AT392273B - Verfahren zur herstellung von platinkomplexen - Google Patents

Verfahren zur herstellung von platinkomplexen Download PDF

Info

Publication number: AT392273B
Authority: AT; Austria
Prior art keywords: platinum; aminomethylpyrrolidine; optically active; active derivative; formula
Prior art date: 1988-04-07

Application number

AT816/89A

Other languages

German (de)

English (en)

Other versions

ATA81689A (de

Original Assignee

Chugai Pharmaceutical Co Ltd

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.)

1988-04-07

Filing date

1989-04-06

Publication date

1991-02-25

1989-04-06 Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd

1990-08-15 Publication of ATA81689A publication Critical patent/ATA81689A/de

1991-02-25 Application granted granted Critical

1991-02-25 Publication of AT392273B publication Critical patent/AT392273B/de

Links

BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims description 29
238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 31
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims abstract description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
-1 [(R) -2-aminomethylpyrrolidine] platinum (II) Chemical compound 0.000 claims description 16
CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 claims description 16
229910052697 platinum Inorganic materials 0.000 claims description 11
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 10
238000001914 filtration Methods 0.000 claims description 8
238000003756 stirring Methods 0.000 claims description 8
NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 0.000 claims description 7
159000000007 calcium salts Chemical class 0.000 claims description 6
XNGYKPINNDWGGF-UHFFFAOYSA-L silver oxalate Chemical compound [Ag+].[Ag+].[O-]C(=O)C([O-])=O XNGYKPINNDWGGF-UHFFFAOYSA-L 0.000 claims description 6
239000000725 suspension Substances 0.000 claims description 5
229910021607 Silver chloride Inorganic materials 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical compound NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 4
238000000354 decomposition reaction Methods 0.000 claims description 3
238000005273 aeration Methods 0.000 claims description 2
238000007796 conventional method Methods 0.000 claims description 2
239000013078 crystal Substances 0.000 claims 3
238000006243 chemical reaction Methods 0.000 abstract description 21
229910052708 sodium Inorganic materials 0.000 abstract description 4
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 abstract description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 3
239000011734 sodium Substances 0.000 abstract description 3
239000002246 antineoplastic agent Substances 0.000 abstract description 2
125000005843 halogen group Chemical group 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000706 filtrate Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
VYIWZEHRTLSWFL-UHFFFAOYSA-N [Pt+2].NCC1NCCC1 Chemical compound [Pt+2].NCC1NCCC1 VYIWZEHRTLSWFL-UHFFFAOYSA-N 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
230000000259 anti-tumor effect Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000002198 insoluble material Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 3
150000003057 platinum Chemical class 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
239000004332 silver Substances 0.000 description 3
230000002194 synthesizing effect Effects 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QZRLFKCODRAOAY-ZJIMSODOSA-N [(2r)-pyrrolidin-2-yl]methanamine;dihydrochloride Chemical compound Cl.Cl.NC[C@H]1CCCN1 QZRLFKCODRAOAY-ZJIMSODOSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910019029 PtCl4 Inorganic materials 0.000 description 1
QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
125000004436 sodium atom Chemical group 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
238000004448 titration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/04—Saturated compounds having a carboxyl group bound to a three or four-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

AT816/89A 1988-04-07 1989-04-06 Verfahren zur herstellung von platinkomplexen AT392273B (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP8559588		1988-04-07
JP8559488		1988-04-07

Publications (2)

Publication Number	Publication Date
ATA81689A ATA81689A (de)	1990-08-15
AT392273B true AT392273B (de)	1991-02-25

Family

ID=26426606

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT816/89A AT392273B (de)	1988-04-07	1989-04-06	Verfahren zur herstellung von platinkomplexen

Country Status (4)

Country	Link
KR (1)	KR950000982B1 (es)
AT (1)	AT392273B (es)
ES (1)	ES2016441A6 (es)
HU (1)	HU203558B (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2042364B1 (es) *	1991-06-05	1994-07-16	Ferrer Int	Procedimiento de obtencion de nuevos derivados de platino con aminopirrolidinas.
ES2056721B1 (es) *	1991-06-05	1995-05-01	Ferrer Int	Mejoras en el objeto de la patente de invencion n{ 9101355 que se refiere a procedimiento de obtencion de nuevos derivados de platino con aminopirrolidinas.

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59139360A (ja) *	1983-01-21	1984-08-10	Tanabe Seiyaku Co Ltd	新規有機白金錯体及びその製法

1989
- 1989-04-06 AT AT816/89A patent/AT392273B/de active
- 1989-04-06 ES ES8901207A patent/ES2016441A6/es not_active Expired - Lifetime
- 1989-04-07 KR KR1019890004620A patent/KR950000982B1/ko not_active Expired - Fee Related
- 1989-04-07 HU HU891684A patent/HU203558B/hu not_active IP Right Cessation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59139360A (ja) *	1983-01-21	1984-08-10	Tanabe Seiyaku Co Ltd	新規有機白金錯体及びその製法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF MEDICINAL CHEMISTRY, BAND 21, NR. 7, JULI 1978 YOSHINORI KIDANI ET AL. ''ANTTUMOR ACTIVITY OF 1,2-DIAMINOCYCLOHEXANE-PLATINUM COMPLEXES AGAINST SARCOMA 180 ASCITES FORM'' SEITEN 1315-1318. *
PATENT ABSTRACTS OF JAPAN, UNEXAMINED APPLICATION, SEKTION C, BAND 8, NR. 260, 29. NOVEMBER 1984 THE PATENT OFFICE JAPANESE GOVERNMENT SEITE 134 C 254 & JP-A-59 139 360 (TANABE SEIYAKU K.K. ET.AL.)* *

Also Published As

Publication number	Publication date
HUT51639A (en)	1990-05-28
KR890016054A (ko)	1989-11-28
ATA81689A (de)	1990-08-15
ES2016441A6 (es)	1990-11-01
KR950000982B1 (ko)	1995-02-06
HU203558B (en)	1991-08-28

Legal Events

Date	Code	Title
1993-04-15	UEP	Publication of translation of european patent specification
1994-01-15	EEIH	Change in the person of patent owner
2000-05-15	UEP	Publication of translation of european patent specification

Publication	Publication Date	Title
DE60023859T2 (de)	2006-08-03	Verfahren zur herstellung von amin-platin-komplexen
DE3586759T2 (de)	1993-03-04	Antitumor-platin-komplexe.
DE69726408T2 (de)	2004-05-19	Verfahren zur herstellung von platinverbindungen
DE69029138T2 (de)	1997-03-06	Neue bis-platinkomplexe als chemotherapeutisches mittel
DE3843571A1 (de)	1989-07-20	1,2-bis(aminomethyl)cyclobutan-platin-komplexe
DE2916145A1 (de)	1979-10-31	Stoffzusammensetzung mit platin
DE3406161A1 (de)	1984-08-23	Verfahren zur darstellung von platin(ii)-komplexen
DD156909A5 (de)	1982-09-29	Verfahren zur herstellung von platin(iv)-diaminkomplexen
DE2845371A1 (de)	1979-04-26	Platinkomplexverbindung, pharmazeutische stoffzusammensetzung mit einer solchen verbindung und deren anwendung
DE3134671A1 (de)	1982-06-16	Platin-komplexverbindung
CH631431A5 (de)	1982-08-13	Verfahren zur herstellung von platin(iv)-koordinationsverbindungen.
DE69422712T2 (de)	2000-07-20	Tris-platin-komplexe
DE2707934A1 (de)	1977-09-01	Gemische von platin enthaltenden stoffen, insbesondere gemische von platin enthaltenden stoffen zur chemotherapeutischen behandlung von krebs
DE3438440A1 (de)	1985-05-02	Platin-diamin-komplex
DE69507694T2 (de)	1999-07-22	Trinukleare kationische platinkomplexe mit antitumor wirkung sowie diese enthaltende pharmazeutische zusammensetzungen
Raudaschl-Sieber et al.	1985	Reaction of cyanide with platinum-nucleobase complexes: preparative, spectroscopic, and structural studies. Unexpected stability of platinum-thymine and platinum-uracil complexes
DE3008662A1 (de)	1980-09-11	Aethylendiamin-platin(ii)- und 1,2-diaminocyclohexan-platin(ii)-pyrophosphat-komplexe
DE69627472T2 (de)	2003-12-18	Verfahren zur Herstellung von Platin Verbindungen
DE102004005906B3 (de)	2005-09-29	Verfahren zur Herstellung von 1,2-Diaminocylohexan-Platin(II)-Komplexen
DE69813903T2 (de)	2003-12-18	Antikrebs-platin-(vi)-komplexe zur oralen verabreichung
AT392273B (de)	1991-02-25	Verfahren zur herstellung von platinkomplexen
DE3490640C2 (de)	1990-04-19	Platin (II)-Carboxylatokomplexe und Verfahren zu ihrer Herstellung
DE3874816T2 (de)	1993-03-25	Verfahren zur herstellung von cisplatin analogen verbindungen.
DE3928032C2 (de)	1996-10-17	Organogermaniumverbindungen und Verfahren zu ihrer Erzeugung
DE3022957C2 (es)	1991-03-21