BG63876B1 - Инхибитори на клетъчна адхезия - Google Patents

Info

Publication number

BG63876B1

BG63876B1 BG102241A BG10224198A BG63876B1 BG 63876 B1 BG63876 B1 BG 63876B1 BG 102241 A BG102241 A BG 102241A BG 10224198 A BG10224198 A BG 10224198A BG 63876 B1 BG63876 B1 BG 63876B1

Authority

BG

Bulgaria

Prior art keywords

amino

substituted

aryl

group

alkyl

Prior art date

1995-07-11

Links

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• 239000003112 inhibitor Substances 0.000 title claims description 58
• 230000001413 cellular effect Effects 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 229
• 230000005764 inhibitory process Effects 0.000 claims abstract description 14
• 238000011282 treatment Methods 0.000 claims abstract description 11
• 230000002265 prevention Effects 0.000 claims abstract description 4
• -1 hydrazinocarbonyl Chemical group 0.000 claims description 392
• 125000003118 aryl group Chemical group 0.000 claims description 94
• 125000000217 alkyl group Chemical group 0.000 claims description 78
• 230000021164 cell adhesion Effects 0.000 claims description 70
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• 150000001413 amino acids Chemical group 0.000 claims description 37
• 239000002253 acid Substances 0.000 claims description 36
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
• 239000004202 carbamide Substances 0.000 claims description 22
• 125000000524 functional group Chemical group 0.000 claims description 20
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 20
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 19
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 230000002401 inhibitory effect Effects 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 14
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 13
• 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 13
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 13
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 11
• 125000001769 aryl amino group Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 9
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 8
• 125000004442 acylamino group Chemical group 0.000 claims description 8
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 230000028993 immune response Effects 0.000 claims description 8
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 150000003973 alkyl amines Chemical class 0.000 claims description 7
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 7
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 claims description 6
• 206010061218 Inflammation Diseases 0.000 claims description 6
• 125000003435 aroyl group Chemical group 0.000 claims description 6
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 6
• 230000003405 preventing effect Effects 0.000 claims description 6
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 230000006472 autoimmune response Effects 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
• 229960003444 immunosuppressant agent Drugs 0.000 claims description 4
• 239000003018 immunosuppressive agent Substances 0.000 claims description 4
• 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 3
• 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 3
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
• 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 3
• 230000000340 anti-metabolite Effects 0.000 claims description 3
• 229940100197 antimetabolite Drugs 0.000 claims description 3
• 239000002256 antimetabolite Substances 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims description 3
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 3
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 3
• 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 3
• 125000005142 aryl oxy sulfonyl group Chemical group 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• 230000023578 negative regulation of cell adhesion Effects 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 3
• 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
• 201000004681 Psoriasis Diseases 0.000 claims description 2
• 206010052779 Transplant rejections Diseases 0.000 claims description 2
• 230000002378 acidificating effect Effects 0.000 claims description 2
• 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
• 125000005095 alkynylaminocarbonyl group Chemical group 0.000 claims description 2
• 230000003178 anti-diabetic effect Effects 0.000 claims description 2
• 239000000924 antiasthmatic agent Substances 0.000 claims description 2
• 239000003435 antirheumatic agent Substances 0.000 claims description 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
• 229940124630 bronchodilator Drugs 0.000 claims description 2
• 239000000168 bronchodilator agent Substances 0.000 claims description 2
• 239000003246 corticosteroid Substances 0.000 claims description 2
• 229960001334 corticosteroids Drugs 0.000 claims description 2
• 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 2
• 206010012601 diabetes mellitus Diseases 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 239000002955 immunomodulating agent Substances 0.000 claims description 2
• 229940121354 immunomodulator Drugs 0.000 claims description 2
• 201000006417 multiple sclerosis Diseases 0.000 claims description 2
• 229910052720 vanadium Inorganic materials 0.000 claims description 2
• 229930182821 L-proline Natural products 0.000 claims 11
• 229960002429 proline Drugs 0.000 claims 11
• 229950003188 isovaleryl diethylamide Drugs 0.000 claims 10
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 4
• VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical compound NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 claims 4
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 4
• 229940024606 amino acid Drugs 0.000 claims 3
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
• 125000005544 phthalimido group Chemical group 0.000 claims 2
• 229960004295 valine Drugs 0.000 claims 2
• NOFZEIVGJHQATE-UHFFFAOYSA-N 1-phenylmethoxypiperidine-2-carboxylic acid Chemical compound OC(=O)C1CCCCN1OCC1=CC=CC=C1 NOFZEIVGJHQATE-UHFFFAOYSA-N 0.000 claims 1
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
• 125000004911 3,3-dimethylbutylamino group Chemical group CC(CCN*)(C)C 0.000 claims 1
• SITQCJQZAUKWJE-UHFFFAOYSA-N 3-butoxy-4-hydroxy-3-methoxy-2-[(2-methylpropan-2-yl)oxy]-1-phenylmethoxypiperidine-2-carboxylic acid Chemical compound OC1C(C(N(CC1)OCC1=CC=CC=C1)(C(=O)O)OC(C)(C)C)(OCCCC)OC SITQCJQZAUKWJE-UHFFFAOYSA-N 0.000 claims 1
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
• 239000004473 Threonine Substances 0.000 claims 1
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
• 125000004414 alkyl thio group Chemical group 0.000 claims 1
• 230000001088 anti-asthma Effects 0.000 claims 1
• 230000002682 anti-psoriatic effect Effects 0.000 claims 1
• 229940030999 antipsoriatics Drugs 0.000 claims 1
• 125000004093 cyano group Chemical group *C#N 0.000 claims 1
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
• 125000001998 leucyl group Chemical group 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 229960001153 serine Drugs 0.000 claims 1
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 1
• 229960002898 threonine Drugs 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 242
• 230000002757 inflammatory effect Effects 0.000 abstract description 5
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
• 239000000243 solution Substances 0.000 description 56
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• 210000004027 cell Anatomy 0.000 description 43
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
• 239000000047 product Substances 0.000 description 42
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 36
• 239000000203 mixture Substances 0.000 description 34
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• 238000000746 purification Methods 0.000 description 32
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• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
• 230000027455 binding Effects 0.000 description 25
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• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 19
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 19
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
• 235000001014 amino acid Nutrition 0.000 description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
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• 239000012131 assay buffer Substances 0.000 description 14
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• 239000007787 solid Substances 0.000 description 13
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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• 229910052757 nitrogen Inorganic materials 0.000 description 12
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 11
• 239000011347 resin Substances 0.000 description 11
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• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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• RUSLWOBOKXLMRG-UHFFFAOYSA-N 2-[4-(phenylcarbamoylamino)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1NC(=O)NC1=CC=CC=C1 RUSLWOBOKXLMRG-UHFFFAOYSA-N 0.000 description 7
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
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• 125000000335 thiazolyl group Chemical group 0.000 description 7
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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