LV12046B - NEW ISOCASZOLINE AND ISOCOXZOL FIBRINOGEN RECEPTOR ANTAGONISTS - Google Patents

Info

Publication number

LV12046B

LV12046B LVP-97-239A LV970239A LV12046B LV 12046 B LV12046 B LV 12046B LV 970239 A LV970239 A LV 970239A LV 12046 B LV12046 B LV 12046B

Authority

LV

Latvia

Prior art keywords

groups

substituted

alkyl

isoxazolin

aryl

Prior art date

1995-05-31

Links

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• 239000002319 fibrinogen receptor antagonist Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 233
• 238000000034 method Methods 0.000 claims abstract description 94
• 238000011282 treatment Methods 0.000 claims abstract description 23
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
• 230000008569 process Effects 0.000 claims abstract description 15
• 239000003814 drug Substances 0.000 claims abstract description 14
• 230000009424 thromboembolic effect Effects 0.000 claims abstract description 13
• 230000002537 thrombolytic effect Effects 0.000 claims abstract description 12
• 208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• 229960000103 thrombolytic agent Drugs 0.000 claims abstract description 8
• 229940124597 therapeutic agent Drugs 0.000 claims abstract 2
• -1 methyloxy- Chemical class 0.000 claims description 609
• 125000003118 aryl group Chemical group 0.000 claims description 345
• 125000000217 alkyl group Chemical group 0.000 claims description 218
• 125000000623 heterocyclic group Chemical group 0.000 claims description 173
• 229910052736 halogen Inorganic materials 0.000 claims description 167
• 150000002367 halogens Chemical class 0.000 claims description 165
• 125000003545 alkoxy group Chemical group 0.000 claims description 156
• 229910052739 hydrogen Inorganic materials 0.000 claims description 146
• 239000001257 hydrogen Substances 0.000 claims description 145
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 126
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 110
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 93
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 81
• 125000004076 pyridyl group Chemical group 0.000 claims description 80
• 125000001072 heteroaryl group Chemical group 0.000 claims description 78
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 77
• 229920006395 saturated elastomer Polymers 0.000 claims description 76
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 73
• 229910052717 sulfur Inorganic materials 0.000 claims description 71
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 70
• 125000003386 piperidinyl group Chemical group 0.000 claims description 67
• 229910052760 oxygen Inorganic materials 0.000 claims description 66
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 64
• 229910052757 nitrogen Inorganic materials 0.000 claims description 64
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 62
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 57
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 53
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 53
• 125000003342 alkenyl group Chemical group 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 49
• 125000001041 indolyl group Chemical group 0.000 claims description 46
• 239000001301 oxygen Substances 0.000 claims description 45
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 43
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
• 125000001424 substituent group Chemical group 0.000 claims description 43
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 41
• 210000001772 blood platelet Anatomy 0.000 claims description 41
• 125000005843 halogen group Chemical group 0.000 claims description 39
• 125000002757 morpholinyl group Chemical group 0.000 claims description 39
• 239000000203 mixture Substances 0.000 claims description 38
• 239000002253 acid Substances 0.000 claims description 37
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 37
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
• 125000002541 furyl group Chemical group 0.000 claims description 36
• 125000005842 heteroatom Chemical group 0.000 claims description 36
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 35
• 125000002883 imidazolyl group Chemical group 0.000 claims description 35
• 125000003971 isoxazolinyl group Chemical group 0.000 claims description 35
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 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
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 34
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 33
• 125000000335 thiazolyl group Chemical group 0.000 claims description 33
• 125000001544 thienyl group Chemical group 0.000 claims description 33
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 32
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 32
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 32
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 31
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 31
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 30
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 30
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 29
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 29
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
• 230000015572 biosynthetic process Effects 0.000 claims description 27
• 125000004429 atom Chemical group 0.000 claims description 26
• 150000002148 esters Chemical class 0.000 claims description 26
• 229940002612 prodrug Drugs 0.000 claims description 26
• 239000000651 prodrug Substances 0.000 claims description 26
• 229910001868 water Inorganic materials 0.000 claims description 25
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 22
• 125000004450 alkenylene group Chemical group 0.000 claims description 22
• 125000002947 alkylene group Chemical group 0.000 claims description 22
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 22
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 21
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 21
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 20
• 125000004419 alkynylene group Chemical group 0.000 claims description 20
• 125000001425 triazolyl group Chemical group 0.000 claims description 20
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 19
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 19
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 19
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000005551 pyridylene group Chemical group 0.000 claims description 18
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 17
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 17
• 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims description 16
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 16
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 15
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 15
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 15
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 15
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 15
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 14
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 14
• 208000007536 Thrombosis Diseases 0.000 claims description 14
• 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 14
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 13
• 150000001412 amines Chemical class 0.000 claims description 13
• 239000003146 anticoagulant agent Substances 0.000 claims description 13
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 125000004926 indolenyl group Chemical group 0.000 claims description 12
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 230000008878 coupling Effects 0.000 claims description 10
• 238000010168 coupling process Methods 0.000 claims description 10
• 238000005859 coupling reaction Methods 0.000 claims description 10
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 9
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
• ITHQBQNSVXKEII-UHFFFAOYSA-N 3-cyclononylazonane Chemical group C1CCCCCCCC1C1CNCCCCCC1 ITHQBQNSVXKEII-UHFFFAOYSA-N 0.000 claims description 8
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 150000007513 acids Chemical class 0.000 claims description 8
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 7
• 208000005189 Embolism Diseases 0.000 claims description 6
• 206010027476 Metastases Diseases 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 6
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 6
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
• PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 5
• 206010020751 Hypersensitivity Diseases 0.000 claims description 5
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 230000007815 allergy Effects 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
• 125000001188 haloalkyl group Chemical group 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• 208000014674 injury Diseases 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 208000010125 myocardial infarction Diseases 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• ATAFDSCDEDHMOK-UHFFFAOYSA-N 3,3-diaminopropanoic acid Chemical compound NC(N)CC(O)=O ATAFDSCDEDHMOK-UHFFFAOYSA-N 0.000 claims description 4
• 101100240521 Caenorhabditis elegans nhr-16 gene Proteins 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 206010012442 Dermatitis contact Diseases 0.000 claims description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• 206010061218 Inflammation 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
• 241000005308 Orsa Species 0.000 claims description 4
• 208000001132 Osteoporosis Diseases 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 206010040070 Septic Shock Diseases 0.000 claims description 4
• 230000002378 acidificating effect Effects 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
• 208000010247 contact dermatitis Diseases 0.000 claims description 4
• 230000009401 metastasis Effects 0.000 claims description 4
• 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 4
• 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 4
• 210000000056 organ Anatomy 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 230000000306 recurrent effect Effects 0.000 claims description 4
• 230000036303 septic shock Effects 0.000 claims description 4
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• 208000007814 Unstable Angina Diseases 0.000 claims description 3
• 208000026935 allergic disease Diseases 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 239000003527 fibrinolytic agent Substances 0.000 claims description 3
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
• MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 3
• 230000003993 interaction Effects 0.000 claims description 3
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 3
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
• DPPGWYPBZGBVGB-UHFFFAOYSA-N 2-amino-2-(aminomethyl)-3-butoxy-3-oxopropanoic acid Chemical compound CCCCOC(=O)C(N)(CN)C(O)=O DPPGWYPBZGBVGB-UHFFFAOYSA-N 0.000 claims description 2
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 150000001721 carbon Chemical group 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 229910052740 iodine Chemical group 0.000 claims description 2
• 238000005304 joining Methods 0.000 claims description 2
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 2
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 2
• 239000000126 substance Substances 0.000 claims description 2
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 60
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 42
• 239000011593 sulfur Substances 0.000 claims 19
• 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 17
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 8
• 239000005977 Ethylene Substances 0.000 claims 8
• 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims 6
• 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 4
• FCJUWQYGEFAZIH-UHFFFAOYSA-N deca-2,8-dien-5-one Chemical compound CC=CCCC(=O)CC=CC FCJUWQYGEFAZIH-UHFFFAOYSA-N 0.000 claims 4
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 3
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 3
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 3
• 229930016911 cinnamic acid Natural products 0.000 claims 3
• 235000013985 cinnamic acid Nutrition 0.000 claims 3
• 239000000571 coke Substances 0.000 claims 3
• HSRHLGBEOQQJKE-UHFFFAOYSA-N dec-8-ene-2,4-dione Chemical compound CC=CCCCC(CC(C)=O)=O HSRHLGBEOQQJKE-UHFFFAOYSA-N 0.000 claims 3
• 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims 3
• 238000004519 manufacturing process Methods 0.000 claims 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 3
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
• HNTDNRUDUVCSAN-UHFFFAOYSA-N non-2-en-5-one Chemical compound CCCCC(=O)CC=CC HNTDNRUDUVCSAN-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• YSFQIJDACSFIOH-UHFFFAOYSA-N 2,2-diaminopropanoic acid Chemical class CC(N)(N)C(O)=O YSFQIJDACSFIOH-UHFFFAOYSA-N 0.000 claims 2
• 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 2
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 2
• 229940077388 benzenesulfonate Drugs 0.000 claims 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
• 238000003776 cleavage reaction Methods 0.000 claims 2
• RESIPHIPOBYJRP-UHFFFAOYSA-N dec-2-en-5-one Chemical compound CCCCCC(=O)CC=CC RESIPHIPOBYJRP-UHFFFAOYSA-N 0.000 claims 2
• 238000003821 enantio-separation Methods 0.000 claims 2
• 230000004968 inflammatory condition Effects 0.000 claims 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
• 238000011321 prophylaxis Methods 0.000 claims 2
• 230000000241 respiratory effect Effects 0.000 claims 2
• 230000007017 scission Effects 0.000 claims 2
• 208000011580 syndromic disease Diseases 0.000 claims 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 2
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