3
ADHVKJKRZSDQSU-UHFFFAOYSA-N 5-chloro-3-ethoxy-2-methyl-1,8-naphthyridine Chemical compound C1=CN=C2N=C(C)C(OCC)=CC2=C1Cl ADHVKJKRZSDQSU-UHFFFAOYSA-N 0.000 description 3
YLWLDKVTAXTNDI-UHFFFAOYSA-N 6-ethoxy-7-methyl-1h-1,8-naphthyridin-4-one Chemical compound C1=CN=C2N=C(C)C(OCC)=CC2=C1O YLWLDKVTAXTNDI-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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241000699666 Mus <mouse, genus> Species 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
238000003556 assay Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000002702 enteric coating Substances 0.000 description 3
238000009505 enteric coating Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
239000000499 gel Substances 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000001802 infusion Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000002674 ointment Substances 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
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239000011780 sodium chloride Substances 0.000 description 3
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239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
YEVGPCAJXICMQD-UHFFFAOYSA-N methyl 5-chloro-1,8-naphthyridine-2-carboxylate Chemical compound ClC1=CC=NC2=NC(C(=O)OC)=CC=C21 YEVGPCAJXICMQD-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
244000005700 microbiome Species 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000001616 monocyte Anatomy 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
208000030194 mouth disease Diseases 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
ZLZZAXUKBHFTHA-UHFFFAOYSA-N n,n-diethyl-2-(4-nitrophenoxy)ethanamine Chemical compound CCN(CC)CCOC1=CC=C([N+]([O-])=O)C=C1 ZLZZAXUKBHFTHA-UHFFFAOYSA-N 0.000 description 1
FSRDUCSLELWORM-UHFFFAOYSA-N n-[4-(1-adamantyloxy)phenyl]-6-ethoxy-7-methyl-1,8-naphthyridin-4-amine;hydrochloride Chemical compound Cl.C1C(C2)CC(C3)CC2CC13OC(C=C1)=CC=C1NC1=C2C=C(OCC)C(C)=NC2=NC=C1 FSRDUCSLELWORM-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
229960001639 penicillamine Drugs 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
201000001245 periodontitis Diseases 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000006187 pill Substances 0.000 description 1
210000004180 plasmocyte Anatomy 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
208000002574 reactive arthritis Diseases 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000007944 soluble tablet Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000012306 spectroscopic technique Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
210000002437 synoviocyte Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 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
238000002560 therapeutic procedure Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
210000002303 tibia Anatomy 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000009466 transformation Effects 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
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/04—Ortho-condensed systems
- 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]

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Rheumatology (AREA)
Pharmacology & Pharmacy (AREA)
Pain & Pain Management (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK750-94A 1991-12-23 1992-12-12 Naphthyridine derivatives SK75094A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB919127252A GB9127252D0 (en)	1991-12-23	1991-12-23	Therapeutic agents
PCT/EP1992/002901 WO1993013097A1 (en)	1991-12-23	1992-12-12	Anti-rheumatic naphthyridine derivatives
CN93109454A CN1096784A (zh)	1991-12-23	1993-06-22	含取代4(5)-氨基-1,8-二氨杂萘的治疗剂

Publications (1)

Publication Number	Publication Date
SK75094A3 true SK75094A3 (en)	1995-04-12

Family

ID=36822317

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK750-94A SK75094A3 (en)	1991-12-23	1992-12-12	Naphthyridine derivatives

Country Status (22)

Country	Link
US (1)	US5464781A (2)
EP (1)	EP0618916B1 (2)
JP (1)	JP2527917B2 (2)
CN (1)	CN1096784A (2)
AT (1)	ATE171452T1 (2)
AU (1)	AU656832B2 (2)
BG (1)	BG98813A (2)
CA (1)	CA2125858A1 (2)
CZ (1)	CZ153594A3 (2)
DE (1)	DE69227125T2 (2)
FI (1)	FI943019A7 (2)
GB (1)	GB9127252D0 (2)
HR (1)	HRP921455A2 (2)
HU (1)	HUT66971A (2)
IL (1)	IL104169A0 (2)
IN (1)	IN174405B (2)
MX (1)	MX9207494A (2)
NO (1)	NO942376L (2)
NZ (1)	NZ246156A (2)
SI (1)	SI9200408A (2)
SK (1)	SK75094A3 (2)
WO (1)	WO1993013097A1 (2)

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GB9312891D0 (en) *	1993-06-22	1993-08-04	Boots Co Plc	Therapeutic agents
GB9318931D0 (en) *	1993-09-14	1993-10-27	Boots Co Plc	Therapeutic agents
GB9420168D0 (en) *	1994-10-06	1994-11-23	Boots Co Plc	Therapeutic agents
AR004010A1 (es)	1995-10-11	1998-09-30	Glaxo Group Ltd	Compuestos heterociclicos
KR100567649B1 (ko) *	1996-09-25	2006-04-05	아스트라제네카 유케이 리미티드	혈관 내피 성장 인자와 같은 성장 인자의 효과를 억제하는 퀴놀린 유도체
RS49779B (sr)	1998-01-12	2008-06-05	Glaxo Group Limited,	Biciklična heteroaromatična jedinjenja kao inhibitori protein tirozin kinaze
US6166069A (en) *	1998-05-12	2000-12-26	American Home Products Corporation	Phenyl oxo-acetic acids useful in the treatment of insulin resistance and hyperglycemia
ATE377597T1 (de)	1999-07-09	2007-11-15	Glaxo Group Ltd	Anilinochinazoline als protein-tyrosin- kinasehemmer
US6933299B1 (en)	1999-07-09	2005-08-23	Smithkline Beecham Corporation	Anilinoquinazolines as protein tyrosine kinase inhibitors
ES2267748T3 (es)	2000-04-07	2007-03-16	Astrazeneca Ab	Compuestos de quinazolina.
US6534656B2 (en) *	2001-05-31	2003-03-18	North Carolina State University	Short synthesis of pyridine-based pharmaceutical intermediates
JP2003329989A (ja) *	2002-03-06	2003-11-19	Nippon Telegr & Teleph Corp <Ntt>	光送信装置
GB0230018D0 (en)	2002-12-23	2003-01-29	Syngenta Ltd	Fungicides
US8309562B2 (en) *	2003-07-03	2012-11-13	Myrexis, Inc.	Compounds and therapeutical use thereof
NZ544472A (en)	2003-07-03	2009-04-30	Myriad Genetics Inc	Compounds and therapeutical use thereof
EA009994B1 (ru)	2003-12-23	2008-06-30	Пфайзер Инк.	Новые хинолиновые производные
US8258145B2 (en) *	2005-01-03	2012-09-04	Myrexis, Inc.	Method of treating brain cancer
CA2592900A1 (en)	2005-01-03	2006-07-13	Myriad Genetics Inc.	Nitrogen containing bicyclic compounds and therapeutical use thereof
ATE475660T1 (de) *	2005-12-21	2010-08-15	Abbott Lab	Antivirale verbindungen
TWI392676B (zh) *	2005-12-21	2013-04-11	Abbott Lab	抗病毒化合物、其製備方法及用途
US7915411B2 (en) *	2005-12-21	2011-03-29	Abbott Laboratories	Anti-viral compounds
EP1979348B1 (en) *	2005-12-21	2012-01-18	Abbott Laboratories	Anti-viral compounds
EP2345652A1 (en)	2005-12-21	2011-07-20	Abbott Laboratories	Antiviral compounds
US8236950B2 (en)	2006-12-20	2012-08-07	Abbott Laboratories	Anti-viral compounds
EP2291376A2 (en) *	2008-07-03	2011-03-09	Merck Patent GmbH	Naphthyridininones as aurora kinase inhibitors
EP2401275B1 (en)	2009-02-24	2013-07-24	Respiratorius AB	Naphthyridine derivatives having bronchodilating activity
WO2011063398A1 (en) *	2009-11-23	2011-05-26	Cylene Pharamaceuticals, Inc.	Polymorphs and salts of a kinase inhibitor
CA2792068A1 (en)	2010-04-02	2011-10-06	Senomyx, Inc.	Sweet flavor modifier

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US4466965A (en) *	1982-07-26	1984-08-21	American Hospital Supply Corporation	Phthalazine compounds, compositions and use
NO174506B (no) *	1984-10-30	1994-02-07	Usv Pharma Corp	Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser
EP0222839A4 (en) *	1985-05-17	1988-11-09	Univ Australian	ANTI-MALARIA COMPOUNDS.
JPS6368568A (ja) *	1986-09-10	1988-03-28	Otsuka Pharmaceut Factory Inc	ｐ−アミノフエノ−ル誘導体
DE3644825A1 (de) *	1986-12-31	1988-07-14	Basf Ag	Substituierte 1,8-naphthyridin-derivate und diese enthaltende fungizide
AU632461B2 (en) *	1987-07-22	1993-01-07	Schering Corporation	Bicyclic compounds, their use as pharmaceuticals, their preparation, and intermediates useful in their preparation
GB8804443D0 (en) *	1988-02-25	1988-03-23	Smithkline Beckman Intercredit	Compounds
US4978661A (en) *	1988-09-29	1990-12-18	Innocenzo Caruso	Use of 6-halo-4-quinolone compounds and pharmaceutical compositions thereof for the preparation of a medicament for the therapeutical application in rheumatoid arthritis
GR900100380A (el) *	1989-05-20	1991-10-10	Fisons Plc	Μέ?οδος παρασκευής αντι-φλεγμονωδών παραγώγων αμινοφενόλης.
AU634561B2 (en) *	1989-07-27	1993-02-25	Eli Lilly And Company	Naphthyridine derivatives
JP2988739B2 (ja) *	1990-04-16	1999-12-13	協和醗酵工業株式会社	１，８−ナフチリジン−２−オン誘導体
JP3157077B2 (ja) *	1994-02-16	2001-04-16	内山工業株式会社	ベアリングシール

1991
- 1991-12-23 GB GB919127252A patent/GB9127252D0/en active Pending
1992
- 1992-10-12 US US08/244,369 patent/US5464781A/en not_active Expired - Lifetime
- 1992-12-12 DE DE69227125T patent/DE69227125T2/de not_active Expired - Fee Related
- 1992-12-12 NZ NZ246156A patent/NZ246156A/en unknown
- 1992-12-12 AT AT93900052T patent/ATE171452T1/de not_active IP Right Cessation
- 1992-12-12 HU HU9401877A patent/HUT66971A/hu unknown
- 1992-12-12 CA CA002125858A patent/CA2125858A1/en not_active Abandoned
- 1992-12-12 CZ CZ941535A patent/CZ153594A3/cs unknown
- 1992-12-12 AU AU31587/93A patent/AU656832B2/en not_active Ceased
- 1992-12-12 WO PCT/EP1992/002901 patent/WO1993013097A1/en not_active Ceased
- 1992-12-12 SK SK750-94A patent/SK75094A3/sk unknown
- 1992-12-12 JP JP5511397A patent/JP2527917B2/ja not_active Expired - Fee Related
- 1992-12-12 EP EP93900052A patent/EP0618916B1/en not_active Expired - Lifetime
- 1992-12-17 IN IN758MA1992 patent/IN174405B/en unknown
- 1992-12-18 IL IL104169A patent/IL104169A0/xx unknown
- 1992-12-22 HR HR921455A patent/HRP921455A2/hr not_active Application Discontinuation
- 1992-12-22 MX MX9207494A patent/MX9207494A/es unknown
- 1992-12-22 SI SI19929200408A patent/SI9200408A/sl unknown
1993
- 1993-06-22 CN CN93109454A patent/CN1096784A/zh active Pending
1994
- 1994-05-31 BG BG98813A patent/BG98813A/bg unknown
- 1994-06-22 FI FI943019A patent/FI943019A7/fi not_active Application Discontinuation
- 1994-06-22 NO NO942376A patent/NO942376L/no unknown

Also Published As

Publication number	Publication date
MX9207494A (es)	1993-07-01
AU3158793A (en)	1993-07-28
SI9200408A (en)	1993-09-30
JPH07502280A (ja)	1995-03-09
CA2125858A1 (en)	1993-07-08
NZ246156A (en)	1996-01-26
HUT66971A (en)	1995-01-30
GB9127252D0 (en)	1992-02-19
EP0618916B1 (en)	1998-09-23
JP2527917B2 (ja)	1996-08-28
IL104169A0 (en)	1993-05-13
ATE171452T1 (de)	1998-10-15
BG98813A (bg)	1995-05-31
FI943019A0 (fi)	1994-06-22
DE69227125T2 (de)	1999-02-18
WO1993013097A1 (en)	1993-07-08
FI943019A7 (fi)	1994-06-22
HRP921455A2 (en)	1994-12-31
EP0618916A1 (en)	1994-10-12
CN1096784A (zh)	1994-12-28
HU9401877D0 (en)	1994-09-28
DE69227125D1 (de)	1998-10-29
NO942376L (no)	1994-06-22
US5464781A (en)	1995-11-07
NO942376D0 (2)	1994-06-22
IN174405B (2)	1994-11-26
AU656832B2 (en)	1995-02-16
CZ153594A3 (en)	1995-02-15

Publication	Publication Date	Title
SK75094A3 (en)	1995-04-12	Naphthyridine derivatives
US5780482A (en)	1998-07-14	Condensed 4-aminopyridines with antirheumatic activity
US5747486A (en)	1998-05-05	Thienopyridine or thienopyrimidine derivatives and their use
US4753951A (en)	1988-06-28	Condensed imidazopyridine derivatives useful as psychotropic agents
DE69524114T2 (de)	2002-07-18	Naphthyridinonderivate
UA74850C2 (en)	2006-02-15	Amide derivatives as nmda receptor antagonists
WO1999028320A1 (en)	1999-06-10	2-aryl-8-oxodihydropurine derivatives, process for producing the same, medicinal compositions containing the same, and intermediates thereof
SK280822B6 (sk)	2000-08-14	Imidazopyridíny, spôsob ich prípravy, farmaceutické prostriedky s ich obsahom a ich použitie
CZ374692A3 (en)	1993-08-11	Proteolytic enzymes inhibitors based on saccharin derivatives
CZ289573B6 (cs)	2002-02-13	Sacharinové deriváty, farmaceutický prostředek obsahující tyto deriváty a pouľití těchto sacharinových derivátů
JP4227197B2 (ja)	2009-02-18	１Ｈ―ピリド［３，４―ｂ］インドール―４―カルボキサミド誘導体、その製造および治療上の適用
HU198047B (en)	1989-07-28	Process for production of new condensated derivatives of pirrol and medical preparatives containing these compounds as active substances
EP0174858B1 (en)	1989-01-04	Isoindolinone derivatives, production and use thereof
NZ203217A (en)	1985-09-13	Pyridobenzodiazepinone derivatives and pharmaceutical compositions
US5102890A (en)	1992-04-07	Pyrrole derivatives, their preparation and pharmaceutical compositions which contain them
JPS6229585A (ja)	1987-02-07	エーテル化若しくはエステル化しうるジヒドロキシ基により位置２で置換された４―ｏｈキノリンカルボン酸の新規の誘導体、その製造方法、及び医薬としてのその使用
WO1995030676A1 (en)	1995-11-16	Antirheumatic 1-alkyl-4-hydroxy-3-(thien-3-yl) 1,8-naphthyridin-2(1h)-ones
JPH08225531A (ja)	1996-09-03	キノリンまたはキナゾリン誘導体を含んでなる医薬およびそれに用いる新規誘導体
WO1995007909A1 (en)	1995-03-23	Alkyl-1-alkyl-4-hydroxy-2-oxo-1,8-naphthyridine-3-carboxylates as anti-rheumatic agents
JPH11279157A (ja)	1999-10-12	バルビツール酸誘導体およびそれらからなる骨・軟骨疾患予防・治療薬
JPH04103572A (ja)	1992-04-06	４―フェニル―２―（１―ピペラジニル）ピリジン誘導体
SI9300584A (en)	1994-06-30	Therapeutic agents for treatment of obesity and affective disorders and processes for their preparation
JPH10503782A (ja)	1998-04-07	新規な５Ｈ−チアゾロ［３，２−ａ］ピリミジン−５−オン誘導体
JPH08225577A (ja)	1996-09-03	チエノピリジンまたはチエノピリミジン誘導体およびそれらを含んでなる医薬