JP2003508543A - 抗脈管形成活性を有する新規なベツリン酸誘導体、該誘導体を調整する方法、および腫瘍に関連する脈管形成を処置するためのそれらの使用 - Google Patents
抗脈管形成活性を有する新規なベツリン酸誘導体、該誘導体を調整する方法、および腫瘍に関連する脈管形成を処置するためのそれらの使用Info
- Publication number
- JP2003508543A JP2003508543A JP2001522252A JP2001522252A JP2003508543A JP 2003508543 A JP2003508543 A JP 2003508543A JP 2001522252 A JP2001522252 A JP 2001522252A JP 2001522252 A JP2001522252 A JP 2001522252A JP 2003508543 A JP2003508543 A JP 2003508543A
- Authority
- JP
- Japan
- Prior art keywords
- derivative
- betulinic acid
- och
- acid derivative
- chcl
- 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.)
- Pending
Links
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical class 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 title claims abstract description 118
- 238000000034 method Methods 0.000 title claims abstract description 73
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 15
- 230000033115 angiogenesis Effects 0.000 title claims abstract description 12
- 230000001772 anti-angiogenic effect Effects 0.000 title abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 85
- 229910052794 bromium Inorganic materials 0.000 claims description 84
- 229910052731 fluorine Inorganic materials 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 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 58
- 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 56
- 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 56
- 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 56
- 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 56
- 229910052740 iodine Inorganic materials 0.000 claims description 54
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 32
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- -1 OC2HFive Chemical group 0.000 claims description 21
- 210000002889 endothelial cell Anatomy 0.000 claims description 21
- 239000003960 organic solvent Substances 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 15
- 230000001476 alcoholic effect Effects 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- SLJTWDNVZKIDAU-SVAFSPIFSA-N Betulonic acid Chemical class C1CC(=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 SLJTWDNVZKIDAU-SVAFSPIFSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229960000583 acetic acid Drugs 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- BKTRGHKZQSHBHT-UHFFFAOYSA-N 3-Oxobetulinic acid Natural products CC(=C)C1CCC2(CC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12)C(=O)O BKTRGHKZQSHBHT-UHFFFAOYSA-N 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000007943 implant Substances 0.000 claims description 3
- 239000007937 lozenge Substances 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 3
- 229940067157 phenylhydrazine Drugs 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000006188 syrup Substances 0.000 claims description 3
- 235000020357 syrup Nutrition 0.000 claims description 3
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- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003935 benzaldehydes Chemical class 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims description 2
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- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 claims description 2
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- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
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- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 2
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
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- FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 description 1
- MVIRREHRVZLANQ-UHFFFAOYSA-N betulin Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C2CC=C4C5C(CCC5(CO)CCC34C)C(=C)C)C1(C)C MVIRREHRVZLANQ-UHFFFAOYSA-N 0.000 description 1
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- 239000003937 drug carrier Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 238000007910 systemic administration Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN1999/000043 WO2001018029A1 (en) | 1999-09-09 | 1999-09-09 | Novel betulinic acid derivatives having antiangiogenic activity, processes for producing such derivatives and their use for treating tumor associated angiogenesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003508543A true JP2003508543A (ja) | 2003-03-04 |
| JP2003508543A5 JP2003508543A5 (https=) | 2006-10-19 |
Family
ID=11076668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001522252A Pending JP2003508543A (ja) | 1999-09-09 | 1999-09-09 | 抗脈管形成活性を有する新規なベツリン酸誘導体、該誘導体を調整する方法、および腫瘍に関連する脈管形成を処置するためのそれらの使用 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1218402B1 (https=) |
| JP (1) | JP2003508543A (https=) |
| KR (1) | KR100618100B1 (https=) |
| CN (1) | CN1152046C (https=) |
| AT (1) | ATE267837T1 (https=) |
| AU (1) | AU780148B2 (https=) |
| BR (1) | BR9917495A (https=) |
| CA (1) | CA2384433C (https=) |
| DE (1) | DE69917684T2 (https=) |
| ES (1) | ES2224735T3 (https=) |
| WO (1) | WO2001018029A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020534358A (ja) * | 2017-09-18 | 2020-11-26 | 上海 インスティテュート オブ マテリア メディカ、チャイニーズ アカデミー オブ サイエンシーズＳｈａｎｇｈａｉ Ｉｎｓｔｉｔｕｔｅ Ｏｆ Ｍａｔｅｒｉａ Ｍｅｄｉｃａ， Ｃｈｉｎｅｓｅ Ａｃａｄｅｍｙ Ｏｆ Ｓｃｉｅｎｃｅｓ | ペンタシクロトリテルペン系化合物ならびにその製造方法、薬物組成物および使用 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4722031B2 (ja) | 2003-02-11 | 2011-07-13 | ノベリックス・ファーマシューティカルズ・インコーポレイテッド | 腫瘍増殖を阻害するための医薬 |
| RU2276980C1 (ru) * | 2005-03-01 | 2006-05-27 | Институт химии и химической технологии СО РАН (ИХХТ СО РАН) | Капилляроукрепляющее средство |
| EP1869063A2 (en) * | 2005-03-29 | 2007-12-26 | Regents Of The University Of Minnesota | Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid |
| GB0604535D0 (en) | 2006-03-07 | 2006-04-12 | Sndv Sprl | Betulonic acid derivatives |
| CZ2008528A3 (cs) * | 2008-09-01 | 2009-11-18 | Univerzita Karlova v Praze, Prírodovedecká fakulta | Deriváty triterpenoidu pro lécbu nádorových onemocnení a farmaceutická kompozice je obsahující |
| KR101061911B1 (ko) * | 2009-04-01 | 2011-09-02 | 주식회사 페라온 | 페길레이션된 베튤린 유도체 및 그를 포함하는 화장료 조성물 |
| CN102603858B (zh) * | 2012-03-02 | 2014-07-02 | 东北林业大学 | 桦木醇的含氮杂环衍生物、制备方法及用途 |
| US9637516B2 (en) | 2012-12-31 | 2017-05-02 | Hetero Research Foundation | Betulinic acid proline derivatives as HIV inhibitors |
| CN104910239B (zh) * | 2014-03-14 | 2018-12-07 | 中国科学院上海药物研究所 | 五环三萜类化合物及其制备方法、药物组合物和用途 |
| US20170129916A1 (en) | 2014-06-26 | 2017-05-11 | Hetero Research Foundation | Novel betulinic proline imidazole derivatives as hiv inhibitors |
| MA40886B1 (fr) | 2015-02-09 | 2020-03-31 | Hetero Research Foundation | Nouveau triterpénone en c-3 avec des dérivés d'amide inverse en c-28 en tant qu'inhibiteurs du vih |
| US10370405B2 (en) | 2015-03-16 | 2019-08-06 | Hetero Labs Limited | C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors |
| CN109700760B (zh) * | 2019-03-07 | 2021-04-06 | 南京中医药大学 | 一种白桦脂酸纳米混悬剂及其制备方法 |
| CN113896757B (zh) * | 2020-07-07 | 2024-12-06 | 中国科学院上海药物研究所 | 一类五环三萜类碳苷化合物及其制备方法和用途 |
| CN113135974B (zh) * | 2021-03-24 | 2022-05-06 | 广东工业大学 | 白桦脂醇衍生物及其在制备抗肿瘤药物中的应用 |
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| EP0542622A1 (fr) * | 1991-11-13 | 1993-05-19 | Aventis Pharma S.A. | Nouveaux dérivés du lupane, leur préparation et les compositions pharmaceutiques qui les contiennent |
| JPH07501068A (ja) * | 1991-05-09 | 1995-02-02 | ローン−プーラン・ロレ・ソシエテ・アノニム | ルパン誘導体、その製造及びそれを含有する製薬学的組成物 |
| WO1996039033A1 (en) * | 1995-06-05 | 1996-12-12 | The University Of North Carolina At Chapel Hill | Betulinic acid derivatives and uses therefor |
| WO1998051294A2 (en) * | 1997-05-16 | 1998-11-19 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| WO1998051293A1 (en) * | 1997-05-16 | 1998-11-19 | The Board Of Trustees Of The University Of Illinois | Use of betulinic acid derivatives for the treatment and prevention of melanoma |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1415601A (en) * | 1973-03-14 | 1975-11-26 | Biorex Laboratories Ltd | Dihydrobetulinic acid derivatives |
| JPS6417431A (en) * | 1987-07-13 | 1989-01-20 | Nec Corp | Manufacture of semiconductor integrated circuit device |
-
1999
- 1999-09-09 EP EP99963658A patent/EP1218402B1/en not_active Expired - Lifetime
- 1999-09-09 DE DE69917684T patent/DE69917684T2/de not_active Expired - Fee Related
- 1999-09-09 JP JP2001522252A patent/JP2003508543A/ja active Pending
- 1999-09-09 BR BR9917495-2A patent/BR9917495A/pt not_active IP Right Cessation
- 1999-09-09 AU AU20001/00A patent/AU780148B2/en not_active Ceased
- 1999-09-09 KR KR1020027003120A patent/KR100618100B1/ko not_active Expired - Fee Related
- 1999-09-09 CN CNB998169404A patent/CN1152046C/zh not_active Expired - Fee Related
- 1999-09-09 WO PCT/IN1999/000043 patent/WO2001018029A1/en not_active Ceased
- 1999-09-09 ES ES99963658T patent/ES2224735T3/es not_active Expired - Lifetime
- 1999-09-09 CA CA002384433A patent/CA2384433C/en not_active Expired - Fee Related
- 1999-09-09 AT AT99963658T patent/ATE267837T1/de not_active IP Right Cessation
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| JPH07501068A (ja) * | 1991-05-09 | 1995-02-02 | ローン−プーラン・ロレ・ソシエテ・アノニム | ルパン誘導体、その製造及びそれを含有する製薬学的組成物 |
| EP0542622A1 (fr) * | 1991-11-13 | 1993-05-19 | Aventis Pharma S.A. | Nouveaux dérivés du lupane, leur préparation et les compositions pharmaceutiques qui les contiennent |
| WO1996039033A1 (en) * | 1995-06-05 | 1996-12-12 | The University Of North Carolina At Chapel Hill | Betulinic acid derivatives and uses therefor |
| WO1998051294A2 (en) * | 1997-05-16 | 1998-11-19 | The Board Of Trustees Of The University Of Illinois | Method and composition for treating cancers |
| WO1998051293A1 (en) * | 1997-05-16 | 1998-11-19 | The Board Of Trustees Of The University Of Illinois | Use of betulinic acid derivatives for the treatment and prevention of melanoma |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020534358A (ja) * | 2017-09-18 | 2020-11-26 | 上海 インスティテュート オブ マテリア メディカ、チャイニーズ アカデミー オブ サイエンシーズＳｈａｎｇｈａｉ Ｉｎｓｔｉｔｕｔｅ Ｏｆ Ｍａｔｅｒｉａ Ｍｅｄｉｃａ， Ｃｈｉｎｅｓｅ Ａｃａｄｅｍｙ Ｏｆ Ｓｃｉｅｎｃｅｓ | ペンタシクロトリテルペン系化合物ならびにその製造方法、薬物組成物および使用 |
| US11192916B2 (en) | 2017-09-18 | 2021-12-07 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Pentacyclic triterpene compound and preparation method therefor, and pharmaceutical composition and use thereof |
| JP7029542B2 (ja) | 2017-09-18 | 2022-03-03 | 上海 インスティテュート オブ マテリア メディカ、チャイニーズ アカデミー オブ サイエンシーズ | ペンタシクロトリテルペン系化合物ならびにその製造方法、薬物組成物および使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2224735T3 (es) | 2005-03-01 |
| AU2000100A (en) | 2001-04-10 |
| DE69917684D1 (de) | 2004-07-01 |
| EP1218402A1 (en) | 2002-07-03 |
| EP1218402B1 (en) | 2004-05-26 |
| KR20020092908A (ko) | 2002-12-12 |
| DE69917684T2 (de) | 2005-07-21 |
| CN1152046C (zh) | 2004-06-02 |
| CA2384433C (en) | 2007-10-23 |
| WO2001018029A1 (en) | 2001-03-15 |
| AU780148B2 (en) | 2005-03-03 |
| BR9917495A (pt) | 2002-06-11 |
| KR100618100B1 (ko) | 2006-08-29 |
| ATE267837T1 (de) | 2004-06-15 |
| CA2384433A1 (en) | 2001-03-15 |
| CN1373769A (zh) | 2002-10-09 |
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