UA74579C2 - Derivatives of arylmethylamine for use as tryptase inhibitors, a pharmaceutical composition based thereon (variants) - Google Patents
Derivatives of arylmethylamine for use as tryptase inhibitors, a pharmaceutical composition based thereon (variants) Download PDFInfo
- Publication number
- UA74579C2 UA74579C2 UA20021210404A UA20021210404A UA74579C2 UA 74579 C2 UA74579 C2 UA 74579C2 UA 20021210404 A UA20021210404 A UA 20021210404A UA 20021210404 A UA20021210404 A UA 20021210404A UA 74579 C2 UA74579 C2 UA 74579C2
- Authority
- UA
- Ukraine
- Prior art keywords
- aryl
- piperidin
- group
- aminomethylphenyl
- alkyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 26
- 239000002750 tryptase inhibitor Substances 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 360
- 208000006673 asthma Diseases 0.000 claims abstract description 13
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 256
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 196
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 183
- -1 substituted Chemical class 0.000 claims description 150
- 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 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 104
- 125000003118 aryl group Chemical group 0.000 claims description 103
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 125000001072 heteroaryl group Chemical group 0.000 claims description 77
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 70
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 58
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 48
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000001041 indolyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- XJLSEXAGTJCILF-RXMQYKEDSA-N (R)-nipecotic acid zwitterion Chemical compound OC(=O)[C@@H]1CCCNC1 XJLSEXAGTJCILF-RXMQYKEDSA-N 0.000 claims description 13
- 206010003246 arthritis Diseases 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
- 125000003435 aroyl group Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 11
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 11
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 10
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 10
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 10
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 230000001078 anti-cholinergic effect Effects 0.000 claims description 7
- 239000003246 corticosteroid Substances 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229940122598 Tryptase inhibitor Drugs 0.000 claims description 6
- 239000000808 adrenergic beta-agonist Substances 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 230000006378 damage Effects 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 5
- 230000003143 atherosclerotic effect Effects 0.000 claims description 5
- 210000000845 cartilage Anatomy 0.000 claims description 5
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 claims description 5
- 230000000451 tissue damage Effects 0.000 claims description 5
- 231100000827 tissue damage Toxicity 0.000 claims description 5
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 206010002198 Anaphylactic reaction Diseases 0.000 claims description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims description 4
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 4
- 206010010741 Conjunctivitis Diseases 0.000 claims description 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 201000005569 Gout Diseases 0.000 claims description 4
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 4
- 206010028594 Myocardial fibrosis Diseases 0.000 claims description 4
- 201000004404 Neurofibroma Diseases 0.000 claims description 4
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 206010039710 Scleroderma Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 125000006383 alkylpyridyl group Chemical group 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 230000036783 anaphylactic response Effects 0.000 claims description 4
- 208000003455 anaphylaxis Diseases 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 230000004761 fibrosis Effects 0.000 claims description 4
- 230000001969 hypertrophic effect Effects 0.000 claims description 4
- 208000018937 joint inflammation Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- 208000011906 peptic ulcer disease Diseases 0.000 claims description 4
- 208000028169 periodontal disease Diseases 0.000 claims description 4
- 231100000241 scar Toxicity 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 3
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 3
- MPDGUJZUVUWNDP-UHFFFAOYSA-N NCC1=CC=CC(C(CC2)CCN2C(O)=O)=C1.NC(C=C1)=CC(Cl)=C1Cl.OC(C(F)(F)F)=O Chemical compound NCC1=CC=CC(C(CC2)CCN2C(O)=O)=C1.NC(C=C1)=CC(Cl)=C1Cl.OC(C(F)(F)F)=O MPDGUJZUVUWNDP-UHFFFAOYSA-N 0.000 claims description 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 206010048873 Traumatic arthritis Diseases 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 201000005404 rubella Diseases 0.000 claims description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 230000004614 tumor growth Effects 0.000 claims description 3
- 201000005539 vernal conjunctivitis Diseases 0.000 claims description 3
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 claims description 2
- PDNHLCRMUIGNBV-UHFFFAOYSA-N 1-pyridin-2-ylethanamine Chemical compound CC(N)C1=CC=CC=N1 PDNHLCRMUIGNBV-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 239000003470 adrenal cortex hormone Substances 0.000 claims description 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 claims description 2
- 229950000210 beclometasone dipropionate Drugs 0.000 claims description 2
- 229960000265 cromoglicic acid Drugs 0.000 claims description 2
- 229960003957 dexamethasone Drugs 0.000 claims description 2
- 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 description 2
- 208000010643 digestive system disease Diseases 0.000 claims description 2
- 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 claims description 2
- 229960001022 fenoterol Drugs 0.000 claims description 2
- 229960000676 flunisolide Drugs 0.000 claims description 2
- 229960002848 formoterol Drugs 0.000 claims description 2
- 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 2
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 2
- 229960001361 ipratropium bromide Drugs 0.000 claims description 2
- 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 2
- 229960002259 nedocromil sodium Drugs 0.000 claims description 2
- 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 2
- 229960002052 salbutamol Drugs 0.000 claims description 2
- 229960000195 terbutaline Drugs 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
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 11
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 233
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
- 239000000126 substance Substances 0.000 description 193
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- 239000000203 mixture Substances 0.000 description 148
- 239000000243 solution Substances 0.000 description 122
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 94
- 238000005481 NMR spectroscopy Methods 0.000 description 90
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 86
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- 239000011541 reaction mixture Substances 0.000 description 66
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- 150000002500 ions Chemical class 0.000 description 62
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 56
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 55
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 31
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- 238000002360 preparation method Methods 0.000 description 19
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- 238000007792 addition Methods 0.000 description 18
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- DXJZBANECHYHRT-UHFFFAOYSA-N 5-(2-phenylethynyl)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(C#CC=2C=CC=CC=2)=C1 DXJZBANECHYHRT-UHFFFAOYSA-N 0.000 description 17
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 17
- 125000006239 protecting group Chemical group 0.000 description 17
- 239000000843 powder Substances 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 15
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- 238000010511 deprotection reaction Methods 0.000 description 14
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Classifications
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- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Virology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0012362.0A GB0012362D0 (en) | 2000-05-22 | 2000-05-22 | Chemical compounds |
PCT/US2001/013811 WO2001090101A1 (en) | 2000-05-22 | 2001-04-27 | Arylmethylamine derivatives for use as tryptase inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
UA74579C2 true UA74579C2 (en) | 2006-01-16 |
Family
ID=9892097
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA20021210404A UA74579C2 (en) | 2000-05-22 | 2001-04-27 | Derivatives of arylmethylamine for use as tryptase inhibitors, a pharmaceutical composition based thereon (variants) |
Country Status (17)
Country | Link |
---|---|
US (1) | US6977263B2 (hr) |
JP (1) | JP4796732B2 (hr) |
CN (1) | CN1740169B (hr) |
AT (1) | ATE452884T1 (hr) |
CR (1) | CR6824A (hr) |
DE (1) | DE60140871D1 (hr) |
DK (1) | DK1296972T3 (hr) |
EA (1) | EA006687B1 (hr) |
ES (1) | ES2337550T3 (hr) |
GB (1) | GB0012362D0 (hr) |
HK (1) | HK1087702A1 (hr) |
IL (1) | IL152830A (hr) |
ME (1) | MEP54608A (hr) |
PT (1) | PT1296972E (hr) |
RS (1) | RS51751B (hr) |
UA (1) | UA74579C2 (hr) |
ZA (1) | ZA200209484B (hr) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP3067053A1 (en) | 2004-10-13 | 2016-09-14 | PTC Therapeutics, Inc. | Compounds for nonsense suppression, and methods for their use |
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 |
CA2674704A1 (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 |
ES2469824T3 (es) * | 2007-11-21 | 2014-06-20 | Janssen Pharmaceutica N.V. | Espiropiperidinas para su uso como inhibidores de la triptasa |
MY150599A (en) * | 2008-08-22 | 2014-01-30 | Sanofi Aventis | [4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-[7-fluoro-1-(2-methoxy-ethyl)-4-trifluoromethoxy-1h-indol-3-yl]-methanone as an inhibitor of mast cell tryptase |
FR2955324A1 (fr) * | 2010-01-15 | 2011-07-22 | Sanofi Aventis | [4-(5-aminomethyl-phenyl)-piperidin-1-yl]-1h-indol-3-yl]-methanones disubstituees |
CA2785439A1 (en) | 2009-12-23 | 2011-06-30 | Sanofi | [4[4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-(1h-pyrrolo-pyridin-yl)-methanones and synthesis thereof |
RS53456B (en) | 2009-12-23 | 2014-12-31 | Sanofi | [4 [4- (5-AMINOMETHYL-2-FLUOR-PHENYL) -PIPERIDIN-1-IL] - (1H-Pyrrolo-pyridin-IL) -METHANONE AND THEIR SYNTHESIS |
AU2010333779A1 (en) * | 2009-12-23 | 2012-07-12 | Sanofi | Indolyl-piperidinyl benzylamines as beta-tryptase inhibitors |
WO2011106334A1 (en) * | 2010-02-24 | 2011-09-01 | Sanofi | Treatment of dermatological allergic conditions |
JP2014512364A (ja) * | 2011-04-07 | 2014-05-22 | コーネル ユニバーシティー | 水溶液中で二量体化できる単量体、およびその使用法 |
AU2012262748B2 (en) * | 2011-05-27 | 2017-03-02 | Lexicon Pharmaceuticals, Inc. | 4H-thieno[3,2-c]chromene-based inhibitors of Notum Pectinacetylesterase and methods of their use |
CA2893115A1 (en) | 2012-11-30 | 2014-06-05 | 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 |
CN105934425B (zh) | 2013-11-15 | 2020-08-07 | 威斯塔解剖学和生物学研究所 | Ebna1抑制剂和其使用方法 |
US11084807B2 (en) | 2016-08-18 | 2021-08-10 | Vidac Pharama 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 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 PT PT01930925T patent/PT1296972E/pt unknown
- 2001-04-27 CN CN2005101063047A patent/CN1740169B/zh not_active Expired - Lifetime
- 2001-04-27 ES ES01930925T patent/ES2337550T3/es not_active Expired - Lifetime
- 2001-04-27 AT AT01930925T patent/ATE452884T1/de active
- 2001-04-27 DK DK01930925.1T patent/DK1296972T3/da active
- 2001-04-27 DE DE60140871T patent/DE60140871D1/de not_active Expired - Lifetime
- 2001-04-27 ME MEP-546/08A patent/MEP54608A/hr unknown
- 2001-04-27 UA UA20021210404A patent/UA74579C2/uk unknown
- 2001-04-27 JP JP2001586288A patent/JP4796732B2/ja not_active Expired - Fee Related
- 2001-04-27 EA EA200201276A patent/EA006687B1/ru not_active IP Right Cessation
- 2001-04-27 RS YU87202A patent/RS51751B/sr 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
-
2006
- 2006-07-14 HK HK06107891.9A patent/HK1087702A1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
ZA200209484B (en) | 2004-02-23 |
ES2337550T3 (es) | 2010-04-27 |
CR6824A (es) | 2008-11-25 |
PT1296972E (pt) | 2010-03-03 |
IL152830A (en) | 2009-11-18 |
US20030187020A1 (en) | 2003-10-02 |
EA200201276A1 (ru) | 2003-06-26 |
GB0012362D0 (en) | 2000-07-12 |
DK1296972T3 (da) | 2010-04-26 |
HK1087702A1 (en) | 2006-10-20 |
EA006687B1 (ru) | 2006-02-24 |
YU87202A (sh) | 2006-05-25 |
JP2004510697A (ja) | 2004-04-08 |
MEP54608A (hr) | 2011-05-10 |
JP4796732B2 (ja) | 2011-10-19 |
ATE452884T1 (de) | 2010-01-15 |
CN1740169B (zh) | 2010-04-21 |
RS51751B (sr) | 2011-12-31 |
DE60140871D1 (de) | 2010-02-04 |
CN1740169A (zh) | 2006-03-01 |
US6977263B2 (en) | 2005-12-20 |
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