JP2014504287A5 - - Google Patents
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- Publication number
- JP2014504287A5 JP2014504287A5 JP2013543412A JP2013543412A JP2014504287A5 JP 2014504287 A5 JP2014504287 A5 JP 2014504287A5 JP 2013543412 A JP2013543412 A JP 2013543412A JP 2013543412 A JP2013543412 A JP 2013543412A JP 2014504287 A5 JP2014504287 A5 JP 2014504287A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- optionally substituted
- propyl
- methyl
- triazol
- 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 11
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 210000003169 central nervous system Anatomy 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 239000003098 androgen Substances 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- OIHNIRKJTUBHQG-UHFFFAOYSA-N 1-[1-(6-ethoxynaphthalen-2-yl)-2-methylpropyl]triazole Chemical compound C1=CC2=CC(OCC)=CC=C2C=C1C(C(C)C)N1C=CN=N1 OIHNIRKJTUBHQG-UHFFFAOYSA-N 0.000 claims 2
- VPMCSIZSLMFXIF-UHFFFAOYSA-N 1-[1-(6-methoxynaphthalen-2-yl)-2-methylpropyl]triazole Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C(C)C)N1C=CN=N1 VPMCSIZSLMFXIF-UHFFFAOYSA-N 0.000 claims 2
- OPUZJYSNTRJRPC-UHFFFAOYSA-N 1-[1-[6,7-bis(difluoromethoxy)naphthalen-2-yl]-2-methylpropyl]triazole Chemical compound C=1C=C2C=C(OC(F)F)C(OC(F)F)=CC2=CC=1C(C(C)C)N1C=CN=N1 OPUZJYSNTRJRPC-UHFFFAOYSA-N 0.000 claims 2
- OZWDNOYCEUNWNU-UHFFFAOYSA-N 1-[1-[6-(difluoromethoxy)naphthalen-2-yl]-2-methylpropyl]triazole Chemical compound C=1C=C2C=C(OC(F)F)C=CC2=CC=1C(C(C)C)N1C=CN=N1 OZWDNOYCEUNWNU-UHFFFAOYSA-N 0.000 claims 2
- SHQKFLSRHSBIRP-UHFFFAOYSA-N 1-[2-methyl-1-(6-propan-2-yloxynaphthalen-2-yl)propyl]triazole Chemical compound C1=CC2=CC(OC(C)C)=CC=C2C=C1C(C(C)C)N1C=CN=N1 SHQKFLSRHSBIRP-UHFFFAOYSA-N 0.000 claims 2
- ROVPTODVGPBOGN-UHFFFAOYSA-N 1-[2-methyl-1-[6-(2,2,2-trifluoroethoxy)naphthalen-2-yl]propyl]triazole Chemical compound C=1C=C2C=C(OCC(F)(F)F)C=CC2=CC=1C(C(C)C)N1C=CN=N1 ROVPTODVGPBOGN-UHFFFAOYSA-N 0.000 claims 2
- PILDTESNLOTIDL-UHFFFAOYSA-N 2-[2-methyl-1-(triazol-1-yl)propyl]-6-(trifluoromethoxy)quinoline Chemical compound C=1C=C2C=C(OC(F)(F)F)C=CC2=NC=1C(C(C)C)N1C=CN=N1 PILDTESNLOTIDL-UHFFFAOYSA-N 0.000 claims 2
- UCOZQLQTNHTMKM-UHFFFAOYSA-N 2-[2-methyl-1-(triazol-1-yl)propyl]quinoline-6-carbonitrile Chemical compound C=1C=C2C=C(C#N)C=CC2=NC=1C(C(C)C)N1C=CN=N1 UCOZQLQTNHTMKM-UHFFFAOYSA-N 0.000 claims 2
- PQYFWSPUFIBXEE-UHFFFAOYSA-N 5,6-dichloro-2-[2-methyl-1-(triazol-1-yl)propyl]quinoline Chemical compound C=1C=C2C(Cl)=C(Cl)C=CC2=NC=1C(C(C)C)N1C=CN=N1 PQYFWSPUFIBXEE-UHFFFAOYSA-N 0.000 claims 2
- IZUMOLSDEIAYAF-UHFFFAOYSA-N 5-chloro-2-[2-methyl-1-(triazol-1-yl)propyl]-6-(2,2,2-trifluoroethoxy)quinoline Chemical compound C=1C=C2C(Cl)=C(OCC(F)(F)F)C=CC2=NC=1C(C(C)C)N1C=CN=N1 IZUMOLSDEIAYAF-UHFFFAOYSA-N 0.000 claims 2
- DFHIHQGTLHUGNZ-UHFFFAOYSA-N 5-chloro-2-[2-methyl-1-(triazol-1-yl)propyl]-6-(trifluoromethoxy)quinoline Chemical compound C=1C=C2C(Cl)=C(OC(F)(F)F)C=CC2=NC=1C(C(C)C)N1C=CN=N1 DFHIHQGTLHUGNZ-UHFFFAOYSA-N 0.000 claims 2
- REQUPWLVEUTHMX-UHFFFAOYSA-N 5-chloro-6-(difluoromethoxy)-2-[2-methyl-1-(triazol-1-yl)propyl]quinoline Chemical compound C=1C=C2C(Cl)=C(OC(F)F)C=CC2=NC=1C(C(C)C)N1C=CN=N1 REQUPWLVEUTHMX-UHFFFAOYSA-N 0.000 claims 2
- LBYYISIFGBECDJ-UHFFFAOYSA-N 5-fluoro-2-[2-methyl-1-(triazol-1-yl)propyl]-6-thiophen-2-ylquinoline Chemical compound C1=CN=NN1C(C(C)C)C(N=C1C=C2)=CC=C1C(F)=C2C1=CC=CS1 LBYYISIFGBECDJ-UHFFFAOYSA-N 0.000 claims 2
- ACRSZAYEYQXIHV-UHFFFAOYSA-N 6,7-bis(difluoromethoxy)-2-[2-methyl-1-(triazol-1-yl)propyl]quinoline Chemical compound C=1C=C2C=C(OC(F)F)C(OC(F)F)=CC2=NC=1C(C(C)C)N1C=CN=N1 ACRSZAYEYQXIHV-UHFFFAOYSA-N 0.000 claims 2
- QZZDRPHAVDBLKT-UHFFFAOYSA-N 6,7-dichloro-2-[2-methyl-1-(triazol-1-yl)propyl]quinoline Chemical compound C=1C=C2C=C(Cl)C(Cl)=CC2=NC=1C(C(C)C)N1C=CN=N1 QZZDRPHAVDBLKT-UHFFFAOYSA-N 0.000 claims 2
- IQTCYQRIVUZIIR-UHFFFAOYSA-N 6,7-difluoro-2-[2-methyl-1-(triazol-1-yl)propyl]quinoline Chemical compound C=1C=C2C=C(F)C(F)=CC2=NC=1C(C(C)C)N1C=CN=N1 IQTCYQRIVUZIIR-UHFFFAOYSA-N 0.000 claims 2
- JSKXGPXVTXFGHZ-UHFFFAOYSA-N 6-(4-fluorophenyl)-2-[2-methyl-1-(triazol-1-yl)propyl]quinoline Chemical compound C1=CN=NN1C(C(C)C)C(N=C1C=C2)=CC=C1C=C2C1=CC=C(F)C=C1 JSKXGPXVTXFGHZ-UHFFFAOYSA-N 0.000 claims 2
- UWCZIWJOVNLPKR-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[2-methyl-1-(triazol-1-yl)propyl]quinoline Chemical compound C=1C=C2C=C(OC(F)F)C=CC2=NC=1C(C(C)C)N1C=CN=N1 UWCZIWJOVNLPKR-UHFFFAOYSA-N 0.000 claims 2
- PIXNGVPUUHYBQA-UHFFFAOYSA-N 6-[2-methyl-1-(triazol-1-yl)propyl]naphthalene-2-carbonitrile Chemical compound C=1C=C2C=C(C#N)C=CC2=CC=1C(C(C)C)N1C=CN=N1 PIXNGVPUUHYBQA-UHFFFAOYSA-N 0.000 claims 2
- OVXCEJFWQRLYNB-UHFFFAOYSA-N 6-methoxy-2-[2-methyl-1-(triazol-1-yl)propyl]quinoline Chemical compound C1=CC2=CC(OC)=CC=C2N=C1C(C(C)C)N1C=CN=N1 OVXCEJFWQRLYNB-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- QEZOREMRKLAITG-UHFFFAOYSA-N 1-[1-(6,7-dimethoxynaphthalen-2-yl)-2-methylpropyl]triazole Chemical compound C1=C2C=C(OC)C(OC)=CC2=CC=C1C(C(C)C)N1C=CN=N1 QEZOREMRKLAITG-UHFFFAOYSA-N 0.000 claims 1
- NFQKPZFNPDYSSC-UHFFFAOYSA-N 1-[1-[6,7-bis(2,2,2-trifluoroethoxy)naphthalen-2-yl]-2-methylpropyl]triazole Chemical compound C=1C=C2C=C(OCC(F)(F)F)C(OCC(F)(F)F)=CC2=CC=1C(C(C)C)N1C=CN=N1 NFQKPZFNPDYSSC-UHFFFAOYSA-N 0.000 claims 1
- CGFYQNFBXXHVRR-UHFFFAOYSA-N 2-[2-methyl-1-(triazol-1-yl)propyl]-6-(2,2,2-trifluoroethoxy)quinoline Chemical compound C=1C=C2C=C(OCC(F)(F)F)C=CC2=NC=1C(C(C)C)N1C=CN=N1 CGFYQNFBXXHVRR-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
- 208000008448 Congenital adrenal hyperplasia Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 206010020112 Hirsutism Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 201000004458 Myoma Diseases 0.000 claims 1
- 208000010195 Onychomycosis 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
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 210000004404 adrenal cortex Anatomy 0.000 claims 1
- 230000001919 adrenal effect Effects 0.000 claims 1
- 125000003277 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
- 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
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 208000030270 breast disease Diseases 0.000 claims 1
- 239000002327 cardiovascular agent Substances 0.000 claims 1
- 229940125692 cardiovascular agent Drugs 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 239000002254 cytotoxic agent Substances 0.000 claims 1
- 231100000599 cytotoxic agent Toxicity 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
- 235000019000 fluorine Nutrition 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 125000005843 halogen group Chemical group 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
- 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
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
- 208000006155 precocious puberty Diseases 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 201000004240 prostatic hypertrophy Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 206010052366 systemic mycosis Diseases 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 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
- 210000004291 uterus Anatomy 0.000 claims 1
- PBJIMYQQVULMKE-MMJNVBMASA-N C/C=C(\C=C/C1=[O]C2(CCCC2)C1[n]1nncc1)/C#N Chemical compound C/C=C(\C=C/C1=[O]C2(CCCC2)C1[n]1nncc1)/C#N PBJIMYQQVULMKE-MMJNVBMASA-N 0.000 description 1
- PRRSYFZERBDOEZ-UHFFFAOYSA-N Clc1ccc(C(c(cc2)ccc2Cl)[n]2nncc2)cc1 Chemical compound Clc1ccc(C(c(cc2)ccc2Cl)[n]2nncc2)cc1 PRRSYFZERBDOEZ-UHFFFAOYSA-N 0.000 description 1
- GAKWPZYLXDZXKP-UHFFFAOYSA-N Fc1ccc(C(c(cc2)ccc2F)[n]2nncc2)cc1 Chemical compound Fc1ccc(C(c(cc2)ccc2F)[n]2nncc2)cc1 GAKWPZYLXDZXKP-UHFFFAOYSA-N 0.000 description 1
- CJIUFDNHFZCBGI-UHFFFAOYSA-N N#Cc(cc1)cc2c1C([n]1nncc1)=CCC2 Chemical compound N#Cc(cc1)cc2c1C([n]1nncc1)=CCC2 CJIUFDNHFZCBGI-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42252810P | 2010-12-13 | 2010-12-13 | |
| US61/422,528 | 2010-12-13 | ||
| PCT/US2011/064658 WO2012082746A2 (en) | 2010-12-13 | 2011-12-13 | Metalloenzyme inhibitor compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014504287A JP2014504287A (ja) | 2014-02-20 |
| JP2014504287A5 true JP2014504287A5 (enExample) | 2015-02-05 |
| JP6071897B2 JP6071897B2 (ja) | 2017-02-01 |
Family
ID=46199977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013543412A Expired - Fee Related JP6071897B2 (ja) | 2010-12-13 | 2011-12-13 | 金属酵素阻害化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8669274B2 (enExample) |
| EP (1) | EP2651905B1 (enExample) |
| JP (1) | JP6071897B2 (enExample) |
| KR (1) | KR20130101576A (enExample) |
| CN (1) | CN103328452A (enExample) |
| AU (1) | AU2011343966B2 (enExample) |
| BR (1) | BR112013014484A2 (enExample) |
| CA (1) | CA2820718A1 (enExample) |
| EA (1) | EA201390876A1 (enExample) |
| WO (1) | WO2012082746A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2014209107B2 (en) | 2013-01-28 | 2018-04-12 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
| KR102934754B1 (ko) * | 2015-11-25 | 2026-03-04 | 이펙터 테라퓨틱스, 인크. | Eif4a-억제 화합물 및 이에 관련된 방법 |
| WO2018119440A1 (en) | 2016-12-22 | 2018-06-28 | Calithera Biosciences, Inc. | Compositions and methods for inhibiting arginase activity |
| 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 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4227004A (en) * | 1979-01-02 | 1980-10-07 | Ici Americas Inc. | Synthesis of substituted 1-aralkyl-1H-v-triazoles |
| US4921475A (en) | 1983-08-18 | 1990-05-01 | Drug Delivery Systems Inc. | Transdermal drug patch with microtubes |
| US5087240A (en) | 1983-08-18 | 1992-02-11 | Drug Delivery Systems Inc. | Transdermal drug patch with conductive fibers |
| 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 |
| EP0721943A4 (en) * | 1993-09-30 | 1996-09-04 | Yamanouchi Pharma Co Ltd | AZOL DERIVATIVES AND PHARMACEUTICAL PREPARATIONS |
| 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. |
| GB9418443D0 (en) * | 1994-09-13 | 1994-11-02 | Pfizer Ltd | Therapeutic agents |
| US5800807A (en) | 1997-01-29 | 1998-09-01 | Bausch & Lomb Incorporated | Ophthalmic compositions including glycerin and propylene glycol |
| US5994335A (en) * | 1997-10-17 | 1999-11-30 | The University Of Maryland, Baltimore | 17-azolyl steroids useful as androgen synthesis inhibitors |
| CA2460075A1 (en) * | 2001-09-12 | 2003-03-20 | Donn Gregory Wishka | Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases |
| US6770659B2 (en) * | 2002-08-26 | 2004-08-03 | Sk Corporation | Benzoyl piperidine compounds |
| 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 |
| GB2404613A (en) | 2003-07-14 | 2005-02-09 | David Jarman | A vegetation pruning device |
| EP1781635B1 (en) * | 2004-07-29 | 2012-06-13 | Merck Sharp & Dohme Corp. | Potassium channel inhibitors |
| US7183284B2 (en) * | 2004-12-29 | 2007-02-27 | Bristol-Myers Squibb Company | Aminium salts of 1,2,3-triazoles as prodrugs of drugs including antiviral agents |
| CL2007002231A1 (es) | 2006-08-02 | 2008-04-11 | Basf Ag | Uso de compuestos derivados de 5-(het) arilpirimidina para combatir hongos daninos; compuestos derivados de 5-(het) arilpirimidina; agente fungicida; y agente farmaceutico. |
| EP2234608A2 (en) * | 2007-12-11 | 2010-10-06 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties |
| CN102026988B (zh) | 2008-06-05 | 2013-07-03 | 爱思开生物制药株式会社 | 3-取代的丙胺化合物 |
| US8101642B2 (en) | 2008-06-05 | 2012-01-24 | Sk Biopharmaceuticals Co., Ltd. | 3-substituted propanamine compounds |
| US8546576B2 (en) | 2008-06-06 | 2013-10-01 | Sk Biopharmaceuticals Co., Ltd. | 3 or 4-substituted piperidine compounds |
-
2011
- 2011-12-13 AU AU2011343966A patent/AU2011343966B2/en not_active Ceased
- 2011-12-13 JP JP2013543412A patent/JP6071897B2/ja not_active Expired - Fee Related
- 2011-12-13 CA CA2820718A patent/CA2820718A1/en not_active Abandoned
- 2011-12-13 BR BR112013014484A patent/BR112013014484A2/pt not_active IP Right Cessation
- 2011-12-13 EA EA201390876A patent/EA201390876A1/ru unknown
- 2011-12-13 WO PCT/US2011/064658 patent/WO2012082746A2/en not_active Ceased
- 2011-12-13 CN CN201180065056XA patent/CN103328452A/zh active Pending
- 2011-12-13 EP EP11848545.7A patent/EP2651905B1/en not_active Not-in-force
- 2011-12-13 US US13/324,707 patent/US8669274B2/en not_active Expired - Fee Related
- 2011-12-13 KR KR1020137017838A patent/KR20130101576A/ko not_active Ceased
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