PH26024A - Castanospermine esters in the inhibition of tumor metastasis - Google Patents
Castanospermine esters in the inhibition of tumor metastasis Download PDFInfo
- Publication number
- PH26024A PH26024A PH39704A PH39704A PH26024A PH 26024 A PH26024 A PH 26024A PH 39704 A PH39704 A PH 39704A PH 39704 A PH39704 A PH 39704A PH 26024 A PH26024 A PH 26024A
- Authority
- PH
- Philippines
- Prior art keywords
- benzoyl
- patient
- formation
- melanoma
- cancer
- Prior art date
Links
- 206010027476 Metastases Diseases 0.000 title claims abstract description 34
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 27
- JDVVGAQPNNXQDW-TVNFTVLESA-N Castinospermine Chemical class C1[C@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H](O)CCN21 JDVVGAQPNNXQDW-TVNFTVLESA-N 0.000 title abstract description 16
- 230000005764 inhibitory process Effects 0.000 title abstract description 12
- 230000009401 metastasis Effects 0.000 title description 22
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- -1 trichlorobenzoyl Chemical group 0.000 claims description 21
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 201000001441 melanoma Diseases 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 208000020816 lung neoplasm Diseases 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
- 210000004072 lung Anatomy 0.000 claims description 7
- 201000005202 lung cancer Diseases 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- DWBDMLGCCJIACZ-ODXJTPSBSA-N [(1s,6s,7s,8r,8ar)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] benzoate Chemical compound O([C@H]1CN2CC[C@@H]([C@@H]2[C@@H](O)[C@@H]1O)O)C(=O)C1=CC=CC=C1 DWBDMLGCCJIACZ-ODXJTPSBSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
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- 125000006331 halo benzoyl group Chemical group 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960002247 lomustine Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- FBZXCCIWGJFHAA-UHFFFAOYSA-N methylsulfonyl benzoate Chemical compound CS(=O)(=O)OC(=O)C1=CC=CC=C1 FBZXCCIWGJFHAA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002818 ornithine decarboxylase inhibitor Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000011581 secondary neoplasm Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/284,510 US4952585A (en) | 1988-12-15 | 1988-12-15 | Castanospermine esters in the inhibition of tumor metastasis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26024A true PH26024A (en) | 1992-01-24 |
Family
ID=23090466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH39704A PH26024A (en) | 1988-12-15 | 1989-12-14 | Castanospermine esters in the inhibition of tumor metastasis |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4952585A (da) |
| EP (1) | EP0373663B1 (da) |
| JP (1) | JP2963476B2 (da) |
| KR (1) | KR0135278B1 (da) |
| AT (1) | ATE96320T1 (da) |
| AU (1) | AU621431B2 (da) |
| DE (1) | DE68910287T2 (da) |
| DK (1) | DK634689A (da) |
| ES (1) | ES2061912T3 (da) |
| IE (1) | IE62014B1 (da) |
| PH (1) | PH26024A (da) |
| ZA (1) | ZA899451B (da) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5004746A (en) * | 1987-09-29 | 1991-04-02 | Merrell Dow Pharmaceuticals Inc. | Anti-retroviral castanospermine esters |
| US4970317A (en) * | 1989-08-08 | 1990-11-13 | Merrell Dow Pharmaceuticals Inc. | Process for the preparation of castanospermine esters |
| US5959111A (en) * | 1997-05-22 | 1999-09-28 | Hoechst Marion Roussel, Inc. | Process for preparing 6-0-monoesters of castanospermine |
| EP0983270B1 (en) * | 1997-05-22 | 2004-02-18 | Aventis Pharmaceuticals Inc. | Process for preparing 6-o-monoesters of castanospermine |
| US6013459A (en) * | 1997-06-12 | 2000-01-11 | Clinical Micro Sensors, Inc. | Detection of analytes using reorganization energy |
| WO2008088581A2 (en) * | 2006-08-02 | 2008-07-24 | United Therapeutics Corporation | Liposome treatment of viral infections |
| US20090252785A1 (en) * | 2008-03-26 | 2009-10-08 | University Of Oxford | Endoplasmic reticulum targeting liposomes |
| US8226684B2 (en) * | 2008-12-22 | 2012-07-24 | Ethicon, Inc. | Surgical sutures having collapsible tissue anchoring protrusions and methods therefor |
| KR20120059447A (ko) * | 2009-03-27 | 2012-06-08 | 더 챈슬러 마스터즈 앤드 스칼라스 오브 더 유니버시티 오브 옥스포드 | 콜레스테롤 수준 저하 리포좀 |
| US20190046497A1 (en) * | 2016-02-14 | 2019-02-14 | Yeda Research And Development Co., Ltd. | Methods of modulating protein exocytosis and uses of same in therapy |
| WO2018059215A1 (zh) | 2016-09-29 | 2018-04-05 | 广州君赫生物科技有限公司 | 降低saicar累积的化合物及应用 |
| AU2018253689B2 (en) | 2017-04-20 | 2020-07-23 | Geneheal Biotechnology Co., Ltd. | Applications of spermidine and its derivative |
| CA3057206C (en) | 2017-04-20 | 2022-11-01 | Geneheal Biotechnology Co., Ltd. | Applications of spermine and its derivative in preparation of antitumor drug |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792558A (en) * | 1987-05-29 | 1988-12-20 | Merrell Dow Pharmaceuticals Inc. | Castanospermine for inhibiting tumor metastasis |
| CA1315276C (en) * | 1987-07-02 | 1993-03-30 | Paul S. Liu | Castanospermine esters and glycosides |
| US5004746A (en) * | 1987-09-29 | 1991-04-02 | Merrell Dow Pharmaceuticals Inc. | Anti-retroviral castanospermine esters |
| AU618838B2 (en) * | 1988-08-10 | 1992-01-09 | Praxis Pharmaceuticals, Inc. | Use of castanospermine as an anti-inflammatory and immunosuppressant agent |
-
1988
- 1988-12-15 US US07/284,510 patent/US4952585A/en not_active Expired - Fee Related
-
1989
- 1989-12-11 ZA ZA899451A patent/ZA899451B/xx unknown
- 1989-12-13 KR KR1019890018449A patent/KR0135278B1/ko not_active IP Right Cessation
- 1989-12-13 AU AU46707/89A patent/AU621431B2/en not_active Ceased
- 1989-12-14 AT AT89123189T patent/ATE96320T1/de not_active IP Right Cessation
- 1989-12-14 DE DE89123189T patent/DE68910287T2/de not_active Expired - Fee Related
- 1989-12-14 IE IE400989A patent/IE62014B1/en not_active IP Right Cessation
- 1989-12-14 PH PH39704A patent/PH26024A/en unknown
- 1989-12-14 ES ES89123189T patent/ES2061912T3/es not_active Expired - Lifetime
- 1989-12-14 EP EP89123189A patent/EP0373663B1/en not_active Expired - Lifetime
- 1989-12-14 DK DK634689A patent/DK634689A/da not_active Application Discontinuation
- 1989-12-15 JP JP1324194A patent/JP2963476B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DK634689D0 (da) | 1989-12-14 |
| JP2963476B2 (ja) | 1999-10-18 |
| KR910011256A (ko) | 1991-08-07 |
| KR0135278B1 (ko) | 1998-04-23 |
| ATE96320T1 (de) | 1993-11-15 |
| EP0373663A2 (en) | 1990-06-20 |
| IE894009L (en) | 1990-06-15 |
| AU4670789A (en) | 1990-06-21 |
| US4952585A (en) | 1990-08-28 |
| AU621431B2 (en) | 1992-03-12 |
| EP0373663A3 (en) | 1990-09-12 |
| DE68910287D1 (de) | 1993-12-02 |
| EP0373663B1 (en) | 1993-10-27 |
| DE68910287T2 (de) | 1994-03-10 |
| ES2061912T3 (es) | 1994-12-16 |
| ZA899451B (en) | 1990-09-26 |
| JPH02212427A (ja) | 1990-08-23 |
| DK634689A (da) | 1990-06-16 |
| IE62014B1 (en) | 1994-12-14 |
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