RU2628074C2 - ТРИЦИКЛИЧЕСКИЕ АЗОТСОДЕРЖАЩИЕ ПРОИЗВОДНЫЕ ИМИДАЗО[4,5-с]ПИРИДИНА, ОБЛАДАЮЩИЕ ИНГИБИРУЮЩЕЙ АКТИВНОСТЬЮ В ОТНОШЕНИИ РЕЦЕПТОРА ГИСТАМИНА 4 (hH4R) - Google Patents

Info

Publication number

RU2628074C2

RU2628074C2 RU2014115478A RU2014115478A RU2628074C2 RU 2628074 C2 RU2628074 C2 RU 2628074C2 RU 2014115478 A RU2014115478 A RU 2014115478A RU 2014115478 A RU2014115478 A RU 2014115478A RU 2628074 C2 RU2628074 C2 RU 2628074C2

Authority

RU

Russia

Prior art keywords

compound

triazolo

pyrido

pyrazin

amine

Prior art date

2011-09-30

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• 230000002401 inhibitory effect Effects 0.000 title claims description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 71
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 36
• 230000004044 response Effects 0.000 title description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 425
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 61
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 52
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 36
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 30
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
• 125000001424 substituent group Chemical group 0.000 claims abstract description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
• -1 1,4-diazepan-1-yl Chemical group 0.000 claims description 209
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 78
• 229960001340 histamine Drugs 0.000 claims description 39
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 26
• 208000003251 Pruritus Diseases 0.000 claims description 19
• 208000002193 Pain Diseases 0.000 claims description 17
• 230000036407 pain Effects 0.000 claims description 17
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• MMVBKZHQTLDYKG-UHFFFAOYSA-N 1-(12-bromo-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(Br)C=C2N2C1=NN=C2 MMVBKZHQTLDYKG-UHFFFAOYSA-N 0.000 claims description 13
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 13
• 201000008937 atopic dermatitis Diseases 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 230000007803 itching Effects 0.000 claims description 12
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 9
• 208000006673 asthma Diseases 0.000 claims description 9
• 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 8
• 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 8
• 206010028980 Neoplasm Diseases 0.000 claims description 8
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 8
• 201000011510 cancer Diseases 0.000 claims description 8
• 208000027866 inflammatory disease Diseases 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• YPTSSSOPRLTPQF-SNVBAGLBSA-N (3R)-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)-N,N-dimethylpyrrolidin-3-amine Chemical compound C1[C@H](N(C)C)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 YPTSSSOPRLTPQF-SNVBAGLBSA-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
• 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 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 7
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
• 206010010741 Conjunctivitis 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
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
• 206010065390 Inflammatory pain 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
• 206010028735 Nasal congestion Diseases 0.000 claims description 7
• 206010052437 Nasal discomfort 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
• 208000024780 Urticaria Diseases 0.000 claims description 7
• 206010003119 arrhythmia Diseases 0.000 claims description 7
• 230000006793 arrhythmia Effects 0.000 claims description 7
• 208000010668 atopic eczema Diseases 0.000 claims description 7
• 206010009887 colitis Diseases 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 230000004064 dysfunction Effects 0.000 claims description 7
• 206010025135 lupus erythematosus Diseases 0.000 claims description 7
• 230000001404 mediated effect Effects 0.000 claims description 7
• 201000006417 multiple sclerosis Diseases 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
• 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 6
• 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 6
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 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 6
• 208000011231 Crohn disease Diseases 0.000 claims description 6
• 201000004624 Dermatitis Diseases 0.000 claims description 6
• PGQDQCATOKHSPS-UHFFFAOYSA-N N-methyl-1-[12-(trifluoromethyl)-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(NC)CN1C1=NC2=NC=C(C(F)(F)F)C=C2N2C1=NN=C2 PGQDQCATOKHSPS-UHFFFAOYSA-N 0.000 claims description 6
• 208000024376 chronic urticaria Diseases 0.000 claims description 6
• 206010023332 keratitis Diseases 0.000 claims description 6
• 201000010666 keratoconjunctivitis Diseases 0.000 claims description 6
• 201000008482 osteoarthritis Diseases 0.000 claims description 6
• PMFKRDBIRGTURK-UHFFFAOYSA-N 1-(11,12-dichloro-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC(Cl)=C(Cl)C=C2N2C1=NN=C2 PMFKRDBIRGTURK-UHFFFAOYSA-N 0.000 claims description 5
• WIWASHXVJIOYQI-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)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 WIWASHXVJIOYQI-UHFFFAOYSA-N 0.000 claims description 5
• KDXQZJSWOFTCDE-UHFFFAOYSA-N 1-(12-chloro-4-methyl-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Cl)C=C2C2=NC(C)=NN12 KDXQZJSWOFTCDE-UHFFFAOYSA-N 0.000 claims description 5
• SGQVHLLHCYFWEE-UHFFFAOYSA-N 1-(12-iodo-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(I)C=C2N2C1=NN=C2 SGQVHLLHCYFWEE-UHFFFAOYSA-N 0.000 claims description 5
• DVKBWONYFFCHMU-UHFFFAOYSA-N 1-[12-(difluoromethyl)-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(F)F)C=C2N2C1=NN=C2 DVKBWONYFFCHMU-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 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 5
• 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 5
• 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 5
• 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 5
• 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 5
• KJARIWMPADKIOR-UHFFFAOYSA-N 12-iodo-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(I)C=C2N2C1=NN=C2 KJARIWMPADKIOR-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 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 5
• YVRBEXPZVHWNLE-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 Chemical compound C1CN(C)CCN1C1=NC2=NC=CC=C2N2C1=NN=C2 YVRBEXPZVHWNLE-UHFFFAOYSA-N 0.000 claims description 5
• AALXPCRBVDDIHT-SECBINFHSA-N C1[C@H](NC)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 Chemical compound C1[C@H](NC)CCN1C1=NC2=NC=C(Cl)C=C2N2C1=NN=C2 AALXPCRBVDDIHT-SECBINFHSA-N 0.000 claims description 5
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
• 206010015943 Eye inflammation Diseases 0.000 claims description 5
• DSURYHHMNFJXFL-UHFFFAOYSA-N N-methyl-1-(12-methyl-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(NC)CN1C1=NC2=NC=C(C)C=C2N2C1=NN=C2 DSURYHHMNFJXFL-UHFFFAOYSA-N 0.000 claims description 5
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 208000010928 autoimmune thyroid disease Diseases 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
• 208000004296 neuralgia Diseases 0.000 claims description 5
• 208000021722 neuropathic pain Diseases 0.000 claims description 5
• ICGICUHMULRYIQ-UHFFFAOYSA-N 1-(12-bromo-2,3,4,5,8,10-hexazatricyclo[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(Br)C=C2N2C1=NN=N2 ICGICUHMULRYIQ-UHFFFAOYSA-N 0.000 claims description 4
• JJMSSEGSJZIYCX-UHFFFAOYSA-N 1-(12-bromo-2,4,5,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaen-7-yl)-N,N-dimethylazetidin-3-amine Chemical compound C1C(N(C)C)CN1C1=NC2=NC=C(Br)C=C2N2C1=NN=C2 JJMSSEGSJZIYCX-UHFFFAOYSA-N 0.000 claims description 4
• WASIWJNKOCZNFP-LREBCSMRSA-N 1-(12-bromo-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 (2R,3R)-2,3-dihydroxybutanedioic acid Chemical compound O[C@H]([C@@H](O)C(O)=O)C(O)=O.CNC1CN(C1)c1nc2ncc(Br)cc2n2cnnc12 WASIWJNKOCZNFP-LREBCSMRSA-N 0.000 claims description 4
• ZCNIOEAHXVCLCB-UHFFFAOYSA-N 1-(12-bromo-2,5,8,10-tetrazatricyclo[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(Br)C=C2N2C1=NC=C2 ZCNIOEAHXVCLCB-UHFFFAOYSA-N 0.000 claims description 4
• WNPYEYYGAWATBK-UHFFFAOYSA-N 1-(12-bromo-2,5,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),5,7,10,12-pentaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2N2C1=NCC2 WNPYEYYGAWATBK-UHFFFAOYSA-N 0.000 claims description 4
• KEHDFGJYGVMMKU-UHFFFAOYSA-N 1-(12-bromo-4-methyl-2,5,8,10-tetrazatricyclo[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(Br)C=C2N2C1=NC(C)=C2 KEHDFGJYGVMMKU-UHFFFAOYSA-N 0.000 claims description 4
• SAGHZBBBDBALED-UHFFFAOYSA-N 1-(12-bromo-4-methyl-5,6,8,10-tetrazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2C2=CC(C)=NN12 SAGHZBBBDBALED-UHFFFAOYSA-N 0.000 claims description 4
• UFHKHEOAWFCXBP-UHFFFAOYSA-N 1-(12-bromo-6,8,10-triazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=NC=C(Br)C=C2C2=CC=CN12 UFHKHEOAWFCXBP-UHFFFAOYSA-N 0.000 claims description 4
• BBNPHMSHIGXZGV-UHFFFAOYSA-N 1-(12-chloro-2,4,5,8,11-pentazatricyclo[7.4.0.02,6]trideca-1(13),3,5,7,9,11-hexaen-7-yl)-N-methylazetidin-3-amine Chemical compound C1C(NC)CN1C1=NC2=CN=C(Cl)C=C2N2C1=NN=C2 BBNPHMSHIGXZGV-UHFFFAOYSA-N 0.000 claims description 4
• XFMUHEUGQXUGFA-UHFFFAOYSA-N 1-(12-chloro-4-methyl-2,3,5,8,10-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(Cl)C=C2N2C1=NC(C)=N2 XFMUHEUGQXUGFA-UHFFFAOYSA-N 0.000 claims description 4
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