JP2020023529A5

JP2020023529A5 -

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Publication number: JP2020023529A5
Authority: JP; Japan
Prior art keywords: amino; phenylcyclopropyl; piperidin; azetidin; acetonitrile
Prior art date: 2019-10-09
Legal status : Granted

Application number

JP2019186168A

Other languages

English (en)

Japanese (ja)

Other versions

JP2020023529A6 (ja

JP2020023529A (ja

JP6781815B2 (ja

Filing date

2019-10-09

Publication date

2020-05-21

2019-10-09 Application filed filed Critical

2020-02-13 Publication of JP2020023529A publication Critical patent/JP2020023529A/ja

2020-04-16 Publication of JP2020023529A6 publication Critical patent/JP2020023529A6/ja

2020-05-21 Publication of JP2020023529A5 publication Critical patent/JP2020023529A5/ja

2020-11-04 Application granted granted Critical

2020-11-04 Publication of JP6781815B2 publication Critical patent/JP6781815B2/ja

Status Active legal-status Critical Current

2035-02-12 Anticipated expiration legal-status Critical

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239000003814 drug Substances 0.000 claims 51
125000000217 alkyl group Chemical group 0.000 claims 38
-1 4-fluorophenylmethyl Chemical group 0.000 claims 32
201000011510 cancer Diseases 0.000 claims 21
150000001875 compounds Chemical class 0.000 claims 20
206010028980 Neoplasm Diseases 0.000 claims 19
150000003839 salts Chemical class 0.000 claims 18
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 12
125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
125000003118 aryl group Chemical group 0.000 claims 9
208000009956 adenocarcinoma Diseases 0.000 claims 8
201000010099 disease Diseases 0.000 claims 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
229940079593 drug Drugs 0.000 claims 8
125000005843 halogen group Chemical group 0.000 claims 8
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 6
229960004641 rituximab Drugs 0.000 claims 6
206010025323 Lymphomas Diseases 0.000 claims 5
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 5
229960005420 etoposide Drugs 0.000 claims 5
206010016629 fibroma Diseases 0.000 claims 5
206010041823 squamous cell carcinoma Diseases 0.000 claims 5
125000001424 substituent group Chemical group 0.000 claims 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
206010024612 Lipoma Diseases 0.000 claims 4
208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 4
125000004966 cyanoalkyl group Chemical group 0.000 claims 4
201000011066 hemangioma Diseases 0.000 claims 4
229940124597 therapeutic agent Drugs 0.000 claims 4
230000003612 virological effect Effects 0.000 claims 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
208000031261 Acute myeloid leukaemia Diseases 0.000 claims 3
208000006168 Ewing Sarcoma Diseases 0.000 claims 3
201000008808 Fibrosarcoma Diseases 0.000 claims 3
201000003793 Myelodysplastic syndrome Diseases 0.000 claims 3
208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 3
229910019142 PO4 Inorganic materials 0.000 claims 3
206010043276 Teratoma Diseases 0.000 claims 3
125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 3
125000002393 azetidinyl group Chemical group 0.000 claims 3
210000004027 cell Anatomy 0.000 claims 3
206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 3
206010027191 meningioma Diseases 0.000 claims 3
206010028537 myelofibrosis Diseases 0.000 claims 3
201000008968 osteosarcoma Diseases 0.000 claims 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
239000010452 phosphate Substances 0.000 claims 3
125000003386 piperidinyl group Chemical group 0.000 claims 3
208000003476 primary myelofibrosis Diseases 0.000 claims 3
CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 claims 2
BBEZPWPHOQIEGI-FOIFJWKZSA-N 2-[1-(1-methylpyrazole-4-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Cn1cc(cn1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 BBEZPWPHOQIEGI-FOIFJWKZSA-N 0.000 claims 2
LRISLSZFPGTNFP-CFYLOBDVSA-N 2-[1-(4-hydroxycyclohexanecarbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CCC(CC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 LRISLSZFPGTNFP-CFYLOBDVSA-N 0.000 claims 2
LNKLCUWGJGYEJN-YRTVTSRJSA-N 2-[1-(4-hydroxycyclohexyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CCC(CC1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 LNKLCUWGJGYEJN-YRTVTSRJSA-N 0.000 claims 2
WKZYPDVFDYESLQ-RBUKOAKNSA-N 2-[1-methylsulfonyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CS(=O)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N WKZYPDVFDYESLQ-RBUKOAKNSA-N 0.000 claims 2
GLXPUBZSNUMXBZ-ZWKOTPCHSA-N 3-(cyanomethyl)-3-[4-[[(1R,2S)-2-(4-fluorophenyl)cyclopropyl]amino]piperidin-1-yl]azetidine-1-sulfonamide Chemical compound C(#N)CC1(CN(C1)S(=O)(=O)N)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=C(C=C1)F GLXPUBZSNUMXBZ-ZWKOTPCHSA-N 0.000 claims 2
GMBKWWMGXRBRKT-ZWKOTPCHSA-N 3-(cyanomethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-sulfonamide Chemical compound C(#N)CC1(CN(C1)S(=O)(=O)N)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 GMBKWWMGXRBRKT-ZWKOTPCHSA-N 0.000 claims 2
208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 2
201000003076 Angiosarcoma Diseases 0.000 claims 2
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 2
206010007275 Carcinoid tumour Diseases 0.000 claims 2
206010008342 Cervix carcinoma Diseases 0.000 claims 2
208000005243 Chondrosarcoma Diseases 0.000 claims 2
206010009944 Colon cancer Diseases 0.000 claims 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 2
208000032027 Essential Thrombocythemia Diseases 0.000 claims 2
208000032612 Glial tumor Diseases 0.000 claims 2
206010018338 Glioma Diseases 0.000 claims 2
208000002927 Hamartoma Diseases 0.000 claims 2
208000001258 Hemangiosarcoma Diseases 0.000 claims 2
241000701085 Human alphaherpesvirus 3 Species 0.000 claims 2
208000007766 Kaposi sarcoma Diseases 0.000 claims 2
208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 2
208000018142 Leiomyosarcoma Diseases 0.000 claims 2
208000034578 Multiple myelomas Diseases 0.000 claims 2
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims 2
201000004404 Neurofibroma Diseases 0.000 claims 2
206010033128 Ovarian cancer Diseases 0.000 claims 2
206010061535 Ovarian neoplasm Diseases 0.000 claims 2
206010035226 Plasma cell myeloma Diseases 0.000 claims 2
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
208000033826 Promyelocytic Acute Leukemia Diseases 0.000 claims 2
206010060862 Prostate cancer Diseases 0.000 claims 2
208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
241000700584 Simplexvirus Species 0.000 claims 2
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 2
208000008383 Wilms tumor Diseases 0.000 claims 2
208000017733 acquired polycythemia vera Diseases 0.000 claims 2
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims 2
STIUWSWFXIBBKI-UHFFFAOYSA-N azetidine-1-sulfonamide Chemical compound NS(=O)(=O)N1CCC1 STIUWSWFXIBBKI-UHFFFAOYSA-N 0.000 claims 2
229960001467 bortezomib Drugs 0.000 claims 2
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 claims 2
229960002092 busulfan Drugs 0.000 claims 2
208000002458 carcinoid tumor Diseases 0.000 claims 2
201000010881 cervical cancer Diseases 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 claims 2
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
125000001188 haloalkyl group Chemical group 0.000 claims 2
206010073071 hepatocellular carcinoma Diseases 0.000 claims 2
231100000844 hepatocellular carcinoma Toxicity 0.000 claims 2
239000003112 inhibitor Substances 0.000 claims 2
201000010260 leiomyoma Diseases 0.000 claims 2
201000001441 melanoma Diseases 0.000 claims 2
201000008026 nephroblastoma Diseases 0.000 claims 2
208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
229960005184 panobinostat Drugs 0.000 claims 2
FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 claims 2
208000037244 polycythemia vera Diseases 0.000 claims 2
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JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 2
208000000649 small cell carcinoma Diseases 0.000 claims 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 claims 2
229960000237 vorinostat Drugs 0.000 claims 2
BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 claims 1
XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims 1
MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 claims 1
FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 claims 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 1
XGQXULJHBWKUJY-LYIKAWCPSA-N (z)-but-2-enedioic acid;n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide Chemical compound OC(=O)\C=C/C(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C XGQXULJHBWKUJY-LYIKAWCPSA-N 0.000 claims 1
HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 claims 1
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
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 claims 1
TVDKZBASXPLLBZ-FOIFJWKZSA-N 2-[1-(1-hydroxycyclopentanecarbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1(CCCC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 TVDKZBASXPLLBZ-FOIFJWKZSA-N 0.000 claims 1
WNSIQTHQNNHKOU-GFOWMXPYSA-N 2-[1-(1-hydroxycyclopropanecarbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1(CC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 WNSIQTHQNNHKOU-GFOWMXPYSA-N 0.000 claims 1
YSIRGVBHKRVSKU-FOIFJWKZSA-N 2-[1-(1-methylpyrazol-4-yl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Cn1cc(cn1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 YSIRGVBHKRVSKU-FOIFJWKZSA-N 0.000 claims 1
FTXZQOUPDXBLHA-FOIFJWKZSA-N 2-[1-(1-methylpyrazol-4-yl)sulfonyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Cn1cc(cn1)S(=O)(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 FTXZQOUPDXBLHA-FOIFJWKZSA-N 0.000 claims 1
XEDHJJBMYHJZND-UHFFFAOYSA-N 2-[1-(2-fluorobenzoyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Fc1ccccc1C(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 XEDHJJBMYHJZND-UHFFFAOYSA-N 0.000 claims 1
YGKRJKSCOHXOOF-GFOWMXPYSA-N 2-[1-(2-hydroxyethyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OCCN1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 YGKRJKSCOHXOOF-GFOWMXPYSA-N 0.000 claims 1
NQZHVXXBZTZCFM-BPGUCPLFSA-N 2-[1-(2-methylpyrazole-3-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Cn1nccc1C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 NQZHVXXBZTZCFM-BPGUCPLFSA-N 0.000 claims 1
MJPVZDXQCTUQIG-UHFFFAOYSA-N 2-[1-(3,5-difluorobenzoyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Fc1cc(F)cc(c1)C(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 MJPVZDXQCTUQIG-UHFFFAOYSA-N 0.000 claims 1
JHBCJWXVGNIDCD-UHFFFAOYSA-N 2-[1-(3-fluorobenzoyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Fc1cccc(c1)C(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 JHBCJWXVGNIDCD-UHFFFAOYSA-N 0.000 claims 1
ZPVKWJUILDIPIU-BPGUCPLFSA-N 2-[1-(3-hydroxyazetidine-1-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CN(C1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 ZPVKWJUILDIPIU-BPGUCPLFSA-N 0.000 claims 1
PPOYSOLYFOBOFP-YMOXTTMHSA-N 2-[1-(3-hydroxycyclobutyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CC(C1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PPOYSOLYFOBOFP-YMOXTTMHSA-N 0.000 claims 1
QEODSRKCBHJXGW-UHFFFAOYSA-N 2-[1-(4-fluorobenzoyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Fc1ccc(cc1)C(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 QEODSRKCBHJXGW-UHFFFAOYSA-N 0.000 claims 1
BSGNTEOUVKIDEX-UHFFFAOYSA-N 2-[1-(4-fluorobenzoyl)-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound Fc1ccc(cc1)C(=O)N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1 BSGNTEOUVKIDEX-UHFFFAOYSA-N 0.000 claims 1
CFEZGDDEXODSOP-OZAIVSQSSA-N 2-[1-(4-hydroxypiperidine-1-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CCN(CC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 CFEZGDDEXODSOP-OZAIVSQSSA-N 0.000 claims 1
JDOVUIRQPWAANN-XMMISQBUSA-N 2-[1-(4-methoxypiperidine-1-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound COC1CCN(CC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 JDOVUIRQPWAANN-XMMISQBUSA-N 0.000 claims 1
MOKIPZSEHIRCHU-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound O=S(=O)(N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1)c1ccccc1 MOKIPZSEHIRCHU-UHFFFAOYSA-N 0.000 claims 1
KQQSUVAYFVDCOX-XZOQPEGZSA-N 2-[1-(cyclopropylmethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]-N,N-dimethylacetamide Chemical compound C1(CC1)CN1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC(=O)N(C)C KQQSUVAYFVDCOX-XZOQPEGZSA-N 0.000 claims 1
POXDXBWDCJXXQK-FCHUYYIVSA-N 2-[1-(cyclopropylmethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]-N-methylacetamide Chemical compound C1(CC1)CN1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC(=O)NC POXDXBWDCJXXQK-FCHUYYIVSA-N 0.000 claims 1
GOBGZDUAYFOHAB-FOIFJWKZSA-N 2-[1-(morpholine-4-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)N1CCOCC1 GOBGZDUAYFOHAB-FOIFJWKZSA-N 0.000 claims 1
SRPFBOAHKKBKKR-OZAIVSQSSA-N 2-[1-(oxan-4-yl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound N#CCC1(CN(C1)C1CCOCC1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 SRPFBOAHKKBKKR-OZAIVSQSSA-N 0.000 claims 1
FXFHNEHARADBNL-JTGIGXABSA-N 2-[1-(oxolan-3-yl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1(=CC=CC=C1)[C@H]1[C@@H](C1)NC1CCN(CC1)C1(CN(C1)C1COCC1)CC#N FXFHNEHARADBNL-JTGIGXABSA-N 0.000 claims 1
BMNSVVYABBFIOM-ATKRNPRHSA-N 2-[1-(oxolane-2-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C(C1CCCO1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 BMNSVVYABBFIOM-ATKRNPRHSA-N 0.000 claims 1
PNLVAMICRIAANP-KITAHSCOSA-N 2-[1-(oxolane-3-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C(C1CCOC1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PNLVAMICRIAANP-KITAHSCOSA-N 0.000 claims 1
BMNSVVYABBFIOM-HRUVVLKGSA-N 2-[1-[(2R)-oxolane-2-carbonyl]-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C([C@H]1CCCO1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 BMNSVVYABBFIOM-HRUVVLKGSA-N 0.000 claims 1
BMNSVVYABBFIOM-PDQYLBCOSA-N 2-[1-[(2S)-oxolane-2-carbonyl]-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C([C@@H]1CCCO1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 BMNSVVYABBFIOM-PDQYLBCOSA-N 0.000 claims 1
PNLVAMICRIAANP-PSQUCKQXSA-N 2-[1-[(3R)-oxolane-3-carbonyl]-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C([C@@H]1CCOC1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PNLVAMICRIAANP-PSQUCKQXSA-N 0.000 claims 1
PNLVAMICRIAANP-KFEBLCFASA-N 2-[1-[(3S)-oxolane-3-carbonyl]-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C([C@H]1CCOC1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PNLVAMICRIAANP-KFEBLCFASA-N 0.000 claims 1
NYIWGYPPKJPGTJ-GFOWMXPYSA-N 2-[1-[4-(methoxymethyl)-4-[[[(1R)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetic acid Chemical compound COCC1(CN[C@@H]2CC2c2ccccc2)CCN(CC1)C1(CC(O)=O)CCC1 NYIWGYPPKJPGTJ-GFOWMXPYSA-N 0.000 claims 1
GHEGXJMODHODMQ-UHFFFAOYSA-N 2-[1-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]cyclobutyl]acetonitrile Chemical compound N#CCC1(CCC1)N1CCC(CC1)NC1CC1c1ccccc1 GHEGXJMODHODMQ-UHFFFAOYSA-N 0.000 claims 1
INRMDSMOHQTQSG-WUBHUQEYSA-N 2-[1-[4-[(4-fluorophenyl)methyl]-4-[[[(1R)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetic acid Chemical compound OC(=O)CC1(CCC1)N1CCC(CN[C@@H]2CC2c2ccccc2)(Cc2ccc(F)cc2)CC1 INRMDSMOHQTQSG-WUBHUQEYSA-N 0.000 claims 1
RRYIYTAJBSSOPL-UHFFFAOYSA-N 2-[1-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]cyclobutyl]acetonitrile Chemical compound N#CCC1(CCC1)N1CCC(CNC2CC2c2ccccc2)CC1 RRYIYTAJBSSOPL-UHFFFAOYSA-N 0.000 claims 1
ATMPNNXKBAQDJV-MUMRKEEXSA-N 2-[1-[4-[[[(1R)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetic acid Chemical compound OC(=O)CC1(CCC1)N1CCC(CN[C@@H]2CC2c2ccccc2)CC1 ATMPNNXKBAQDJV-MUMRKEEXSA-N 0.000 claims 1
ZQLIYVSBBTXGFL-RBUKOAKNSA-N 2-[1-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetic acid Chemical compound CC1(CCN(CC1)C1(CCC1)CC(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 ZQLIYVSBBTXGFL-RBUKOAKNSA-N 0.000 claims 1
CHLWPXFUYDMJHJ-VQTJNVASSA-N 2-[1-acetyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C(C)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N CHLWPXFUYDMJHJ-VQTJNVASSA-N 0.000 claims 1
JIGFNRMEKAMQDW-LEWJYISDSA-N 2-[1-acetyl-4-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound C(C)(=O)N1CCC(CC1)(N1CC(C1)CN[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N JIGFNRMEKAMQDW-LEWJYISDSA-N 0.000 claims 1
QXXWMQDZVMZJOV-BJKOFHAPSA-N 2-[1-benzoyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C(C1=CC=CC=C1)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N QXXWMQDZVMZJOV-BJKOFHAPSA-N 0.000 claims 1
DYHJMPPSZFIVIQ-UHFFFAOYSA-N 2-[1-benzoyl-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1)c1ccccc1 DYHJMPPSZFIVIQ-UHFFFAOYSA-N 0.000 claims 1
YIVORPSROJSZLH-LOSJGSFVSA-N 2-[1-benzyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C(C1=CC=CC=C1)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N YIVORPSROJSZLH-LOSJGSFVSA-N 0.000 claims 1
CBQUUHSDOMDECC-MUMRKEEXSA-N 2-[1-ethyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetic acid Chemical compound CCN1CC(CC(O)=O)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 CBQUUHSDOMDECC-MUMRKEEXSA-N 0.000 claims 1
UOUIRRWHFRPORZ-GFOWMXPYSA-N 2-[1-ethylsulfonyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CCS(=O)(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 UOUIRRWHFRPORZ-GFOWMXPYSA-N 0.000 claims 1
NKPUMNAEPKDNKZ-GFOWMXPYSA-N 2-[1-ethylsulfonyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]ethanol Chemical compound CCS(=O)(=O)N1CC(CCO)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 NKPUMNAEPKDNKZ-GFOWMXPYSA-N 0.000 claims 1
OSXJNKWWLVSYHK-LEWJYISDSA-N 2-[1-ethylsulfonyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]-N,N-dimethylacetamide Chemical compound C(C)S(=O)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC(=O)N(C)C OSXJNKWWLVSYHK-LEWJYISDSA-N 0.000 claims 1
JGILOSZKUGHPOT-UHFFFAOYSA-N 2-[1-ethylsulfonyl-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CCS(=O)(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 JGILOSZKUGHPOT-UHFFFAOYSA-N 0.000 claims 1
XZDHATBCLTUCFX-UHFFFAOYSA-N 2-[1-methyl-3-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1CC(CC#N)(C1)N1CCC(CC1)NC1CC1c1ccccc1 XZDHATBCLTUCFX-UHFFFAOYSA-N 0.000 claims 1
UUFGEUMETGJRQR-QRWMCTBCSA-N 2-[1-methyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetic acid Chemical compound CN1CC(CC(O)=O)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 UUFGEUMETGJRQR-QRWMCTBCSA-N 0.000 claims 1
XZDHATBCLTUCFX-MUMRKEEXSA-N 2-[1-methyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 XZDHATBCLTUCFX-MUMRKEEXSA-N 0.000 claims 1
LHGCYQPQMMRWBE-UHFFFAOYSA-N 2-[1-methyl-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 LHGCYQPQMMRWBE-UHFFFAOYSA-N 0.000 claims 1
FDRSPKPJWQDXPR-VQTJNVASSA-N 2-[1-methyl-4-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound CN1CCC(CC1)(N1CC(C1)CN[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N FDRSPKPJWQDXPR-VQTJNVASSA-N 0.000 claims 1
NBGAAOKBUAFGJO-RBUKOAKNSA-N 2-[1-methylsulfonyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]ethanol Chemical compound CS(=O)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CCO NBGAAOKBUAFGJO-RBUKOAKNSA-N 0.000 claims 1
NCGLLDRHTVMYPJ-UHFFFAOYSA-N 2-[1-methylsulfonyl-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound CS(=O)(=O)N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1 NCGLLDRHTVMYPJ-UHFFFAOYSA-N 0.000 claims 1
WAOKAHCYIMPPGD-UHFFFAOYSA-N 2-[3-(cyanomethyl)-3-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]azetidin-1-yl]benzonitrile Chemical compound N#CCC1(CN(C1)c1ccccc1C#N)N1CCC(CC1)NC1CC1c1ccccc1 WAOKAHCYIMPPGD-UHFFFAOYSA-N 0.000 claims 1
JDCIQSZZZCQWTA-UHFFFAOYSA-N 2-[3-(cyanomethyl)-3-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]azetidin-1-yl]pyridine-3-carbonitrile Chemical compound N#CCC1(CN(C1)c1ncccc1C#N)N1CCC(CC1)NC1CC1c1ccccc1 JDCIQSZZZCQWTA-UHFFFAOYSA-N 0.000 claims 1
KLWGXIYQXBIWJD-VQTJNVASSA-N 2-[3-(cyanomethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-1-yl]-N-methylacetamide Chemical compound C(#N)CC1(CN(C1)CC(=O)NC)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 KLWGXIYQXBIWJD-VQTJNVASSA-N 0.000 claims 1
JXCHKGWNLZVMEZ-RBUKOAKNSA-N 2-[3-(cyanomethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-1-yl]acetamide Chemical compound C(#N)CC1(CN(C1)CC(=O)N)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 JXCHKGWNLZVMEZ-RBUKOAKNSA-N 0.000 claims 1
PWIOSBYHMSARTI-UHFFFAOYSA-N 2-[3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-1-yl]benzonitrile Chemical compound N#CCC1(CN(C1)c1ccccc1C#N)N1CCC(CNC2CC2c2ccccc2)CC1 PWIOSBYHMSARTI-UHFFFAOYSA-N 0.000 claims 1
CTZRQHBOAPYTEO-UHFFFAOYSA-N 2-[3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-1-yl]pyridine-3-carbonitrile Chemical compound N#CCC1(CN(C1)c1ncccc1C#N)N1CCC(CNC2CC2c2ccccc2)CC1 CTZRQHBOAPYTEO-UHFFFAOYSA-N 0.000 claims 1
UXIYDZIOOUEJGJ-DLBZAZTESA-N 2-[3-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1(=CC=CC=C1)[C@H]1[C@@H](C1)NCC1CN(C1)C1(CNC1)CC#N UXIYDZIOOUEJGJ-DLBZAZTESA-N 0.000 claims 1
BWGRVHGXZYCISM-MUMRKEEXSA-N 2-[3-[4-[[(1R)-2-(4-fluorophenyl)cyclopropyl]amino]piperidin-1-yl]-1-methylsulfonylazetidin-3-yl]acetonitrile Chemical compound CS(=O)(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccc(F)cc1 BWGRVHGXZYCISM-MUMRKEEXSA-N 0.000 claims 1
IIDCSONIAIQNMY-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,2-thiazole-5-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1ccns1 IIDCSONIAIQNMY-GFOWMXPYSA-N 0.000 claims 1
USUWNBOZHLVEAO-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazol-2-ylmethyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(Cc2nccs2)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 USUWNBOZHLVEAO-GFOWMXPYSA-N 0.000 claims 1
GHWJMOSGGHRPOZ-BPGUCPLFSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazol-5-ylmethyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(Cc2cncs2)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 GHWJMOSGGHRPOZ-BPGUCPLFSA-N 0.000 claims 1
DEVUVKQKULAJNV-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazole-2-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1nccs1 DEVUVKQKULAJNV-GFOWMXPYSA-N 0.000 claims 1
UMLNPHYCWGBJOH-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazole-4-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1cscn1 UMLNPHYCWGBJOH-GFOWMXPYSA-N 0.000 claims 1
XGFPOLXECPYKPJ-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazole-5-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1cncs1 XGFPOLXECPYKPJ-GFOWMXPYSA-N 0.000 claims 1
TYHVLCMAEMDYCP-BPGUCPLFSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1H-pyrazole-4-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1cn[nH]c1 TYHVLCMAEMDYCP-BPGUCPLFSA-N 0.000 claims 1
DAGXBMVVNPMYCV-VGAJERRHSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1H-pyrazole-5-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1ccn[nH]1 DAGXBMVVNPMYCV-VGAJERRHSA-N 0.000 claims 1
FMBNWGHWIFUXPF-XMMISQBUSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(2-pyridin-2-ylacetyl)azetidin-3-yl]acetonitrile Chemical compound O=C(Cc1ccccn1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 FMBNWGHWIFUXPF-XMMISQBUSA-N 0.000 claims 1
WQPGXBJNMQFZEF-MUMRKEEXSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(3,3,3-trifluoropropyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(CCC(F)(F)F)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 WQPGXBJNMQFZEF-MUMRKEEXSA-N 0.000 claims 1
HGTYIFDNJSWEGV-BPGUCPLFSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(pyrazine-2-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1cnccn1 HGTYIFDNJSWEGV-BPGUCPLFSA-N 0.000 claims 1
PAODTXXDMLQHCY-BPGUCPLFSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(pyrimidin-2-ylmethyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(Cc2ncccn2)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PAODTXXDMLQHCY-BPGUCPLFSA-N 0.000 claims 1
NLKWZDUQUSVPJL-FOIFJWKZSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(pyrimidin-5-ylmethyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(Cc2cncnc2)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 NLKWZDUQUSVPJL-FOIFJWKZSA-N 0.000 claims 1
XVOKNSJVLHJVLS-QRWMCTBCSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound N#CCC1(CNC1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 XVOKNSJVLHJVLS-QRWMCTBCSA-N 0.000 claims 1
MEHVWKKCGUIXNI-STTLMXHVSA-N 2-[3-[4-[[(1R,2S)-2-(4-fluorophenyl)cyclopropyl]amino]piperidin-1-yl]-1-(4-hydroxycyclohexyl)azetidin-3-yl]acetonitrile Chemical compound FC1=CC=C(C=C1)[C@H]1[C@@H](C1)NC1CCN(CC1)C1(CN(C1)C1CCC(CC1)O)CC#N MEHVWKKCGUIXNI-STTLMXHVSA-N 0.000 claims 1
XVOKNSJVLHJVLS-ZWKOTPCHSA-N 2-[3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1(=CC=CC=C1)[C@H]1[C@@H](C1)NC1CCN(CC1)C1(CNC1)CC#N XVOKNSJVLHJVLS-ZWKOTPCHSA-N 0.000 claims 1
XVOKNSJVLHJVLS-MSOLQXFVSA-N 2-[3-[4-[[(1S,2R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1(=CC=CC=C1)[C@@H]1[C@H](C1)NC1CCN(CC1)C1(CNC1)CC#N XVOKNSJVLHJVLS-MSOLQXFVSA-N 0.000 claims 1
TUXVOJPDNKEUES-UHFFFAOYSA-N 2-[3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]-1-[3-(trifluoromethyl)pyridin-2-yl]azetidin-3-yl]acetonitrile Chemical compound FC(F)(F)c1cccnc1N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 TUXVOJPDNKEUES-UHFFFAOYSA-N 0.000 claims 1
ITMDMKOHSAXUAX-UHFFFAOYSA-N 2-[3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]azetidin-3-yl]acetonitrile Chemical compound FC(F)(F)c1ccc(nc1)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 ITMDMKOHSAXUAX-UHFFFAOYSA-N 0.000 claims 1
DOMHYKFZPPFFSW-UHFFFAOYSA-N 2-[3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CNC1)N1CCC(CNC2CC2c2ccccc2)CC1 DOMHYKFZPPFFSW-UHFFFAOYSA-N 0.000 claims 1
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201000005102 vulva cancer Diseases 0.000 claims 1
XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 claims 1
229960004276 zoledronic acid Drugs 0.000 claims 1
150000003952 β-lactams Chemical class 0.000 claims 1

JP2019186168A 2014-02-13 2019-10-09 Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 Active JP6781815B2 (ja)