JP2020534299A5 - - Google Patents
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- JP2020534299A5 JP2020534299A5 JP2020515978A JP2020515978A JP2020534299A5 JP 2020534299 A5 JP2020534299 A5 JP 2020534299A5 JP 2020515978 A JP2020515978 A JP 2020515978A JP 2020515978 A JP2020515978 A JP 2020515978A JP 2020534299 A5 JP2020534299 A5 JP 2020534299A5
- Authority
- JP
- Japan
- Prior art keywords
- approximately
- neuroprotective composition
- subject
- triterpene
- 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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- 239000000203 mixture Substances 0.000 claims description 63
- 230000000324 neuroprotective effect Effects 0.000 claims description 61
- 150000003648 triterpenes Chemical class 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 230000004797 therapeutic response Effects 0.000 claims description 18
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 16
- 229940096998 ursolic acid Drugs 0.000 claims description 16
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 claims description 16
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 claims description 14
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 claims description 14
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 claims description 14
- 229940100243 oleanolic acid Drugs 0.000 claims description 14
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 claims description 14
- 230000000926 neurological effect Effects 0.000 claims description 13
- QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 claims description 12
- CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 claims description 12
- DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 claims description 12
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 claims description 12
- PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 claims description 12
- MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 claims description 12
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 claims description 10
- 102100021257 Beta-secretase 1 Human genes 0.000 claims description 10
- 239000002552 dosage form Substances 0.000 claims description 10
- 229940002612 prodrug Drugs 0.000 claims description 10
- 239000000651 prodrug Substances 0.000 claims description 10
- 101710150192 Beta-secretase 1 Proteins 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 102000010909 Monoamine Oxidase Human genes 0.000 claims description 6
- 108010062431 Monoamine oxidase Proteins 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- -1 derivatives Substances 0.000 claims description 6
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 6
- 210000002569 neuron Anatomy 0.000 claims description 6
- 210000000225 synapse Anatomy 0.000 claims description 6
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- 102000006378 Catechol O-methyltransferase Human genes 0.000 claims description 4
- 108020002739 Catechol O-methyltransferase Proteins 0.000 claims description 4
- 229930194930 Triterpen Natural products 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 230000001773 anti-convulsant effect Effects 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 229960003965 antiepileptics Drugs 0.000 claims description 4
- 229940097217 cardiac glycoside Drugs 0.000 claims description 4
- 239000002368 cardiac glycoside Substances 0.000 claims description 4
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 4
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 4
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000955 oleanolic acid group Chemical group 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- 229930002534 steroid glycoside Natural products 0.000 claims description 4
- 150000008143 steroidal glycosides Chemical class 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 229960001685 tacrine Drugs 0.000 claims description 4
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003523 triterpene group Chemical group 0.000 claims description 4
- 230000003247 decreasing effect Effects 0.000 claims description 3
- XKFPYPQQHFEXRZ-UHFFFAOYSA-N 5-methyl-N'-(phenylmethyl)-3-isoxazolecarbohydrazide Chemical compound O1C(C)=CC(C(=O)NNCC=2C=CC=CC=2)=N1 XKFPYPQQHFEXRZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000037259 Amyloid Plaque Diseases 0.000 claims description 2
- 102000014303 Amyloid beta-Protein Precursor Human genes 0.000 claims description 2
- 108010079054 Amyloid beta-Protein Precursor Proteins 0.000 claims description 2
- 108010060159 Apolipoprotein E4 Proteins 0.000 claims description 2
- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 claims description 2
- WKDNQONLGXOZRG-HRNNMHKYSA-N CO[C@H]1CC[C@@]2(Cc3ccc(cc3[C@@]22N=C(C)C(N)=N2)-c2cncc(c2)C#CC)CC1 Chemical compound CO[C@H]1CC[C@@]2(Cc3ccc(cc3[C@@]22N=C(C)C(N)=N2)-c2cncc(c2)C#CC)CC1 WKDNQONLGXOZRG-HRNNMHKYSA-N 0.000 claims description 2
- 101710113789 Candidapepsin-2 Proteins 0.000 claims description 2
- 108091006146 Channels Proteins 0.000 claims description 2
- 208000003164 Diplopia Diseases 0.000 claims description 2
- 201000010374 Down Syndrome Diseases 0.000 claims description 2
- 206010013654 Drug abuse Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000034826 Genetic Predisposition to Disease Diseases 0.000 claims description 2
- 206010019196 Head injury Diseases 0.000 claims description 2
- 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 101710180316 Protease 2 Proteins 0.000 claims description 2
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 230000003941 amyloidogenesis Effects 0.000 claims description 2
- 230000003444 anaesthetic effect Effects 0.000 claims description 2
- 229960004046 apomorphine Drugs 0.000 claims description 2
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims description 2
- 229960000794 baclofen Drugs 0.000 claims description 2
- 239000000812 cholinergic antagonist Substances 0.000 claims description 2
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical class COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 208000002173 dizziness Diseases 0.000 claims description 2
- 229960003530 donepezil Drugs 0.000 claims description 2
- 229940052760 dopamine agonists Drugs 0.000 claims description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 2
- 229940108366 exelon Drugs 0.000 claims description 2
- 239000003527 fibrinolytic agent Substances 0.000 claims description 2
- 230000005021 gait Effects 0.000 claims description 2
- 229960003980 galantamine Drugs 0.000 claims description 2
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- WRYZEGZNBYOMLE-UHFFFAOYSA-N hydracarbazine Chemical compound NNC1=CC=C(C(N)=O)N=N1 WRYZEGZNBYOMLE-UHFFFAOYSA-N 0.000 claims description 2
- 229950002598 hydracarbazine Drugs 0.000 claims description 2
- 208000026762 inability to speak Diseases 0.000 claims description 2
- 229960002672 isocarboxazid Drugs 0.000 claims description 2
- 229960001848 lamotrigine Drugs 0.000 claims description 2
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 claims description 2
- 229960004502 levodopa Drugs 0.000 claims description 2
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 claims description 2
- 229960003907 linezolid Drugs 0.000 claims description 2
- 230000007774 longterm Effects 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 2
- 229940033872 namenda Drugs 0.000 claims description 2
- 231100000862 numbness Toxicity 0.000 claims description 2
- 229960004851 pergolide Drugs 0.000 claims description 2
- YEHCICAEULNIGD-MZMPZRCHSA-N pergolide Chemical compound C1=CC([C@H]2C[C@@H](CSC)CN([C@@H]2C2)CCC)=C3C2=CNC3=C1 YEHCICAEULNIGD-MZMPZRCHSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims description 2
- 229960000245 rasagiline Drugs 0.000 claims description 2
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 claims description 2
- 229940051845 razadyne Drugs 0.000 claims description 2
- 229940044551 receptor antagonist Drugs 0.000 claims description 2
- 239000002464 receptor antagonist Substances 0.000 claims description 2
- 230000003252 repetitive effect Effects 0.000 claims description 2
- 229960003946 selegiline Drugs 0.000 claims description 2
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 claims description 2
- 208000018316 severe headache Diseases 0.000 claims description 2
- 230000000391 smoking effect Effects 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229940125794 sodium channel blocker Drugs 0.000 claims description 2
- 239000003195 sodium channel blocking agent Substances 0.000 claims description 2
- 208000011117 substance-related disease Diseases 0.000 claims description 2
- 229960000103 thrombolytic agent Drugs 0.000 claims description 2
- 208000019553 vascular disease Diseases 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 230000004044 response Effects 0.000 claims 4
- 230000006269 (delayed) early viral mRNA transcription Effects 0.000 claims 1
- 230000007505 plaque formation Effects 0.000 claims 1
- 230000017854 proteolysis Effects 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762558631P | 2017-09-14 | 2017-09-14 | |
| US62/558,631 | 2017-09-14 | ||
| PCT/US2018/049358 WO2019055245A1 (en) | 2017-09-14 | 2018-10-02 | IMPROVED METHOD AND COMPOSITION FOR THE TREATMENT OF TRITERPENE SENSITIVE CONDITIONS, DISEASES OR DISORDERS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020534299A JP2020534299A (ja) | 2020-11-26 |
| JP2020534299A5 true JP2020534299A5 (OSRAM) | 2021-10-14 |
| JP7370966B2 JP7370966B2 (ja) | 2023-10-30 |
Family
ID=65630104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020515978A Active JP7370966B2 (ja) | 2017-09-14 | 2018-09-04 | 神経学的状態を治療するための方法および改善された神経保護組成物 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10722482B2 (OSRAM) |
| EP (1) | EP3681477A4 (OSRAM) |
| JP (1) | JP7370966B2 (OSRAM) |
| KR (1) | KR20200083969A (OSRAM) |
| CN (1) | CN111417384A (OSRAM) |
| AU (1) | AU2018334467B2 (OSRAM) |
| CA (1) | CA3075023A1 (OSRAM) |
| IL (1) | IL273161A (OSRAM) |
| MX (1) | MX2020002884A (OSRAM) |
| RU (1) | RU2758376C2 (OSRAM) |
| WO (2) | WO2019055245A1 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10702567B2 (en) | 2016-09-14 | 2020-07-07 | Phoenix Biotechnology, Inc. | Method and compositions for treating viral infection |
| US10729735B1 (en) | 2016-09-14 | 2020-08-04 | Phoenix Biotechnology, Inc. | Method and compostitions for treating coronavirus infection |
| US10596186B2 (en) | 2016-09-14 | 2020-03-24 | Phoenix Biotechnology, Inc. | Method and compositions for treating viral infections |
| AU2018334467B2 (en) * | 2017-09-14 | 2022-10-20 | Phoenix Biotechnology, Inc. | Method and improved neuroprotective composition for treating neurological conditions |
| US11331291B2 (en) * | 2017-09-14 | 2022-05-17 | Phoenix Biotechnology, Inc. | Method of and improved composition for treating triterpene-responsive conditions, diseases or disorders |
| US11806359B2 (en) | 2020-03-31 | 2023-11-07 | Phoenix Biotechnology, Inc. | Method and compositions for treating Coronavirus infection |
| WO2021202547A1 (en) * | 2020-04-01 | 2021-10-07 | Triterpenoid Therapeutics, Inc. | Methods and compositions for treating and preventing viral infection |
| CN111888367A (zh) * | 2020-07-31 | 2020-11-06 | 兰州大学 | 一种萜类化合物在制备增强蛋白酶体活性药物中的应用 |
| US12357641B2 (en) * | 2022-10-13 | 2025-07-15 | Hong Kong Baptist University | Identification of oleanolic acid and plant extract for glucose-6-phosphate dehydrogenase-related disorders including Bag3opathy |
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| US922078A (en) | 1909-03-01 | 1909-05-18 | Charles Burwell Benson | Tongue-depressor. |
| DK166650B1 (da) | 1991-03-15 | 1993-06-28 | Aarhus Oliefabrik As | Fedtbaser samt anvendelse af disse i kosmetiske og farmaceutiske emulsionsprodukter |
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| ES2308979T3 (es) | 1999-04-27 | 2008-12-16 | Forbes Medi-Tech Inc. | Procedimiento para la preparacion de una composicion de fitosteroles. |
| CN1129613C (zh) | 1999-12-24 | 2003-12-03 | 中国科学院上海药物研究所 | 夹竹桃花多糖及其制备方法和应用 |
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| EP1309605A1 (en) | 2000-08-18 | 2003-05-14 | The Board Of Trustees Of The University Of Illinois | Prodrugs of betulinic acid derivatives for the treatment of cancer and hiv |
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-
2018
- 2018-09-04 AU AU2018334467A patent/AU2018334467B2/en not_active Ceased
- 2018-09-04 JP JP2020515978A patent/JP7370966B2/ja active Active
- 2018-09-04 EP EP18855856.3A patent/EP3681477A4/en not_active Withdrawn
- 2018-09-04 MX MX2020002884A patent/MX2020002884A/es unknown
- 2018-09-04 CN CN201880062070.6A patent/CN111417384A/zh active Pending
- 2018-09-04 CA CA3075023A patent/CA3075023A1/en active Pending
- 2018-09-04 KR KR1020207007410A patent/KR20200083969A/ko not_active Abandoned
- 2018-09-04 RU RU2020113349A patent/RU2758376C2/ru active
- 2018-10-02 WO PCT/US2018/049358 patent/WO2019055245A1/en not_active Ceased
- 2018-11-08 WO PCT/US2018/059818 patent/WO2020050865A1/en not_active Ceased
- 2018-11-08 US US16/184,628 patent/US10722482B2/en not_active Expired - Fee Related
-
2020
- 2020-03-09 IL IL273161A patent/IL273161A/en unknown
- 2020-06-08 US US16/895,152 patent/US10973785B2/en not_active Expired - Fee Related
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