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 (https=) | 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 (https=) |
| EP (1) | EP2651905B1 (https=) |
| JP (1) | JP6071897B2 (https=) |
| KR (1) | KR20130101576A (https=) |
| CN (1) | CN103328452A (https=) |
| AU (1) | AU2011343966B2 (https=) |
| BR (1) | BR112013014484A2 (https=) |
| CA (1) | CA2820718A1 (https=) |
| EA (1) | EA201390876A1 (https=) |
| WO (1) | WO2012082746A2 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2014209107B2 (en) | 2013-01-28 | 2018-04-12 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
| DK3888658T3 (da) * | 2015-11-25 | 2024-03-18 | Effector Therapeutics Inc | Eif4-a-inhiberende forbindelser og fremgangsmåder relateret dertil |
| 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 |
| 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 |
| DK0431519T3 (da) | 1989-12-04 | 1994-07-04 | Searle & Co | System til transdermal indgivelse af albuterol |
| US5077033A (en) | 1990-08-07 | 1991-12-31 | Mediventures Inc. | Ophthalmic drug delivery with thermo-irreversible gels of polxoxyalkylene polymer and ionic polysaccharide |
| JP2594486B2 (ja) | 1991-01-15 | 1997-03-26 | アルコン ラボラトリーズ インコーポレイテッド | 局所的眼薬組成物 |
| 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 |
| ATE132381T1 (de) | 1992-01-29 | 1996-01-15 | Voelkl Franz Ski | Ballspielschläger, insbesondere tennisschläger |
| WO1995009157A1 (en) * | 1993-09-30 | 1995-04-06 | Yamanouchi Pharmaceutical Co., Ltd. | Azole derivative and pharmaceutical composition thereof |
| 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 |
| DE60218493D1 (de) * | 2001-09-12 | 2007-04-12 | Pharmacia & Upjohn Co Llc | Substituierte 7-aza-ä2.2.1übicycloheptane für die behandlung von krankheiten |
| US6770659B2 (en) * | 2002-08-26 | 2004-08-03 | Sk Corporation | Benzoyl piperidine compounds |
| MXPA06000401A (es) * | 2003-07-10 | 2006-03-17 | Osi Pharm Inc | Derivados de naftileno como inhibidores de citocromo p450. |
| GB2404613A (en) | 2003-07-14 | 2005-02-09 | David Jarman | A vegetation pruning device |
| CN1993347A (zh) * | 2004-07-29 | 2007-07-04 | 默克公司 | 钾通道抑制剂 |
| 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. |
| 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 |
| US8101642B2 (en) | 2008-06-05 | 2012-01-24 | Sk Biopharmaceuticals Co., Ltd. | 3-substituted propanamine compounds |
| JP5527668B2 (ja) | 2008-06-05 | 2014-06-18 | エスケー バイオファーマスティカルズ カンパニー リミテッド | ３−置換プロパンアミン化合物 |
| US8546576B2 (en) | 2008-06-06 | 2013-10-01 | Sk Biopharmaceuticals Co., Ltd. | 3 or 4-substituted piperidine compounds |
-
2011
- 2011-12-13 CN CN201180065056XA patent/CN103328452A/zh active Pending
- 2011-12-13 CA CA2820718A patent/CA2820718A1/en not_active Abandoned
- 2011-12-13 US US13/324,707 patent/US8669274B2/en not_active Expired - Fee Related
- 2011-12-13 JP JP2013543412A patent/JP6071897B2/ja not_active Expired - Fee Related
- 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 EP EP11848545.7A patent/EP2651905B1/en not_active Not-in-force
- 2011-12-13 KR KR1020137017838A patent/KR20130101576A/ko not_active Ceased
- 2011-12-13 AU AU2011343966A patent/AU2011343966B2/en not_active Ceased
- 2011-12-13 BR BR112013014484A patent/BR112013014484A2/pt not_active IP Right Cessation
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