DK2760865T3 - New heterocyclic derivatives and their applications - Google Patents

Info

Publication number

DK2760865T3

DK2760865T3 DK12834688.9T DK12834688T DK2760865T3 DK 2760865 T3 DK2760865 T3 DK 2760865T3 DK 12834688 T DK12834688 T DK 12834688T DK 2760865 T3 DK2760865 T3 DK 2760865T3

Authority

DK

Denmark

Prior art keywords

compound

formula

triazolo

pyrido

pyrazin

Prior art date

2011-09-30

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• 125000000623 heterocyclic group Chemical group 0.000 title claims description 57
• 150000001875 compounds Chemical class 0.000 claims description 593
• 238000006243 chemical reaction Methods 0.000 claims description 113
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 82
• 125000005842 heteroatom Chemical group 0.000 claims description 72
• 238000000034 method Methods 0.000 claims description 65
• 229920006395 saturated elastomer Polymers 0.000 claims description 58
• -1 2-bromopyrido [3,2-e] pyrrolo [1,2-c] pyrimidin-6-yl Chemical group 0.000 claims description 56
• 239000000203 mixture Substances 0.000 claims description 55
• 238000006254 arylation reaction Methods 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 43
• 229960001340 histamine Drugs 0.000 claims description 41
• 229910052760 oxygen Inorganic materials 0.000 claims description 38
• 229910052717 sulfur Inorganic materials 0.000 claims description 38
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 37
• 230000026030 halogenation Effects 0.000 claims description 36
• 238000005658 halogenation reaction Methods 0.000 claims description 36
• 238000007363 ring formation reaction Methods 0.000 claims description 31
• 208000003251 Pruritus Diseases 0.000 claims description 26
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• 208000002193 Pain Diseases 0.000 claims description 15
• 230000036407 pain Effects 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 201000008937 atopic dermatitis Diseases 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• BYAVSOKLNYIJSU-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-2,4,5,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=CC=CN=C2N2C1=NN=C2 BYAVSOKLNYIJSU-UHFFFAOYSA-N 0.000 claims description 12
• 230000008569 process Effects 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 208000026935 allergic disease Diseases 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 9
• 208000006673 asthma Diseases 0.000 claims description 9
• 208000010668 atopic eczema Diseases 0.000 claims description 9
• 208000027866 inflammatory disease Diseases 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 206010061218 Inflammation Diseases 0.000 claims description 8
• 206010065390 Inflammatory pain Diseases 0.000 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 8
• 230000010933 acylation Effects 0.000 claims description 8
• 238000005917 acylation reaction Methods 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 201000011510 cancer Diseases 0.000 claims description 8
• 208000024376 chronic urticaria Diseases 0.000 claims description 8
• 230000004054 inflammatory process Effects 0.000 claims description 8
• 208000004296 neuralgia Diseases 0.000 claims description 8
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• 230000003349 osteoarthritic effect Effects 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• HRGIIIWIMGJNML-UHFFFAOYSA-N 1-(12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)azetidin-3-amine Chemical compound C1C(N)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 HRGIIIWIMGJNML-UHFFFAOYSA-N 0.000 claims description 7
• FXKDRFDFQGJXIQ-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 FXKDRFDFQGJXIQ-UHFFFAOYSA-N 0.000 claims description 7
• PVXMKQSOGUMXCY-UHFFFAOYSA-N 12-chloro-7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NN=CN2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 PVXMKQSOGUMXCY-UHFFFAOYSA-N 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 7
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 7
• 206010010741 Conjunctivitis Diseases 0.000 claims description 7
• 208000011231 Crohn disease Diseases 0.000 claims description 7
• 201000004624 Dermatitis Diseases 0.000 claims description 7
• 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 7
• 206010013774 Dry eye Diseases 0.000 claims description 7
• 208000027601 Inner ear disease Diseases 0.000 claims description 7
• 208000000592 Nasal Polyps Diseases 0.000 claims description 7
• 206010060932 Postoperative adhesion Diseases 0.000 claims description 7
• 201000004681 Psoriasis Diseases 0.000 claims description 7
• 206010039710 Scleroderma Diseases 0.000 claims description 7
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
• 208000024780 Urticaria Diseases 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 7
• 208000010928 autoimmune thyroid disease Diseases 0.000 claims description 7
• 206010009887 colitis Diseases 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 206010023332 keratitis Diseases 0.000 claims description 7
• 201000010666 keratoconjunctivitis Diseases 0.000 claims description 7
• 206010025135 lupus erythematosus Diseases 0.000 claims description 7
• 230000001404 mediated effect Effects 0.000 claims description 7
• 208000027491 vestibular disease Diseases 0.000 claims description 7
• MYRLDCFZZRCYHU-UHFFFAOYSA-N 11,12-dichloro-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC(Cl)=C(Cl)C=C2N2C1=NN=C2 MYRLDCFZZRCYHU-UHFFFAOYSA-N 0.000 claims description 6
• HFZKBCNDCXWASD-UHFFFAOYSA-N 11-chloro-7-(4-methylpiperazin-1-yl)-2,4,5,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CN=C2N2C1=NN=C2 HFZKBCNDCXWASD-UHFFFAOYSA-N 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• MPECOUXNLZZITG-UHFFFAOYSA-N 11-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=CC(C)=CN=C2N2C1=NN=C2 MPECOUXNLZZITG-UHFFFAOYSA-N 0.000 claims description 5
• AAGGRTPMBWISNV-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 AAGGRTPMBWISNV-UHFFFAOYSA-N 0.000 claims description 5
• LPKFGUUUKOUOML-UHFFFAOYSA-N 12-bromo-7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NN=CN2C2=CC(Br)=CN=C2N=C1N1CCNCC1 LPKFGUUUKOUOML-UHFFFAOYSA-N 0.000 claims description 5
• QBHCQEPPGQIINH-UHFFFAOYSA-N 12-chloro-11-ethoxy-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C12=NN=CN2C=2C=C(Cl)C(OCC)=NC=2N=C1N1CCN(C)CC1 QBHCQEPPGQIINH-UHFFFAOYSA-N 0.000 claims description 5
• DILJIYOWMILJQS-UHFFFAOYSA-N 12-chloro-4-cyclopropyl-7-piperazin-1-yl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N12N=C(C3CC3)N=C2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 DILJIYOWMILJQS-UHFFFAOYSA-N 0.000 claims description 5
• YYKWNLJXOJLGIA-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene-11-carbonitrile Chemical compound C1CN(C)CCN1C1=NC2=NC(C#N)=C(Cl)C=C2N2C1=NN=C2 YYKWNLJXOJLGIA-UHFFFAOYSA-N 0.000 claims description 5
• XTLJUFPQIDCEOY-UHFFFAOYSA-N 12-chloro-7-[3-(methylamino)azetidin-1-yl]-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene-11-carbonitrile Chemical compound C1C(NC)CN1C1=NC2=NC(C#N)=C(Cl)C=C2N2C1=NN=C2 XTLJUFPQIDCEOY-UHFFFAOYSA-N 0.000 claims description 5
• QHQIWQFWYHVEDH-UHFFFAOYSA-N 12-chloro-7-piperazin-1-yl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N12N=CN=C2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 QHQIWQFWYHVEDH-UHFFFAOYSA-N 0.000 claims description 5
• YHVNTCSNXMQVCT-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene-12-carbonitrile Chemical compound C1CN(C)CCN1C1=NC2=NC=C(C#N)C=C2N2C1=NN=C2 YHVNTCSNXMQVCT-UHFFFAOYSA-N 0.000 claims description 5
• QGNOAFHQPYWXPP-UHFFFAOYSA-N 7-[3-(methylamino)azetidin-1-yl]-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene-12-carbonitrile Chemical compound C1C(NC)CN1C1=NC2=NC=C(C#N)C=C2N2C1=NN=C2 QGNOAFHQPYWXPP-UHFFFAOYSA-N 0.000 claims description 5
• OPNSWNNEUULZMB-UHFFFAOYSA-N 7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene-12-carbonitrile Chemical compound C12=NN=CN2C2=CC(C#N)=CN=C2N=C1N1CCNCC1 OPNSWNNEUULZMB-UHFFFAOYSA-N 0.000 claims description 5
• HURMPUPQNGGCEV-QMMMGPOBSA-N C1CN[C@@H](C)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 Chemical compound C1CN[C@@H](C)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 HURMPUPQNGGCEV-QMMMGPOBSA-N 0.000 claims description 5
• UKFUSIFHDFKEEM-MRVPVSSYSA-N C1[C@H](N)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 Chemical compound C1[C@H](N)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 UKFUSIFHDFKEEM-MRVPVSSYSA-N 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 4
• HCOFYFDBWVOHQU-UHFFFAOYSA-N 1-[12-(furan-2-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl]-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(C=3OC=CC=3)C=C2N2C1=NN=C2 HCOFYFDBWVOHQU-UHFFFAOYSA-N 0.000 claims description 4
• GEZHTOGZKOZVFG-UHFFFAOYSA-N 12-bromo-11-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC(C)=C(Br)C=C2N2C1=NN=C2 GEZHTOGZKOZVFG-UHFFFAOYSA-N 0.000 claims description 4
• YPOGNINXKRNIAQ-UHFFFAOYSA-N 12-bromo-7-(4-methylpiperazin-1-yl)-2,3,4,5,8,10-hexazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Br)C=C2N2C1=NN=N2 YPOGNINXKRNIAQ-UHFFFAOYSA-N 0.000 claims description 4
• CCIBEQZUDVOXRO-UHFFFAOYSA-N 12-bromo-N-(1-methylpyrrolidin-3-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-amine Chemical compound C1N(C)CCC1NC1=NC2=NC=C(Br)C=C2N2C1=NN=C2 CCIBEQZUDVOXRO-UHFFFAOYSA-N 0.000 claims description 4
• SHVWOUAQFIVYLU-UHFFFAOYSA-N 12-chloro-3-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2C SHVWOUAQFIVYLU-UHFFFAOYSA-N 0.000 claims description 4
• ZSHGPJMGIVDHRC-UHFFFAOYSA-N 12-chloro-3-methyl-7-piperazin-1-yl-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound N=1C2=NC=C(Cl)C=C2N2C(C)=NN=C2C=1N1CCNCC1 ZSHGPJMGIVDHRC-UHFFFAOYSA-N 0.000 claims description 4
• NKENEEDRJGMPRZ-UHFFFAOYSA-N 12-chloro-4-(methoxymethyl)-7-(4-methylpiperazin-1-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N12N=C(COC)N=C2C2=CC(Cl)=CN=C2N=C1N1CCN(C)CC1 NKENEEDRJGMPRZ-UHFFFAOYSA-N 0.000 claims description 4
• RETNOQVKSOUDLS-UHFFFAOYSA-N 12-chloro-4-cyclopropyl-7-(4-methylpiperazin-1-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=NC(C3CC3)=NN12 RETNOQVKSOUDLS-UHFFFAOYSA-N 0.000 claims description 4
• GFMFYECOOOAXQM-UHFFFAOYSA-N 12-chloro-4-methyl-7-(4-methylpiperazin-1-yl)-2,3,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NC(C)=N2 GFMFYECOOOAXQM-UHFFFAOYSA-N 0.000 claims description 4
• POAWKHNDGSDQPA-UHFFFAOYSA-N 12-chloro-4-methyl-7-(4-methylpiperazin-1-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=NC(C)=NN12 POAWKHNDGSDQPA-UHFFFAOYSA-N 0.000 claims description 4
• FSZACHAIFINHRW-UHFFFAOYSA-N 12-chloro-4-methyl-7-piperazin-1-yl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N12N=C(C)N=C2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 FSZACHAIFINHRW-UHFFFAOYSA-N 0.000 claims description 4
• NJPYHCCBZPKJRN-UHFFFAOYSA-N 12-chloro-7-(1,4-diazepan-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NN=CN2C2=CC(Cl)=CN=C2N=C1N1CCCNCC1 NJPYHCCBZPKJRN-UHFFFAOYSA-N 0.000 claims description 4
• LQKZUGFOYSPFDU-UHFFFAOYSA-N 12-chloro-7-(3,4,5-trimethylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1C(C)N(C)C(C)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 LQKZUGFOYSPFDU-UHFFFAOYSA-N 0.000 claims description 4
• LCTNQWHKGUJFEH-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,3,4,5,8,10-hexazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=N2 LCTNQWHKGUJFEH-UHFFFAOYSA-N 0.000 claims description 4
• XPZHBXVKJVWYBZ-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NC=C2 XPZHBXVKJVWYBZ-UHFFFAOYSA-N 0.000 claims description 4
• KDUDYHWDYABNRM-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-3,4,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=NN=CN12 KDUDYHWDYABNRM-UHFFFAOYSA-N 0.000 claims description 4
• JAXUIZVKVLIYLB-UHFFFAOYSA-N 12-chloro-7-(4-methylpiperazin-1-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(Cl)C=C2C2=NC=NN12 JAXUIZVKVLIYLB-UHFFFAOYSA-N 0.000 claims description 4
• HUHOQSHFJOASLB-UHFFFAOYSA-N 12-chloro-7-piperazin-1-yl-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C12=NC=CN2C2=CC(Cl)=CN=C2N=C1N1CCNCC1 HUHOQSHFJOASLB-UHFFFAOYSA-N 0.000 claims description 4
• UJXROVRCLVSQDF-UHFFFAOYSA-N 12-methyl-7-(4-methylpiperazin-1-yl)-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN(C)CCN1C1=NC2=NC=C(C)C=C2N2C1=NN=C2 UJXROVRCLVSQDF-UHFFFAOYSA-N 0.000 claims description 4
• AXFIGHQVVHSIJW-UHFFFAOYSA-N 7-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)-12-chloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN2CCCC2CN1C1=NC2=NC=C(Cl)C=C2N2C=NN=C21 AXFIGHQVVHSIJW-UHFFFAOYSA-N 0.000 claims description 4
• YOXGDLHOYVVDST-UHFFFAOYSA-N 7-(3,4,6,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)-12-iodo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene Chemical compound C1CN2CCCC2CN1C1=NC2=NC=C(I)C=C2N2C=NN=C21 YOXGDLHOYVVDST-UHFFFAOYSA-N 0.000 claims description 4
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