PH26024A - Castanospermine esters in the inhibition of tumor metastasis - Google Patents

Castanospermine esters in the inhibition of tumor metastasis Download PDF

Info

Publication number: PH26024A
Authority: PH; Philippines
Prior art keywords: benzoyl; patient; formation; melanoma; cancer
Prior art date: 1988-12-15

Application number

PH39704A

Other languages

English (en)

Inventor

Sai P Sunkara

Paul S Liu

Original Assignee

Merrell Dow Pharma

Priority date (The priority date 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 date listed.)

1988-12-15

Filing date

1989-12-14

Publication date

1992-01-24

1989-12-14 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1992-01-24 Publication of PH26024A publication Critical patent/PH26024A/en

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
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
210000002307 prostate Anatomy 0.000 claims description 4
206010060862 Prostate cancer Diseases 0.000 claims description 3
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000006331 halo benzoyl group Chemical group 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
239000000203 mixture Substances 0.000 description 17
JDVVGAQPNNXQDW-WCMLQCRESA-N Castanospermine Natural products O[C@H]1[C@@H](O)[C@H]2[C@@H](O)CCN2C[C@H]1O JDVVGAQPNNXQDW-WCMLQCRESA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
239000000243 solution Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
108091003079 Bovine Serum Albumin Proteins 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000012894 fetal calf serum Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
238000011282 treatment Methods 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000003937 drug carrier Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
201000011510 cancer Diseases 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000306 component Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000001356 surgical procedure Methods 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
101100528916 Caenorhabditis elegans rol-6 gene Proteins 0.000 description 3
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DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000002246 antineoplastic agent Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
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238000002360 preparation method Methods 0.000 description 3
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238000004809 thin layer chromatography Methods 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229940034982 antineoplastic agent Drugs 0.000 description 2
230000008901 benefit Effects 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
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239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
210000003462 vein Anatomy 0.000 description 2
OZRWQPFBXDVLAH-YFKPBYRVSA-N (2s)-5-amino-2-(methylamino)pentanoic acid Chemical compound CN[C@H](C(O)=O)CCCN OZRWQPFBXDVLAH-YFKPBYRVSA-N 0.000 description 1
IATZHJGSCGLJSL-UHFFFAOYSA-N 1,2,3,5,6,7,8,8a-octahydroindolizin-1-ol Chemical compound C1CCCC2C(O)CCN21 IATZHJGSCGLJSL-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 1
RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
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229920002261 Corn starch Polymers 0.000 description 1
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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
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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
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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)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

PH39704A 1988-12-15 1989-12-14 Castanospermine esters in the inhibition of tumor metastasis PH26024A (en)

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 (de)
EP (1)	EP0373663B1 (de)
JP (1)	JP2963476B2 (de)
KR (1)	KR0135278B1 (de)
AT (1)	ATE96320T1 (de)
AU (1)	AU621431B2 (de)
DE (1)	DE68910287T2 (de)
DK (1)	DK634689A (de)
ES (1)	ES2061912T3 (de)
IE (1)	IE62014B1 (de)
PH (1)	PH26024A (de)
ZA (1)	ZA899451B (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
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
CA2287316C (en) *	1997-05-22	2005-02-08	Hoechst Marion Roussel, Inc.	Process for preparing 6-o-monoesters of castanospermine
US5959111A (en) *	1997-05-22	1999-09-28	Hoechst Marion Roussel, Inc.	Process for preparing 6-0-monoesters of castanospermine
US6013459A (en) *	1997-06-12	2000-01-11	Clinical Micro Sensors, Inc.	Detection of analytes using reorganization energy
JP2009545621A (ja) *	2006-08-02	2009-12-24	ユナイテッドセラピューティクスコーポレーション	ウィルス感染症のリポソーム処置
KR20100127842A (ko) *	2008-03-26	2010-12-06	유니버시티 오브 옥스퍼드	소포체 표적화 리포좀
US8226684B2 (en) *	2008-12-22	2012-07-24	Ethicon, Inc.	Surgical sutures having collapsible tissue anchoring protrusions and methods therefor
US8703744B2 (en) *	2009-03-27	2014-04-22	The Chancellor, Masters And Scholars Of The University Of Oxford	Cholesterol level lowering liposomes
WO2017138008A2 (en) *	2016-02-14	2017-08-17	Yeda Research And Development Co. Ltd.	Methods of modulating protein exocytosis and uses of same in therapy
WO2018059214A1 (zh)	2016-09-29	2018-04-05	广州君赫生物科技有限公司	影响saicar合成的化合物及应用
US11684593B2 (en)	2017-04-20	2023-06-27	Geneheal Biotechnology Co., Ltd.	Applications of spermine and its derivative in preparation of antitumor drug
CA3064486C (en)	2017-04-20	2023-08-01	Geneheal Biotechnology Co., Ltd.	Applications of spermidine and its derivatives
US12605349B2 (en)	2024-09-05	2026-04-21	Orbus Therapeutics, Inc.	Methods of treating grade 3 astrocytoma

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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 AU AU46707/89A patent/AU621431B2/en not_active Ceased
- 1989-12-13 KR KR1019890018449A patent/KR0135278B1/ko not_active Expired - Fee Related
- 1989-12-14 AT AT89123189T patent/ATE96320T1/de not_active IP Right Cessation
- 1989-12-14 DK DK634689A patent/DK634689A/da not_active Application Discontinuation
- 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 ES ES89123189T patent/ES2061912T3/es not_active Expired - Lifetime
- 1989-12-14 PH PH39704A patent/PH26024A/en unknown
- 1989-12-14 EP EP89123189A patent/EP0373663B1/de not_active Expired - Lifetime
- 1989-12-15 JP JP1324194A patent/JP2963476B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE68910287T2 (de)	1994-03-10
AU621431B2 (en)	1992-03-12
DK634689A (da)	1990-06-16
IE894009L (en)	1990-06-15
DK634689D0 (da)	1989-12-14
ES2061912T3 (es)	1994-12-16
EP0373663A2 (de)	1990-06-20
AU4670789A (en)	1990-06-21
EP0373663B1 (de)	1993-10-27
JP2963476B2 (ja)	1999-10-18
EP0373663A3 (en)	1990-09-12
US4952585A (en)	1990-08-28
KR0135278B1 (ko)	1998-04-23
IE62014B1 (en)	1994-12-14
JPH02212427A (ja)	1990-08-23
KR910011256A (ko)	1991-08-07
ATE96320T1 (de)	1993-11-15
ZA899451B (en)	1990-09-26
DE68910287D1 (de)	1993-12-02

Publication	Publication Date	Title
PH26024A (en)	1992-01-24	Castanospermine esters in the inhibition of tumor metastasis
JPH05222048A (ja)	1993-08-31	水溶性カンプトテシン誘導体
KR100293867B1 (ko)	2001-09-17	아미노스틸바졸유도체및의약
AU717159B2 (en)	2000-03-16	New benzofuranone derivatives and a method for producing them
JPS62111962A (ja)	1987-05-22	３−フエニルチオメチルスチレン誘導体
US4293549A (en)	1981-10-06	Quinolinyl guanidines having antiinflammatory, analgesic or antipyretic activity
CS262690B2 (en)	1989-03-14	Process for preparing 1-/hydroxystyryl/-5h-2,3-benzodiazepines
EP0816338B1 (de)	2003-02-12	3-(bis-substituierte-phenylmethylen)oxindol-derivate
EP0228959A2 (de)	1987-07-15	Aminostyryl-Verbindungen und diese als wirksame Bestandteile enthaltende leukotrienantagonistische Zusammensetzung und Verfahren um durch ihre Anwendung SRS entgegenzuwirken
US4076829A (en)	1978-02-28	Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases
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HUT61966A (en)	1993-03-29	Process for producing new phenylalkyl aminoalkyl derivatives and pharmaceutical compositions comprising such compounds
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US4152446A (en)	1979-05-01	Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases
US5849756A (en)	1998-12-15	Pharmaceutical composition and method for modulating the immune reaction