CN1216865C - 制备2－苯基－3－氨基吡啶、其取代的苯基衍生物和其盐的方法 - Google Patents

制备2－苯基－3－氨基吡啶、其取代的苯基衍生物和其盐的方法 Download PDF

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Publication number: CN1216865C
Authority: CN; China
Prior art keywords: alkyl; compound; formula; phenyl; aryl
Prior art date: 1999-05-17
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 - Fee Related

Application number

CN001064517A

Other languages

English (en)

Chinese (zh)

Other versions

CN1288005A (zh

Inventor

塔米姆·F·布雷什

斯蒂芬·卡伦

迈克尔·J·卡斯塔尔迪

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

Original Assignee

Pfizer Products Inc

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.)

1999-05-17

Filing date

2000-04-07

Publication date

2005-08-31

2000-04-07 Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc

2001-03-21 Publication of CN1288005A publication Critical patent/CN1288005A/zh

2005-08-31 Application granted granted Critical

2005-08-31 Publication of CN1216865C publication Critical patent/CN1216865C/zh

2020-04-07 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 21
150000003839 salts Chemical class 0.000 title claims abstract description 21
238000000034 method Methods 0.000 title claims description 32
XTHJCITVHCRQRD-UHFFFAOYSA-N 2-phenylpyridin-3-amine Chemical compound NC1=CC=CN=C1C1=CC=CC=C1 XTHJCITVHCRQRD-UHFFFAOYSA-N 0.000 title abstract description 25
150000001875 compounds Chemical class 0.000 claims abstract description 71
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 26
238000006243 chemical reaction Methods 0.000 claims abstract description 19
239000003054 catalyst Substances 0.000 claims abstract description 13
239000012442 inert solvent Substances 0.000 claims abstract description 13
229910052763 palladium Inorganic materials 0.000 claims abstract description 13
239000011260 aqueous acid Substances 0.000 claims abstract description 5
-1 methoxyl group Chemical group 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 32
239000003513 alkali Substances 0.000 claims description 18
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 10
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
239000007810 chemical reaction solvent Substances 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
239000005864 Sulphur Substances 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 2
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
238000004519 manufacturing process Methods 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
239000005557 antagonist Substances 0.000 description 13
239000000203 mixture Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 description 12
201000010099 disease Diseases 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
235000017550 sodium carbonate Nutrition 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
239000003814 drug Substances 0.000 description 7
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
229910000073 phosphorus hydride Inorganic materials 0.000 description 6
238000010992 reflux Methods 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 5
208000019901 Anxiety disease Diseases 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
235000015320 potassium carbonate Nutrition 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
102000003141 Tachykinin Human genes 0.000 description 3
206010047700 Vomiting Diseases 0.000 description 3
230000036506 anxiety Effects 0.000 description 3
238000005660 chlorination reaction Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 3
125000003963 dichloro group Chemical group Cl* 0.000 description 3
239000000539 dimer Substances 0.000 description 3
125000001183 hydrocarbyl group Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
KWZIDENWDCKKPW-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)acetamide Chemical compound CC(=O)NC1=CC=CN=C1Cl KWZIDENWDCKKPW-UHFFFAOYSA-N 0.000 description 3
NTAJAEPMBORQGY-UHFFFAOYSA-N n-(2-phenylpyridin-3-yl)acetamide;hydrochloride Chemical compound Cl.CC(=O)NC1=CC=CN=C1C1=CC=CC=C1 NTAJAEPMBORQGY-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
229910000105 potassium hydride Inorganic materials 0.000 description 3
239000003826 tablet Substances 0.000 description 3
108060008037 tachykinin Proteins 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
230000008673 vomiting Effects 0.000 description 3
QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 2
WUUPIONDVKXCBK-UHFFFAOYSA-N 2-phenylpyridin-3-amine;hydrochloride Chemical compound Cl.NC1=CC=CN=C1C1=CC=CC=C1 WUUPIONDVKXCBK-UHFFFAOYSA-N 0.000 description 2
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LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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208000002193 Pain Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
102100024304 Protachykinin-1 Human genes 0.000 description 2
101800003906 Substance P Proteins 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
206010042496 Sunburn Diseases 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
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238000007918 intramuscular administration Methods 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 1
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125000006017 1-propenyl group Chemical group 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
GFMAFYNUQDLPBP-UHFFFAOYSA-N 2-phenylpiperidin-3-amine Chemical compound NC1CCCNC1C1=CC=CC=C1 GFMAFYNUQDLPBP-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
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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
- 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)

CN001064517A 1999-05-17 2000-04-07 制备2－苯基－3－氨基吡啶、其取代的苯基衍生物和其盐的方法 Expired - Fee Related CN1216865C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13455999P	1999-05-17	1999-05-17
US60/134,559		1999-05-17

Publications (2)

Publication Number	Publication Date
CN1288005A CN1288005A (zh)	2001-03-21
CN1216865C true CN1216865C (zh)	2005-08-31

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Country Status (25)

Country	Link
US (1)	US6316632B1 (2)
EP (1)	EP1054002B1 (2)
JP (1)	JP3837011B2 (2)
KR (1)	KR100386226B1 (2)
CN (1)	CN1216865C (2)
AR (1)	AR020029A1 (2)
AT (1)	ATE306474T1 (2)
AU (1)	AU775947B2 (2)
BR (1)	BR0001773A (2)
CA (1)	CA2308817C (2)
CZ (1)	CZ299474B6 (2)
DE (1)	DE60023063T2 (2)
DK (1)	DK1054002T3 (2)
ES (1)	ES2248017T3 (2)
HU (1)	HUP0001928A3 (2)
ID (1)	ID26061A (2)
IL (1)	IL136105A (2)
IN (1)	IN192341B (2)
MX (1)	MXPA00004790A (2)
PL (1)	PL198153B1 (2)
RS (1)	RS49964B (2)
RU (1)	RU2181120C2 (2)
TR (1)	TR200001403A2 (2)
TW (1)	TWI286133B (2)
ZA (1)	ZA200002375B (2)

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JP7673064B2 (ja)	2019-11-15	2025-05-08	カンディーセラピューティクスリミテッド	Ｎｔ－８１４の重要な中間体である６－クロロ－４－（４－フルオロ－２－メチルフェニル）ピリジン－３－アミンを作製するための新規な化学的方法

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US5232929A (en) *	1990-11-28	1993-08-03	Pfizer Inc.	3-aminopiperidine derivatives and related nitrogen containing heterocycles and pharmaceutical compositions and use
US5364943A (en) *	1991-11-27	1994-11-15	Pfizer Inc.	Preparation of substituted piperidines
JPH0794439B2 (ja) *	1990-05-31	1995-10-11	フアイザー・インコーポレイテツド	置換ピペリジンの製造法
JPH0794440B2 (ja)	1991-03-26	1995-10-11	フアイザー・インコーポレイテツド	置換ピペリジンの立体選択的製造
HU224443B1 (hu)	1991-06-20	2005-09-28	Pfizer Inc.	Fluor-alkoxi-benzaldehid-származékok
JP3042894B2 (ja)	1995-07-07	2000-05-22	ファイザー製薬株式会社	サブスタンスｐアンタゴニストとしての置換ベンゾラクタム化合物
TW340842B (en)	1995-08-24	1998-09-21	Pfizer	Substituted benzylaminopiperidine compounds
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TW426667B (en)	1997-11-19	2001-03-21	Pfizer	Piperidinylaminomethyl trifluoromethyl cyclic ether compounds as substance P antagonists

2000
- 2000-04-03 RS YUP-196/00A patent/RS49964B/sr unknown
- 2000-04-07 CN CN001064517A patent/CN1216865C/zh not_active Expired - Fee Related
- 2000-04-11 AU AU27662/00A patent/AU775947B2/en not_active Ceased
- 2000-05-09 DE DE60023063T patent/DE60023063T2/de not_active Expired - Fee Related
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- 2000-05-09 DK DK00303889T patent/DK1054002T3/da active
- 2000-05-09 ES ES00303889T patent/ES2248017T3/es not_active Expired - Lifetime
- 2000-05-09 AT AT00303889T patent/ATE306474T1/de not_active IP Right Cessation
- 2000-05-11 TW TW089109033A patent/TWI286133B/zh not_active IP Right Cessation
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- 2000-05-16 RU RU2000112354/04A patent/RU2181120C2/ru not_active IP Right Cessation
- 2000-05-16 KR KR10-2000-0025978A patent/KR100386226B1/ko not_active Expired - Fee Related
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- 2000-05-16 HU HU0001928A patent/HUP0001928A3/hu unknown
- 2000-05-16 CZ CZ20001800A patent/CZ299474B6/cs not_active IP Right Cessation
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Publication number	Publication date
IL136105A (en)	2006-07-05
AU775947B2 (en)	2004-08-19
IN192341B (2)	2004-04-10
DE60023063T2 (de)	2006-04-20
ES2248017T3 (es)	2006-03-16
KR20010020845A (ko)	2001-03-15
TR200001403A2 (tr)	2000-12-21
EP1054002B1 (en)	2005-10-12
JP2000355584A (ja)	2000-12-26
KR100386226B1 (ko)	2003-06-02
DE60023063D1 (de)	2006-02-23
RS49964B (sr)	2008-09-29
MXPA00004790A (es)	2002-03-08
CN1288005A (zh)	2001-03-21
PL198153B1 (pl)	2008-05-30
EP1054002A1 (en)	2000-11-22
CA2308817C (en)	2005-06-14
HU0001928D0 (en)	2000-07-28
AU2766200A (en)	2000-11-23
PL340157A1 (en)	2000-11-20
ATE306474T1 (de)	2005-10-15
BR0001773A (pt)	2001-01-02
DK1054002T3 (da)	2006-02-20
HUP0001928A2 (en)	2001-03-28
YU19600A (sh)	2002-03-18
AR020029A1 (es)	2002-03-27
TWI286133B (en)	2007-09-01
US6316632B1 (en)	2001-11-13
RU2181120C2 (ru)	2002-04-10
CZ299474B6 (cs)	2008-08-06
IL136105A0 (en)	2001-05-20
HK1032397A1 (en)	2001-07-20
JP3837011B2 (ja)	2006-10-25
HUP0001928A3 (en)	2002-05-28
ID26061A (id)	2000-11-23
CZ20001800A3 (cs)	2001-03-14
CA2308817A1 (en)	2000-11-17
ZA200002375B (en)	2001-11-15

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2005-08-31	C14	Grant of patent or utility model
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2010-09-01	C17	Cessation of patent right
2010-09-01	CF01	Termination of patent right due to non-payment of annual fee	Granted publication date: 20050831

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