UA80023C2 - Process for the synthesis of 2-substituted 1-(hydroxy-ethylidene)-1,1-bisphosfonic acid and salt thereof or hydrate - Google Patents

Process for the synthesis of 2-substituted 1-(hydroxy-ethylidene)-1,1-bisphosfonic acid and salt thereof or hydrate Download PDF

Info

Publication number: UA80023C2
Authority: UA; Ukraine
Prior art keywords: acid; formula; salt; mixture; substituted
Prior art date: 2003-01-28

Application number

UAA200508269A

Other languages

English (en)

Ukrainian (uk)

Inventor

Jozsef Neu

Janos Fischer

Tomas Fodor

Jozsef Torley

Tibor Gizur

Sandor Levai

Adam Demeter

Eva Perenyi

Original Assignee

Richter Gedeon Vedieceti Djar

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.)

2003-01-28

Filing date

2004-01-27

Publication date

2007-08-10

2004-01-27 Application filed by Richter Gedeon Vedieceti Djar filed Critical Richter Gedeon Vedieceti Djar

2007-08-10 Publication of UA80023C2 publication Critical patent/UA80023C2/uk

Links

238000000034 method Methods 0.000 title claims abstract description 28
239000002253 acid Substances 0.000 title claims abstract description 25
150000003839 salts Chemical class 0.000 title claims abstract description 14
230000015572 biosynthetic process Effects 0.000 title abstract description 9
238000003786 synthesis reaction Methods 0.000 title abstract description 8
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 36
229940098779 methanesulfonic acid Drugs 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 14
239000003153 chemical reaction reagent Substances 0.000 claims abstract description 13
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims abstract description 11
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims abstract description 11
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
230000003993 interaction Effects 0.000 claims description 3
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
150000004677 hydrates Chemical class 0.000 abstract description 5
239000000203 mixture Substances 0.000 description 26
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
229910001392 phosphorus oxide Inorganic materials 0.000 description 15
VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
229960003692 gamma aminobutyric acid Drugs 0.000 description 10
239000000047 product Substances 0.000 description 10
238000005954 phosphonylation reaction Methods 0.000 description 9
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 9
150000004682 monohydrates Chemical class 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 3
238000005260 corrosion Methods 0.000 description 3
230000007797 corrosion Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
150000007513 acids Chemical class 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 2
238000013021 overheating Methods 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 1
208000001132 Osteoporosis Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229950007593 homonicotinic acid Drugs 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000005457 optimization Methods 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
-1 phosphorus halides Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005406 washing 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UAA200508269A 2003-01-28 2004-01-27 Process for the synthesis of 2-substituted 1-(hydroxy-ethylidene)-1,1-bisphosfonic acid and salt thereof or hydrate UA80023C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU0300227A HUP0300227A2 (hu)	2003-01-28	2003-01-28	Eljárás nagy tisztaságú 2-szubsztituált -1-(hidroxi-etilidén)-1,1-biszfoszfonsavak és sóik előállítására
PCT/HU2004/000009 WO2004067541A1 (en)	2003-01-28	2004-01-27	Industrial process for the synthesis of 2-substituted 1-(hydroxy-ethylidene)-1,1-bisphosphonic acids of high purity and the salts thereof

Publications (1)

Publication Number	Publication Date
UA80023C2 true UA80023C2 (en)	2007-08-10

Family

ID=89981108

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200508269A UA80023C2 (en)	2003-01-28	2004-01-27	Process for the synthesis of 2-substituted 1-(hydroxy-ethylidene)-1,1-bisphosfonic acid and salt thereof or hydrate

Country Status (9)

Country	Link
US (1)	US7612229B2 (de)
EP (1)	EP1587814B1 (de)
AT (1)	ATE420885T1 (de)
DE (1)	DE602004019047D1 (de)
EA (1)	EA007947B1 (de)
HU (1)	HUP0300227A2 (de)
PL (1)	PL214441B1 (de)
UA (1)	UA80023C2 (de)
WO (1)	WO2004067541A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE461205T1 (de) *	2002-05-17	2010-04-15	Teva Pharma	Verwendung von bestimmten lösungsmitteln zur herstellung von bisphosphonsäuren
HUP0300227A2 (hu) *	2003-01-28	2004-09-28	Richter Gedeon Vegyészeti Gyár Rt.	Eljárás nagy tisztaságú 2-szubsztituált -1-(hidroxi-etilidén)-1,1-biszfoszfonsavak és sóik előállítására
EP1883644A2 (de) *	2005-05-06	2008-02-06	Medichem, S.A.	Process of making geminal bisphosphonic acids and pharmaceutically acceptable salts and/or hydrates thereof
JP5354858B2 (ja) *	2006-05-09	2013-11-27	株式会社Ａｄｅｋａ	スルホンアミド化合物の金属塩を含有するポリエステル樹脂組成物
EP2016084A2 (de)	2006-05-11	2009-01-21	Ind-Swift Laboratories Limited	Verfahren zur herstellung von reiner risedronsäure oder -salzen
WO2008152518A2 (en) *	2007-05-16	2008-12-18	Actavis Group Ptc Ehf	Process for the preparation of risedronic acid or risedronate sodium
WO2009050731A2 (en) *	2007-06-20	2009-04-23	Alkem Laboratories Ltd	Novel process for preparing risedronic acid
CA2775004A1 (en) *	2009-10-02	2011-04-07	Straitmark Holding Ag	Method for the manufacture of aminohydroxy diphosphonic acids
EP2665734B1 (de) *	2011-01-21	2016-06-29	Straitmark Holding AG	Verfahren zur herstellung von verbindungen mit einer alpha-oxy-phosphorgruppe
CN121203646B (zh) *	2025-11-28	2026-02-24	四川雷驰力奥石油科技有限公司	一种防垢交联聚合物压裂液体及其制备方法

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DE2702631A1 (de)	1977-01-22	1978-07-27	Henkel Kgaa	Verfahren zur herstellung von 1-hydroxy-3-amino-propan-1,1-diphosphonsaeuren
DE3016289A1 (de)	1980-04-28	1981-10-29	Henkel KGaA, 4000 Düsseldorf	Verfahren zur herstellung von omega -amino-1-hydroxyalkyliden-1,1-bis-phosphonsaeuren
DE3428524A1 (de)	1984-08-02	1986-02-13	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
US4990503A (en)	1988-08-12	1991-02-05	Yamanouchi Pharmaceutical Co., Ltd.	Heterocyclic bisphosphonic acid derivatives
US4922007A (en)	1989-06-09	1990-05-01	Merck & Co., Inc.	Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof
US5019651A (en)	1990-06-20	1991-05-28	Merck & Co., Inc.	Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (ABP) or salts thereof
US5159108A (en) *	1990-09-18	1992-10-27	Merck & Co., Inc.	Process for preparing an antihypercalcemic agent
US5039819A (en) *	1990-09-18	1991-08-13	Merck & Co., Inc.	Diphosphonate intermediate for preparing an antihypercalcemic agent
IT1246992B (it)	1991-01-08	1994-12-12	Gentili Ist Spa	Procedimento per la preparazione di acidi difosfonici e loro sali
IT1244698B (it) *	1991-02-01	1994-08-08	Gentili Ist Spa	Acidi aril-o arilalchil-acil ammino-alchil-idrossidifosfonici, procedimento per la loro preparazione e loro uso in terapia osteo-articolare e dei tessuti connettori in generale
CA2197267C (en)	1997-02-11	2000-02-08	Yong Tao	Process for the production of 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid or salts thereof
US5908859A (en)	1997-08-11	1999-06-01	Eli Lilly And Company	Benzothiophenes for inhibiting hyperlipidemia
YU59401A (sh) *	1999-02-17	2004-05-12	Teva Pharmaceutical Industries Ltd.	Postupak za proizvodnju alendronske kiseline
ES2153794B1 (es) *	1999-08-06	2001-10-16	Medichem Sa	Procedimiento para la obtencion del acido 4-amino-1-hidroxibutiliden-1,1-bisfosfonico y de su sal monosodica trihidratada.
PE20011061A1 (es) *	2000-02-01	2001-11-20	Procter & Gamble	Cristalizacion selectiva del acido 3-piridil-1-hidroxi-etiliden-1,1-bisfosfonico sodio como el hemipentahidrato o el monohidrato
TR200101250A2 (tr) *	2001-05-10	2003-04-21	E�S Eczaciba�I �Zg�N K�Myasal �R�Nler Sanay� A.�.	4-amino-1-hidroksibutiliden-1,1-bifosfonik asit veya tuzlarının hazırlanmasına ilişkin proses
JP3869456B2 (ja) *	2003-01-17	2007-01-17	テバファーマシューティカルインダストリーズリミティド	鉄含有量が非常に低いリセドロン酸ナトリウム
HUP0300227A2 (hu) *	2003-01-28	2004-09-28	Richter Gedeon Vegyészeti Gyár Rt.	Eljárás nagy tisztaságú 2-szubsztituált -1-(hidroxi-etilidén)-1,1-biszfoszfonsavak és sóik előállítására
ES2337063T3 (es) *	2003-08-21	2010-04-20	Sun Pharmaceuticals Industries Ltd.	Proceso para la preparacion de acido bisfosfonico.

2003
- 2003-01-28 HU HU0300227A patent/HUP0300227A2/hu unknown
2004
- 2004-01-27 EP EP04705466A patent/EP1587814B1/de not_active Expired - Lifetime
- 2004-01-27 DE DE602004019047T patent/DE602004019047D1/de not_active Expired - Lifetime
- 2004-01-27 WO PCT/HU2004/000009 patent/WO2004067541A1/en not_active Ceased
- 2004-01-27 EA EA200501188A patent/EA007947B1/ru not_active IP Right Cessation
- 2004-01-27 PL PL378438A patent/PL214441B1/pl unknown
- 2004-01-27 US US10/541,866 patent/US7612229B2/en not_active Expired - Lifetime
- 2004-01-27 AT AT04705466T patent/ATE420885T1/de not_active IP Right Cessation
- 2004-01-27 UA UAA200508269A patent/UA80023C2/uk unknown

Also Published As

Publication number	Publication date
PL378438A1 (pl)	2006-04-03
HU0300227D0 (en)	2003-03-28
HUP0300227A2 (hu)	2004-09-28
ATE420885T1 (de)	2009-01-15
DE602004019047D1 (de)	2009-03-05
US7612229B2 (en)	2009-11-03
EA200501188A1 (ru)	2005-12-29
EP1587814A1 (de)	2005-10-26
US20060122395A1 (en)	2006-06-08
EA007947B1 (ru)	2007-02-27
EP1587814B1 (de)	2009-01-14
WO2004067541A1 (en)	2004-08-12
PL214441B1 (pl)	2013-08-30

Publication	Publication Date	Title
AU728164B2 (en)	2001-01-04	Process for the production of 4-amino-1-hydroxybutylidene-1, 1-bisphosphonic acid or salts thereof
FI93219B (fi)	1994-11-30	Menetelmä 4-amino-1-hydroksibutylideeni-1,1-bisfosfonihapon tai sen suolojen valmistamiseksi
AU692468B2 (en)	1998-06-11	Process for producing N-amino-1-hydroxy-alkyl-idene-1,1-bisphosphonic acids
PT97963B (pt)	1998-11-30	Processo melhorado para a preparacao do acido 4-amino-1-hidroxibutilideno-1,1-bifosfonico (abp) ou dos seus sais
EP1891081B1 (de)	2014-08-20	Verfahren zur herstellung von bisphosphonsäuren und formen davon
CN102639545B (zh)	2016-08-03	制备氨基羟基二膦酸的方法
EA007947B1 (ru)	2007-02-27	Промышленный способ получения 2-замещенных 1-(гидроксиэтилиден)-1,1-бисфосфоновых кислот и их солей высокой чистоты
WO2008058722A1 (en)	2008-05-22	Reagent and use thereof for the production of bisphosphonates
US6573401B1 (en)	2003-06-03	Process for producing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid and its trihydrated monosodium salt
US20080194525A1 (en)	2008-08-14	Process of Making Geminal Bisphosphonic Acids and Pharmaceutically Acceptable Salts and/or Hydrates Thereof
WO2006071128A1 (en)	2006-07-06	Process for the preparation of [1-hydroxy-2-(3-pyridinyl)ethyliden] bisphosphonic acid and hemi-pentahydrate monosodium salt thereof
KR100665633B1 (ko)	2007-01-10	알렌드론산을 제조하는 신규한 방법
EP2192126B1 (de)	2013-03-27	Verfahren zur Herstellung von Zoledronsäure
JP5258370B2 (ja)	2013-08-07	リセドロン酸の工業的製造方法
JP3385208B2 (ja)	2003-03-10	ヘテロ環ビス（フォスフォン酸）誘導体の新規製造法
JPS6058996A (ja)	1985-04-05	ホスホノメチル化されたアミノ酸の製法
PL195455B1 (pl)	2007-09-28	Sposób wytwarzania kwasu 4-amino-1-hydroksybutano-1,1-bisfosfonowego oraz jego soli monosodowej
PL196357B1 (pl)	2007-12-31	Sposób wytwarzania pochodnych kwasów hydroksymetylenobisfosfonowych