LT4416B - Nauji izoksazolinai ir izoksazolo fibrinogeno receptoriaus antagonistai - Google Patents

Info

Publication number

LT4416B

LT4416B LT97-182A LT97182A LT4416B LT 4416 B LT4416 B LT 4416B LT 97182 A LT97182 A LT 97182A LT 4416 B LT4416 B LT 4416B

Authority

LT

Lithuania

Prior art keywords

substituted

alkyl

aryl

alkoxy

acetyl

Prior art date

1995-05-31

Links

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• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 title description 9
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 title description 2
• 239000002319 fibrinogen receptor antagonist Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 250
• 238000000034 method Methods 0.000 claims abstract description 69
• 238000011282 treatment Methods 0.000 claims abstract description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
• 208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 18
• 230000008569 process Effects 0.000 claims abstract description 17
• 239000003814 drug Substances 0.000 claims abstract description 14
• 230000009424 thromboembolic effect Effects 0.000 claims abstract description 11
• 230000002537 thrombolytic effect Effects 0.000 claims abstract description 11
• 229940124597 therapeutic agent Drugs 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 229960000103 thrombolytic agent Drugs 0.000 claims abstract description 6
• -1 C 3 cycloalkyl Chemical group 0.000 claims description 694
• 125000003118 aryl group Chemical group 0.000 claims description 342
• 125000000217 alkyl group Chemical group 0.000 claims description 250
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 204
• 229910052736 halogen Inorganic materials 0.000 claims description 179
• 150000002367 halogens Chemical class 0.000 claims description 177
• 229910052739 hydrogen Inorganic materials 0.000 claims description 152
• 229910052799 carbon Inorganic materials 0.000 claims description 150
• 125000000623 heterocyclic group Chemical group 0.000 claims description 146
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 126
• 125000001424 substituent group Chemical group 0.000 claims description 122
• 229910052717 sulfur Inorganic materials 0.000 claims description 84
• 229920006395 saturated elastomer Polymers 0.000 claims description 82
• 125000004076 pyridyl group Chemical group 0.000 claims description 81
• 229910052760 oxygen Inorganic materials 0.000 claims description 76
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 75
• 125000001072 heteroaryl group Chemical group 0.000 claims description 75
• 125000003386 piperidinyl group Chemical group 0.000 claims description 71
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 70
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 68
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 65
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 65
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 60
• 125000005842 heteroatom Chemical group 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 54
• PECYZEOJVXMISF-REOHCLBHSA-N 3-amino-L-alanine Chemical compound [NH3+]C[C@H](N)C([O-])=O PECYZEOJVXMISF-REOHCLBHSA-N 0.000 claims description 52
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 52
• 239000000203 mixture Substances 0.000 claims description 50
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 47
• 239000002253 acid Substances 0.000 claims description 46
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 38
• 125000001041 indolyl group Chemical group 0.000 claims description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
• 125000002757 morpholinyl group Chemical group 0.000 claims description 37
• 125000002541 furyl group Chemical group 0.000 claims description 36
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 36
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 35
• 125000002883 imidazolyl group Chemical group 0.000 claims description 35
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 35
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 35
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 35
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 34
• 125000003971 isoxazolinyl group Chemical group 0.000 claims description 34
• 125000000335 thiazolyl group Chemical group 0.000 claims description 34
• 125000001544 thienyl group Chemical group 0.000 claims description 34
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 33
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 31
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 239000000651 prodrug Substances 0.000 claims description 29
• 229940002612 prodrug Drugs 0.000 claims description 29
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 27
• 230000015572 biosynthetic process Effects 0.000 claims description 27
• 125000005843 halogen group Chemical group 0.000 claims description 27
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 27
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
• 125000001425 triazolyl group Chemical group 0.000 claims description 26
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 25
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 25
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 25
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 25
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 23
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 150000002148 esters Chemical class 0.000 claims description 22
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 20
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 20
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 20
• 239000000460 chlorine Substances 0.000 claims description 19
• 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims description 18
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 18
• 125000005551 pyridylene group Chemical group 0.000 claims description 18
• 208000007536 Thrombosis Diseases 0.000 claims description 17
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 17
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 16
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 16
• WKZMUVPWVULELV-UHFFFAOYSA-N 2,3-diamino-2-(3-methylphenyl)sulfonylpropanoic acid Chemical compound CC1=CC=CC(S(=O)(=O)C(N)(CN)C(O)=O)=C1 WKZMUVPWVULELV-UHFFFAOYSA-N 0.000 claims description 15
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
• 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 14
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 13
• 208000035475 disorder Diseases 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 11
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• 125000006257 n-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 claims description 11
• PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 9
• 229940127218 antiplatelet drug Drugs 0.000 claims description 8
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 8
• FCJUWQYGEFAZIH-UHFFFAOYSA-N deca-2,8-dien-5-one Chemical compound CC=CCCC(=O)CC=CC FCJUWQYGEFAZIH-UHFFFAOYSA-N 0.000 claims description 8
• IMMZBJSASZXRMT-UHFFFAOYSA-N nona-1,7-dien-5-one Chemical compound CC=CCC(=O)CCC=C IMMZBJSASZXRMT-UHFFFAOYSA-N 0.000 claims description 8
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• 238000011321 prophylaxis Methods 0.000 claims description 8
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• VLMGBPKUYHVEHX-UHFFFAOYSA-N undec-2-en-5-one Chemical compound CC=CCC(CCCCCC)=O VLMGBPKUYHVEHX-UHFFFAOYSA-N 0.000 claims description 8
• OCJNIIRPTJXQKA-UHFFFAOYSA-N undeca-2,8-dien-5-one Chemical compound CCC=CCCC(=O)CC=CC OCJNIIRPTJXQKA-UHFFFAOYSA-N 0.000 claims description 8
• ITHQBQNSVXKEII-UHFFFAOYSA-N 3-cyclononylazonane Chemical group C1CCCCCCCC1C1CNCCCCCC1 ITHQBQNSVXKEII-UHFFFAOYSA-N 0.000 claims description 7
• 206010027476 Metastases Diseases 0.000 claims description 7
• 239000003146 anticoagulant agent Substances 0.000 claims description 7
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
• RESIPHIPOBYJRP-UHFFFAOYSA-N dec-2-en-5-one Chemical compound CCCCCC(=O)CC=CC RESIPHIPOBYJRP-UHFFFAOYSA-N 0.000 claims description 7
• HSRHLGBEOQQJKE-UHFFFAOYSA-N dec-8-ene-2,4-dione Chemical compound CC=CCCCC(CC(C)=O)=O HSRHLGBEOQQJKE-UHFFFAOYSA-N 0.000 claims description 7
• 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 7
• HNTDNRUDUVCSAN-UHFFFAOYSA-N non-2-en-5-one Chemical compound CCCCC(=O)CC=CC HNTDNRUDUVCSAN-UHFFFAOYSA-N 0.000 claims description 7
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 7
• PJLLIGDXAQWSHW-UHFFFAOYSA-N undec-9-ene-3,5-dione Chemical compound CCC(=O)CC(=O)CCCC=CC PJLLIGDXAQWSHW-UHFFFAOYSA-N 0.000 claims description 7
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
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• 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 6
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• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
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• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
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• 230000007062 hydrolysis Effects 0.000 claims description 5
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• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
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• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
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• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
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• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 4
• 229940127219 anticoagulant drug Drugs 0.000 claims description 4
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
• 125000000732 arylene group Chemical group 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
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• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
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• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
• BDVQYOQISZTPPG-UHFFFAOYSA-N 2,3-diamino-2-(2,3,5,6-tetramethylphenyl)sulfonylpropanoic acid Chemical compound CC1=CC(C)=C(C)C(S(=O)(=O)C(N)(CN)C(O)=O)=C1C BDVQYOQISZTPPG-UHFFFAOYSA-N 0.000 claims description 2
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• SWPZYSKDTLULFP-UHFFFAOYSA-N 2,3-diamino-2-(2-bromophenyl)sulfonylpropanoic acid Chemical compound NCC(N)(C(O)=O)S(=O)(=O)C1=CC=CC=C1Br SWPZYSKDTLULFP-UHFFFAOYSA-N 0.000 claims description 2
• TVAOLDQXJQAQBW-UHFFFAOYSA-N 2,3-diamino-2-(2-chlorophenyl)sulfonylpropanoic acid Chemical compound NCC(N)(C(O)=O)S(=O)(=O)C1=CC=CC=C1Cl TVAOLDQXJQAQBW-UHFFFAOYSA-N 0.000 claims description 2
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• NTCSFBXNUHGOLD-UHFFFAOYSA-N 2,3-diamino-2-(4-chlorophenyl)sulfonylpropanoic acid Chemical compound NCC(N)(C(O)=O)S(=O)(=O)C1=CC=C(Cl)C=C1 NTCSFBXNUHGOLD-UHFFFAOYSA-N 0.000 claims description 2
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• LAEFJYVIEYGVCA-UHFFFAOYSA-N 2,3-diamino-2-(4-fluorophenyl)sulfonylpropanoic acid Chemical compound NCC(N)(C(O)=O)S(=O)(=O)C1=CC=C(F)C=C1 LAEFJYVIEYGVCA-UHFFFAOYSA-N 0.000 claims description 2
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