HU203558B - New process for producing complexes of platinum - Google Patents

New process for producing complexes of platinum Download PDF

Info

Publication number: HU203558B
Authority: HU; Hungary
Prior art keywords: platinum; pyrrolidine; aminomethyl; optically active; silver
Prior art date: 1988-04-07

Application number

HU891684A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT51639A (en

Inventor

Masahiro Kato

Hirohito Shimizu

Tadao Michishita

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

1989-04-07

Publication date

1991-08-28

1989-04-07 Application filed by Chugai Pharmaceutical Co Ltd filed Critical Chugai Pharmaceutical Co Ltd

1990-05-28 Publication of HUT51639A publication Critical patent/HUT51639A/hu

1991-08-28 Publication of HU203558B publication Critical patent/HU203558B/hu

Links

BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims description 28
229910052697 platinum Inorganic materials 0.000 title claims description 12
238000000034 method Methods 0.000 title abstract description 33
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 claims description 9
NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 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
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 6
239000007795 chemical reaction product Substances 0.000 claims description 5
AUKXFNABVHIUAC-UHFFFAOYSA-N pyrrolidin-2-ylmethylamine Chemical compound NCC1CCCN1 AUKXFNABVHIUAC-UHFFFAOYSA-N 0.000 claims description 5
150000004985 diamines Chemical class 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
159000000007 calcium salts Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 abstract description 15
238000006243 chemical reaction Methods 0.000 abstract description 9
229910052799 carbon Inorganic materials 0.000 abstract description 4
125000004432 carbon atom Chemical group C* 0.000 abstract description 4
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
239000011734 sodium Substances 0.000 abstract description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 2
239000002246 antineoplastic agent Substances 0.000 abstract description 2
125000005843 halogen group Chemical group 0.000 abstract description 2
-1 IV Chemical compound 0.000 description 43
238000001914 filtration Methods 0.000 description 16
239000000706 filtrate Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
150000001875 compounds Chemical class 0.000 description 14
239000000203 mixture Substances 0.000 description 10
229910021607 Silver chloride Inorganic materials 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 9
239000002244 precipitate Substances 0.000 description 8
229910052709 silver Inorganic materials 0.000 description 8
239000004332 silver Substances 0.000 description 8
239000002198 insoluble material Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
239000000243 solution Substances 0.000 description 5
VCBOVIRRWXUOOY-UHFFFAOYSA-L C1(CCC1)(C(=O)[O-])C(=O)[O-].[Ag+2] Chemical compound C1(CCC1)(C(=O)[O-])C(=O)[O-].[Ag+2] VCBOVIRRWXUOOY-UHFFFAOYSA-L 0.000 description 4
230000000259 anti-tumor effect Effects 0.000 description 4
LVBJQCCMVUQDKO-UHFFFAOYSA-L calcium;cyclobutane-1,1-dicarboxylate Chemical compound [Ca+2].[O-]C(=O)C1(C([O-])=O)CCC1 LVBJQCCMVUQDKO-UHFFFAOYSA-L 0.000 description 4
239000013078 crystal Substances 0.000 description 4
XXUHLUDUCZQMDI-UHFFFAOYSA-L cyclobutane-1,1-dicarboxylate;platinum(2+);pyrrolidin-2-ylmethanamine Chemical compound [Pt+2].NCC1CCCN1.[O-]C(=O)C1(C([O-])=O)CCC1 XXUHLUDUCZQMDI-UHFFFAOYSA-L 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
150000003057 platinum Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
239000002178 crystalline material Substances 0.000 description 3
239000012467 final product Substances 0.000 description 3
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000004448 titration Methods 0.000 description 3
AUKXFNABVHIUAC-RXMQYKEDSA-N (R)-pyrrolidin-2-ylmethylamine Chemical compound NC[C@H]1CCCN1 AUKXFNABVHIUAC-RXMQYKEDSA-N 0.000 description 2
238000005273 aeration Methods 0.000 description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000011152 fibreglass Substances 0.000 description 2
NWAHZABTSDUXMJ-UHFFFAOYSA-N platinum(2+);dinitrate Chemical compound [Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O NWAHZABTSDUXMJ-UHFFFAOYSA-N 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
238000011282 treatment Methods 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
101710134784 Agnoprotein Proteins 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
DOSXDVYWNFUSBU-UHFFFAOYSA-N [O-][N+](=O)[Pt][N+]([O-])=O Chemical compound [O-][N+](=O)[Pt][N+]([O-])=O DOSXDVYWNFUSBU-UHFFFAOYSA-N 0.000 description 1
VYIWZEHRTLSWFL-UHFFFAOYSA-N [Pt+2].NCC1NCCC1 Chemical compound [Pt+2].NCC1NCCC1 VYIWZEHRTLSWFL-UHFFFAOYSA-N 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
229960004316 cisplatin Drugs 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000003365 glass fiber Substances 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
150000002500 ions Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 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
BASFCYQUMIYNBI-DBXDQKISSA-N platinum-186 Chemical compound [186Pt] BASFCYQUMIYNBI-DBXDQKISSA-N 0.000 description 1
239000011591 potassium Chemical group 0.000 description 1
229910052700 potassium Chemical group 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
125000004436 sodium atom Chemical group 0.000 description 1
239000006228 supernatant 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HU891684A 1988-04-07 1989-04-07 New process for producing complexes of platinum HU203558B (en)

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
HUT51639A HUT51639A (en)	1990-05-28
HU203558B true HU203558B (en)	1991-08-28

Family

ID=26426606

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU891684A HU203558B (en)	1988-04-07	1989-04-07	New process for producing complexes of platinum

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
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.
ES2042364B1 (es) *	1991-06-05	1994-07-16	Ferrer Int	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 - Lifetime
- 1989-04-06 AT AT816/89A patent/AT392273B/de active
- 1989-04-07 HU HU891684A patent/HU203558B/hu not_active IP Right Cessation
- 1989-04-07 KR KR1019890004620A patent/KR950000982B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HUT51639A (en)	1990-05-28
ATA81689A (de)	1990-08-15
KR890016054A (ko)	1989-11-28
AT392273B (de)	1991-02-25
ES2016441A6 (es)	1990-11-01
KR950000982B1 (ko)	1995-02-06

Legal Events

Date	Code	Title	Description
2003-01-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
US7956208B2 (en)	2011-06-07	Preparation of platinum (II) complexes
JPH0462320B2 (de)	1992-10-05
US7888523B2 (en)	2011-02-15	Preparation of platinum(II) complexes
DE3843571A1 (de)	1989-07-20	1,2-bis(aminomethyl)cyclobutan-platin-komplexe
JPH0412277B2 (de)	1992-03-04
CN100408588C (zh)	2008-08-06	具有低含量伴生杂质的奥沙利铂及其制备方法
US7888390B2 (en)	2011-02-15	Preparation of platinum(II) complexes
CA2492254C (en)	2010-03-16	Process for the preparation of 1,2-diaminocyclohexane-platinum(ii) complexes
US7208616B2 (en)	2007-04-24	Cis-diiodo-(trans-L-1,2-cyclohexanediamine) platinum (II) complex and processes for preparing high purity oxaliplatin
JPH09278785A (ja)	1997-10-28	白金化合物の製造方法
EP0296321B1 (de)	1992-09-23	Verfahren zur Herstellung von Cisplatin analogen Verbindungen
RU2361817C1 (ru)	2009-07-20	Способ получения цис-дихлороди(этиламин)платины(ii)
KR950000982B1 (ko)	1995-02-06	백금착체의 제조방법
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
RU2186068C2 (ru)	2002-07-27	Способ очистки цис-дихлороамминизопропиламинплатины (ii)
JPS62298596A (ja)	1987-12-25	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
JPH0228135A (ja)	1990-01-30	白金錯体の製造方法
JPS62238297A (ja)	1987-10-19	白金錯体の製造方法
JPS6148495B2 (de)	1986-10-24
JP2857920B2 (ja)	1999-02-17	有機ゲルマニウム化合物及びその製造方法
JPH0578560B2 (de)	1993-10-29
JPH072741B2 (ja)	1995-01-18	（−）−１６−ブロモビンカジホルミンおよびその製造方法
JPH0665679B2 (ja)	1994-08-24	新規な白金錯体
HK1127357A (en)	2009-09-25	Preparation of platinum (ii) complexes