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 (enExample) | 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 (enExample) |
| EP (2) | EP2638021B1 (enExample) |
| JP (2) | JP5828343B2 (enExample) |
| KR (2) | KR20180039185A (enExample) |
| CN (2) | CN106243051B (enExample) |
| AU (2) | AU2011326487B2 (enExample) |
| BR (1) | BR112013011830B1 (enExample) |
| CA (1) | CA2817691C (enExample) |
| EA (1) | EA024197B1 (enExample) |
| ES (1) | ES2703498T3 (enExample) |
| PT (1) | PT2638021T (enExample) |
| TW (1) | TWI600647B (enExample) |
| WO (1) | WO2012064943A2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101594660B1 (ko) | 2010-08-04 | 2016-02-16 | 펠피큐어 파마슈티걸즈 아이엔씨 | 전립선 암종의 치료를 위한 병용 요법 |
| EP2638021B1 (en) * | 2010-11-13 | 2018-09-26 | Innocrin Pharmaceuticals, Inc. | 1-(6,7-Bis(difluoromethoxy)naphthalen-2-yl)-2-methyl-1-(1H-1,2,3-triazol-4-yl)propan-1-ol as inhibitor of CYP17 for the treatment of androgen dependent diseases like prostate cancer |
| IN2014DN06792A (enExample) * | 2012-01-20 | 2015-05-22 | Viamet Pharmaceuticals Inc | |
| EP2922847A1 (en) | 2012-11-20 | 2015-09-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase |
| AU2014241816B9 (en) * | 2013-03-14 | 2019-02-14 | 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 |
| WO2018119440A1 (en) | 2016-12-22 | 2018-06-28 | Calithera Biosciences, Inc. | Compositions and methods for inhibiting arginase activity |
| CA3055292A1 (en) * | 2016-12-29 | 2018-07-05 | Selenity Therapeutics (Bermuda), Ltd. | Metalloenzyme inhibitor compounds |
| WO2018136437A2 (en) | 2017-01-17 | 2018-07-26 | Tesaro, Inc. | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
| US20210292410A1 (en) * | 2017-12-07 | 2021-09-23 | Morphosys Ag | Treatment paradigm for an anti-cd19 antibody and venetoclax combination treatment |
| WO2019113312A1 (en) * | 2017-12-08 | 2019-06-13 | Innocrin Pharmaceuticals, Inc. | Anticancer compound process |
| WO2019182743A1 (en) * | 2018-03-20 | 2019-09-26 | Innocrin Pharmaceuticals, Inc. | Compositions for the treatment of brain tumors |
| EP3823604A4 (en) | 2018-07-17 | 2022-03-16 | Board of Regents, The University of Texas System | COMPOUNDS AS INHIBITORS OF INDOLAMINE-2,3-DIOXYGENASE AND/OR TRYPTOPHANE DIOXYGENASE |
| WO2020077197A1 (en) * | 2018-10-11 | 2020-04-16 | Innocrin Pharmaceuticals, Inc. | Compositions for the treatment of brain tumors |
| CN110256342B (zh) * | 2019-07-16 | 2022-06-07 | 河南省科学院化学研究所有限公司 | 一种2-氰基喹啉衍生物的合成方法 |
| CN114957215B (zh) * | 2022-01-13 | 2023-03-21 | 渤海大学 | 亚甲基桥连喹啉和1,2,3-三唑双杂环化合物及其制备方法与应用 |
| CN120960385B (zh) * | 2025-08-01 | 2026-07-17 | 上海交通大学医学院附属第九人民医院 | 5α–还原酶降解分子及其制备方法和应用 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5087240A (en) | 1983-08-18 | 1992-02-11 | Drug Delivery Systems Inc. | Transdermal drug patch with conductive fibers |
| US4921475A (en) | 1983-08-18 | 1990-05-01 | Drug Delivery Systems Inc. | Transdermal drug patch with microtubes |
| US4738851A (en) | 1985-09-27 | 1988-04-19 | University Of Iowa Research Foundation, Inc. | Controlled release ophthalmic gel formulation |
| US5163899A (en) | 1987-03-20 | 1992-11-17 | Drug Delivery Systems Inc. | Transdermal drug delivery system |
| US5312325A (en) | 1987-05-28 | 1994-05-17 | Drug Delivery Systems Inc | Pulsating transdermal drug delivery system |
| GB8804164D0 (en) | 1988-02-23 | 1988-03-23 | Tucker J M | Bandage for administering physiologically active compound |
| US4882150A (en) | 1988-06-03 | 1989-11-21 | Kaufman Herbert E | Drug delivery system |
| US5008110A (en) | 1988-11-10 | 1991-04-16 | The Procter & Gamble Company | Storage-stable transdermal patch |
| US5088977A (en) | 1988-12-21 | 1992-02-18 | Drug Delivery Systems Inc. | Electrical transdermal drug applicator with counteractor and method of drug delivery |
| US5521222A (en) | 1989-09-28 | 1996-05-28 | Alcon Laboratories, Inc. | Topical ophthalmic pharmaceutical vehicles |
| CA2031376A1 (en) | 1989-12-04 | 1991-06-05 | Bahram Farhadieh | Single layer transdermal drug administration system |
| US5077033A (en) | 1990-08-07 | 1991-12-31 | Mediventures Inc. | Ophthalmic drug delivery with thermo-irreversible gels of polxoxyalkylene polymer and ionic polysaccharide |
| DK0495421T3 (da) | 1991-01-15 | 1996-12-09 | Alcon Lab Inc | Anvendelse af carragenaner i topiske ophthalmiske sammensætninger |
| US5352456A (en) | 1991-10-10 | 1994-10-04 | Cygnus Therapeutic Systems | Device for administering drug transdermally which provides an initial pulse of drug |
| CA2123809A1 (en) | 1991-12-18 | 1993-06-24 | Debra L. Wilfong | Multilayered barrier structures |
| ATE132381T1 (de) | 1992-01-29 | 1996-01-15 | Voelkl Franz Ski | Ballspielschläger, insbesondere tennisschläger |
| IL114193A (en) | 1994-06-20 | 2000-02-29 | Teva Pharma | Ophthalmic pharmaceutical compositions based on sodium alginate |
| ES2094688B1 (es) | 1994-08-08 | 1997-08-01 | Cusi Lab | Manoemulsion del tipo de aceite en agua, util como vehiculo oftalmico y procedimiento para su preparacion. |
| IT1283911B1 (it) | 1996-02-05 | 1998-05-07 | Farmigea Spa | Soluzioni oftalmiche viscosizzate con polisaccaridi della gomma di tamarindo |
| US5800807A (en) | 1997-01-29 | 1998-09-01 | Bausch & Lomb Incorporated | Ophthalmic compositions including glycerin and propylene glycol |
| US6261547B1 (en) | 1998-04-07 | 2001-07-17 | Alcon Manufacturing, Ltd. | Gelling ophthalmic compositions containing xanthan gum |
| US6573289B1 (en) | 1998-04-23 | 2003-06-03 | Takeda Chemical Industries, Ltd. | Naphthalene derivatives, their production and use |
| US6197934B1 (en) | 1998-05-22 | 2001-03-06 | Collagenesis, Inc. | Compound delivery using rapidly dissolving collagen film |
| JP2003530438A (ja) * | 2000-04-12 | 2003-10-14 | スミスクライン・ビーチャム・コーポレイション | 化合物および方法 |
| JP2005508951A (ja) * | 2001-10-12 | 2005-04-07 | スミスクライン・ビーチャム・コーポレイション | 化合物および方法 |
| MXPA05001819A (es) | 2002-08-22 | 2005-04-19 | Syngenta Participations Ag | Derivados de 1,2,3-triazol como microbicidas. |
| CN1819996B (zh) * | 2003-07-10 | 2010-10-27 | Osi制药公司 | 作为细胞色素p450抑制剂的亚萘基衍生物 |
| US7504424B2 (en) * | 2004-07-16 | 2009-03-17 | Schering Corporation | Compounds for the treatment of inflammatory disorders |
| US7488745B2 (en) | 2004-07-16 | 2009-02-10 | Schering Corporation | Compounds for the treatment of inflammatory disorders |
| AU2008236679B2 (en) * | 2007-04-03 | 2013-11-28 | Fmc Corporation | Substituted benzene fungicides |
| JP2010523599A (ja) * | 2007-04-05 | 2010-07-15 | シーメンス メディカル ソリューションズ ユーエスエー インコーポレイテッド | クリックケミストリーを使用した炭酸脱水酵素−ｉｘのための分子イメージングプローブの開発 |
| EP2234608A2 (en) * | 2007-12-11 | 2010-10-06 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
| WO2009120565A2 (en) * | 2008-03-25 | 2009-10-01 | University Of Maryland, Baltimore | Novel prodrugs of c-17-heteroaryl steroidal cyp17 inhibitors/antiandrogens: synthesis, in vitro biological activities, pharmacokinetics and antitumor activity |
| WO2010032874A1 (ja) | 2008-09-19 | 2010-03-25 | 住友化学株式会社 | 農業用組成物 |
| BRPI0920681A2 (pt) * | 2008-10-28 | 2015-12-29 | Biomarin Pharm Inc | inibidores de decahidro-1h-indenoquinolinona e decahidro-3h-ciclopentafenantridinona de cyp17 |
| WO2011088160A2 (en) | 2010-01-15 | 2011-07-21 | Biomarin Pharmaceutical Inc. | Novel cyp17 inhibitors |
| EP2638021B1 (en) * | 2010-11-13 | 2018-09-26 | Innocrin Pharmaceuticals, Inc. | 1-(6,7-Bis(difluoromethoxy)naphthalen-2-yl)-2-methyl-1-(1H-1,2,3-triazol-4-yl)propan-1-ol as inhibitor of CYP17 for the treatment of androgen dependent diseases like prostate cancer |
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2011
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