LU81763A1 - Procede de preparation du sulfate de vindesine - Google Patents

Procede de preparation du sulfate de vindesine Download PDF

Info

Publication number: LU81763A1
Authority: LU; Luxembourg
Prior art keywords: vindesin; sulfuric acid; vindesine; monosulfate; acetonitrile
Prior art date: 1978-10-10

Application number

LU81763A

Other languages

English (en)

French (fr)

Inventor

S Rolski

Original Assignee

Lilly Co Eli

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.)

1978-10-10

Filing date

1979-10-08

Publication date

1980-01-24

1979-10-08 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1980-01-24 Publication of LU81763A1 publication Critical patent/LU81763A1/fr

Links

238000000034 method Methods 0.000 title claims description 20
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 66
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 claims description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
238000003756 stirring Methods 0.000 claims description 9
230000015572 biosynthetic process Effects 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 5
150000004683 dihydrates Chemical class 0.000 claims 1
NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 23
229960004355 vindesine Drugs 0.000 description 23
UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 23
238000006386 neutralization reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
206010028980 Neoplasm Diseases 0.000 description 3
229910021653 sulphate ion Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
229960004528 vincristine Drugs 0.000 description 3
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 3
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 3
KABRXLINDSPGDF-UHFFFAOYSA-N 7-bromoisoquinoline Chemical compound C1=CN=CC2=CC(Br)=CC=C21 KABRXLINDSPGDF-UHFFFAOYSA-N 0.000 description 2
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
229930013930 alkaloid Natural products 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229960003048 vinblastine Drugs 0.000 description 2
229960005212 vindesine sulfate Drugs 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
206010025323 Lymphomas Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000863480 Vinca Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
201000005296 lung carcinoma Diseases 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000000954 titration curve Methods 0.000 description 1
JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
- 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
- A61P35/02—Antineoplastic agents specific for leukemia

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Oncology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Saccharide Compounds (AREA)

LU81763A 1978-10-10 1979-10-08 Procede de preparation du sulfate de vindesine LU81763A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US94959578A	1978-10-10	1978-10-10
US94959578		1978-10-10

Publications (1)

Publication Number	Publication Date
LU81763A1 true LU81763A1 (fr)	1980-01-24

Family

ID=25489302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81763A LU81763A1 (fr)	1978-10-10	1979-10-08	Procede de preparation du sulfate de vindesine

Country Status (32)

Country	Link
EP (1)	EP0009996B1 (de)
JP (1)	JPS5553295A (de)
KR (1)	KR850000150B1 (de)
AR (1)	AR225153A1 (de)
AT (1)	AT370422B (de)
AU (1)	AU525702B2 (de)
BE (1)	BE879213A (de)
BG (1)	BG34763A3 (de)
CA (1)	CA1114817A (de)
CH (2)	CH649301A5 (de)
CS (1)	CS235503B2 (de)
DD (1)	DD146461A5 (de)
DE (1)	DE2964913D1 (de)
DK (1)	DK146823C (de)
EG (1)	EG14140A (de)
ES (1)	ES484827A1 (de)
FI (1)	FI70223C (de)
FR (1)	FR2438659A1 (de)
GB (1)	GB2031893B (de)
GR (1)	GR72394B (de)
HU (1)	HU180744B (de)
IE (1)	IE48958B1 (de)
IL (1)	IL58390A (de)
LU (1)	LU81763A1 (de)
MY (1)	MY8500569A (de)
NZ (1)	NZ191744A (de)
PH (1)	PH16092A (de)
PL (1)	PL117678B1 (de)
PT (1)	PT70269A (de)
RO (1)	RO77380A (de)
YU (1)	YU241179A (de)
ZA (1)	ZA795268B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4558053A (en) *	1983-12-21	1985-12-10	Eli Lilly And Company	Naphthalene-1,5-disulfonate salts of dimeric indole-dihydroindole alkaloids
CN112592357B (zh) *	2020-12-22	2022-03-22	海南长春花药业有限公司	一种硫酸长春地辛的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL48685A (en) *	1975-01-09	1980-03-31	Lilly Co Eli	Amides of vincadioline and vinblastine
US4029663A (en) *	1975-07-10	1977-06-14	Eli Lilly And Company	Dimeric anhydro-vinca derivatives
GR69783B (de) *	1976-09-08	1982-07-07	Lilly Co Eli

1979
- 1979-10-02 AR AR278306A patent/AR225153A1/es active
- 1979-10-03 FI FI793065A patent/FI70223C/fi not_active IP Right Cessation
- 1979-10-03 PT PT70269A patent/PT70269A/de unknown
- 1979-10-03 AU AU51427/79A patent/AU525702B2/en not_active Expired
- 1979-10-03 CS CS796720A patent/CS235503B2/cs unknown
- 1979-10-03 YU YU02411/79A patent/YU241179A/xx unknown
- 1979-10-03 NZ NZ191744A patent/NZ191744A/xx unknown
- 1979-10-03 ZA ZA00795268A patent/ZA795268B/xx unknown
- 1979-10-04 JP JP12879579A patent/JPS5553295A/ja active Granted
- 1979-10-04 CA CA336,959A patent/CA1114817A/en not_active Expired
- 1979-10-04 IL IL58390A patent/IL58390A/xx unknown
- 1979-10-05 PL PL1979218756A patent/PL117678B1/pl unknown
- 1979-10-05 BE BE1/9554A patent/BE879213A/fr not_active IP Right Cessation
- 1979-10-05 FR FR7924841A patent/FR2438659A1/fr active Granted
- 1979-10-06 RO RO7998873A patent/RO77380A/ro unknown
- 1979-10-08 CH CH691/84A patent/CH649301A5/fr not_active IP Right Cessation
- 1979-10-08 LU LU81763A patent/LU81763A1/fr unknown
- 1979-10-08 CH CH904479A patent/CH645120A5/fr not_active IP Right Cessation
- 1979-10-08 ES ES484827A patent/ES484827A1/es not_active Expired
- 1979-10-08 BG BG045074A patent/BG34763A3/xx unknown
- 1979-10-08 GR GR60215A patent/GR72394B/el unknown
- 1979-10-09 IE IE1914/79A patent/IE48958B1/en not_active IP Right Cessation
- 1979-10-09 AT AT0658279A patent/AT370422B/de not_active IP Right Cessation
- 1979-10-09 EP EP79302152A patent/EP0009996B1/de not_active Expired
- 1979-10-09 DE DE7979302152T patent/DE2964913D1/de not_active Expired
- 1979-10-09 GB GB7935062A patent/GB2031893B/en not_active Expired
- 1979-10-09 EG EG590/79A patent/EG14140A/xx active
- 1979-10-09 DK DK422979A patent/DK146823C/da not_active IP Right Cessation
- 1979-10-09 HU HU79EI881A patent/HU180744B/hu unknown
- 1979-10-10 DD DD79216158A patent/DD146461A5/de unknown
- 1979-10-10 KR KR7903467A patent/KR850000150B1/ko not_active Expired
1981
- 1981-02-03 PH PH25176A patent/PH16092A/en unknown
1985
- 1985-12-30 MY MY569/85A patent/MY8500569A/xx unknown

Also Published As

Publication number	Publication date
FI70223B (fi)	1986-02-28
DK146823B (da)	1984-01-16
GB2031893A (en)	1980-04-30
MY8500569A (en)	1985-12-31
NZ191744A (en)	1981-05-29
EP0009996A1 (de)	1980-04-16
AU525702B2 (en)	1982-11-25
ATA658279A (de)	1982-08-15
IL58390A (en)	1982-07-30
IE48958B1 (en)	1985-06-26
DK146823C (da)	1984-07-02
CA1114817A (en)	1981-12-22
PL218756A1 (de)	1980-06-16
KR850000150B1 (ko)	1985-02-28
CH645120A5 (fr)	1984-09-14
ES484827A1 (es)	1980-10-01
CS235503B2 (en)	1985-05-15
EP0009996B1 (de)	1983-02-23
DD146461A5 (de)	1981-02-11
ZA795268B (en)	1981-05-27
AU5142779A (en)	1980-04-17
FR2438659A1 (fr)	1980-05-09
CH649301A5 (fr)	1985-05-15
IL58390A0 (en)	1980-01-31
JPS5553295A (en)	1980-04-18
IE791914L (en)	1980-04-10
PT70269A (de)	1979-11-01
PL117678B1 (en)	1981-08-31
DK422979A (da)	1980-04-11
GR72394B (de)	1983-11-01
JPS628119B2 (de)	1987-02-20
RO77380A (ro)	1981-11-04
AR225153A1 (es)	1982-02-26
DE2964913D1 (en)	1983-03-31
AT370422B (de)	1983-03-25
FI793065A7 (fi)	1980-04-11
HU180744B (en)	1983-04-29
YU241179A (en)	1983-01-21
EG14140A (en)	1983-09-30
KR830001282A (ko)	1983-04-30
FI70223C (fi)	1986-09-15
GB2031893B (en)	1983-03-30
FR2438659B1 (de)	1983-03-18
PH16092A (en)	1983-06-20
BG34763A3 (bg)	1983-11-15
BE879213A (fr)	1980-04-08

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EP0078785B1 (de)	1985-04-03	Salze der Valproinsäure, ihre Herstellung und ihre Verwendung
EP0010458B1 (de)	1983-08-10	Bis-Indole-Verbindungen, sie enthaltende pharmazeutische Zusammensetzungen, Verfahren zu ihrer Herstellung
CH639070A5 (fr)	1983-10-31	4-(di-n-propyl)amino-1,3,4,5-tetrahydrobenzo(cd)indole et composition pharmaceutique en contenant.
LU83423A1 (fr)	1981-09-11	Pneumatique radial pour vehicules tout-terrain
LU84143A1 (fr)	1982-09-13	Procede de preparation d'un polysulfate de chondroitine injectable,produit obtenu par ce procede et compositions pharmaceutiques le contenant
EP0840720B1 (de)	2003-09-10	Verfahren zur herstellung jodierter fettsäuren und ihrer derivate durch jodwasserstoffanlagerung unter anwendung von alkylsilylderivaten mit alkalijodiden und deren pharmakologischen aktivitäten
EP0479631B1 (de)	1994-11-02	Spiro[4,5]decanderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
CH645120A5 (fr)	1984-09-14	Procede de preparation de sulfate de vindesine.
FR2616429A1 (fr)	1988-12-16	Procede de preparation du 1,2,5,6,9,10-hexabromocyclododecane
WO2000035933A1 (fr)	2000-06-22	Troxerutine a forte teneur en trihydroxy-ethyl-rutoside et procede de preparation
FR2650280A1 (fr)	1991-02-01	(2r,cis)-1,2-epoxypropyl-phosphonate de mono-(2-ammonium-2-hydroxymethyl-1,3-propanediol) ayant des caracteristiques ameliorees de stabilite, son procede de preparation et compositions pharmaceutiques le contenant
DE3443467A1 (de)	1986-05-28	Mercaptanderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
WO2011042478A1 (fr)	2011-04-14	Procede de synthese de la 2-thiohistidine et analogues
EP0134729B1 (de)	1987-10-07	Verfahren zur Herstellung von Globin aus Haemoglobin und das in diesem Verfahren erhaltene Globin
EP0092287B1 (de)	1987-03-25	Acetylcystein-Salze, ihre Herstellung und Verwendung
EP0117861B1 (de)	1987-12-09	Verfahren zur Herstellung von Vincristin
KR102305089B1 (ko)	2021-09-27	멍게체액 추출물의 제조방법
EP1664044B1 (de)	2007-08-08	S-tenatoprazolnatrium-monohydrat-salz und dessen verwendung in form eines protonenpumpenhemmers
EP0253740B1 (de)	1990-05-30	Verfahren zur Herstellung einer wässerigen Lösung vom Natriumsalz des Methionins
FR2491927A1 (fr)	1982-04-16	Derives de cephalexine solubles dans l'eau, et procede pour leur preparation
CA1210762A (fr)	1986-09-02	Methode de preparation de vincristine
FR2582657A1 (fr)	1986-12-05	Procede de preparation de sels d'heparine
EP0017525B1 (de)	1983-09-28	Derivate von Tetrahydroalstonin, ihre Herstellung und ihre Verwendung in Arzneimitteln
CH634571A5 (fr)	1983-02-15	Procede de preparation d'un derive du thiophene et derive obtenu par ce procede.
JPH0128752B2 (de)	1989-06-05