JP2007500705A5 - - Google Patents
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- Publication number
- JP2007500705A5 JP2007500705A5 JP2006522021A JP2006522021A JP2007500705A5 JP 2007500705 A5 JP2007500705 A5 JP 2007500705A5 JP 2006522021 A JP2006522021 A JP 2006522021A JP 2006522021 A JP2006522021 A JP 2006522021A JP 2007500705 A5 JP2007500705 A5 JP 2007500705A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- hydroxyphenyl
- tetramethylcyclohexylidene
- acid
- 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
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- 150000001875 compounds Chemical class 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 206010003693 Atrophic vulvovaginitis Diseases 0.000 claims 7
- 230000002265 prevention Effects 0.000 claims 7
- 201000009273 Endometriosis Diseases 0.000 claims 6
- 210000000988 bone and bone Anatomy 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 6
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 5
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- -1 4-hydroxy-2,3-dimethylphenyl Chemical group 0.000 claims 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 208000004746 Atrophic Vaginitis Diseases 0.000 claims 4
- 206010006187 Breast cancer Diseases 0.000 claims 4
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- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
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- 229910052500 inorganic mineral Inorganic materials 0.000 claims 4
- 238000012423 maintenance Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 239000011707 mineral Substances 0.000 claims 4
- 201000010808 postmenopausal atrophic vaginitis Diseases 0.000 claims 4
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- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
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- 229910052739 hydrogen Inorganic materials 0.000 claims 3
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- 150000003839 salts Chemical class 0.000 claims 3
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- 210000003433 aortic smooth muscle cell Anatomy 0.000 claims 2
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- 210000004556 brain Anatomy 0.000 claims 2
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- 201000011510 cancer Diseases 0.000 claims 2
- 230000000747 cardiac effect Effects 0.000 claims 2
- 230000004663 cell proliferation Effects 0.000 claims 2
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- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
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- 239000003814 drug Substances 0.000 claims 2
- 206010013990 dysuria Diseases 0.000 claims 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 2
- 210000004696 endometrium Anatomy 0.000 claims 2
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- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
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- 210000003734 kidney Anatomy 0.000 claims 2
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- 208000027202 mammary Paget disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000009245 menopause Effects 0.000 claims 2
- 230000003340 mental effect Effects 0.000 claims 2
- 230000027939 micturition Effects 0.000 claims 2
- 201000000585 muscular atrophy Diseases 0.000 claims 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- 210000004165 myocardium Anatomy 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
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- 210000001672 ovary Anatomy 0.000 claims 2
- 210000000496 pancreas Anatomy 0.000 claims 2
- 201000001245 periodontitis Diseases 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 201000011461 pre-eclampsia Diseases 0.000 claims 2
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims 2
- 230000001107 psychogenic effect Effects 0.000 claims 2
- 238000011084 recovery Methods 0.000 claims 2
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- 231100000872 sexual dysfunction Toxicity 0.000 claims 2
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- 206010043554 thrombocytopenia Diseases 0.000 claims 2
- 201000008827 tuberculosis Diseases 0.000 claims 2
- 210000004881 tumor cell Anatomy 0.000 claims 2
- 230000005740 tumor formation Effects 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 210000003932 urinary bladder Anatomy 0.000 claims 2
- 208000019206 urinary tract infection Diseases 0.000 claims 2
- 210000004291 uterus Anatomy 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- 201000001862 viral hepatitis Diseases 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- IIGBAYDKIWBPCU-AIHHMALZSA-N (2s)-1-[(e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)\C=C\C1=CC=C(C(C=2C=CC(O)=CC=2)=C2CCCCCC2)C=C1 IIGBAYDKIWBPCU-AIHHMALZSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- NDEYJKKJWBKIIR-CAOOACKPSA-N (e)-3-[3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(=CC=1)C=1C=C(\C=C\C(O)=O)C=CC=1)C1=CC=C(O)C=C1 NDEYJKKJWBKIIR-CAOOACKPSA-N 0.000 claims 1
- PDQBWIBKUHIICJ-NTUHNPAUSA-N (e)-3-[3-chloro-4-[cyclohexylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound ClC1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCC1 PDQBWIBKUHIICJ-NTUHNPAUSA-N 0.000 claims 1
- MQANJDKHDUDLHH-KPKJPENVSA-N (e)-3-[4-[(3-chloro-4-hydroxyphenyl)-(2,2,6,6-tetramethyloxan-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)OC(C)(C)CC1=C(C=1C=C(Cl)C(O)=CC=1)C1=CC=C(\C=C\C(O)=O)C=C1 MQANJDKHDUDLHH-KPKJPENVSA-N 0.000 claims 1
- IEEOYDJCAZMNFY-KPKJPENVSA-N (e)-3-[4-[(3-chloro-4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=C(Cl)C(O)=CC=1)C1=CC=C(\C=C\C(O)=O)C=C1 IEEOYDJCAZMNFY-KPKJPENVSA-N 0.000 claims 1
- IFKHGIYQTGYJSS-NTEUORMPSA-N (e)-3-[4-[(3-chloro-4-hydroxyphenyl)-cycloheptylidenemethyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(Cl)C(O)=CC=1)=C1CCCCCC1 IFKHGIYQTGYJSS-NTEUORMPSA-N 0.000 claims 1
- XLKZMOCPFOKRCN-MDWZMJQESA-N (e)-3-[4-[(3-chloro-4-hydroxyphenyl)-cyclohexylidenemethyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(Cl)C(O)=CC=1)=C1CCCCC1 XLKZMOCPFOKRCN-MDWZMJQESA-N 0.000 claims 1
- MRIRQIZLHFUDJT-KPKJPENVSA-N (e)-3-[4-[(3-fluoro-4-hydroxyphenyl)-(2,2,6,6-tetramethyloxan-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)OC(C)(C)CC1=C(C=1C=C(F)C(O)=CC=1)C1=CC=C(\C=C\C(O)=O)C=C1 MRIRQIZLHFUDJT-KPKJPENVSA-N 0.000 claims 1
- OMGMXYACDPFCEG-KPKJPENVSA-N (e)-3-[4-[(3-fluoro-4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=C(F)C(O)=CC=1)C1=CC=C(\C=C\C(O)=O)C=C1 OMGMXYACDPFCEG-KPKJPENVSA-N 0.000 claims 1
- OLJWDJBIESYNEY-LFYBBSHMSA-N (e)-3-[4-[(4,4-dimethylcyclohexylidene)-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1CC(C)(C)CCC1=C(C=1C=CC(\C=C\C(O)=O)=CC=1)C1=CC=C(O)C=C1 OLJWDJBIESYNEY-LFYBBSHMSA-N 0.000 claims 1
- LNBGFCKFUBABPV-VGOFMYFVSA-N (e)-3-[4-[(4-hydroxyphenyl)-(2,2,6,6-tetramethyloxan-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)OC(C)(C)CC1=C(C=1C=CC(\C=C\C(O)=O)=CC=1)C1=CC=C(O)C=C1 LNBGFCKFUBABPV-VGOFMYFVSA-N 0.000 claims 1
- NNFCEKYJMMYGOD-VGOFMYFVSA-N (e)-3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]prop-2-enamide Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(\C=C\C(N)=O)=CC=1)C1=CC=C(O)C=C1 NNFCEKYJMMYGOD-VGOFMYFVSA-N 0.000 claims 1
- LBVZZPZACRTCIB-VGOFMYFVSA-N (e)-3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(\C=C\C(O)=O)=CC=1)C1=CC=C(O)C=C1 LBVZZPZACRTCIB-VGOFMYFVSA-N 0.000 claims 1
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- NQIFKFNBTBROPX-XCVCLJGOSA-N (e)-3-[4-[(4-hydroxyphenyl)-(oxan-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCOCC1 NQIFKFNBTBROPX-XCVCLJGOSA-N 0.000 claims 1
- OLUZJHMLWRCIRT-XCVCLJGOSA-N (e)-3-[4-[(4-hydroxyphenyl)-(thian-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCSCC1 OLUZJHMLWRCIRT-XCVCLJGOSA-N 0.000 claims 1
- KNLYVVNUKJDQLW-NTEUORMPSA-N (e)-3-[4-[cycloheptylidene-(3-fluoro-4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(F)C(O)=CC=1)=C1CCCCCC1 KNLYVVNUKJDQLW-NTEUORMPSA-N 0.000 claims 1
- RACJIGDHWPWSOJ-OUKQBFOZSA-N (e)-3-[4-[cycloheptylidene-(3-hydroxyphenyl)methyl]-2-fluorophenyl]prop-2-enoic acid Chemical compound C1=C(F)C(/C=C/C(=O)O)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCCCCC1 RACJIGDHWPWSOJ-OUKQBFOZSA-N 0.000 claims 1
- STGYOKWDZVFRNJ-NTCAYCPXSA-N (e)-3-[4-[cycloheptylidene-(3-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(O)C=CC=1)=C1CCCCCC1 STGYOKWDZVFRNJ-NTCAYCPXSA-N 0.000 claims 1
- SGYCOKAIMUWWHK-SDNWHVSQSA-N (e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]-2-fluorophenyl]prop-2-enoic acid Chemical compound C1=C(F)C(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 SGYCOKAIMUWWHK-SDNWHVSQSA-N 0.000 claims 1
- YEZMYWLJHQMEKH-CXUHLZMHSA-N (e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enamide Chemical compound C1=CC(/C=C/C(=O)N)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 YEZMYWLJHQMEKH-CXUHLZMHSA-N 0.000 claims 1
- FIXMRJCBRFHJKY-CXUHLZMHSA-N (e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 FIXMRJCBRFHJKY-CXUHLZMHSA-N 0.000 claims 1
- VUFJYXGYPUYTEQ-MDWZMJQESA-N (e)-3-[4-[cyclohexylidene-(2,3-difluoro-4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C(=C(F)C(O)=CC=1)F)=C1CCCCC1 VUFJYXGYPUYTEQ-MDWZMJQESA-N 0.000 claims 1
- HLONBPXQNZKCTM-MDWZMJQESA-N (e)-3-[4-[cyclohexylidene-(2-fluoro-4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C(=CC(O)=CC=1)F)=C1CCCCC1 HLONBPXQNZKCTM-MDWZMJQESA-N 0.000 claims 1
- MUSXRSKAGXTKQI-MDWZMJQESA-N (e)-3-[4-[cyclohexylidene-(3-fluoro-4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(F)C(O)=CC=1)=C1CCCCC1 MUSXRSKAGXTKQI-MDWZMJQESA-N 0.000 claims 1
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- GOPACCJWLSLIKG-OVCLIPMQSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCC1 GOPACCJWLSLIKG-OVCLIPMQSA-N 0.000 claims 1
- VMKODCXRLKSFFR-ISLYRVAYSA-N (e)-3-[4-[cyclooctylidene-(4-hydroxyphenyl)methyl]phenyl]-2-methylprop-2-enoic acid Chemical compound C1=CC(\C=C(/C)C(O)=O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCCC1 VMKODCXRLKSFFR-ISLYRVAYSA-N 0.000 claims 1
- KCKMNQWYQVMVAR-LICLKQGHSA-N (e)-3-[4-[cyclooctylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCCC1 KCKMNQWYQVMVAR-LICLKQGHSA-N 0.000 claims 1
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- 125000004429 atom Chemical group 0.000 claims 1
- 230000037444 atrophy Effects 0.000 claims 1
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- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims 1
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- XQJWAVQFRPTEQX-UHFFFAOYSA-N n-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]benzenesulfonamide Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(NS(=O)(=O)C=2C=CC=CC=2)=CC=1)C1=CC=C(O)C=C1 XQJWAVQFRPTEQX-UHFFFAOYSA-N 0.000 claims 1
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- PFLBJGZHJKDSIT-UHFFFAOYSA-N n-[4-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=C(C(=C2CC(C)(C)CC(C)(C)C2)C=2C=CC(O)=CC=2)C=C1 PFLBJGZHJKDSIT-UHFFFAOYSA-N 0.000 claims 1
- DDYXJHBDEXURAL-UHFFFAOYSA-N n-[4-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]phenyl]methanesulfonamide Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(=CC=1)C=1C=CC(NS(C)(=O)=O)=CC=1)C1=CC=C(O)C=C1 DDYXJHBDEXURAL-UHFFFAOYSA-N 0.000 claims 1
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- 125000004076 pyridyl group Chemical group 0.000 claims 1
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- 230000000638 stimulation Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
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| PCT/US2004/024308 WO2005012220A2 (en) | 2003-07-28 | 2004-07-27 | Cycloalkylidene compounds as modulators of estrogen receptor |
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Families Citing this family (18)
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| JP2008545699A (ja) * | 2005-05-25 | 2008-12-18 | スミスクライン ビーチャム コーポレーション | 選択的エストロゲン受容体モジュレーターとしてのシクロアルキリデン化合物 |
| US20060281788A1 (en) | 2005-06-10 | 2006-12-14 | Baumann Christian A | Synergistic modulation of flt3 kinase using a flt3 inhibitor and a farnesyl transferase inhibitor |
| WO2007062190A2 (en) * | 2005-11-22 | 2007-05-31 | Smithkline Beecham Corporation | Chemical compounds |
| PL2021335T3 (pl) | 2006-04-20 | 2011-10-31 | Janssen Pharmaceutica Nv | Związki heterocykliczne jako inhibitory kinazy C-FMS |
| US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| WO2007124319A1 (en) | 2006-04-20 | 2007-11-01 | Janssen Pharmaceutica N.V. | Inhibitors of c-fms kinase |
| WO2008030771A1 (en) * | 2006-09-08 | 2008-03-13 | Smithkline Beecham Corporation | Cyclic alkylidene compounds as selective estrogen receptor modulators |
| JO3240B1 (ar) | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
| CN102786394B (zh) * | 2012-07-30 | 2017-03-01 | 中国医学科学院医药生物技术研究所 | 取代双芳基亚甲基环烷基衍生物及其制备方法和应用 |
| ES2658773T3 (es) | 2012-08-07 | 2018-03-12 | Janssen Pharmaceutica N.V. | Procedimiento de sulfonilación usando fluoruro de nonafluorobutanosulfonilo |
| CN104870454B (zh) | 2012-08-07 | 2020-03-03 | 詹森药业有限公司 | 用于制备杂环酯衍生物的方法 |
| RU2525397C2 (ru) * | 2012-09-10 | 2014-08-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" | 1-(4-этилфенил)-2-[3-(4-этилфенил)-2-(1н)-хиноксалинилиден]-1-этанон, обладающий анальгетической активностью |
| UY35590A (es) * | 2013-05-28 | 2014-11-28 | Astrazeneca Ab | Nuevos compuestos para el tratamiento del cáncer |
| WO2015026990A2 (en) | 2013-08-20 | 2015-02-26 | University Of Washington Through Its Center For Commercialization | Novel and specific inhibitors of cytochrome p450 26 retinoic acid hydrolase |
| CN107849072B (zh) | 2015-06-12 | 2020-12-15 | 西蒙弗雷泽大学 | 酰胺连接的ep4激动剂-二膦酸盐化合物及其用途 |
| CN115916170A (zh) * | 2020-04-17 | 2023-04-04 | 埃萨制药股份有限公司 | 固体形式的n-末端结构域雄激素受体抑制剂及其用途 |
| EP4410800A4 (en) * | 2021-10-01 | 2025-08-27 | Univ Fukui | PROCESS FOR PRODUCING VINYLPHOSPHONIC ACID MONOESTER |
| CN121443600A (zh) * | 2023-05-26 | 2026-01-30 | 北京盛诺基医药科技股份有限公司 | 一种靶向雌激素受体的protac化合物及其制备方法和用途 |
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| GB971908A (en) * | 1960-11-22 | 1964-10-07 | Ferrosan Ab | Dihydroxybenzhydrylidene cycloalkanes and derivatives thereof |
| US3760007A (en) | 1970-06-11 | 1973-09-18 | Schering Corp | Bicyclic benzhydrylidene derivatives |
| US3936493A (en) | 1973-04-17 | 1976-02-03 | Ortho Pharmaceutical Corporation | Diarylmethylenes |
| EP0273647B1 (en) | 1986-12-27 | 1992-03-11 | Takeda Chemical Industries, Ltd. | Coumaran derivatives, their production and use |
| SU1680693A1 (ru) * | 1987-03-25 | 1991-09-30 | Институт Органического Синтеза Ан Латвсср | Этил-3-(2,2-диметил-2-этилгидразиний)пропионат иодистый, про вл ющий антиаритмическую активность |
| DE3731913A1 (de) | 1987-09-23 | 1989-04-06 | Hoechst Ag | Pharmazeutische praeparate enthaltend ein 7-diphenylmethylenbicycloheptan- oder 7-diphenylmethylenbicyclohepten-derivat, die verwendung dieser verbindungen als arzneimittel sowie neue 7-diphenylmethylenbicycloheptane und 7-diphenylmethylenbicloheptene und verfahren zu ihrer herstellung |
| JP2876060B2 (ja) | 1989-04-03 | 1999-03-31 | 株式会社リコー | 電子写真感光体 |
| US5132190A (en) | 1989-04-10 | 1992-07-21 | Mitsui Toatsu Chemicals Incorporated | Hydrozones and electrophotographic photoreceptors comprising them |
| JPH02285356A (ja) | 1989-04-26 | 1990-11-22 | Kao Corp | 電子写真感光体 |
| JPH0315853A (ja) | 1989-06-14 | 1991-01-24 | Kao Corp | 電子写真感光体 |
| JPH03158852A (ja) | 1989-11-17 | 1991-07-08 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法及び定着能を有した組成物 |
| KR970005927B1 (ko) | 1990-10-10 | 1997-04-22 | 쉐링 코포레이션 | 디아릴메틸피페리딘 또는 피페라진의 피리딘 및 피리딘 n-옥사이드 유도체, 이를 함유하는 약제학적 조성물 및 이의 제조방법 |
| EP0589039A1 (en) | 1991-04-30 | 1994-03-30 | Asahi Kasei Kogyo Kabushiki Kaisha | Triphenylethylene derivative and pharmaceutical preparation containing the same |
| JPH0651546A (ja) | 1991-07-19 | 1994-02-25 | Ricoh Co Ltd | 電子写真用感光体 |
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| ZA933847B (en) * | 1992-06-02 | 1993-12-28 | Univ Australian | Anthelmintic and/or nematocidal compounds |
| US5306752A (en) | 1992-10-09 | 1994-04-26 | Loctite Corporation | Cyanoacrylate adhesives utilizing quinoid compound polymer stabilizer |
| WO1994015901A1 (en) | 1993-01-11 | 1994-07-21 | Ligand Pharmaceuticals Inc. | Compounds having selectivity for retinoid x receptors |
| JPH06332206A (ja) | 1993-05-26 | 1994-12-02 | Konica Corp | 電子写真感光体及び電子写真法 |
| DE19526146A1 (de) | 1995-07-07 | 1997-01-09 | Schering Ag | Triphenylethylene, Verfahren zu deren Herstellung, diese Triphenylethylene enthaltene pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
| LV11727B (en) * | 1995-08-21 | 1997-08-20 | Kalvins Ivars | Pharmaceutical composition |
| KR100263137B1 (ko) | 1995-09-08 | 2000-08-01 | 오테스코그 페르 | 오판 수용체 |
| FR2751964B1 (fr) | 1996-08-01 | 1998-10-30 | Union Pharma Scient Appl | Nouveaux derives diarylmethylene carbocycliques, leurs procedes de preparation, et leurs utilisations en therapeutique |
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| EP1000925A4 (en) | 1997-06-17 | 2001-08-08 | Sumitomo Chemical Co | TRIPHENYLMETHANE DERIVATIVES AND THEIR USE |
| DE69840126D1 (de) * | 1997-08-15 | 2008-11-27 | Univ Duke | Verfahren zur prophylaxis oder behandlung von östrogen-abhängigen krankheiten |
| TW593256B (en) | 1999-11-16 | 2004-06-21 | Hormos Medical Oy Ltd | Triphenylalkene derivatives and their use as selective estrogen receptor modulators |
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| PL374215A1 (en) | 2001-08-11 | 2005-10-03 | Bristol-Myers Squibb Pharma Company | Selective estrogen receptor modulators |
| JP2008545699A (ja) * | 2005-05-25 | 2008-12-18 | スミスクライン ビーチャム コーポレーション | 選択的エストロゲン受容体モジュレーターとしてのシクロアルキリデン化合物 |
-
2004
- 2004-07-27 EP EP04779374A patent/EP1667955A2/en not_active Withdrawn
- 2004-07-27 US US10/565,296 patent/US7560589B2/en not_active Expired - Fee Related
- 2004-07-27 WO PCT/US2004/024308 patent/WO2005012220A2/en not_active Ceased
- 2004-07-27 JP JP2006522021A patent/JP5013593B2/ja not_active Expired - Fee Related
- 2004-07-27 KR KR1020067001919A patent/KR20060066070A/ko not_active Ceased
- 2004-07-27 NZ NZ545032A patent/NZ545032A/en unknown
- 2004-07-27 MX MXPA06001094A patent/MXPA06001094A/es active IP Right Grant
- 2004-07-27 RU RU2006101632/04A patent/RU2345981C2/ru not_active IP Right Cessation
- 2004-07-27 CA CA2533812A patent/CA2533812C/en not_active Expired - Fee Related
- 2004-07-27 CN CNA2004800279546A patent/CN1856461A/zh active Pending
- 2004-07-27 AU AU2004261627A patent/AU2004261627C1/en not_active Ceased
- 2004-07-27 BR BRPI0413013-8A patent/BRPI0413013A/pt not_active IP Right Cessation
-
2006
- 2006-01-17 IL IL173192A patent/IL173192A0/en unknown
- 2006-01-25 NO NO20060403A patent/NO20060403L/no not_active Application Discontinuation
- 2006-01-27 ZA ZA200600819A patent/ZA200600819B/en unknown
- 2006-02-27 MA MA28844A patent/MA28015A1/fr unknown
-
2007
- 2007-05-14 US US11/748,096 patent/US7569601B2/en not_active Expired - Fee Related
-
2009
- 2009-06-08 US US12/480,097 patent/US7799828B2/en not_active Expired - Fee Related
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