EA013184B1 - Конденсированные производные пиразола и способы лечения с их помощью заболеваний, вызванных нарушением обмена веществ - Google Patents

Info

Publication number

EA013184B1

EA013184B1 EA200701361A EA200701361A EA013184B1 EA 013184 B1 EA013184 B1 EA 013184B1 EA 200701361 A EA200701361 A EA 200701361A EA 200701361 A EA200701361 A EA 200701361A EA 013184 B1 EA013184 B1 EA 013184B1

Authority

EA

Eurasian Patent Office

Prior art keywords

tetrahydro

pentalene

compound according

diazacycloprop

carboxylic acid

Prior art date

2004-12-23

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 127
• 238000011282 treatment Methods 0.000 title claims abstract description 45
• 150000003217 pyrazoles Chemical class 0.000 title abstract description 9
• 230000002503 metabolic effect Effects 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 550
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 71
• 150000003839 salts Chemical class 0.000 claims abstract description 68
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 47
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 38
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 34
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 28
• 239000003112 inhibitor Substances 0.000 claims abstract description 27
• 239000000556 agonist Substances 0.000 claims abstract description 25
• 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 24
• 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 22
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 19
• 208000029078 coronary artery disease Diseases 0.000 claims abstract description 19
• 238000003786 synthesis reaction Methods 0.000 claims abstract description 16
• 239000003623 enhancer Substances 0.000 claims abstract description 14
• 239000002464 receptor antagonist Substances 0.000 claims abstract description 13
• 229940044551 receptor antagonist Drugs 0.000 claims abstract description 13
• YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims abstract description 11
• BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims abstract description 11
• PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims abstract description 11
• 229940031439 squalene Drugs 0.000 claims abstract description 11
• TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims abstract description 11
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 9
• 230000015556 catabolic process Effects 0.000 claims abstract description 8
• 229940125753 fibrate Drugs 0.000 claims abstract description 8
• 229940123208 Biguanide Drugs 0.000 claims abstract description 6
• 239000003288 aldose reductase inhibitor Substances 0.000 claims abstract description 6
• -1 methylsulfanylmethyl Chemical group 0.000 claims description 167
• 238000002360 preparation method Methods 0.000 claims description 117
• YZGJIENQZBJQNS-UHFFFAOYSA-N pentalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C21 YZGJIENQZBJQNS-UHFFFAOYSA-N 0.000 claims description 83
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• 201000010099 disease Diseases 0.000 claims description 59
• 239000012453 solvate Substances 0.000 claims description 56
• 229910052799 carbon Inorganic materials 0.000 claims description 44
• 208000030159 metabolic disease Diseases 0.000 claims description 43
• 239000003814 drug Substances 0.000 claims description 39
• 125000004432 carbon atom Chemical group C* 0.000 claims description 38
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
• 241001465754 Metazoa Species 0.000 claims description 28
• 150000004677 hydrates Chemical class 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 239000003795 chemical substances by application Substances 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 150000002367 halogens Chemical class 0.000 claims description 26
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 239000003937 drug carrier Substances 0.000 claims description 18
• 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 17
• 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 17
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 102000004877 Insulin Human genes 0.000 claims description 12
• 108090001061 Insulin Proteins 0.000 claims description 12
• 125000004423 acyloxy group Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 12
• 229940125396 insulin Drugs 0.000 claims description 12
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 11
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
• 229920002554 vinyl polymer Polymers 0.000 claims description 11
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 10
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 9
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 9
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
• 239000005541 ACE inhibitor Substances 0.000 claims description 8
• 241000282412 Homo Species 0.000 claims description 8
• 206010020772 Hypertension Diseases 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 8
• 208000008589 Obesity Diseases 0.000 claims description 8
• 208000006011 Stroke Diseases 0.000 claims description 8
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• CUTZNERBKDMLAP-UHFFFAOYSA-N gtpl5785 Chemical compound C1C2=C(C(=O)O)NN=C2C2CC21 CUTZNERBKDMLAP-UHFFFAOYSA-N 0.000 claims description 8
• 208000019622 heart disease Diseases 0.000 claims description 8
• 235000020824 obesity Nutrition 0.000 claims description 8
• 239000004031 partial agonist Substances 0.000 claims description 8
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 239000005557 antagonist Substances 0.000 claims description 6
• 238000002156 mixing Methods 0.000 claims description 6
• 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 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 229940118148 Aldose reductase inhibitor Drugs 0.000 claims description 4
• XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 4
• 229940123934 Reductase inhibitor Drugs 0.000 claims description 4
• MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims description 4
• DKSPRNJUDCWTID-UHFFFAOYSA-N gtpl5790 Chemical compound C12CC2CC=2C1=NNC=2C=1N=NNN=1 DKSPRNJUDCWTID-UHFFFAOYSA-N 0.000 claims description 4
• 230000028327 secretion Effects 0.000 claims description 4
• RAILBMQEZUOZPY-UHFFFAOYSA-N (+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1h-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester Chemical compound C1C2=C(C(=O)OCC)NN=C2C2C(C)(C)C12 RAILBMQEZUOZPY-UHFFFAOYSA-N 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• UKQFEWRNKWDNBW-UHFFFAOYSA-N 7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-diene-9-carboxylic acid Chemical compound C1C2CC2C2=C(C(=O)O)NN=C21 UKQFEWRNKWDNBW-UHFFFAOYSA-N 0.000 claims description 3
• 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 3
• 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 3
• ZYICRESAGWVMJD-UHFFFAOYSA-N C=1C=CC=CC=1CC(C12)C2CC=2C1=NNC=2C=1N=NNN=1 Chemical compound C=1C=CC=CC=1CC(C12)C2CC=2C1=NNC=2C=1N=NNN=1 ZYICRESAGWVMJD-UHFFFAOYSA-N 0.000 claims description 3
• 229940123464 Thiazolidinedione Drugs 0.000 claims description 3
• ADQXTVQLMDRXSS-UHFFFAOYSA-N chembl2057611 Chemical compound C1C2=C(C(=O)O)NN=C2C2C1C21CCCCC1 ADQXTVQLMDRXSS-UHFFFAOYSA-N 0.000 claims description 3
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 2
• UDQHREJCGBMEQZ-UHFFFAOYSA-N 3-(methylsulfanylmethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CSC)C2CC=2C1=NNC=2C(O)=O UDQHREJCGBMEQZ-UHFFFAOYSA-N 0.000 claims description 2
• UCNBXLZANXGQAD-UHFFFAOYSA-N 3-ethenyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(C=C)C2CC=2C1=NNC=2C=1N=NNN=1 UCNBXLZANXGQAD-UHFFFAOYSA-N 0.000 claims description 2
• SOPWSSMPKDHAFO-UHFFFAOYSA-N 3-methyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(C)C2CC=2C1=NNC=2C=1N=NNN=1 SOPWSSMPKDHAFO-UHFFFAOYSA-N 0.000 claims description 2
• UTILKUIIYSZFGD-UHFFFAOYSA-N 7-(2H-tetrazol-5-yl)spiro[8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-3,1'-cyclohexane] Chemical compound C=12CC(C34CCCCC4)C3C2=NNC=1C1=NN=NN1 UTILKUIIYSZFGD-UHFFFAOYSA-N 0.000 claims description 2
• 229940126062 Compound A Drugs 0.000 claims description 2
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
• SSWAVSFICWGNDI-UHFFFAOYSA-N [7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-dien-3-yl]methanol Chemical compound C12C(CO)C2CC=2C1=NNC=2C=1N=NNN=1 SSWAVSFICWGNDI-UHFFFAOYSA-N 0.000 claims description 2
• CYZOEHLTHQQWSY-UHFFFAOYSA-N chembl2057610 Chemical compound C1C2=C(C(=O)O)NN=C2C2C1C21CCCC1 CYZOEHLTHQQWSY-UHFFFAOYSA-N 0.000 claims description 2
• OTMHRRBDBDERSZ-UHFFFAOYSA-N 3-benzyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12CC3=C(C(=O)O)NN=C3C2C1CC1=CC=CC=C1 OTMHRRBDBDERSZ-UHFFFAOYSA-N 0.000 claims 2
• ZNSMRESAJQMQFB-UHFFFAOYSA-N 3-(2-methylpropyl)-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(CC(C)C)C2CC=2C1=NNC=2C=1N=NNN=1 ZNSMRESAJQMQFB-UHFFFAOYSA-N 0.000 claims 1
• JQOLBGNVBHBYTN-UHFFFAOYSA-N 3-(2-methylpropyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CC(C)C)C2CC=2C1=NNC=2C(O)=O JQOLBGNVBHBYTN-UHFFFAOYSA-N 0.000 claims 1
• UZFHZWKLQQVCHG-UHFFFAOYSA-N 3-(ethoxymethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(COCC)C2CC=2C1=NNC=2C(O)=O UZFHZWKLQQVCHG-UHFFFAOYSA-N 0.000 claims 1
• ODUVQBROUWOBDH-UHFFFAOYSA-N 3-(hydroxymethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CO)C2CC=2C1=NNC=2C(O)=O ODUVQBROUWOBDH-UHFFFAOYSA-N 0.000 claims 1
• SNHAYNGAPALUSS-UHFFFAOYSA-N 3-(methoxymethyl)-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(COC)C2CC=2C1=NNC=2C=1N=NNN=1 SNHAYNGAPALUSS-UHFFFAOYSA-N 0.000 claims 1
• APQANBAOGDTTDE-UHFFFAOYSA-N 3-(methoxymethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(COC)C2CC=2C1=NNC=2C(O)=O APQANBAOGDTTDE-UHFFFAOYSA-N 0.000 claims 1
• XJNZFQMEFRFJIV-UHFFFAOYSA-N 3-(phenoxymethyl)-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12CC(=C(NN=3)C4=NNN=N4)C=3C2C1COC1=CC=CC=C1 XJNZFQMEFRFJIV-UHFFFAOYSA-N 0.000 claims 1
• LUCHJPWHYQGXLE-NSCUHMNNSA-N 3-[(E)-prop-1-enyl]-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(/C=C/C)C2CC=2C1=NNC=2C=1N=NNN=1 LUCHJPWHYQGXLE-NSCUHMNNSA-N 0.000 claims 1
• VIQDOSDFYBSVKH-NSCUHMNNSA-N 3-[(E)-prop-1-enyl]-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(/C=C/C)C2CC=2C1=NNC=2C(O)=O VIQDOSDFYBSVKH-NSCUHMNNSA-N 0.000 claims 1
• VYWKYLOLYLNJFO-UHFFFAOYSA-N 3-butyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(CCCC)C2CC=2C1=NNC=2C=1N=NNN=1 VYWKYLOLYLNJFO-UHFFFAOYSA-N 0.000 claims 1
• HZGMLBXSQLGHIS-UHFFFAOYSA-N 3-butyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CCCC)C2CC=2C1=NNC=2C(O)=O HZGMLBXSQLGHIS-UHFFFAOYSA-N 0.000 claims 1
• BUTFUADABNFVEZ-UHFFFAOYSA-N 3-cyclopropyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C1CC1C1C2C3=NNC(C4=NNN=N4)=C3CC21 BUTFUADABNFVEZ-UHFFFAOYSA-N 0.000 claims 1
• KRGVFHQAOMELTE-UHFFFAOYSA-N 3-cyclopropyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C1C2=C(C(=O)O)NN=C2C2C1C2C1CC1 KRGVFHQAOMELTE-UHFFFAOYSA-N 0.000 claims 1
• RTJPVQFTNJBAAO-UHFFFAOYSA-N 3-ethenyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C1C2=C(C(=O)O)NN=C2C2C(C=C)C12 RTJPVQFTNJBAAO-UHFFFAOYSA-N 0.000 claims 1
• SYZZVQFBZIIAPM-UHFFFAOYSA-N 3-ethyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(CC)C2CC=2C1=NNC=2C=1N=NNN=1 SYZZVQFBZIIAPM-UHFFFAOYSA-N 0.000 claims 1
• TWKUMVSEPLJJQZ-UHFFFAOYSA-N 3-ethyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CC)C2CC=2C1=NNC=2C(O)=O TWKUMVSEPLJJQZ-UHFFFAOYSA-N 0.000 claims 1
• NFZMLDIEJQTJDW-UHFFFAOYSA-N 3-methyl-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-diene-9-carboxylic acid Chemical compound N1C(C(O)=O)=C2C3C(C)C3CC2=N1 NFZMLDIEJQTJDW-UHFFFAOYSA-N 0.000 claims 1
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