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) | EP3483147A1 (https=) |
| JP (2) | JP5828343B2 (https=) |
| KR (2) | KR101848077B1 (https=) |
| CN (2) | CN106243051B (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 |
|---|---|---|---|---|
| KR101823275B1 (ko) | 2010-08-04 | 2018-03-08 | 펠피큐어 파마슈티걸즈 아이엔씨 | 전립선 암종의 치료를 위한 병용 요법 |
| EP3483147A1 (en) * | 2010-11-13 | 2019-05-15 | Innocrin Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| ES2774267T3 (es) * | 2012-01-20 | 2020-07-20 | Mycovia Pharmaceuticals Inc | Compuestos inhibidores de metaloenzimas |
| JP2016501203A (ja) | 2012-11-20 | 2016-01-18 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インドールアミン２，３−ジオキシゲナーゼの阻害剤として有用な化合物 |
| EP2968219B1 (en) * | 2013-03-14 | 2019-04-24 | 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 |
| SMT202100573T1 (it) | 2016-12-22 | 2021-11-12 | Calithera Biosciences Inc | Composizioni e metodi per l'inibizione dell'attivita' dell'arginasi |
| FI3562487T3 (fi) * | 2016-12-29 | 2023-12-14 | Ji Xing Pharmaceuticals Hong Kong Ltd | Metalloentsyymi-inhibiittoriyhdisteitä |
| JP2020506895A (ja) | 2017-01-17 | 2020-03-05 | ボード オブ レジェンツ, ザ ユニバーシティ オブ テキサス システムBoard Of Regents, The University Of Texas System | インドールアミン２，３−ジオキシゲナーゼおよび／またはトリプトファンジオキシゲナーゼの阻害剤として有用な化合物 |
| 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 |
| WO2020018670A1 (en) | 2018-07-17 | 2020-01-23 | Board Of Regents, The University Of Texas System | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
| US12357615B2 (en) * | 2018-10-11 | 2025-07-15 | Kembi Therapeutics Pty Ltd | 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 |
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 |
| EP0431519B1 (en) | 1989-12-04 | 1994-06-15 | G.D. Searle & Co. | System for transdermal albuterol administration |
| US5077033A (en) | 1990-08-07 | 1991-12-31 | Mediventures Inc. | Ophthalmic drug delivery with thermo-irreversible gels of polxoxyalkylene polymer and ionic polysaccharide |
| ATE141502T1 (de) | 1991-01-15 | 1996-09-15 | Alcon Lab Inc | Verwendung von karrageenan in topischen ophthalmologischen zusammensetzungen |
| US5352456A (en) | 1991-10-10 | 1994-10-04 | Cygnus Therapeutic Systems | Device for administering drug transdermally which provides an initial pulse of drug |
| DE69228827T2 (de) | 1991-12-18 | 1999-10-21 | Minnesota Mining And Mfg. Co., Saint Paul | Mehrschichtige sperrstrukturen |
| EP0553769B1 (de) | 1992-01-29 | 1996-01-03 | FRANZ VÖLKL GmbH & CO. SKI UND TENNIS SPORTARTIKELFABRIK KG | 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 |
| WO1999054309A1 (en) * | 1998-04-23 | 1999-10-28 | 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 |
| US20030220371A1 (en) * | 2000-04-12 | 2003-11-27 | Kallander Lara S. | Compounds and methods |
| WO2003031434A1 (en) * | 2001-10-12 | 2003-04-17 | Smith Kline Beecham Corporation | Compounds and methods |
| WO2004018438A2 (en) * | 2002-08-22 | 2004-03-04 | Syngenta Participations Ag | Microbiocidal (e.g. fungicidal) 1,2,3-triazole derivatives |
| WO2005007631A1 (en) * | 2003-07-10 | 2005-01-27 | Osi Pharmaceuticals, Inc. | Naphthylene derivatives as cytochrome p450 inhibitors |
| 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 |
| WO2008124092A2 (en) * | 2007-04-03 | 2008-10-16 | E. I. Du Pont De Nemours And Company | Substituted benzene fungicides |
| WO2008124703A2 (en) * | 2007-04-05 | 2008-10-16 | Siemens Medical Solutions Usa, Inc. | Development of molecular imaging probes for carbonic anhydrase-ix using click chemistry |
| JP2011517313A (ja) * | 2007-12-11 | 2011-06-02 | ビアメト ファーマシューティカルズ，インク． | 金属結合部分を標的化部分と組み合わせて使用する金属酵素阻害剤 |
| GB2470700B (en) | 2008-03-25 | 2012-08-08 | Univ Maryland | C-17 heteroaryl steroidal CYP17 inhibitors |
| WO2010032874A1 (ja) | 2008-09-19 | 2010-03-25 | 住友化学株式会社 | 農業用組成物 |
| EP2362872A4 (en) * | 2008-10-28 | 2012-05-30 | Biomarin Pharm Inc | DECAHYDRO-1H-INDENOCHINOLINONE AND DECAHYDRO-3H-CYCLOPENTAPHENANTHRIDINONE CYP17 HEMMER |
| WO2011088160A2 (en) * | 2010-01-15 | 2011-07-21 | Biomarin Pharmaceutical Inc. | Novel cyp17 inhibitors |
| EP3483147A1 (en) * | 2010-11-13 | 2019-05-15 | Innocrin Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
-
2011
- 2011-11-10 EP EP18196254.9A patent/EP3483147A1/en not_active Withdrawn
- 2011-11-10 PT PT11839513T patent/PT2638021T/pt unknown
- 2011-11-10 KR KR1020137015117A patent/KR101848077B1/ko active Active
- 2011-11-10 CA CA2817691A patent/CA2817691C/en active Active
- 2011-11-10 WO PCT/US2011/060166 patent/WO2012064943A2/en not_active Ceased
- 2011-11-10 US US13/293,891 patent/US8389543B2/en active Active
- 2011-11-10 CN CN201610627095.9A patent/CN106243051B/zh not_active Expired - Fee Related
- 2011-11-10 ES ES11839513T patent/ES2703498T3/es active Active
- 2011-11-10 CN CN201180064835.8A patent/CN103339115B/zh active Active
- 2011-11-10 JP JP2013538883A patent/JP5828343B2/ja active Active
- 2011-11-10 EP EP11839513.6A patent/EP2638021B1/en active Active
- 2011-11-10 BR BR112013011830-0A patent/BR112013011830B1/pt active IP Right Grant
- 2011-11-10 EA EA201390704A patent/EA024197B1/ru unknown
- 2011-11-10 KR KR1020187009616A patent/KR20180039185A/ko not_active Withdrawn
- 2011-11-10 AU AU2011326487A patent/AU2011326487B2/en active Active
- 2011-11-11 TW TW100141218A patent/TWI600647B/zh active
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2013
- 2013-03-04 US US13/784,466 patent/US8623892B2/en active Active
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2014
- 2014-01-06 US US14/148,318 patent/US20140121248A1/en not_active Abandoned
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2015
- 2015-10-07 JP JP2015199620A patent/JP2016094390A/ja active Pending
-
2017
- 2017-02-02 US US15/423,235 patent/US20170143694A1/en not_active Abandoned
- 2017-06-01 AU AU2017203691A patent/AU2017203691A1/en not_active Abandoned
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2018
- 2018-04-03 US US15/944,397 patent/US20180221364A1/en not_active Abandoned
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