NO324468B1 - Kjemiske forbindelser - Google Patents
Kjemiske forbindelser Download PDFInfo
- Publication number
- NO324468B1 NO324468B1 NO20031561A NO20031561A NO324468B1 NO 324468 B1 NO324468 B1 NO 324468B1 NO 20031561 A NO20031561 A NO 20031561A NO 20031561 A NO20031561 A NO 20031561A NO 324468 B1 NO324468 B1 NO 324468B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- methyl
- bis
- fluoro
- trifluoromethyl
- Prior art date
Links
- 239000000126 substance Substances 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 157
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000012453 solvate Substances 0.000 claims abstract description 13
- 102000003141 Tachykinin Human genes 0.000 claims abstract description 10
- 108060008037 tachykinin Proteins 0.000 claims abstract description 10
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- -1 4-(S)-(4-cyclopropanyl-piperazin-1 -yl)-2-(R)-(4-fluoro-2-methyl-phenyl)-piperidine-1-carboxylic acid Chemical compound 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 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 claims description 11
- 102100024304 Protachykinin-1 Human genes 0.000 claims description 11
- 101800003906 Substance P Proteins 0.000 claims description 11
- ZHIAARPZLAPMHX-ZCFIWIBFSA-N (1r)-1-[3,5-bis(trifluoromethyl)phenyl]-n-methylethanamine Chemical compound CN[C@H](C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZHIAARPZLAPMHX-ZCFIWIBFSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- KMDQRDXBBHPCEY-FUHWJXTLSA-N (2r,4s)-4-(4-acetylpiperazin-1-yl)-2-(4-fluoro-2-methylphenyl)piperidine-1-carboxylic acid Chemical compound C1CN(C(=O)C)CCN1[C@@H]1C[C@H](C=2C(=CC(F)=CC=2)C)N(C(O)=O)CC1 KMDQRDXBBHPCEY-FUHWJXTLSA-N 0.000 claims description 8
- ADTNSTHKMIPKIJ-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ADTNSTHKMIPKIJ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 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 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- IYIQFFKRUFGPNU-OMOCHNIRSA-N (2R)-2-(4-fluoro-2-methylphenyl)-4-(4-methylpiperazin-1-yl)piperidine-1-carboxylic acid Chemical compound FC1=CC(=C(C=C1)[C@@H]1N(CCC(C1)N1CCN(CC1)C)C(=O)O)C IYIQFFKRUFGPNU-OMOCHNIRSA-N 0.000 claims description 3
- PGUHTWOXJGVPAY-FYZOBXCZSA-N C[C@H](C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)NC.CS(O)(=O)=O Chemical compound C[C@H](C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)NC.CS(O)(=O)=O PGUHTWOXJGVPAY-FYZOBXCZSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 3
- JEUIJUTULHLCOX-IEBWSBKVSA-N (2r,4r)-2-(4-fluoro-2-methylphenyl)-4-[4-(2-methylpropanoyl)piperazin-1-yl]piperidine-1-carboxylic acid Chemical compound C1CN(C(=O)C(C)C)CCN1[C@H]1C[C@H](C=2C(=CC(F)=CC=2)C)N(C(O)=O)CC1 JEUIJUTULHLCOX-IEBWSBKVSA-N 0.000 claims description 2
- KMDQRDXBBHPCEY-SJLPKXTDSA-N (2r,4r)-4-(4-acetylpiperazin-1-yl)-2-(4-fluoro-2-methylphenyl)piperidine-1-carboxylic acid Chemical compound C1CN(C(=O)C)CCN1[C@H]1C[C@H](C=2C(=CC(F)=CC=2)C)N(C(O)=O)CC1 KMDQRDXBBHPCEY-SJLPKXTDSA-N 0.000 claims description 2
- AVEFAYLDJJNSLQ-IAIFEWERSA-N (2r,4r)-4-(4-acetylpiperazin-1-yl)-n-[(1r)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-2-(4-fluorophenyl)-n-methylpiperidine-1-carboxamide Chemical compound C1([C@H]2C[C@@H](CCN2C(=O)N(C)[C@H](C)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)N2CCN(CC2)C(C)=O)=CC=C(F)C=C1 AVEFAYLDJJNSLQ-IAIFEWERSA-N 0.000 claims description 2
- JEUIJUTULHLCOX-PKOBYXMFSA-N (2r,4s)-2-(4-fluoro-2-methylphenyl)-4-[4-(2-methylpropanoyl)piperazin-1-yl]piperidine-1-carboxylic acid Chemical compound C1CN(C(=O)C(C)C)CCN1[C@@H]1C[C@H](C=2C(=CC(F)=CC=2)C)N(C(O)=O)CC1 JEUIJUTULHLCOX-PKOBYXMFSA-N 0.000 claims description 2
- DRTDSPQHMOBNPE-GOEBONIOSA-N (2r,4s)-2-(4-fluoro-2-methylphenyl)-4-piperazin-1-ylpiperidine-1-carboxylic acid Chemical compound CC1=CC(F)=CC=C1[C@@H]1N(C(O)=O)CC[C@H](N2CCNCC2)C1 DRTDSPQHMOBNPE-GOEBONIOSA-N 0.000 claims description 2
- XHZRREUKUVJSDC-AZGAKELHSA-N (2r,4s)-4-(4-acetylpiperazin-1-yl)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-(4-fluoro-2-methylphenyl)-n-methylpiperidine-1-carboxamide Chemical compound N1([C@H](C[C@H](CC1)N1CCN(CC1)C(C)=O)C=1C(=CC(F)=CC=1)C)C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XHZRREUKUVJSDC-AZGAKELHSA-N 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- XKXCTVMNFUFTFU-DLBZAZTESA-N (2r,4s)-4-(4-acetylpiperazin-1-yl)-2-(4-fluorophenyl)piperidine-1-carboxylic acid Chemical compound C1CN(C(=O)C)CCN1[C@@H]1C[C@H](C=2C=CC(F)=CC=2)N(C(O)=O)CC1 XKXCTVMNFUFTFU-DLBZAZTESA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 143
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 239000000543 intermediate Substances 0.000 description 77
- 239000000203 mixture Substances 0.000 description 64
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 40
- 239000012299 nitrogen atmosphere Substances 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 238000001819 mass spectrum Methods 0.000 description 29
- 239000007787 solid Substances 0.000 description 27
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000003818 flash chromatography Methods 0.000 description 19
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- 235000019198 oils Nutrition 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000284 extract Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
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- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 11
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
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| TWI283241B (en) * | 2002-05-29 | 2007-07-01 | Tanabe Seiyaku Co | Novel piperidine compound |
| JP4079727B2 (ja) | 2002-09-06 | 2008-04-23 | セントラル硝子株式会社 | 光学活性１−（フルオロ、トリフルオロメチルまたはトリフルオロメトキシ置換フェニル）アルキルアミンｎ−モノアルキル誘導体とその製造方法 |
| JP4660199B2 (ja) * | 2002-12-23 | 2011-03-30 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 置換１−ピペリジン−４−イル−４−アゼチジン−３−イル−ピペラジン誘導体およびそれらのニューロキニン拮抗薬としての使用 |
| JO2485B1 (en) * | 2002-12-23 | 2009-01-20 | شركة جانسين فارماسوتيكا ان. في | 1-Piperidine-3-Yl-4-Piperidine-4-Yl-Piperazine derivatives substituted and used as quinine antagonists |
| CA2509090C (en) * | 2002-12-23 | 2012-01-24 | Janssen Pharmaceutica N.V. | Substituted 4-(4-piperidin-4-yl-piperazin-1-yl)-azepane derivatives and their use as neurokinin antagonists |
| JO2696B1 (en) * | 2002-12-23 | 2013-03-03 | شركة جانسين فارماسوتيكا ان. في | Derivatives of 1-piperdine-4-yl-4-biprolidine-3-yl-piperazine substituted and used as quinine antagonists |
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| CA2528652A1 (en) * | 2003-06-19 | 2004-12-23 | Pfizer Products Inc. | Nk1 antagonist |
| JO2525B1 (en) * | 2004-04-08 | 2010-03-17 | شركة جانسين فارماسوتيكا ان. في | Derived 4-alkyl-and-4-canoelperidine derivatives and their use as anti-neroquin |
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