CH621803A5 - - Google Patents
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- Publication number
- CH621803A5 CH621803A5 CH1085574A CH1085574A CH621803A5 CH 621803 A5 CH621803 A5 CH 621803A5 CH 1085574 A CH1085574 A CH 1085574A CH 1085574 A CH1085574 A CH 1085574A CH 621803 A5 CH621803 A5 CH 621803A5
- Authority
- CH
- Switzerland
- Prior art keywords
- androstane
- process according
- formula
- pyridazinyl
- hydroxyl group
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 15
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- -1 steroid compounds Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 230000009466 transformation Effects 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 230000003177 cardiotonic effect Effects 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 229930182470 glycoside Natural products 0.000 claims description 3
- 150000002338 glycosides Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000005217 methyl ethers Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-furil Chemical class C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 3
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims 1
- 238000006359 acetalization reaction Methods 0.000 claims 1
- 150000001241 acetals Chemical class 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 7
- 235000017281 sodium acetate Nutrition 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- JGEMYUOFGVHXKV-OWOJBTEDSA-N fumaraldehyde Chemical compound O=C\C=C\C=O JGEMYUOFGVHXKV-OWOJBTEDSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- ODJLBQGVINUMMR-UHFFFAOYSA-N Strophanthidin Natural products CC12CCC(C3(CCC(O)CC3(O)CC3)C=O)C3C1(O)CCC2C1=CC(=O)OC1 ODJLBQGVINUMMR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001738 cardenolides Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- ODJLBQGVINUMMR-HZXDTFASSA-N strophanthidin Chemical compound C1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@@]5(O)CC4)C=O)CC[C@@]32C)=CC(=O)OC1 ODJLBQGVINUMMR-HZXDTFASSA-N 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1085574A CH621803A5 (OSRAM) | 1974-08-08 | 1974-08-08 | |
| GB31789/75A GB1484655A (en) | 1974-08-08 | 1975-07-29 | Cardiotonic steroids process for their preparation and therapeutical use |
| US05/600,485 US4000125A (en) | 1974-08-08 | 1975-07-30 | Novel cardiotonic steroids, process for their preparation and therapeutical use |
| DE19752534981 DE2534981A1 (de) | 1974-08-08 | 1975-08-05 | Kardiotonische steroidverbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| DK358875AA DK139101B (da) | 1974-08-08 | 1975-08-07 | Analogifremgangsmåde til fremstilling af 3beta,14beta-dihydroxy-17beta-(4-pyridazinyl)-5beta-androstan-forbindelser. |
| FR7524701A FR2281124A1 (fr) | 1974-08-08 | 1975-08-07 | Nouveaux steroides cardiotoniques, leur procede de preparation, et leur utilisation therapeutique |
| CA233,045A CA1049499A (en) | 1974-08-08 | 1975-08-07 | Cardiotonic steroids, process for their preparation and therapeutical use |
| AR259928A AR217617A1 (es) | 1974-08-08 | 1975-08-07 | Procedimiento para la preparacion de nuevos compuestos esteroides derivados de los 14-hidroxi-17 beta-(4-piridazinil)-5 beta,14 beta-androstanos,particularmenmente utiles como agentes cardiotonicos y sus derivados glucosidos |
| SE7508908A SE418401B (sv) | 1974-08-08 | 1975-08-07 | Sett att framstella kardiotona steroidforeningar innehallande en pyridazinring och glykosidderivat derav |
| JP50095475A JPS5141372A (OSRAM) | 1974-08-08 | 1975-08-07 | |
| ES440110A ES440110A1 (es) | 1974-08-08 | 1975-08-08 | Procedimiento para la obtencion de compuestos esteroides cardiotonicos. |
| BE159066A BE832271A (fr) | 1974-08-08 | 1975-08-08 | Nouveaux steroides cardiotoniques, leur procede de preparation et leur utilisation therapeutique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1085574A CH621803A5 (OSRAM) | 1974-08-08 | 1974-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621803A5 true CH621803A5 (OSRAM) | 1981-02-27 |
Family
ID=4367535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1085574A CH621803A5 (OSRAM) | 1974-08-08 | 1974-08-08 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4000125A (OSRAM) |
| JP (1) | JPS5141372A (OSRAM) |
| AR (1) | AR217617A1 (OSRAM) |
| BE (1) | BE832271A (OSRAM) |
| CA (1) | CA1049499A (OSRAM) |
| CH (1) | CH621803A5 (OSRAM) |
| DE (1) | DE2534981A1 (OSRAM) |
| DK (1) | DK139101B (OSRAM) |
| ES (1) | ES440110A1 (OSRAM) |
| FR (1) | FR2281124A1 (OSRAM) |
| GB (1) | GB1484655A (OSRAM) |
| SE (1) | SE418401B (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1144136B (it) * | 1980-03-05 | 1986-10-29 | Zenyaku Kogyo Kk | Glucosidi di condurango agenti antitumorali che li comprendono e procedimento per la loro preparazione |
| US5373095A (en) * | 1985-10-18 | 1994-12-13 | The Upjohn Company | Steroid compounds |
| IT1262931B (it) * | 1992-01-16 | 1996-07-22 | Zambon Spa | Composti steroidei 17(piridazin-n-ossido)-sostituiti attivi sul sistema cardiovascolare |
| DE4227616C2 (de) * | 1992-08-20 | 1995-04-13 | Sigma Tau Ind Farmaceuti | 17-(3-Furyl)-und 17-(4-Pyridazinyl)-5beta, 14beta-androstanderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammemsetzungen |
| US20100047338A1 (en) | 2008-03-14 | 2010-02-25 | Angela Brodie | Novel C-17-Heteroaryl Steroidal CYP17 Inhibitors/Antiandrogens, In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity |
| EA019560B1 (ru) * | 2005-03-02 | 2014-04-30 | Юнивесити Оф Мэриленд, Балтимор | Способ лечения простаты (варианты) |
| WO2009114658A2 (en) * | 2008-03-12 | 2009-09-17 | University Of Maryland, Baltimore | Androgen receptor inactivation contributes to antitumor efficacy of cyp17 inhibitors in prostate cancer |
| GB2470700B (en) | 2008-03-25 | 2012-08-08 | Univ Maryland | C-17 heteroaryl steroidal CYP17 inhibitors |
| US8785423B2 (en) * | 2008-04-14 | 2014-07-22 | University Of Maryland, Baltimore | Compositions and methods of inducing endoplasmic reticulum stress response for the treatment of cell proliferative diseases |
| ES2552087T3 (es) | 2009-02-05 | 2015-11-25 | Tokai Pharmaceuticals, Inc. | Nuevos profármacos de inhibidores de CYP17 esteroidales/antiandrógenos |
| GB2479693B (en) | 2009-02-05 | 2014-04-09 | Tokai Pharmaceuticals Inc | Steroidal CYP17 inhibitors and their use in the treatment of cancer and prostate hyperplasia |
| EP2461814A4 (en) | 2009-08-07 | 2012-12-05 | Tokai Pharmaceuticals Inc | PROSTATE CANCER TREATMENT |
| US9884067B2 (en) | 2013-03-14 | 2018-02-06 | University Of Maryland, Baltimore | Androgen receptor down-regulating agents and uses thereof |
| US9808472B2 (en) | 2013-08-12 | 2017-11-07 | Tokai Pharmaceuticals, Inc. | Biomarkers for treatment of neoplastic disorders using androgen-targeted therapies |
| EP3313858B1 (en) * | 2015-06-29 | 2019-09-25 | Universiteit Gent | Methods for the site-selective coupling of a first agent to a second agent |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3838163A (en) * | 1968-11-22 | 1974-09-24 | Hoffmann La Roche | Substituted isoxazole derivatives as steroid intermediates |
-
1974
- 1974-08-08 CH CH1085574A patent/CH621803A5/it not_active IP Right Cessation
-
1975
- 1975-07-29 GB GB31789/75A patent/GB1484655A/en not_active Expired
- 1975-07-30 US US05/600,485 patent/US4000125A/en not_active Expired - Lifetime
- 1975-08-05 DE DE19752534981 patent/DE2534981A1/de not_active Ceased
- 1975-08-07 DK DK358875AA patent/DK139101B/da unknown
- 1975-08-07 FR FR7524701A patent/FR2281124A1/fr active Granted
- 1975-08-07 AR AR259928A patent/AR217617A1/es active
- 1975-08-07 SE SE7508908A patent/SE418401B/xx unknown
- 1975-08-07 CA CA233,045A patent/CA1049499A/en not_active Expired
- 1975-08-07 JP JP50095475A patent/JPS5141372A/ja active Pending
- 1975-08-08 ES ES440110A patent/ES440110A1/es not_active Expired
- 1975-08-08 BE BE159066A patent/BE832271A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK139101C (OSRAM) | 1979-05-21 |
| DE2534981A1 (de) | 1976-02-19 |
| ES440110A1 (es) | 1977-02-16 |
| DK139101B (da) | 1978-12-18 |
| CA1049499A (en) | 1979-02-27 |
| GB1484655A (en) | 1977-09-01 |
| SE418401B (sv) | 1981-05-25 |
| AR217617A1 (es) | 1980-04-15 |
| SE7508908L (sv) | 1976-02-09 |
| BE832271A (fr) | 1975-12-01 |
| DK358875A (OSRAM) | 1976-02-09 |
| FR2281124A1 (fr) | 1976-03-05 |
| JPS5141372A (OSRAM) | 1976-04-07 |
| FR2281124B1 (OSRAM) | 1980-05-16 |
| US4000125A (en) | 1976-12-28 |
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