JP2014501717A5 - - Google Patents
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- Publication number
- JP2014501717A5 JP2014501717A5 JP2013538883A JP2013538883A JP2014501717A5 JP 2014501717 A5 JP2014501717 A5 JP 2014501717A5 JP 2013538883 A JP2013538883 A JP 2013538883A JP 2013538883 A JP2013538883 A JP 2013538883A JP 2014501717 A5 JP2014501717 A5 JP 2014501717A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- triazol
- propan
- optionally substituted
- compound
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 239000003098 androgen Substances 0.000 claims 4
- 210000003169 central nervous system Anatomy 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 2
- DFHXGPAXOUDLRU-UHFFFAOYSA-N 1-(5,6-dichloroquinolin-2-yl)-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C(Cl)=C(Cl)C=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 DFHXGPAXOUDLRU-UHFFFAOYSA-N 0.000 claims 2
- MSVVIRWQIISUNJ-UHFFFAOYSA-N 1-(6,7-dichloroquinolin-2-yl)-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C=C(Cl)C(Cl)=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 MSVVIRWQIISUNJ-UHFFFAOYSA-N 0.000 claims 2
- MMVFJKFSRQHOKE-UHFFFAOYSA-N 1-(6,7-difluoroquinolin-2-yl)-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C=C(F)C(F)=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 MMVFJKFSRQHOKE-UHFFFAOYSA-N 0.000 claims 2
- FNQBQSDVRFAVIN-UHFFFAOYSA-N 1-(6,7-dimethoxyisoquinolin-3-yl)-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C1=C2C=C(OC)C(OC)=CC2=CN=C1C(O)(C(C)C)C1=CNN=N1 FNQBQSDVRFAVIN-UHFFFAOYSA-N 0.000 claims 2
- ZBZKIRAMMFHRIY-UHFFFAOYSA-N 1-(6,7-dimethoxynaphthalen-2-yl)-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C1=C2C=C(OC)C(OC)=CC2=CC=C1C(O)(C(C)C)C1=CNN=N1 ZBZKIRAMMFHRIY-UHFFFAOYSA-N 0.000 claims 2
- JLICWFKFYANSGY-UHFFFAOYSA-N 1-(6-cyclopropyloxyquinolin-2-yl)-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C=C(OC3CC3)C=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 JLICWFKFYANSGY-UHFFFAOYSA-N 0.000 claims 2
- IXJBYAKVAODCDH-UHFFFAOYSA-N 1-(6-methoxyquinolin-2-yl)-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C1=CC2=CC(OC)=CC=C2N=C1C(O)(C(C)C)C1=CNN=N1 IXJBYAKVAODCDH-UHFFFAOYSA-N 0.000 claims 2
- ZIHIZUXCVGENMF-UHFFFAOYSA-N 1-[5-chloro-6-(difluoromethoxy)quinolin-2-yl]-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C(Cl)=C(OC(F)F)C=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 ZIHIZUXCVGENMF-UHFFFAOYSA-N 0.000 claims 2
- AIUXFSOPHUPUAE-UHFFFAOYSA-N 1-[5-chloro-6-(trifluoromethoxy)quinolin-2-yl]-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C(Cl)=C(OC(F)(F)F)C=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 AIUXFSOPHUPUAE-UHFFFAOYSA-N 0.000 claims 2
- ZBRAJOQFSNYJMF-UHFFFAOYSA-N 1-[6,7-bis(difluoromethoxy)naphthalen-2-yl]-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C=C(OC(F)F)C(OC(F)F)=CC2=CC=1C(O)(C(C)C)C1=CNN=N1 ZBRAJOQFSNYJMF-UHFFFAOYSA-N 0.000 claims 2
- KJTKVKVPHPNQSU-UHFFFAOYSA-N 1-[6,7-bis(difluoromethoxy)quinolin-2-yl]-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C=C(OC(F)F)C(OC(F)F)=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 KJTKVKVPHPNQSU-UHFFFAOYSA-N 0.000 claims 2
- DLIXONPOBWMUIO-UHFFFAOYSA-N 1-[6-(difluoromethoxy)naphthalen-2-yl]-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C=C(OC(F)F)C=CC2=CC=1C(O)(C(C)C)C1=CNN=N1 DLIXONPOBWMUIO-UHFFFAOYSA-N 0.000 claims 2
- AXIPFQNHVNPUSH-UHFFFAOYSA-N 1-[6-chloro-5-(trifluoromethyl)quinolin-2-yl]-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C(C(F)(F)F)=C(Cl)C=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 AXIPFQNHVNPUSH-UHFFFAOYSA-N 0.000 claims 2
- KSQPNKNCQWCKRG-UHFFFAOYSA-N 1-[7-chloro-6-(trifluoromethyl)quinolin-2-yl]-2-methyl-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C=C(C(F)(F)F)C(Cl)=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 KSQPNKNCQWCKRG-UHFFFAOYSA-N 0.000 claims 2
- WUQFUZUYABSJAQ-UHFFFAOYSA-N 2-[1-hydroxy-2-methyl-1-(2h-triazol-4-yl)propyl]-5-(trifluoromethyl)quinoline-6-carbonitrile Chemical compound C=1C=C2C(C(F)(F)F)=C(C#N)C=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 WUQFUZUYABSJAQ-UHFFFAOYSA-N 0.000 claims 2
- WLANGOHXOSKDPZ-UHFFFAOYSA-N 2-methyl-1-(2h-triazol-4-yl)-1-[6-(trifluoromethoxy)quinolin-2-yl]propan-1-ol Chemical compound C=1C=C2C=C(OC(F)(F)F)C=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 WLANGOHXOSKDPZ-UHFFFAOYSA-N 0.000 claims 2
- YDAJLXIARQWZRW-UHFFFAOYSA-N 2-methyl-1-(6-methylsulfanylquinolin-2-yl)-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C1=CC2=CC(SC)=CC=C2N=C1C(O)(C(C)C)C1=CNN=N1 YDAJLXIARQWZRW-UHFFFAOYSA-N 0.000 claims 2
- MZRURODHGHUBKV-UHFFFAOYSA-N 2-methyl-1-[5-thiophen-2-yl-6-(2,2,2-trifluoroethoxy)quinolin-2-yl]-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C(C=3SC=CC=3)=C(OCC(F)(F)F)C=CC2=NC=1C(O)(C(C)C)C1=CN=NN1 MZRURODHGHUBKV-UHFFFAOYSA-N 0.000 claims 2
- FPFLLZAGPFEDBQ-UHFFFAOYSA-N 2-methyl-1-[6-(1,3-oxazol-5-yl)naphthalen-2-yl]-1-(2h-triazol-4-yl)propan-1-ol Chemical compound C=1C=C2C=C(C=3OC=NC=3)C=CC2=CC=1C(O)(C(C)C)C1=CNN=N1 FPFLLZAGPFEDBQ-UHFFFAOYSA-N 0.000 claims 2
- -1 6- (Difluoromethoxy) -5- (thiophen-2-yl) quinolin-2-yl Chemical group 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 230000001780 adrenocortical effect Effects 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- LNCAMLLVHZJNDI-UHFFFAOYSA-N 2-methyl-1-(2h-triazol-4-yl)-1-[6-(2,2,2-trifluoroethoxy)naphthalen-2-yl]propan-1-ol Chemical compound C=1C=C2C=C(OCC(F)(F)F)C=CC2=CC=1C(O)(C(C)C)C1=CNN=N1 LNCAMLLVHZJNDI-UHFFFAOYSA-N 0.000 claims 1
- KTCVWHLVIFVXLY-UHFFFAOYSA-N 2-methyl-1-(2h-triazol-4-yl)-1-[6-(2,2,2-trifluoroethoxy)quinolin-2-yl]propan-1-ol Chemical compound C=1C=C2C=C(OCC(F)(F)F)C=CC2=NC=1C(O)(C(C)C)C1=CNN=N1 KTCVWHLVIFVXLY-UHFFFAOYSA-N 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 201000005670 Anovulation Diseases 0.000 claims 1
- 206010002659 Anovulatory cycle Diseases 0.000 claims 1
- 206010061692 Benign muscle neoplasm Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 206010020112 Hirsutism Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 201000004458 Myoma Diseases 0.000 claims 1
- 208000010195 Onychomycosis Diseases 0.000 claims 1
- 206010036590 Premature baby Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000012931 Urologic disease Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 1
- 206010047486 Virilism Diseases 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 230000001919 adrenal effect Effects 0.000 claims 1
- 239000003732 agents acting on the eye Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 206010068168 androgenetic alopecia Diseases 0.000 claims 1
- 201000002996 androgenic alopecia Diseases 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 231100000552 anovulation Toxicity 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 239000003429 antifungal agent Substances 0.000 claims 1
- 229940121375 antifungal agent Drugs 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 208000030270 breast disease Diseases 0.000 claims 1
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims 1
- 229940125692 cardiovascular agent Drugs 0.000 claims 1
- 239000002327 cardiovascular agent Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 231100000599 cytotoxic agent Toxicity 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000000262 estrogen Substances 0.000 claims 1
- 229940011871 estrogen Drugs 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 235000019000 fluorine Nutrition 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 239000004083 gastrointestinal agent Substances 0.000 claims 1
- 229940125695 gastrointestinal agent Drugs 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 201000010066 hyperandrogenism Diseases 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000000509 infertility Diseases 0.000 claims 1
- 231100000535 infertility Toxicity 0.000 claims 1
- 230000036512 infertility Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000010260 leiomyoma Diseases 0.000 claims 1
- 231100000794 masculinization Toxicity 0.000 claims 1
- 229940125702 ophthalmic agent Drugs 0.000 claims 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
- 230000002028 premature Effects 0.000 claims 1
- 201000004240 prostatic hypertrophy Diseases 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 claims 1
- 201000005882 tinea unguium Diseases 0.000 claims 1
- 208000014001 urinary system disease Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- 208000010579 uterine corpus leiomyoma Diseases 0.000 claims 1
- 201000007954 uterine fibroid Diseases 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
- ROWUDZIYFDKEQM-UHFFFAOYSA-N C(Cc1ccccc1)CNc1cccc(-c2cnn[nH]2)c1 Chemical compound C(Cc1ccccc1)CNc1cccc(-c2cnn[nH]2)c1 ROWUDZIYFDKEQM-UHFFFAOYSA-N 0.000 description 1
- XWSXOJIGZDEFKO-UHFFFAOYSA-N C(c1c[o]cc1)Nc1cccc(-c2cnn[nH]2)c1 Chemical compound C(c1c[o]cc1)Nc1cccc(-c2cnn[nH]2)c1 XWSXOJIGZDEFKO-UHFFFAOYSA-N 0.000 description 1
- ICNTYHGHXVHTHC-UHFFFAOYSA-N C(c1ccccc1)Nc1cc(-c2cnn[nH]2)ccc1 Chemical compound C(c1ccccc1)Nc1cc(-c2cnn[nH]2)ccc1 ICNTYHGHXVHTHC-UHFFFAOYSA-N 0.000 description 1
- ATKJYZIOFWPDJD-UHFFFAOYSA-N C1Oc(c(-c2cnn[nH]2)ccc2)c2O1 Chemical compound C1Oc(c(-c2cnn[nH]2)ccc2)c2O1 ATKJYZIOFWPDJD-UHFFFAOYSA-N 0.000 description 1
- UQNMMYVQLOFKSL-UHFFFAOYSA-N C1Oc2cc(-c3cnn[nH]3)ccc2O1 Chemical compound C1Oc2cc(-c3cnn[nH]3)ccc2O1 UQNMMYVQLOFKSL-UHFFFAOYSA-N 0.000 description 1
- YHDCPALYQURDMR-UHFFFAOYSA-N C=[Br]c(cccc1)c1-c1cnn[nH]1 Chemical compound C=[Br]c(cccc1)c1-c1cnn[nH]1 YHDCPALYQURDMR-UHFFFAOYSA-N 0.000 description 1
- UKYMYESZZTWGIS-UHFFFAOYSA-N CC1C(CCNc2cccc(-c3cnn[nH]3)c2)=CC=CC1c1ccc(CNc2cccc(-c3cnn[nH]3)c2)[o]1 Chemical compound CC1C(CCNc2cccc(-c3cnn[nH]3)c2)=CC=CC1c1ccc(CNc2cccc(-c3cnn[nH]3)c2)[o]1 UKYMYESZZTWGIS-UHFFFAOYSA-N 0.000 description 1
- LPVPGKCWLFFGFF-UHFFFAOYSA-N COc(cc1)ccc1-c1cnn[nH]1 Chemical compound COc(cc1)ccc1-c1cnn[nH]1 LPVPGKCWLFFGFF-UHFFFAOYSA-N 0.000 description 1
- XQHCBHNLRWLGQS-UHFFFAOYSA-N Cc1cc(-c2cnn[nH]2)ccc1 Chemical compound Cc1cc(-c2cnn[nH]2)ccc1 XQHCBHNLRWLGQS-UHFFFAOYSA-N 0.000 description 1
- IYTHSSNIJXFAQN-UHFFFAOYSA-N Cc1cccnc1-c1cnn[nH]1 Chemical compound Cc1cccnc1-c1cnn[nH]1 IYTHSSNIJXFAQN-UHFFFAOYSA-N 0.000 description 1
- FYQBMGGHUIYNAG-UHFFFAOYSA-N Clc(cc1)ccc1Sc(cccc1)c1-c1cnn[nH]1 Chemical compound Clc(cc1)ccc1Sc(cccc1)c1-c1cnn[nH]1 FYQBMGGHUIYNAG-UHFFFAOYSA-N 0.000 description 1
- KYQRWVUQWNZHFU-UHFFFAOYSA-N Fc(cc1)ccc1-c1cnn[nH]1 Chemical compound Fc(cc1)ccc1-c1cnn[nH]1 KYQRWVUQWNZHFU-UHFFFAOYSA-N 0.000 description 1
- XQNLLPNGLMIYRT-UHFFFAOYSA-N Fc1ccccc1-c1cnn[nH]1 Chemical compound Fc1ccccc1-c1cnn[nH]1 XQNLLPNGLMIYRT-UHFFFAOYSA-N 0.000 description 1
- 0 I*(cc1)ccc1-c1cnn[n]1 Chemical compound I*(cc1)ccc1-c1cnn[n]1 0.000 description 1
- CONLIJVDXFCUGC-UHFFFAOYSA-N O=C(c1ccccc1)Nc1cccc(-c2cnn[nH]2)c1 Chemical compound O=C(c1ccccc1)Nc1cccc(-c2cnn[nH]2)c1 CONLIJVDXFCUGC-UHFFFAOYSA-N 0.000 description 1
- ZQTHEZHPRGQYNQ-UHFFFAOYSA-N OC1(CCCCC1)c1cnn[nH]1 Chemical compound OC1(CCCCC1)c1cnn[nH]1 ZQTHEZHPRGQYNQ-UHFFFAOYSA-N 0.000 description 1
- DCERZYFATQLVJN-UHFFFAOYSA-N c1c(-c2cnn[nH]2)[o]c2ccccc12 Chemical compound c1c(-c2cnn[nH]2)[o]c2ccccc12 DCERZYFATQLVJN-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41339510P | 2010-11-13 | 2010-11-13 | |
| US61/413,395 | 2010-11-13 | ||
| PCT/US2011/060166 WO2012064943A2 (en) | 2010-11-13 | 2011-11-10 | Metalloenzyme inhibitor compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015199620A Division JP2016094390A (ja) | 2010-11-13 | 2015-10-07 | 金属酵素阻害化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014501717A JP2014501717A (ja) | 2014-01-23 |
| JP2014501717A5 true JP2014501717A5 (https=) | 2014-05-15 |
| JP5828343B2 JP5828343B2 (ja) | 2015-12-02 |
Family
ID=46051557
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013538883A Active JP5828343B2 (ja) | 2010-11-13 | 2011-11-10 | 金属酵素阻害化合物 |
| JP2015199620A Pending JP2016094390A (ja) | 2010-11-13 | 2015-10-07 | 金属酵素阻害化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015199620A Pending JP2016094390A (ja) | 2010-11-13 | 2015-10-07 | 金属酵素阻害化合物 |
Country Status (13)
| Country | Link |
|---|---|
| US (5) | US8389543B2 (https=) |
| EP (2) | EP2638021B1 (https=) |
| JP (2) | JP5828343B2 (https=) |
| KR (2) | KR101848077B1 (https=) |
| CN (2) | CN103339115B (https=) |
| AU (2) | AU2011326487B2 (https=) |
| BR (1) | BR112013011830B1 (https=) |
| CA (1) | CA2817691C (https=) |
| EA (1) | EA024197B1 (https=) |
| ES (1) | ES2703498T3 (https=) |
| PT (1) | PT2638021T (https=) |
| TW (1) | TWI600647B (https=) |
| WO (1) | WO2012064943A2 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101926320B1 (ko) | 2010-08-04 | 2018-12-06 | 펠피큐어 파마슈티걸즈 아이엔씨 | 전립선 암종의 치료를 위한 병용 요법 |
| KR101848077B1 (ko) * | 2010-11-13 | 2018-04-11 | 이노크린 파마슈티컬즈, 인크. | 금속효소 억제제 화합물 |
| WO2013109998A1 (en) * | 2012-01-20 | 2013-07-25 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| KR20150087400A (ko) | 2012-11-20 | 2015-07-29 | 버텍스 파마슈티칼스 인코포레이티드 | 인돌아민 2,3-디옥시게나제의 억제제로서 유용한 화합물 |
| CA2902335C (en) * | 2013-03-14 | 2021-09-14 | Pellficure Pharmaceuticals, Inc. | Novel therapy for prostate carcinoma |
| WO2015070366A1 (en) | 2013-11-12 | 2015-05-21 | Merck Sharp & Dohme Corp. | Aryl linked imidazole and triazole derivatives and methods of use thereof for improving the pharmacokinetics of a drug |
| US9738613B2 (en) | 2015-05-18 | 2017-08-22 | National Central University | Substituted 1,2,3-triazoles as antitumor agents |
| CN114989205A (zh) | 2016-12-22 | 2022-09-02 | 卡里塞拉生物科学股份公司 | 用于抑制精氨酸酶活性的组合物和方法 |
| JP7227157B2 (ja) * | 2016-12-29 | 2023-02-21 | フェーズバイオ ファーマシューティカルズ，インコーポレイテッド | 金属酵素阻害剤化合物 |
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2011
- 2011-11-10 KR KR1020137015117A patent/KR101848077B1/ko active Active
- 2011-11-10 JP JP2013538883A patent/JP5828343B2/ja active Active
- 2011-11-10 ES ES11839513T patent/ES2703498T3/es active Active
- 2011-11-10 CN CN201180064835.8A patent/CN103339115B/zh active Active
- 2011-11-10 PT PT11839513T patent/PT2638021T/pt unknown
- 2011-11-10 BR BR112013011830-0A patent/BR112013011830B1/pt active IP Right Grant
- 2011-11-10 EP EP11839513.6A patent/EP2638021B1/en active Active
- 2011-11-10 US US13/293,891 patent/US8389543B2/en active Active
- 2011-11-10 WO PCT/US2011/060166 patent/WO2012064943A2/en not_active Ceased
- 2011-11-10 KR KR1020187009616A patent/KR20180039185A/ko not_active Withdrawn
- 2011-11-10 CN CN201610627095.9A patent/CN106243051B/zh not_active Expired - Fee Related
- 2011-11-10 CA CA2817691A patent/CA2817691C/en active Active
- 2011-11-10 AU AU2011326487A patent/AU2011326487B2/en active Active
- 2011-11-10 EA EA201390704A patent/EA024197B1/ru unknown
- 2011-11-10 EP EP18196254.9A patent/EP3483147A1/en not_active Withdrawn
- 2011-11-11 TW TW100141218A patent/TWI600647B/zh active
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