KR950000982B1 - 백금착체의 제조방법 - Google Patents

백금착체의 제조방법 Download PDF

Info

Publication number: KR950000982B1
Authority: KR; South Korea
Prior art keywords: platinum; active substance; optically active; aminomethylpyrrolidine; formula
Prior art date: 1988-04-07

Application number

KR1019890004620A

Other languages

English (en)

Korean (ko)

Other versions

KR890016054A (ko

Inventor

마사히로 가또

히로히또 시미즈

다다오 미찌시따

Original Assignee

쥬우가이 세이야꾸 가부시끼가이샤

사노 하지메

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

1989-04-07

Publication date

1995-02-06

1989-04-07 Application filed by 쥬우가이 세이야꾸 가부시끼가이샤, 사노 하지메 filed Critical 쥬우가이 세이야꾸 가부시끼가이샤

1989-11-28 Publication of KR890016054A publication Critical patent/KR890016054A/ko

1995-02-06 Application granted granted Critical

1995-02-06 Publication of KR950000982B1 publication Critical patent/KR950000982B1/ko

Links

150000003057 platinum Chemical class 0.000 title claims description 8
238000000034 method Methods 0.000 title description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 30
239000013543 active substance Substances 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
238000004519 manufacturing process Methods 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 14
CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 claims description 13
229910052697 platinum Inorganic materials 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
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 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
159000000007 calcium salts Chemical class 0.000 claims description 5
150000004985 diamines Chemical class 0.000 claims description 5
NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 0.000 claims description 5
AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical compound NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 claims description 5
UDFWUWKGBBKQAF-UHFFFAOYSA-N oxalic acid;silver Chemical compound [Ag].OC(=O)C(O)=O UDFWUWKGBBKQAF-UHFFFAOYSA-N 0.000 claims 1
-1 carboxylato (2-aminomethylpyrrolidin) platinum (II) Chemical compound 0.000 description 16
239000000706 filtrate Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
VYIWZEHRTLSWFL-UHFFFAOYSA-N [Pt+2].NCC1NCCC1 Chemical compound [Pt+2].NCC1NCCC1 VYIWZEHRTLSWFL-UHFFFAOYSA-N 0.000 description 6
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
230000002194 synthesizing effect Effects 0.000 description 5
229910021607 Silver chloride Inorganic materials 0.000 description 4
230000000259 anti-tumor effect Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000004332 silver Substances 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
XNGYKPINNDWGGF-UHFFFAOYSA-L silver oxalate Chemical compound [Ag+].[Ag+].[O-]C(=O)C([O-])=O XNGYKPINNDWGGF-UHFFFAOYSA-L 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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
239000002246 antineoplastic agent Substances 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
239000013078 crystal Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
125000004436 sodium atom Chemical group 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
YXMWGHKZTMANIJ-UHFFFAOYSA-N 1h-pyrrol-2-ylmethanamine Chemical compound NCC1=CC=CN1 YXMWGHKZTMANIJ-UHFFFAOYSA-N 0.000 description 1
VQDJODAWOFNASI-UHFFFAOYSA-N 2-propylpropanedioic acid Chemical compound CCCC(C(O)=O)C(O)=O VQDJODAWOFNASI-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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
238000005273 aeration Methods 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
LVBJQCCMVUQDKO-UHFFFAOYSA-L calcium;cyclobutane-1,1-dicarboxylate Chemical class [Ca+2].[O-]C(=O)C1(C([O-])=O)CCC1 LVBJQCCMVUQDKO-UHFFFAOYSA-L 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000010946 fine silver Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
RYZCLUQMCYZBJQ-UHFFFAOYSA-H lead(2+);dicarbonate;dihydroxide Chemical compound [OH-].[OH-].[Pb+2].[Pb+2].[Pb+2].[O-]C([O-])=O.[O-]C([O-])=O RYZCLUQMCYZBJQ-UHFFFAOYSA-H 0.000 description 1
239000003446 ligand Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
IPOHICDGJPRKMS-UHFFFAOYSA-N platinum pyrrolidin-2-ylmethanamine Chemical compound [Pt].NCC1CCCN1 IPOHICDGJPRKMS-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

KR1019890004620A 1988-04-07 1989-04-07 백금착체의 제조방법 KR950000982B1 (ko)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP8559488		1988-04-07
JP8559588		1988-04-07
JP63-85595		1988-04-07
JP63-85594		1988-04-07

Publications (2)

Publication Number	Publication Date
KR890016054A KR890016054A (ko)	1989-11-28
KR950000982B1 true KR950000982B1 (ko)	1995-02-06

Family

ID=26426606

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019890004620A KR950000982B1 (ko)	1988-04-07	1989-04-07	백금착체의 제조방법

Country Status (4)

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

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.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2134103A (en) *	1983-01-21	1984-08-08	Tanabe Seiyaku Co	Novel organic platinum complex and process for the preparation thereof

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

Also Published As

Publication number	Publication date
KR890016054A (ko)	1989-11-28
AT392273B (de)	1991-02-25
ES2016441A6 (es)	1990-11-01
HUT51639A (en)	1990-05-28
HU203558B (en)	1991-08-28
ATA81689A (de)	1990-08-15

Legal Events

Date	Code	Title	Description
1989-04-07	A201	Request for examination
1994-06-25	E902	Notification of reason for refusal
1995-01-14	G160	Decision to publish patent application
1995-04-19	E701	Decision to grant or registration of patent right
1995-05-25	GRNT	Written decision to grant
2000-11-28	FPAY	Annual fee payment	Payment date: 20001128 Year of fee payment: 7
2002-02-07	LAPS	Lapse due to unpaid annual fee

Publication	Publication Date	Title
US7956208B2 (en)	2011-06-07	Preparation of platinum (II) complexes
JP3997232B2 (ja)	2007-10-24	１，２−ジアミノシクロヘキサン−白金（ｉｉ）−錯体の製造方法
JPH05271265A (ja)	1993-10-19	白金錯化合物及びその製造方法
JPH0462320B2 (de)	1992-10-05
JPS61171493A (ja)	1986-08-02	抗腫瘍性白金錯体
US7888523B2 (en)	2011-02-15	Preparation of platinum(II) complexes
JP2007505165A (ja)	2007-03-08	シス−ジヨード−（トランス−ｌ−１，２−シクロヘキサンジアミン）白金（ｉｉ）錯体及び高純度オキサリプラチンの調製方法
CZ297703B6 (cs)	2007-03-07	Oxaliplatina s nízkým obsahem doprovodných necistot a zpusob její výroby
US20090312417A1 (en)	2009-12-17	Platinum(ii) complexes, preparation and use
KR950000982B1 (ko)	1995-02-06	백금착체의 제조방법
US3799961A (en)	1974-03-26	Process for producing palladium(o)and platinum(o)complex compounds with triphenylphosphine
JPH0228135A (ja)	1990-01-30	白金錯体の製造方法
JPH0228134A (ja)	1990-01-30	カルボキシラト（ジアミン）プラチナムの製造方法
JPH07138025A (ja)	1995-05-30	テトラアンミン白金（ｉｉ）ジクロライドの製造方法
JPS62298596A (ja)	1987-12-25	白金錯体の製造方法
EP0261044A2 (de)	1988-03-23	Platin-Riboflavin-Komplexe
JPH09132583A (ja)	1997-05-20	シス−オキザラート（トランス−（−）−１、２−シクロヘキサンジアミン）白金（ｉｉ）の製造方法
JPH0395196A (ja)	1991-04-19	高純度白金錯体の製造方法
JPS5967262A (ja)	1984-04-16	新規有機金属錯体
JPS6344591A (ja)	1988-02-25	白金グリ−ン錯体の製造法
JPH0578378A (ja)	1993-03-30	新規抗がん性白金錯化合物及びその製造方法
JPS62226996A (ja)	1987-10-05	カルボキシラト（ジアミン）プラチナムの製造方法
JPS61148187A (ja)	1986-07-05	新規白金錯体
JPH10310594A (ja)	1998-11-24	白金錯体の製造方法
JPH0578560B2 (de)	1993-10-29