JP2008509928A - 前駆／幹細胞を動員するためのケモカインの組み合わせ - Google Patents
前駆／幹細胞を動員するためのケモカインの組み合わせ Download PDFInfo
- Publication number
- JP2008509928A JP2008509928A JP2007525838A JP2007525838A JP2008509928A JP 2008509928 A JP2008509928 A JP 2008509928A JP 2007525838 A JP2007525838 A JP 2007525838A JP 2007525838 A JP2007525838 A JP 2007525838A JP 2008509928 A JP2008509928 A JP 2008509928A
- Authority
- JP
- Japan
- Prior art keywords
- pyridinylmethyl
- benzenedimethanamine
- tetrahydro
- methylene
- bis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 210000000130 stem cell Anatomy 0.000 title claims abstract description 92
- 102000019034 Chemokines Human genes 0.000 title description 5
- 108010012236 Chemokines Proteins 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 85
- 102100039398 C-X-C motif chemokine 2 Human genes 0.000 claims abstract description 52
- 101000889128 Homo sapiens C-X-C motif chemokine 2 Proteins 0.000 claims abstract description 52
- 102100031650 C-X-C chemokine receptor type 4 Human genes 0.000 claims abstract description 20
- 101000922348 Homo sapiens C-X-C chemokine receptor type 4 Proteins 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 53
- 229940121384 cxc chemokine receptor type 4 (cxcr4) antagonist Drugs 0.000 claims description 40
- 125000004122 cyclic group Chemical group 0.000 claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
- 125000005842 heteroatom Chemical group 0.000 claims description 33
- 239000002576 chemokine receptor CXCR4 antagonist Substances 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical group 0.000 claims description 26
- 229940002612 prodrug Drugs 0.000 claims description 19
- 239000000651 prodrug Chemical group 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 210000001185 bone marrow Anatomy 0.000 claims description 17
- 210000005259 peripheral blood Anatomy 0.000 claims description 17
- 239000011886 peripheral blood Substances 0.000 claims description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 229920000768 polyamine Polymers 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 125000005647 linker group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 238000002512 chemotherapy Methods 0.000 claims description 8
- 230000003394 haemopoietic effect Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 108010077140 SB251353 Proteins 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 102400000500 GRO-beta(5-73) Human genes 0.000 claims description 5
- 230000008439 repair process Effects 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- 238000011124 ex vivo culture Methods 0.000 claims description 3
- 238000001990 intravenous administration Methods 0.000 claims description 3
- 208000032839 leukemia Diseases 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000001959 radiotherapy Methods 0.000 claims description 3
- 238000007920 subcutaneous administration Methods 0.000 claims description 3
- 230000029663 wound healing Effects 0.000 claims description 3
- 208000032467 Aplastic anaemia Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 208000007502 anemia Diseases 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 230000007547 defect Effects 0.000 claims description 2
- 210000005003 heart tissue Anatomy 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- CWJJHESJXJQCJA-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CNCC1=CC=CC=N1 CWJJHESJXJQCJA-UHFFFAOYSA-N 0.000 claims description 2
- TWTLJZJKDUYSON-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CNCC1=CC=CN=C1 TWTLJZJKDUYSON-UHFFFAOYSA-N 0.000 claims description 2
- RTHCDPLDSUOFCC-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)-1-[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methanamine Chemical compound C=1C=NC=CC=1CNCC(C=C1)=CC=C1CN1CCCNCCNCCCNCC1 RTHCDPLDSUOFCC-UHFFFAOYSA-N 0.000 claims description 2
- 208000004235 neutropenia Diseases 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 210000004976 peripheral blood cell Anatomy 0.000 claims 1
- 206010043554 thrombocytopenia Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 8
- 108010018951 Interleukin-8B Receptors Proteins 0.000 abstract description 4
- 102100028989 C-X-C chemokine receptor type 2 Human genes 0.000 abstract 2
- -1 AMD3100 Chemical class 0.000 description 80
- 125000000217 alkyl group Chemical group 0.000 description 51
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 43
- 210000004027 cell Anatomy 0.000 description 34
- 229910052760 oxygen Inorganic materials 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- 229910052717 sulfur Inorganic materials 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 22
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
- 125000005843 halogen group Chemical group 0.000 description 20
- YIQPUIGJQJDJOS-UHFFFAOYSA-N plerixafor Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CN1CCCNCCNCCCNCC1 YIQPUIGJQJDJOS-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 16
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 16
- 210000004369 blood Anatomy 0.000 description 16
- 239000008280 blood Substances 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 14
- 229960002169 plerixafor Drugs 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 230000002194 synthesizing effect Effects 0.000 description 14
- 102100031573 Hematopoietic progenitor cell antigen CD34 Human genes 0.000 description 13
- 101000777663 Homo sapiens Hematopoietic progenitor cell antigen CD34 Proteins 0.000 description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 12
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 12
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 125000004076 pyridyl group Chemical group 0.000 description 12
- KFRQQIJWOPSAAH-UHFFFAOYSA-N [4-(aminomethyl)-3-(pyridin-2-ylmethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C(CC=2N=CC=CC=2)=C1 KFRQQIJWOPSAAH-UHFFFAOYSA-N 0.000 description 11
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 108010008951 Chemokine CXCL12 Proteins 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 125000000547 substituted alkyl group Chemical group 0.000 description 10
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 9
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 9
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 9
- 102100021669 Stromal cell-derived factor 1 Human genes 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 210000000265 leukocyte Anatomy 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 150000001413 amino acids Chemical group 0.000 description 8
- 150000003857 carboxamides Chemical class 0.000 description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000002883 imidazolyl group Chemical group 0.000 description 7
- 229940076264 interleukin-3 Drugs 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- 150000003852 triazoles Chemical class 0.000 description 7
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
- 108010061299 CXCR4 Receptors Proteins 0.000 description 6
- 102000012000 CXCR4 Receptors Human genes 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 102000000589 Interleukin-1 Human genes 0.000 description 6
- 108010002352 Interleukin-1 Proteins 0.000 description 6
- 108010002386 Interleukin-3 Proteins 0.000 description 6
- 102000000646 Interleukin-3 Human genes 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
- 210000000601 blood cell Anatomy 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 6
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 6
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 238000011476 stem cell transplantation Methods 0.000 description 6
- 150000003536 tetrazoles Chemical class 0.000 description 6
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 5
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 5
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 5
- 102000004890 Interleukin-8 Human genes 0.000 description 5
- 108090001007 Interleukin-8 Proteins 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 5
- 229940096397 interleukin-8 Drugs 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 5
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 4
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 4
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 4
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 4
- 241000725303 Human immunodeficiency virus Species 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 238000002617 apheresis Methods 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 4
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000001483 mobilizing effect Effects 0.000 description 4
- 210000000440 neutrophil Anatomy 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 210000001948 pro-b lymphocyte Anatomy 0.000 description 4
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 4
- 125000005551 pyridylene group Chemical group 0.000 description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 4
- 239000007929 subcutaneous injection Substances 0.000 description 4
- 125000000565 sulfonamide group Chemical class 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 108010009474 Macrophage Inflammatory Proteins Proteins 0.000 description 3
- 102000009571 Macrophage Inflammatory Proteins Human genes 0.000 description 3
- 229910004013 NO 2 Inorganic materials 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 102000036693 Thrombopoietin Human genes 0.000 description 3
- 108010041111 Thrombopoietin Proteins 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- KMLHDSULFOYCCK-UHFFFAOYSA-N [3-(aminomethyl)-2-(pyridin-2-ylmethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1CC1=CC=CC=N1 KMLHDSULFOYCCK-UHFFFAOYSA-N 0.000 description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 description 3
- 125000005015 aryl alkynyl group Chemical group 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 210000002798 bone marrow cell Anatomy 0.000 description 3
- 238000010322 bone marrow transplantation Methods 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000005518 carboxamido group Chemical group 0.000 description 3
- 230000001332 colony forming effect Effects 0.000 description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000004069 differentiation Effects 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 108700017752 gamma-Glu-S-BzCys-PhGly diethyl ester Proteins 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 108010038379 sargramostim Proteins 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000010254 subcutaneous injection Methods 0.000 description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- UFKVRQZMUTURNC-PMACEKPBSA-N (2s)-2-[(2s)-1,4,8,11-tetrazacyclotetradec-2-yl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C1NCCCNCCNCCCN[C@@H]1[C@H]1NCCCNCCNCCCNC1 UFKVRQZMUTURNC-PMACEKPBSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 2
- ZCZVGQCBSJLDDS-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,8-naphthyridine Chemical compound C1=CC=C2CCCNC2=N1 ZCZVGQCBSJLDDS-UHFFFAOYSA-N 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 2
- XEYKWYIXHMEQGM-UHFFFAOYSA-N 1,2-dihydro-1,8-naphthyridine Chemical compound C1=CC=C2C=CCNC2=N1 XEYKWYIXHMEQGM-UHFFFAOYSA-N 0.000 description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 2
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- FEAVXMPFTQROEI-UHFFFAOYSA-N 2h-pyrano[3,2-b]pyridine Chemical group C1=CN=C2C=CCOC2=C1 FEAVXMPFTQROEI-UHFFFAOYSA-N 0.000 description 2
- XNARZJQXBMWIQU-UHFFFAOYSA-N 3,4-dihydro-2h-pyrano[3,2-b]pyridine Chemical group C1=CN=C2CCCOC2=C1 XNARZJQXBMWIQU-UHFFFAOYSA-N 0.000 description 2
- KQMSYFWGOQIZPD-UHFFFAOYSA-N 6-(1,4,8,11-tetrazacyclotetradec-6-yl)-1,4,8,11-tetrazacyclotetradecane Chemical compound C1NCCNCCCNCCNCC1C1CNCCNCCCNCCNC1 KQMSYFWGOQIZPD-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- 0 CC*(CCC1C)CC(CC2)C1NCC2(C)C1(C)CCCCCCCC1 Chemical compound CC*(CCC1C)CC(CC2)C1NCC2(C)C1(C)CCCCCCCC1 0.000 description 2
- 102000016950 Chemokine CXCL1 Human genes 0.000 description 2
- 108010014419 Chemokine CXCL1 Proteins 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010071942 Colony-Stimulating Factors Proteins 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 108010029961 Filgrastim Proteins 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 102100034221 Growth-regulated alpha protein Human genes 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 102000002791 Interleukin-8B Receptors Human genes 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- 108700020796 Oncogene Proteins 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 102100036154 Platelet basic protein Human genes 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 230000000735 allogeneic effect Effects 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 229940125716 antipyretic agent Drugs 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- LMIZORQOLSLQRY-UHFFFAOYSA-N benzene;naphthalene Chemical group C1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 LMIZORQOLSLQRY-UHFFFAOYSA-N 0.000 description 2
- 239000002975 chemoattractant Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000009510 drug design Methods 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- GWEJFLVSOGNLSS-WPFOTENUSA-N ethyl (2s)-2-amino-5-[[(2r)-3-benzylsulfanyl-1-[[(1r)-2-ethoxy-2-oxo-1-phenylethyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoate Chemical compound C([C@H](NC(=O)CC[C@H](N)C(=O)OCC)C(=O)N[C@@H](C(=O)OCC)C=1C=CC=CC=1)SCC1=CC=CC=C1 GWEJFLVSOGNLSS-WPFOTENUSA-N 0.000 description 2
- 238000001943 fluorescence-activated cell sorting Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 108020001507 fusion proteins Proteins 0.000 description 2
- 102000037865 fusion proteins Human genes 0.000 description 2
- CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 2
- 229940080856 gleevec Drugs 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 2
- 230000011132 hemopoiesis Effects 0.000 description 2
- 239000012676 herbal extract Substances 0.000 description 2
- 210000003630 histaminocyte Anatomy 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 229940087875 leukine Drugs 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003550 marker Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- MGQNMYSRDBFUIR-UHFFFAOYSA-N nitro cyanoformate Chemical compound [O-][N+](=O)OC(=O)C#N MGQNMYSRDBFUIR-UHFFFAOYSA-N 0.000 description 2
- 150000002829 nitrogen Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- MIMNFCVQODTQDP-NDLVEFNKSA-N oblimersen Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(S)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 MIMNFCVQODTQDP-NDLVEFNKSA-N 0.000 description 2
- 229960000435 oblimersen Drugs 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- GNGHGFVFONSDEL-UHFFFAOYSA-N pyrazine;pyridazine Chemical compound C1=CC=NN=C1.C1=CN=CC=N1 GNGHGFVFONSDEL-UHFFFAOYSA-N 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- OIMWEHOYHJJPJD-UHFFFAOYSA-N pyridine;pyrimidine Chemical compound C1=CC=NC=C1.C1=CN=CN=C1 OIMWEHOYHJJPJD-UHFFFAOYSA-N 0.000 description 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 229960003433 thalidomide Drugs 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FOSDRKVGBZLRRC-QMMNWOAZSA-N (1r,2r)-1-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1-n-(5,6,7,8-tetrahydroquinolin-8-yl)cyclopentane-1,2-diamine Chemical compound N[C@@H]1CCC[C@H]1N(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 FOSDRKVGBZLRRC-QMMNWOAZSA-N 0.000 description 1
- DEPCBODWMCNAKO-GORYFVAVSA-N (1r,2r)-2-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-2-n-(5,6,7,8-tetrahydroquinolin-8-yl)cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 DEPCBODWMCNAKO-GORYFVAVSA-N 0.000 description 1
- UPXZXNQWHQWURB-UXMRNZNESA-N (2S)-2-amino-N-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-N-(5,6,7,8-tetrahydroquinolin-8-yl)butanediamide Chemical compound C1CCC2=CC=CN=C2C1N(C(=O)[C@H](CC(N)=O)N)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 UPXZXNQWHQWURB-UXMRNZNESA-N 0.000 description 1
- LGLVVVCSQBZONM-HCCLCSBVSA-N (2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentano Chemical compound NC(N)=NCCC[C@@H](NC(=O)C)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(=O)N[C@H](CCCN=C(N)N)C(N)=O LGLVVVCSQBZONM-HCCLCSBVSA-N 0.000 description 1
- FDIAHPIZYUHCDZ-QBHOUYDASA-N (2s)-2,6-diamino-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)hexanamide Chemical compound C1CCC2=CC=CN=C2C1N(C(=O)[C@@H](N)CCCCN)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 FDIAHPIZYUHCDZ-QBHOUYDASA-N 0.000 description 1
- RSGZLNITLGQDQL-XGLRFROISA-N (2s)-2-amino-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)propanamide Chemical compound C1CCC2=CC=CN=C2C1N(C(=O)[C@@H](N)C)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 RSGZLNITLGQDQL-XGLRFROISA-N 0.000 description 1
- JMISKXGBLMKCBE-PMCHYTPCSA-N (2s)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)pyrrolidine-2-carboxamide Chemical compound C=1C=C(CNCC=2N=CC=CC=2)C=CC=1CN(C1C2=NC=CC=C2CCC1)C(=O)[C@@H]1CCCN1 JMISKXGBLMKCBE-PMCHYTPCSA-N 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical group C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- GDAXJBDYNVDMDF-UHFFFAOYSA-N 1,2,4-benzotriazine Chemical compound N1=NC=NC2=CC=CC=C21 GDAXJBDYNVDMDF-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical group C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical group C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- NAPSAMRUCLUKEP-UHFFFAOYSA-N 1,4,7,10,13-pentazacyclohexadecane Chemical compound C1CNCCNCCNCCNCCNC1 NAPSAMRUCLUKEP-UHFFFAOYSA-N 0.000 description 1
- QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 description 1
- HLRWRACNIJFYEO-UHFFFAOYSA-N 1,4,7,10-tetrazacyclotetradecane Chemical compound C1CCNCCNCCNCCNC1 HLRWRACNIJFYEO-UHFFFAOYSA-N 0.000 description 1
- LXUJUJYVZSBOKU-UHFFFAOYSA-N 1,4,7-triazacyclotetradecane Chemical compound C1CCCNCCNCCNCCC1 LXUJUJYVZSBOKU-UHFFFAOYSA-N 0.000 description 1
- MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 description 1
- VQFZKDXSJZVGDA-UHFFFAOYSA-N 1,5,9-triazacyclododecane Chemical compound C1CNCCCNCCCNC1 VQFZKDXSJZVGDA-UHFFFAOYSA-N 0.000 description 1
- AYZNUGGOYICENN-UHFFFAOYSA-N 1-(2-pyridin-2-yl-3,4-dihydro-1h-isoquinolin-5-yl)-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC=NC=1CNCC(C=1CC2)=CC=CC=1CN2C1=CC=CC=N1 AYZNUGGOYICENN-UHFFFAOYSA-N 0.000 description 1
- IMWNCVDLSHMHEL-UHFFFAOYSA-N 1-[1-(1,4,8,11-tetrazacyclotetradec-1-yl)butan-2-yl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C1CCNCCNCCCNCCN1C(CC)CN1CCCNCCNCCCNCC1 IMWNCVDLSHMHEL-UHFFFAOYSA-N 0.000 description 1
- VEEDYUPGPMCQTN-UHFFFAOYSA-N 1-[1-(1,4,8,11-tetrazacyclotetradec-1-yl)pentan-2-yl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C1CCNCCNCCCNCCN1C(CCC)CN1CCCNCCNCCCNCC1 VEEDYUPGPMCQTN-UHFFFAOYSA-N 0.000 description 1
- YUEOTDBNBGFZSZ-UHFFFAOYSA-N 1-[1-(1,4,8,11-tetrazacyclotetradec-1-yl)propan-2-yl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C1CCNCCNCCCNCCN1C(C)CN1CCCNCCNCCCNCC1 YUEOTDBNBGFZSZ-UHFFFAOYSA-N 0.000 description 1
- GVPVISVGQUQSSG-UHFFFAOYSA-N 1-[2-(1,4,8,11-tetrazacyclotetradec-1-yl)ethyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C1CCNCCNCCCNCCN1CCN1CCCNCCNCCCNCC1 GVPVISVGQUQSSG-UHFFFAOYSA-N 0.000 description 1
- UEINORGHTABAFL-UHFFFAOYSA-N 1-[3-[[1h-imidazol-5-ylmethyl(pyridin-2-ylmethyl)amino]methyl]phenyl]-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=CC(CN(CC=2N=CNC=2)CC=2N=CC=CC=2)=CC=1CNCC1=CC=CC=N1 UEINORGHTABAFL-UHFFFAOYSA-N 0.000 description 1
- KBKWSBZLRBYERS-UHFFFAOYSA-N 1-[4-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyrazin-6-ylmethyl)phenyl]-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=C(CN2CC3NCCNC3C2)C=CC=1CNCC1=CC=CC=N1 KBKWSBZLRBYERS-UHFFFAOYSA-N 0.000 description 1
- PMGQWFFOFZQXSJ-UHFFFAOYSA-N 1-[4-(1,7-diazacyclotetradec-4-ylmethyl)phenyl]-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=C(CC2CCNCCCCCCCNCC2)C=CC=1CNCC1=CC=CC=N1 PMGQWFFOFZQXSJ-UHFFFAOYSA-N 0.000 description 1
- ZJBHQRYSMMSJGG-UHFFFAOYSA-N 1-[4-(3,4,4a,5,7,7a-hexahydro-1h-pyrrolo[3,4-c][1,2,5]oxadiazin-6-ylmethyl)phenyl]-n-(pyridin-2-ylmethyl)methanamine Chemical compound C=1C=C(CN2CC3NOCNC3C2)C=CC=1CNCC1=CC=CC=N1 ZJBHQRYSMMSJGG-UHFFFAOYSA-N 0.000 description 1
- GKJYLJLZQLRHLX-UHFFFAOYSA-N 1-[4-[(11,11-difluoro-1,4,7-triazacyclotetradec-4-yl)methyl]phenyl]-n-(pyridin-2-ylmethyl)methanamine Chemical compound C1CNCCCC(F)(F)CCCNCCN1CC(C=C1)=CC=C1CNCC1=CC=CC=N1 GKJYLJLZQLRHLX-UHFFFAOYSA-N 0.000 description 1
- KCIMFODBVYVAJW-UHFFFAOYSA-N 1-[4-[(11-fluoro-1,4,7-triazacyclotetradec-4-yl)methyl]phenyl]-n-(pyridin-2-ylmethyl)methanamine Chemical compound C1CNCCCC(F)CCCNCCN1CC(C=C1)=CC=C1CNCC1=CC=CC=N1 KCIMFODBVYVAJW-UHFFFAOYSA-N 0.000 description 1
- HBJFVMZNYLAQNK-UHFFFAOYSA-N 1-[4-[[(5-methyl-1h-imidazol-4-yl)methyl-(pyridin-2-ylmethyl)amino]methyl]phenyl]-n-(pyridin-2-ylmethyl)methanamine Chemical compound N1=CNC(CN(CC=2C=CC(CNCC=3N=CC=CC=3)=CC=2)CC=2N=CC=CC=2)=C1C HBJFVMZNYLAQNK-UHFFFAOYSA-N 0.000 description 1
- PTDLVNBLFNWNGP-UHFFFAOYSA-N 1-[[2,3,4,6-tetrachloro-5-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound ClC=1C(CN2CCNCCCNCCNCCC2)=C(Cl)C(Cl)=C(Cl)C=1CN1CCCNCCNCCCNCC1 PTDLVNBLFNWNGP-UHFFFAOYSA-N 0.000 description 1
- SEFLKOOVNJZTFY-UHFFFAOYSA-N 1-[[2,3,5,6-tetrafluoro-4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound FC=1C(F)=C(CN2CCNCCCNCCNCCC2)C(F)=C(F)C=1CN1CCCNCCNCCCNCC1 SEFLKOOVNJZTFY-UHFFFAOYSA-N 0.000 description 1
- NYQPBUORMFOXKK-UHFFFAOYSA-N 1-[[2,5-dichloro-4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound ClC=1C=C(CN2CCNCCCNCCNCCC2)C(Cl)=CC=1CN1CCCNCCNCCCNCC1 NYQPBUORMFOXKK-UHFFFAOYSA-N 0.000 description 1
- GBUVEYKYEYRGEU-UHFFFAOYSA-N 1-[[2,5-dimethyl-4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound CC=1C=C(CN2CCNCCCNCCNCCC2)C(C)=CC=1CN1CCCNCCNCCCNCC1 GBUVEYKYEYRGEU-UHFFFAOYSA-N 0.000 description 1
- CGBPRRHXVCXIKY-UHFFFAOYSA-N 1-[[2-bromo-4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C(Br)=CC=1CN1CCCNCCNCCCNCC1 CGBPRRHXVCXIKY-UHFFFAOYSA-N 0.000 description 1
- PXTXSIAYIFRMDE-UHFFFAOYSA-N 1-[[3-(1,4,7,10-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,7,10-tetrazacyclotetradecane Chemical compound C=1C=CC(CN2CCNCCNCCNCCCC2)=CC=1CN1CCCCNCCNCCNCC1 PXTXSIAYIFRMDE-UHFFFAOYSA-N 0.000 description 1
- TWROELGOZKDRSL-UHFFFAOYSA-N 1-[[3-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C=1C=CC(CN2CCNCCCNCCNCCC2)=CC=1CN1CCCNCCNCCCNCC1 TWROELGOZKDRSL-UHFFFAOYSA-N 0.000 description 1
- UPPOFVSOKBVXDP-UHFFFAOYSA-N 1-[[3-(1,5,9-triazacyclododec-1-ylmethyl)phenyl]methyl]-1,5,9-triazacyclododecane Chemical compound C=1C=CC(CN2CCCNCCCNCCC2)=CC=1CN1CCCNCCCNCCC1 UPPOFVSOKBVXDP-UHFFFAOYSA-N 0.000 description 1
- PEVCHIZAJILPKB-UHFFFAOYSA-N 1-[[3-nitro-5-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C=1C(CN2CCNCCCNCCNCCC2)=CC([N+](=O)[O-])=CC=1CN1CCCNCCNCCCNCC1 PEVCHIZAJILPKB-UHFFFAOYSA-N 0.000 description 1
- BNXRQMCWXHZHTF-UHFFFAOYSA-N 1-[[4-(1,4,7,10-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,7,10-tetrazacyclotetradecane Chemical compound C=1C=C(CN2CCNCCNCCNCCCC2)C=CC=1CN1CCCCNCCNCCNCC1 BNXRQMCWXHZHTF-UHFFFAOYSA-N 0.000 description 1
- QNIZOKGSHPITQD-UHFFFAOYSA-N 1-[[4-(1,4,7,11-tetrazacyclotetradec-11-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CN1CCCNCCNCCNCCC1 QNIZOKGSHPITQD-UHFFFAOYSA-N 0.000 description 1
- HFIGZELVHPVTON-UHFFFAOYSA-N 1-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]pyrrolidine-3,4-diamine Chemical compound C1C(N)C(N)CN1CC(C=C1)=CC=C1CNCC1=CC=CC=N1 HFIGZELVHPVTON-UHFFFAOYSA-N 0.000 description 1
- BKJDPXSXCZMISN-UHFFFAOYSA-N 1-[[6-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)pyridin-2-yl]methyl]-1,4,8,11-tetrazacyclotetradecane Chemical compound C=1C=CC(CN2CCNCCCNCCNCCC2)=NC=1CN1CCCNCCNCCCNCC1 BKJDPXSXCZMISN-UHFFFAOYSA-N 0.000 description 1
- LSTOTGFDCJUTLM-UHFFFAOYSA-N 1-benzyl-n-(2-pyridin-2-ylethyl)-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]pyrrolidin-3-amine Chemical compound C=1C=CC(CNCC=2N=CC=CC=2)=CC=1CN(C1CN(CC=2C=CC=CC=2)CC1)CCC1=CC=CC=N1 LSTOTGFDCJUTLM-UHFFFAOYSA-N 0.000 description 1
- MJHXLZLPZMMAIK-UHFFFAOYSA-N 1-benzyl-n-(2-pyridin-2-ylethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]piperidin-4-amine Chemical compound C=1C=C(CNCC=2N=CC=CC=2)C=CC=1CN(C1CCN(CC=2C=CC=CC=2)CC1)CCC1=CC=CC=N1 MJHXLZLPZMMAIK-UHFFFAOYSA-N 0.000 description 1
- VHUNAUGRQAADNH-UHFFFAOYSA-N 1-benzyl-n-(pyridin-2-ylmethyl)-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]pyrrolidin-3-amine Chemical compound C=1C=CC(CN(CC=2N=CC=CC=2)C2CN(CC=3C=CC=CC=3)CC2)=CC=1CNCC1=CC=CC=N1 VHUNAUGRQAADNH-UHFFFAOYSA-N 0.000 description 1
- YOOLUGFXVSTJRL-UHFFFAOYSA-N 1-benzyl-n-(pyridin-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]pyrrolidin-3-amine Chemical compound C=1C=C(CN(CC=2N=CC=CC=2)C2CN(CC=3C=CC=CC=3)CC2)C=CC=1CNCC1=CC=CC=N1 YOOLUGFXVSTJRL-UHFFFAOYSA-N 0.000 description 1
- IWFUTXGNXCUDCF-UHFFFAOYSA-N 1-butyl-n-(2-pyridin-2-ylethyl)-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]piperidin-4-amine Chemical compound C1CN(CCCC)CCC1N(CC=1C=C(CNCC=2N=CC=CC=2)C=CC=1)CCC1=CC=CC=N1 IWFUTXGNXCUDCF-UHFFFAOYSA-N 0.000 description 1
- BJXXQCURPZWADT-UHFFFAOYSA-N 1-methyl-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1CC2=CC=CC=C2C(C)C1NCC(C=C1)=CC=C1CNCC1=CC=CC=N1 BJXXQCURPZWADT-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
- RQVLBXNLNVOMQX-UHFFFAOYSA-N 1-phenyl-3-[2-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]ethyl]urea Chemical compound C=1C=CC=CC=1NC(=O)NCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 RQVLBXNLNVOMQX-UHFFFAOYSA-N 0.000 description 1
- HOXGWRSXHJHFMF-UHFFFAOYSA-N 1-phenyl-n-(pyridin-2-ylmethyl)-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]ethanamine Chemical compound C=1C=CC=CC=1C(C)N(CC=1N=CC=CC=1)CC(C=1)=CC=CC=1CNCC1=CC=CC=N1 HOXGWRSXHJHFMF-UHFFFAOYSA-N 0.000 description 1
- YRMKTQNDPSHONR-UHFFFAOYSA-N 1-phenyl-n-[[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]methanamine Chemical compound C=1C=CC=CC=1CNCC(C=C1)=CC=C1CN1CCCNCCNCCCNCC1 YRMKTQNDPSHONR-UHFFFAOYSA-N 0.000 description 1
- LARAWRPPXPQAFX-UHFFFAOYSA-N 1-pyridin-2-yl-2-[4-[(pyridin-2-ylmethylamino)methyl]phenyl]ethanamine Chemical compound C=1C=CC=NC=1C(N)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 LARAWRPPXPQAFX-UHFFFAOYSA-N 0.000 description 1
- IAGWLDWQRRSAIK-UHFFFAOYSA-N 11-[[4-(1,4,7,11-tetrazacyclotetradec-11-ylmethyl)phenyl]methyl]-1,4,7,11-tetrazacyclotetradecane Chemical compound C=1C=C(CN2CCCNCCNCCNCCC2)C=CC=1CN1CCCNCCNCCNCCC1 IAGWLDWQRRSAIK-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical group C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- UVVVFGSFGDHACP-UHFFFAOYSA-N 1h-indole;1h-pyrrole Chemical compound C=1C=CNC=1.C1=CC=C2NC=CC2=C1 UVVVFGSFGDHACP-UHFFFAOYSA-N 0.000 description 1
- SIQBPWRTJNBBER-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-2-benzazepine Chemical compound C1CCNCC2=CC=CC=C21 SIQBPWRTJNBBER-UHFFFAOYSA-N 0.000 description 1
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 description 1
- YHCUZRJTNSWYCY-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-azepine Chemical compound C1CNCC=CC1 YHCUZRJTNSWYCY-UHFFFAOYSA-N 0.000 description 1
- SMOHMDMTVAYPAI-UHFFFAOYSA-N 2,3,6,7-tetrahydro-1h-azepine Chemical compound C1CC=CCCN1 SMOHMDMTVAYPAI-UHFFFAOYSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- NRYHPSFCBKKDJE-UHFFFAOYSA-N 2-[1-benzyl-4-[pyridin-2-ylmethyl-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]amino]piperidin-3-yl]acetic acid Chemical compound C1CC(N(CC=2C=C(CNCC=3N=CC=CC=3)C=CC=2)CC=2N=CC=CC=2)C(CC(=O)O)CN1CC1=CC=CC=C1 NRYHPSFCBKKDJE-UHFFFAOYSA-N 0.000 description 1
- YGRKCIJFPKKQKJ-UHFFFAOYSA-N 2-[2-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]ethyl]guanidine Chemical compound C1CCC2=CC=CN=C2C1N(CCNC(=N)N)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 YGRKCIJFPKKQKJ-UHFFFAOYSA-N 0.000 description 1
- RTQWWZBSTRGEAV-PKHIMPSTSA-N 2-[[(2s)-2-[bis(carboxymethyl)amino]-3-[4-(methylcarbamoylamino)phenyl]propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound CNC(=O)NC1=CC=C(C[C@@H](CN(CC(C)N(CC(O)=O)CC(O)=O)CC(O)=O)N(CC(O)=O)CC(O)=O)C=C1 RTQWWZBSTRGEAV-PKHIMPSTSA-N 0.000 description 1
- GRZGVUSJSXWTDD-UHFFFAOYSA-N 2-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]guanidine Chemical compound C1=CC(CNC(=N)N)=CC=C1CNCC1=CC=CC=N1 GRZGVUSJSXWTDD-UHFFFAOYSA-N 0.000 description 1
- UQJUPEBNPXJTGH-UHFFFAOYSA-N 2-[[[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methylamino]methyl]aniline Chemical compound NC1=CC=CC=C1CNCC(C=C1)=CC=C1CN1CCNCCCNCCNCCC1 UQJUPEBNPXJTGH-UHFFFAOYSA-N 0.000 description 1
- FBFOFFQQFBONCW-UHFFFAOYSA-N 2-[[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]phenol Chemical compound OC1=CC=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 FBFOFFQQFBONCW-UHFFFAOYSA-N 0.000 description 1
- XPWUCLRKBVXLAK-UHFFFAOYSA-N 2-[[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-yl)amino]methyl]quinolin-8-ol Chemical compound N1=C2C(O)=CC=CC2=CC=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 XPWUCLRKBVXLAK-UHFFFAOYSA-N 0.000 description 1
- VRRHGRADXKUDHV-UHFFFAOYSA-N 2-amino-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)acetamide Chemical compound C1CCC2=CC=CN=C2C1N(C(=O)CN)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 VRRHGRADXKUDHV-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- NOWAALMFKTVKNA-UHFFFAOYSA-N 2-phenyl-n-(pyridin-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2N=CC=CC=2)C2C3=NC(=CC=C3CCC2)C=2C=CC=CC=2)C=CC=1CNCC1=CC=CC=N1 NOWAALMFKTVKNA-UHFFFAOYSA-N 0.000 description 1
- JWJNUFDEINAFJW-UHFFFAOYSA-N 2-phenyl-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CNC2C3=NC(=CC=C3CCC2)C=2C=CC=CC=2)C=CC=1CNCC1=CC=CC=N1 JWJNUFDEINAFJW-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LTEXWUMXSKAKPK-UHFFFAOYSA-N 3-(1-methylpiperidin-3-yl)-n-(pyridin-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]propan-1-amine Chemical compound C1N(C)CCCC1CCCN(CC=1N=CC=CC=1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 LTEXWUMXSKAKPK-UHFFFAOYSA-N 0.000 description 1
- OZFANALXKZFARG-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl OZFANALXKZFARG-UHFFFAOYSA-N 0.000 description 1
- RXYALGAIKPYMGM-UHFFFAOYSA-N 3-[[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CN(CC=2C=CC(CNCC=3N=CC=CC=3)=CC=2)C2C3=NC=CC=C3CCC2)=C1 RXYALGAIKPYMGM-UHFFFAOYSA-N 0.000 description 1
- SKRDQXYTMRDCKD-UHFFFAOYSA-N 3-[[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-yl)amino]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CN(CC=2C=CC(CNCC=3N=CC=CC=3)=CC=2)C2C3=NC=CC=C3CCCC2)=C1 SKRDQXYTMRDCKD-UHFFFAOYSA-N 0.000 description 1
- CJQNJRRDTPULTL-UHFFFAOYSA-N 3-azabicyclo[3.2.1]octane Chemical compound C1C2CCC1CNC2 CJQNJRRDTPULTL-UHFFFAOYSA-N 0.000 description 1
- SELQQIVKCRNKIT-UHFFFAOYSA-N 3-benzyl-1-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1-(5,6,7,8-tetrahydroquinolin-8-yl)urea Chemical compound C=1C=C(CNCC=2N=CC=CC=2)C=CC=1CN(C1C2=NC=CC=C2CCC1)C(=O)NCC1=CC=CC=C1 SELQQIVKCRNKIT-UHFFFAOYSA-N 0.000 description 1
- WVAWOUKVAOMCPU-UHFFFAOYSA-N 3-phenyl-1-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1-(5,6,7,8-tetrahydroquinolin-8-yl)urea Chemical compound C=1C=C(CNCC=2N=CC=CC=2)C=CC=1CN(C1C2=NC=CC=C2CCC1)C(=O)NC1=CC=CC=C1 WVAWOUKVAOMCPU-UHFFFAOYSA-N 0.000 description 1
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
- WRXILBMKDNKDQT-UHFFFAOYSA-N 4-[[[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methylamino]methyl]aniline Chemical compound C1=CC(N)=CC=C1CNCC(C=C1)=CC=C1CN1CCNCCCNCCNCCC1 WRXILBMKDNKDQT-UHFFFAOYSA-N 0.000 description 1
- AUZJRZXMZKCYBE-UHFFFAOYSA-N 4-[[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 AUZJRZXMZKCYBE-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- CQPGDDAKTTWVDD-UHFFFAOYSA-N 4-bromobutanenitrile Chemical compound BrCCCC#N CQPGDDAKTTWVDD-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- DHAXWOQYNNKUAQ-UHFFFAOYSA-N 4-hydroxy-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical group OC(=O)C1=C(O)CCNC1 DHAXWOQYNNKUAQ-UHFFFAOYSA-N 0.000 description 1
- HRVGVJXJUIVOPJ-UHFFFAOYSA-N 4-oxopiperidine-3,5-dicarboxylic acid Chemical compound OC(=O)C1CNCC(C(O)=O)C1=O HRVGVJXJUIVOPJ-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical group C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical group C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-CFWMRBGOSA-N 5j49q6b70f Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 OGWKCGZFUXNPDA-CFWMRBGOSA-N 0.000 description 1
- CSUSIKFJDHUQEQ-UHFFFAOYSA-N 6-methoxy-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1CC2=CC(OC)=CC=C2CC1NCC(C=C1)=CC=C1CNCC1=CC=CC=N1 CSUSIKFJDHUQEQ-UHFFFAOYSA-N 0.000 description 1
- BGNKBUMUVFZBAZ-UHFFFAOYSA-N 7-[1h-imidazol-2-ylmethyl-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]amino]-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1C=2C(O)=CC=CC=2CCC1N(CC=1C=CC(CNCC=2N=CC=CC=2)=CC=1)CC1=NC=CN1 BGNKBUMUVFZBAZ-UHFFFAOYSA-N 0.000 description 1
- DKDLSEPIAWSONV-UHFFFAOYSA-N 7-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methylamino]-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1C=2C(O)=CC=CC=2CCC1NCC(C=C1)=CC=C1CNCC1=CC=CC=N1 DKDLSEPIAWSONV-UHFFFAOYSA-N 0.000 description 1
- HRXBVPDNMXEMSA-UHFFFAOYSA-N 7-methoxy-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1C2=CC(OC)=CC=C2CCC1NCC(C=C1)=CC=C1CNCC1=CC=CC=N1 HRXBVPDNMXEMSA-UHFFFAOYSA-N 0.000 description 1
- DGGKXQQCVPAUEA-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octane Chemical compound C1CCC2CCC1N2 DGGKXQQCVPAUEA-UHFFFAOYSA-N 0.000 description 1
- OTLMPGFPWPEXIK-UHFFFAOYSA-N 8-fluoro-n-(1h-imidazol-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1C=2C(F)=CC=CC=2CCC1N(CC=1C=CC(CNCC=2N=CC=CC=2)=CC=1)CC1=NC=CN1 OTLMPGFPWPEXIK-UHFFFAOYSA-N 0.000 description 1
- XUQNFXXFHDZHNO-UHFFFAOYSA-N 8-fluoro-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1C=2C(F)=CC=CC=2CCC1NCC(C=C1)=CC=C1CNCC1=CC=CC=N1 XUQNFXXFHDZHNO-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 102100030009 Azurocidin Human genes 0.000 description 1
- 101710154607 Azurocidin Proteins 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IYIUQXSYBROSSY-UHFFFAOYSA-N C(=O)(NN([N+](=O)[O-])O)O Chemical compound C(=O)(NN([N+](=O)[O-])O)O IYIUQXSYBROSSY-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 108010048913 CTCE-0214 Proteins 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101001069921 Homo sapiens Growth-regulated alpha protein Proteins 0.000 description 1
- 101000973997 Homo sapiens Nucleosome assembly protein 1-like 4 Proteins 0.000 description 1
- 101000947178 Homo sapiens Platelet basic protein Proteins 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 108010062867 Lenograstim Proteins 0.000 description 1
- 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 1
- 101000746372 Mus musculus Granulocyte-macrophage colony-stimulating factor Proteins 0.000 description 1
- 101100189356 Mus musculus Papolb gene Proteins 0.000 description 1
- 108010056642 N-alpha-acetyl-nona-D-arginine amide acetate Proteins 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- KUUFFMDRRZLVNA-LHEWISCISA-N O=C([C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)C)N(CC1)CCC1N(CC=1C=C(CNCC=2N=CC=CC=2)C=CC=1)CCC1=CC=CC=N1 Chemical compound O=C([C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)C)N(CC1)CCC1N(CC=1C=C(CNCC=2N=CC=CC=2)C=CC=1)CCC1=CC=CC=N1 KUUFFMDRRZLVNA-LHEWISCISA-N 0.000 description 1
- 102000043276 Oncogene Human genes 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 108010025037 T140 peptide Proteins 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- UBJIWAOXPGCEQR-UHFFFAOYSA-N [3-[[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-yl)amino]methyl]indol-1-yl] acetate Chemical compound C12=CC=CC=C2N(OC(=O)C)C=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 UBJIWAOXPGCEQR-UHFFFAOYSA-N 0.000 description 1
- NFKFXRYEPYRXHN-UHFFFAOYSA-N [4-(aminomethyl)-3-(6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-yl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C(C2C3=NC=CC=C3CCCC2)=C1 NFKFXRYEPYRXHN-UHFFFAOYSA-N 0.000 description 1
- ZOTXACXDJNHROX-UHFFFAOYSA-N [Zn].[Zn].C1(=CC=C(C=C1)CN1CCNCCCNCCNCCC1)CN1CCNCCCNCCNCCC1 Chemical compound [Zn].[Zn].C1(=CC=C(C=C1)CN1CCNCCCNCCNCCC1)CN1CCNCCCNCCNCCC1 ZOTXACXDJNHROX-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005137 alkenylsulfonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical group 0.000 description 1
- 125000005139 alkynylsulfonyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229960002616 ancestim Drugs 0.000 description 1
- 108700024685 ancestim Proteins 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005251 aryl acyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000003651 basophil Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 210000004271 bone marrow stromal cell Anatomy 0.000 description 1
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- KPUFNLPDWGSMGZ-UHFFFAOYSA-N carboxy(nitro)azanide Chemical group OC(=O)[N-][N+]([O-])=O KPUFNLPDWGSMGZ-UHFFFAOYSA-N 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000011712 cell development Effects 0.000 description 1
- 230000011748 cell maturation Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- WDDPHFBMKLOVOX-AYQXTPAHSA-N clofarabine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F WDDPHFBMKLOVOX-AYQXTPAHSA-N 0.000 description 1
- 229960000928 clofarabine Drugs 0.000 description 1
- 230000005757 colony formation Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 108010035886 connective tissue-activating peptide Proteins 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- KATXJJSCAPBIOB-UHFFFAOYSA-N cyclotetradecane Chemical compound C1CCCCCCCCCCCCC1 KATXJJSCAPBIOB-UHFFFAOYSA-N 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 108010017271 denileukin diftitox Proteins 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000003979 eosinophil Anatomy 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- QQLSDQQQTYRPOD-UHFFFAOYSA-N ethyl 4-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 QQLSDQQQTYRPOD-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000009231 family therapy Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 229960004177 filgrastim Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229940044658 gallium nitrate Drugs 0.000 description 1
- 229950001987 garnocestim Drugs 0.000 description 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
- 229960005277 gemcitabine Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 210000003714 granulocyte Anatomy 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 210000000777 hematopoietic system Anatomy 0.000 description 1
- 208000018706 hematopoietic system disease Diseases 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 229960001001 ibritumomab tiuxetan Drugs 0.000 description 1
- 229960002411 imatinib Drugs 0.000 description 1
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011813 knockout mouse model Methods 0.000 description 1
- GOTYRUGSSMKFNF-UHFFFAOYSA-N lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 210000003593 megakaryocyte Anatomy 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 108010032806 molgramostim Proteins 0.000 description 1
- 229960003063 molgramostim Drugs 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 210000003643 myeloid progenitor cell Anatomy 0.000 description 1
- 108010059631 myelopoietin Proteins 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- YORNHNMWEWVKTM-UHFFFAOYSA-N n'-(1-methyl-3,4-dihydro-2h-quinolin-8-yl)-n-(pyridin-2-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]ethane-1,2-diamine Chemical compound C=12N(C)CCCC2=CC=CC=1N(CC=1C=CC(CNCC=2N=CC=CC=2)=CC=1)CCNCC1=CC=CC=N1 YORNHNMWEWVKTM-UHFFFAOYSA-N 0.000 description 1
- WVLHHLRVNDMIAR-UHFFFAOYSA-N n'-(1h-benzimidazol-2-ylmethyl)-n'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine Chemical compound C1CCC2=CC=CN=C2C1N(CCCCN)CC1=NC2=CC=CC=C2N1 WVLHHLRVNDMIAR-UHFFFAOYSA-N 0.000 description 1
- OBCGVCHGTISUSB-UHFFFAOYSA-N n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound C1CCC2=CC=CN=C2C1N(CCN)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 OBCGVCHGTISUSB-UHFFFAOYSA-N 0.000 description 1
- TWAJZSBBOJFYRN-UHFFFAOYSA-N n,n-bis[(2-methoxyphenyl)methyl]-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound COC1=CC=CC=C1CN(CC=1C(=CC=CC=1)OC)CCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 TWAJZSBBOJFYRN-UHFFFAOYSA-N 0.000 description 1
- ODIMBPKBZOUTLX-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C=1C=C(CN(CC=2C=C3OCOC3=CC=2)C2C3=NC=CC=C3CCCC2)C=CC=1CNCC1=CC=CC=N1 ODIMBPKBZOUTLX-UHFFFAOYSA-N 0.000 description 1
- YPTODVXKEJXEET-UHFFFAOYSA-N n-(1h-benzimidazol-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC3=CC=CC=C3N=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 YPTODVXKEJXEET-UHFFFAOYSA-N 0.000 description 1
- RDVFBUBHPDUNRW-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-7-methoxy-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1C2=CC(OC)=CC=C2CCC1N(CC=1C=CC(CNCC=2N=CC=CC=2)=CC=1)CC1=NC=CN1 RDVFBUBHPDUNRW-UHFFFAOYSA-N 0.000 description 1
- CVCOZIAFFAJQFJ-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-n'-(1-methyl-3,4-dihydro-2h-quinolin-8-yl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]ethane-1,2-diamine Chemical compound C=12N(C)CCCC2=CC=CC=1N(CC=1C=CC(CNCC=2N=CC=CC=2)=CC=1)CCNCC1=NC=CN1 CVCOZIAFFAJQFJ-UHFFFAOYSA-N 0.000 description 1
- JNSXPMQONUZISJ-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(1,2,3,4-tetrahydronaphthalen-1-yl)ethane-1,2-diamine Chemical compound N=1C=CNC=1CNCCN(C1C2=CC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 JNSXPMQONUZISJ-UHFFFAOYSA-N 0.000 description 1
- WEZLIYLAGMXZGO-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound N=1C=CNC=1CNCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 WEZLIYLAGMXZGO-UHFFFAOYSA-N 0.000 description 1
- AAEQSVMSSUKQLP-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-5-amine Chemical compound C=1C=C(CN(CC=2NC=CN=2)C2C3=CC=CN=C3CCC2)C=CC=1CNCC1=CC=CC=N1 AAEQSVMSSUKQLP-UHFFFAOYSA-N 0.000 description 1
- CFZVQPIGMZCPFB-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C=1C=C(CN(CC=2NC=CN=2)C2CC3=NC=CC=C3CC2)C=CC=1CNCC1=CC=CC=N1 CFZVQPIGMZCPFB-UHFFFAOYSA-N 0.000 description 1
- UWDNZPLJAOUFIF-UHFFFAOYSA-N n-(1h-imidazol-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC=CN=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 UWDNZPLJAOUFIF-UHFFFAOYSA-N 0.000 description 1
- WOCZPNMRMRTPNS-UHFFFAOYSA-N n-(1h-imidazol-5-ylmethyl)-2-pyridin-2-yl-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]ethanamine Chemical compound C=1NC=NC=1CN(CC=1C=C(CNCC=2N=CC=CC=2)C=CC=1)CCC1=CC=CC=N1 WOCZPNMRMRTPNS-UHFFFAOYSA-N 0.000 description 1
- HUQUYFJWQMETSC-UHFFFAOYSA-N n-(1h-imidazol-5-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound C=1NC=NC=1CNCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 HUQUYFJWQMETSC-UHFFFAOYSA-N 0.000 description 1
- ABWLCCXVRITGNR-UHFFFAOYSA-N n-(1h-imidazol-5-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2N=CNC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 ABWLCCXVRITGNR-UHFFFAOYSA-N 0.000 description 1
- IKTGDJUQIPTXPP-UHFFFAOYSA-N n-(1h-pyrazol-5-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC2=NNC=C2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 IKTGDJUQIPTXPP-UHFFFAOYSA-N 0.000 description 1
- AYKPCBBGHOBDKZ-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C=1C=C(CN(CC=2C=C3OCCOC3=CC=2)C2C3=NC=CC=C3CCCC2)C=CC=1CNCC1=CC=CC=N1 AYKPCBBGHOBDKZ-UHFFFAOYSA-N 0.000 description 1
- GVCLHOJGDIBACL-UHFFFAOYSA-N n-(2-methylpropyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound C1CCC2=CC=CN=C2C1N(CCNCC(C)C)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 GVCLHOJGDIBACL-UHFFFAOYSA-N 0.000 description 1
- PMNHJMNUXJHRCG-UHFFFAOYSA-N n-(2-phenylethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CNCC=2N=CC=CC=2)C=CC=1CN(C1C2=NC=CC=C2CCC1)CCC1=CC=CC=C1 PMNHJMNUXJHRCG-UHFFFAOYSA-N 0.000 description 1
- QYISGBVHZGPVRO-UHFFFAOYSA-N n-(2-phenylmethoxyethyl)-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=CC=CC=1COCCN(C1C2=NC=CC=C2CCC1)CC(C=1)=CC=CC=1CNCC1=CC=CC=N1 QYISGBVHZGPVRO-UHFFFAOYSA-N 0.000 description 1
- MXYQOQASCBNUDZ-UHFFFAOYSA-N n-(2-pyridin-2-ylethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CNCC=2N=CC=CC=2)C=CC=1CN(C1C2=NC=CC=C2CCC1)CCC1=CC=CC=N1 MXYQOQASCBNUDZ-UHFFFAOYSA-N 0.000 description 1
- VFVPTCKHUQJLLP-UHFFFAOYSA-N n-(3-phenylpropyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=CC=CC=1CCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 VFVPTCKHUQJLLP-UHFFFAOYSA-N 0.000 description 1
- LHDIGVATAPZAFK-UHFFFAOYSA-N n-(3h-imidazo[4,5-c]pyridin-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC3=CC=NC=C3N=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 LHDIGVATAPZAFK-UHFFFAOYSA-N 0.000 description 1
- JDLVDJOZOJUSKB-UHFFFAOYSA-N n-(furan-2-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound C=1C=COC=1CNCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 JDLVDJOZOJUSKB-UHFFFAOYSA-N 0.000 description 1
- IIBURQNHZQCMKA-UHFFFAOYSA-N n-(furan-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2OC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 IIBURQNHZQCMKA-UHFFFAOYSA-N 0.000 description 1
- IAKOZGHZGQFGTL-UHFFFAOYSA-N n-(naphthalen-2-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound C=1C=C2C=CC=CC2=CC=1CNCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 IAKOZGHZGQFGTL-UHFFFAOYSA-N 0.000 description 1
- VXQJFGISVRSRNN-UHFFFAOYSA-N n-(naphthalen-2-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)propane-1,3-diamine Chemical compound C=1C=C2C=CC=CC2=CC=1CNCCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 VXQJFGISVRSRNN-UHFFFAOYSA-N 0.000 description 1
- DTLFISKHFHZEGV-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound C=1C=CC=NC=1CNCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 DTLFISKHFHZEGV-UHFFFAOYSA-N 0.000 description 1
- UUAATDVFOQOPPY-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C=1C=C(CN(CC=2N=CC=CC=2)C2C3=CC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 UUAATDVFOQOPPY-UHFFFAOYSA-N 0.000 description 1
- ZOEJTQLRFVTEMH-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1-(5,6,7,8-tetrahydroquinolin-8-yl)methanamine Chemical compound C=1C=C(CN(CC2C3=NC=CC=C3CCC2)CC=2N=CC=CC=2)C=CC=1CNCC1=CC=CC=N1 ZOEJTQLRFVTEMH-UHFFFAOYSA-N 0.000 description 1
- WBIDRLRQDSWWJR-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2N=CC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 WBIDRLRQDSWWJR-UHFFFAOYSA-N 0.000 description 1
- FFNBWWNCOBAIHU-UHFFFAOYSA-N n-(pyridin-3-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2C=NC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 FFNBWWNCOBAIHU-UHFFFAOYSA-N 0.000 description 1
- IMOJNKRLXGTIIV-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2C=CN=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 IMOJNKRLXGTIIV-UHFFFAOYSA-N 0.000 description 1
- XEIPYOIQVUXTCC-UHFFFAOYSA-N n-[(1-methyl-3h-pyrazol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound CN1C=CCN1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 XEIPYOIQVUXTCC-UHFFFAOYSA-N 0.000 description 1
- MAFZBZUSYWGNLM-UHFFFAOYSA-N n-[(1-methylbenzimidazol-2-yl)methyl]-2-pyridin-2-yl-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]ethanamine Chemical compound N=1C2=CC=CC=C2N(C)C=1CN(CC=1C=CC(CNCC=2N=CC=CC=2)=CC=1)CCC1=CC=CC=N1 MAFZBZUSYWGNLM-UHFFFAOYSA-N 0.000 description 1
- WWCSYVUBGHAPBM-UHFFFAOYSA-N n-[(1-methylbenzimidazol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N=1C2=CC=CC=C2N(C)C=1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 WWCSYVUBGHAPBM-UHFFFAOYSA-N 0.000 description 1
- PGPVOBTXVGCPBN-UHFFFAOYSA-N n-[(1-methylbenzimidazol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound N=1C2=CC=CC=C2N(C)C=1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 PGPVOBTXVGCPBN-UHFFFAOYSA-N 0.000 description 1
- FGQINHRQJRJTAG-UHFFFAOYSA-N n-[(1-methylindol-3-yl)methyl]-2-pyridin-2-yl-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]ethanamine Chemical compound C12=CC=CC=C2N(C)C=C1CN(CC=1C=C(CNCC=2N=CC=CC=2)C=CC=1)CCC1=CC=CC=N1 FGQINHRQJRJTAG-UHFFFAOYSA-N 0.000 description 1
- NZQJPPFVFICWOR-UHFFFAOYSA-N n-[(1-methylpyrrol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN1C=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 NZQJPPFVFICWOR-UHFFFAOYSA-N 0.000 description 1
- VYJDSQYBDAIXLY-UHFFFAOYSA-N n-[(2,3-dimethoxyphenyl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound COC1=CC=CC(CN(CC=2C=CC(CNCC=3N=CC=CC=3)=CC=2)C2C3=NC=CC=C3CCC2)=C1OC VYJDSQYBDAIXLY-UHFFFAOYSA-N 0.000 description 1
- RIQPBQKUXWVZKM-UHFFFAOYSA-N n-[(2,4-difluorophenyl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound FC1=CC(F)=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 RIQPBQKUXWVZKM-UHFFFAOYSA-N 0.000 description 1
- PVNSFRWJGQXGPB-UHFFFAOYSA-N n-[(2,6-difluorophenyl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound FC1=CC=CC(F)=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 PVNSFRWJGQXGPB-UHFFFAOYSA-N 0.000 description 1
- PIGANJHCFCHTSW-UHFFFAOYSA-N n-[(2,6-difluorophenyl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound FC1=CC=CC(F)=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 PIGANJHCFCHTSW-UHFFFAOYSA-N 0.000 description 1
- GQCANGSJLVHDAO-UHFFFAOYSA-N n-[(2-ethoxynaphthalen-1-yl)methyl]-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CCOC1=CC=C2C=CC=CC2=C1CN(C1C2=NC=CC=C2CCC1)CC(C=1)=CC=CC=1CNCC1=CC=CC=N1 GQCANGSJLVHDAO-UHFFFAOYSA-N 0.000 description 1
- BMMFYDSMCVZFMW-UHFFFAOYSA-N n-[(2-ethoxyphenyl)methyl]-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound CCOC1=CC=CC=C1CN(C1C2=NC=CC=C2CCCC1)CC1=CC=CC(CNCC=2N=CC=CC=2)=C1 BMMFYDSMCVZFMW-UHFFFAOYSA-N 0.000 description 1
- JSQYNPNXPHQYDW-UHFFFAOYSA-N n-[(2-methoxyphenyl)methyl]-n-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound COC1=CC=CC=C1CN(C1C2=NC=CC=C2CCC1)CC1=CC=CC(CNCC=2N=CC=CC=2)=C1 JSQYNPNXPHQYDW-UHFFFAOYSA-N 0.000 description 1
- SNAPQAHESGUMBX-UHFFFAOYSA-N n-[(2-phenyl-1h-indol-3-yl)methyl]-2-pyridin-2-yl-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]ethanamine Chemical compound C=1C=CC=CC=1C=1NC2=CC=CC=C2C=1CN(CC=1C=CC(CNCC=2N=CC=CC=2)=CC=1)CCC1=CC=CC=N1 SNAPQAHESGUMBX-UHFFFAOYSA-N 0.000 description 1
- VKDHBCBGBPBMJS-BHVANESWSA-N n-[(2s)-3-methyl-1-oxo-1-[4-[2-pyridin-2-ylethyl-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]amino]piperidin-1-yl]butan-2-yl]benzamide Chemical compound N([C@@H](C(C)C)C(=O)N1CCC(CC1)N(CCC=1N=CC=CC=1)CC=1C=C(CNCC=2N=CC=CC=2)C=CC=1)C(=O)C1=CC=CC=C1 VKDHBCBGBPBMJS-BHVANESWSA-N 0.000 description 1
- UYMDKKVILQGGBT-ZTOMLWHTSA-N n-[(2s)-5-(diaminomethylideneamino)-1-[[(1s)-1-naphthalen-1-ylethyl]amino]-1-oxopentan-2-yl]-4-[(pyridin-2-ylmethylamino)methyl]benzamide Chemical compound N([C@@H](CCCN=C(N)N)C(=O)N[C@@H](C)C=1C2=CC=CC=C2C=CC=1)C(=O)C(C=C1)=CC=C1CNCC1=CC=CC=N1 UYMDKKVILQGGBT-ZTOMLWHTSA-N 0.000 description 1
- HBQUSQLYWUYSNZ-UHFFFAOYSA-N n-[(3,5-dimethyl-2-phenyl-1,3-dihydropyrazol-4-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CC1N(C=2C=CC=CC=2)NC(C)=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 HBQUSQLYWUYSNZ-UHFFFAOYSA-N 0.000 description 1
- PUPNXLZCDGNKTF-UHFFFAOYSA-N n-[(4-methoxy-3-phenylmethoxyphenyl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C1=C(OCC=2C=CC=CC=2)C(OC)=CC=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 PUPNXLZCDGNKTF-UHFFFAOYSA-N 0.000 description 1
- RLNGHKMZTQTXKO-UHFFFAOYSA-N n-[(4-propoxyphenyl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C1=CC(OCCC)=CC=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 RLNGHKMZTQTXKO-UHFFFAOYSA-N 0.000 description 1
- CKLHJTZOTREWRN-UHFFFAOYSA-N n-[(5,6-dimethyl-1h-benzimidazol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 CKLHJTZOTREWRN-UHFFFAOYSA-N 0.000 description 1
- RMCATXSKXPBDNF-UHFFFAOYSA-N n-[(5-ethylthiophen-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound S1C(CC)=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 RMCATXSKXPBDNF-UHFFFAOYSA-N 0.000 description 1
- LBFSIGBHEKWLNG-UHFFFAOYSA-N n-[(5-ethylthiophen-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound S1C(CC)=CC=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 LBFSIGBHEKWLNG-UHFFFAOYSA-N 0.000 description 1
- IGOIWNVJKFRSGJ-UHFFFAOYSA-N n-[(5-phenyl-1h-imidazol-2-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC=C(N=2)C=2C=CC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 IGOIWNVJKFRSGJ-UHFFFAOYSA-N 0.000 description 1
- YFYZCQQXITUSEF-UHFFFAOYSA-N n-[(6-chloro-1,3-benzodioxol-5-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound ClC1=CC=2OCOC=2C=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 YFYZCQQXITUSEF-UHFFFAOYSA-N 0.000 description 1
- QSQHWRVQHDVQKG-UHFFFAOYSA-N n-[(7-methoxy-1,3-benzodioxol-5-yl)methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=2OCOC=2C(OC)=CC=1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 QSQHWRVQHDVQKG-UHFFFAOYSA-N 0.000 description 1
- JXPSYJDUAHOGQX-UHFFFAOYSA-N n-[2-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]ethyl]naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 JXPSYJDUAHOGQX-UHFFFAOYSA-N 0.000 description 1
- SKZLIWLJXMQJGM-UHFFFAOYSA-N n-[3-(1-methylpyrazol-3-yl)propyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound CN1C=CC(CCCN(CC=2C=CC(CNCC=3N=CC=CC=3)=CC=2)C2C3=NC=CC=C3CCC2)=N1 SKZLIWLJXMQJGM-UHFFFAOYSA-N 0.000 description 1
- XPMDBFDZSFFEKB-UHFFFAOYSA-N n-[4-[[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(5,6,7,8-tetrahydroquinolin-8-yl)amino]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 XPMDBFDZSFFEKB-UHFFFAOYSA-N 0.000 description 1
- SQUVPSMZPTVSQB-UHFFFAOYSA-N n-[4-[[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl-(6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-yl)amino]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 SQUVPSMZPTVSQB-UHFFFAOYSA-N 0.000 description 1
- XESSIXSRVRDHAB-UHFFFAOYSA-N n-[4-[pyridin-2-ylmethyl-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]amino]piperidin-1-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NN(CC1)CCC1N(CC=1N=CC=CC=1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 XESSIXSRVRDHAB-UHFFFAOYSA-N 0.000 description 1
- MRNPTLSXBJDDLB-UHFFFAOYSA-N n-[4-acetamido-1-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]pyrrolidin-3-yl]acetamide Chemical compound C1C(NC(C)=O)C(NC(=O)C)CN1CC(C=C1)=CC=C1CNCC1=CC=CC=N1 MRNPTLSXBJDDLB-UHFFFAOYSA-N 0.000 description 1
- XBIQMGKMRSHTED-UHFFFAOYSA-N n-[[2-(difluoromethoxy)phenyl]methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound FC(F)OC1=CC=CC=C1CN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 XBIQMGKMRSHTED-UHFFFAOYSA-N 0.000 description 1
- VAEHEHHOXXADLX-UHFFFAOYSA-N n-[[2-(difluoromethoxy)phenyl]methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound FC(F)OC1=CC=CC=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 VAEHEHHOXXADLX-UHFFFAOYSA-N 0.000 description 1
- UJUKLPCFHRHJHI-UHFFFAOYSA-N n-[[4-(aminomethyl)phenyl]methyl]-8-methyl-n-(pyridin-2-ylmethyl)-8-azabicyclo[3.2.1]octan-3-amine Chemical compound CN1C(C2)CCC1CC2N(CC=1N=CC=CC=1)CC1=CC=C(CN)C=C1 UJUKLPCFHRHJHI-UHFFFAOYSA-N 0.000 description 1
- LEAHSUUCRLJLTN-UHFFFAOYSA-N n-[[4-(dimethylamino)phenyl]methyl]-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C1=CC(N(C)C)=CC=C1CN(C1C2=NC=CC=C2CCCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 LEAHSUUCRLJLTN-UHFFFAOYSA-N 0.000 description 1
- HVYYCEMREPWDCX-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C=1C=C(CNC2C3=CC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 HVYYCEMREPWDCX-UHFFFAOYSA-N 0.000 description 1
- UMQKDDXFDPRWKQ-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-1,2,3,4-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CNC=2C=3NCCCC=3C=CC=2)C=CC=1CNCC1=CC=CC=N1 UMQKDDXFDPRWKQ-UHFFFAOYSA-N 0.000 description 1
- BOSHJQMZFHOIEM-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-5-amine Chemical compound C=1C=C(CNC2C3=CC=CN=C3CCC2)C=CC=1CNCC1=CC=CC=N1 BOSHJQMZFHOIEM-UHFFFAOYSA-N 0.000 description 1
- OWQFWPLLANSQQV-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C=1C=C(CNC2CC3=NC=CC=C3CC2)C=CC=1CNCC1=CC=CC=N1 OWQFWPLLANSQQV-UHFFFAOYSA-N 0.000 description 1
- NVQPVMGRKSAJCF-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CNC2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 NVQPVMGRKSAJCF-UHFFFAOYSA-N 0.000 description 1
- PETRZIRWQJDWID-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-9-amine Chemical compound C=1C=C(CNC2C3=NC=CC=C3CCCC2)C=CC=1CNCC1=CC=CC=N1 PETRZIRWQJDWID-UHFFFAOYSA-N 0.000 description 1
- GSCRMXPAVFDDAJ-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-6,7-dihydro-5h-cyclopenta[b]pyridin-7-amine Chemical compound C=1C=C(CNC2C3=NC=CC=C3CC2)C=CC=1CNCC1=CC=CC=N1 GSCRMXPAVFDDAJ-UHFFFAOYSA-N 0.000 description 1
- MQVBXWKLLOZAJE-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(1,3-thiazol-2-ylmethyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2SC=CN=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 MQVBXWKLLOZAJE-UHFFFAOYSA-N 0.000 description 1
- PNDMWKHXWDAICF-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(1h-pyrrol-2-ylmethyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2NC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 PNDMWKHXWDAICF-UHFFFAOYSA-N 0.000 description 1
- RKEIPHNVBYPWQO-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)-1,3-benzoxazol-2-amine Chemical compound C=1C=C(CN(C2C3=NC=CC=C3CCC2)C=2OC3=CC=CC=C3N=2)C=CC=1CNCC1=CC=CC=N1 RKEIPHNVBYPWQO-UHFFFAOYSA-N 0.000 description 1
- QAGAPIORZOUMSX-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)N(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 QAGAPIORZOUMSX-UHFFFAOYSA-N 0.000 description 1
- UWAKJWARIZWAPY-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)N(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 UWAKJWARIZWAPY-UHFFFAOYSA-N 0.000 description 1
- KNFODAPPVSMDKV-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(5,6,7,8-tetrahydroquinolin-8-yl)pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)N(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 KNFODAPPVSMDKV-UHFFFAOYSA-N 0.000 description 1
- JIDPWUUAOHRSGW-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(quinolin-2-ylmethyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2N=C3C=CC=CC3=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 JIDPWUUAOHRSGW-UHFFFAOYSA-N 0.000 description 1
- LHLSXJIWISDKGG-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(quinolin-3-ylmethyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2C=C3C=CC=CC3=NC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 LHLSXJIWISDKGG-UHFFFAOYSA-N 0.000 description 1
- SUXWTBAOYVYILW-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-(thiophen-2-ylmethyl)-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2SC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 SUXWTBAOYVYILW-UHFFFAOYSA-N 0.000 description 1
- YYXOXWVEQUZBAX-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n-pyrrolidin-3-yl-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(C2CNCC2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 YYXOXWVEQUZBAX-UHFFFAOYSA-N 0.000 description 1
- VKBJDOBPGVLLTB-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]naphthalen-1-amine Chemical compound C=1C=C(CNC=2C3=CC=CC=C3C=CC=2)C=CC=1CNCC1=CC=CC=N1 VKBJDOBPGVLLTB-UHFFFAOYSA-N 0.000 description 1
- DIRVCOZGHSWRJP-UHFFFAOYSA-N n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]quinolin-8-amine Chemical compound C=1C=C(CNC=2C3=NC=CC=C3C=CC=2)C=CC=1CNCC1=CC=CC=N1 DIRVCOZGHSWRJP-UHFFFAOYSA-N 0.000 description 1
- KNQYFARLRUKZKY-UHFFFAOYSA-N n-[[4-[[2-(4-methoxyphenyl)ethyl-(pyridin-2-ylmethyl)amino]methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C1=CC(OC)=CC=C1CCN(CC=1N=CC=CC=1)CC(C=C1)=CC=C1CNC1C2=NC=CC=C2CCC1 KNQYFARLRUKZKY-UHFFFAOYSA-N 0.000 description 1
- JZTNNWRILKGANO-UHFFFAOYSA-N n-[[4-[[2-methoxyethyl(pyridin-2-ylmethyl)amino]methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CNC2C3=NC=CC=C3CCC2)C=CC=1CN(CCOC)CC1=CC=CC=N1 JZTNNWRILKGANO-UHFFFAOYSA-N 0.000 description 1
- NJDVDIVVFUXOHL-UHFFFAOYSA-N n-benzyl-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(CC=2C=CC=CC=2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 NJDVDIVVFUXOHL-UHFFFAOYSA-N 0.000 description 1
- TUMGQCHXRWOHMH-UHFFFAOYSA-N n-phenyl-n'-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-n'-(5,6,7,8-tetrahydroquinolin-8-yl)ethane-1,2-diamine Chemical compound C=1C=CC=CC=1NCCN(C1C2=NC=CC=C2CCC1)CC(C=C1)=CC=C1CNCC1=CC=CC=N1 TUMGQCHXRWOHMH-UHFFFAOYSA-N 0.000 description 1
- JDUKCSJDLQKSCH-UHFFFAOYSA-N n-piperidin-4-yl-n-[[4-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]-5,6,7,8-tetrahydroquinolin-8-amine Chemical compound C=1C=C(CN(C2CCNCC2)C2C3=NC=CC=C3CCC2)C=CC=1CNCC1=CC=CC=N1 JDUKCSJDLQKSCH-UHFFFAOYSA-N 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- IXOXBSCIXZEQEQ-UHTZMRCNSA-N nelarabine Chemical compound C1=NC=2C(OC)=NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O IXOXBSCIXZEQEQ-UHTZMRCNSA-N 0.000 description 1
- 229960000801 nelarabine Drugs 0.000 description 1
- 229940071846 neulasta Drugs 0.000 description 1
- 229940029345 neupogen Drugs 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 229940100027 ontak Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- HZIVRQOIUMAXID-UHFFFAOYSA-N oxocane Chemical compound C1CCCOCCC1 HZIVRQOIUMAXID-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 108010044644 pegfilgrastim Proteins 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
- UEMDJZHLMSDWCP-UHFFFAOYSA-N phenyl-[4-[2-pyridin-2-ylethyl-[[3-[(pyridin-2-ylmethylamino)methyl]phenyl]methyl]amino]piperidin-1-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)N(CC1)CCC1N(CC=1C=C(CNCC=2N=CC=CC=2)C=CC=1)CCC1=CC=CC=N1 UEMDJZHLMSDWCP-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical group C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- PEZPMAYDXJQYRV-UHFFFAOYSA-N pixantrone Chemical compound O=C1C2=CN=CC=C2C(=O)C2=C1C(NCCN)=CC=C2NCCN PEZPMAYDXJQYRV-UHFFFAOYSA-N 0.000 description 1
- 229960004403 pixantrone Drugs 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 230000030786 positive chemotaxis Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 210000001586 pre-b-lymphocyte Anatomy 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical group N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229940120975 revlimid Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004641 rituximab Drugs 0.000 description 1
- 229960002530 sargramostim Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical class [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052815 sulfur oxide Inorganic materials 0.000 description 1
- 230000003319 supportive effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 229950010130 tamibarotene Drugs 0.000 description 1
- YNZUHDHIWWRGOR-UHFFFAOYSA-N tert-butyl 2-(chloromethyl)benzimidazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C(CCl)=NC2=C1 YNZUHDHIWWRGOR-UHFFFAOYSA-N 0.000 description 1
- DNTCKJDFHQADBP-UHFFFAOYSA-N tert-butyl 2-[(5,6,7,8-tetrahydroquinolin-8-ylamino)methyl]benzimidazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C(CNC3C4=NC=CC=C4CCC3)=NC2=C1 DNTCKJDFHQADBP-UHFFFAOYSA-N 0.000 description 1
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 229960005267 tositumomab Drugs 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 229940099039 velcade Drugs 0.000 description 1
- 208000020294 von Willebrand disease 1 Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/195—Chemokines, e.g. RANTES
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60136704P | 2004-08-13 | 2004-08-13 | |
| PCT/US2005/028783 WO2006020891A2 (en) | 2004-08-13 | 2005-08-11 | Chemokine combinations to mobilize progenitor/stem cells |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008509928A true JP2008509928A (ja) | 2008-04-03 |
| JP2008509928A5 JP2008509928A5 (OSRAM) | 2008-10-09 |
Family
ID=35908186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007525838A Withdrawn JP2008509928A (ja) | 2004-08-13 | 2005-08-11 | 前駆／幹細胞を動員するためのケモカインの組み合わせ |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060035829A1 (OSRAM) |
| EP (1) | EP1796716A4 (OSRAM) |
| JP (1) | JP2008509928A (OSRAM) |
| CN (1) | CN101094684A (OSRAM) |
| AU (1) | AU2005272653A1 (OSRAM) |
| BR (1) | BRPI0514343A (OSRAM) |
| CA (1) | CA2577046A1 (OSRAM) |
| TW (1) | TW200608991A (OSRAM) |
| WO (1) | WO2006020891A2 (OSRAM) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016516672A (ja) * | 2013-02-28 | 2016-06-09 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 幹細胞を動員するための方法および組成物 |
| JP2019507596A (ja) * | 2016-02-26 | 2019-03-22 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 生着性の高い造血幹細胞 |
| JP2021505172A (ja) * | 2017-12-06 | 2021-02-18 | マジェンタ セラピューティクス インコーポレイテッドＭａｇｅｎｔａ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | 造血幹細胞及び前駆細胞を動員させるための投薬レジメン |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8435939B2 (en) * | 2000-09-05 | 2013-05-07 | Biokine Therapeutics Ltd. | Polypeptide anti-HIV agent containing the same |
| JP2009504788A (ja) * | 2005-08-19 | 2009-02-05 | ジェンザイム・コーポレーション | 化学療法の強化方法 |
| AU2006340074A1 (en) * | 2006-02-24 | 2007-09-20 | Genzyme Corporation | Methods for increasing blood flow and/or promoting tissue regeneration |
| JP5257068B2 (ja) | 2006-05-16 | 2013-08-07 | 小野薬品工業株式会社 | 保護されていてもよい酸性基を含有する化合物およびその用途 |
| US20090325992A1 (en) | 2006-07-31 | 2009-12-31 | Ono Pharmaceutical Co., Ltd. | Compound having cyclic group bound thereto through spiro binding and use thereof |
| WO2008017025A2 (en) * | 2006-08-02 | 2008-02-07 | Genzyme Corporation | Combination therapy |
| EP2759302A3 (en) * | 2006-12-21 | 2014-11-05 | Biokine Therapeutics LTD. | 4F-benzoyl-TN14003 combined with rituximab for use in the treatment of a tumour |
| US9427456B2 (en) | 2009-06-14 | 2016-08-30 | Biokine Therapeutics Ltd. | Peptide therapy for increasing platelet levels |
| KR20200016407A (ko) | 2011-05-16 | 2020-02-14 | 젠자임 코포레이션 | Ｃｘｃｒ４ 길항제의 용도 |
| CN103159690B (zh) * | 2011-12-14 | 2015-03-25 | 朱靖华 | 对称大环胺化合物的结晶形式 |
| WO2013160895A1 (en) | 2012-04-24 | 2013-10-31 | Biokine Therapeutics Ltd. | Peptides and use thereof in the treatment of large cell lung cancer |
| CA2874850A1 (en) | 2012-06-07 | 2013-12-12 | Children's Hospital Los Angeles | Methods for treating neutropenia using retinoid agonists |
| CN106413701A (zh) | 2014-02-18 | 2017-02-15 | 洛杉矶儿童医院 | 用于治疗中性粒细胞减少症的组合物和方法 |
| AU2016269839B2 (en) * | 2015-06-03 | 2021-07-08 | The University Of Queensland | Mobilizing agents and uses therefor |
| AU2016291817A1 (en) | 2015-07-16 | 2018-02-22 | Biolinerx Ltd. | Compositions and methods for treating cancer |
| WO2017145161A1 (en) | 2016-02-23 | 2017-08-31 | Biolinerx Ltd. | Methods of treating acute myeloid leukemia |
| WO2018085574A2 (en) * | 2016-11-02 | 2018-05-11 | Washington University | Compositions comprising an integrin inhibitor and agents which interact with a chemokine and methods of use thereof |
| IL293956A (en) | 2017-04-12 | 2022-08-01 | Magenta Therapeutics Inc | Aryl hydrocarbon receptor antagonist and its uses |
| JP7412341B2 (ja) | 2017-10-31 | 2024-01-12 | エディジーン バイオテクノロジー インコーポレイテッド | 造血幹細胞および前駆細胞の増幅のための組成物および方法 |
| EP3703715A1 (en) | 2017-10-31 | 2020-09-09 | Magenta Therapeutics, Inc. | Compositions and methods for hematopoietic stem and progenitor cell transplant therapy |
| US10058573B1 (en) * | 2017-12-06 | 2018-08-28 | Magenta Therapeutics, Inc. | Dosing regimens for the mobilization of hematopoietic stem cells |
| US11260079B2 (en) | 2017-12-06 | 2022-03-01 | Magenta Therapeutics, Inc. | Dosing regimens for the mobilization of hematopoietic stem and progenitor cells |
| CN111902411A (zh) | 2018-01-03 | 2020-11-06 | 美真达治疗公司 | 用于扩增造血干细胞和祖细胞以及治疗遗传性代谢紊乱的组合物和方法 |
| US20220401481A1 (en) | 2019-11-01 | 2022-12-22 | Magenta Therapeutics, Inc. | Dosing regimens for the mobilization of hematopoietic stem and progenitor cells |
| WO2021222313A1 (en) | 2020-04-27 | 2021-11-04 | Magenta Therapeutics, Inc. | Methods and compositions for transducing hematopoietic stem and progenitor cells in vivo |
| EP4308694A1 (en) | 2021-03-16 | 2024-01-24 | Magenta Therapeutics, Inc. | Dosing regimens for hematopoietic stem cell mobilization for stem cell transplants in multiple myeloma patients |
| CN116789639A (zh) * | 2022-03-14 | 2023-09-22 | 上海医药工业研究院有限公司 | Mavorixafor的纯化方法、其盐及有关物质 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4680174A (en) * | 1984-05-24 | 1987-07-14 | Damon Biotech, Inc. | Induction of immune response by immunization with encapsulated antigen-producing cells |
| US4810643A (en) * | 1985-08-23 | 1989-03-07 | Kirin- Amgen Inc. | Production of pluripotent granulocyte colony-stimulating factor |
| US5194596A (en) * | 1989-07-27 | 1993-03-16 | California Biotechnology Inc. | Production of vascular endothelial cell growth factor |
| US5350836A (en) * | 1989-10-12 | 1994-09-27 | Ohio University | Growth hormone antagonists |
| US5021409A (en) * | 1989-12-21 | 1991-06-04 | Johnson Matthey Plc | Antiviral cyclic polyamines |
| US6001826A (en) * | 1989-12-21 | 1999-12-14 | Anormed, Inc. | Chemical compounds |
| GB9126677D0 (en) * | 1991-12-16 | 1992-02-12 | Johnson Matthey Plc | Improvements in chemical compounds |
| ES2210255T3 (es) * | 1993-06-08 | 2004-07-01 | Smithkline Beecham Corporation | Metodos para mejorar la actividad biologica de quimiocinas. |
| DE4320478B4 (de) * | 1993-06-21 | 2007-11-15 | Robert Bosch Gmbh | Fahrstabilitätsregler |
| JPH09506866A (ja) * | 1993-12-14 | 1997-07-08 | ジョーンズ ホプキンス ユニバーシティー スクール オブ メディシン | 医薬として活性のある物質の免疫療法のための放出制御 |
| GB9400411D0 (en) * | 1994-01-11 | 1994-03-09 | Johnson Matthey Plc | Improvements in chemical compounds |
| US6506770B1 (en) * | 1996-06-06 | 2003-01-14 | Anormed, Inc. | Antiviral compounds |
| GB9511357D0 (en) * | 1995-06-06 | 1995-08-02 | Johnson Matthey Plc | Improved antiviral compounds |
| US6713052B1 (en) * | 1995-10-24 | 2004-03-30 | Human Genome Sciences, Inc. | Method of mobilizing stem cells with chemokine β-8 |
| EP1016726A1 (en) * | 1998-12-30 | 2000-07-05 | Introgene B.V. | Gene therapy to promote angiogenesis |
| US6365583B1 (en) * | 1999-02-02 | 2002-04-02 | Anormed, Inc. | Methods to enhance white blood cell count |
| US6750348B1 (en) * | 1999-03-24 | 2004-06-15 | Anormed, Inc. | Chemokine receptor binding heterocyclic compounds |
| EP1244648B1 (en) * | 1999-12-17 | 2009-04-15 | Genzyme Corporation | Chemokine receptor binding heterocyclic compounds |
| DE60143457D1 (de) * | 2000-09-15 | 2010-12-23 | Anormed Inc | Chemokin Rezeptor bindende heterozyklische Verbindungen |
| NZ524421A (en) * | 2000-09-15 | 2005-02-25 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| IL154227A0 (en) * | 2000-09-15 | 2003-07-31 | Anormed Inc | Chemokine receptor binding heterocyclic compounds |
| PL359292A1 (en) * | 2000-09-29 | 2004-08-23 | Anormed Inc. | Process for preparation of n-1 protected n ring nitrogen containing cyclic polyamines and products thereof |
| WO2002081727A2 (en) * | 2001-04-03 | 2002-10-17 | Pe Corporation (Ny) | Isolated human kinase proteins, nucleic acid molecules encoding human kinase proteins, and uses thereof |
| ATE538785T1 (de) * | 2001-07-31 | 2012-01-15 | Genzyme Global S A R L | Verfahren zur mobilisierung von vorläufer/stammzellen |
| US7169750B2 (en) * | 2001-07-31 | 2007-01-30 | Anormed, Inc. | Methods to mobilize progenitor/stem cells |
| CA2469477A1 (en) * | 2001-12-07 | 2003-06-12 | Toolgen, Inc. | Phenotypic screen of chimeric proteins |
| US7291631B2 (en) * | 2003-04-11 | 2007-11-06 | Genzyme Corporation | CXCR4 chemokine receptor binding compounds |
| CA2517077C (en) * | 2003-04-22 | 2013-03-12 | Anormed Inc. | Chemokine receptor binding heterocyclic compounds with enhanced efficacy |
| CA2548393A1 (en) * | 2003-12-11 | 2005-06-30 | Anormed Inc. | Chemokine receptor binding compounds |
-
2005
- 2005-08-11 BR BRPI0514343-8A patent/BRPI0514343A/pt not_active IP Right Cessation
- 2005-08-11 WO PCT/US2005/028783 patent/WO2006020891A2/en not_active Ceased
- 2005-08-11 CA CA002577046A patent/CA2577046A1/en not_active Abandoned
- 2005-08-11 CN CNA2005800323327A patent/CN101094684A/zh active Pending
- 2005-08-11 JP JP2007525838A patent/JP2008509928A/ja not_active Withdrawn
- 2005-08-11 US US11/202,482 patent/US20060035829A1/en not_active Abandoned
- 2005-08-11 AU AU2005272653A patent/AU2005272653A1/en not_active Abandoned
- 2005-08-11 EP EP05788603A patent/EP1796716A4/en not_active Withdrawn
- 2005-08-12 TW TW094127548A patent/TW200608991A/zh unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016516672A (ja) * | 2013-02-28 | 2016-06-09 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 幹細胞を動員するための方法および組成物 |
| JP2020073589A (ja) * | 2013-02-28 | 2020-05-14 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 幹細胞を動員するための方法および組成物 |
| JP2021165306A (ja) * | 2013-02-28 | 2021-10-14 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 幹細胞を動員するための方法および組成物 |
| KR20210132751A (ko) * | 2013-02-28 | 2021-11-04 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 줄기세포를 동원하기 위한 방법 및 조성물 |
| KR102503695B1 (ko) * | 2013-02-28 | 2023-02-23 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 줄기세포를 동원하기 위한 방법 및 조성물 |
| JP2019507596A (ja) * | 2016-02-26 | 2019-03-22 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 生着性の高い造血幹細胞 |
| JP2021175409A (ja) * | 2016-02-26 | 2021-11-04 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 生着性の高い造血幹細胞 |
| JP2021505172A (ja) * | 2017-12-06 | 2021-02-18 | マジェンタ セラピューティクス インコーポレイテッドＭａｇｅｎｔａ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | 造血幹細胞及び前駆細胞を動員させるための投薬レジメン |
| JP2024023226A (ja) * | 2017-12-06 | 2024-02-21 | マジェンタ セラピューティクス インコーポレイテッド | 造血幹細胞及び前駆細胞を動員させるための投薬レジメン |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006020891A3 (en) | 2006-07-13 |
| EP1796716A4 (en) | 2010-09-08 |
| CA2577046A1 (en) | 2006-02-23 |
| TW200608991A (en) | 2006-03-16 |
| AU2005272653A1 (en) | 2006-02-23 |
| US20060035829A1 (en) | 2006-02-16 |
| BRPI0514343A (pt) | 2008-06-10 |
| EP1796716A2 (en) | 2007-06-20 |
| CN101094684A (zh) | 2007-12-26 |
| WO2006020891A2 (en) | 2006-02-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008509928A (ja) | 前駆／幹細胞を動員するためのケモカインの組み合わせ | |
| KR100996378B1 (ko) | 선조/줄기 세포를 이동시킴으로써 이식에 사용하기 위한 약제학적 조성물 | |
| US20100003224A1 (en) | Combination Therapy | |
| US20100178271A1 (en) | Combination Therapy | |
| AU2002318927A1 (en) | Methods to mobilize progenitor/stem cells | |
| MX2007001802A (en) | Chemokine combinations to mobilize progenitor/stem cells | |
| HK40026817A (en) | Methods to mobilize progenitor/stem cells |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080811 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080821 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20081120 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20081120 |
|
| A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20100805 |