OA12274A - Arylmethylamine derivatives for use as tryptase inhibitors. - Google Patents
Arylmethylamine derivatives for use as tryptase inhibitors. Download PDFInfo
- Publication number
- OA12274A OA12274A OA1200200357A OA1200200357A OA12274A OA 12274 A OA12274 A OA 12274A OA 1200200357 A OA1200200357 A OA 1200200357A OA 1200200357 A OA1200200357 A OA 1200200357A OA 12274 A OA12274 A OA 12274A
- Authority
- OA
- OAPI
- Prior art keywords
- compound
- blank
- phenyl
- aryl
- heteroaryl
- Prior art date
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- 239000002750 tryptase inhibitor Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 357
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
- 208000006673 asthma Diseases 0.000 claims abstract description 17
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
- -1 aiylalkenyl Chemical group 0.000 claims description 113
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 125000003118 aryl group Chemical group 0.000 claims description 91
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 125000001072 heteroaryl group Chemical group 0.000 claims description 82
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 34
- 102000001400 Tryptase Human genes 0.000 claims description 32
- 108060005989 Tryptase Proteins 0.000 claims description 32
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000001041 indolyl group Chemical group 0.000 claims description 19
- 239000000651 prodrug Substances 0.000 claims description 19
- 229940002612 prodrug Drugs 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 150000001204 N-oxides Chemical class 0.000 claims description 16
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 16
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 16
- 206010003246 arthritis Diseases 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
- 239000003246 corticosteroid Substances 0.000 claims description 14
- 239000000556 agonist Substances 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 claims description 12
- 230000001078 anti-cholinergic effect Effects 0.000 claims description 11
- 125000003435 aroyl group Chemical group 0.000 claims description 11
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 10
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 206010010741 Conjunctivitis Diseases 0.000 claims description 9
- 206010016654 Fibrosis Diseases 0.000 claims description 9
- 206010020751 Hypersensitivity Diseases 0.000 claims description 9
- 230000007815 allergy Effects 0.000 claims description 9
- 230000001668 ameliorated effect Effects 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 230000004761 fibrosis Effects 0.000 claims description 8
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 8
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 8
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims description 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 7
- 230000006378 damage Effects 0.000 claims description 7
- 230000002757 inflammatory effect Effects 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
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- 201000005569 Gout Diseases 0.000 claims description 6
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 208000036142 Viral infection Diseases 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 210000000845 cartilage Anatomy 0.000 claims description 6
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 6
- 208000028169 periodontal disease Diseases 0.000 claims description 6
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 6
- 206010039083 rhinitis Diseases 0.000 claims description 6
- 231100000241 scar Toxicity 0.000 claims description 6
- 230000004614 tumor growth Effects 0.000 claims description 6
- 230000009385 viral infection Effects 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 206010002198 Anaphylactic reaction Diseases 0.000 claims description 5
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 5
- 206010003645 Atopy Diseases 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- 206010020880 Hypertrophy Diseases 0.000 claims description 5
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 5
- 206010028594 Myocardial fibrosis Diseases 0.000 claims description 5
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 5
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 5
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 5
- 206010048873 Traumatic arthritis Diseases 0.000 claims description 5
- 230000036783 anaphylactic response Effects 0.000 claims description 5
- 208000003455 anaphylaxis Diseases 0.000 claims description 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 208000018937 joint inflammation Diseases 0.000 claims description 5
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- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 201000004404 Neurofibroma Diseases 0.000 claims description 4
- 229960001022 fenoterol Drugs 0.000 claims description 4
- 229960000676 flunisolide Drugs 0.000 claims description 4
- 229960002848 formoterol Drugs 0.000 claims description 4
- 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 claims description 4
- 229960001361 ipratropium bromide Drugs 0.000 claims description 4
- 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 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 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 claims description 4
- 229960000195 terbutaline Drugs 0.000 claims description 4
- 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 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 229960000265 cromoglicic acid Drugs 0.000 claims description 3
- 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 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 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 claims description 2
- 229960002117 triamcinolone acetonide Drugs 0.000 claims 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 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 5
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical group N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims 4
- 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 claims 3
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims 2
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- 208000002205 allergic conjunctivitis Diseases 0.000 claims 2
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 claims 2
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- 208000011906 peptic ulcer disease Diseases 0.000 claims 2
- 201000005539 vernal conjunctivitis Diseases 0.000 claims 2
- MCQWELVDXSSVNE-UHFFFAOYSA-N 4-[3-(aminomethyl)phenyl]piperidine-1-carboxylic acid Chemical compound NCC1=CC=CC(C2CCN(CC2)C(O)=O)=C1 MCQWELVDXSSVNE-UHFFFAOYSA-N 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 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 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
- 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 1
- 230000003143 atherosclerotic effect Effects 0.000 claims 1
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- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 1
- 230000001175 peptic effect Effects 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 22
- 229910052786 argon Inorganic materials 0.000 abstract description 3
- 238000000034 method Methods 0.000 description 215
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 213
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 13
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- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 11
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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| GBGB0012362.0A GB0012362D0 (en) | 2000-05-22 | 2000-05-22 | Chemical compounds |
| US09/843,126 US6977263B2 (en) | 2000-05-22 | 2001-04-26 | Chemical compounds |
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| OA12274A true OA12274A (en) | 2006-05-09 |
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| OA1200200357A OA12274A (en) | 2000-05-22 | 2001-04-27 | Arylmethylamine derivatives for use as tryptase inhibitors. |
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| EP (1) | EP1296972B1 (fr) |
| KR (1) | KR100858642B1 (fr) |
| CN (1) | CN1230431C (fr) |
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| US7662826B2 (en) | 2002-04-23 | 2010-02-16 | Shionogi & Co., Ltd. | Pyrazolo [1,5-a] pyrimidine derivative and nad (p) h oxidase inhibitor containing the same |
| EP1567493B1 (fr) | 2002-11-26 | 2009-03-18 | Pfizer Products Inc. | Composes de piperidine phenyle a substitution phenyle s'utilisant comme activateurs de ppar |
| GB0308613D0 (en) * | 2002-12-26 | 2003-05-21 | Aventis Pharma Inc | 4-(3-Aminomethylphenyl) piperidin-1-yl- 5-(2-fluorophenylethynyl) furan-2-yl- methanone as an inhibitor of mast cell tryptase |
| EP3345895B1 (fr) | 2003-04-11 | 2019-12-04 | PTC Therapeutics, Inc. | Composé d'acide benzoïque 1,2,4-oxadiazole et son utilisation pour la suppression non-sens et le traitement de maladies |
| EP1620405A2 (fr) * | 2003-05-01 | 2006-02-01 | Abbott Laboratories | Pyrazole-amides et sulfonamides modulateurs des canaux sodiques |
| SI1867644T1 (sl) | 2003-07-24 | 2009-10-31 | Euro Celtique Sa | Heteroaril-tetrahidropiperidilne spojine, koristne za zdravljenje ali preprečevanje bolečine |
| KR101182690B1 (ko) * | 2004-03-02 | 2012-09-14 | 아벤티스 파마슈티칼스 인크. | 트립타제 억제제의 제조방법 |
| EP1571150A1 (fr) * | 2004-03-02 | 2005-09-07 | Aventis Pharma Deutschland GmbH | Procédé pour la prparation des inhibiteurs de tryptase |
| DE602005017129D1 (de) | 2004-03-22 | 2009-11-26 | Lilly Co Eli | Pyridyl-derivate und ihre verwendung als mglu5-rezeptorantagonisten |
| 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 |
| EP1775298B1 (fr) | 2004-07-01 | 2013-03-20 | Daiichi Sankyo Company, Limited | Dérivé de thiénopyrazole ayant une activité d'inhibition de la pde7 |
| CA2573223C (fr) * | 2004-08-06 | 2013-05-21 | Otsuka Pharmaceutical Co., Ltd. | Compose aromatique |
| WO2006044456A1 (fr) * | 2004-10-13 | 2006-04-27 | Ptc Therapeutics, Inc. | Composes de suppression de non-sens et procedes de leur utilisation |
| JP2008521821A (ja) | 2004-11-29 | 2008-06-26 | バーテックス ファーマシューティカルズ インコーポレイテッド | ムスカリン受容体のモジュレーター |
| CA2587664A1 (fr) * | 2004-12-21 | 2006-06-29 | Devgen N.V. | Composes inter-reagissant avec des canaux ioniques, en particulier avec des canaux ioniques de la famille kv |
| WO2007073432A2 (fr) | 2005-10-11 | 2007-06-28 | Chemocentryx, Inc. | Derives de la piperidine et procedes d’utilisation |
| CA2630468C (fr) | 2005-12-05 | 2015-01-20 | Otsuka Pharmaceutical Co., Ltd. | Medicament |
| RU2462246C2 (ru) | 2006-03-30 | 2012-09-27 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы получения функционального белка из днк, имеющей нонсенс-мутацию, и лечения нарушений, ассоциированных с ней |
| WO2008019302A1 (fr) * | 2006-08-04 | 2008-02-14 | Decode Genetics Ehf | Inhibiteurs pyrazolylphényliques et pyrrolylphényliques de la lta4h pour le traitement de l'inflammation |
| UA95978C2 (ru) | 2006-10-02 | 2011-09-26 | Оцука Фармас'Ютікел Ко., Лтд. | Ингибитор активации stat3/5 |
| TW200833663A (en) * | 2006-12-21 | 2008-08-16 | Astrazeneca Ab | Therapeutic agents |
| WO2008075077A1 (fr) * | 2006-12-21 | 2008-06-26 | Astrazeneca Ab | Dérivés de pipéridine destinés au traitement de l'obésité |
| CA2687931C (fr) | 2007-05-31 | 2016-05-24 | Boehringer Ingelheim International Gmbh | Antagonistes des recepteurs ccr2 et utilisations de ceux-ci |
| US8703119B2 (en) * | 2007-10-05 | 2014-04-22 | Polygene Ltd. | Injectable biodegradable polymer compositions for soft tissue repair and augmentation |
| US8158792B2 (en) | 2007-11-21 | 2012-04-17 | Janssen Pharmaceutica N.V. | Spiropiperidines for use as tryptase inhibitors |
| PT2682120T (pt) * | 2007-12-20 | 2016-11-07 | Teva Pharma | Preparações de laquinimod estáveis |
| MX2011001135A (es) * | 2008-08-22 | 2011-03-21 | Sanofi Aventis | [4-(5-aminometil-2-fluoro-fenil)-piperidin-1-il]-[7-fluoro-1-(2-m etoxi-etil)-4-trifluorometoxi-1h-indol-3-il]-metanona como un inhibidor de la triptasa de mastocitos. |
| CN102256963B (zh) | 2008-12-19 | 2014-06-11 | 贝林格尔.英格海姆国际有限公司 | 作为ccr2受体拮抗剂用于治疗炎症、哮喘和copd的环状嘧啶-4-甲酰胺 |
| FR2955324A1 (fr) * | 2010-01-15 | 2011-07-22 | Sanofi Aventis | [4-(5-aminomethyl-phenyl)-piperidin-1-yl]-1h-indol-3-yl]-methanones disubstituees |
| MX346393B (es) | 2009-12-17 | 2017-03-17 | Centrexion Therapeutics Corp | Nuevos antagonistas del receptor ccr2 y usos de los mismo. |
| RU2012131341A (ru) * | 2009-12-23 | 2014-01-27 | Санофи | Индол-пиперидинилбензиламины как ингибиторы бета-триптазы |
| WO2011079103A1 (fr) * | 2009-12-23 | 2011-06-30 | Sanofi | Spiropipéridine benzylaminesutiles comme inhibitrices de la bêta-tryptase |
| JP2013515723A (ja) * | 2009-12-23 | 2013-05-09 | サノフイ | 炎症性腸疾患の処置 |
| 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 |
| AU2010333893A1 (en) * | 2009-12-23 | 2012-07-19 | Sanofi | [4[4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-(1H-pyrrolo-pyridin-yl)-methanones and synthesis thereof |
| EP3002008B8 (fr) * | 2010-03-11 | 2018-10-24 | New York University | Composés d'amido comme modulateurs roryt et leurs utilisations |
| JP2013526507A (ja) | 2010-05-12 | 2013-06-24 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ccr2受容体アンタゴニスト、その製造方法及び薬物としてのその使用 |
| WO2011141477A1 (fr) | 2010-05-12 | 2011-11-17 | Boehringer Ingelheim International Gmbh | Nouveaux antagonistes du récepteur ccr2, leur procédé de production et leur utilisation en tant que médicaments |
| WO2011144501A1 (fr) | 2010-05-17 | 2011-11-24 | Boehringer Ingelheim International Gmbh | Antagonistes du récepteur ccr2 et leurs utilisations |
| WO2011147772A1 (fr) | 2010-05-25 | 2011-12-01 | Boehringer Ingelheim International Gmbh | Antagonistes du récepteur ccr2 |
| US8962656B2 (en) | 2010-06-01 | 2015-02-24 | Boehringer Ingelheim International Gmbh | CCR2 antagonists |
| WO2013058824A1 (fr) | 2011-04-07 | 2013-04-25 | Cornell University | Monomères aptes à dimériser dans une solution aqueuse et leurs procédés d'utilisation |
| WO2013010839A1 (fr) | 2011-07-15 | 2013-01-24 | Boehringer Ingelheim International Gmbh | Antagonistes de ccr2 nouveaux et sélectifs |
| US10092574B2 (en) | 2012-09-26 | 2018-10-09 | Valorisation-Recherche, Limited Partnership | Inhibitors of polynucleotide repeat-associated RNA foci and uses thereof |
| AU2013353004A1 (en) | 2012-11-30 | 2015-07-09 | Kyowa Hakko Kirin Co., Ltd. | Nitrogen-containing heterocyclic compound |
| TW201441193A (zh) | 2012-12-06 | 2014-11-01 | Kyowa Hakko Kirin Co Ltd | 吡啶酮化合物 |
| JP6744218B2 (ja) | 2013-11-15 | 2020-08-19 | ザ ウィスター インスティテュート オブ アナトミー アンド バイオロジー | Ebna1阻害剤およびそれらの使用方法 |
| JP6946001B2 (ja) | 2014-03-06 | 2021-10-06 | ピーティーシー セラピューティクス, インコーポレイテッド | 薬学的組成物、および1,2,4−オキサジアゾール安息香酸の塩 |
| BR112017024481B1 (pt) | 2015-05-14 | 2020-11-17 | The Wistar Institute Of Anatomy And Biology | composto inibidor de ebna1, composição farmacêutica compreendendo dito composto e usos terapêuticos do mesmo |
| AU2016287584B2 (en) | 2015-07-02 | 2020-03-26 | Centrexion Therapeutics Corporation | (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4yl)methanone citrate |
| HK1251965A1 (zh) | 2015-10-30 | 2019-05-10 | Ptc医疗公司 | 用於治疗癫痫的方法 |
| CN112543634A (zh) | 2018-05-17 | 2021-03-23 | 威斯达研究所 | Ebna1抑制剂晶体形式及其制备和使用方法 |
| US12479816B2 (en) | 2019-02-08 | 2025-11-25 | University of Pittsburgh—of the Commonwealth System of Higher Education | 20-HETE formation inhibitors |
| 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 |
| JP7789016B2 (ja) * | 2020-06-04 | 2025-12-19 | ピライ ユニバーサル エルエルシー | 癌治療における標的化不能kraの標的分解のための新規の小分子 |
| WO2025195508A1 (fr) * | 2024-03-22 | 2025-09-25 | 润尔眼科药物(广州)有限公司 | Composé de phényle hétérocyclique et son utilisation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6673908B1 (en) * | 1999-02-22 | 2004-01-06 | Nuvelo, Inc. | Tumor necrosis factor receptor 2 |
-
2001
- 2001-04-27 AU AU5741301A patent/AU5741301A/xx active Pending
- 2001-04-27 CN CNB018119522A patent/CN1230431C/zh not_active Expired - Lifetime
- 2001-04-27 KR KR1020027015683A patent/KR100858642B1/ko not_active Expired - Fee Related
- 2001-04-27 DZ DZ013347A patent/DZ3347A1/fr active
- 2001-04-27 HU HU0302485A patent/HU227630B1/hu not_active IP Right Cessation
- 2001-04-27 PL PL36049501A patent/PL360495A1/xx not_active Application Discontinuation
- 2001-04-27 AU AU2001257413A patent/AU2001257413B2/en not_active Ceased
- 2001-04-27 OA OA1200200357A patent/OA12274A/en unknown
- 2001-04-27 CA CA2409827A patent/CA2409827C/fr not_active Expired - Lifetime
- 2001-04-27 WO PCT/US2001/013811 patent/WO2001090101A1/fr not_active Ceased
- 2001-04-27 IL IL15283001A patent/IL152830A0/xx unknown
- 2001-04-27 HR HR20020926A patent/HRP20020926B1/xx not_active IP Right Cessation
- 2001-04-27 MX MXPA02011400A patent/MXPA02011400A/es active IP Right Grant
- 2001-04-27 AR ARP010102009A patent/AR033525A1/es active IP Right Grant
- 2001-04-27 EP EP01930925A patent/EP1296972B1/fr not_active Expired - Lifetime
- 2001-04-27 BR BR0111206-6A patent/BR0111206A/pt not_active IP Right Cessation
-
2002
- 2002-11-21 MA MA26919A patent/MA25809A1/fr unknown
- 2002-11-21 NO NO20025601A patent/NO327378B1/no not_active IP Right Cessation
-
2005
- 2005-02-14 US US11/057,809 patent/US20050228018A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1296972B1 (fr) | 2009-12-23 |
| BR0111206A (pt) | 2003-04-15 |
| KR100858642B1 (ko) | 2008-09-17 |
| CA2409827C (fr) | 2010-06-01 |
| CN1439003A (zh) | 2003-08-27 |
| CA2409827A1 (fr) | 2001-11-29 |
| PL360495A1 (en) | 2004-09-06 |
| HU227630B1 (hu) | 2011-10-28 |
| IL152830A0 (en) | 2003-06-24 |
| NO20025601D0 (no) | 2002-11-21 |
| AR033525A1 (es) | 2003-12-26 |
| HUP0302485A2 (hu) | 2003-12-29 |
| CN1230431C (zh) | 2005-12-07 |
| AU5741301A (en) | 2001-12-03 |
| KR20030003294A (ko) | 2003-01-09 |
| EP1296972A1 (fr) | 2003-04-02 |
| MA25809A1 (fr) | 2003-07-01 |
| DZ3347A1 (fr) | 2001-11-29 |
| HRP20020926A2 (en) | 2005-02-28 |
| HUP0302485A3 (en) | 2007-09-28 |
| AU2001257413B2 (en) | 2007-01-18 |
| HK1057899A1 (en) | 2004-04-23 |
| MXPA02011400A (es) | 2003-05-23 |
| NO327378B1 (no) | 2009-06-22 |
| HRP20020926B1 (en) | 2011-01-31 |
| NO20025601L (no) | 2003-01-06 |
| US20050228018A1 (en) | 2005-10-13 |
| WO2001090101A1 (fr) | 2001-11-29 |
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