ZA200209484B - Arylmethylamine derivatives for use as tryptase inhibitors. - Google Patents
Arylmethylamine derivatives for use as tryptase inhibitors. Download PDFInfo
- Publication number
- ZA200209484B ZA200209484B ZA200209484A ZA200209484A ZA200209484B ZA 200209484 B ZA200209484 B ZA 200209484B ZA 200209484 A ZA200209484 A ZA 200209484A ZA 200209484 A ZA200209484 A ZA 200209484A ZA 200209484 B ZA200209484 B ZA 200209484B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- phenyl
- piperidin
- aryl
- heteroaryl
- Prior art date
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- 239000002750 tryptase inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 141
- 238000000034 method Methods 0.000 claims abstract description 19
- 208000006673 asthma Diseases 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 85
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- -1 cyclic amine Chemical class 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000001041 indolyl group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229940002612 prodrug Drugs 0.000 claims description 13
- 239000000651 prodrug Substances 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000003435 aroyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 9
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 6
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- DXHCUDMXKAQPDH-UHFFFAOYSA-N 1-[4-[3-(aminomethyl)phenyl]piperidine-1-carbonyl]-3-ethylsulfanyl-6,6-dimethyl-5,7-dihydro-2-benzothiophen-4-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12CC(C)(C)CC(=O)C2=C(SCC)SC=1C(=O)N(CC1)CCC1C1=CC=CC(CN)=C1 DXHCUDMXKAQPDH-UHFFFAOYSA-N 0.000 claims 2
- BMGUQSJLWYQHHA-UHFFFAOYSA-N 1-[4-[3-(aminomethyl)phenyl]piperidine-1-carbonyl]-3-methylsulfanyl-6,7-dihydro-5h-2-benzothiophen-4-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12CCCC(=O)C2=C(SC)SC=1C(=O)N(CC1)CCC1C1=CC=CC(CN)=C1 BMGUQSJLWYQHHA-UHFFFAOYSA-N 0.000 claims 2
- CTBHKLOYRNYMJD-UHFFFAOYSA-N 1-[4-[3-(aminomethyl)phenyl]piperidine-1-carbonyl]-3-propylsulfanyl-6,7-dihydro-5h-2-benzothiophen-4-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12CCCC(=O)C2=C(SCCC)SC=1C(=O)N(CC1)CCC1C1=CC=CC(CN)=C1 CTBHKLOYRNYMJD-UHFFFAOYSA-N 0.000 claims 2
- HHKGATDJOAYQSW-UHFFFAOYSA-N 4-[3-(aminomethyl)phenyl]-n-(3,4-dichlorophenyl)piperidine-1-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCC1=CC=CC(C2CCN(CC2)C(=O)NC=2C=C(Cl)C(Cl)=CC=2)=C1 HHKGATDJOAYQSW-UHFFFAOYSA-N 0.000 claims 2
- KLPMSROOCJMQJH-UHFFFAOYSA-N OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NCc1cccc(c1)C1CCN(CC1)C(=O)c1cccc(CCc2ccc(N)nc2)c1 Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NCc1cccc(c1)C1CCN(CC1)C(=O)c1cccc(CCc2ccc(N)nc2)c1 KLPMSROOCJMQJH-UHFFFAOYSA-N 0.000 claims 2
- ZIPGFTLBRITSHA-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(1-benzothiophen-2-yl)methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCC1=CC=CC(C2CCN(CC2)C(=O)C=2SC3=CC=CC=C3C=2)=C1 ZIPGFTLBRITSHA-UHFFFAOYSA-N 0.000 claims 2
- SDXRQZKFUGAQCY-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(1-methylindol-3-yl)methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2N(C)C=C1C(=O)N(CC1)CCC1C1=CC=CC(CN)=C1 SDXRQZKFUGAQCY-UHFFFAOYSA-N 0.000 claims 2
- OCBLHVOVZOVDBU-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(1h-indol-6-yl)methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C3NC=CC3=CC=2)=C1 OCBLHVOVZOVDBU-UHFFFAOYSA-N 0.000 claims 2
- SPEYRMLPHOMFOQ-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(3-chlorothieno[3,2-b]thiophen-5-yl)methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCC1=CC=CC(C2CCN(CC2)C(=O)C=2SC=3C(Cl)=CSC=3C=2)=C1 SPEYRMLPHOMFOQ-UHFFFAOYSA-N 0.000 claims 2
- LSPBMRUHDVYMBZ-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(5,6-dichloropyridin-3-yl)methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=NC=2)=C1 LSPBMRUHDVYMBZ-UHFFFAOYSA-N 0.000 claims 2
- BGSDHEKXBCRMNI-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[3-[2-(4-hydroxyphenyl)ethyl]phenyl]methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(CCC=3C=CC(O)=CC=3)C=CC=2)=C1 BGSDHEKXBCRMNI-UHFFFAOYSA-N 0.000 claims 2
- KMXXSMSBPCYYHI-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[3-[2-(6-aminopyridin-3-yl)ethyl]phenyl]methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(CCC=3C=NC(N)=CC=3)C=CC=2)=C1 KMXXSMSBPCYYHI-UHFFFAOYSA-N 0.000 claims 2
- HKPWBHWNFDDGLH-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[5-(2-phenylethyl)thiophen-2-yl]methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2SC(CCC=3C=CC=CC=3)=CC=2)=C1 HKPWBHWNFDDGLH-UHFFFAOYSA-N 0.000 claims 2
- YPVSDOKGNYAHFF-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[5-(2-phenylethynyl)pyridin-3-yl]methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(C=NC=2)C#CC=2C=CC=CC=2)=C1 YPVSDOKGNYAHFF-UHFFFAOYSA-N 0.000 claims 2
- VEDNINLWJKUNKG-UHFFFAOYSA-N [4-[5-(aminomethyl)-2-fluorophenyl]piperidin-1-yl]-[5-(2-phenylethyl)pyridin-3-yl]methanone Chemical compound NCC1=CC=C(F)C(C2CCN(CC2)C(=O)C=2C=C(CCC=3C=CC=CC=3)C=NC=2)=C1 VEDNINLWJKUNKG-UHFFFAOYSA-N 0.000 claims 2
- PZCWEEOFDCYLCR-MBUXBYMASA-N ethyl (3s,4r)-4-[3-(aminomethyl)phenyl]-1-[5-(2-phenylethyl)pyridine-3-carbonyl]piperidine-3-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1([C@@H]2CCN(C[C@H]2C(=O)OCC)C(=O)C=2C=C(CCC=3C=CC=CC=3)C=NC=2)=CC=CC(CN)=C1 PZCWEEOFDCYLCR-MBUXBYMASA-N 0.000 claims 2
- PCQKANQBKPRBFA-UHFFFAOYSA-N 1-[4-[3-(aminomethyl)phenyl]piperidin-1-yl]-3-cyclohexylpropan-1-one Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)CCC2CCCCC2)=C1 PCQKANQBKPRBFA-UHFFFAOYSA-N 0.000 claims 1
- OJBYFYZTTBGOCP-UHFFFAOYSA-N 1-[4-[3-(aminomethyl)phenyl]piperidine-1-carbonyl]-3-propan-2-ylsulfanyl-6,7-dihydro-5h-2-benzothiophen-4-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=12CCCC(=O)C2=C(SC(C)C)SC=1C(=O)N(CC1)CCC1C1=CC=CC(CN)=C1 OJBYFYZTTBGOCP-UHFFFAOYSA-N 0.000 claims 1
- UXFYXVKSDMFICM-UHFFFAOYSA-N 4-[3-(aminomethyl)phenyl]-1-[5-(2-phenylethyl)pyridine-3-carbonyl]piperidine-4-carbonitrile Chemical compound NCC1=CC=CC(C2(CCN(CC2)C(=O)C=2C=C(CCC=3C=CC=CC=3)C=NC=2)C#N)=C1 UXFYXVKSDMFICM-UHFFFAOYSA-N 0.000 claims 1
- UTMHTSVCUOVUSH-UHFFFAOYSA-N 4-[3-(aminomethyl)phenyl]-1-[5-(2-phenylethyl)pyridine-3-carbonyl]piperidine-4-carbonitrile;[4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(3,4-dichlorophenyl)methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1.NCC1=CC=CC(C2(CCN(CC2)C(=O)C=2C=C(CCC=3C=CC=CC=3)C=NC=2)C#N)=C1 UTMHTSVCUOVUSH-UHFFFAOYSA-N 0.000 claims 1
- TZKIGPLNVNUIRO-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]-4-hydroxypiperidin-1-yl]-[5-(2-phenylethyl)pyridin-3-yl]methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.NCC1=CC=CC(C2(O)CCN(CC2)C(=O)C=2C=C(CCC=3C=CC=CC=3)C=NC=2)=C1 TZKIGPLNVNUIRO-UHFFFAOYSA-N 0.000 claims 1
- IBCQONBZMVLJSZ-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(2,3-dihydro-1-benzofuran-5-yl)methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C3CCOC3=CC=2)=C1 IBCQONBZMVLJSZ-UHFFFAOYSA-N 0.000 claims 1
- UEMUFZHSNOUPKR-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(3-bromo-5-iodophenyl)methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(I)C=C(Br)C=2)=C1 UEMUFZHSNOUPKR-UHFFFAOYSA-N 0.000 claims 1
- SGSBBQAXTBXELX-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[3-(2-phenylethyl)phenyl]methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(CCC=3C=CC=CC=3)C=CC=2)=C1 SGSBBQAXTBXELX-UHFFFAOYSA-N 0.000 claims 1
- VHVIIBRDQHUVJJ-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[3-[2-(2-fluorophenyl)ethyl]phenyl]methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(CCC=3C(=CC=CC=3)F)C=CC=2)=C1 VHVIIBRDQHUVJJ-UHFFFAOYSA-N 0.000 claims 1
- QLERJFUUECMDTN-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[5-(2-phenylethynyl)furan-2-yl]methanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCC1=CC=CC(C2CCN(CC2)C(=O)C=2OC(=CC=2)C#CC=2C=CC=CC=2)=C1 QLERJFUUECMDTN-UHFFFAOYSA-N 0.000 claims 1
- HLRRPEGCCMGTFV-UHFFFAOYSA-N [4-[5-(aminomethyl)-2-methylphenyl]piperidin-1-yl]-[5-(2-phenylethyl)pyridin-3-yl]methanone Chemical compound CC1=CC=C(CN)C=C1C1CCN(C(=O)C=2C=C(CCC=3C=CC=CC=3)C=NC=2)CC1 HLRRPEGCCMGTFV-UHFFFAOYSA-N 0.000 claims 1
- 125000006383 alkylpyridyl group Chemical group 0.000 claims 1
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 claims 1
- 102000001400 Tryptase Human genes 0.000 abstract description 14
- 108060005989 Tryptase Proteins 0.000 abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
- 230000001668 ameliorated effect Effects 0.000 abstract description 5
- 201000010099 disease Diseases 0.000 abstract description 5
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- 239000003112 inhibitor Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 208000035475 disorder Diseases 0.000 abstract description 2
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 210000003630 histaminocyte Anatomy 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 206010003246 arthritis Diseases 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 description 4
- 239000002260 anti-inflammatory agent Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 3
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- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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KR101182690B1 (ko) * | 2004-03-02 | 2012-09-14 | 아벤티스 파마슈티칼스 인크. | 트립타제 억제제의 제조방법 |
DOP2005000039A (es) * | 2004-03-26 | 2005-10-31 | Aventis Pharma Inc | Hidrocloruro de [4-(5-aminometil-2-fluoro-fenil)- piperidin-1-il]-(4-bomo-3-metil-5-propoxi-tiofen-2-il)-metanona como un inhibidor de la triptasa de mastocitos |
US7423176B2 (en) * | 2004-04-13 | 2008-09-09 | Cephalon, Inc. | Bicyclic aromatic sulfinyl derivatives |
EP1812071A2 (en) * | 2004-10-13 | 2007-08-01 | PTC Therapeutics, Inc. | Compounds for nonsense suppression, use of these compounds for the manufacture of a medicament for treating somatic mutation-related diseases |
EP1863490A2 (en) * | 2005-03-28 | 2007-12-12 | Vertex Pharmaceuticals Incorporated | Muscarinic modulators |
JP5019768B2 (ja) * | 2006-03-23 | 2012-09-05 | 独立行政法人科学技術振興機構 | 新規低分子化合物およびその製造方法 |
AU2008204923A1 (en) * | 2007-01-10 | 2008-07-17 | Sanofi-Aventis | Method for determining the stability of organic methyleneamines in the presence of semicarbazide-sensitive amine oxidase |
US8703119B2 (en) * | 2007-10-05 | 2014-04-22 | Polygene Ltd. | Injectable biodegradable polymer compositions for soft tissue repair and augmentation |
EP2224803B1 (en) * | 2007-11-21 | 2014-04-02 | Janssen Pharmaceutica N.V. | Spiropiperidines for use as tryptase inhibitors |
PT2367812E (pt) * | 2008-08-22 | 2016-01-20 | Sanofi Sa | [4-(5-aminometil-2-fluoro-fenil)-piperidin-1-il]-[7-fluoro-1-(2-metoxi-etil)-4-trifluorometoxi-1h-indol-3-il]metanona como um inibidor da triptase de mastócitos |
FR2955324A1 (fr) * | 2010-01-15 | 2011-07-22 | Sanofi Aventis | [4-(5-aminomethyl-phenyl)-piperidin-1-yl]-1h-indol-3-yl]-methanones disubstituees |
PL2516418T3 (pl) | 2009-12-23 | 2014-10-31 | Sanofi Sa | Proleki [4-[4-(5-aminometylo-2-fluoro-fenylo)-piperydyn-1-ylo]-(1H-pirolo-pirydynylo)-metanonów oraz ich synteza |
CN102770431A (zh) | 2009-12-23 | 2012-11-07 | 赛诺菲 | [4[4-(5-氨基甲基-2-氟-苯基)-哌啶-1-基]-(1h-吡咯并吡啶-基)-甲酮及其合成 |
CN102770425A (zh) * | 2009-12-23 | 2012-11-07 | 赛诺菲 | 用作β-类胰蛋白酶抑制剂的吲哚基-哌啶基苄胺类化合物 |
JP2013520506A (ja) * | 2010-02-24 | 2013-06-06 | サノフイ | 皮膚科学的なアレルギー状態の治療 |
WO2013058824A1 (en) * | 2011-04-07 | 2013-04-25 | Cornell University | Monomers capable of dimerizing in an aqueous solution, and methods of using same |
WO2012166458A1 (en) * | 2011-05-27 | 2012-12-06 | Lexicon Pharmaceuticals, Inc. | 4h-thieno[3,2-c]chromene-based inhibitors of notum pectinacetylesterase and methods of their use |
US9701689B2 (en) | 2012-11-30 | 2017-07-11 | Kyowa Hakko Kirin Co., Ltd. | Substituted pyridines and pyridazines as CCR10 receptor inhibitors |
TW201441193A (zh) * | 2012-12-06 | 2014-11-01 | Kyowa Hakko Kirin Co Ltd | 吡啶酮化合物 |
AU2014348422B2 (en) | 2013-11-15 | 2019-02-14 | The Wistar Institute Of Anatomy And Biology | EBNA1 inhibitors and their method of use |
AU2017311691B2 (en) | 2016-08-18 | 2021-12-02 | Vidac Pharma Ltd. | Piperazine derivatives, pharmaceutical compositions and methods of use thereof |
CN110357833B (zh) * | 2019-06-03 | 2022-05-24 | 杭州维坦医药科技有限公司 | 芳杂乙酰胺类衍生物及其制备和应用 |
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US5221676A (en) * | 1992-02-06 | 1993-06-22 | Warner-Lambert Company | 7-substituted quinolones and naphthyridones as antibacterial agents |
DE4234295A1 (de) * | 1992-10-12 | 1994-04-14 | Thomae Gmbh Dr K | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
DE4407139A1 (de) * | 1994-03-04 | 1995-09-07 | Thomae Gmbh Dr K | Aryl-1-azacycloalkane und deren Salze, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie Verfahren zu ihrer Herstellung |
US5629321A (en) * | 1994-10-27 | 1997-05-13 | Mitsui Toatsu Chemicals, Inc. | Bicyclic compound and platelet aggregation inhibitor containing the same |
US6740682B2 (en) * | 1997-08-29 | 2004-05-25 | Tularik Limited | Meta-benzamidine derivatives as serine protease inhibitors |
GB9912411D0 (en) * | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
US20020045613A1 (en) * | 2000-04-27 | 2002-04-18 | Heinz Pauls | 1-aroyl-piperidinyl benzamidines |
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CN1740169A (zh) | 2006-03-01 |
PT1296972E (pt) | 2010-03-03 |
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DE60140871D1 (de) | 2010-02-04 |
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UA74579C2 (en) | 2006-01-16 |
EA006687B1 (ru) | 2006-02-24 |
CR6824A (es) | 2008-11-25 |
HK1087702A1 (en) | 2006-10-20 |
CN1740169B (zh) | 2010-04-21 |
US6977263B2 (en) | 2005-12-20 |
JP4796732B2 (ja) | 2011-10-19 |
ATE452884T1 (de) | 2010-01-15 |
GB0012362D0 (en) | 2000-07-12 |
EA200201276A1 (ru) | 2003-06-26 |
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