LT3772B - Method for the preparation of xantynes nearly free from fluorescent impurity - Google Patents

Method for the preparation of xantynes nearly free from fluorescent impurity Download PDF

Info

Publication number: LT3772B
Authority: LT; Lithuania
Prior art keywords: xanthines; preparation; xantynes; fluorescent; precipitation
Prior art date: 1990-02-15

Application number

LTIP1463A

Other languages

English (en)

Lithuanian (lt)

Inventor

Rudolf Knieps

Ottmar Jaenicke

Walter Schoenfeld

Original Assignee

Hoechst Ag

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.)

1990-02-15

Filing date

1993-11-12

Publication date

1996-03-25

1993-11-12 Application filed by Hoechst Ag filed Critical Hoechst Ag

1995-05-25 Publication of LTIP1463A publication Critical patent/LTIP1463A/xx

1996-03-25 Publication of LT3772B publication Critical patent/LT3772B/lt

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 3
239000012535 impurity Substances 0.000 title description 3
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims abstract description 32
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims abstract description 14
238000001556 precipitation Methods 0.000 claims abstract description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
GMSNIKWWOQHZGF-UHFFFAOYSA-N 3-methyl-9H-xanthine Chemical compound O=C1NC(=O)N(C)C2=C1N=CN2 GMSNIKWWOQHZGF-UHFFFAOYSA-N 0.000 claims description 12
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims description 10
239000000047 product Substances 0.000 claims description 8
229940075420 xanthine Drugs 0.000 claims description 8
239000003513 alkali Substances 0.000 claims description 6
229960004559 theobromine Drugs 0.000 claims description 5
239000002244 precipitate Substances 0.000 claims 4
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
239000012670 alkaline solution Substances 0.000 abstract description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
239000013078 crystal Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
229960000278 theophylline Drugs 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 3
238000000151 deposition Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
239000002585 base Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
230000008021 deposition Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
229960001476 pentoxifylline Drugs 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
MGUBQPRSQWCLCX-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C.CN1C(=O)NC(=O)C2=C1N=CN2C MGUBQPRSQWCLCX-UHFFFAOYSA-N 0.000 description 1
JDVQZFHNZYVOBA-UHFFFAOYSA-N 3-methyl-7h-purine-2,6-dione;sodium Chemical compound [Na].O=C1NC(=O)N(C)C2=C1NC=N2 JDVQZFHNZYVOBA-UHFFFAOYSA-N 0.000 description 1
BBTNLADSUVOPPN-UHFFFAOYSA-N 5,6-diaminouracil Chemical class NC=1NC(=O)NC(=O)C=1N BBTNLADSUVOPPN-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
101100520660 Drosophila melanogaster Poc1 gene Proteins 0.000 description 1
101100520662 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PBA1 gene Proteins 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000003916 acid precipitation Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
-1 for example Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Luminescent Compositions (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Saccharide Compounds (AREA)
Cosmetics (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Compounds Of Unknown Constitution (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

LTIP1463A 1990-02-15 1993-11-12 Method for the preparation of xantynes nearly free from fluorescent impurity LT3772B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4004618A DE4004618A1 (de)	1990-02-15	1990-02-15	Verfahren zur gewinnung annaehernd fluoreszenzfreier xanthine

Publications (2)

Publication Number	Publication Date
LTIP1463A LTIP1463A (en)	1995-05-25
LT3772B true LT3772B (en)	1996-03-25

Family

ID=6400165

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP1463A LT3772B (en)	1990-02-15	1993-11-12	Method for the preparation of xantynes nearly free from fluorescent impurity

Country Status (19)

Country	Link
US (1)	US5144033A (cs)
EP (1)	EP0442401B1 (cs)
JP (1)	JP2550443B2 (cs)
KR (1)	KR0169984B1 (cs)
CN (1)	CN1032002C (cs)
AT (1)	ATE104979T1 (cs)
CZ (1)	CZ279936B6 (cs)
DE (2)	DE4004618A1 (cs)
DK (1)	DK0442401T3 (cs)
ES (1)	ES2054383T3 (cs)
IN (1)	IN171029B (cs)
LT (1)	LT3772B (cs)
LV (1)	LV10454B (cs)
PL (1)	PL165701B1 (cs)
PT (1)	PT96766B (cs)
RO (1)	RO107947B1 (cs)
RU (1)	RU1811531C (cs)
SK (1)	SK278938B6 (cs)
UA (1)	UA19846A (cs)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE21220C (de)			CH. W. siemens in London	Neuerungen an rotirenden Oefen

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD21220A (cs) *
DE138444C (cs) *	1901-12-31
GB190504959A (en) *	1905-03-09	1905-10-05	Anilin Fabrikation Ag	Manufacture of Soluble Compounds of Theobromine.
GB302207A (en) *	1927-09-12	1928-12-12	Albert Boehringer	Process for the extraction of theo-bromine

1990
- 1990-02-15 DE DE4004618A patent/DE4004618A1/de not_active Withdrawn
- 1990-08-28 IN IN684/MAS/90A patent/IN171029B/en unknown
1991
- 1991-02-09 EP EP91101829A patent/EP0442401B1/de not_active Expired - Lifetime
- 1991-02-09 DK DK91101829.9T patent/DK0442401T3/da active
- 1991-02-09 ES ES91101829T patent/ES2054383T3/es not_active Expired - Lifetime
- 1991-02-09 AT AT9191101829T patent/ATE104979T1/de not_active IP Right Cessation
- 1991-02-09 DE DE59101466T patent/DE59101466D1/de not_active Expired - Lifetime
- 1991-02-12 CN CN91100929A patent/CN1032002C/zh not_active Expired - Lifetime
- 1991-02-13 CZ CS91360A patent/CZ279936B6/cs not_active IP Right Cessation
- 1991-02-13 RO RO146925A patent/RO107947B1/ro unknown
- 1991-02-13 SK SK360-91A patent/SK278938B6/sk not_active IP Right Cessation
- 1991-02-13 KR KR1019910002496A patent/KR0169984B1/ko not_active Expired - Lifetime
- 1991-02-13 US US07/654,487 patent/US5144033A/en not_active Expired - Lifetime
- 1991-02-14 JP JP3040793A patent/JP2550443B2/ja not_active Expired - Lifetime
- 1991-02-14 PT PT96766A patent/PT96766B/pt not_active IP Right Cessation
- 1991-02-14 UA UA4894528A patent/UA19846A/uk unknown
- 1991-02-14 PL PL91289066A patent/PL165701B1/pl unknown
- 1991-02-14 RU SU914894528A patent/RU1811531C/ru active
1993
- 1993-05-05 LV LVP-93-290A patent/LV10454B/lv unknown
- 1993-11-12 LT LTIP1463A patent/LT3772B/lt not_active IP Right Cessation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE21220C (de)			CH. W. siemens in London	Neuerungen an rotirenden Oefen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
FRITZ ULLMANN: "Ullmanns encyclopedia of industrial chemistry, 4th ed", pages: 579

Also Published As

Publication number	Publication date
LTIP1463A (en)	1995-05-25
JP2550443B2 (ja)	1996-11-06
IN171029B (cs)	1992-07-04
DE4004618A1 (de)	1991-08-22
EP0442401B1 (de)	1994-04-27
JPH04330074A (ja)	1992-11-18
CN1054067A (zh)	1991-08-28
ATE104979T1 (de)	1994-05-15
UA19846A (uk)	1997-12-25
RU1811531C (ru)	1993-04-23
CS9100360A2 (en)	1991-09-15
RO107947B1 (ro)	1994-01-31
DK0442401T3 (da)	1994-09-05
EP0442401A1 (de)	1991-08-21
CN1032002C (zh)	1996-06-12
ES2054383T3 (es)	1994-08-01
PT96766A (pt)	1991-10-31
SK278938B6 (sk)	1998-04-08
PL165701B1 (pl)	1995-01-31
PT96766B (pt)	1998-07-31
US5144033A (en)	1992-09-01
PL289066A1 (en)	1991-09-23
KR0169984B1 (ko)	1999-02-01
LV10454B (en)	1996-02-20
KR910015577A (ko)	1991-09-30
DE59101466D1 (de)	1994-06-01
CZ279936B6 (cs)	1995-09-13
LV10454A (lv)	1995-02-20

Legal Events

Date

Code

Title

Description

2000-11-27

PC9A

Transfer of patents

Free format text: AVENTIS PHARMA DEUTSCHLAND GMBH, 65926 FRANKFURT AM MAIN, INDUSTRIEPARK HOCHST, DE 000928

2005-12-27

PD9A

Change of patent owner

Owner name: SANOFI-AVENTIS DEUTSCHLAND GMBH, DE

Effective date: 20051026

2013-12-27

MK9A

Expiry of a patent

Effective date: 20131112

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