NO311839B1 - Forbindelser med camptothecin-grunnstruktur, isolert fra Mappia foetida, og anvendelse derav som utgangsmaterialer for nyelegemidler samt som terapeutiske midler - Google Patents

Forbindelser med camptothecin-grunnstruktur, isolert fra Mappia foetida, og anvendelse derav som utgangsmaterialer for nyelegemidler samt som terapeutiske midler Download PDF

Info

Publication number: NO311839B1
Authority: NO; Norway
Prior art keywords: group; alkyl; camptothecin; optionally substituted; compound according
Prior art date: 1996-05-10

Application number

NO19985186A

Other languages

English (en)

Norwegian (no)

Other versions

NO985186D0 (no

NO985186L (no

Inventor

Ezio Bombardelli

Luisella Verotta

Original Assignee

Indena Spa

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.)

1996-05-10

Filing date

1998-11-06

Publication date

2002-02-04

1998-11-06 Application filed by Indena Spa filed Critical Indena Spa

1998-11-06 Publication of NO985186D0 publication Critical patent/NO985186D0/no

1998-11-06 Publication of NO985186L publication Critical patent/NO985186L/no

2002-02-04 Publication of NO311839B1 publication Critical patent/NO311839B1/no

Links

229940127093 camptothecin Drugs 0.000 title claims abstract description 20
KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 title claims abstract description 15
VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 title claims abstract description 15
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title claims abstract description 14
241000261227 Mappia foetida Species 0.000 title claims abstract description 9
150000001875 compounds Chemical class 0.000 title claims description 21
239000007858 starting material Substances 0.000 title description 2
239000003814 drug Substances 0.000 title 2
229940079593 drug Drugs 0.000 title 1
229940124597 therapeutic agent Drugs 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
239000003513 alkali Substances 0.000 claims abstract description 4
125000003277 amino group Chemical group 0.000 claims abstract description 4
150000001768 cations Chemical class 0.000 claims abstract description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
125000004754 (C2-C12) dialkylamino group Chemical group 0.000 claims abstract description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 3
125000001769 aryl amino group Chemical group 0.000 claims abstract description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
229910052700 potassium Inorganic materials 0.000 claims abstract description 3
239000011591 potassium Substances 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
229910052708 sodium Inorganic materials 0.000 claims abstract description 3
239000011734 sodium Substances 0.000 claims abstract description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
-1 aliphatic ketones Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
239000002028 Biomass Substances 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
230000021736 acetylation Effects 0.000 claims description 2
238000006640 acetylation reaction Methods 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
230000002862 amidating effect Effects 0.000 claims 1
229940125904 compound 1 Drugs 0.000 claims 1
229940043239 cytotoxic antineoplastic drug Drugs 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
229930013930 alkaloid Natural products 0.000 abstract description 10
241000196324 Embryophyta Species 0.000 abstract description 2
101100295738 Gallus gallus COR3 gene Proteins 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
WSXJPXFVULHYMX-KRWDZBQOSA-N 7-[(1s)-1-hydroxypropyl]-8-methyl-11h-indolizino[1,2-b]quinolin-9-one Chemical compound C1=CC=C2C=C(CN3C4=CC(=C(C3=O)C)[C@@H](O)CC)C4=NC2=C1 WSXJPXFVULHYMX-KRWDZBQOSA-N 0.000 abstract 1
WSXJPXFVULHYMX-UHFFFAOYSA-N S-Mappicine Natural products C1=CC=C2C=C(CN3C4=CC(=C(C3=O)C)C(O)CC)C4=NC2=C1 WSXJPXFVULHYMX-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
XVMZDZFTCKLZTF-NRFANRHFSA-N 9-methoxycamptothecin Chemical compound C1=CC(OC)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 XVMZDZFTCKLZTF-NRFANRHFSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XVMZDZFTCKLZTF-UHFFFAOYSA-N 9-methoxycamtothecin Natural products C1=CC(OC)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 XVMZDZFTCKLZTF-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
BWFNZIXETJNOGM-UHFFFAOYSA-N Foetidin I Natural products C1=C2C3=NC4=CC=CC=C4C=C3CN2C(=O)C(COC(C)=O)=C1C(O)(CC)C(=O)OC(C=C1)=CC=C1C=CC(=O)NCCCNCCCCNC(=O)C=CC1=CC=C(O)C=C1 BWFNZIXETJNOGM-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
150000003797 alkaloid derivatives Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
238000003811 acetone extraction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 description 1
239000002021 butanolic extract Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
239000005418 vegetable material Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Medicines Containing Plant Substances (AREA)

NO19985186A 1996-05-10 1998-11-06 Forbindelser med camptothecin-grunnstruktur, isolert fra Mappia foetida, og anvendelse derav som utgangsmaterialer for nyelegemidler samt som terapeutiske midler NO311839B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT96MI000944A IT1283635B1 (it)	1996-05-10	1996-05-10	Composti a scheletro camptotecinico isolati da mappia foetida e loro uso come sintoni per farmaci o come principi attivi
PCT/EP1997/002244 WO1997043290A1 (en)	1996-05-10	1997-05-02	Camptothecin-skeleton compounds isolated from mappia foetida and the use thereof as syntones for novel medicaments as well as therapeutical agents

Publications (3)

Publication Number	Publication Date
NO985186D0 NO985186D0 (no)	1998-11-06
NO985186L NO985186L (no)	1998-11-06
NO311839B1 true NO311839B1 (no)	2002-02-04

Family

ID=11374242

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19985186A NO311839B1 (no)	1996-05-10	1998-11-06	Forbindelser med camptothecin-grunnstruktur, isolert fra Mappia foetida, og anvendelse derav som utgangsmaterialer for nyelegemidler samt som terapeutiske midler

Country Status (20)

Country	Link
US (1)	US6121277A (ja)
EP (1)	EP0912573B1 (ja)
JP (1)	JP3483257B2 (ja)
KR (1)	KR20000010893A (ja)
CN (1)	CN1082509C (ja)
AT (1)	ATE211140T1 (ja)
AU (1)	AU715482B2 (ja)
CA (1)	CA2253914C (ja)
CZ (1)	CZ287901B6 (ja)
DE (1)	DE69709357T2 (ja)
DK (1)	DK0912573T3 (ja)
ES (1)	ES2169389T3 (ja)
HK (1)	HK1019600A1 (ja)
IT (1)	IT1283635B1 (ja)
NO (1)	NO311839B1 (ja)
PL (1)	PL188228B1 (ja)
PT (1)	PT912573E (ja)
RU (1)	RU2169149C2 (ja)
SK (1)	SK283050B6 (ja)
WO (1)	WO1997043290A1 (ja)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2792937B1 (fr)	1999-04-27	2001-08-10	Cemaf	NOUVEAUX DERIVES DE PYRROLO-(3,4-b) QUINOLEINE, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION A TITRE DE MEDICAMENT
AU775373B2 (en)	1999-10-01	2004-07-29	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
AU2004238329A1 (en)	2003-05-12	2004-11-25	Purdue Research Foundation	Cytotoxic indeno and isoindoloisoquinolones
ITMI20051348A1 (it) *	2005-07-14	2007-01-15	Indena Spa	Analoghi della camptotecina loro processo di ottenimento loro uso e formulazioni che li contengono
CN100339377C (zh) *	2005-09-05	2007-09-26	合肥中科大生物技术有限公司	喜树碱衍生物及其制备
CN1319971C (zh) *	2005-09-09	2007-06-06	合肥中科大生物技术有限公司	喜树碱衍生物及其用途
WO2012176145A1 (en) *	2011-06-22	2012-12-27	Council Of Scientific & Industrial Research	Insecticidal compositions isolated from nothapodites foetida and process for the extraction thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1269862B (it) *	1994-05-30	1997-04-15	Indena Spa	Alcaloidi da mappia foetida, loro uso e formulazioni che li contengono

1996
- 1996-05-10 IT IT96MI000944A patent/IT1283635B1/it active IP Right Grant
1997
- 1997-05-02 AT AT97922937T patent/ATE211140T1/de not_active IP Right Cessation
- 1997-05-02 DE DE69709357T patent/DE69709357T2/de not_active Expired - Lifetime
- 1997-05-02 ES ES97922937T patent/ES2169389T3/es not_active Expired - Lifetime
- 1997-05-02 KR KR1019980709040A patent/KR20000010893A/ko not_active Application Discontinuation
- 1997-05-02 EP EP97922937A patent/EP0912573B1/en not_active Expired - Lifetime
- 1997-05-02 RU RU98122224/04A patent/RU2169149C2/ru not_active IP Right Cessation
- 1997-05-02 US US09/155,960 patent/US6121277A/en not_active Expired - Fee Related
- 1997-05-02 SK SK1540-98A patent/SK283050B6/sk not_active IP Right Cessation
- 1997-05-02 DK DK97922937T patent/DK0912573T3/da active
- 1997-05-02 PL PL97329765A patent/PL188228B1/pl not_active IP Right Cessation
- 1997-05-02 CZ CZ19983620A patent/CZ287901B6/cs not_active IP Right Cessation
- 1997-05-02 AU AU28901/97A patent/AU715482B2/en not_active Ceased
- 1997-05-02 JP JP54044797A patent/JP3483257B2/ja not_active Expired - Fee Related
- 1997-05-02 CA CA002253914A patent/CA2253914C/en not_active Expired - Fee Related
- 1997-05-02 WO PCT/EP1997/002244 patent/WO1997043290A1/en not_active Application Discontinuation
- 1997-05-02 CN CN97194492A patent/CN1082509C/zh not_active Expired - Fee Related
- 1997-05-02 PT PT97922937T patent/PT912573E/pt unknown
1998
- 1998-11-06 NO NO19985186A patent/NO311839B1/no not_active IP Right Cessation
1999
- 1999-10-27 HK HK99104790A patent/HK1019600A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0912573A1 (en)	1999-05-06
JP3483257B2 (ja)	2004-01-06
CZ287901B6 (cs)	2001-03-14
HK1019600A1 (en)	2000-02-18
ITMI960944A0 (ja)	1996-05-10
CN1082509C (zh)	2002-04-10
WO1997043290A1 (en)	1997-11-20
NO985186D0 (no)	1998-11-06
CN1218474A (zh)	1999-06-02
IT1283635B1 (it)	1998-04-23
CZ362098A3 (cs)	1999-06-16
DK0912573T3 (da)	2002-04-15
PT912573E (pt)	2002-06-28
AU2890197A (en)	1997-12-05
JP2000503666A (ja)	2000-03-28
US6121277A (en)	2000-09-19
PL329765A1 (en)	1999-04-12
ES2169389T3 (es)	2002-07-01
DE69709357D1 (de)	2002-01-31
SK283050B6 (sk)	2003-02-04
NO985186L (no)	1998-11-06
PL188228B1 (pl)	2004-12-31
EP0912573B1 (en)	2001-12-19
KR20000010893A (ko)	2000-02-25
AU715482B2 (en)	2000-02-03
SK154098A3 (en)	1999-04-13
ATE211140T1 (de)	2002-01-15
DE69709357T2 (de)	2002-08-22
CA2253914A1 (en)	1997-11-20
RU2169149C2 (ru)	2001-06-20
ITMI960944A1 (it)	1997-11-10
CA2253914C (en)	2002-10-22

Legal Events

Date	Code	Title	Description
2011-12-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
Takayama et al.	1998	New indole alkaloids from the leaves of Malaysian Mitragyna speciosa
NO311839B1 (no)	2002-02-04	Forbindelser med camptothecin-grunnstruktur, isolert fra Mappia foetida, og anvendelse derav som utgangsmaterialer for nyelegemidler samt som terapeutiske midler
Lian-niang et al.	1989	Isolation and Structure Elucidation of Seco-neokadsuranic Acid A and 3, 4-Seco-(24Z)-lanosta-4 (30), 8, 24-triene-3, 26-dioic Acid1
Hikino et al.	1983	Structure of hokbusine A and B, diterpenic alkaloids of Aconitum carmichaeli roots from Japan
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