JP2004510697A5 - - Google Patents
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- JP2004510697A5 JP2004510697A5 JP2001586288A JP2001586288A JP2004510697A5 JP 2004510697 A5 JP2004510697 A5 JP 2004510697A5 JP 2001586288 A JP2001586288 A JP 2001586288A JP 2001586288 A JP2001586288 A JP 2001586288A JP 2004510697 A5 JP2004510697 A5 JP 2004510697A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- aryl
- piperidin
- compound
- heteroaryl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 description 78
- 125000003118 aryl group Chemical group 0.000 description 54
- 125000001072 heteroaryl group Chemical group 0.000 description 48
- 125000000217 alkyl group Chemical group 0.000 description 47
- 229910052739 hydrogen Inorganic materials 0.000 description 30
- 239000001257 hydrogen Substances 0.000 description 30
- 239000008194 pharmaceutical composition Substances 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 20
- -1 hydroxy, ureido Chemical group 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 125000005843 halogen group Chemical group 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 15
- 150000002431 hydrogen Chemical group 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 14
- 230000003110 anti-inflammatory effect Effects 0.000 description 13
- 125000001041 indolyl group Chemical group 0.000 description 13
- 239000000808 adrenergic beta-agonist Substances 0.000 description 9
- 206010003246 arthritis Diseases 0.000 description 9
- 239000003246 corticosteroid Substances 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 208000024891 symptom Diseases 0.000 description 9
- 125000002541 furyl group Chemical group 0.000 description 8
- 125000004076 pyridyl group Chemical group 0.000 description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- 125000005018 aryl alkenyl group Chemical group 0.000 description 7
- 206010010741 Conjunctivitis Diseases 0.000 description 6
- 206010016654 Fibrosis Diseases 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 6
- 208000006673 asthma Diseases 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 6
- 208000027866 inflammatory disease Diseases 0.000 description 6
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 5
- 150000001204 N-oxides Chemical class 0.000 description 5
- 125000006383 alkylpyridyl group Chemical group 0.000 description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 description 5
- 239000002260 anti-inflammatory agent Substances 0.000 description 5
- 239000000812 cholinergic antagonist Substances 0.000 description 5
- 229960001334 corticosteroids Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 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 description 4
- 230000001078 anti-cholinergic effect Effects 0.000 description 4
- 125000003435 aroyl group Chemical group 0.000 description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 125000005015 aryl alkynyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000005312 heteroarylalkynyl group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 3
- PDNHLCRMUIGNBV-UHFFFAOYSA-N 1-pyridin-2-ylethanamine Chemical compound CC(N)C1=CC=CC=N1 PDNHLCRMUIGNBV-UHFFFAOYSA-N 0.000 description 3
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 description 3
- 206010002198 Anaphylactic reaction Diseases 0.000 description 3
- 206010002383 Angina Pectoris Diseases 0.000 description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 3
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 206010012438 Dermatitis atopic Diseases 0.000 description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 description 3
- 201000005569 Gout Diseases 0.000 description 3
- 206010018634 Gouty Arthritis Diseases 0.000 description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 3
- 208000029523 Interstitial Lung disease Diseases 0.000 description 3
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 3
- 206010028594 Myocardial fibrosis Diseases 0.000 description 3
- 208000009905 Neurofibromatoses Diseases 0.000 description 3
- 208000008469 Peptic Ulcer Diseases 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 3
- 206010039085 Rhinitis allergic Diseases 0.000 description 3
- 206010039710 Scleroderma Diseases 0.000 description 3
- 208000006011 Stroke Diseases 0.000 description 3
- 206010048873 Traumatic arthritis Diseases 0.000 description 3
- 229940122598 Tryptase inhibitor Drugs 0.000 description 3
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 3
- 201000010105 allergic rhinitis Diseases 0.000 description 3
- 230000036783 anaphylactic response Effects 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 210000001188 articular cartilage Anatomy 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 201000008937 atopic dermatitis Diseases 0.000 description 3
- 229950000210 beclometasone dipropionate Drugs 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000003846 cartilage breakdown Effects 0.000 description 3
- 230000007882 cirrhosis Effects 0.000 description 3
- 208000019425 cirrhosis of liver Diseases 0.000 description 3
- 229960000265 cromoglicic acid Drugs 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 229960003957 dexamethasone Drugs 0.000 description 3
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 229960001022 fenoterol Drugs 0.000 description 3
- 230000004761 fibrosis Effects 0.000 description 3
- 229960000676 flunisolide Drugs 0.000 description 3
- 229960002848 formoterol Drugs 0.000 description 3
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 3
- 125000004447 heteroarylalkenyl group Chemical group 0.000 description 3
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 description 3
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 3
- 230000001969 hypertrophic effect Effects 0.000 description 3
- 229960001361 ipratropium bromide Drugs 0.000 description 3
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 3
- 208000018937 joint inflammation Diseases 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- 229960002259 nedocromil sodium Drugs 0.000 description 3
- 201000004931 neurofibromatosis Diseases 0.000 description 3
- 201000008482 osteoarthritis Diseases 0.000 description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 208000011906 peptic ulcer disease Diseases 0.000 description 3
- 208000028169 periodontal disease Diseases 0.000 description 3
- 208000005069 pulmonary fibrosis Diseases 0.000 description 3
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 201000005404 rubella Diseases 0.000 description 3
- 229960002052 salbutamol Drugs 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 229960000195 terbutaline Drugs 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 239000002750 tryptase inhibitor Substances 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 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 description 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 description 2
- 208000034189 Sclerosis Diseases 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- 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 description 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 description 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 description 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 description 2
- 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 description 2
- JXIJLJZBOLCXGH-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(3-bromo-4-fluorophenyl)methanone Chemical compound NCC1=CC=CC(C2CCN(CC2)C(=O)C=2C=C(Br)C(F)=CC=2)=C1 JXIJLJZBOLCXGH-UHFFFAOYSA-N 0.000 description 2
- 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 description 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 description 2
- JBAHGAJATNQNJU-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-(3-methylsulfanyl-6,7-dihydro-2-benzothiophen-1-yl)methanone Chemical compound C=12CCC=CC2=C(SC)SC=1C(=O)N(CC1)CCC1C1=CC=CC(CN)=C1 JBAHGAJATNQNJU-UHFFFAOYSA-N 0.000 description 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 description 2
- 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 description 2
- 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 description 2
- LADJJFSUUQXHGN-UHFFFAOYSA-N [4-[3-(aminomethyl)phenyl]piperidin-1-yl]-[3-[2-(2-fluorophenyl)ethynyl]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(C=CC=2)C#CC=2C(=CC=CC=2)F)=C1 LADJJFSUUQXHGN-UHFFFAOYSA-N 0.000 description 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 description 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 description 2
- 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 description 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 description 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 description 2
- 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 description 2
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 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 description 2
- 229960002117 triamcinolone acetonide Drugs 0.000 description 2
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 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 description 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 description 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 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 0 CC(*)(CN(C)C(*)=O)[C@@](C1)C1(C)C1=CC(C(*)(*)N)=CCC1 Chemical compound CC(*)(CN(C)C(*)=O)[C@@](C1)C1(C)C1=CC(C(*)(*)N)=CCC1 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229940126307 triamcinolone acetate Drugs 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0012362.0A GB0012362D0 (en) | 2000-05-22 | 2000-05-22 | Chemical compounds |
| GB0012362.0 | 2000-05-22 | ||
| US09/843,126 | 2001-04-26 | ||
| US09/843,126 US6977263B2 (en) | 2000-05-22 | 2001-04-26 | Chemical compounds |
| PCT/US2001/013811 WO2001090101A1 (en) | 2000-05-22 | 2001-04-27 | Arylmethylamine derivatives for use as tryptase inhibitors |
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| DE602005017471D1 (enExample) * | 2004-03-02 | 2009-12-17 | Aventis Pharma Inc | |
| 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 |
| JP2008515992A (ja) | 2004-10-13 | 2008-05-15 | ピーティーシー セラピューティクス，インコーポレーテッド | 体細胞変異に起因する疾患の阻止／治療用医薬を製造するための規定化合物の使用 |
| US7786308B2 (en) * | 2005-03-28 | 2010-08-31 | 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 |
| US20100028895A1 (en) | 2007-01-10 | 2010-02-04 | 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 |
| CN103508936A (zh) * | 2008-08-22 | 2014-01-15 | 赛诺菲-安万特 | 用于制备吲哚苄胺化合物的中间体 |
| FR2955324A1 (fr) * | 2010-01-15 | 2011-07-22 | Sanofi Aventis | [4-(5-aminomethyl-phenyl)-piperidin-1-yl]-1h-indol-3-yl]-methanones disubstituees |
| WO2011079102A1 (en) * | 2009-12-23 | 2011-06-30 | Sanofi | Indolyl-piperidinyl benzylamines as beta-tryptase inhibitors |
| MX2012007080A (es) | 2009-12-23 | 2012-07-20 | Sanofi Sa | [4[4-(5-aminometil-2-fluoro-fenil)-piperidin-1-il]-(1h-pirrolo-pi ri-din-il)-metanonas y sintesis de las mismas. |
| AU2010333772B2 (en) | 2009-12-23 | 2016-07-14 | Sanofi | Prodrugs of [4[4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-(1H-pyrrolo-pyridin-yl)-methanones and synthesis thereof |
| 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 |
| US20140194383A1 (en) * | 2011-04-07 | 2014-07-10 | Cornell University | Monomers capable of dimerizing in an aqueous solution, and methods of using same |
| HUE043221T2 (hu) * | 2011-05-27 | 2019-08-28 | Lexicon Pharmaceuticals Inc | Notum pektinacetilészteráz 4H-tieno[3,2-C]kromén-alapú inhibitorai és alkalmazási eljárásaik |
| 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 |
| WO2015073864A1 (en) | 2013-11-15 | 2015-05-21 | The Wisar 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 |
| TW202115086A (zh) * | 2019-06-28 | 2021-04-16 | 美商輝瑞大藥廠 | Bckdk抑制劑 |
| JP7677983B2 (ja) * | 2020-01-23 | 2025-05-15 | マイオフォルテ セラピューティクス，インク． | Ｐｇｄｈ阻害剤、およびその作製と使用の方法 |
| WO2021245499A1 (en) * | 2020-06-04 | 2021-12-09 | Pillai Universal Llc | Novel small molecules for targeted degradation of untargetable kras in cancer therapy |
Family Cites Families (7)
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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 |
-
2000
- 2000-05-22 GB GBGB0012362.0A patent/GB0012362D0/en not_active Ceased
-
2001
- 2001-04-26 US US09/843,126 patent/US6977263B2/en not_active Expired - Lifetime
- 2001-04-27 EA EA200201276A patent/EA006687B1/ru not_active IP Right Cessation
- 2001-04-27 DE DE60140871T patent/DE60140871D1/de not_active Expired - Lifetime
- 2001-04-27 PT PT01930925T patent/PT1296972E/pt unknown
- 2001-04-27 DK DK01930925.1T patent/DK1296972T3/da active
- 2001-04-27 ES ES01930925T patent/ES2337550T3/es not_active Expired - Lifetime
- 2001-04-27 CN CN2005101063047A patent/CN1740169B/zh not_active Expired - Lifetime
- 2001-04-27 RS YU87202A patent/RS51751B/sr unknown
- 2001-04-27 JP JP2001586288A patent/JP4796732B2/ja not_active Expired - Fee Related
- 2001-04-27 ME MEP-546/08A patent/MEP54608A/xx unknown
- 2001-04-27 AT AT01930925T patent/ATE452884T1/de active
- 2001-04-27 UA UA20021210404A patent/UA74579C2/uk unknown
-
2002
- 2002-11-13 IL IL152830A patent/IL152830A/en not_active IP Right Cessation
- 2002-11-15 CR CR6824A patent/CR6824A/es unknown
- 2002-11-21 ZA ZA200209484A patent/ZA200209484B/en unknown
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