CA1054600A - Amino derivatives of imidazo (4,5-b) pyridines - Google Patents
Amino derivatives of imidazo (4,5-b) pyridinesInfo
- Publication number
- CA1054600A CA1054600A CA244416A CA244416A CA1054600A CA 1054600 A CA1054600 A CA 1054600A CA 244416 A CA244416 A CA 244416A CA 244416 A CA244416 A CA 244416A CA 1054600 A CA1054600 A CA 1054600A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- lower alkyl
- methyl
- compound
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 43
- 150000002431 hydrogen Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- -1 dimethylaminopropyl Chemical group 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002905 orthoesters Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 abstract description 2
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003874 central nervous system depressant Substances 0.000 abstract description 2
- 230000003834 intracellular effect Effects 0.000 abstract description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 125000004494 ethyl ester group Chemical group 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229940086542 triethylamine Drugs 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000001110 calcium chloride Substances 0.000 description 6
- 229910001628 calcium chloride Inorganic materials 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 125000001589 carboacyl group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- XBLVHTDFJBKJLG-UHFFFAOYSA-N nicotinic acid ethyl ester Natural products CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000011664 nicotinic acid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- GKCNAXFKWLOVMQ-UHFFFAOYSA-N ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(Cl)C([N+]([O-])=O)=C1Cl GKCNAXFKWLOVMQ-UHFFFAOYSA-N 0.000 description 2
- CXWFRWKSGNOTLZ-UHFFFAOYSA-N ethyl 4-(butylamino)-6-(ethylamino)-2-methyl-5-nitropyridine-3-carboxylate Chemical compound CCCCNC1=C(C(=O)OCC)C(C)=NC(NCC)=C1[N+]([O-])=O CXWFRWKSGNOTLZ-UHFFFAOYSA-N 0.000 description 2
- OGNMDWFQCQWWPZ-UHFFFAOYSA-N ethyl 6-amino-4-(butylamino)-2-methyl-5-nitropyridine-3-carboxylate Chemical compound CCCCNC1=C(C(=O)OCC)C(C)=NC(N)=C1[N+]([O-])=O OGNMDWFQCQWWPZ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000006201 parenteral dosage form Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- MTGIKTMXZFIZLS-UHFFFAOYSA-N 2,4-dichloro-6-methyl-3-nitropyridine Chemical compound CC1=CC(Cl)=C([N+]([O-])=O)C(Cl)=N1 MTGIKTMXZFIZLS-UHFFFAOYSA-N 0.000 description 1
- WBQPAPJYYJBTIC-UHFFFAOYSA-N 2-methyl-5-nitropyridine Chemical compound CC1=CC=C([N+]([O-])=O)[C]=N1 WBQPAPJYYJBTIC-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- TZAGBVHIUUFVCJ-UHFFFAOYSA-N 2047-49-6 Chemical compound OC(=O)C1=CN=CC([N+]([O-])=O)=C1 TZAGBVHIUUFVCJ-UHFFFAOYSA-N 0.000 description 1
- XLVJKDXPBUHZLA-UHFFFAOYSA-N 4-hydroxy-6-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=N1 XLVJKDXPBUHZLA-UHFFFAOYSA-N 0.000 description 1
- MWGNVABGPDAPPZ-UHFFFAOYSA-N 5-amino-4-(butylamino)-6-(ethylamino)-2-methylpyridine-3-carboxylic acid Chemical compound CCCCNC1=C(N)C(NCC)=NC(C)=C1C(O)=O MWGNVABGPDAPPZ-UHFFFAOYSA-N 0.000 description 1
- GDYTTWINDKVPNX-UHFFFAOYSA-N 5-amino-4-chloro-2-methyl-6-(methylamino)pyridine-3-carboxylic acid Chemical compound CNC1=NC(C)=C(C(O)=O)C(Cl)=C1N GDYTTWINDKVPNX-UHFFFAOYSA-N 0.000 description 1
- XJKVLRBIUQBWNI-UHFFFAOYSA-N 5-amino-6-(ethylamino)-2-methyl-4-(4-methylpiperazin-1-yl)pyridine-3-carboxylic acid Chemical compound CCNC1=NC(C)=C(C(O)=O)C(N2CCN(C)CC2)=C1N XJKVLRBIUQBWNI-UHFFFAOYSA-N 0.000 description 1
- RUKLJQGTIWBAGM-UHFFFAOYSA-N 6-[benzyl(ethyl)amino]-2-methyl-4-(4-methylpiperazin-1-yl)-5-nitropyridine-3-carboxylic acid Chemical compound N=1C(C)=C(C(O)=O)C(N2CCN(C)CC2)=C([N+]([O-])=O)C=1N(CC)CC1=CC=CC=C1 RUKLJQGTIWBAGM-UHFFFAOYSA-N 0.000 description 1
- SISUIJIIHXAOKY-UHFFFAOYSA-N 6-[benzyl(ethyl)amino]-4-chloro-2-methyl-5-nitropyridine-3-carboxylic acid Chemical compound N=1C(C)=C(C(O)=O)C(Cl)=C([N+]([O-])=O)C=1N(CC)CC1=CC=CC=C1 SISUIJIIHXAOKY-UHFFFAOYSA-N 0.000 description 1
- AIVVCZSBEQHXNN-UHFFFAOYSA-N 7-(butylamino)-3,5-dimethylimidazo[4,5-b]pyridine-6-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC2=C1N=CN2C AIVVCZSBEQHXNN-UHFFFAOYSA-N 0.000 description 1
- BSCWYPPGNQQMLO-UHFFFAOYSA-N 7-(butylamino)-5-methyl-1h-imidazo[4,5-b]pyridine-6-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC2=C1N=CN2 BSCWYPPGNQQMLO-UHFFFAOYSA-N 0.000 description 1
- RBPVEBXNXHDCTE-UHFFFAOYSA-N 7-(butylamino)-5-methyl-2-oxo-1,3-dihydroimidazo[4,5-b]pyridine-6-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC2=C1N=C(O)N2 RBPVEBXNXHDCTE-UHFFFAOYSA-N 0.000 description 1
- FSMGYVPZHCOCES-UHFFFAOYSA-N 7h-imidazo[4,5-b]pyridine-6-carboxylic acid Chemical compound C1C(C(=O)O)=CN=C2N=CN=C21 FSMGYVPZHCOCES-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002497 edematous effect Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- FZTPMPYSLHNWLI-UHFFFAOYSA-N ethyl 5,6-diamino-4-(butylamino)-2-methylpyridine-3-carboxylate Chemical compound CCCCNC1=C(N)C(N)=NC(C)=C1C(=O)OCC FZTPMPYSLHNWLI-UHFFFAOYSA-N 0.000 description 1
- GMKZMEQJKQEBFT-UHFFFAOYSA-N ethyl 5-amino-4-chloro-2-methyl-6-(methylamino)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(NC)C(N)=C1Cl GMKZMEQJKQEBFT-UHFFFAOYSA-N 0.000 description 1
- MJTVNDOTYWALAJ-UHFFFAOYSA-N ethyl 7-(butylamino)-2,5-dimethyl-1h-imidazo[4,5-b]pyridine-6-carboxylate Chemical compound CCCCNC1=C(C(=O)OCC)C(C)=NC2=C1N=C(C)N2 MJTVNDOTYWALAJ-UHFFFAOYSA-N 0.000 description 1
- JYIKFCJSIAUYKP-UHFFFAOYSA-N ethyl 7-chloro-3,5-dimethylimidazo[4,5-b]pyridine-6-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C2N(C)C=NC2=C1Cl JYIKFCJSIAUYKP-UHFFFAOYSA-N 0.000 description 1
- ZPUKLXNUBIBXFM-UHFFFAOYSA-N ethyl 7H-imidazo[4,5-b]pyridine-6-carboxylate Chemical compound C(C)OC(=O)C=1CC=2C(=NC1)N=CN2 ZPUKLXNUBIBXFM-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940095064 tartrate Drugs 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
- 230000000699 topical effect Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/548,325 US3996233A (en) | 1975-02-10 | 1975-02-10 | Amino derivatives of imidazo[4,5-b]pyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054600A true CA1054600A (en) | 1979-05-15 |
Family
ID=24188357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA244416A Expired CA1054600A (en) | 1975-02-10 | 1976-01-28 | Amino derivatives of imidazo (4,5-b) pyridines |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3996233A (enExample) |
| JP (1) | JPS51105092A (enExample) |
| CA (1) | CA1054600A (enExample) |
| DE (1) | DE2604748A1 (enExample) |
| FR (1) | FR2299867A1 (enExample) |
| GB (1) | GB1541692A (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4003908A (en) * | 1976-03-11 | 1977-01-18 | E. R. Squibb & Sons, Inc. | Derivatives of imidazo(4,5-b)pyridines |
| US4088654A (en) * | 1976-10-29 | 1978-05-09 | E. R. Squibb & Sons, Inc. | Derivatives of imidazo(4,5-b)pyridines |
| DE2927987A1 (de) * | 1979-07-11 | 1981-02-05 | Thomae Gmbh Dr K | Neue 2-alkoxyphenyl-imidazo eckige klammer auf 4,5-b eckige klammer zu pyridine, deren herstellung und deren verwendung als arzneimittel |
| EP0193329A3 (en) * | 1985-02-22 | 1987-08-19 | Beecham Group Plc | Pyrazolopyridines, their preparation and pharmaceutical compositions containing them |
| SE0301373D0 (sv) * | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Novel compounds |
| BRPI0512239A (pt) * | 2004-06-17 | 2008-02-19 | Wyeth Corp | processos para preparação de antagonistas de receptores de hormÈnios liberadores de gonatropina |
| BRPI0512261A (pt) | 2004-06-17 | 2008-02-26 | Wyeth Corp | antagonistas de receptor de hormÈnio liberador de gonadotropina |
| EP1814866A2 (en) * | 2004-11-23 | 2007-08-08 | Wyeth a Corporation of the State of Delaware | Gonadotropin releasing hormone receptor antagonists |
| US7582634B2 (en) * | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7538113B2 (en) * | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7534796B2 (en) * | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
| US20060189619A1 (en) * | 2005-02-24 | 2006-08-24 | Wyeth | 3-({4-[2-(4-Tert-butylphenyl)-1h-benzimidazol-4-yl]piperazin-1-yl}methyl)pyrido[2,3-b]]pyrazi ne compounds |
| US7531542B2 (en) * | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
| US7582636B2 (en) * | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1186504A (en) * | 1966-10-15 | 1970-04-02 | Fisons Pest Control Ltd | Substituted Heterocyclic Compounds |
| US3828057A (en) * | 1971-05-25 | 1974-08-06 | Squibb & Sons Inc | Amino derivatives of pyrazolopyridine ketones |
| BE787249A (fr) * | 1971-08-05 | 1973-02-05 | Squibb & Sons Inc | Derives amino d'acides pyrazolopyridine carboxyliques, leurs esters et les sels de ces composes, ainsi que leurs procedes de preparation |
| US3891660A (en) * | 1974-02-07 | 1975-06-24 | Squibb & Sons Inc | Derivatives of 1H-imidazo{8 4,5-c{9 pyridine-7-carboxylic acids and esters |
-
1975
- 1975-02-10 US US05/548,325 patent/US3996233A/en not_active Expired - Lifetime
-
1976
- 1976-01-28 CA CA244416A patent/CA1054600A/en not_active Expired
- 1976-02-06 GB GB4784/76A patent/GB1541692A/en not_active Expired
- 1976-02-06 DE DE19762604748 patent/DE2604748A1/de active Pending
- 1976-02-10 FR FR7603626A patent/FR2299867A1/fr active Granted
- 1976-02-10 JP JP51013825A patent/JPS51105092A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2299867A1 (fr) | 1976-09-03 |
| FR2299867B1 (enExample) | 1979-08-24 |
| DE2604748A1 (de) | 1976-08-19 |
| GB1541692A (en) | 1979-03-07 |
| US3996233A (en) | 1976-12-07 |
| JPS51105092A (enExample) | 1976-09-17 |
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